NO327581B1 - Pyrimidinforbindelse, farmasoytisk preparat omfattende denne, og anvendelser av forbindelsen. - Google Patents

Pyrimidinforbindelse, farmasoytisk preparat omfattende denne, og anvendelser av forbindelsen. Download PDF

Info

Publication number: NO327581B1
Authority: NO; Norway
Prior art keywords: group; furyl; compound; pyrimidinyl; dihydro
Prior art date: 2001-10-22

Application number

NO20041580A

Other languages

English (en)

Norwegian (no)

Other versions

NO20041580L (no

Inventor

Yoshihiko Kotake

Shuhei Miyazawa

Hitoshi Harada

Osamu Asano

Masato Ueda

Masahiro Yasuda

Daisuke Iida

Yasuhiro Kabasawa

Nobuyuki Yasuda

Junichi Nagakawa

Kazuo Hirota

Makoto Nakagawa

Original Assignee

Eisai R&D Man Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-10-22

Filing date

2004-04-19

Publication date

2009-08-24

2004-04-19 Application filed by Eisai R&D Man Co Ltd filed Critical Eisai R&D Man Co Ltd

2004-07-22 Publication of NO20041580L publication Critical patent/NO20041580L/no

2009-08-24 Publication of NO327581B1 publication Critical patent/NO327581B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 301
-1 Pyrimidine compound Chemical class 0.000 title description 91
239000008194 pharmaceutical composition Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims description 62
239000003795 chemical substances by application Substances 0.000 claims description 52
239000012453 solvate Substances 0.000 claims description 47
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
206010010774 Constipation Diseases 0.000 claims description 43
238000004519 manufacturing process Methods 0.000 claims description 43
125000005843 halogen group Chemical group 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 28
125000004076 pyridyl group Chemical group 0.000 claims description 25
239000000825 pharmaceutical preparation Substances 0.000 claims description 20
125000001544 thienyl group Chemical group 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 17
208000018737 Parkinson disease Diseases 0.000 claims description 15
125000002541 furyl group Chemical group 0.000 claims description 15
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
210000001035 gastrointestinal tract Anatomy 0.000 claims description 14
230000002265 prevention Effects 0.000 claims description 13
208000002551 irritable bowel syndrome Diseases 0.000 claims description 12
208000008384 ileus Diseases 0.000 claims description 11
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 8
KXDNYLRDVSRARZ-UHFFFAOYSA-N 5-(2-amino-4-thiophen-2-ylpyrimidin-5-yl)-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CS1 KXDNYLRDVSRARZ-UHFFFAOYSA-N 0.000 claims description 7
LWPWANLSNUFFAH-UHFFFAOYSA-N 5-[2,4-diamino-6-(3-fluorophenyl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=C(N)N=C(N)N=C1C1=CC=CC(F)=C1 LWPWANLSNUFFAH-UHFFFAOYSA-N 0.000 claims description 6
RWOLMPQKNXRXFP-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-ethylpyridin-2-one Chemical compound C1=CC(=O)N(CC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 RWOLMPQKNXRXFP-UHFFFAOYSA-N 0.000 claims description 6
KLQQNDZPIWTDSO-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CO1 KLQQNDZPIWTDSO-UHFFFAOYSA-N 0.000 claims description 6
208000024827 Alzheimer disease Diseases 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
208000011231 Crohn disease Diseases 0.000 claims description 6
208000002249 Diabetes Complications Diseases 0.000 claims description 6
206010012655 Diabetic complications Diseases 0.000 claims description 6
206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
208000002705 Glucose Intolerance Diseases 0.000 claims description 6
206010018429 Glucose tolerance impaired Diseases 0.000 claims description 6
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
208000008589 Obesity Diseases 0.000 claims description 6
208000001132 Osteoporosis Diseases 0.000 claims description 6
230000001430 anti-depressive effect Effects 0.000 claims description 6
239000000935 antidepressant agent Substances 0.000 claims description 6
229940005513 antidepressants Drugs 0.000 claims description 6
239000003472 antidiabetic agent Substances 0.000 claims description 6
239000002220 antihypertensive agent Substances 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
206010012601 diabetes mellitus Diseases 0.000 claims description 6
239000002934 diuretic Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229940126904 hypoglycaemic agent Drugs 0.000 claims description 6
235000020824 obesity Nutrition 0.000 claims description 6
LXMGWNGPIIDYEZ-UHFFFAOYSA-N 5-(2-amino-4-phenylpyrimidin-5-yl)-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CC=C1 LXMGWNGPIIDYEZ-UHFFFAOYSA-N 0.000 claims description 5
CTYOLHLKCVSGEG-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=C(C=2OC=CC=2)N=C(N)N=C1C1=CC=CO1 CTYOLHLKCVSGEG-UHFFFAOYSA-N 0.000 claims description 5
GIIUUEOCDDLBQZ-UHFFFAOYSA-N 5-[2-amino-4-(3-fluorophenyl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CC(F)=C1 GIIUUEOCDDLBQZ-UHFFFAOYSA-N 0.000 claims description 5
206010010356 Congenital anomaly Diseases 0.000 claims description 5
230000004064 dysfunction Effects 0.000 claims description 5
230000006872 improvement Effects 0.000 claims description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
102000004877 Insulin Human genes 0.000 claims description 4
108090001061 Insulin Proteins 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229940125396 insulin Drugs 0.000 claims description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
WJNNXYLGOHCGCH-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-fluoroethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCF)C=1 WJNNXYLGOHCGCH-UHFFFAOYSA-N 0.000 claims description 3
QONUMVWLFMVXOC-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methoxyethyl)pyridin-2-one Chemical compound C1=CC(=O)N(CCOC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 QONUMVWLFMVXOC-UHFFFAOYSA-N 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000002560 nitrile group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
231100000489 sensitizer Toxicity 0.000 claims description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 164
238000006243 chemical reaction Methods 0.000 description 124
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 108
239000002904 solvent Substances 0.000 description 99
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 85
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
239000007858 starting material Substances 0.000 description 57
239000002585 base Substances 0.000 description 54
239000000243 solution Substances 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 42
239000007787 solid Substances 0.000 description 40
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 37
239000011541 reaction mixture Substances 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 35
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
238000012360 testing method Methods 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
229910052783 alkali metal Inorganic materials 0.000 description 29
125000006615 aromatic heterocyclic group Chemical group 0.000 description 28
238000001914 filtration Methods 0.000 description 28
150000002357 guanidines Chemical class 0.000 description 28
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
125000004432 carbon atom Chemical group C* 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
238000003756 stirring Methods 0.000 description 24
102000005962 receptors Human genes 0.000 description 23
108020003175 receptors Proteins 0.000 description 23
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 22
238000002360 preparation method Methods 0.000 description 22
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
102000009346 Adenosine receptors Human genes 0.000 description 20
108050000203 Adenosine receptors Proteins 0.000 description 20
239000003153 chemical reaction reagent Substances 0.000 description 20
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 20
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
238000000034 method Methods 0.000 description 19
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
238000001816 cooling Methods 0.000 description 17
101150078577 Adora2b gene Proteins 0.000 description 16
235000019270 ammonium chloride Nutrition 0.000 description 16
150000003230 pyrimidines Chemical class 0.000 description 16
239000000725 suspension Substances 0.000 description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000012298 atmosphere Substances 0.000 description 14
229910001873 dinitrogen Inorganic materials 0.000 description 14
201000010099 disease Diseases 0.000 description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
230000000694 effects Effects 0.000 description 14
239000000706 filtrate Substances 0.000 description 14
239000012046 mixed solvent Substances 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
239000002994 raw material Substances 0.000 description 14
239000002126 C01EB10 - Adenosine Substances 0.000 description 13
239000002253 acid Substances 0.000 description 13
229960005305 adenosine Drugs 0.000 description 13
150000001298 alcohols Chemical class 0.000 description 13
230000027455 binding Effects 0.000 description 13
150000002170 ethers Chemical class 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
239000007800 oxidant agent Substances 0.000 description 11
239000011734 sodium Substances 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 10
PZNCKJDSGSPNMQ-UHFFFAOYSA-N 2-(2-fluoropyridin-4-yl)-1-(furan-2-yl)ethanone Chemical compound C1=NC(F)=CC(CC(=O)C=2OC=CC=2)=C1 PZNCKJDSGSPNMQ-UHFFFAOYSA-N 0.000 description 10
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 10
108010085277 Adenosine A2A receptor Proteins 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000012267 brine Substances 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
RRLMPLDPCKRASL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enal Chemical class CN(C)C=CC=O RRLMPLDPCKRASL-UHFFFAOYSA-N 0.000 description 9
ACFHETZZSOOPTG-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1h-pyridin-2-one Chemical compound C1=CC(=O)NC=C1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 ACFHETZZSOOPTG-UHFFFAOYSA-N 0.000 description 9
102000007471 Adenosine A2A receptor Human genes 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 9
239000010410 layer Substances 0.000 description 9
210000003141 lower extremity Anatomy 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
210000001364 upper extremity Anatomy 0.000 description 9
102000000506 Adenosine A2 Receptors Human genes 0.000 description 8
108010041368 Adenosine A2 Receptors Proteins 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
229910000288 alkali metal carbonate Inorganic materials 0.000 description 8
150000008041 alkali metal carbonates Chemical class 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
239000000843 powder Substances 0.000 description 8
208000009132 Catalepsy Diseases 0.000 description 7
JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
206010047853 Waxy flexibility Diseases 0.000 description 7
150000001340 alkali metals Chemical class 0.000 description 7
229920000609 methyl cellulose Polymers 0.000 description 7
235000010981 methylcellulose Nutrition 0.000 description 7
239000001923 methylcellulose Substances 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
PJCPGNVJRUZUCE-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 PJCPGNVJRUZUCE-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
101150051188 Adora2a gene Proteins 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
230000008485 antagonism Effects 0.000 description 6
239000005557 antagonist Substances 0.000 description 6
238000009833 condensation Methods 0.000 description 6
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
239000003814 drug Substances 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
229960003878 haloperidol Drugs 0.000 description 6
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
229940044551 receptor antagonist Drugs 0.000 description 6
239000002464 receptor antagonist Substances 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
239000011593 sulfur Substances 0.000 description 6
IUTHGAAXFHBXRJ-UHFFFAOYSA-N 4-chloro-6-(furan-2-yl)-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=COC=1C1=NC(N)=NC(Cl)=C1C1=CC=NC=C1 IUTHGAAXFHBXRJ-UHFFFAOYSA-N 0.000 description 5
HYCDHZLPQJQZDV-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1h-pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)NC=1 HYCDHZLPQJQZDV-UHFFFAOYSA-N 0.000 description 5
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 5
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 5
239000003963 antioxidant agent Substances 0.000 description 5
235000006708 antioxidants Nutrition 0.000 description 5
238000005899 aromatization reaction Methods 0.000 description 5
239000003086 colorant Substances 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229960000789 guanidine hydrochloride Drugs 0.000 description 5
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
150000002697 manganese compounds Chemical class 0.000 description 5
239000012528 membrane Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
150000004053 quinones Chemical class 0.000 description 5
239000003826 tablet Substances 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
XQSYGQZXBWJMJX-UHFFFAOYSA-N 1-(furan-2-yl)-2-pyridin-4-ylethanone Chemical compound C=1C=COC=1C(=O)CC1=CC=NC=C1 XQSYGQZXBWJMJX-UHFFFAOYSA-N 0.000 description 4
LQSVDFBZKRZVQD-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-1-(furan-2-yl)ethanone Chemical compound C1=NC(Cl)=CC=C1CC(=O)C1=CC=CO1 LQSVDFBZKRZVQD-UHFFFAOYSA-N 0.000 description 4
PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 4
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
102000007470 Adenosine A2B Receptor Human genes 0.000 description 4
108010085273 Adenosine A2B receptor Proteins 0.000 description 4
229940123702 Adenosine A2a receptor antagonist Drugs 0.000 description 4
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
MMWCIQZXVOZEGG-HOZKJCLWSA-N [(1S,2R,3S,4S,5R,6S)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate Chemical compound O[C@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](O)[C@H]1OP(O)(O)=O MMWCIQZXVOZEGG-HOZKJCLWSA-N 0.000 description 4
239000002467 adenosine A2a receptor antagonist Substances 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
229910001424 calcium ion Inorganic materials 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
210000001653 corpus striatum Anatomy 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
239000003365 glass fiber Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000002198 insoluble material Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
230000009871 nonspecific binding Effects 0.000 description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
SUYNWWIQTVLVBM-UHFFFAOYSA-N (6-chloropyridin-3-yl)methyl methanesulfonate Chemical compound CS(=O)(=O)OCC1=CC=C(Cl)N=C1 SUYNWWIQTVLVBM-UHFFFAOYSA-N 0.000 description 3
XFMRAFPIRFRBFU-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)pyrimidin-2-amine Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C1=CC=NC(F)=C1 XFMRAFPIRFRBFU-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
102000014384 Type C Phospholipases Human genes 0.000 description 3
108010079194 Type C Phospholipases Proteins 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
102000030621 adenylate cyclase Human genes 0.000 description 3
108060000200 adenylate cyclase Proteins 0.000 description 3
229910000102 alkali metal hydride Inorganic materials 0.000 description 3
150000008046 alkali metal hydrides Chemical class 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
239000007853 buffer solution Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
210000001072 colon Anatomy 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
239000012043 crude product Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
238000009826 distribution Methods 0.000 description 3
229960003638 dopamine Drugs 0.000 description 3
210000005064 dopaminergic neuron Anatomy 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000012156 elution solvent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000945 filler Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
150000002222 fluorine compounds Chemical class 0.000 description 3
235000013355 food flavoring agent Nutrition 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229940014259 gelatin Drugs 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
230000003834 intracellular effect Effects 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
210000003205 muscle Anatomy 0.000 description 3
230000010807 negative regulation of binding Effects 0.000 description 3
239000008188 pellet Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 3
150000008318 pyrimidones Chemical class 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
238000001308 synthesis method Methods 0.000 description 3
GOXYBEXWMJZLJB-UHFFFAOYSA-N (6-chloropyridin-3-yl)methanol Chemical compound OCC1=CC=C(Cl)N=C1 GOXYBEXWMJZLJB-UHFFFAOYSA-N 0.000 description 2
DWUCQENWVUKDGW-QPEQYQDCSA-N (e)-3-(3-fluorophenyl)-2-(6-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound C1=NC(OC)=CC=C1C(\C#N)=C/C1=CC=CC(F)=C1 DWUCQENWVUKDGW-QPEQYQDCSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
LNNXOEHOXSYWLD-UHFFFAOYSA-N 1-bromobut-2-yne Chemical compound CC#CCBr LNNXOEHOXSYWLD-UHFFFAOYSA-N 0.000 description 2
LVYJIIRJQDEGBR-UHFFFAOYSA-N 1-fluoro-2-iodoethane Chemical compound FCCI LVYJIIRJQDEGBR-UHFFFAOYSA-N 0.000 description 2
MXIIMMZKZGTDQT-UHFFFAOYSA-N 2-(2-bromopyridin-4-yl)-1-(furan-2-yl)ethanone Chemical compound C1=NC(Br)=CC(CC(=O)C=2OC=CC=2)=C1 MXIIMMZKZGTDQT-UHFFFAOYSA-N 0.000 description 2
XTVVOZUTBMDQAO-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-1-(3-fluorophenyl)ethanone Chemical compound FC1=CC=CC(C(=O)CC=2C=NC(Cl)=CC=2)=C1 XTVVOZUTBMDQAO-UHFFFAOYSA-N 0.000 description 2
IKYYRRUDOFAYPO-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-1-phenylethanone Chemical compound C1=NC(Cl)=CC=C1CC(=O)C1=CC=CC=C1 IKYYRRUDOFAYPO-UHFFFAOYSA-N 0.000 description 2
JDZKGWYZMARUMA-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-1-thiophen-2-ylethanone Chemical compound C1=NC(Cl)=CC=C1CC(=O)C1=CC=CS1 JDZKGWYZMARUMA-UHFFFAOYSA-N 0.000 description 2
AWPYFGCGVOFFOC-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-3-(dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-one Chemical compound C=1C=C(Cl)N=CC=1C(=CN(C)C)C(=O)C1=CC=CC(F)=C1 AWPYFGCGVOFFOC-UHFFFAOYSA-N 0.000 description 2
MPSIQJKERWNJQW-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-3-(dimethylamino)-1-(furan-2-yl)prop-2-en-1-one Chemical compound C=1C=C(Cl)N=CC=1C(=CN(C)C)C(=O)C1=CC=CO1 MPSIQJKERWNJQW-UHFFFAOYSA-N 0.000 description 2
GXXICWZPKTYVBH-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-3-(dimethylamino)-1-phenylprop-2-en-1-one Chemical compound C=1C=C(Cl)N=CC=1C(=CN(C)C)C(=O)C1=CC=CC=C1 GXXICWZPKTYVBH-UHFFFAOYSA-N 0.000 description 2
FEELUAQKAGSYNP-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-3-(dimethylamino)-1-thiophen-2-ylprop-2-en-1-one Chemical compound C=1C=C(Cl)N=CC=1C(=CN(C)C)C(=O)C1=CC=CS1 FEELUAQKAGSYNP-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
CXHZSBXWJLWQFF-UHFFFAOYSA-N 2-[4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]acetic acid Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CC(O)=O)C(=O)C=1 CXHZSBXWJLWQFF-UHFFFAOYSA-N 0.000 description 2
IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
TYWXVCAFFDUXLQ-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound C=1C=NC=CC=1C=1C(=O)NC(N)=NC=1C1=CC=CC(F)=C1 TYWXVCAFFDUXLQ-UHFFFAOYSA-N 0.000 description 2
POHPUSLVPTYISG-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound C=1C=NC=CC=1C=1C(=O)NC(N)=NC=1C1=CC=CO1 POHPUSLVPTYISG-UHFFFAOYSA-N 0.000 description 2
BMVSAKPRNWZCPG-UHFFFAOYSA-N 2-pyridin-4-ylacetonitrile Chemical compound N#CCC1=CC=NC=C1 BMVSAKPRNWZCPG-UHFFFAOYSA-N 0.000 description 2
FZMFPCLBMUFJGR-UHFFFAOYSA-N 3-(dimethylamino)-1-(furan-2-yl)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CO1 FZMFPCLBMUFJGR-UHFFFAOYSA-N 0.000 description 2
CQVWOJSAGPFDQL-UHFFFAOYSA-N 3-iodopropan-1-ol Chemical compound OCCCI CQVWOJSAGPFDQL-UHFFFAOYSA-N 0.000 description 2
JBAJMLMKIIDEJX-UHFFFAOYSA-N 4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound N=1C(N)=NC(C=2OC=CC=2)=CC=1C1=CC=CO1 JBAJMLMKIIDEJX-UHFFFAOYSA-N 0.000 description 2
TVCSEKNSHXOTRH-UHFFFAOYSA-N 4-(furan-2-yl)-5-(6-phenylmethoxypyridin-3-yl)pyrimidin-2-amine Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(C=N1)=CC=C1OCC1=CC=CC=C1 TVCSEKNSHXOTRH-UHFFFAOYSA-N 0.000 description 2
JTOGGBLTIHXWEH-UHFFFAOYSA-N 4-(furan-2-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2OC=CC=2)=N1 JTOGGBLTIHXWEH-UHFFFAOYSA-N 0.000 description 2
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
FDXGBDALWIWIJI-UHFFFAOYSA-N 4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 FDXGBDALWIWIJI-UHFFFAOYSA-N 0.000 description 2
IVPBXSXMIXDNCP-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1h-pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CNC(=O)C=1 IVPBXSXMIXDNCP-UHFFFAOYSA-N 0.000 description 2
CVBIYDYLLHPKEU-UHFFFAOYSA-N 4-chloro-6-(3-fluorophenyl)-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=CC(F)=CC=1C1=NC(N)=NC(Cl)=C1C1=CC=NC=C1 CVBIYDYLLHPKEU-UHFFFAOYSA-N 0.000 description 2
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
150000005696 4-halopyrimidines Chemical class 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
NEEWZBACFPYCAD-UHFFFAOYSA-N 5-(2-amino-4-thiophen-2-ylpyrimidin-5-yl)-1h-pyridin-2-one Chemical compound C=1C=CSC=1C1=NC(N)=NC=C1C=1C=CC(=O)NC=1 NEEWZBACFPYCAD-UHFFFAOYSA-N 0.000 description 2
COJWMXAUUNNHAR-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-(furan-3-yl)pyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C=1C=COC=1 COJWMXAUUNNHAR-UHFFFAOYSA-N 0.000 description 2
DINLWOJVLUFASI-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-phenylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2C=CC=CC=2)=NC(N)=NC=1C1=CC=CO1 DINLWOJVLUFASI-UHFFFAOYSA-N 0.000 description 2
RZZAPLSESLZDBG-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-pyridin-2-ylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2N=CC=CC=2)=NC(N)=NC=1C1=CC=CO1 RZZAPLSESLZDBG-UHFFFAOYSA-N 0.000 description 2
CIYIDAKCOKLWLK-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-pyridin-3-ylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2C=NC=CC=2)=NC(N)=NC=1C1=CC=CO1 CIYIDAKCOKLWLK-UHFFFAOYSA-N 0.000 description 2
ATFBOSCBLMVFRM-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2C=CN=CC=2)=NC(N)=NC=1C1=CC=CO1 ATFBOSCBLMVFRM-UHFFFAOYSA-N 0.000 description 2
GBEDQNBURCBZRF-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-thiophen-2-ylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2SC=CC=2)=NC(N)=NC=1C1=CC=CO1 GBEDQNBURCBZRF-UHFFFAOYSA-N 0.000 description 2
QESYKNGVJNWMLT-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-thiophen-3-ylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C=1C=CSC=1 QESYKNGVJNWMLT-UHFFFAOYSA-N 0.000 description 2
ARRICDDGPWDUQK-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C=1C=C(Cl)N=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 ARRICDDGPWDUQK-UHFFFAOYSA-N 0.000 description 2
NEROLKMROBGTQF-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-4-(3-fluorophenyl)pyrimidin-2-amine Chemical compound C=1C=CC(F)=CC=1C1=NC(N)=NC=C1C1=CC=C(Cl)N=C1 NEROLKMROBGTQF-UHFFFAOYSA-N 0.000 description 2
VVVNMWDGGSIPMV-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-4-(furan-2-yl)pyrimidin-2-amine Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C1=CC=C(Cl)N=C1 VVVNMWDGGSIPMV-UHFFFAOYSA-N 0.000 description 2
GKHLIODVGUNPLL-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-4-phenylpyrimidin-2-amine Chemical compound C=1C=CC=CC=1C1=NC(N)=NC=C1C1=CC=C(Cl)N=C1 GKHLIODVGUNPLL-UHFFFAOYSA-N 0.000 description 2
OPYTUUTUJHCMJT-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-4-thiophen-2-ylpyrimidin-2-amine Chemical compound C=1C=CSC=1C1=NC(N)=NC=C1C1=CC=C(Cl)N=C1 OPYTUUTUJHCMJT-UHFFFAOYSA-N 0.000 description 2
NSCUEDKXJDZKNW-UHFFFAOYSA-N 5-[2,4-diamino-6-(3-fluorophenyl)pyrimidin-5-yl]-1h-pyridin-2-one Chemical compound C=1C=CC(F)=CC=1C1=NC(N)=NC(N)=C1C=1C=CC(=O)NC=1 NSCUEDKXJDZKNW-UHFFFAOYSA-N 0.000 description 2
IYBPHHBXSLOGND-UHFFFAOYSA-N 5-[2-amino-4-(3-fluorophenyl)pyrimidin-5-yl]-1h-pyridin-2-one Chemical compound C=1C=CC(F)=CC=1C1=NC(N)=NC=C1C=1C=CC(=O)NC=1 IYBPHHBXSLOGND-UHFFFAOYSA-N 0.000 description 2
LXKTVNFZAFTUNZ-UHFFFAOYSA-N 5-bromo-2-phenylmethoxypyridine Chemical compound N1=CC(Br)=CC=C1OCC1=CC=CC=C1 LXKTVNFZAFTUNZ-UHFFFAOYSA-N 0.000 description 2
QEFGSYOHUBGGJW-UHFFFAOYSA-N 5-bromo-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound BrC=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 QEFGSYOHUBGGJW-UHFFFAOYSA-N 0.000 description 2
KIMSQHCTXKUJBQ-UHFFFAOYSA-N 5-bromo-4-(furan-2-yl)pyrimidin-2-amine Chemical compound NC1=NC=C(Br)C(C=2OC=CC=2)=N1 KIMSQHCTXKUJBQ-UHFFFAOYSA-N 0.000 description 2
150000005697 5-halopyrimidines Chemical class 0.000 description 2
APCJPZZJBPFUKE-UHFFFAOYSA-N 6-(3-fluorophenyl)-5-(6-methoxypyridin-3-yl)pyrimidine-2,4-diamine Chemical compound C1=NC(OC)=CC=C1C1=C(N)N=C(N)N=C1C1=CC=CC(F)=C1 APCJPZZJBPFUKE-UHFFFAOYSA-N 0.000 description 2
KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
101150049660 DRD2 gene Proteins 0.000 description 2
239000004375 Dextrin Substances 0.000 description 2
229920001353 Dextrin Polymers 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
208000012661 Dyskinesia Diseases 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
239000007995 HEPES buffer Substances 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
229940122355 Insulin sensitizer Drugs 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000010775 animal oil Substances 0.000 description 2
230000002421 anti-septic effect Effects 0.000 description 2
229940064004 antiseptic throat preparations Drugs 0.000 description 2
150000003934 aromatic aldehydes Chemical class 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
210000005252 bulbus oculi Anatomy 0.000 description 2
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 2
239000001354 calcium citrate Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
230000030833 cell death Effects 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000002299 complementary DNA Substances 0.000 description 2
235000019425 dextrin Nutrition 0.000 description 2
NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
239000006196 drop Substances 0.000 description 2
239000010696 ester oil Substances 0.000 description 2
XSUOOLGCZGWJFD-UHFFFAOYSA-N ethyl 1-[4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]pyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=CC=N1 XSUOOLGCZGWJFD-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000003889 eye drop Substances 0.000 description 2
229940012356 eye drops Drugs 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
230000006870 function Effects 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
239000003446 ligand Substances 0.000 description 2
239000012669 liquid formulation Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
210000001259 mesencephalon Anatomy 0.000 description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000012434 nucleophilic reagent Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000003002 pH adjusting agent Substances 0.000 description 2
235000010987 pectin Nutrition 0.000 description 2
239000001814 pectin Substances 0.000 description 2
229920001277 pectin Polymers 0.000 description 2
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
229940068968 polysorbate 80 Drugs 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000008213 purified water Substances 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
238000011160 research Methods 0.000 description 2
230000001235 sensitizing effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229920002545 silicone oil Polymers 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
230000009870 specific binding Effects 0.000 description 2
PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
210000003523 substantia nigra Anatomy 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
235000013337 tricalcium citrate Nutrition 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
229910052722 tritium Inorganic materials 0.000 description 2
210000003932 urinary bladder Anatomy 0.000 description 2
210000004291 uterus Anatomy 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
229920003169 water-soluble polymer Polymers 0.000 description 2
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
YFHFSUXFKSXIJY-NZQZLILVSA-N (2r,3s,4r,5r)-2-(6-aminopurin-9-yl)-3-chloro-2-cyclopentyl-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@]1(C2CCCC2)O[C@H](CO)[C@@H](O)[C@]1(O)Cl YFHFSUXFKSXIJY-NZQZLILVSA-N 0.000 description 1
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
XGVTXQKGMIVZMX-LCYFTJDESA-N (e)-4-(furan-2-yl)-3-pyridin-4-ylbut-3-en-2-one Chemical compound C=1C=NC=CC=1/C(C(=O)C)=C\C1=CC=CO1 XGVTXQKGMIVZMX-LCYFTJDESA-N 0.000 description 1
MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
125000005926 1,2-dimethylbutyloxy group Chemical group 0.000 description 1
125000005923 1,2-dimethylpropyloxy group Chemical group 0.000 description 1
HUXJXNSHCKHFIL-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-methoxyethane Chemical compound COCCOCCBr HUXJXNSHCKHFIL-UHFFFAOYSA-N 0.000 description 1
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
WTFQJWMPEJANTG-UHFFFAOYSA-N 1-[4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]pyridin-2-yl]piperidin-4-ol Chemical compound C=1C=NC(N2CCC(O)CC2)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 WTFQJWMPEJANTG-UHFFFAOYSA-N 0.000 description 1
XFPKSJFGNWNJAD-UHFFFAOYSA-N 1-[4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]pyridin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C=NC(N2CCC(CC2)C(O)=O)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 XFPKSJFGNWNJAD-UHFFFAOYSA-N 0.000 description 1
VNHWPVLQRKKKRY-UHFFFAOYSA-N 1-bromo-3-fluoropropane Chemical compound FCCCBr VNHWPVLQRKKKRY-UHFFFAOYSA-N 0.000 description 1
VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
125000006039 1-hexenyl group Chemical group 0.000 description 1
RHBHXHXNWHTGSO-UHFFFAOYSA-N 1-iodo-2-methylbutane Chemical compound CCC(C)CI RHBHXHXNWHTGSO-UHFFFAOYSA-N 0.000 description 1
BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 1
BUZZUHJODKQYTF-UHFFFAOYSA-N 1-iodo-3-methylbutane Chemical compound CC(C)CCI BUZZUHJODKQYTF-UHFFFAOYSA-N 0.000 description 1
125000006023 1-pentenyl group Chemical group 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
KRAYOUNNILABNQ-UHFFFAOYSA-N 2-[4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]pyridin-2-yl]oxyethanol Chemical compound C=1C=NC(OCCO)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 KRAYOUNNILABNQ-UHFFFAOYSA-N 0.000 description 1
MWZYIVNSNMCBQU-UHFFFAOYSA-N 2-[4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]-n,n-diethylacetamide Chemical compound O=C1N(CC(=O)N(CC)CC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 MWZYIVNSNMCBQU-UHFFFAOYSA-N 0.000 description 1
APMHFBSTSAORSW-UHFFFAOYSA-N 2-[4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]-n-phenylacetamide Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC(=O)NC1=CC=CC=C1 APMHFBSTSAORSW-UHFFFAOYSA-N 0.000 description 1
DLGYIFMUKLUKDY-UHFFFAOYSA-N 2-[[4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]pyridin-2-yl]amino]ethanol Chemical compound C=1C=NC(NCCO)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 DLGYIFMUKLUKDY-UHFFFAOYSA-N 0.000 description 1
LSZMVESSGLHDJE-UHFFFAOYSA-N 2-bromo-4-methylpyridine Chemical compound CC1=CC=NC(Br)=C1 LSZMVESSGLHDJE-UHFFFAOYSA-N 0.000 description 1
JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 1
KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 1
125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
ZBFAXMKJADVOGH-UHFFFAOYSA-N 2-fluoro-4-methylpyridine Chemical compound CC1=CC=NC(F)=C1 ZBFAXMKJADVOGH-UHFFFAOYSA-N 0.000 description 1
CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
QSECPQCFCWVBKM-UHFFFAOYSA-N 2-iodoethanol Chemical compound OCCI QSECPQCFCWVBKM-UHFFFAOYSA-N 0.000 description 1
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000005924 2-methylpentyloxy group Chemical group 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
CITGMZFNHZEDQA-UHFFFAOYSA-N 3-(dimethylamino)-1-(furan-2-yl)-2-pyridin-4-ylprop-2-en-1-one Chemical compound C=1C=NC=CC=1C(=CN(C)C)C(=O)C1=CC=CO1 CITGMZFNHZEDQA-UHFFFAOYSA-N 0.000 description 1
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
LDTQCLGREAWLQH-UHFFFAOYSA-N 3-[5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]propanenitrile Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCC#N)C=1 LDTQCLGREAWLQH-UHFFFAOYSA-N 0.000 description 1
CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000005925 3-methylpentyloxy group Chemical group 0.000 description 1
WAMJPDRFBKPYSZ-UHFFFAOYSA-N 4,6-bis(furan-2-yl)-5-(2-methoxypyridin-4-yl)pyrimidin-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 WAMJPDRFBKPYSZ-UHFFFAOYSA-N 0.000 description 1
XDMONPWVMMEUDA-UHFFFAOYSA-N 4,6-bis(furan-2-yl)-5-(6-phenylmethoxypyridin-3-yl)pyrimidin-2-amine Chemical compound C=1C=C(OCC=2C=CC=CC=2)N=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 XDMONPWVMMEUDA-UHFFFAOYSA-N 0.000 description 1
FAMOUEBOJFIYGA-UHFFFAOYSA-N 4,6-bis(furan-2-yl)-5-[2-(methylamino)pyridin-4-yl]pyridin-2-amine Chemical compound C1=NC(NC)=CC(C=2C(=NC(N)=CC=2C=2OC=CC=2)C=2OC=CC=2)=C1 FAMOUEBOJFIYGA-UHFFFAOYSA-N 0.000 description 1
UFVNXLNHTPDYGT-UHFFFAOYSA-N 4,6-bis(furan-2-yl)-5-[2-(propan-2-ylamino)pyridin-4-yl]pyrimidin-2-amine Chemical compound C1=NC(NC(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 UFVNXLNHTPDYGT-UHFFFAOYSA-N 0.000 description 1
LUHLZYXCUAOTNT-UHFFFAOYSA-N 4,6-bis(furan-2-yl)-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 LUHLZYXCUAOTNT-UHFFFAOYSA-N 0.000 description 1
NQVBHPFHNBJJBT-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptan-3-ol;4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1CC2(C)C(O)CC1C2(C)C.C1CC2(C)C(=O)CC1C2(C)C NQVBHPFHNBJJBT-UHFFFAOYSA-N 0.000 description 1
NGQFKZCCPNRCCG-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(OC)=NC(N)=NC=1C1=CC=CC(F)=C1 NGQFKZCCPNRCCG-UHFFFAOYSA-N 0.000 description 1
JYEOZZKMRDYHPE-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-propan-2-yloxy-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(OC(C)C)=NC(N)=NC=1C1=CC=CC(F)=C1 JYEOZZKMRDYHPE-UHFFFAOYSA-N 0.000 description 1
DJOWDNJSEDRTEF-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-propoxy-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(OCCC)=NC(N)=NC=1C1=CC=CC(F)=C1 DJOWDNJSEDRTEF-UHFFFAOYSA-N 0.000 description 1
JZMZHCKCWHVWBE-UHFFFAOYSA-N 4-(furan-2-yl)-6-methyl-5-pyridin-4-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C=NC=CC=1C=1C(C)=NC(N)=NC=1C1=CC=CO1 JZMZHCKCWHVWBE-UHFFFAOYSA-N 0.000 description 1
IPMNOEWUJDHOSS-UHFFFAOYSA-N 4-(furan-2-yl)-6-phenyl-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(C=2C=CC=CC=2)=NC(N)=NC=1C1=CC=CO1 IPMNOEWUJDHOSS-UHFFFAOYSA-N 0.000 description 1
ZGGZGWVFNMCLBC-UHFFFAOYSA-N 4-(furan-2-yl)-6-prop-2-enoxy-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=COC=1C1=NC(N)=NC(OCC=C)=C1C1=CC=NC=C1 ZGGZGWVFNMCLBC-UHFFFAOYSA-N 0.000 description 1
XHIGIRUGWQLDGL-UHFFFAOYSA-N 4-(furan-2-yl)-6-propan-2-yloxy-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(OC(C)C)=NC(N)=NC=1C1=CC=CO1 XHIGIRUGWQLDGL-UHFFFAOYSA-N 0.000 description 1
NTJLBQSMJWUJFU-UHFFFAOYSA-N 4-(furan-2-yl)-6-propoxy-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(OCCC)=NC(N)=NC=1C1=CC=CO1 NTJLBQSMJWUJFU-UHFFFAOYSA-N 0.000 description 1
XLGZYTXQHOJEMV-UHFFFAOYSA-N 4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-ethylpyridin-2-one Chemical compound O=C1N(CC)C=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 XLGZYTXQHOJEMV-UHFFFAOYSA-N 0.000 description 1
QMTOOVLTKNHAJE-UHFFFAOYSA-N 4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound O=C1N(C)C=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 QMTOOVLTKNHAJE-UHFFFAOYSA-N 0.000 description 1
GSHLTHMKMFRVPC-UHFFFAOYSA-N 4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-propylpyridin-2-one Chemical compound O=C1N(CCC)C=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 GSHLTHMKMFRVPC-UHFFFAOYSA-N 0.000 description 1
NDPJGYPMDCWPEU-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(1,2,2,2-tetrafluoroethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(C(F)C(F)(F)F)C(=O)C=1 NDPJGYPMDCWPEU-UHFFFAOYSA-N 0.000 description 1
GKWBDNNQADHVNR-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(1-phenylethyl)pyridin-2-one Chemical compound NC1=NC=C(C(=N1)C=1OC=CC=1)C1=CC(N(C=C1)C(C)C1=CC=CC=C1)=O GKWBDNNQADHVNR-UHFFFAOYSA-N 0.000 description 1
SMIJDRKGVXYUAY-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2,2,2-trifluoroethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CC(F)(F)F)C(=O)C=1 SMIJDRKGVXYUAY-UHFFFAOYSA-N 0.000 description 1
KCABQSNMQQMTGJ-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2,2-difluoroethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CC(F)F)C(=O)C=1 KCABQSNMQQMTGJ-UHFFFAOYSA-N 0.000 description 1
QHMMAIBPIYOKGC-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-ethoxyethyl)pyridin-2-one Chemical compound O=C1N(CCOCC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 QHMMAIBPIYOKGC-UHFFFAOYSA-N 0.000 description 1
IXNSIBBALHUMOV-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-fluoroethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CCF)C(=O)C=1 IXNSIBBALHUMOV-UHFFFAOYSA-N 0.000 description 1
KWCRZDYNAQEWKS-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methoxyethyl)pyridin-2-one Chemical compound O=C1N(CCOC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 KWCRZDYNAQEWKS-UHFFFAOYSA-N 0.000 description 1
LWRSAHMIXPQADV-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methylpropyl)pyridin-2-one Chemical compound O=C1N(CC(C)C)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 LWRSAHMIXPQADV-UHFFFAOYSA-N 0.000 description 1
IHVTWOYRRLKBER-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(3-fluoropropyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CCCF)C(=O)C=1 IHVTWOYRRLKBER-UHFFFAOYSA-N 0.000 description 1
MDARWOJIKYETNG-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(3-methylbut-2-enyl)pyridin-2-one Chemical compound O=C1N(CC=C(C)C)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 MDARWOJIKYETNG-UHFFFAOYSA-N 0.000 description 1
WGSAZXUIQAZGTR-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(3-methylbutyl)pyridin-2-one Chemical compound O=C1N(CCC(C)C)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 WGSAZXUIQAZGTR-UHFFFAOYSA-N 0.000 description 1
GWPARMGPJZQASY-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(3-phenylpropyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CCCC1=CC=CC=C1 GWPARMGPJZQASY-UHFFFAOYSA-N 0.000 description 1
YTIZOYGTAJBFGB-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(4,4,4-trifluorobutyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CCCC(F)(F)F)C(=O)C=1 YTIZOYGTAJBFGB-UHFFFAOYSA-N 0.000 description 1
ATZXIQXMOSHETD-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(4-methylpent-3-enyl)pyridin-2-one Chemical compound O=C1N(CCC=C(C)C)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 ATZXIQXMOSHETD-UHFFFAOYSA-N 0.000 description 1
GTYAANNIZDFROE-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(cyclobutylmethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1CCC1 GTYAANNIZDFROE-UHFFFAOYSA-N 0.000 description 1
SLMNFMFWNIDLID-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(pyridin-2-ylmethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=CC=N1 SLMNFMFWNIDLID-UHFFFAOYSA-N 0.000 description 1
JVDZJYRIUUSBMU-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(pyridin-3-ylmethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=CN=C1 JVDZJYRIUUSBMU-UHFFFAOYSA-N 0.000 description 1
JJQOOYPSCOODEA-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(pyridin-4-ylmethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=NC=C1 JJQOOYPSCOODEA-UHFFFAOYSA-N 0.000 description 1
YOQNJBULZCWPJB-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[(2,4-difluorophenyl)methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=C(F)C=C1F YOQNJBULZCWPJB-UHFFFAOYSA-N 0.000 description 1
YAWASTQWEUNBSI-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[(2,5-difluorophenyl)methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC(F)=CC=C1F YAWASTQWEUNBSI-UHFFFAOYSA-N 0.000 description 1
AKJCSMMASALPMM-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[(2-fluorophenyl)methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=CC=C1F AKJCSMMASALPMM-UHFFFAOYSA-N 0.000 description 1
AHZCETADZDDCOS-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[(3-fluorophenyl)methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=CC(F)=C1 AHZCETADZDDCOS-UHFFFAOYSA-N 0.000 description 1
FJLSZASVALGTSX-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[(4-fluorophenyl)methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=C(F)C=C1 FJLSZASVALGTSX-UHFFFAOYSA-N 0.000 description 1
KULBYZLOSDIHTI-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[(6-chloropyridin-3-yl)methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=C(Cl)N=C1 KULBYZLOSDIHTI-UHFFFAOYSA-N 0.000 description 1
FJDBHZRIZDUWBP-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[2-(diethylamino)ethyl]pyridin-2-one Chemical compound O=C1N(CCN(CC)CC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 FJDBHZRIZDUWBP-UHFFFAOYSA-N 0.000 description 1
TVRKOQVUQZVTGK-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[[3-(trifluoromethyl)phenyl]methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=CC(C(F)(F)F)=C1 TVRKOQVUQZVTGK-UHFFFAOYSA-N 0.000 description 1
XMKLAOFXOMSPTB-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=C(C(F)(F)F)C=C1 XMKLAOFXOMSPTB-UHFFFAOYSA-N 0.000 description 1
CVJULYYCCRQTLC-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-benzylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=CC1=O)C=CN1CC1=CC=CC=C1 CVJULYYCCRQTLC-UHFFFAOYSA-N 0.000 description 1
UZMMPKPVKUOCHK-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-but-2-ynylpyridin-2-one Chemical compound O=C1N(CC#CC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 UZMMPKPVKUOCHK-UHFFFAOYSA-N 0.000 description 1
JGTQSMWKDHRLDQ-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-but-3-enylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CCC=C)C(=O)C=1 JGTQSMWKDHRLDQ-UHFFFAOYSA-N 0.000 description 1
KETOEAABZAVRCA-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-ethylpyridin-2-one Chemical compound O=C1N(CC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 KETOEAABZAVRCA-UHFFFAOYSA-N 0.000 description 1
KKMUUHZUDKVWAH-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound O=C1N(C)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 KKMUUHZUDKVWAH-UHFFFAOYSA-N 0.000 description 1
JRVIELNMBITILU-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-pent-2-enylpyridin-2-one Chemical compound O=C1N(CC=CCC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 JRVIELNMBITILU-UHFFFAOYSA-N 0.000 description 1
LTFNUTSDORNTTH-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-pent-2-ynylpyridin-2-one Chemical compound O=C1N(CC#CCC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 LTFNUTSDORNTTH-UHFFFAOYSA-N 0.000 description 1
XRSAPSDOXVJZEN-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-prop-2-ynylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CC#C)C(=O)C=1 XRSAPSDOXVJZEN-UHFFFAOYSA-N 0.000 description 1
UOKYPPGWGGAMKT-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-propylpyridin-2-one Chemical compound O=C1N(CCC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 UOKYPPGWGGAMKT-UHFFFAOYSA-N 0.000 description 1
AJZMVSNBOZZRKT-UHFFFAOYSA-N 4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 AJZMVSNBOZZRKT-UHFFFAOYSA-N 0.000 description 1
FZNFEJXXRFISLV-UHFFFAOYSA-N 4-[4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]butanenitrile Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CCCC#N)C(=O)C=1 FZNFEJXXRFISLV-UHFFFAOYSA-N 0.000 description 1
QHSXEYVTXNQWIJ-UHFFFAOYSA-N 4-[4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]butanoic acid Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CCCC(O)=O)C(=O)C=1 QHSXEYVTXNQWIJ-UHFFFAOYSA-N 0.000 description 1
VOURUVNNLVCGQL-UHFFFAOYSA-N 4-[5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]butanoic acid Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCCC(O)=O)C=1 VOURUVNNLVCGQL-UHFFFAOYSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
150000005717 4-chloropyrimidines Chemical class 0.000 description 1
JUFZIWQDTJYWRX-UHFFFAOYSA-N 4-ethoxy-6-(3-fluorophenyl)-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(OCC)=NC(N)=NC=1C1=CC=CC(F)=C1 JUFZIWQDTJYWRX-UHFFFAOYSA-N 0.000 description 1
RXJWFJAMXKFVHE-UHFFFAOYSA-N 4-ethoxy-6-(furan-2-yl)-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC=CC=1C=1C(OCC)=NC(N)=NC=1C1=CC=CO1 RXJWFJAMXKFVHE-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
SFTRIKBTQFZXKL-UHFFFAOYSA-N 5-(2-amino-4-phenylpyrimidin-5-yl)-1h-pyridin-2-one Chemical compound C=1C=CC=CC=1C1=NC(N)=NC=C1C=1C=CC(=O)NC=1 SFTRIKBTQFZXKL-UHFFFAOYSA-N 0.000 description 1
TZOHERYYZOKPBY-UHFFFAOYSA-N 5-(2-aminopyridin-4-yl)-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C1=NC(N)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 TZOHERYYZOKPBY-UHFFFAOYSA-N 0.000 description 1
WWCKAAQMYJEJDL-UHFFFAOYSA-N 5-(2-bromopyridin-4-yl)-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C=1C=NC(Br)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 WWCKAAQMYJEJDL-UHFFFAOYSA-N 0.000 description 1
IIEZZTFUIUKQLU-UHFFFAOYSA-N 5-(2-butoxypyridin-4-yl)-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C1=NC(OCCCC)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 IIEZZTFUIUKQLU-UHFFFAOYSA-N 0.000 description 1
UXPXQSWKWHQUCB-UHFFFAOYSA-N 5-(furan-2-yl)-1h-indole Chemical compound C1=COC(C=2C=C3C=CNC3=CC=2)=C1 UXPXQSWKWHQUCB-UHFFFAOYSA-N 0.000 description 1
IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
AREKATGNVBEYRB-UHFFFAOYSA-N 5-[2-(benzylamino)pyridin-4-yl]-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C=1C=NC(NCC=2C=CC=CC=2)=CC=1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 AREKATGNVBEYRB-UHFFFAOYSA-N 0.000 description 1
GWSOUFDBNYRBEH-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 GWSOUFDBNYRBEH-UHFFFAOYSA-N 0.000 description 1
FWPCOVMLWWPBRF-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-4-(furan-2-yl)-6-phenylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2C=CC=CC=2)=C1 FWPCOVMLWWPBRF-UHFFFAOYSA-N 0.000 description 1
BPYZHHOHGUBVHP-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-4-(furan-2-yl)-6-pyridin-2-ylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2N=CC=CC=2)=C1 BPYZHHOHGUBVHP-UHFFFAOYSA-N 0.000 description 1
BTFNWXZGKBBIME-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-4-(furan-2-yl)-6-pyridin-3-ylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2C=NC=CC=2)=C1 BTFNWXZGKBBIME-UHFFFAOYSA-N 0.000 description 1
GOHWUBLCKVGJLR-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-4-(furan-2-yl)-6-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2C=CN=CC=2)=C1 GOHWUBLCKVGJLR-UHFFFAOYSA-N 0.000 description 1
JJVCLLLOADBUNP-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-4-(furan-2-yl)-6-thiophen-2-ylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2SC=CC=2)=C1 JJVCLLLOADBUNP-UHFFFAOYSA-N 0.000 description 1
GNAXARJKMSDSRN-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-4-(furan-2-yl)-6-thiophen-3-ylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2C(=NC(N)=NC=2C2=CSC=C2)C=2OC=CC=2)=C1 GNAXARJKMSDSRN-UHFFFAOYSA-N 0.000 description 1
TYUIVHAJLYSLIZ-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-(2-fluoroethyl)pyridin-2-one Chemical compound C1=CC(=O)N(CCF)C=C1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 TYUIVHAJLYSLIZ-UHFFFAOYSA-N 0.000 description 1
XRXDAUDLHUAIJJ-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-(3-hydroxypropyl)pyridin-2-one Chemical compound C1=CC(=O)N(CCCO)C=C1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 XRXDAUDLHUAIJJ-UHFFFAOYSA-N 0.000 description 1
RTXCLKYNNHPUDE-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-but-2-ynylpyridin-2-one Chemical compound C1=CC(=O)N(CC#CC)C=C1C1=C(C=2OC=CC=2)N=C(N)N=C1C1=CC=CO1 RTXCLKYNNHPUDE-UHFFFAOYSA-N 0.000 description 1
PRLXTJRJKASDHH-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-butylpyridin-2-one Chemical compound C1=CC(=O)N(CCCC)C=C1C1=C(C=2OC=CC=2)N=C(N)N=C1C1=CC=CO1 PRLXTJRJKASDHH-UHFFFAOYSA-N 0.000 description 1
ZYEVPWHWTNURFE-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-ethylpyridin-2-one Chemical compound C1=CC(=O)N(CC)C=C1C1=C(C=2OC=CC=2)N=C(N)N=C1C1=CC=CO1 ZYEVPWHWTNURFE-UHFFFAOYSA-N 0.000 description 1
QSLTVOLBJIKNPX-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-prop-2-enylpyridin-2-one Chemical compound C1=CC(=O)N(CC=C)C=C1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 QSLTVOLBJIKNPX-UHFFFAOYSA-N 0.000 description 1
XQXSXNGGXASSPB-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-propylpyridin-2-one Chemical compound C1=CC(=O)N(CCC)C=C1C1=C(C=2OC=CC=2)N=C(N)N=C1C1=CC=CO1 XQXSXNGGXASSPB-UHFFFAOYSA-N 0.000 description 1
RVYDWJTXPCBOAA-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-hydroxyethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCO)C=1 RVYDWJTXPCBOAA-UHFFFAOYSA-N 0.000 description 1
JGNIOSOZBWBDNF-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methylbutyl)pyridin-2-one Chemical compound C1=CC(=O)N(CC(C)CC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 JGNIOSOZBWBDNF-UHFFFAOYSA-N 0.000 description 1
KYNCNCBZTFLYOE-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methylpropyl)pyridin-2-one Chemical compound C1=CC(=O)N(CC(C)C)C=C1C1=CN=C(N)N=C1C1=CC=CO1 KYNCNCBZTFLYOE-UHFFFAOYSA-N 0.000 description 1
INNCIQWLGZENAG-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-pyrrol-1-ylethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1CCN1C=CC=C1 INNCIQWLGZENAG-UHFFFAOYSA-N 0.000 description 1
SUWRTGZCPNRRNT-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(3-fluoropropyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCCF)C=1 SUWRTGZCPNRRNT-UHFFFAOYSA-N 0.000 description 1
UXRXNYYIFUYBDH-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(3-hydroxypropyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCCO)C=1 UXRXNYYIFUYBDH-UHFFFAOYSA-N 0.000 description 1
BQTRRZGDIOFLSV-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(3-methylbutyl)pyridin-2-one Chemical compound C1=CC(=O)N(CCC(C)C)C=C1C1=CN=C(N)N=C1C1=CC=CO1 BQTRRZGDIOFLSV-UHFFFAOYSA-N 0.000 description 1
NRGBSOHCMBMEFT-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(8-hydroxyoctyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCCCCCCCO)C=1 NRGBSOHCMBMEFT-UHFFFAOYSA-N 0.000 description 1
LUZJFQGHSTXKSW-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(cyclopropylmethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1CC1CC1 LUZJFQGHSTXKSW-UHFFFAOYSA-N 0.000 description 1
GVEIDADVIWLEOD-ZHACJKMWSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-[(e)-2-phenylethenyl]pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1\C=C\C1=CC=CC=C1 GVEIDADVIWLEOD-ZHACJKMWSA-N 0.000 description 1
LFOIYKKLYCWEDX-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-benzylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1CC1=CC=CC=C1 LFOIYKKLYCWEDX-UHFFFAOYSA-N 0.000 description 1
BGTCRLXRVMWNHK-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-but-2-ynylpyridin-2-one Chemical compound C1=CC(=O)N(CC#CC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 BGTCRLXRVMWNHK-UHFFFAOYSA-N 0.000 description 1
ATICPJFEAHNMIV-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-butylpyridin-2-one Chemical compound C1=CC(=O)N(CCCC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 ATICPJFEAHNMIV-UHFFFAOYSA-N 0.000 description 1
HVWYNEQNUCTRPO-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-octylpyridin-2-one Chemical compound C1=CC(=O)N(CCCCCCCC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 HVWYNEQNUCTRPO-UHFFFAOYSA-N 0.000 description 1
VDJXKHTYYZTVPW-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-phenylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1C1=CC=CC=C1 VDJXKHTYYZTVPW-UHFFFAOYSA-N 0.000 description 1
JFEMJYOJBPMBDJ-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-prop-2-ynylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CC#C)C=1 JFEMJYOJBPMBDJ-UHFFFAOYSA-N 0.000 description 1
GRXAPIRVVPQJFA-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-propylpyridin-2-one Chemical compound C1=CC(=O)N(CCC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 GRXAPIRVVPQJFA-UHFFFAOYSA-N 0.000 description 1
DBXFDAXWDDLGBR-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-thiophen-3-ylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1C=1C=CSC=1 DBXFDAXWDDLGBR-UHFFFAOYSA-N 0.000 description 1
XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 1
ZDPHSSVKWDENDQ-UHFFFAOYSA-N 7-[4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]heptanenitrile Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CN(CCCCCCC#N)C(=O)C=1 ZDPHSSVKWDENDQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
GMXIEASXPUEOTG-UHFFFAOYSA-N 8-bromooctan-1-ol Chemical compound OCCCCCCCCBr GMXIEASXPUEOTG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
108010060263 Adenosine A1 Receptor Proteins 0.000 description 1
102000030814 Adenosine A1 receptor Human genes 0.000 description 1
108010060261 Adenosine A3 Receptor Proteins 0.000 description 1
102000008161 Adenosine A3 Receptor Human genes 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
PAOANWZGLPPROA-RQXXJAGISA-N CGS-21680 Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(NCCC=3C=CC(CCC(O)=O)=CC=3)=NC(N)=C2N=C1 PAOANWZGLPPROA-RQXXJAGISA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
229940123150 Chelating agent Drugs 0.000 description 1
244000223760 Cinnamomum zeylanicum Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
230000006820 DNA synthesis Effects 0.000 description 1
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
101001065501 Escherichia phage MS2 Lysis protein Proteins 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
101000783756 Homo sapiens Adenosine receptor A2b Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
208000015592 Involuntary movements Diseases 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
102000004257 Potassium Channel Human genes 0.000 description 1
KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
239000005700 Putrescine Substances 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229940121359 adenosine receptor antagonist Drugs 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229940087168 alpha tocopherol Drugs 0.000 description 1
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
229940127088 antihypertensive drug Drugs 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
229960001777 castor oil Drugs 0.000 description 1
230000024245 cell differentiation Effects 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
229940082500 cetostearyl alcohol Drugs 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
229960002242 chlorocresol Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
239000002734 clay mineral Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
229940013361 cresol Drugs 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000034994 death Effects 0.000 description 1
230000013872 defecation Effects 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
BTFSVBAFIHSVBO-UHFFFAOYSA-N dichloromethane;1,4-dioxane Chemical compound ClCCl.C1COCCO1 BTFSVBAFIHSVBO-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
229960000735 docosanol Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000005553 drilling Methods 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000009509 drug development Methods 0.000 description 1
239000003221 ear drop Substances 0.000 description 1
229940047652 ear drops Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
QROMFHQEJKRSPA-JLHYYAGUSA-N ethyl (e)-3-(furan-2-yl)-2-pyridin-4-ylprop-2-enoate Chemical compound C=1C=NC=CC=1/C(C(=O)OCC)=C\C1=CC=CO1 QROMFHQEJKRSPA-JLHYYAGUSA-N 0.000 description 1
QVLJLWHOILVHJJ-UHFFFAOYSA-N ethyl 2-pyridin-4-ylacetate Chemical compound CCOC(=O)CC1=CC=NC=C1 QVLJLWHOILVHJJ-UHFFFAOYSA-N 0.000 description 1
ILDJJTQWIZLGPO-UHFFFAOYSA-N ethyl 6-chloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(Cl)N=C1 ILDJJTQWIZLGPO-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000003885 eye ointment Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229960004198 guanidine Drugs 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
210000002216 heart Anatomy 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
102000055126 human ADORA2B Human genes 0.000 description 1
239000003906 humectant Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229940071676 hydroxypropylcellulose Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000004941 influx Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000005921 isopentoxy group Chemical group 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000003410 keratolytic agent Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000006138 lithiation reaction Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
230000004807 localization Effects 0.000 description 1
230000033001 locomotion Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XVTVRHMPTUWPFX-UHFFFAOYSA-N methyl 2-[4-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]acetate Chemical compound O=C1N(CC(=O)OC)C=CC(C=2C(=NC(N)=NC=2)C=2OC=CC=2)=C1 XVTVRHMPTUWPFX-UHFFFAOYSA-N 0.000 description 1
AMSAIXVOXLKTJV-UHFFFAOYSA-N methyl 4-[5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]butanoate Chemical compound C1=CC(=O)N(CCCC(=O)OC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 AMSAIXVOXLKTJV-UHFFFAOYSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007659 motor function Effects 0.000 description 1
230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 1
JBIGOIFYUUUTEE-UHFFFAOYSA-N n'-[4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]pyridin-2-yl]butane-1,4-diamine Chemical compound C1=NC(NCCCCN)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 JBIGOIFYUUUTEE-UHFFFAOYSA-N 0.000 description 1
UKSUALOBQZVRCE-UHFFFAOYSA-N n'-[4-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]pyridin-2-yl]ethane-1,2-diamine Chemical compound C1=NC(NCCN)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 UKSUALOBQZVRCE-UHFFFAOYSA-N 0.000 description 1
JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
235000005152 nicotinamide Nutrition 0.000 description 1
239000011570 nicotinamide Substances 0.000 description 1
229960003966 nicotinamide Drugs 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
210000001009 nucleus accumben Anatomy 0.000 description 1
229940073665 octyldodecyl myristate Drugs 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
210000001010 olfactory tubercle Anatomy 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920001289 polyvinyl ether Polymers 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
108020001213 potassium channel Proteins 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
229940032094 squalane Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000002636 symptomatic treatment Methods 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003760 tallow Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
KQPIFPBKXYBDGV-UHFFFAOYSA-M triethylstannanylium;bromide Chemical compound CC[Sn](Br)(CC)CC KQPIFPBKXYBDGV-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Obesity (AREA)
Physical Education & Sports Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Epidemiology (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Pulmonology (AREA)
Endocrinology (AREA)
Psychology (AREA)
Ophthalmology & Optometry (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO20041580A 2001-10-22 2004-04-19 Pyrimidinforbindelse, farmasoytisk preparat omfattende denne, og anvendelser av forbindelsen. NO327581B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2001324018		2001-10-22
PCT/JP2002/010952 WO2003035639A1 (fr)	2001-10-22	2002-10-22	Compose de pyrimidine et composition medicinale contenant ledit compose

Publications (2)

Publication Number	Publication Date
NO20041580L NO20041580L (no)	2004-07-22
NO327581B1 true NO327581B1 (no)	2009-08-24

Family

ID=19140824

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20041580A NO327581B1 (no)	2001-10-22	2004-04-19	Pyrimidinforbindelse, farmasoytisk preparat omfattende denne, og anvendelser av forbindelsen.

Country Status (24)

Country	Link
US (2)	US7396836B2 (zh)
EP (2)	EP2246344A1 (zh)
JP (1)	JP4462930B2 (zh)
KR (1)	KR100884025B1 (zh)
CN (1)	CN100519549C (zh)
AT (1)	ATE507217T1 (zh)
AU (1)	AU2002335536B2 (zh)
BR (1)	BR0213455A (zh)
CA (1)	CA2463284C (zh)
CY (1)	CY1112341T1 (zh)
DE (1)	DE60239884D1 (zh)
DK (1)	DK1439175T3 (zh)
ES (1)	ES2364328T3 (zh)
HU (1)	HUP0401950A3 (zh)
IL (2)	IL161493A0 (zh)
MX (1)	MXPA04003795A (zh)
NO (1)	NO327581B1 (zh)
NZ (1)	NZ532373A (zh)
PL (1)	PL215572B1 (zh)
PT (1)	PT1439175E (zh)
RU (1)	RU2288227C2 (zh)
TW (1)	TWI330183B (zh)
WO (1)	WO2003035639A1 (zh)
ZA (1)	ZA200402898B (zh)

Families Citing this family (114)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI330183B (zh) *	2001-10-22	2010-09-11	Eisai R&D Man Co Ltd
AU2002950853A0 (en) *	2002-08-19	2002-09-12	Fujisawa Pharmaceutical Co., Ltd.	Aminopyrimidine compound and pharmaceutical use thereof
ES2229928B1 (es) *	2003-10-02	2006-07-01	Almirall Prodesfarma, S.A.	Nuevos derivados de pirimidin-2-amina.
GB0323137D0 (en)	2003-10-03	2003-11-05	Chang Lisa C W	2,4,6- Trisubstituted pyrimidines and their different uses
GB0323138D0 (en) *	2003-10-03	2003-11-05	Chang Lisa C W	Pyrimidines substituted in the 2,4,6 positions and their different uses
WO2005040135A1 (ja) *	2003-10-24	2005-05-06	Ono Pharmaceutical Co., Ltd.	抗ストレス薬およびその医薬用途
JP4650419B2 (ja) *	2003-10-27	2011-03-16	アステラス製薬株式会社	ピラジン誘導体およびその医薬的使用
UA83101C2 (en) *	2003-12-15	2008-06-10	Алмирал Аг	2,6-bisheteroaryl-4-aminopyrimidines as adenosine receptor antagonists
EP3002283B1 (en)	2003-12-26	2017-06-14	Kyowa Hakko Kirin Co., Ltd.	Thiazole derivatives
US20080125403A1 (en)	2004-04-02	2008-05-29	Merck & Co., Inc.	Method of Treating Men with Metabolic and Anthropometric Disorders
EP2522670A1 (en)	2004-04-07	2012-11-14	Takeda Pharmaceutical Company Limited	Heterocyclic CRF receptor antagonists
GB2416125A (en) *	2004-07-15	2006-01-18	Michael James Hill	Device for supplying fluid to an ear
EP1831225A2 (en) *	2004-11-19	2007-09-12	The Regents of the University of California	Anti-inflammatory pyrazolopyrimidines
GB0428514D0 (en) *	2004-12-31	2005-02-09	Prosidion Ltd	Compounds
US7396928B2 (en)	2005-03-21	2008-07-08	Eisai R&D Management Co., Ltd.	Crystals of 5-[2-amino-4-(2-furyl) pyrimidin-5-yl]-1-methylpyridin-2(1H)-one and processes for preparing the same
US7538117B2 (en)	2005-03-21	2009-05-26	Eisai R&D Management Co., Ltd.	Crystalline and amorphous pyrimidine compounds and processes for preparing pyrimidine compounds
CN101928282B (zh) *	2005-03-21	2012-02-29	卫材R&D管理有限公司	嘧啶化合物的制备方法
EP1888565B1 (en) *	2005-04-11	2011-03-23	Almirall, S.A.	2, 6-di (hetero) aryl -4-amido-pyrimidines as adenosine receptor antagonists
AP2007004244A0 (en)	2005-05-10	2007-12-31	Intermune Inc	Method of modulating stress-activated protein kinase system
US20100280023A1 (en)	2005-06-23	2010-11-04	Kyowa Hakko Kogyo Co., Ltd.	Thiazole derivatives
ES2270715B1 (es) *	2005-07-29	2008-04-01	Laboratorios Almirall S.A.	Nuevos derivados de pirazina.
SI1921077T1 (sl)	2005-08-02	2017-11-30	Kyowa Hakko Kirin Co., Ltd.	Sredstvo za zdravljenje in/ali preprečevanje motnje spanja
ES2274712B1 (es) *	2005-10-06	2008-03-01	Laboratorios Almirall S.A.	Nuevos derivados imidazopiridina.
AU2007221049A1 (en) *	2006-02-28	2007-09-07	Amgen Inc.	Cinnoline and quinazoline derivates as phosphodiesterase 10 inhibitors
TWI417095B (zh)	2006-03-15	2013-12-01	Janssen Pharmaceuticals Inc	１，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途
KR101499783B1 (ko) *	2006-04-04	2015-03-09	더 리젠트스 오브 더 유니이버시티 오브 캘리포니아	키나제 길항물질
US20080009623A1 (en) *	2006-07-06	2008-01-10	Eisai R&D Management Co., Ltd.	Pyrimidine compounds
JP2009286694A (ja) *	2006-09-07	2009-12-10	Eisai R & D Management Co Ltd	５−［２−アミノ−４−（２−フリル）ピリミジン−５−イル］−１−メチルピリジン−２（１ｈ）−オンの塩およびそれらの結晶
ES2303776B1 (es) *	2006-12-29	2009-08-07	Laboratorios Almirall S.A.	Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b.
TW200900065A (en)	2007-03-07	2009-01-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives
TW200845978A (en)	2007-03-07	2008-12-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
MX2010001020A (es) *	2007-07-26	2010-03-01	Novartis Ag	Derivados de pirimidina utiles para el tratamiento de condiciones inflamatorias o alergicas.
CN103342695B (zh)	2007-09-14	2015-04-22	杨森制药有限公司	1’,3’-二取代的-4-苯基-3,4,5,6-四氢-2h,1’h-[1,4’]二吡啶-2’-酮
GB2467670B (en)	2007-10-04	2012-08-01	Intellikine Inc	Chemical entities and therapeutic uses thereof
NZ587004A (en)	2008-01-04	2013-11-29	Intellikine Llc	Heterocyclic containing entities, compositions and methods
US8193182B2 (en)	2008-01-04	2012-06-05	Intellikine, Inc.	Substituted isoquinolin-1(2H)-ones, and methods of use thereof
US8993580B2 (en)	2008-03-14	2015-03-31	Intellikine Llc	Benzothiazole kinase inhibitors and methods of use
US8637542B2 (en) *	2008-03-14	2014-01-28	Intellikine, Inc.	Kinase inhibitors and methods of use
WO2009118759A2 (en)	2008-03-26	2009-10-01	Advinus Therapeutics Pvt. Ltd.,	Heterocyclic compounds as adenosine receptor antagonist
CA3034994A1 (en)	2008-06-03	2009-12-10	Intermune, Inc.	Substituted aryl-2 pyridone compounds and use thereof for treating inflammatory and fibrotic disorders
CN101343253B (zh) *	2008-06-24	2011-03-16	陕西师范大学	2-氨基-4,5-二芳基嘧啶类化合物及其制备方法和药物用途
CN102124009B (zh) *	2008-07-08	2014-07-23	因特利凯公司	激酶抑制剂及其使用方法
US20110224223A1 (en) *	2008-07-08	2011-09-15	The Regents Of The University Of California, A California Corporation	MTOR Modulators and Uses Thereof
MX2011002042A (es)	2008-09-02	2011-06-20	Ortho Mcneil Janssen Pharm	Derivados de 3-azabiciclo[3.1.o]hexilo como moduladores de los receptores del glutamato metabotropico.
WO2010036380A1 (en)	2008-09-26	2010-04-01	Intellikine, Inc.	Heterocyclic kinase inhibitors
CA2740885C (en)	2008-10-16	2018-04-03	The Regents Of The University Of California	Fused ring heteroaryl kinase inhibitors
US8476431B2 (en)	2008-11-03	2013-07-02	Itellikine LLC	Benzoxazole kinase inhibitors and methods of use
JP5690277B2 (ja)	2008-11-28	2015-03-25	ジャンセンファーマシューティカルズ，インコーポレイテッド．	代謝型グルタミン酸受容体の調節因子としてのインドールおよびベンゾオキサジン誘導体
AU2010222289B2 (en)	2009-03-13	2013-07-11	Advinus Therapeutics Private Limited	Substituted fused pyrimidine compounds
JP5789252B2 (ja)	2009-05-07	2015-10-07	インテリカイン，エルエルシー	複素環式化合物およびその使用
ES2409006T3 (es)	2009-05-12	2013-06-24	Janssen Pharmaceuticals Inc.	Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de los receptores mGluR2
EP2430022B1 (en)	2009-05-12	2013-11-20	Janssen Pharmaceuticals, Inc.	1,2,4-Triazolo[4,3-a]pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders
MY153913A (en)	2009-05-12	2015-04-15	Janssen Pharmaceuticals Inc	7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
US8980899B2 (en)	2009-10-16	2015-03-17	The Regents Of The University Of California	Methods of inhibiting Ire1
EP2499142B1 (en)	2009-11-09	2016-09-21	Advinus Therapeutics Limited	Substituted fused pyrimidine compounds, its preparation and uses thereof
AU2011223976B2 (en)	2010-03-04	2015-05-21	Merck Sharp & Dohme Corp.	Inhibitors of catechol O-methyl transferase and their use in the treatment of psychotic disorders
ES2365960B1 (es) *	2010-03-31	2012-06-04	Palobiofarma, S.L	Nuevos antagonistas de los receptores de adenosina.
WO2011146882A1 (en)	2010-05-21	2011-11-24	Intellikine, Inc.	Chemical compounds, compositions and methods for kinase modulation
US20130156720A1 (en)	2010-08-27	2013-06-20	Ironwood Pharmaceuticals, Inc.	Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders
WO2012035548A1 (en)	2010-09-13	2012-03-22	Advinus Therapeutics Private Limited	Purine compounds as prodrugs of a2b adenosine receptor antagonists, their process and medicinal applications
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
WO2012039718A1 (en)	2010-09-24	2012-03-29	N30 Pharmaceuticals, Llc	Novel dihydropyrimidin-2(1h)-one compounds as neurokinin-3 receptor antagonists
ES2552455T3 (es)	2010-11-08	2015-11-30	Janssen Pharmaceuticals, Inc.	Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2
EP2643320B1 (en)	2010-11-08	2015-03-04	Janssen Pharmaceuticals, Inc.	1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
CN103298809B (zh)	2010-11-08	2016-08-31	杨森制药公司	1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途
CN103298474B (zh)	2010-11-10	2016-06-29	无限药品股份有限公司	杂环化合物及其用途
UA115767C2 (uk)	2011-01-10	2017-12-26	Інфініті Фармасьютікалз, Інк.	Способи отримання ізохінолінонів і тверді форми ізохінолінонів
WO2012148540A1 (en)	2011-02-23	2012-11-01	Intellikine, Llc	Combination of kanase inhibitors and uses threof
CZ305457B6 (cs) *	2011-02-28	2015-09-30	Ústav organické chemie a biochemie, Akademie věd ČR v. v. i.	Pyrimidinové sloučeniny inhibující tvorbu oxidu dusnatého a prostaglandinu E2, způsob výroby a použití
CN103946226A (zh)	2011-07-19	2014-07-23	无限药品股份有限公司	杂环化合物及其应用
JP6027610B2 (ja)	2011-07-19	2016-11-16	インフィニティーファーマシューティカルズ，インコーポレイテッド	複素環式化合物及びその使用
TW201311663A (zh)	2011-08-29	2013-03-16	Infinity Pharmaceuticals Inc	雜環化合物及其用途
WO2013077921A2 (en)	2011-09-02	2013-05-30	The Regents Of The University Of California	Substituted pyrazolo[3,4-d]pyrimidines and uses thereof
PT2820009T (pt)	2012-03-01	2018-04-12	Array Biopharma Inc	Inibidores de serina/treonina quinases
US8940742B2 (en)	2012-04-10	2015-01-27	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
US8828998B2 (en)	2012-06-25	2014-09-09	Infinity Pharmaceuticals, Inc.	Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors
JP2015532287A (ja)	2012-09-26	2015-11-09	ザ・リージエンツ・オブ・ザ・ユニバーシテイー・オブ・カリフオルニア	Ｉｒｅ１の調節
AR092742A1 (es)	2012-10-02	2015-04-29	Intermune Inc	Piridinonas antifibroticas
EP2922543B1 (en) *	2012-11-20	2017-05-24	Merck Sharp & Dohme Corp.	Substituted pyridone derivatives as pde10 inhibitors
KR101529496B1 (ko) *	2012-12-27	2015-06-22	한국과학기술원	낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드
US9481667B2 (en)	2013-03-15	2016-11-01	Infinity Pharmaceuticals, Inc.	Salts and solid forms of isoquinolinones and composition comprising and methods of using the same
JO3368B1 (ar)	2013-06-04	2019-03-13	Janssen Pharmaceutica Nv	مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2
AU2014274812B2 (en)	2013-06-05	2018-09-27	Bausch Health Ireland Limited	Ultra-pure agonists of guanylate cyclase C, method of making and using same
JO3367B1 (ar)	2013-09-06	2019-03-13	Janssen Pharmaceutica Nv	مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2
US9751888B2 (en)	2013-10-04	2017-09-05	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
CN105793255B (zh)	2013-10-04	2018-11-16	无限药品股份有限公司	杂环化合物及其用途
KR20200036063A (ko)	2014-01-21	2020-04-06	얀센 파마슈티카 엔.브이.	대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도
EA202192128A1 (ru)	2014-02-04	2022-02-28	Янссен Фармацевтика Нв	Комбинации, содержащие положительные аллостерические модуляторы или ортостерические агонисты метаботропного глутаматергического рецептора 2 подтипа, и их применение
WO2015120777A1 (zh) *	2014-02-14	2015-08-20	四川海思科制药有限公司	一种吡啶酮或嘧啶酮衍生物、及其制备方法和应用
AU2015231413B2 (en)	2014-03-19	2020-04-23	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds for use in the treatment of PI3K-gamma mediated disorders
CN110452216B (zh)	2014-04-02	2022-08-26	英特穆恩公司	抗纤维化吡啶酮类
WO2015160975A2 (en)	2014-04-16	2015-10-22	Infinity Pharmaceuticals, Inc.	Combination therapies
WO2016054491A1 (en)	2014-10-03	2016-04-07	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
CN114230571A (zh)	2015-09-14	2022-03-25	无限药品股份有限公司	异喹啉酮的固体形式、其制备方法、包含其的组合物及其使用方法
JP2017149663A (ja) *	2016-02-24	2017-08-31	株式会社Ｌｔｔバイオファーマ	過敏性腸症候群治療剤
WO2017161116A1 (en)	2016-03-17	2017-09-21	Infinity Pharmaceuticals, Inc.	Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors
US10919914B2 (en)	2016-06-08	2021-02-16	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
CA3028718A1 (en)	2016-06-24	2017-12-28	Infinity Pharmaceuticals, Inc.	Combination therapies
EP4310082A3 (en)	2017-01-20	2024-04-10	Arcus Biosciences, Inc.	Azolopyrimidine for the treatment of cancer-related disorders
EP3611174B1 (en) *	2017-04-07	2022-06-08	Medshine Discovery Inc.	[1,2,4]triazolo[1,5-c]pyrimidine derivative as a2a receptor inhibitor
JP7295034B2 (ja) *	2017-05-05	2023-06-20	アーカスバイオサイエンシズインコーポレイティド	癌関連障害の治療のためのキナゾリン－ピリジン誘導体
KR20200121337A (ko)	2018-02-16	2020-10-23	아르커스 바이오사이언시즈 인코포레이티드	아졸로피리미딘 화합물의 투여
CN110240593A (zh) *	2018-03-09	2019-09-17	四川科伦博泰生物医药股份有限公司	取代芳胺化合物及其制备方法和用途
CN108314631A (zh) *	2018-04-19	2018-07-24	中国科学院昆明植物研究所	二芳基乙烯类化合物及其药物组合物和其应用
CN110655509B (zh) *	2018-06-29	2023-01-24	江苏恒瑞医药股份有限公司	2-胺基嘧啶类衍生物、其制备方法及其在医药上的应用
CN110684020B (zh) *	2018-07-05	2023-01-20	江苏恒瑞医药股份有限公司	2-胺基嘧啶类衍生物、其制备方法及其在医药上的应用
EP3820474A4 (en) *	2018-07-10	2022-03-23	Nikang Therapeutics, Inc.	ADENOSINE RECEPTOR BINDING COMPOUNDS
CN111094254B (zh) *	2018-07-12	2022-07-26	江苏恒瑞医药股份有限公司	杂芳基类衍生物、其制备方法及其在医药上的应用
EP3904348A4 (en)	2018-12-28	2022-10-19	Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.	AMINOPYRIDINE COMPOUND, METHOD FOR PREPARATION AND USE
CN113166119B (zh) *	2018-12-28	2024-01-05	四川科伦博泰生物医药股份有限公司	取代芳基化合物及其制备方法和用途
CN111377873B (zh) *	2018-12-28	2023-03-28	四川科伦博泰生物医药股份有限公司	氨基嘧啶化合物及其制备方法和用途
US10689374B1 (en)	2019-07-12	2020-06-23	United Arab Emirates University	Pyrimidine-thiazolidinone derivatives
US10702525B1 (en)	2019-09-04	2020-07-07	United Arab Emirates University	Pyrimidine derivatives as anti-diabetic agents
WO2021185256A1 (zh) *	2020-03-16	2021-09-23	上海海雁医药科技有限公司	取代的嘧啶或吡啶胺衍生物、其组合物及医药上的用途

Family Cites Families (56)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3029426A1 (de) *	1980-08-02	1982-03-11	Bayer Ag, 5090 Leverkusen	Gegen zwecken wirksame pour-on-formulierungen
US4725600A (en) *	1984-07-13	1988-02-16	Fujisawa Pharmaceutical Co., Ltd.	Pyrimidine compounds having activity as a cardiotonic anti-hypertensive cerebrovascular vasodilator and anti-platelet aggregation agent
FR2584925B1 (fr) *	1985-07-17	1987-11-27	Bosserelle Micheline	Composition de corps gras d'origine vegetale pour usage cosmetique
US4927813A (en) *	1988-03-08	1990-05-22	Bernstein Joel E	Method and composition for treating pediculosis capitis
JPH0252360A (ja)	1988-08-15	1990-02-21	Fujitsu Ltd	電子写真感光体
PE5591A1 (es) *	1988-12-19	1991-02-15	Lilly Co Eli	Un nuevo grupo de compuestos de macrolida
US5362634A (en) *	1989-10-30	1994-11-08	Dowelanco	Process for producing A83543 compounds
US5288483A (en) *	1990-04-18	1994-02-22	The Procter & Gamble Company	Anti-lice treatment compositions
DD294255A5 (de)	1990-05-14	1991-09-26	Adw Forschungsstelle Fuer Chemische Toxikologie,De	Verfahren zur herstellung tetrazolylsubstituierter pyrimidinderivate
US5227163A (en) *	1991-01-18	1993-07-13	Clilco, Ltd.	Lice-repellant compositions
US5145684A (en) *	1991-01-25	1992-09-08	Sterling Drug Inc.	Surface modified drug nanoparticles
US5227295A (en) *	1991-11-08	1993-07-13	Dowelanco	Process for isolating A83543 and its components
US5539089A (en) *	1991-11-08	1996-07-23	Dowelanco	A83543 aglycones and pseudoglycones
US5202242A (en) *	1991-11-08	1993-04-13	Dowelanco	A83543 compounds and processes for production thereof
JP2613355B2 (ja)	1992-09-28	1997-05-28	協和醗酵工業株式会社	パーキンソン氏病治療剤
US5591606A (en) *	1992-11-06	1997-01-07	Dowelanco	Process for the production of A83543 compounds with Saccharopolyspora spinosa
ES2099604T3 (es) *	1993-03-12	1997-05-16	Dowelanco	Nuevos compuestos a83543 y procedimiento para su produccion.
US5795905A (en) *	1995-06-06	1998-08-18	Neurocrine Biosciences, Inc.	CRF receptor antagonists and methods relating thereto
US5935966A (en) *	1995-09-01	1999-08-10	Signal Pharmaceuticals, Inc.	Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions
WO1997033883A1 (en) *	1996-03-13	1997-09-18	Smithkline Beecham Corporation	Novel pyrimidine compounds useful in treating cytokine mediated diseases
US6010710A (en) *	1996-03-29	2000-01-04	Merial	Direct pour-on skin solution for antiparasitic use in cattle and sheep
US5952331A (en) *	1996-05-23	1999-09-14	Syntex (Usa) Inc.	Aryl pyrimidine derivatives
US6001981A (en) *	1996-06-13	1999-12-14	Dow Agrosciences Llc	Synthetic modification of Spinosyn compounds
FR2756177B1 (fr) *	1996-11-28	1999-01-29	Oreal	Dispersion aqueuse de vesicules resistantes a la deshydratation
EP0948497A2 (en) *	1996-12-05	1999-10-13	Amgen inc.	Substituted pyrimidine compounds and their use
US6096753A (en) *	1996-12-05	2000-08-01	Amgen Inc.	Substituted pyrimidinone and pyridone compounds and methods of use
TW520362B (en) *	1996-12-05	2003-02-11	Amgen Inc	Substituted pyrimidine compounds and pharmaceutical composition comprising same
BR9713863A (pt) *	1996-12-05	2000-03-14	Amgen Inc	Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, processos de profilaxia ou tratamento, para abaixar as concentrações no plasma, para diminuir a produção de prostaglandinas, e, para diminuir a atividade de enzima ciclooxigenase
US5880076A (en) *	1997-08-04	1999-03-09	Lever Brothers Company, Division Of Conopco, Inc.	Compositions comprising glycacarbamate and glycaurea compounds
US6096326A (en) *	1997-08-15	2000-08-01	Scandinavian-American Import/Export Corporation	Skin care compositions and use
JPH11188484A (ja)	1997-12-25	1999-07-13	Nkk Corp	多段研削バリ取り装置
AU1688599A (en) *	1998-01-05	1999-07-26	Eisai Co. Ltd.	Purine derivatives and adenosine a2 receptor antagonists serving as preventives/remedies for diabetes
JP3990061B2 (ja)	1998-01-05	2007-10-10	エーザイ・アール・アンド・ディー・マネジメント株式会社	プリン誘導体および糖尿病の予防・治療剤としてのアデノシンａ２受容体拮抗剤
US6235754B1 (en) *	1998-01-30	2001-05-22	American Cyanamid Company	Methods and compositions for protecting animals and humans against attack and infestation by arthropod and helminth parasites
DE19823397B4 (de) *	1998-05-26	2011-07-28	Bayer CropScience AG, 40789	Verwendung von Spinosynen zum Einsatz als Bodeninsektizide
EP1087963B1 (en) *	1998-06-19	2004-08-25	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
US7045519B2 (en)	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
IL140072A (en) *	1998-07-02	2005-12-18	Lilly Co Eli	Formulations for controlling lice in human
TWI241298B (en)	1998-09-25	2005-10-11	Mitsubishi Chem Corp	Pyrimidone derivatives
JP2000126489A (ja)	1998-10-21	2000-05-09	Purotonikusu Kenkyusho:Kk	糸又は布と接触するミシン用部品
PT1221444E (pt)	1999-07-02	2005-11-30	Eisai Co Ltd	Derivados de imidazole condensados e medicamentos para a diabetes mellitus
WO2001062233A2 (en) *	2000-02-25	2001-08-30	F. Hoffmann La Roche Ag	Adenosine receptor modulators
EP1136482A1 (en)	2000-03-23	2001-09-26	Sanofi-Synthelabo	2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors
EP1136486A1 (en)	2000-03-23	2001-09-26	Sanofi-Synthelabo	2-[Indanylamino]pyrimidone and 2-[tetrahydronaphthalenylamino]pyrimidone derivatives
AU2001248365A1 (en)	2000-03-23	2001-10-03	Mitsubishi Pharma Corporation	2-(arylalkylamino)pyrimidone derivatives and 2-(heteroarylalkylamino)pyrimidone derivatives
ATE284712T1 (de) *	2000-04-26	2005-01-15	Eisai Co Ltd	Medizinische zusammensetzungen zur förderung der aktivierung der eingeweide
EP1308441B1 (en)	2000-08-11	2009-10-07	Eisai R&D Management Co., Ltd.	2-aminopyridine compounds and use thereof as drugs
EP1317433A2 (en) *	2000-09-06	2003-06-11	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
PE20020451A1 (es)	2000-09-15	2002-06-06	Vertex Pharma	Compuestos de pirazol utiles como inhibidores de cinasa proteina
AU2001292906B2 (en) *	2000-09-19	2007-08-16	Novartis Vaccines And Diagnostics, Inc.	Characterization of the GSK-3beta protein and methods of use thereof
MY130778A (en) *	2001-02-09	2007-07-31	Vertex Pharma	Heterocyclic inhibitiors of erk2 and uses thereof
TWI301834B (en) *	2001-10-22	2008-10-11	Eisai R&D Man Co Ltd	Pyrimidone compound and pharmaceutical composition including the same
TWI330183B (zh)	2001-10-22	2010-09-11	Eisai R&D Man Co Ltd
AU2002950853A0 (en)	2002-08-19	2002-09-12	Fujisawa Pharmaceutical Co., Ltd.	Aminopyrimidine compound and pharmaceutical use thereof
US7396928B2 (en)	2005-03-21	2008-07-08	Eisai R&D Management Co., Ltd.	Crystals of 5-[2-amino-4-(2-furyl) pyrimidin-5-yl]-1-methylpyridin-2(1H)-one and processes for preparing the same
US7538117B2 (en)	2005-03-21	2009-05-26	Eisai R&D Management Co., Ltd.	Crystalline and amorphous pyrimidine compounds and processes for preparing pyrimidine compounds

2002
- 2002-10-21 TW TW091124227A patent/TWI330183B/zh not_active IP Right Cessation
- 2002-10-22 BR BR0213455-1A patent/BR0213455A/pt not_active IP Right Cessation
- 2002-10-22 AU AU2002335536A patent/AU2002335536B2/en not_active Ceased
- 2002-10-22 DE DE60239884T patent/DE60239884D1/de not_active Expired - Lifetime
- 2002-10-22 MX MXPA04003795A patent/MXPA04003795A/es active IP Right Grant
- 2002-10-22 WO PCT/JP2002/010952 patent/WO2003035639A1/ja active Application Filing
- 2002-10-22 CN CNB028209311A patent/CN100519549C/zh not_active Expired - Fee Related
- 2002-10-22 EP EP10173222A patent/EP2246344A1/en not_active Withdrawn
- 2002-10-22 PL PL370274A patent/PL215572B1/pl not_active IP Right Cessation
- 2002-10-22 NZ NZ532373A patent/NZ532373A/en not_active IP Right Cessation
- 2002-10-22 AT AT02802050T patent/ATE507217T1/de active
- 2002-10-22 JP JP2003538155A patent/JP4462930B2/ja not_active Expired - Fee Related
- 2002-10-22 CA CA2463284A patent/CA2463284C/en not_active Expired - Fee Related
- 2002-10-22 EP EP02802050A patent/EP1439175B1/en not_active Expired - Lifetime
- 2002-10-22 HU HU0401950A patent/HUP0401950A3/hu unknown
- 2002-10-22 DK DK02802050.1T patent/DK1439175T3/da active
- 2002-10-22 RU RU2004115495/04A patent/RU2288227C2/ru not_active IP Right Cessation
- 2002-10-22 KR KR1020047005915A patent/KR100884025B1/ko not_active IP Right Cessation
- 2002-10-22 PT PT02802050T patent/PT1439175E/pt unknown
- 2002-10-22 ES ES02802050T patent/ES2364328T3/es not_active Expired - Lifetime
- 2002-10-22 US US10/492,905 patent/US7396836B2/en not_active Expired - Fee Related
- 2002-10-22 IL IL16149302A patent/IL161493A0/xx unknown
2004
- 2004-04-16 ZA ZA200402898A patent/ZA200402898B/xx unknown
- 2004-04-19 IL IL161493A patent/IL161493A/en not_active IP Right Cessation
- 2004-04-19 NO NO20041580A patent/NO327581B1/no not_active IP Right Cessation
2008
- 2008-03-24 US US12/054,337 patent/US20090030023A1/en not_active Abandoned
2011
- 2011-07-11 CY CY20111100672T patent/CY1112341T1/el unknown

Also Published As

Publication number	Publication date
JP4462930B2 (ja)	2010-05-12
ATE507217T1 (de)	2011-05-15
TWI330183B (zh)	2010-09-11
KR20040053191A (ko)	2004-06-23
CA2463284A1 (en)	2003-05-01
WO2003035639A1 (fr)	2003-05-01
EP1439175A4 (en)	2004-12-29
CA2463284C (en)	2010-10-19
ZA200402898B (en)	2006-03-29
US20050004149A1 (en)	2005-01-06
EP1439175A1 (en)	2004-07-21
IL161493A0 (en)	2004-09-27
MXPA04003795A (es)	2004-07-30
ES2364328T3 (es)	2011-08-31
CN100519549C (zh)	2009-07-29
CN1575290A (zh)	2005-02-02
US20090030023A1 (en)	2009-01-29
HUP0401950A3 (en)	2010-06-28
NO20041580L (no)	2004-07-22
BR0213455A (pt)	2004-10-19
PL370274A1 (en)	2005-05-16
PL215572B1 (pl)	2013-12-31
AU2002335536B2 (en)	2008-11-13
RU2288227C2 (ru)	2006-11-27
HUP0401950A2 (hu)	2005-01-28
NZ532373A (en)	2007-02-23
RU2004115495A (ru)	2005-04-10
EP1439175B1 (en)	2011-04-27
JPWO2003035639A1 (ja)	2005-02-10
PT1439175E (pt)	2011-07-08
DK1439175T3 (da)	2011-07-18
IL161493A (en)	2010-04-29
KR100884025B1 (ko)	2009-02-17
EP2246344A1 (en)	2010-11-03
DE60239884D1 (de)	2011-06-09
CY1112341T1 (el)	2015-12-09
US7396836B2 (en)	2008-07-08

Publication	Publication Date	Title
NO327581B1 (no)	2009-08-24	Pyrimidinforbindelse, farmasoytisk preparat omfattende denne, og anvendelser av forbindelsen.
KR100694684B1 (ko)	2007-03-13	축합 이미다졸 화합물 및 당뇨병 치료약
US11352341B2 (en)	2022-06-07	2H-indazole derivatives as CDK4 and CDK6 inhibitors and therapeutic uses thereof
US7160892B2 (en)	2007-01-09	Pyrimidone compounds and pharmaceutical compositions containing the same
NO325873B1 (no)	2008-08-11	2-aminopyridinforbindelser, deres anvendelse samt farmasoytisk preparat
JP6200520B2 (ja)	2017-09-20	置換２−アミノピリジンプロテインキナーゼ阻害剤
US9181238B2 (en)	2015-11-10	N-(pyridin-2-yl)sulfonamides and compositions thereof as protein kinase inhibitors
EP3094325A1 (en)	2016-11-23	Heteroaryls and uses thereof
TW202313588A (zh)	2023-04-01	檢測點激酶１（ｃｈｋ１）抑制劑及其用途
PH12015502047B1 (en)	2016-01-18	Novel pyrimidine and pyridine compounds and their usage
KR20100136516A (ko)	2010-12-28	신규한 헤테로시클릭 화합물 및 그의 용도
TWI710554B (zh)	2020-11-21	新穎苯并咪唑化合物及其醫藥用途
WO2023230477A1 (en)	2023-11-30	Pyridine checkpoint kinase 1 (chk1) inhibitors and uses thereof
TW202317544A (zh)	2023-05-01	吡啶酮mk2抑制劑及其用途
CN115315422B (zh)	2023-11-07	酰胺类化合物及其用途
JP2022515309A (ja)	2022-02-18	置換アリール化合物、その製造方法及び用途
KR20150074157A (ko)	2015-07-01	Ttx-s 차단제로서의 피라졸로피리딘 유도체
CN108602834B (zh)	2021-01-08	一种布鲁顿酪氨酸激酶抑制剂
KR20240127910A (ko)	2024-08-23	Sos1 억제제 및 항암제를 포함하는 암 치료용 약학 조성물
CN117865939A (zh)	2024-04-12	氨基嘧啶类衍生物抑制剂、其制备方法和应用

Legal Events

Date	Code	Title	Description
2014-05-26	MM1K	Lapsed by not paying the annual fees