SK12872001A3 - Amínové deriváty ako inhibítory proteázy - Google Patents
Amínové deriváty ako inhibítory proteázy Download PDFInfo
- Publication number
- SK12872001A3 SK12872001A3 SK1287-2001A SK12872001A SK12872001A3 SK 12872001 A3 SK12872001 A3 SK 12872001A3 SK 12872001 A SK12872001 A SK 12872001A SK 12872001 A3 SK12872001 A3 SK 12872001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- hetero
- cycloalkyl
- aryl
- halogen
- Prior art date
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- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 4
- 150000001412 amines Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 36
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 31
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical class 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 1123
- -1 heterocycloaryl Chemical group 0.000 claims description 516
- 125000005842 heteroatom Chemical group 0.000 claims description 313
- 125000003118 aryl group Chemical group 0.000 claims description 304
- 239000001257 hydrogen Substances 0.000 claims description 285
- 229910052739 hydrogen Inorganic materials 0.000 claims description 285
- 229910052736 halogen Inorganic materials 0.000 claims description 276
- 150000002367 halogens Chemical group 0.000 claims description 276
- 150000001875 compounds Chemical class 0.000 claims description 266
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 252
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 226
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 148
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 145
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 122
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 100
- 125000001118 alkylidene group Chemical group 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 57
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
- 201000010099 disease Diseases 0.000 claims description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
- 125000004043 oxo group Chemical group O=* 0.000 claims description 47
- 125000006413 ring segment Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 125000002723 alicyclic group Chemical group 0.000 claims description 37
- 239000000651 prodrug Substances 0.000 claims description 37
- 229940002612 prodrug Drugs 0.000 claims description 37
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- 150000001721 carbon Chemical group 0.000 claims description 31
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 22
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 19
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 18
- 102000005927 Cysteine Proteases Human genes 0.000 claims description 17
- 108010005843 Cysteine Proteases Proteins 0.000 claims description 17
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 230000007170 pathology Effects 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 13
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 13
- 125000003368 amide group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 11
- 108090000613 Cathepsin S Proteins 0.000 claims description 10
- 102100035654 Cathepsin S Human genes 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 208000006673 asthma Diseases 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
- BTIIGNUPPKUQAP-UHFFFAOYSA-N [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;diperchlorate Chemical group [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 BTIIGNUPPKUQAP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 239000007943 implant Substances 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 7
- 206010006451 bronchitis Diseases 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 6
- 201000010251 cutis laxa Diseases 0.000 claims description 6
- 125000004976 cyclobutylene group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000003431 oxalo group Chemical group 0.000 claims description 5
- DGOYLVBDCVINQZ-UHFFFAOYSA-N oxane-4-carboxamide Chemical compound NC(=O)C1CCOCC1 DGOYLVBDCVINQZ-UHFFFAOYSA-N 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 206010028372 Muscular weakness Diseases 0.000 claims description 4
- 241000721454 Pemphigus Species 0.000 claims description 4
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- 230000000735 allogeneic effect Effects 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000000262 estrogen Substances 0.000 claims description 4
- 229940011871 estrogen Drugs 0.000 claims description 4
- 230000028993 immune response Effects 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 230000036473 myasthenia Effects 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
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- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
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- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 3
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- 208000022256 primary systemic amyloidosis Diseases 0.000 claims description 3
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- HCSFGOUVZVXTFH-UHFFFAOYSA-N ethyl 3-[(4-chlorobenzoyl)amino]-4-(5-methylthiophen-2-yl)-4-oxobutanoate Chemical compound C=1C=C(C)SC=1C(=O)C(CC(=O)OCC)NC(=O)C1=CC=C(Cl)C=C1 HCSFGOUVZVXTFH-UHFFFAOYSA-N 0.000 claims description 2
- OUILNFYMVOYZMY-UHFFFAOYSA-N ethyl 4-[(4-fluorobenzoyl)amino]-5-oxo-5-thiophen-3-ylpentanoate Chemical compound C1=CSC=C1C(=O)C(CCC(=O)OCC)NC(=O)C1=CC=C(F)C=C1 OUILNFYMVOYZMY-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
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- 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
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- A—HUMAN NECESSITIES
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EP1309591B1 (en) | 2000-08-14 | 2007-01-24 | Ortho-McNeil Pharmaceutical, Inc. | Substituted pyrazoles |
ES2261463T3 (es) | 2000-08-14 | 2006-11-16 | Ortho-Mcneil Pharmaceutical, Inc. | Pirazoles sustituidos. |
ATE324372T1 (de) | 2000-08-14 | 2006-05-15 | Ortho Mcneil Pharm Inc | Substituierte pyrazole |
US7332494B2 (en) | 2000-08-14 | 2008-02-19 | Janssen Pharmaceutica, N.V. | Method for treating allergies using substituted pyrazoles |
US6369032B1 (en) * | 2000-09-06 | 2002-04-09 | Ortho-Mcneil Pharmaceutical, Inc. | Method for treating allergies |
US7064123B1 (en) | 2000-12-22 | 2006-06-20 | Aventis Pharmaceuticals Inc. | Compounds and compositions as cathepsin inhibitors |
US7030116B2 (en) * | 2000-12-22 | 2006-04-18 | Aventis Pharmaceuticals Inc. | Compounds and compositions as cathepsin inhibitors |
EP1397340A2 (en) * | 2001-06-01 | 2004-03-17 | Axys Pharmaceuticals, Inc. | Chemical compounds and pharmaceutical compositions as cathepsin s inhibitors |
US20040147503A1 (en) * | 2002-06-04 | 2004-07-29 | Sheila Zipfeil | Novel compounds and compositions as cathepsin inhibitors |
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HUP0401906A3 (en) * | 2001-11-14 | 2008-07-28 | Aventis Pharma Inc | Novel cathepsin s inhibitors, process for their preparation and pharmaceutical compositions containing them |
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JP2005526830A (ja) | 2002-04-16 | 2005-09-08 | アクシス・ファーマシューティカルズ・インコーポレイテッド | ヘテロアリール及び不飽和ヘテロシクロアルキルマグネシウム試薬の製造方法及び使用 |
CA2484011A1 (en) * | 2002-05-14 | 2003-11-27 | Axys Pharmaceuticals, Inc. | Cysteine protease inhibitors |
AU2003256305A1 (en) * | 2002-06-24 | 2004-01-06 | Axys Pharmaceuticals, Inc. | Peptidic compounds as cysteine protease inhibitors |
BR0314980A (pt) * | 2002-10-08 | 2005-08-09 | Scripps Research Inst | Inibidores de hidrolase de amida de ácido graxo |
NZ542865A (en) | 2003-09-18 | 2009-04-30 | Virobay Inc | Haloalkyl containing compounds as cysteine protease inhibitors |
WO2005028454A1 (en) * | 2003-09-18 | 2005-03-31 | Axys Pharmaceuticals, Inc. | Haloalkyl containing compounds as cysteine protease inhibitors |
MXPA06004422A (es) | 2003-10-24 | 2006-07-03 | Aventis Pharma Inc | Nuevos derivados de ceto-oxadiazol como inhibidores de las catepsinas. |
JP2007513972A (ja) * | 2003-12-11 | 2007-05-31 | アクシス・ファーマシューティカルズ・インコーポレイテッド | 低分子治療剤または生物製剤の投与によって引き起こされる免疫応答を治療するためのカテプシンsインヒビターの使用 |
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JP2007519744A (ja) * | 2004-01-30 | 2007-07-19 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | システインプロテアーゼインヒビターとしてのシリナン化合物。 |
JP2008521853A (ja) * | 2004-12-02 | 2008-06-26 | プロビオドルグ エージー | 神経疾患治療用の新規化合物 |
ES2400582T3 (es) | 2005-03-21 | 2013-04-10 | Virobay, Inc. | Compuestos de alfa cetoamida como inhibidores de cisteína proteasa |
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GB0910003D0 (en) | 2009-06-11 | 2009-07-22 | Univ Leuven Kath | Novel compounds for the treatment of neurodegenerative diseases |
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WO2012151319A1 (en) | 2011-05-02 | 2012-11-08 | Virobay, Inc. | Cathepsin inhibitors for the treatment of bone cancer and bone cancer pain |
EP2838534A4 (en) | 2012-04-12 | 2015-11-11 | Univ Leland Stanford Junior | SUBSTITUTED BENZAMIDES AND USES THEREOF |
WO2020201572A1 (en) | 2019-04-05 | 2020-10-08 | Université De Bretagne Occidentale | Protease-activated receptor-2 inhibitors for the treatment of sensory neuropathy induced by a marine neurotoxic poisoning |
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US6204261B1 (en) * | 1995-12-20 | 2001-03-20 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β Converting enzyme inhibitors |
US5874424A (en) * | 1995-12-20 | 1999-02-23 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β converting enzyme |
GB8809316D0 (en) | 1987-05-11 | 1988-05-25 | Ici America Inc | Heterocyclic ketones |
EP0376012A3 (en) | 1988-12-27 | 1992-05-06 | American Cyanamid Company | Renin inhibitors |
US5847135A (en) * | 1994-06-17 | 1998-12-08 | Vertex Pharmaceuticals, Incorporated | Inhibitors of interleukin-1β converting enzyme |
US5716929A (en) * | 1994-06-17 | 1998-02-10 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
US5691368A (en) | 1995-01-11 | 1997-11-25 | Hoechst Marion Roussel, Inc. | Substituted oxazolidine calpain and/or cathepsin B inhibitors |
US6022861A (en) * | 1995-06-07 | 2000-02-08 | Cor Therapeutics, Inc. | Ketoheterocyclic inhibitors of factor Xa |
US6069130A (en) | 1995-06-07 | 2000-05-30 | Cor Therapeutics, Inc. | Ketoheterocyclic inhibitors of factor Xa |
US5843904A (en) * | 1995-12-20 | 1998-12-01 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1βconverting enzyme |
NZ333696A (en) | 1996-07-08 | 2000-06-23 | Du Pont Pharm Co | Amidinoindoles, amidinoazoles, and analogs thereof as inhibitors of trypsin like protease enzymes like thrombin and Xa factor |
DZ2285A1 (fr) | 1996-08-08 | 2002-12-25 | Smithkline Beecham Corp | Inhibiteurs de protéase de la cystéine. |
EP0923535A4 (en) | 1996-08-28 | 2001-01-10 | Smithkline Beecham Corp | CYSTEINE PROTEASE INHIBITORS |
UA56197C2 (ru) | 1996-11-08 | 2003-05-15 | Зенека Лімітед | Гетероциклические производные |
US6291640B1 (en) * | 1996-12-27 | 2001-09-18 | Boehringer Ingelheim Ltd. | Peptidomimetic inhibitors of the human cytomegalovirus protease |
US6004933A (en) | 1997-04-25 | 1999-12-21 | Cortech Inc. | Cysteine protease inhibitors |
US6114310A (en) * | 1998-01-23 | 2000-09-05 | Microcide Pharmaceuticals, Inc. | Efflux pump inhibitors |
WO2000051998A1 (en) * | 1999-03-02 | 2000-09-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cathepsin s |
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2000
- 2000-03-14 TW TW092132729A patent/TW200404789A/zh unknown
- 2000-03-15 PL PL00350926A patent/PL350926A1/xx not_active Application Discontinuation
- 2000-03-15 HU HU0200572A patent/HUP0200572A3/hu unknown
- 2000-03-15 EA EA200100970A patent/EA004807B1/ru not_active IP Right Cessation
- 2000-03-15 SK SK1287-2001A patent/SK12872001A3/sk unknown
- 2000-03-15 JP JP2000605574A patent/JP2002539201A/ja active Pending
- 2000-03-15 BR BR0009044-1A patent/BR0009044A/pt not_active Application Discontinuation
- 2000-03-15 EA EA200301094A patent/EA200301094A1/ru unknown
- 2000-03-15 CZ CZ20013247A patent/CZ20013247A3/cs unknown
- 2000-03-15 IL IL14542800A patent/IL145428A0/xx active IP Right Grant
- 2000-03-15 KR KR1020017011748A patent/KR20010110670A/ko not_active Application Discontinuation
- 2000-03-15 AU AU37507/00A patent/AU774664B2/en not_active Ceased
- 2000-03-15 CN CN00805144A patent/CN1345314A/zh active Pending
- 2000-03-15 EE EEP200100486A patent/EE200100486A/xx unknown
- 2000-03-15 WO PCT/US2000/006885 patent/WO2000055144A1/en not_active Application Discontinuation
- 2000-03-15 TR TR2001/03335T patent/TR200103335T2/xx unknown
- 2000-03-15 YU YU66201A patent/YU66201A/sh unknown
- 2000-03-15 CA CA002367352A patent/CA2367352A1/en not_active Abandoned
- 2000-03-15 US US09/525,507 patent/US6576630B1/en not_active Expired - Fee Related
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- 2001-10-02 BG BG105969A patent/BG105969A/xx unknown
- 2001-10-12 HR HR20010736A patent/HRP20010736A2/hr not_active Application Discontinuation
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2003
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Also Published As
Publication number | Publication date |
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BG105969A (en) | 2002-05-31 |
CZ20013247A3 (cs) | 2002-05-15 |
CN1345314A (zh) | 2002-04-17 |
EA200100970A1 (ru) | 2002-04-25 |
JP2002539201A (ja) | 2002-11-19 |
EA200301094A1 (ru) | 2004-06-24 |
EE200100486A (et) | 2003-02-17 |
ZA200107496B (en) | 2003-02-26 |
US6576630B1 (en) | 2003-06-10 |
BR0009044A (pt) | 2002-01-15 |
WO2000055144A1 (en) | 2000-09-21 |
CA2367352A1 (en) | 2000-09-21 |
US20030232864A1 (en) | 2003-12-18 |
HRP20010736A2 (en) | 2002-12-31 |
KR20010110670A (ko) | 2001-12-13 |
IL145428A (en) | 2007-10-31 |
IL145428A0 (en) | 2002-06-30 |
TR200103335T2 (tr) | 2002-04-22 |
PL350926A1 (en) | 2003-02-10 |
HUP0200572A2 (en) | 2002-06-29 |
AU774664B2 (en) | 2004-07-01 |
EA004807B1 (ru) | 2004-08-26 |
AU3750700A (en) | 2000-10-04 |
TW200404789A (en) | 2004-04-01 |
HUP0200572A3 (en) | 2004-07-28 |
YU66201A (sh) | 2005-07-19 |
NO20014483D0 (no) | 2001-09-14 |
EP1161422A1 (en) | 2001-12-12 |
NO20014483L (no) | 2001-11-01 |
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