UA77408C2 - Metalloproteinase inhibitors, pharmaceutical composition on its base, and use thereof - Google Patents

Metalloproteinase inhibitors, pharmaceutical composition on its base, and use thereof Download PDF

Info

Publication number: UA77408C2
Authority: UA; Ukraine
Prior art keywords: group; alkyl; formula; compound; pharmaceutically acceptable
Prior art date: 2001-03-15

Application number

UA2003098168A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Astrazeneca Ab

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.)

2001-03-15

Filing date

2002-03-13

Publication date

2006-12-15

2002-03-13 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2006-12-15 Publication of UA77408C2 publication Critical patent/UA77408C2/uk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
239000003475 metalloproteinase inhibitor Substances 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 137
125000000217 alkyl group Chemical group 0.000 claims description 65
-1 p-ethoxyphenyl Chemical group 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 33
201000010099 disease Diseases 0.000 claims description 29
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
102000005741 Metalloproteases Human genes 0.000 claims description 23
108010006035 Metalloproteases Proteins 0.000 claims description 23
238000011282 treatment Methods 0.000 claims description 22
125000006413 ring segment Chemical group 0.000 claims description 21
238000000034 method Methods 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 13
125000002619 bicyclic group Chemical group 0.000 claims description 12
230000001404 mediated effect Effects 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
230000015572 biosynthetic process Effects 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000002950 monocyclic group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
JGSLKNWXPRDWBA-UHFFFAOYSA-N 2-methylidene-1h-pyridine Chemical compound C=C1NC=CC=C1 JGSLKNWXPRDWBA-UHFFFAOYSA-N 0.000 claims 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
206010008748 Chorea Diseases 0.000 claims 1
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
208000012601 choreatic disease Diseases 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 19
102100027998 Macrophage metalloelastase Human genes 0.000 abstract description 13
101000577881 Homo sapiens Macrophage metalloelastase Proteins 0.000 abstract description 9
102000004190 Enzymes Human genes 0.000 description 23
108090000790 Enzymes Proteins 0.000 description 23
229940088598 enzyme Drugs 0.000 description 23
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
210000004027 cell Anatomy 0.000 description 21
230000000694 effects Effects 0.000 description 20
125000001188 haloalkyl group Chemical group 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
238000004458 analytical method Methods 0.000 description 16
102000002274 Matrix Metalloproteinases Human genes 0.000 description 15
108010000684 Matrix Metalloproteinases Proteins 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
238000005481 NMR spectroscopy Methods 0.000 description 13
125000003118 aryl group Chemical group 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
230000027455 binding Effects 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
125000005842 heteroatom Chemical group 0.000 description 12
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 12
239000000758 substrate Substances 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 10
102100030411 Neutrophil collagenase Human genes 0.000 description 10
108060008682 Tumor Necrosis Factor Proteins 0.000 description 10
125000003277 amino group Chemical group 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
239000008280 blood Substances 0.000 description 10
125000004404 heteroalkyl group Chemical group 0.000 description 10
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
102000003390 tumor necrosis factor Human genes 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
229940124761 MMP inhibitor Drugs 0.000 description 8
241000700159 Rattus Species 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
210000001519 tissue Anatomy 0.000 description 8
102100030416 Stromelysin-1 Human genes 0.000 description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
206010003246 arthritis Diseases 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
201000006417 multiple sclerosis Diseases 0.000 description 7
210000002381 plasma Anatomy 0.000 description 7
108090000765 processed proteins & peptides Proteins 0.000 description 7
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
206010014561 Emphysema Diseases 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
201000008482 osteoarthritis Diseases 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
125000006168 tricyclic group Chemical group 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
102000008186 Collagen Human genes 0.000 description 5
108010035532 Collagen Proteins 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 5
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 5
101000990908 Homo sapiens Neutrophil collagenase Proteins 0.000 description 5
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
101710118230 Neutrophil collagenase Proteins 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 5
102100029645 UBX domain-containing protein 11 Human genes 0.000 description 5
125000005157 alkyl carboxy group Chemical group 0.000 description 5
125000004103 aminoalkyl group Chemical group 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
239000002585 base Substances 0.000 description 5
229920001436 collagen Polymers 0.000 description 5
210000002744 extracellular matrix Anatomy 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 4
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 4
102000029816 Collagenase Human genes 0.000 description 4
108060005980 Collagenase Proteins 0.000 description 4
241000282412 Homo Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
101710187853 Macrophage metalloelastase Proteins 0.000 description 4
206010027476 Metastases Diseases 0.000 description 4
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
206010028980 Neoplasm Diseases 0.000 description 4
102000035195 Peptidases Human genes 0.000 description 4
108091005804 Peptidases Proteins 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
101710108790 Stromelysin-1 Proteins 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
125000003368 amide group Chemical group 0.000 description 4
239000001099 ammonium carbonate Substances 0.000 description 4
235000012501 ammonium carbonate Nutrition 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
239000000872 buffer Substances 0.000 description 4
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000012937 correction Methods 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 4
125000004446 heteroarylalkyl group Chemical group 0.000 description 4
150000001469 hydantoins Chemical class 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
230000009545 invasion Effects 0.000 description 4
210000002540 macrophage Anatomy 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
206010039073 rheumatoid arthritis Diseases 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
CZYMNCPDEOQKIL-UHFFFAOYSA-N 5-(aminomethyl)imidazolidine-2,4-dione Chemical compound NCC1NC(=O)NC1=O CZYMNCPDEOQKIL-UHFFFAOYSA-N 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 3
208000003174 Brain Neoplasms Diseases 0.000 description 3
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
201000004624 Dermatitis Diseases 0.000 description 3
101000990915 Homo sapiens Stromelysin-1 Proteins 0.000 description 3
108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 3
101710170181 Metalloproteinase inhibitor Proteins 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
150000001356 alkyl thiols Chemical class 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
239000002246 antineoplastic agent Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
238000003556 assay Methods 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000001413 cellular effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000006378 damage Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000005462 imide group Chemical group 0.000 description 3
239000000463 material Substances 0.000 description 3
239000012528 membrane Substances 0.000 description 3
229940126170 metalloproteinase inhibitor Drugs 0.000 description 3
230000009401 metastasis Effects 0.000 description 3
125000006178 methyl benzyl group Chemical group 0.000 description 3
125000006384 methylpyridyl group Chemical group 0.000 description 3
210000000440 neutrophil Anatomy 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
235000018102 proteins Nutrition 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
238000012552 review Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
150000004763 sulfides Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
230000009466 transformation Effects 0.000 description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 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
102000016284 Aggrecans Human genes 0.000 description 2
108010067219 Aggrecans Proteins 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
102000004506 Blood Proteins Human genes 0.000 description 2
108010017384 Blood Proteins Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
102000000503 Collagen Type II Human genes 0.000 description 2
108010041390 Collagen Type II Proteins 0.000 description 2
102100027995 Collagenase 3 Human genes 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
208000018035 Dental disease Diseases 0.000 description 2
208000009386 Experimental Arthritis Diseases 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
230000005526 G1 to G0 transition Effects 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
102100030417 Matrilysin Human genes 0.000 description 2
102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
102000056189 Neutrophil collagenases Human genes 0.000 description 2
108030001564 Neutrophil collagenases Proteins 0.000 description 2
239000004365 Protease Substances 0.000 description 2
102000016611 Proteoglycans Human genes 0.000 description 2
108010067787 Proteoglycans Proteins 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
208000014151 Stomatognathic disease Diseases 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
206010052428 Wound Diseases 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000005418 aryl aryl group Chemical group 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
235000019504 cigarettes Nutrition 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
229960002424 collagenase Drugs 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
238000011161 development Methods 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
210000002615 epidermis Anatomy 0.000 description 2
210000000981 epithelium Anatomy 0.000 description 2
239000000284 extract Substances 0.000 description 2
230000003176 fibrotic effect Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
229920000669 heparin Polymers 0.000 description 2
125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
230000008595 infiltration Effects 0.000 description 2
238000001764 infiltration Methods 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000003993 interaction Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
210000002510 keratinocyte Anatomy 0.000 description 2
230000003902 lesion Effects 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
208000010125 myocardial infarction Diseases 0.000 description 2
230000011164 ossification Effects 0.000 description 2
230000003285 pharmacodynamic effect Effects 0.000 description 2
229920005990 polystyrene resin Polymers 0.000 description 2
239000002243 precursor Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
235000019833 protease Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
208000037803 restenosis Diseases 0.000 description 2
206010039083 rhinitis Diseases 0.000 description 2
230000007017 scission Effects 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
239000010959 steel Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
150000003456 sulfonamides Chemical class 0.000 description 2
230000006103 sulfonylation Effects 0.000 description 2
238000005694 sulfonylation reaction Methods 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000017423 tissue regeneration Effects 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
210000002993 trophoblast Anatomy 0.000 description 2
230000004572 zinc-binding Effects 0.000 description 2
125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 description 1
108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 1
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
QPRATAOCXWOIPO-UHFFFAOYSA-N 2-nitroethene-1,1-diamine Chemical compound NC(N)=C[N+]([O-])=O QPRATAOCXWOIPO-UHFFFAOYSA-N 0.000 description 1
SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 1
IXBZJPOQTSAQHW-UHFFFAOYSA-N 4-phenylbutane-2-thione Chemical compound CC(=S)CCC1=CC=CC=C1 IXBZJPOQTSAQHW-UHFFFAOYSA-N 0.000 description 1
102100026802 72 kDa type IV collagenase Human genes 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
102000034473 Adamalysin Human genes 0.000 description 1
108030001653 Adamalysin Proteins 0.000 description 1
108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 1
102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 1
241001516584 Andrya Species 0.000 description 1
206010002329 Aneurysm Diseases 0.000 description 1
241001123248 Arma Species 0.000 description 1
102000034498 Astacin Human genes 0.000 description 1
108090000658 Astacin Proteins 0.000 description 1
208000020084 Bone disease Diseases 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
206010009900 Colitis ulcerative Diseases 0.000 description 1
102000012422 Collagen Type I Human genes 0.000 description 1
108010022452 Collagen Type I Proteins 0.000 description 1
244000241257 Cucumis melo Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
101000616562 Danio rerio Sonic hedgehog protein A Proteins 0.000 description 1
208000016192 Demyelinating disease Diseases 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
102000016942 Elastin Human genes 0.000 description 1
108010014258 Elastin Proteins 0.000 description 1
201000009273 Endometriosis Diseases 0.000 description 1
108010062466 Enzyme Precursors Proteins 0.000 description 1
102000010911 Enzyme Precursors Human genes 0.000 description 1
208000007659 Fibroadenoma Diseases 0.000 description 1
108010067306 Fibronectins Proteins 0.000 description 1
102000016359 Fibronectins Human genes 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
108010026132 Gelatinases Proteins 0.000 description 1
102000013382 Gelatinases Human genes 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
101000627872 Homo sapiens 72 kDa type IV collagenase Proteins 0.000 description 1
101000577887 Homo sapiens Collagenase 3 Proteins 0.000 description 1
101001013150 Homo sapiens Interstitial collagenase Proteins 0.000 description 1
101001011906 Homo sapiens Matrix metalloproteinase-14 Proteins 0.000 description 1
101001011884 Homo sapiens Matrix metalloproteinase-15 Proteins 0.000 description 1
101001011886 Homo sapiens Matrix metalloproteinase-16 Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-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
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
208000012659 Joint disease Diseases 0.000 description 1
206010023421 Kidney fibrosis Diseases 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
108090000855 Matrilysin Proteins 0.000 description 1
102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 1
108010076501 Matrix Metalloproteinase 12 Proteins 0.000 description 1
108010076503 Matrix Metalloproteinase 13 Proteins 0.000 description 1
102100030216 Matrix metalloproteinase-14 Human genes 0.000 description 1
102100030201 Matrix metalloproteinase-15 Human genes 0.000 description 1
102100030200 Matrix metalloproteinase-16 Human genes 0.000 description 1
102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 1
108010052285 Membrane Proteins Proteins 0.000 description 1
101150101095 Mmp12 gene Proteins 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
208000010191 Osteitis Deformans Diseases 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
208000027868 Paget disease Diseases 0.000 description 1
102000016387 Pancreatic elastase Human genes 0.000 description 1
108010067372 Pancreatic elastase Proteins 0.000 description 1
208000037273 Pathologic Processes Diseases 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
206010036030 Polyarthritis Diseases 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000288906 Primates Species 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
101150010457 SAS5 gene Proteins 0.000 description 1
206010040943 Skin Ulcer Diseases 0.000 description 1
206010072170 Skin wound Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
206010064996 Ulcerative keratitis Diseases 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
206010047571 Visual impairment Diseases 0.000 description 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
108010003059 aggrecanase Proteins 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
125000005599 alkyl carboxylate group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
210000001132 alveolar macrophage Anatomy 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
229940124346 antiarthritic agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
239000003435 antirheumatic agent Substances 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005362 aryl sulfone group Chemical group 0.000 description 1
150000001504 aryl thiols Chemical class 0.000 description 1
239000012131 assay buffer Substances 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
230000014461 bone development Effects 0.000 description 1
230000008468 bone growth Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
238000001354 calcination Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
208000006170 carotid stenosis Diseases 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000000845 cartilage Anatomy 0.000 description 1
230000008355 cartilage degradation Effects 0.000 description 1
230000008619 cell matrix interaction Effects 0.000 description 1
230000012292 cell migration Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
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 1
238000000451 chemical ionisation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 description 1
210000001612 chondrocyte Anatomy 0.000 description 1
208000001277 chronic periodontitis Diseases 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000000112 colonic effect Effects 0.000 description 1
239000002299 complementary DNA Substances 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000004734 cutaneous carcinogenesis Effects 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
229960003067 cystine Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
229920002549 elastin Polymers 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000013020 embryo development Effects 0.000 description 1
210000005175 epidermal keratinocyte Anatomy 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
230000008472 epithelial growth Effects 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical compound CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
210000000497 foam cell Anatomy 0.000 description 1
238000009472 formulation Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000012812 general test Methods 0.000 description 1
238000009650 gentamicin protection assay Methods 0.000 description 1
208000024693 gingival disease Diseases 0.000 description 1
208000007565 gingivitis Diseases 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
230000035876 healing Effects 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
208000014951 hematologic disease Diseases 0.000 description 1
ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical group CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
210000001624 hip Anatomy 0.000 description 1
210000004394 hip joint Anatomy 0.000 description 1
102000047338 human MMP12 Human genes 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000008274 jelly Substances 0.000 description 1
208000018937 joint inflammation Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 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
230000003211 malignant effect Effects 0.000 description 1
208000027202 mammary Paget disease Diseases 0.000 description 1
210000005075 mammary gland Anatomy 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000005906 menstruation Effects 0.000 description 1
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
108020004999 messenger RNA Proteins 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
238000010172 mouse model Methods 0.000 description 1
GTMQOMPXVQGITC-UHFFFAOYSA-N n-[(2,5-dioxoimidazolidin-4-yl)methyl]-5-pyridin-2-ylthiophene-2-sulfonamide Chemical compound O=C1NC(=O)NC1CNS(=O)(=O)C1=CC=C(C=2N=CC=CC=2)S1 GTMQOMPXVQGITC-UHFFFAOYSA-N 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
239000007922 nasal spray Substances 0.000 description 1
239000006225 natural substrate Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003349 osteoarthritic effect Effects 0.000 description 1
210000002997 osteoclast Anatomy 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
210000003681 parotid gland Anatomy 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000009054 pathological process Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
201000001245 periodontitis Diseases 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
210000002826 placenta Anatomy 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
208000030428 polyarticular arthritis Diseases 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
230000001323 posttranslational effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
235000019419 proteases Nutrition 0.000 description 1
230000002797 proteolythic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
230000005070 ripening Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000000779 smoke Substances 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
206010041823 squamous cell carcinoma Diseases 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000012134 supernatant fraction Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
210000001179 synovial fluid Anatomy 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
ISTGQSQWSKCNFJ-UHFFFAOYSA-N tert-butyl n-ethylcarbamate Chemical compound CCNC(=O)OC(C)(C)C ISTGQSQWSKCNFJ-UHFFFAOYSA-N 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000007306 turnover Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
230000029663 wound healing Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- 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
- A61P11/02—Nasal agents, e.g. decongestants
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- 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
- 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- 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
- C07D401/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Cardiology (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Endocrinology (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Vascular Medicine (AREA)
Psychiatry (AREA)
Oncology (AREA)
Otolaryngology (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Reproductive Health (AREA)

UA2003098168A 2001-03-15 2002-03-13 Metalloproteinase inhibitors, pharmaceutical composition on its base, and use thereof UA77408C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE0100902A SE0100902D0 (sv)	2001-03-15	2001-03-15	Compounds
PCT/SE2002/000478 WO2002074751A1 (fr)	2001-03-15	2002-03-13	Inhibiteurs des metalloproteinases

Publications (1)

Publication Number	Publication Date
UA77408C2 true UA77408C2 (en)	2006-12-15

Family

ID=20283374

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
UA2003098168A UA77408C2 (en)	2001-03-15	2002-03-13	Metalloproteinase inhibitors, pharmaceutical composition on its base, and use thereof
UA2003098171A UA78502C2 (en)	2001-03-15	2002-03-13	Metalloproteinase inhibitors, use thereof, and pharmaceutical composition based thereon
UA2003098170A UA77667C2 (en)	2001-03-15	2002-03-13	Metalloproteinase inhibitors, pharmaceutical composition and use thereof

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
UA2003098171A UA78502C2 (en)	2001-03-15	2002-03-13	Metalloproteinase inhibitors, use thereof, and pharmaceutical composition based thereon
UA2003098170A UA77667C2 (en)	2001-03-15	2002-03-13	Metalloproteinase inhibitors, pharmaceutical composition and use thereof

Country Status (33)

Country	Link
US (8)	US7427631B2 (fr)
EP (4)	EP1370534A1 (fr)
JP (4)	JP4390457B2 (fr)
KR (4)	KR20030082986A (fr)
CN (5)	CN101602731A (fr)
AR (2)	AR035443A1 (fr)
AT (3)	ATE493406T1 (fr)
AU (2)	AU2002237626B2 (fr)
BR (3)	BR0207984A (fr)
CA (3)	CA2440473C (fr)
CY (1)	CY1107525T1 (fr)
CZ (3)	CZ20032499A3 (fr)
DE (3)	DE60213216T2 (fr)
DK (1)	DK1370556T3 (fr)
EE (3)	EE05364B1 (fr)
ES (3)	ES2267986T3 (fr)
HK (3)	HK1091492A1 (fr)
HU (3)	HUP0400194A3 (fr)
IL (5)	IL157657A0 (fr)
IS (3)	IS6943A (fr)
MX (3)	MXPA03008191A (fr)
MY (2)	MY136789A (fr)
NO (3)	NO20034044L (fr)
NZ (3)	NZ528106A (fr)
PL (3)	PL205315B1 (fr)
PT (1)	PT1370556E (fr)
RU (3)	RU2285695C2 (fr)
SE (1)	SE0100902D0 (fr)
SI (1)	SI1370556T1 (fr)
SK (3)	SK10952003A3 (fr)
UA (3)	UA77408C2 (fr)
WO (3)	WO2002074751A1 (fr)
ZA (4)	ZA200306732B (fr)

Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE0100903D0 (sv) *	2001-03-15	2001-03-15	Astrazeneca Ab	Compounds
SE0100902D0 (sv) *	2001-03-15	2001-03-15	Astrazeneca Ab	Compounds
JP2004535411A (ja)	2001-05-25	2004-11-25	ブリストルーマイヤーズスクイブカンパニー	マトリックスメタロプロテナーゼ及び／またはＴＮＦ−α転換酵素（ＴＡＣＥ）の阻害剤としてのヒダントイン及び関連複素環化合物
SE0103710D0 (sv) *	2001-11-07	2001-11-07	Astrazeneca Ab	Compounds
DE10221018A1 (de) *	2002-05-11	2003-11-27	Boehringer Ingelheim Pharma	Verwendung von Hemmern der EGFR-vermittelten Signaltransduktion zur Behandlung von gutartiger Prostatahyperplasie (BPH)/Prostatahypertrophie
SE0202539D0 (sv)	2002-08-27	2002-08-27	Astrazeneca Ab	Compounds
SE0202693D0 (sv) *	2002-09-11	2002-09-11	Astrazeneca Ab	Compounds
GB0221246D0 (en) *	2002-09-13	2002-10-23	Astrazeneca Ab	Compounds
EP1546109A4 (fr) *	2002-10-04	2005-11-09	Bristol Myers Squibb Co	Derives d'hydantoine en tant qu'inhibiteurs de metalloproteinases matricielles et/ou de l'enzyme de conversion de tnf-alpha (tace)
JP4866610B2 (ja)	2003-08-18	2012-02-01	富士フイルムファインケミカルズ株式会社	ピリジルテトラヒドロピリジン類およびピリジルピペリジン類
US20050203156A1 (en) *	2004-03-12	2005-09-15	Wyeth	Hydantoins having RNase modulatory activity
US7648992B2 (en) *	2004-07-05	2010-01-19	Astrazeneca Ab	Hydantoin derivatives for the treatment of obstructive airway diseases
SE0401762D0 (sv)	2004-07-05	2004-07-05	Astrazeneca Ab	Novel compounds
SE0401763D0 (sv) *	2004-07-05	2004-07-05	Astrazeneca Ab	Compounds
JP2008512463A (ja) *	2004-09-08	2008-04-24	ボーイズタウンナショナルリサーチホスピタル	マトリックスメタロプロテイナーゼ−１２に関連する糸球体基底膜疾患の治療
US7951805B2 (en)	2004-09-20	2011-05-31	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase
EP1830837B1 (fr) *	2004-09-20	2013-09-04	Xenon Pharmaceuticals Inc.	Derives heterocycliques pour le traitement de maladies induites par des enzymes stearoyl-coadesaturases
JP5043668B2 (ja)	2004-09-20	2012-10-10	ゼノン・ファーマシューティカルズ・インコーポレイテッド	複素環誘導体および治療薬としてのそれらの使用
JP4958785B2 (ja)	2004-09-20	2012-06-20	ゼノン・ファーマシューティカルズ・インコーポレイテッド	複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼインヒビターとしてのそれらの使用
BRPI0515500A (pt)	2004-09-20	2008-07-29	Xenon Pharmaceuticals Inc	derivados piridazina para inibição de estearoil-coa-desaturase
EP2266569A3 (fr)	2004-09-20	2011-03-09	Xenon Pharmaceuticals Inc.	Dérivés hétérocycliques et leur utilisation en tant qu'inhibiteurs de la stearoyl-coa desaturase
JP2008513515A (ja)	2004-09-20	2008-05-01	ゼノン・ファーマシューティカルズ・インコーポレイテッド	複素環誘導体および治療薬としてのそれらの使用
GB0427403D0 (en) *	2004-12-15	2005-01-19	Astrazeneca Ab	Novel compounds I
SE0403086D0 (sv) *	2004-12-17	2004-12-17	Astrazeneca Ab	Compounds
SE0403085D0 (sv) *	2004-12-17	2004-12-17	Astrazeneca Ab	Novel componds
WO2006099598A2 (fr) *	2005-03-16	2006-09-21	Sensus Metering Systems Inc.	Procede, systeme, appareil et programme informatique permettant de determiner un emplacement physique d'un capteur
AU2006343359A1 (en)	2005-06-03	2007-11-15	Xenon Pharmaceuticals Inc.	Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors
WO2007078335A2 (fr) *	2005-12-21	2007-07-12	Decode Genetics, Ehf.	Inhibiteurs de biaryl-azote-heterocycle de lta4h pour traiter l'inflammation
AR059036A1 (es)	2006-01-17	2008-03-12	Schering Corp	Compuestos para el tratamiento de trastornos inflamatorios
TW200800954A (en) *	2006-03-16	2008-01-01	Astrazeneca Ab	Novel crystal modifications
TW200740769A (en) *	2006-03-16	2007-11-01	Astrazeneca Ab	Novel process
KR101293500B1 (ko) *	2006-05-12	2013-08-07	에스체아 히기에너 프로덕츠 악티에볼라그	신축성 라미네이트 및 신축성 라미네이트 제조 방법
CA2650268A1 (fr) *	2006-05-12	2007-11-22	Sca Hygiene Products Ab	Article absorbant de type culotte et procede de production d'articles absorbants de type culotte
WO2008053199A1 (fr) *	2006-10-30	2008-05-08	Astrazeneca Ab	Thérapie combinée pour traiter des maladies respiratoire
TW200831488A (en) *	2006-11-29	2008-08-01	Astrazeneca Ab	Novel compounds
GB0702456D0 (en)	2007-02-08	2007-03-21	Astrazeneca Ab	New combination
WO2009007747A2 (fr) *	2007-07-11	2009-01-15	Astrazeneca Ab	Nouveaux composés
US20100262110A1 (en)	2007-11-14	2010-10-14	Sca Hygiene Products Ab	Method of producing an absorbent garment, and an absorbent garment produced according to the method
US8303561B2 (en)	2007-11-14	2012-11-06	Sca Hygiene Products Ab	Method of producing an absorbent garment, and an absorbent garment produced according to the method
FR2927330B1 (fr) *	2008-02-07	2010-02-19	Sanofi Aventis	Derives de 5,6-bisaryl-2-pyridine-carboxamide, leur preparation et leur application en therapeutique comme antagonistes des recepteurs a l'urotensine ii
BRPI0911612A2 (pt)	2008-04-28	2015-12-15	Revalesio Corp	composições e métodos para o tratamento da esclerose múltipla.
FR2944524B1 (fr)	2009-04-17	2012-11-30	Ipsen Pharma Sas	Derives d'imidazolidine-2,4-dione et leur utilisation comme medicament
ES2525353T3 (es) *	2009-04-28	2014-12-22	Chugai Seiyaku Kabushiki Kaisha	Derivado de espiroimidazolona
GB0913345D0 (en)	2009-07-31	2009-09-16	Astrazeneca Ab	New combination 802
WO2011054734A1 (fr) *	2009-11-06	2011-05-12	Basf Se	Catalyseur hétérogène contenant du fer et du manganèse et procédé de fabrication d'oléfines par réaction de monoxyde de carbone avec de l'hydrogène
WO2011061527A1 (fr)	2009-11-17	2011-05-26	Astrazeneca Ab	Combinaisons qui comprennent un modulateur du récepteur glucocorticoïde, destinées au traitement de maladies respiratoires
WO2011073662A1 (fr)	2009-12-17	2011-06-23	Astrazeneca Ab	Association d'une benzoxazinone et d'un autre agent pour le traitement de maladies respiratoires
US20110202284A1 (en) *	2010-02-10	2011-08-18	Mcreynolds Cristopher	Novel groups of biomarkers for diagnosing alzheimer's disease
KR20130087002A (ko)	2010-06-04	2013-08-05	알바니 몰레큘라 리써치, 인크.	글리신 수송체-1 저해제, 그의 제조 방법 및 그의 용도
GB201021992D0 (en)	2010-12-23	2011-02-02	Astrazeneca Ab	Compound
GB201021979D0 (en)	2010-12-23	2011-02-02	Astrazeneca Ab	New compound
RU2639145C2 (ru) *	2012-09-04	2017-12-20	Шанхай Хэнжуй Фармасьютикал Ко., Лтд.	Производные оксотиоимидазолидина, способы их получения и их применение в медицине в качестве ингибиторов андрогенного рецептора
MY178583A (en)	2012-12-10	2020-10-16	Chugai Pharmaceutical Co Ltd	Hydantoin derivative
MX2016006147A (es) *	2013-11-13	2016-12-09	Hankkija Oy	Suplemento alimenticio.
JP6227149B2 (ja) *	2013-12-31	2017-11-08	イプセンファルマソシエテパールアクシオンサンプリフィエＩｐｓｅｎＰｈａｒｍａＳ．Ａ．Ｓ．	新規のイミダゾリジン−２，４−ジオン誘導体
EP2907512A1 (fr)	2014-02-14	2015-08-19	Commissariat A L'energie Atomique Et Aux Energies Alternatives	Inhibiteurs de MMP-12 en tant qu'agents antiviraux
CA2949023C (fr)	2014-06-09	2021-10-12	Hiroshi Noda	Composition pharmaceutique contenant un derive d'hydantoine
KR102134171B1 (ko)	2014-10-24	2020-07-15	란도스 바이오파마, 인크.	란티오닌 합성효소 c-유사 2-계 치료제
JO3501B1 (ar)	2014-12-22	2020-07-05	Servier Lab	مشتقات 5-{(بيبرازين - 1-يل)-3-أوكسو - بروبيل}- إيميدازوليدين-2، 4 - دايون كمثبطات ل adamts لمعالجة هشاشة العظام)
CN109803961B (zh) *	2016-09-23	2021-03-23	科研制药株式会社	(r)-5-(3,4-二氟苯基)-5-[(3-甲基-2-氧代吡啶-1(2h)-基)甲基]咪唑烷-2,4-二酮的制造方法及用于该制造的中间体
WO2021011720A2 (fr) *	2019-07-18	2021-01-21	Avidence Therapeutics, Inc.	Composés anti-ostéoarthrite ainsi que compositions et méthodes associées
AU2020381485A1 (en)	2019-11-14	2022-06-16	Foresee Pharmaceuticals Usa, Inc.	Matrix metalloproteinase (MMP) inhibitors and methods of use thereof
BR112022002387A2 (pt)	2019-12-20	2022-09-06	Landos Biopharma Inc	Composto da fórmula z-y-q-y' ou um sal ou éster farmaceuticamente aceitável do mesmo
EP4171553A1 (fr)	2020-06-26	2023-05-03	The University Of Birmingham	Inhibition de mmp-9 et mmp-12 pour le traitement d'une lésion de la moelle épinière ou d'une lésion associée à un tissu neurologique
WO2022007866A1 (fr) *	2020-07-09	2022-01-13	深圳信立泰药业股份有限公司	Dérivé tricyclique condensé, son procédé de préparation et son application pharmaceutique
CN112574193B (zh) *	2020-12-31	2022-05-17	南京医科大学	一类口服gsnor抑制剂及其药物用途

Family Cites Families (94)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2327890A (en) *	1940-04-17	1943-08-24	Parke Davis & Co	Substituted phenoxyalkyl ethers
US2745875A (en) *	1953-06-30	1956-05-15	Hoechst Ag	Preparation of nu-acylamino-phenylpropane diols
US3452040A (en)	1966-01-05	1969-06-24	American Home Prod	5,5-disubstituted hydantoins
US3529019A (en) *	1968-04-23	1970-09-15	Colgate Palmolive Co	Alkylaryloxy alanines
CS152617B1 (fr)	1970-12-29	1974-02-22
CS151744B1 (fr)	1971-01-19	1973-11-19
US3849574A (en)	1971-05-24	1974-11-19	Colgate Palmolive Co	Alpha-substituted-beta-arylthioalkyl amino-acids,for increasing heart rate
US4315031A (en) *	1977-09-01	1982-02-09	Science Union Et Cie	Thiosubstituted amino acids
GB1601310A (en)	1978-05-23	1981-10-28	Lilly Industries Ltd	Aryl hydantoins
JPS6172762A (ja)	1984-09-17	1986-04-14	Kanegafuchi Chem Ind Co Ltd	光学活性ヒダントイン類の製造法
JPS61212292A (ja) *	1985-03-19	1986-09-20	Mitsui Toatsu Chem Inc	Ｄ−α−アミノ酸の製造方法
CA1325222C (fr)	1985-08-23	1993-12-14	Lederle (Japan), Ltd.	Procede pour la production d'acide 4-biphenylylacetique
GB8618559D0 (en)	1986-07-30	1986-09-10	Genetics Int Inc	Rhodococcus bacterium
JPH0279879A (ja)	1988-09-17	1990-03-20	Canon Inc	画像形成装置
US4983771A (en)	1989-09-18	1991-01-08	Hexcel Corporation	Method for resolution of D,L-alpha-phenethylamine with D(-)mandelic acid
NL9000386A (nl)	1990-02-16	1991-09-16	Stamicarbon	Werkwijze voor de bereiding van optisch aktief aminozuuramide.
DK161690D0 (da)	1990-07-05	1990-07-05	Novo Nordisk As	Fremgangsmaade til fremstilling af enantiomere forbindelser
IL99957A0 (en)	1990-11-13	1992-08-18	Merck & Co Inc	Piperidinylcamphorsulfonyl oxytocin antagonists and pharmaceutical compositions containing them
PH31245A (en) *	1991-10-30	1998-06-18	Janssen Pharmaceutica Nv	1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives.
US5308853A (en) *	1991-12-20	1994-05-03	Warner-Lambert Company	Substituted-5-methylidene hydantoins with AT1 receptor antagonist properties
US5246943A (en) *	1992-05-19	1993-09-21	Warner-Lambert Company	Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties
NL9201230A (nl)	1992-07-09	1994-02-01	Dsm Nv	Werkwijze voor de bereiding van optisch aktief methionineamide.
EP0640594A1 (fr)	1993-08-23	1995-03-01	Fujirebio Inc.	Dérivé de hydantoine comme inhibiteur de métalloprotease
JPH07105549A (ja)	1993-09-30	1995-04-21	Canon Inc	光学的情報記録再生方法及び光学的情報記録再生装置
CA2174650A1 (fr)	1993-11-16	1995-05-26	Mark G. Bock	Antagonistes piperidinylcamphresulfonyles de l'oxytocine
RU2126404C1 (ru)	1994-01-31	1999-02-20	Пфайзер Инк.	3r, 4s -3-[4-(4-фторфенил-4-гидроксипиперидин-1-ил] хроман- 4,7-диол, его оптические изомеры и фармацевтическая композиция на его основе и способы лечения
DE69534213T2 (de)	1994-10-25	2006-01-12	Astrazeneca Ab	Therapeutisch wirksame Heterocyclen
ZA96211B (en)	1995-01-12	1996-07-26	Teva Pharma	Compositions containing and methods of using 1- aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives
US5863949A (en)	1995-03-08	1999-01-26	Pfizer Inc	Arylsulfonylamino hydroxamic acid derivatives
US6166041A (en)	1995-10-11	2000-12-26	Euro-Celtique, S.A.	2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
CZ291337B6 (cs)	1995-11-22	2003-02-12	Darwin Discovery Limited	Merkaptoalkylpeptidylová sloučenina, její použití pro výrobu přípravku pro léčení nebo prevenci stavu souvisejícího s metalloproteinázou nebo TNFalfa a farmaceutický přípravek ji obsahující
GB9616643D0 (en)	1996-08-08	1996-09-25	Chiroscience Ltd	Compounds
US5919790A (en) *	1996-10-11	1999-07-06	Warner-Lambert Company	Hydroxamate inhibitors of interleukin-1β converting enzyme
WO1998017645A1 (fr) *	1996-10-22	1998-04-30	Pharmacia & Upjohn Company	ACIDES α-AMINO SULFONYLE HYDROXAMIQUES EN TANT QU'INHIBITEURS DE METALLOPROTEINASE DE MATRICE
EP0983239A1 (fr)	1997-05-06	2000-03-08	Novo Nordisk A/S	Nouveaux composes heterocycliques
DK0877019T3 (da)	1997-05-09	2002-04-08	Hoechst Ag	Substituerede diaminocarboxylsyrer
TR199903148T2 (xx)	1997-06-21	2000-04-21	Roche Diagnostics Gmbh	Antimetastatik ve antit�m�r etkinli�i olan barbit�rik asit t�revleri.
DE19726427A1 (de)	1997-06-23	1998-12-24	Boehringer Mannheim Gmbh	Pyrimidin-2,4,6-trion-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
ES2189207T3 (es)	1997-07-31	2003-07-01	Abbott Lab	Inhibidores de hidroxamatos inversos de metaloproteinasas matriciales.
TW514634B (en)	1997-10-14	2002-12-21	Lilly Co Eli	Process to make chiral compounds
DK1030836T3 (da) *	1997-11-12	2003-05-26	Darwin Discovery Ltd	Hydroxam- og carboxylsyrederivater der har MMP- og TNF-inhiberende aktivitet
BR9909322A (pt)	1998-02-04	2000-12-05	Novartis Ag	Derivados de sulfonilamino que inibem metaloproteinases de degradação de matriz
US6329418B1 (en) *	1998-04-14	2001-12-11	The Procter & Gamble Company	Substituted pyrrolidine hydroxamate metalloprotease inhibitors
EP1077974A1 (fr)	1998-05-14	2001-02-28	Du Pont Pharmaceuticals Company	Acides hydroxamiques a substitution aryle en tant qu'inhibiteurs de metalloproteinase
CN1295561A (zh)	1998-06-03	2001-05-16	Gpinil控股公司	N－杂环羧酸或羧酸等排物的n－结合氨磺酰
US6429213B1 (en)	1998-06-17	2002-08-06	Bristol Myers Squibb Pharma Co	Cyclic hydroxamic acids as metalloproteinase inhibitors
FR2782082B3 (fr)	1998-08-05	2000-09-22	Sanofi Sa	Formes cristallines de (r)-(+)-n-[[3-[1-benzoyl-3-(3,4- dichlorophenyl)piperidin-3-yl]prop-1-yl]-4-phenylpiperidin-4 -yl]-n-methylacetamide (osanetant) et procede pour la preparation dudit compose
US6339101B1 (en)	1998-08-14	2002-01-15	Gpi Nil Holdings, Inc.	N-linked sulfonamides of N-heterocyclic carboxylic acids or isosteres for vision and memory disorders
JP2000127349A (ja) *	1998-08-21	2000-05-09	Komori Corp	凹版印刷機
WO2000012477A1 (fr)	1998-08-29	2000-03-09	British Biotech Pharmaceuticals Limited	Derives d'acide hydroxamique comme inhibiteurs de proteinase
GB9919776D0 (en)	1998-08-31	1999-10-27	Zeneca Ltd	Compoujnds
CA2346288A1 (fr)	1998-10-07	2000-04-13	Yazaki Corporation	Procede sol-gel utilisant un moule poreux
ATE260255T1 (de)	1998-11-05	2004-03-15	Pfizer Prod Inc	5-oxo-pyrrolidine-2-carbonsäure- hydroxamidderivate
BR9916363A (pt)	1998-12-18	2001-12-11	Axys Pharm Inc	Composto, composição farmacêutica e método paratratar ou prevenir um distúrbio tromboembólico
WO2000040577A1 (fr) *	1998-12-31	2000-07-13	Aventis Pharmaceuticals Inc.	Derives de 1-carboxymethyl-2-oxo-azepan utilises comme inhibiteurs selectifs de mmp-12
US6340691B1 (en)	1999-01-27	2002-01-22	American Cyanamid Company	Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors
CZ20012714A3 (cs)	1999-01-28	2002-08-14	Chugai Seiyaku Kabushiki Kaisha	Substituované deriváty fenetylaminu
US6294694B1 (en)	1999-06-04	2001-09-25	Wisconsin Alumni Research Foundation	Matrix metalloproteinase inhibitors and method of using same
GB9916562D0 (en) *	1999-07-14	1999-09-15	Pharmacia & Upjohn Spa	3-Arylsulfonyl-2-(substituted-methyl) propanoic acid derivatives as matrix metalloproteinase inhibitora
US20020006920A1 (en)	1999-07-22	2002-01-17	Robinson Ralph Pelton	Arylsulfonylamino hydroxamic acid derivatives
US6266453B1 (en)	1999-07-26	2001-07-24	Computerized Medical Systems, Inc.	Automated image fusion/alignment system and method
ES2258431T3 (es)	1999-08-02	2006-09-01	F. Hoffmann-La Roche Ag	Proceso para la preparacion de derivados de benzotiofeno.
US7034049B1 (en)	1999-08-12	2006-04-25	Pharmacia Italia S.P.A.	3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents
JP3710964B2 (ja)	1999-08-26	2005-10-26	富士通株式会社	ディスプレイデバイスのレイアウト設計方法
SE9904044D0 (sv)	1999-11-09	1999-11-09	Astra Ab	Compounds
US6525202B2 (en)	2000-07-17	2003-02-25	Wyeth	Cyclic amine phenyl beta-3 adrenergic receptor agonists
CA2419008A1 (fr)	2000-08-11	2003-02-11	Kaken Pharmaceutical Co., Ltd.	Derives de l'acide 2,3-diphenylpropionique ou leurs sels, medicaments ou inhibiteurs d'adhesion cellulaire en contenant, et leur utilisation
US20020065219A1 (en)	2000-08-15	2002-05-30	Naidu B. Narasimhulu	Water soluble thiazolyl peptide derivatives
WO2002020515A1 (fr)	2000-09-08	2002-03-14	Abbott Laboratories	Agents antibacteriens a l'oxazolidinone
US20020091107A1 (en) *	2000-09-08	2002-07-11	Madar David J.	Oxazolidinone antibacterial agents
EP1191024A1 (fr)	2000-09-22	2002-03-27	Harald Tschesche	Thiadiazines et leur utilisation comme inhibiteurs de métalloproteinases
SE0100903D0 (sv)	2001-03-15	2001-03-15	Astrazeneca Ab	Compounds
US20040147573A1 (en)	2001-03-15	2004-07-29	Anders Eriksson	Metalloproteinase inhibitors
SE0100902D0 (sv)	2001-03-15	2001-03-15	Astrazeneca Ab	Compounds
JP2004535411A (ja) *	2001-05-25	2004-11-25	ブリストルーマイヤーズスクイブカンパニー	マトリックスメタロプロテナーゼ及び／またはＴＮＦ−α転換酵素（ＴＡＣＥ）の阻害剤としてのヒダントイン及び関連複素環化合物
GB0114004D0 (en)	2001-06-08	2001-08-01	Glaxo Group Ltd	Chemical compounds
SE0103710D0 (sv)	2001-11-07	2001-11-07	Astrazeneca Ab	Compounds
CA2486350A1 (fr)	2002-06-05	2003-12-24	Kaneka Corporation	Procede de production d'un derive .alpha.-methylcysteine optiquement actif
SE0202539D0 (sv)	2002-08-27	2002-08-27	Astrazeneca Ab	Compounds
SE0202693D0 (sv)	2002-09-11	2002-09-11	Astrazeneca Ab	Compounds
SE0202692D0 (sv)	2002-09-11	2002-09-11	Astrazeneca Ab	Compounds
GB0221250D0 (en)	2002-09-13	2002-10-23	Astrazeneca Ab	Compounds
GB0221246D0 (en)	2002-09-13	2002-10-23	Astrazeneca Ab	Compounds
US6890913B2 (en) *	2003-02-26	2005-05-10	Food Industry Research And Development Institute	Chitosans
US20040266832A1 (en)	2003-06-26	2004-12-30	Li Zheng J.	Crystal forms of 2-(3-difluoromethyl-5-phenyl-pyrazol-1-yl)-5-methanesulfonyl pyridine
TWI220073B (en) *	2003-07-24	2004-08-01	Au Optronics Corp	Method for manufacturing polysilicon film
SE0401762D0 (sv)	2004-07-05	2004-07-05	Astrazeneca Ab	Novel compounds
SE0401763D0 (sv)	2004-07-05	2004-07-05	Astrazeneca Ab	Compounds
US7648992B2 (en) *	2004-07-05	2010-01-19	Astrazeneca Ab	Hydantoin derivatives for the treatment of obstructive airway diseases
SE0403086D0 (sv) *	2004-12-17	2004-12-17	Astrazeneca Ab	Compounds
SE0403085D0 (sv)	2004-12-17	2004-12-17	Astrazeneca Ab	Novel componds
TW200740769A (en)	2006-03-16	2007-11-01	Astrazeneca Ab	Novel process
TW200800954A (en)	2006-03-16	2008-01-01	Astrazeneca Ab	Novel crystal modifications
TW200831488A (en) *	2006-11-29	2008-08-01	Astrazeneca Ab	Novel compounds

2001
- 2001-03-15 SE SE0100902A patent/SE0100902D0/xx unknown
2002
- 2002-03-13 EP EP02704032A patent/EP1370534A1/fr not_active Withdrawn
- 2002-03-13 RU RU2003127733/04A patent/RU2285695C2/ru not_active IP Right Cessation
- 2002-03-13 EP EP02704031A patent/EP1370556B1/fr not_active Expired - Lifetime
- 2002-03-13 EE EEP200300451A patent/EE05364B1/xx not_active IP Right Cessation
- 2002-03-13 WO PCT/SE2002/000478 patent/WO2002074751A1/fr active Application Filing
- 2002-03-13 MX MXPA03008191A patent/MXPA03008191A/es active IP Right Grant
- 2002-03-13 DE DE60213216T patent/DE60213216T2/de not_active Expired - Lifetime
- 2002-03-13 DK DK02704031T patent/DK1370556T3/da active
- 2002-03-13 CN CNA200910147512XA patent/CN101602731A/zh active Pending
- 2002-03-13 IL IL15765702A patent/IL157657A0/xx unknown
- 2002-03-13 JP JP2002573760A patent/JP4390457B2/ja not_active Expired - Fee Related
- 2002-03-13 CA CA2440473A patent/CA2440473C/fr not_active Expired - Fee Related
- 2002-03-13 WO PCT/SE2002/000472 patent/WO2002074767A1/fr active IP Right Grant
- 2002-03-13 PL PL364706A patent/PL205315B1/pl not_active IP Right Cessation
- 2002-03-13 HU HU0400194A patent/HUP0400194A3/hu unknown
- 2002-03-13 BR BR0207984-4A patent/BR0207984A/pt not_active IP Right Cessation
- 2002-03-13 HU HU0400327A patent/HUP0400327A3/hu unknown
- 2002-03-13 UA UA2003098168A patent/UA77408C2/uk unknown
- 2002-03-13 MX MXPA03008177A patent/MXPA03008177A/es active IP Right Grant
- 2002-03-13 MY MYPI20020910A patent/MY136789A/en unknown
- 2002-03-13 EE EEP200300449A patent/EE200300449A/xx unknown
- 2002-03-13 US US10/471,900 patent/US7427631B2/en not_active Expired - Fee Related
- 2002-03-13 CN CNB02809915XA patent/CN100526307C/zh not_active Expired - Fee Related
- 2002-03-13 PT PT02704031T patent/PT1370556E/pt unknown
- 2002-03-13 SI SI200230386T patent/SI1370556T1/sl unknown
- 2002-03-13 EP EP02704037A patent/EP1370537B1/fr not_active Expired - Lifetime
- 2002-03-13 US US10/471,810 patent/US7368465B2/en not_active Expired - Fee Related
- 2002-03-13 AT AT06008158T patent/ATE493406T1/de not_active IP Right Cessation
- 2002-03-13 WO PCT/SE2002/000473 patent/WO2002074748A1/fr active IP Right Grant
- 2002-03-13 DE DE60238794T patent/DE60238794D1/de not_active Expired - Lifetime
- 2002-03-13 ES ES02704031T patent/ES2267986T3/es not_active Expired - Lifetime
- 2002-03-13 AT AT02704031T patent/ATE333454T1/de active
- 2002-03-13 IL IL15765202A patent/IL157652A0/xx unknown
- 2002-03-13 CZ CZ20032499A patent/CZ20032499A3/cs unknown
- 2002-03-13 JP JP2002573776A patent/JP2004527515A/ja not_active Withdrawn
- 2002-03-13 MX MXPA03008181A patent/MXPA03008181A/es unknown
- 2002-03-13 BR BR0208104-0A patent/BR0208104A/pt not_active IP Right Cessation
- 2002-03-13 JP JP2002573757A patent/JP2004523581A/ja active Pending
- 2002-03-13 PL PL02364707A patent/PL364707A1/xx not_active Application Discontinuation
- 2002-03-13 NZ NZ528106A patent/NZ528106A/en not_active IP Right Cessation
- 2002-03-13 AT AT02704037T patent/ATE484496T1/de not_active IP Right Cessation
- 2002-03-13 US US10/471,500 patent/US20040106659A1/en not_active Abandoned
- 2002-03-13 IL IL15765602A patent/IL157656A0/xx unknown
- 2002-03-13 CN CNB028097882A patent/CN1304377C/zh not_active Expired - Fee Related
- 2002-03-13 KR KR10-2003-7011981A patent/KR20030082986A/ko not_active IP Right Cessation
- 2002-03-13 RU RU2003127735/04A patent/RU2293729C2/ru not_active IP Right Cessation
- 2002-03-13 DE DE60237965T patent/DE60237965D1/de not_active Expired - Lifetime
- 2002-03-13 KR KR1020087017665A patent/KR100879905B1/ko not_active IP Right Cessation
- 2002-03-13 EE EEP200300445A patent/EE05431B1/xx not_active IP Right Cessation
- 2002-03-13 NZ NZ528140A patent/NZ528140A/en not_active IP Right Cessation
- 2002-03-13 AU AU2002237626A patent/AU2002237626B2/en not_active Ceased
- 2002-03-13 UA UA2003098171A patent/UA78502C2/uk unknown
- 2002-03-13 CZ CZ20032497A patent/CZ20032497A3/cs unknown
- 2002-03-13 HU HU0400202A patent/HUP0400202A3/hu unknown
- 2002-03-13 BR BR0207983-6A patent/BR0207983A/pt not_active IP Right Cessation
- 2002-03-13 SK SK1095-2003A patent/SK10952003A3/sk not_active Application Discontinuation
- 2002-03-13 SK SK1096-2003A patent/SK287766B6/sk not_active IP Right Cessation
- 2002-03-13 SK SK1092-2003A patent/SK287834B6/sk not_active IP Right Cessation
- 2002-03-13 CA CA2440630A patent/CA2440630C/fr not_active Expired - Fee Related
- 2002-03-13 KR KR1020037011987A patent/KR100886315B1/ko not_active IP Right Cessation
- 2002-03-13 UA UA2003098170A patent/UA77667C2/uk unknown
- 2002-03-13 MY MYPI20020904A patent/MY136141A/en unknown
- 2002-03-13 RU RU2003127734/04A patent/RU2288228C2/ru not_active IP Right Cessation
- 2002-03-13 ES ES02704037T patent/ES2352246T3/es not_active Expired - Lifetime
- 2002-03-13 ES ES06008158T patent/ES2357138T3/es not_active Expired - Lifetime
- 2002-03-13 CZ CZ20032500A patent/CZ20032500A3/cs unknown
- 2002-03-13 KR KR10-2003-7011982A patent/KR20030082987A/ko not_active Application Discontinuation
- 2002-03-13 CN CNB02810093XA patent/CN1269804C/zh not_active Expired - Fee Related
- 2002-03-13 NZ NZ528107A patent/NZ528107A/en unknown
- 2002-03-13 CN CN2006101061525A patent/CN1962641B/zh not_active Expired - Fee Related
- 2002-03-13 PL PL02365099A patent/PL365099A1/xx unknown
- 2002-03-13 CA CA002440631A patent/CA2440631A1/fr not_active Abandoned
- 2002-03-13 AU AU2002237632A patent/AU2002237632B2/en not_active Ceased
- 2002-03-13 EP EP06008158A patent/EP1676846B1/fr not_active Expired - Lifetime
- 2002-03-15 AR ARP020100944A patent/AR035443A1/es active IP Right Grant
- 2002-03-15 AR ARP020100943A patent/AR035695A1/es unknown
2003
- 2003-08-28 ZA ZA200306732A patent/ZA200306732B/en unknown
- 2003-08-28 IL IL157652A patent/IL157652A/en not_active IP Right Cessation
- 2003-08-28 ZA ZA200306734A patent/ZA200306734B/en unknown
- 2003-08-28 IL IL157656A patent/IL157656A/en not_active IP Right Cessation
- 2003-08-28 ZA ZA200306731A patent/ZA200306731B/en unknown
- 2003-08-28 ZA ZA200306737A patent/ZA200306737B/en unknown
- 2003-09-09 IS IS6943A patent/IS6943A/is unknown
- 2003-09-09 IS IS6942A patent/IS6942A/is unknown
- 2003-09-10 IS IS6946A patent/IS6946A/is unknown
- 2003-09-12 NO NO20034044A patent/NO20034044L/no unknown
- 2003-09-12 NO NO20034045A patent/NO327114B1/no not_active IP Right Cessation
- 2003-09-12 NO NO20034042A patent/NO326087B1/no not_active IP Right Cessation
2004
- 2004-04-21 HK HK06112181.8A patent/HK1091492A1/xx not_active IP Right Cessation
- 2004-04-21 HK HK04102796A patent/HK1059932A1/xx not_active IP Right Cessation
- 2004-04-23 HK HK04102888.7A patent/HK1060121A1/xx not_active IP Right Cessation
2006
- 2006-10-13 CY CY20061101477T patent/CY1107525T1/el unknown
2007
- 2007-10-30 US US11/928,040 patent/US7625934B2/en not_active Expired - Fee Related
2008
- 2008-05-05 US US12/114,901 patent/US7666892B2/en not_active Expired - Fee Related
- 2008-05-06 US US12/115,785 patent/US7754750B2/en not_active Expired - Fee Related
2009
- 2009-11-09 JP JP2009256358A patent/JP5140058B2/ja not_active Expired - Fee Related
2010
- 2010-01-26 US US12/693,852 patent/US8153673B2/en not_active Expired - Fee Related
- 2010-07-06 US US12/830,763 patent/US20110003853A1/en not_active Abandoned

Also Published As

Publication number	Publication date
JP2004523583A (ja)	2004-08-05
KR20030082986A (ko)	2003-10-23
EP1370556A1 (fr)	2003-12-17
KR20080071210A (ko)	2008-08-01
UA77667C2 (en)	2007-01-15
ES2267986T3 (es)	2007-03-16
NO20034042L (no)	2003-11-10
IL157656A0 (en)	2004-03-28
SK287766B6 (sk)	2011-09-05
CN1509286A (zh)	2004-06-30
US20080262045A1 (en)	2008-10-23
ZA200306737B (en)	2004-11-29
NZ528106A (en)	2005-03-24
IL157652A (en)	2010-11-30
AR035695A1 (es)	2004-06-23
IL157652A0 (en)	2004-03-28
IL157656A (en)	2010-11-30
JP5140058B2 (ja)	2013-02-06
ES2352246T3 (es)	2011-02-16
WO2002074767A1 (fr)	2002-09-26
CN1269804C (zh)	2006-08-16
ES2357138T3 (es)	2011-04-19
RU2285695C2 (ru)	2006-10-20
UA78502C2 (en)	2007-04-10
CA2440630C (fr)	2011-09-27
MXPA03008191A (es)	2004-01-29
HUP0400202A3 (en)	2004-10-28
HK1059932A1 (en)	2004-07-23
NO20034044L (no)	2003-11-10
IS6943A (is)	2003-09-09
SK10962003A3 (sk)	2004-03-02
CA2440630A1 (fr)	2002-09-26
CN1509272A (zh)	2004-06-30
US20040106659A1 (en)	2004-06-03
AU2002237626B2 (en)	2007-05-17
ZA200306732B (en)	2004-11-29
DE60238794D1 (de)	2011-02-10
EP1370537A1 (fr)	2003-12-17
JP2010077137A (ja)	2010-04-08
EP1676846B1 (fr)	2010-12-29
CN1304377C (zh)	2007-03-14
PL364707A1 (en)	2004-12-13
RU2003127733A (ru)	2005-03-20
EE05431B1 (et)	2011-06-15
NO20034045D0 (no)	2003-09-12
PL365099A1 (en)	2004-12-27
HUP0400327A2 (hu)	2005-01-28
EE05364B1 (et)	2010-12-15
ZA200306734B (en)	2004-11-29
EE200300449A (et)	2003-12-15
DE60237965D1 (en)	2010-11-25
NO20034044D0 (no)	2003-09-12
PL364706A1 (en)	2004-12-13
KR20030082989A (ko)	2003-10-23
BR0208104A (pt)	2004-03-02
SE0100902D0 (sv)	2001-03-15
HUP0400194A2 (hu)	2004-07-28
US7754750B2 (en)	2010-07-13
WO2002074748A8 (fr)	2004-04-22
US7666892B2 (en)	2010-02-23
CN1962641A (zh)	2007-05-16
EP1676846A3 (fr)	2006-07-26
SK10952003A3 (sk)	2004-05-04
ATE484496T1 (de)	2010-10-15
ZA200306731B (en)	2004-11-29
CY1107525T1 (el)	2013-03-13
MXPA03008177A (es)	2003-12-12
CA2440473A1 (fr)	2002-09-26
ATE493406T1 (de)	2011-01-15
US7625934B2 (en)	2009-12-01
EP1370537B1 (fr)	2010-10-13
BR0207983A (pt)	2004-06-15
NO20034045L (no)	2003-11-10
CN100526307C (zh)	2009-08-12
DE60213216T2 (de)	2007-07-12
IS6942A (is)	2003-09-09
KR100886315B1 (ko)	2009-03-04
US7427631B2 (en)	2008-09-23
MY136141A (en)	2008-08-29
CZ20032497A3 (cs)	2004-02-18
SI1370556T1 (sl)	2006-10-31
CA2440473C (fr)	2011-08-30
IL157657A0 (en)	2004-03-28
EE200300451A (et)	2003-12-15
EE200300445A (et)	2003-12-15
NO326087B1 (no)	2008-09-15
PT1370556E (pt)	2006-11-30
CZ20032499A3 (cs)	2004-03-17
US20040127528A1 (en)	2004-07-01
MXPA03008181A (es)	2003-12-12
US8153673B2 (en)	2012-04-10
CN1962641B (zh)	2012-07-04
EP1370534A1 (fr)	2003-12-17
CZ20032500A3 (cs)	2004-02-18
SK10922003A3 (sk)	2004-05-04
WO2002074751A1 (fr)	2002-09-26
US7368465B2 (en)	2008-05-06
HK1060121A1 (en)	2004-07-30
ATE333454T1 (de)	2006-08-15
WO2002074748A1 (fr)	2002-09-26
BR0207984A (pt)	2004-06-15
HUP0400327A3 (en)	2005-06-28
KR100879905B1 (ko)	2009-01-21
US20080171882A1 (en)	2008-07-17
HUP0400202A2 (hu)	2004-08-30
SK287834B6 (sk)	2011-12-05
RU2293729C2 (ru)	2007-02-20
EP1370556B1 (fr)	2006-07-19
IS6946A (is)	2003-09-10
AU2002237632B2 (en)	2007-05-10
NZ528140A (en)	2005-02-25
MY136789A (en)	2008-11-28
RU2003127734A (ru)	2005-03-20
HUP0400194A3 (en)	2004-10-28
NO327114B1 (no)	2009-04-27
NO20034042D0 (no)	2003-09-12
RU2003127735A (ru)	2005-03-20
RU2288228C2 (ru)	2006-11-27
NZ528107A (en)	2005-06-24
US20080306065A1 (en)	2008-12-11
EP1676846A2 (fr)	2006-07-05
JP4390457B2 (ja)	2009-12-24
US20040138276A1 (en)	2004-07-15
CA2440631A1 (fr)	2002-09-26
HK1091492A1 (en)	2007-01-19
DK1370556T3 (da)	2006-10-30
CN1509276A (zh)	2004-06-30
KR20030082987A (ko)	2003-10-23
DE60213216D1 (en)	2006-08-31
JP2004523581A (ja)	2004-08-05
PL205315B1 (pl)	2010-04-30
CN101602731A (zh)	2009-12-16
WO2002074767A8 (fr)	2004-04-22
US20100273849A1 (en)	2010-10-28
US20110003853A1 (en)	2011-01-06
AR035443A1 (es)	2004-05-26
JP2004527515A (ja)	2004-09-09

Publication	Publication Date	Title
UA77408C2 (en)	2006-12-15	Metalloproteinase inhibitors, pharmaceutical composition on its base, and use thereof
UA74624C2 (en)	2006-01-16	Metalloproteinase inhibitors
AU2002237632A1 (en)	2003-03-27	Metalloproteinase inhibitors
EP1370536A1 (fr)	2003-12-17	Inhibiteurs de metalloproteinase
EP1444202B1 (fr)	2008-10-15	Nouveaux inhibiteurs des metalloproteinases
AU2002237629A1 (en)	2002-10-03	Metalloproteinase inhibitors