JP2005517640A - 置換2−アミノ−シクロアルカンカルボキサアミドならびにシステインプロテアーゼインヒビターとしてのその使用 - Google Patents
置換2−アミノ−シクロアルカンカルボキサアミドならびにシステインプロテアーゼインヒビターとしてのその使用 Download PDFInfo
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- JP2005517640A JP2005517640A JP2003549315A JP2003549315A JP2005517640A JP 2005517640 A JP2005517640 A JP 2005517640A JP 2003549315 A JP2003549315 A JP 2003549315A JP 2003549315 A JP2003549315 A JP 2003549315A JP 2005517640 A JP2005517640 A JP 2005517640A
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- Prior art keywords
- methyl
- amino
- lower alkyl
- cyclohexyl
- carbonyl
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- 239000002852 cysteine proteinase inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 102000005927 Cysteine Proteases Human genes 0.000 claims abstract description 22
- 108010005843 Cysteine Proteases Proteins 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 201000010099 disease Diseases 0.000 claims abstract description 8
- -1 furo [3,2-c] pyridinyl Chemical group 0.000 claims description 131
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 10
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
- 125000001041 indolyl group Chemical group 0.000 claims description 10
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 230000006806 disease prevention Effects 0.000 claims description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
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- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
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- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
- KNYHISBJRQVMAZ-UHFFFAOYSA-N 1h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C=NNC2=C1 KNYHISBJRQVMAZ-UHFFFAOYSA-N 0.000 claims description 4
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004615 furo[2,3-b]pyridinyl group Chemical group O1C(=CC=2C1=NC=CC2)* 0.000 claims description 4
- 125000004613 furo[2,3-c]pyridinyl group Chemical group O1C(=CC=2C1=CN=CC2)* 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- MMNDMYKGOCWEQT-RTWAWAEBSA-N n-[(1s,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]-6-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-indole-2-carboxamide Chemical compound C1CN(C)CCN1CCOC1=CC=C(C=C(N2)C(=O)N[C@@H]3[C@@H](CCCC3)C(=O)NCC#N)C2=C1 MMNDMYKGOCWEQT-RTWAWAEBSA-N 0.000 claims description 4
- YXVUQVNXKNUADU-DVKDBIPTSA-N n-[(1s,2r)-2-[[cyano(cyclopropyl)methyl]carbamoyl]cyclohexyl]-1-methylindole-2-carboxamide Chemical compound O=C([C@@H]1CCCC[C@@H]1NC(=O)C=1N(C2=CC=CC=C2C=1)C)NC(C#N)C1CC1 YXVUQVNXKNUADU-DVKDBIPTSA-N 0.000 claims description 4
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- IJDMNOPONIFIFW-HIFRSBDPSA-N n-[(1s,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]-1h-indole-2-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@@H]1NC(=O)C1=CC2=CC=CC=C2N1 IJDMNOPONIFIFW-HIFRSBDPSA-N 0.000 claims description 3
- LEQLRLCEVLBBQK-DMDYGQEQSA-N n-[(1s,2r)-2-[[(1s)-1-cyano-3-methylbutyl]carbamoyl]cyclohexyl]-1-methyl-6-(2-pyridin-2-ylethoxy)indole-2-carboxamide Chemical compound CC(C)C[C@@H](C#N)NC(=O)[C@@H]1CCCC[C@@H]1NC(=O)C(N(C1=C2)C)=CC1=CC=C2OCCC1=CC=CC=N1 LEQLRLCEVLBBQK-DMDYGQEQSA-N 0.000 claims description 3
- ZKEFMKABWCXPEB-OTWHNJEPSA-N n-[(1s,2r)-2-[[(1s)-1-cyano-3-methylbutyl]carbamoyl]cyclohexyl]-1-methylindole-2-carboxamide Chemical compound CC(C)C[C@@H](C#N)NC(=O)[C@@H]1CCCC[C@@H]1NC(=O)C1=CC2=CC=CC=C2N1C ZKEFMKABWCXPEB-OTWHNJEPSA-N 0.000 claims description 3
- YXVUQVNXKNUADU-FGTMMUONSA-N n-[(1s,2r)-2-[[(s)-cyano(cyclopropyl)methyl]carbamoyl]cyclohexyl]-1-methylindole-2-carboxamide Chemical compound C1([C@@H](C#N)NC(=O)[C@@H]2CCCC[C@@H]2NC(=O)C=2N(C3=CC=CC=C3C=2)C)CC1 YXVUQVNXKNUADU-FGTMMUONSA-N 0.000 claims description 3
- FIKTZYJAOSTYPW-FAZYOCGDSA-N n-[(1s,2r)-2-[[cyano(cyclopropyl)methyl]carbamoyl]cyclohexyl]-1h-indole-5-carboxamide Chemical compound O=C([C@H]1[C@H](CCCC1)NC(=O)C=1C=C2C=CNC2=CC=1)NC(C#N)C1CC1 FIKTZYJAOSTYPW-FAZYOCGDSA-N 0.000 claims description 3
- IDGAVOBWFVWFEV-UHFFFAOYSA-N 1-(2-hydroxyethyl)indole-2-carboxylic acid Chemical compound C1=CC=C2N(CCO)C(C(O)=O)=CC2=C1 IDGAVOBWFVWFEV-UHFFFAOYSA-N 0.000 claims description 2
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- WXOVXRUXJAYCHW-MARPTJLWSA-N n-[(1s,2r)-2-[[cyano(cyclopropyl)methyl]carbamoyl]cyclohexyl]quinoline-2-carboxamide Chemical compound O=C([C@H]1[C@H](CCCC1)NC(=O)C=1N=C2C=CC=CC2=CC=1)NC(C#N)C1CC1 WXOVXRUXJAYCHW-MARPTJLWSA-N 0.000 claims description 2
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 22
- 206010028980 Neoplasm Diseases 0.000 abstract description 18
- 206010027476 Metastases Diseases 0.000 abstract description 15
- 230000009401 metastasis Effects 0.000 abstract description 15
- 208000001132 Osteoporosis Diseases 0.000 abstract description 14
- 208000007814 Unstable Angina Diseases 0.000 abstract description 12
- 206010002388 Angina unstable Diseases 0.000 abstract description 11
- 201000004332 intermediate coronary syndrome Diseases 0.000 abstract description 11
- 230000001052 transient effect Effects 0.000 abstract description 11
- 206010061218 Inflammation Diseases 0.000 abstract description 9
- 230000004054 inflammatory process Effects 0.000 abstract description 9
- 201000004792 malaria Diseases 0.000 abstract description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract description 9
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 8
- 201000001320 Atherosclerosis Diseases 0.000 abstract description 8
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 8
- 208000002177 Cataract Diseases 0.000 abstract description 8
- 206010018364 Glomerulonephritis Diseases 0.000 abstract description 8
- 208000002223 abdominal aortic aneurysm Diseases 0.000 abstract description 8
- 238000002399 angioplasty Methods 0.000 abstract description 8
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- 208000032109 Transient ischaemic attack Diseases 0.000 abstract description 5
- 201000010875 transient cerebral ischemia Diseases 0.000 abstract description 5
- 206010010904 Convulsion Diseases 0.000 abstract description 2
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 182
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 89
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
- 235000019439 ethyl acetate Nutrition 0.000 description 61
- 239000000047 product Substances 0.000 description 50
- 239000000243 solution Substances 0.000 description 49
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 33
- 108090000625 Cathepsin K Proteins 0.000 description 31
- 102000004171 Cathepsin K Human genes 0.000 description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 31
- 239000000460 chlorine Chemical group 0.000 description 26
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
- 235000019341 magnesium sulphate Nutrition 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- 238000006243 chemical reaction Methods 0.000 description 18
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 12
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 9
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- 108010084457 Cathepsins Proteins 0.000 description 9
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
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- SVQVBAUJEKSBEC-UHFFFAOYSA-N tert-butyl n-(4-formylphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=O)C=C1 SVQVBAUJEKSBEC-UHFFFAOYSA-N 0.000 description 1
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- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
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- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33675001P | 2001-12-04 | 2001-12-04 | |
| PCT/EP2002/013221 WO2003048123A1 (en) | 2001-12-04 | 2002-11-25 | Substituted 2-amino-cycloalkanecarboxamides and their use as cysteine protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005517640A true JP2005517640A (ja) | 2005-06-16 |
| JP2005517640A5 JP2005517640A5 (enExample) | 2005-12-22 |
Family
ID=23317485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003549315A Pending JP2005517640A (ja) | 2001-12-04 | 2002-11-25 | 置換2−アミノ−シクロアルカンカルボキサアミドならびにシステインプロテアーゼインヒビターとしてのその使用 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6747053B2 (enExample) |
| EP (1) | EP1453801B1 (enExample) |
| JP (1) | JP2005517640A (enExample) |
| KR (1) | KR20050044660A (enExample) |
| CN (1) | CN1315806C (enExample) |
| AR (1) | AR037683A1 (enExample) |
| AT (1) | ATE357432T1 (enExample) |
| AU (1) | AU2002352126A1 (enExample) |
| BR (1) | BR0214642A (enExample) |
| CA (1) | CA2467435A1 (enExample) |
| DE (1) | DE60219068T2 (enExample) |
| ES (1) | ES2282497T3 (enExample) |
| GT (1) | GT200200253A (enExample) |
| HU (1) | HUP0402344A2 (enExample) |
| IL (1) | IL161992A0 (enExample) |
| MX (1) | MXPA04005263A (enExample) |
| NO (1) | NO20042719L (enExample) |
| PA (1) | PA8559701A1 (enExample) |
| PE (1) | PE20030723A1 (enExample) |
| PL (1) | PL370766A1 (enExample) |
| RU (1) | RU2004120784A (enExample) |
| TW (1) | TW200303861A (enExample) |
| UY (1) | UY27561A1 (enExample) |
| WO (1) | WO2003048123A1 (enExample) |
| ZA (1) | ZA200404343B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007080882A1 (ja) * | 2006-01-11 | 2007-07-19 | Seikagaku Corporation | オキサゾロン誘導体 |
| JP2010531344A (ja) * | 2007-06-26 | 2010-09-24 | アストラゼネカ アクチボラグ | カテプシンk阻害剤としての1−シアノシクロプロピル誘導体 |
| JP2017031199A (ja) * | 2011-07-26 | 2017-02-09 | サノフイ | 3−ヘテロアロイルアミノ−プロピオン酸誘導体及び医薬としてのそれらの使用 |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE494388T1 (de) * | 1999-01-13 | 2011-01-15 | Univ New York State Res Found | Neues verfahren zum erschaffen von proteinkinase- inhibitoren |
| US7005445B2 (en) * | 2001-10-22 | 2006-02-28 | The Research Foundation Of State University Of New York | Protein kinase and phosphatase inhibitors and methods for designing them |
| GB0128996D0 (en) | 2001-12-04 | 2002-01-23 | Novartis Ag | Organic compounds |
| ES2262996T3 (es) * | 2002-01-07 | 2006-12-01 | Eisai Co., Ltd. | Deazapurinas y sus usos. |
| SE0203712D0 (sv) | 2002-12-13 | 2002-12-13 | Astrazeneca Ab | Novel compounds |
| GB0403038D0 (en) | 2004-02-11 | 2004-03-17 | Novartis Ag | Organic compounds |
| WO2006007664A1 (en) * | 2004-07-22 | 2006-01-26 | Genomics Research Partners Pty Ltd | Agents and methods for diagnosing osteoarthritis |
| AU2006261954A1 (en) * | 2005-06-28 | 2007-01-04 | Merck & Co., Inc. | Non-nucleoside reverse transcriptase inhibitors |
| EP1749822B1 (en) * | 2005-08-05 | 2008-10-15 | Hybrigenics S.A. | Novel cysteine protease inhibitors and their therapeutic applications |
| CA2617725C (en) | 2005-08-05 | 2012-04-03 | Hybrigenics Sa | Novel cysteine protease inhibitors and their therapeutic applications |
| WO2007041775A1 (en) * | 2005-10-10 | 2007-04-19 | The University Of Queensland | Cysteine protease inhibitors incorporating azide groups |
| WO2007081530A2 (en) * | 2006-01-03 | 2007-07-19 | Med Institute, Inc. | Endoluminal medical device for local delivery of cathepsin inhibitors |
| US7838542B2 (en) * | 2006-06-29 | 2010-11-23 | Kinex Pharmaceuticals, Llc | Bicyclic compositions and methods for modulating a kinase cascade |
| CN101591327B (zh) * | 2008-05-26 | 2012-07-25 | 华东理工大学 | 苯烷酰胺类化合物及其用途 |
| KR20150048759A (ko) | 2012-09-07 | 2015-05-07 | 노파르티스 아게 | 인돌 카르복스아미드 유도체 및 그의 용도 |
| NO2699580T3 (enExample) | 2014-01-24 | 2018-02-24 | ||
| US9950989B2 (en) * | 2014-02-14 | 2018-04-24 | Toa Eiyo Ltd. | Cyclic hydrocarbon compound |
| CA3066711A1 (en) | 2017-07-31 | 2019-02-07 | Novartis Ag | Use of mavoglurant in the reduction of cocaine use or in preventing relapse into cocaine use |
| AU2019228717C1 (en) | 2018-03-01 | 2025-01-09 | Astrazeneca Ab | Pharmaceutical compositions comprising (2S)-N-{(1S)-1-cyano-2-[4-(3-methyl-2- oxo-2,3-dihydro-1,3-benzoxazol-5-yl)phenyl]ethyl}-1,4-oxazepane-2-carboxamide |
| CA3106269A1 (en) | 2018-07-17 | 2020-01-23 | Insmed Incorporated | Certain (2s)-n-[(1s)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides for treating lupus nephritis |
| BR112023003492A2 (pt) | 2020-08-26 | 2023-05-09 | Haisco Pharmaceuticals Pte Ltd | Composto de fórmula (i), composição farmacêutica e uso do composto |
| MX2023006194A (es) | 2020-12-04 | 2023-06-09 | Reistone Biopharma Company Ltd | Inhibidor de molecula peque?a de catepsina c y uso medicinal del mismo. |
| AU2023285191A1 (en) | 2022-06-07 | 2024-12-12 | Reistone Biopharma Company Limited | Pharmaceutically acceptable salt of benzo[c]chroman compound and polymorphic form and use of pharmaceutically acceptable salt |
| KR20250020509A (ko) | 2022-06-07 | 2025-02-11 | 레이스톤 바이오파마 컴퍼니 리미티드 | 벤조[c]크로만 화합물의 다형체, 이의 제조 방법 및 이의 용도 |
| CN120584108A (zh) | 2023-01-06 | 2025-09-02 | 英斯梅德股份有限公司 | 新型可逆dpp1抑制剂及其用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU177576B (en) | 1975-06-02 | 1981-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 2-amino-cyclohexane carboxylic acid,its amides and similar compounds |
| DE4417163A1 (de) | 1994-05-17 | 1995-11-23 | Hoechst Schering Agrevo Gmbh | Heterocyclylamino- und Heterocyclyloxy-cycloalkyl-Derivate, ihre Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide |
| IT1283467B1 (it) | 1996-07-19 | 1998-04-21 | Menarini Farma Ind | Derivati di cicloalcani 1,2 sostituiti come inibitori della trombina, procedimento per la loro preparazione e loro impiego in formulazioni |
| BR9813197A (pt) | 1997-11-05 | 2000-08-29 | Novartis Ag | Dipeptìdeo nitrilas |
| CN1240681C (zh) * | 1999-12-24 | 2006-02-08 | 霍夫曼-拉罗奇有限公司 | 作为组织蛋白酶k抑制剂的腈衍生物 |
| JP2003525874A (ja) | 2000-01-06 | 2003-09-02 | メルク フロスト カナダ アンド カンパニー | プロテアーゼ阻害剤としての新規化合物および組成物 |
| US6462076B2 (en) * | 2000-06-14 | 2002-10-08 | Hoffmann-La Roche Inc. | Beta-amino acid nitrile derivatives as cathepsin K inhibitors |
| AU2002352663B2 (en) | 2001-11-13 | 2007-06-21 | Axys Pharmaceuticals, Inc. | Cyanoalkylamino derivatives as protease inhibitors |
-
2002
- 2002-11-25 BR BR0214642-8A patent/BR0214642A/pt not_active IP Right Cessation
- 2002-11-25 AT AT02787799T patent/ATE357432T1/de not_active IP Right Cessation
- 2002-11-25 WO PCT/EP2002/013221 patent/WO2003048123A1/en not_active Ceased
- 2002-11-25 RU RU2004120784/04A patent/RU2004120784A/ru not_active Application Discontinuation
- 2002-11-25 CN CNB02824060XA patent/CN1315806C/zh not_active Expired - Fee Related
- 2002-11-25 EP EP02787799A patent/EP1453801B1/en not_active Expired - Lifetime
- 2002-11-25 AU AU2002352126A patent/AU2002352126A1/en not_active Abandoned
- 2002-11-25 HU HU0402344A patent/HUP0402344A2/hu unknown
- 2002-11-25 PL PL02370766A patent/PL370766A1/xx not_active Application Discontinuation
- 2002-11-25 ES ES02787799T patent/ES2282497T3/es not_active Expired - Lifetime
- 2002-11-25 KR KR1020047008481A patent/KR20050044660A/ko not_active Ceased
- 2002-11-25 MX MXPA04005263A patent/MXPA04005263A/es unknown
- 2002-11-25 CA CA002467435A patent/CA2467435A1/en not_active Abandoned
- 2002-11-25 JP JP2003549315A patent/JP2005517640A/ja active Pending
- 2002-11-25 DE DE60219068T patent/DE60219068T2/de not_active Expired - Fee Related
- 2002-11-25 IL IL16199202A patent/IL161992A0/xx unknown
- 2002-11-29 PE PE2002001152A patent/PE20030723A1/es not_active Application Discontinuation
- 2002-11-29 TW TW091134784A patent/TW200303861A/zh unknown
- 2002-11-29 PA PA20028559701A patent/PA8559701A1/es unknown
- 2002-12-02 AR ARP020104642A patent/AR037683A1/es unknown
- 2002-12-03 US US10/308,963 patent/US6747053B2/en not_active Expired - Fee Related
- 2002-12-03 GT GT200200253A patent/GT200200253A/es unknown
- 2002-12-03 UY UY27561A patent/UY27561A1/es not_active Application Discontinuation
-
2004
- 2004-06-02 ZA ZA200404343A patent/ZA200404343B/en unknown
- 2004-06-28 NO NO20042719A patent/NO20042719L/no not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007080882A1 (ja) * | 2006-01-11 | 2007-07-19 | Seikagaku Corporation | オキサゾロン誘導体 |
| US8785631B2 (en) | 2006-01-11 | 2014-07-22 | Seikagaku Corporation | Oxazolone derivative compounds having a 3-oxa-1-azaspiro[4.5] core |
| JP2010531344A (ja) * | 2007-06-26 | 2010-09-24 | アストラゼネカ アクチボラグ | カテプシンk阻害剤としての1−シアノシクロプロピル誘導体 |
| JP2017031199A (ja) * | 2011-07-26 | 2017-02-09 | サノフイ | 3−ヘテロアロイルアミノ−プロピオン酸誘導体及び医薬としてのそれらの使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050044660A (ko) | 2005-05-12 |
| EP1453801B1 (en) | 2007-03-21 |
| TW200303861A (en) | 2003-09-16 |
| CN1639119A (zh) | 2005-07-13 |
| RU2004120784A (ru) | 2005-08-10 |
| US20030212097A1 (en) | 2003-11-13 |
| IL161992A0 (en) | 2005-11-20 |
| ES2282497T3 (es) | 2007-10-16 |
| GT200200253A (es) | 2003-07-03 |
| US6747053B2 (en) | 2004-06-08 |
| PA8559701A1 (es) | 2003-07-28 |
| DE60219068T2 (de) | 2007-12-13 |
| AU2002352126A1 (en) | 2003-06-17 |
| HUP0402344A2 (hu) | 2005-02-28 |
| ATE357432T1 (de) | 2007-04-15 |
| MXPA04005263A (es) | 2004-10-11 |
| AR037683A1 (es) | 2004-12-01 |
| ZA200404343B (en) | 2006-07-26 |
| PL370766A1 (en) | 2005-05-30 |
| WO2003048123A1 (en) | 2003-06-12 |
| CN1315806C (zh) | 2007-05-16 |
| BR0214642A (pt) | 2004-11-03 |
| NO20042719L (no) | 2004-06-28 |
| EP1453801A1 (en) | 2004-09-08 |
| UY27561A1 (es) | 2003-06-30 |
| PE20030723A1 (es) | 2003-08-29 |
| DE60219068D1 (de) | 2007-05-03 |
| CA2467435A1 (en) | 2003-06-12 |
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