IL97501A - History of 4-pyridone. And pharmaceutical preparations containing them - Google Patents

History of 4-pyridone. And pharmaceutical preparations containing them

Info

Publication number: IL97501A
Authority: IL; Israel
Prior art keywords: group; phenyl; alkyl; optionally substituted; compound
Prior art date: 1990-03-12

Application number

IL9750191A

Other languages

English (en)

Hebrew (he)

Other versions

IL97501A0 (en

Original Assignee

Wellcome Found

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.)

1990-03-12

Filing date

1991-03-11

Publication date

1995-03-15

1991-03-11 Application filed by Wellcome Found filed Critical Wellcome Found

1992-06-21 Publication of IL97501A0 publication Critical patent/IL97501A0/xx

1995-03-15 Publication of IL97501A publication Critical patent/IL97501A/en

Links

238000002360 preparation method Methods 0.000 title claims description 30
239000008194 pharmaceutical composition Substances 0.000 title description 4
MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical class O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 128
-1 hydroxy, carboxy, amino Chemical group 0.000 claims abstract description 47
125000005843 halogen group Chemical group 0.000 claims abstract description 37
150000003839 salts Chemical class 0.000 claims abstract description 26
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 16
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
125000003118 aryl group Chemical group 0.000 claims abstract description 11
208000030852 Parasitic disease Diseases 0.000 claims abstract description 9
238000011282 treatment Methods 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
125000006413 ring segment Chemical group 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 72
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
238000009472 formulation Methods 0.000 claims description 33
238000000034 method Methods 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 18
230000001225 therapeutic effect Effects 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 9
241000282414 Homo sapiens Species 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 8
230000008569 process Effects 0.000 claims description 7
229940124597 therapeutic agent Drugs 0.000 claims description 6
208000015181 infectious disease Diseases 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
230000000865 phosphorylative effect Effects 0.000 claims description 4
125000005554 pyridyloxy group Chemical group 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
150000004340 hydroxynaphthoquinones Chemical group 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
CSFWPUWCSPOLJW-UHFFFAOYSA-N hydroxynaphthoquinone Natural products C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
LPCLQACEIMYBGP-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[4-[3-(trifluoromethyl)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 LPCLQACEIMYBGP-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
201000004792 malaria Diseases 0.000 abstract description 5
208000003495 Coccidiosis Diseases 0.000 abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
206010023076 Isosporiasis Diseases 0.000 abstract description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
208000005384 Pneumocystis Pneumonia Diseases 0.000 abstract 1
206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 abstract 1
201000000317 pneumocystosis Diseases 0.000 abstract 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
101150041968 CDC13 gene Proteins 0.000 description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
239000000725 suspension Substances 0.000 description 14
239000004480 active ingredient Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000007787 solid Substances 0.000 description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
229910052794 bromium Inorganic materials 0.000 description 11
230000000694 effects Effects 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002904 solvent Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000000969 carrier Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
238000001816 cooling Methods 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
230000003071 parasitic effect Effects 0.000 description 6
241000223960 Plasmodium falciparum Species 0.000 description 5
QCCDLTOVEPVEJK-UHFFFAOYSA-N benzyl methyl ketone Natural products CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 5
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 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
235000010265 sodium sulphite Nutrition 0.000 description 5
238000001665 trituration Methods 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
241000233872 Pneumocystis carinii Species 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
239000002585 base Substances 0.000 description 4
239000012267 brine Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000011630 iodine Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000000069 prophylactic effect Effects 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYMCXGILCMIOKD-UHFFFAOYSA-N (4-bromophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Br)C=C1 FYMCXGILCMIOKD-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
235000010980 cellulose Nutrition 0.000 description 3
239000003405 delayed action preparation Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000010255 intramuscular injection Methods 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
244000045947 parasite Species 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
241000894007 species Species 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
AHLLPGLCEKQVTB-UHFFFAOYSA-N 1-(4-chlorophenoxy)-4-(2-nitroprop-1-enyl)benzene Chemical compound C1=CC(C=C(C)[N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C=C1 AHLLPGLCEKQVTB-UHFFFAOYSA-N 0.000 description 2
MZMALMLQHQUVTN-UHFFFAOYSA-N 1-[4-(4-chlorophenoxy)phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OC1=CC=C(Cl)C=C1 MZMALMLQHQUVTN-UHFFFAOYSA-N 0.000 description 2
HEYNDJNBVFIFIT-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)sulfanylphenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1SC1=CC=C(Cl)C=C1 HEYNDJNBVFIFIT-UHFFFAOYSA-N 0.000 description 2
NJGAJAIBBXYKTN-UHFFFAOYSA-N 2,6-dimethyl-3-[4-(4-methylphenyl)sulfanylphenyl]pyran-4-one Chemical compound CC=1OC(=CC(C1C1=CC=C(C=C1)SC1=CC=C(C=C1)C)=O)C NJGAJAIBBXYKTN-UHFFFAOYSA-N 0.000 description 2
ZJFGVOFPOBTANE-UHFFFAOYSA-N 2,6-dimethyl-3-[4-[3-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound N1C(C)=CC(=O)C(C=2C=CC(OC=3C=C(OC(F)(F)F)C=CC=3)=CC=2)=C1C ZJFGVOFPOBTANE-UHFFFAOYSA-N 0.000 description 2
CUSWBVPEDCMBFW-UHFFFAOYSA-N 2,6-dimethyl-3-[4-[3-(trifluoromethoxy)phenoxy]phenyl]pyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(OC=3C=C(OC(F)(F)F)C=CC=3)=CC=2)=C1C CUSWBVPEDCMBFW-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
BOLZBUKPPORRCG-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 BOLZBUKPPORRCG-UHFFFAOYSA-N 0.000 description 2
BZRPOJGQEWLGMP-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 BZRPOJGQEWLGMP-UHFFFAOYSA-N 0.000 description 2
DWGQVNPYOUEJHQ-UHFFFAOYSA-N 3-iodo-2,6-dimethyl-5-octyl-1h-pyridin-4-one Chemical compound CCCCCCCCC1=C(C)NC(C)=C(I)C1=O DWGQVNPYOUEJHQ-UHFFFAOYSA-N 0.000 description 2
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
241000223924 Eimeria Species 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 2
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 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229930192627 Naphthoquinone Natural products 0.000 description 2
241000224016 Plasmodium Species 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
206010037075 Protozoal infections Diseases 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
239000012980 RPMI-1640 medium Substances 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000001165 anti-coccidial effect Effects 0.000 description 2
239000003430 antimalarial agent Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
239000000872 buffer Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
238000013270 controlled release Methods 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
229940079593 drug Drugs 0.000 description 2
210000003743 erythrocyte Anatomy 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
238000002513 implantation Methods 0.000 description 2
229940102223 injectable solution Drugs 0.000 description 2
239000007927 intramuscular injection Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 2
229910000103 lithium hydride Inorganic materials 0.000 description 2
KJGLZJQPMKQFIK-UHFFFAOYSA-N methanolate;tributylstannanylium Chemical compound CCCC[Sn](CCCC)(CCCC)OC KJGLZJQPMKQFIK-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
238000000465 moulding Methods 0.000 description 2
150000002791 naphthoquinones Chemical class 0.000 description 2
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
150000003014 phosphoric acid esters Chemical class 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
238000006366 phosphorylation reaction Methods 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
238000007493 shaping process Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
229940032147 starch Drugs 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 1
SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 1
WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
MOOFYEJFXBSZGE-QJUDHZBZSA-N 1,2-bis[(z)-(4-chlorophenyl)methylideneamino]guanidine Chemical compound C=1C=C(Cl)C=CC=1\C=N/N=C(/N)N\N=C/C1=CC=C(Cl)C=C1 MOOFYEJFXBSZGE-QJUDHZBZSA-N 0.000 description 1
MEWRGYQYQRUKMJ-UHFFFAOYSA-N 1-(4-phenylphenyl)propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1C1=CC=CC=C1 MEWRGYQYQRUKMJ-UHFFFAOYSA-N 0.000 description 1
SMTJEIXDYSROAO-UHFFFAOYSA-N 1-[3-(4-chlorophenoxy)phenyl]propan-2-one Chemical compound CC(=O)CC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 SMTJEIXDYSROAO-UHFFFAOYSA-N 0.000 description 1
IRFBKNONSURAII-UHFFFAOYSA-N 1-[3-chloro-4-(4-chlorophenoxy)phenyl]propan-2-one Chemical compound ClC1=CC(CC(=O)C)=CC=C1OC1=CC=C(Cl)C=C1 IRFBKNONSURAII-UHFFFAOYSA-N 0.000 description 1
FXDUDGXAWVDQFW-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 FXDUDGXAWVDQFW-UHFFFAOYSA-N 0.000 description 1
PIHPBYTYDXTTNV-UHFFFAOYSA-N 1-[4-(3-chlorophenoxy)phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OC1=CC=CC(Cl)=C1 PIHPBYTYDXTTNV-UHFFFAOYSA-N 0.000 description 1
FGHCFBNGNNEVDI-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)sulfonylphenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 FGHCFBNGNNEVDI-UHFFFAOYSA-N 0.000 description 1
DLMINFAFSWNBET-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1C1=CC=C(F)C=C1 DLMINFAFSWNBET-UHFFFAOYSA-N 0.000 description 1
ZIBBAPSCWQMFNA-UHFFFAOYSA-N 1-[4-(4-methoxyphenoxy)phenyl]propan-2-one Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(CC(C)=O)C=C1 ZIBBAPSCWQMFNA-UHFFFAOYSA-N 0.000 description 1
YLCNWIJDPOTGDU-UHFFFAOYSA-N 1-[4-(4-methylphenyl)sulfanylphenyl]propan-2-one Chemical compound CC1=CC=C(SC2=CC=C(C=C2)CC(C)=O)C=C1 YLCNWIJDPOTGDU-UHFFFAOYSA-N 0.000 description 1
PMNJMXFHKPBFTL-UHFFFAOYSA-N 1-[4-[(4-chlorophenyl)-difluoromethyl]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1C(F)(F)C1=CC=C(Cl)C=C1 PMNJMXFHKPBFTL-UHFFFAOYSA-N 0.000 description 1
LIAVBQBDCRWKGJ-UHFFFAOYSA-N 1-[4-[(4-chlorophenyl)methyl]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1CC1=CC=C(Cl)C=C1 LIAVBQBDCRWKGJ-UHFFFAOYSA-N 0.000 description 1
RHEINLBYFQFWCC-UHFFFAOYSA-N 1-[4-[2-(4-chlorophenyl)-2-oxoethyl]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1CC(=O)C1=CC=C(Cl)C=C1 RHEINLBYFQFWCC-UHFFFAOYSA-N 0.000 description 1
QJMHKXHVMGAWKO-UHFFFAOYSA-N 1-[4-[3-(trifluoromethyl)phenoxy]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 QJMHKXHVMGAWKO-UHFFFAOYSA-N 0.000 description 1
BMIIQXGHRILFLC-UHFFFAOYSA-N 1-[4-[4-(trifluoromethoxy)phenoxy]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 BMIIQXGHRILFLC-UHFFFAOYSA-N 0.000 description 1
OAHAYKQWLQAUKW-UHFFFAOYSA-N 1-[4-[4-(trifluoromethyl)phenoxy]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 OAHAYKQWLQAUKW-UHFFFAOYSA-N 0.000 description 1
MDFUBRJZADGZFN-UHFFFAOYSA-N 1-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 MDFUBRJZADGZFN-UHFFFAOYSA-N 0.000 description 1
PLRIYGLGEINYLD-UHFFFAOYSA-N 1-bromo-3-[(4-chlorophenyl)methyl]benzene Chemical compound C1=CC(Cl)=CC=C1CC1=CC=CC(Br)=C1 PLRIYGLGEINYLD-UHFFFAOYSA-N 0.000 description 1
WMXVUHANYJZYHO-UHFFFAOYSA-N 1-bromo-4-(4-chlorophenyl)benzene Chemical group C1=CC(Cl)=CC=C1C1=CC=C(Br)C=C1 WMXVUHANYJZYHO-UHFFFAOYSA-N 0.000 description 1
XFGPSHWWPIFPNL-UHFFFAOYSA-N 1-bromo-4-(4-fluorophenyl)benzene Chemical group C1=CC(F)=CC=C1C1=CC=C(Br)C=C1 XFGPSHWWPIFPNL-UHFFFAOYSA-N 0.000 description 1
PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-UHFFFAOYSA-N 0.000 description 1
RIHXMHKNTLBIPJ-UHFFFAOYSA-N 1-nitroprop-1-ene Chemical class CC=C[N+]([O-])=O RIHXMHKNTLBIPJ-UHFFFAOYSA-N 0.000 description 1
TZTXTIBZSSSFDI-UHFFFAOYSA-N 1-pyridin-2-ylpropan-2-one Chemical compound CC(=O)CC1=CC=CC=N1 TZTXTIBZSSSFDI-UHFFFAOYSA-N 0.000 description 1
ZQONXTQOKSPKDM-UHFFFAOYSA-N 2,6-dimethyl-3-(4-phenylphenyl)pyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C ZQONXTQOKSPKDM-UHFFFAOYSA-N 0.000 description 1
FTVYIUKYVYSAQY-UHFFFAOYSA-N 2,6-dimethyl-3-[4-(trifluoromethyl)phenyl]pyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(=CC=2)C(F)(F)F)=C1C FTVYIUKYVYSAQY-UHFFFAOYSA-N 0.000 description 1
PJDWMFZHOJJQGO-UHFFFAOYSA-N 2,6-dimethyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]pyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C PJDWMFZHOJJQGO-UHFFFAOYSA-N 0.000 description 1
RYOIPOKPCFXUKG-UHFFFAOYSA-N 2,6-dimethyl-3-[4-[4-(trifluoromethyl)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound N1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(=CC=3)C(F)(F)F)=CC=2)=C1C RYOIPOKPCFXUKG-UHFFFAOYSA-N 0.000 description 1
XZFQUUORMLBLLN-UHFFFAOYSA-N 2,6-dimethyl-3-[4-[4-(trifluoromethyl)phenoxy]phenyl]pyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(=CC=3)C(F)(F)F)=CC=2)=C1C XZFQUUORMLBLLN-UHFFFAOYSA-N 0.000 description 1
RMDLFJOOIBPSAU-UHFFFAOYSA-N 2,6-dimethyl-3-phenylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC=CC=2)=C1C RMDLFJOOIBPSAU-UHFFFAOYSA-N 0.000 description 1
UEERPCZVXPLDMN-UHFFFAOYSA-N 2-(4-tert-butylcyclohexyl)acetic acid Chemical compound CC(C)(C)C1CCC(CC(O)=O)CC1 UEERPCZVXPLDMN-UHFFFAOYSA-N 0.000 description 1
GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 1
LUBUYTZURNAUEE-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C(=CC(Cl)=CC=2)Cl)=C1C LUBUYTZURNAUEE-UHFFFAOYSA-N 0.000 description 1
BTDAYSGBCVLZCI-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=C(Cl)C(Cl)=CC=2)=C1C BTDAYSGBCVLZCI-UHFFFAOYSA-N 0.000 description 1
XABACRVKHMHDNI-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(Cl)=CC=2)=C1C XABACRVKHMHDNI-UHFFFAOYSA-N 0.000 description 1
VNWYXTBIAQCUFG-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(F)=CC=2)=C1C VNWYXTBIAQCUFG-UHFFFAOYSA-N 0.000 description 1
PSSHTECKEPLUMJ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2,6-dimethylpyran-4-one Chemical compound C1=CC(OC)=CC=C1C1=C(C)OC(C)=CC1=O PSSHTECKEPLUMJ-UHFFFAOYSA-N 0.000 description 1
DNFGUZYOMQENSE-UHFFFAOYSA-N 3-(cyclohexylmethyl)-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(CC2CCCCC2)=C1C DNFGUZYOMQENSE-UHFFFAOYSA-N 0.000 description 1
RCFUYMMQUOJABR-UHFFFAOYSA-N 3-[3-(4-chlorophenoxy)phenyl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound N1C(C)=CC(=O)C(C=2C=C(OC=3C=CC(Cl)=CC=3)C=CC=2)=C1C RCFUYMMQUOJABR-UHFFFAOYSA-N 0.000 description 1
SMUUHCKBYHDICJ-UHFFFAOYSA-N 3-[3-(4-chlorophenoxy)phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=C(OC=3C=CC(Cl)=CC=3)C=CC=2)=C1C SMUUHCKBYHDICJ-UHFFFAOYSA-N 0.000 description 1
VTGWIADISVBQTO-UHFFFAOYSA-N 3-[3-chloro-4-(4-chlorophenoxy)phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=C(Cl)C(OC=3C=CC(Cl)=CC=3)=CC=2)=C1C VTGWIADISVBQTO-UHFFFAOYSA-N 0.000 description 1
JEMUBTUKLKQPJK-UHFFFAOYSA-N 3-[4-(3-chlorophenoxy)phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(OC=3C=C(Cl)C=CC=3)=CC=2)=C1C JEMUBTUKLKQPJK-UHFFFAOYSA-N 0.000 description 1
VSCDKTPCBYFQQA-UHFFFAOYSA-N 3-[4-(4-chlorophenoxy)phenyl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound N1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=C1C VSCDKTPCBYFQQA-UHFFFAOYSA-N 0.000 description 1
FWKQRBYAFCNBHM-UHFFFAOYSA-N 3-[4-(4-chlorophenoxy)phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=C1C FWKQRBYAFCNBHM-UHFFFAOYSA-N 0.000 description 1
HGCYBPKBNFQVRW-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)sulfanylphenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(SC=3C=CC(Cl)=CC=3)=CC=2)=C1C HGCYBPKBNFQVRW-UHFFFAOYSA-N 0.000 description 1
UDNQGKRZAURAJN-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)sulfonylphenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1C UDNQGKRZAURAJN-UHFFFAOYSA-N 0.000 description 1
CNXMBALZKWQOQW-UHFFFAOYSA-N 3-[4-[(4-chlorophenyl)-difluoromethyl]phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(=CC=2)C(F)(F)C=2C=CC(Cl)=CC=2)=C1C CNXMBALZKWQOQW-UHFFFAOYSA-N 0.000 description 1
SIRBVJNUTUIAAZ-UHFFFAOYSA-N 3-[4-[(4-chlorophenyl)methyl]phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(CC=3C=CC(Cl)=CC=3)=CC=2)=C1C SIRBVJNUTUIAAZ-UHFFFAOYSA-N 0.000 description 1
CTNJKQWNEJXMOK-UHFFFAOYSA-N 3-[4-[2-(4-chlorophenyl)-2-oxoethyl]phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(CC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1C CTNJKQWNEJXMOK-UHFFFAOYSA-N 0.000 description 1
UXBLDQMSOWQULB-UHFFFAOYSA-N 3-amino-2-methyl-6,7,8,9-tetrahydro-5h-cyclohepta[2,3]thieno[2,4-d]pyrimidin-4-one Chemical compound C1CCCCC2=C1SC1=C2C(=O)N(N)C(C)=N1 UXBLDQMSOWQULB-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
UEHUENMJTRZMPB-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[4-(4-methylsulfinylphenoxy)phenyl]-3h-pyridin-4-one Chemical compound O=C1C(Br)C(C)=NC(C)=C1C(C=C1)=CC=C1OC1=CC=C(S(C)=O)C=C1 UEHUENMJTRZMPB-UHFFFAOYSA-N 0.000 description 1
JZQPVOWNOXEYCY-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[4-[3-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=CC(OC(F)(F)F)=C1 JZQPVOWNOXEYCY-UHFFFAOYSA-N 0.000 description 1
VXFYERKNBYUOLK-UHFFFAOYSA-N 3-bromo-5-(cyclohexylmethyl)-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1CC1CCCCC1 VXFYERKNBYUOLK-UHFFFAOYSA-N 0.000 description 1
SELLVCOHPDBPSJ-UHFFFAOYSA-N 3-bromo-5-[4-(4-chlorophenoxy)phenyl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 SELLVCOHPDBPSJ-UHFFFAOYSA-N 0.000 description 1
YQQQWHXPHSTBFE-UHFFFAOYSA-N 3-cyclohexyl-2,6-dimethyl-1h-pyridin-4-one Chemical compound N1C(C)=CC(=O)C(C2CCCCC2)=C1C YQQQWHXPHSTBFE-UHFFFAOYSA-N 0.000 description 1
URLOSHBYGSZBLL-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)benzaldehyde Chemical compound ClC1=CC(Cl)=CC=C1OC1=CC=C(C=O)C=C1 URLOSHBYGSZBLL-UHFFFAOYSA-N 0.000 description 1
ATGVBRQQWGDSHD-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)benzaldehyde Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1=CC=C(C=O)C=C1 ATGVBRQQWGDSHD-UHFFFAOYSA-N 0.000 description 1
YBZDGGHCOBODKY-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)benzaldehyde Chemical compound ClC1=CC(Cl)=CC(OC=2C=CC(C=O)=CC=2)=C1 YBZDGGHCOBODKY-UHFFFAOYSA-N 0.000 description 1
BGMYGFFWBQIXHN-UHFFFAOYSA-N 4-(3-chlorophenoxy)benzaldehyde Chemical compound ClC1=CC=CC(OC=2C=CC(C=O)=CC=2)=C1 BGMYGFFWBQIXHN-UHFFFAOYSA-N 0.000 description 1
BLCXBCYVCDPFEU-UHFFFAOYSA-N 4-(4-chlorophenoxy)benzaldehyde Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C=O)C=C1 BLCXBCYVCDPFEU-UHFFFAOYSA-N 0.000 description 1
YUPBWHURNLRZQL-UHFFFAOYSA-N 4-(4-fluorophenoxy)benzaldehyde Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=O)C=C1 YUPBWHURNLRZQL-UHFFFAOYSA-N 0.000 description 1
XXZKVKMXUPYUTR-UHFFFAOYSA-N 4-(4-methoxyphenoxy)benzaldehyde Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C=O)C=C1 XXZKVKMXUPYUTR-UHFFFAOYSA-N 0.000 description 1
CAXODQYDWCYSBN-UHFFFAOYSA-N 4-(4-methylphenyl)sulfanylbenzaldehyde Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C=O)C=C1 CAXODQYDWCYSBN-UHFFFAOYSA-N 0.000 description 1
YNYAJGSQILEFLD-UHFFFAOYSA-N 4-[3-(trifluoromethoxy)phenoxy]benzaldehyde Chemical compound FC(F)(F)OC1=CC=CC(OC=2C=CC(C=O)=CC=2)=C1 YNYAJGSQILEFLD-UHFFFAOYSA-N 0.000 description 1
FEAIQXYYLIXIGJ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenoxy]benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(OC=2C=CC(C=O)=CC=2)=C1 FEAIQXYYLIXIGJ-UHFFFAOYSA-N 0.000 description 1
QPNDRDXLIXUBFL-UHFFFAOYSA-N 4-[4-(trifluoromethoxy)phenoxy]benzaldehyde Chemical compound C1=CC(OC(F)(F)F)=CC=C1OC1=CC=C(C=O)C=C1 QPNDRDXLIXUBFL-UHFFFAOYSA-N 0.000 description 1
OGCKARXSAOHPMB-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(difluoromethyl)benzene Chemical compound FC(F)C1=CC=C(Br)C=C1C1=CC=C(Cl)C=C1 OGCKARXSAOHPMB-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
241000224482 Apicomplexa Species 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
NAPNOSFRRMHNBJ-UHFFFAOYSA-N Arprinocid Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=C(F)C=CC=C1Cl NAPNOSFRRMHNBJ-UHFFFAOYSA-N 0.000 description 1
241000271566 Aves Species 0.000 description 1
241000223836 Babesia Species 0.000 description 1
DUIWGFSMLDRAKN-UHFFFAOYSA-N CC1=NC(=CC(C1C1=CC=C(C=C1)SC1=CC=C(C=C1)C)=O)C Chemical compound CC1=NC(=CC(C1C1=CC=C(C=C1)SC1=CC=C(C=C1)C)=O)C DUIWGFSMLDRAKN-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
SRGKCPKJOAISJP-UHFFFAOYSA-N ClC1=CC=C(OC2=CC=C(C=C2)C2=C(N(C(=CC2=O)C)O)C)C=C1.C(C)(=O)OC1=C(C(=NC(=C1C1=CC=C(C=C1)OC1=CC=C(C=C1)OC(F)(F)F)C)C)Cl Chemical compound ClC1=CC=C(OC2=CC=C(C=C2)C2=C(N(C(=CC2=O)C)O)C)C=C1.C(C)(=O)OC1=C(C(=NC(=C1C1=CC=C(C=C1)OC1=CC=C(C=C1)OC(F)(F)F)C)C)Cl SRGKCPKJOAISJP-UHFFFAOYSA-N 0.000 description 1
WEPDWWFTSVHBMQ-XYPYZODXSA-N Clc1ccc(cc1)[C@H]1CC[C@H](CBr)CC1 Chemical compound Clc1ccc(cc1)[C@H]1CC[C@H](CBr)CC1 WEPDWWFTSVHBMQ-XYPYZODXSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
241000223935 Cryptosporidium Species 0.000 description 1
244000303965 Cyamopsis psoralioides Species 0.000 description 1
ZEFNOZRLAWVAQF-UHFFFAOYSA-N Dinitolmide Chemical compound CC1=C(C(N)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZEFNOZRLAWVAQF-UHFFFAOYSA-N 0.000 description 1
241000223934 Eimeria maxima Species 0.000 description 1
241000223932 Eimeria tenella Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
FOHHNHSLJDZUGQ-VWLOTQADSA-N Halofantrine Chemical compound FC(F)(F)C1=CC=C2C([C@@H](O)CCN(CCCC)CCCC)=CC3=C(Cl)C=C(Cl)C=C3C2=C1 FOHHNHSLJDZUGQ-VWLOTQADSA-N 0.000 description 1
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 1
206010061598 Immunodeficiency Diseases 0.000 description 1
241000222722 Leishmania <genus> Species 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
241001375804 Mastigophora Species 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
229930191564 Monensin Natural products 0.000 description 1
GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 description 1
229920000715 Mucilage Polymers 0.000 description 1
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000223830 Plasmodium yoelii Species 0.000 description 1
206010035660 Pneumocystis Infections Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010067171 Regurgitation Diseases 0.000 description 1
KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 description 1
239000004189 Salinomycin Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
241000223777 Theileria Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
241000223996 Toxoplasma Species 0.000 description 1
229920001938 Vegetable gum Polymers 0.000 description 1
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
INSWJXJRICZMOG-UHFFFAOYSA-N [4-(4-chlorophenyl)cyclohexyl]methanol Chemical compound C1CC(CO)CCC1C1=CC=C(Cl)C=C1 INSWJXJRICZMOG-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229960003683 amprolium Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000078 anti-malarial effect Effects 0.000 description 1
230000000842 anti-protozoal effect Effects 0.000 description 1
230000003428 anti-theilerial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940124536 anticoccidial agent Drugs 0.000 description 1
239000003904 antiprotozoal agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229950002343 arprinocid Drugs 0.000 description 1
BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 description 1
201000008680 babesiosis Diseases 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
244000309464 bull Species 0.000 description 1
150000001669 calcium Chemical class 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000007958 cherry flavor Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960003677 chloroquine Drugs 0.000 description 1
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
229960002227 clindamycin Drugs 0.000 description 1
239000003224 coccidiostatic agent Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
UHBZEAPZATVYKV-UHFFFAOYSA-N cyclohexylacetone Chemical compound CC(=O)CC1CCCCC1 UHBZEAPZATVYKV-UHFFFAOYSA-N 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
229960003934 dinitolmide Drugs 0.000 description 1
UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
229960003722 doxycycline Drugs 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
229940116333 ethyl lactate Drugs 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229960003242 halofantrine Drugs 0.000 description 1
LVASCWIMLIKXLA-LSDHHAIUSA-N halofuginone Chemical compound O[C@@H]1CCCN[C@H]1CC(=O)CN1C(=O)C2=CC(Cl)=C(Br)C=C2N=C1 LVASCWIMLIKXLA-LSDHHAIUSA-N 0.000 description 1
229950010152 halofuginone Drugs 0.000 description 1
230000036541 health Effects 0.000 description 1
238000005534 hematocrit Methods 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical compound Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 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
239000003701 inert diluent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229940102213 injectable suspension Drugs 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229960001962 mefloquine Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
238000005497 microtitration Methods 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
229960005358 monensin Drugs 0.000 description 1
GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
OTYPIDNRISCWQY-UHFFFAOYSA-L palladium(2+);tris(2-methylphenyl)phosphane;dichloride Chemical compound Cl[Pd]Cl.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C OTYPIDNRISCWQY-UHFFFAOYSA-L 0.000 description 1
QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
150000002989 phenols Chemical class 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
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
229960000611 pyrimethamine Drugs 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229960004591 robenidine Drugs 0.000 description 1
210000004767 rumen Anatomy 0.000 description 1
229960001548 salinomycin Drugs 0.000 description 1
235000019378 salinomycin Nutrition 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004016 sucrose syrup Drugs 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 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
229960002180 tetracycline Drugs 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Tropical Medicine & Parasitology (AREA)
Public Health (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL9750191A 1990-03-12 1991-03-11 History of 4-pyridone. And pharmaceutical preparations containing them IL97501A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB909005518A GB9005518D0 (en)	1990-03-12	1990-03-12	Heterocyclic compounds

Publications (2)

Publication Number	Publication Date
IL97501A0 IL97501A0 (en)	1992-06-21
IL97501A true IL97501A (en)	1995-03-15

Family

ID=10672464

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9750191A IL97501A (en)	1990-03-12	1991-03-11	History of 4-pyridone. And pharmaceutical preparations containing them

Country Status (17)

Country	Link
EP (1)	EP0447164A1 (hu)
JP (1)	JPH05504961A (hu)
AP (1)	AP271A (hu)
CA (1)	CA2078147A1 (hu)
CS (1)	CS63591A2 (hu)
FI (1)	FI924071A (hu)
GB (1)	GB9005518D0 (hu)
HU (1)	HUT68035A (hu)
IE (1)	IE910790A1 (hu)
IL (1)	IL97501A (hu)
MY (1)	MY106873A (hu)
NZ (1)	NZ237377A (hu)
OA (1)	OA09684A (hu)
PT (1)	PT97002A (hu)
TW (1)	TW201734B (hu)
WO (1)	WO1991013873A1 (hu)
ZA (1)	ZA911791B (hu)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0453210A3 (en) *	1990-04-19	1993-01-13	Imperial Chemical Industries Plc	Pyridine derivatives
FR2687674B1 (fr) *	1992-02-07	1995-05-19	Roussel Uclaf	Nouveaux derives de la pyridone, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant.
ES2256874T3 (es)	1996-02-02	2006-07-16	Kumiai Chemical Industry Co., Ltd.	Derivados de piridona y herbicidas.
JP2008531638A (ja) *	2005-03-04	2008-08-14	グラクソグループリミテッド	抗マラリアピリジノン誘導体
JP2009538873A (ja) *	2006-05-31	2009-11-12	グラクソグループリミテッド	新規複素環化合物
EP1967515A1 (en) *	2007-03-08	2008-09-10	Glaxo Group Limited	Heterocyclic compounds
EP1862459A1 (en) *	2006-05-31	2007-12-05	Glaxo Group Limited	Novel heterocyclic compounds
PT2220076E (pt)	2007-11-15	2012-04-26	Gilead Sciences Inc	Inibidores da replicação do vírus da imunodeficiência humana
CA2707418C (en)	2007-11-16	2013-11-19	Boehringer Ingelheim International Gmbh	Inhibitors of human immunodeficiency virus replication
JP2011504914A (ja) *	2007-11-30	2011-02-17	グラクソグループリミテッド	抗マラリア化合物の結晶形態
EP2246329A1 (en)	2009-01-19	2010-11-03	Glaxo Group Limited	4(1H)-pyridinone derivatives and their use as antimalaria agents
WO2010081904A1 (en)	2009-01-19	2010-07-22	Glaxo Group Limited	4 ( 1h) -pyridinone derivatives and their use as antimalaria agents
TW201039834A (en)	2009-02-20	2010-11-16	Glaxo Group Ltd	Novel heterocyclic compounds
CN113943294A (zh) *	2020-07-15	2022-01-18	成都海博为药业有限公司	一种作为btk抑制剂的化合物及其制备方法与用途

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL124395C (hu) *	1963-09-25
FR1451373A (fr) *	1965-07-06	1966-01-07		Nouveaux dérivés de la pyridine utilisables notamment comme parasiticides, et procédé pour leur préparation
JPS448514Y1 (hu) *	1966-09-10	1969-04-04
GB1291571A (en) *	1969-03-29	1972-10-04	Fisons Pharmaceuticals Ltd	Aza chromone-2-carboxylic acids
DE2162238C3 (de) *	1971-12-15	1981-07-02	C.H. Boehringer Sohn, 6507 Ingelheim	2-Methyl-3,5-dijod-4-hydroxy-6-chlorpyridin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel
AT362613B (de) *	1975-08-27	1981-06-10	Lilly Co Eli	Herbizides mittel
JPS6032631B2 (ja) *	1976-01-17	1985-07-29	日清製粉株式会社	ｒ−ピリドン系化合物、その製造方法およびそれらの化合物からなる農業用薬剤
US4235619A (en) *	1977-06-27	1980-11-25	Eli Lilly And Company	Method of controlling aquatic weeds and algae
JPS6059236B2 (ja) *	1977-07-06	1985-12-24	日清製粉株式会社	γ−ピロン誘導体、その製造方法およびそれらの化合物からなる農業用薬剤
GB8310140D0 (en) *	1983-04-14	1983-05-18	Wellcome Found	Antiprotozoal agents
DE3889167T2 (de) *	1987-08-18	1994-09-08	Ihara Chemical Ind Co	Pyridinon-Derivate und diese enthaltende fungizide Zusammenstellungen für die Landwirtschaft und Gartenbau.

1990
- 1990-03-12 GB GB909005518A patent/GB9005518D0/en active Pending
1991
- 1991-03-11 MY MYPI91000401A patent/MY106873A/en unknown
- 1991-03-11 NZ NZ237377A patent/NZ237377A/en unknown
- 1991-03-11 PT PT97002A patent/PT97002A/pt not_active Application Discontinuation
- 1991-03-11 WO PCT/GB1991/000380 patent/WO1991013873A1/en active Application Filing
- 1991-03-11 ZA ZA911791A patent/ZA911791B/xx unknown
- 1991-03-11 JP JP3505415A patent/JPH05504961A/ja active Pending
- 1991-03-11 HU HU9202903A patent/HUT68035A/hu unknown
- 1991-03-11 IL IL9750191A patent/IL97501A/en not_active IP Right Cessation
- 1991-03-11 TW TW080101913A patent/TW201734B/zh active
- 1991-03-11 CS CS91635A patent/CS63591A2/cs unknown
- 1991-03-11 IE IE079091A patent/IE910790A1/en unknown
- 1991-03-11 EP EP91302031A patent/EP0447164A1/en not_active Withdrawn
- 1991-03-11 CA CA002078147A patent/CA2078147A1/en not_active Abandoned
- 1991-03-12 AP APAP/P/1991/000243A patent/AP271A/en active
1992
- 1992-09-09 OA OA60270A patent/OA09684A/en unknown
- 1992-09-11 FI FI924071A patent/FI924071A/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
MY106873A (en)	1995-08-30
ZA911791B (en)	1992-11-25
NZ237377A (en)	1993-10-26
JPH05504961A (ja)	1993-07-29
FI924071A0 (fi)	1992-09-11
TW201734B (hu)	1993-03-11
FI924071A (fi)	1992-09-11
AP9100243A0 (en)	1991-04-30
IE910790A1 (en)	1991-09-25
GB9005518D0 (en)	1990-05-09
HU9202903D0 (en)	1993-04-28
OA09684A (en)	1993-05-15
WO1991013873A1 (en)	1991-09-19
AP271A (en)	1993-06-24
IL97501A0 (en)	1992-06-21
PT97002A (pt)	1991-11-29
CA2078147A1 (en)	1991-09-13
HUT68035A (en)	1995-05-29
CS63591A2 (en)	1991-12-17
EP0447164A1 (en)	1991-09-18

Publication	Publication Date	Title
IL97501A (en)	1995-03-15	History of 4-pyridone. And pharmaceutical preparations containing them
US5596008A (en)	1997-01-21	3,4-Diaryl substituted pyridines for the treatment of inflammation
US5021581A (en)	1991-06-04	Fungicides
KR102018409B1 (ko)	2019-09-04	부분적으로 포화된 질소 함유 복소환 화합물
JPH0316344B2 (hu)	1991-03-05
CA1302415C (en)	1992-06-02	1-hydroxy-2-pyridones, a process for their preparation, and medicaments which contain them, and intermediates formed in the preparation of the 1-hydroxy-2-pyridones
PT88456B (pt)	1992-10-30	Processo para a preparacao de derivados de acido propenoico e de composicoes fungicidas que os contem
JPH11500748A (ja)	1999-01-19	Ｃｏｘ−２阻害剤のプロドラッグとしての３，４−ジアリール−２−ヒドロキシ−２，５−ジヒドロフラン
CZ285586B6 (cs)	1999-09-15	Chemické sloučeniny
EP0072529B1 (en)	1986-01-29	Sulfur-substituted phenoxypyridines having antiviral activity
EP0304190B1 (en)	1992-07-08	(arylsulphonyl)nitromethanes, process for their preparation and use in pharmaceutical compositions
US5145954A (en)	1992-09-08	Derivatives of alphaphenylacrylic acid and their use in agriculture
US20090170886A1 (en)	2009-07-02	Androgen modulators
US5403934A (en)	1995-04-04	Heterocyclic compounds
DK158460B (da)	1990-05-21	Analogifremgangsmaade til fremstilling af substituerede oxocarboxylsyrer
AU644425B2 (en)	1993-12-09	Heterocyclic compounds
US4294842A (en)	1981-10-13	Anti-protozoal oxadiazole derivatives
US5179098A (en)	1993-01-12	Fungicides
JP2003534340A (ja)	2003-11-18	脂肪酸シンターゼ阻害剤
US4558134A (en)	1985-12-10	Certain phenoxy-pyridine-carbonitriles having antiviral activity
JP2002506851A (ja)	2002-03-05	カルボン酸類およびアシルスルホンアミド類、そのような化合物を含む組成物ならびに治療方法
EP0178633B1 (en)	1992-01-08	2-phenylpyrano[2,3-b]pyridines

Legal Events

Date	Code	Title	Description
1998-02-22	RH	Patent void