JP2007513988A5 - - Google Patents
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- Publication number
- JP2007513988A5 JP2007513988A5 JP2006544256A JP2006544256A JP2007513988A5 JP 2007513988 A5 JP2007513988 A5 JP 2007513988A5 JP 2006544256 A JP2006544256 A JP 2006544256A JP 2006544256 A JP2006544256 A JP 2006544256A JP 2007513988 A5 JP2007513988 A5 JP 2007513988A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- hydroxypyrrolidine
- methylamino
- dicarboxamide
- chlorophenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000012453 solvate Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 5
- -1 COOA Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010022562 Intermittent claudication Diseases 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 238000002399 angioplasty Methods 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 208000021156 intermittent vascular claudication Diseases 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- NDGVILUNDMNHDW-VQIMIIECSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[2-fluoro-4-[(2-methoxyacetyl)-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound FC1=CC(N(C)C(=O)COC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 NDGVILUNDMNHDW-VQIMIIECSA-N 0.000 claims 1
- KUTNFVXZDGPTQX-WOJBJXKFSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[(2-ethoxyacetyl)-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)COCC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 KUTNFVXZDGPTQX-WOJBJXKFSA-N 0.000 claims 1
- JCKDWPIRQOWMCV-ZYTVHREMSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(2,6-dimethylmorpholin-4-yl)acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1C(C)OC(C)CN1CC(=O)N(C)C(C=C1)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 JCKDWPIRQOWMCV-ZYTVHREMSA-N 0.000 claims 1
- YSZOCNOTIDBMJE-DNQXCXABSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(cyclohexylamino)acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C(NC(=O)[C@@H]2N(C[C@H](O)C2)C(=O)NC=2C=CC(Cl)=CC=2)C=CC=1N(C)C(=O)CNC1CCCCC1 YSZOCNOTIDBMJE-DNQXCXABSA-N 0.000 claims 1
- CKFQHXGHZIFJBX-DHIUTWEWSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(cyclopentylamino)acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C(NC(=O)[C@@H]2N(C[C@H](O)C2)C(=O)NC=2C=CC(Cl)=CC=2)C=CC=1N(C)C(=O)CNC1CCCC1 CKFQHXGHZIFJBX-DHIUTWEWSA-N 0.000 claims 1
- OFWIVZSFBMSHPJ-FGZHOGPDSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(cyclopropylmethylamino)acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C(NC(=O)[C@@H]2N(C[C@H](O)C2)C(=O)NC=2C=CC(Cl)=CC=2)C=CC=1N(C)C(=O)CNCC1CC1 OFWIVZSFBMSHPJ-FGZHOGPDSA-N 0.000 claims 1
- PCJQUXTUWTZMOS-FGZHOGPDSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(diethylamino)acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)CN(CC)CC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 PCJQUXTUWTZMOS-FGZHOGPDSA-N 0.000 claims 1
- DCVPASZGDOVYRS-YLJYHZDGSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(dimethylamino)acetyl]-methylamino]-2-fluorophenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound FC1=CC(N(C)C(=O)CN(C)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 DCVPASZGDOVYRS-YLJYHZDGSA-N 0.000 claims 1
- IOSIWRNJWRRBDV-WOJBJXKFSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(dimethylamino)acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)CN(C)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 IOSIWRNJWRRBDV-WOJBJXKFSA-N 0.000 claims 1
- SBKHMNHSWHIJHE-WOJBJXKFSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-(ethylamino)acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)CNCC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 SBKHMNHSWHIJHE-WOJBJXKFSA-N 0.000 claims 1
- UOHOKUCCUMMICI-ISKUEHANSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[4-[[2-[3-(cyclohexylmethyl)piperidin-1-yl]acetyl]-methylamino]phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C(NC(=O)[C@@H]2N(C[C@H](O)C2)C(=O)NC=2C=CC(Cl)=CC=2)C=CC=1N(C)C(=O)CN(C1)CCCC1CC1CCCCC1 UOHOKUCCUMMICI-ISKUEHANSA-N 0.000 claims 1
- NUSINIZMDGHUAJ-QZTJIDSGSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[5-[[2-(dimethylamino)acetyl]-methylamino]pyridin-2-yl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound N1=CC(N(C)C(=O)CN(C)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 NUSINIZMDGHUAJ-QZTJIDSGSA-N 0.000 claims 1
- QZYAUQZZYWEXMZ-QZTJIDSGSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-[(2-hydroxyacetyl)-methylamino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C(=O)CO)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 QZYAUQZZYWEXMZ-QZTJIDSGSA-N 0.000 claims 1
- UKLUZDAWRYWYJY-RTBURBONSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-[(2-methoxyacetyl)-methylamino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)COC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 UKLUZDAWRYWYJY-RTBURBONSA-N 0.000 claims 1
- RMEZNVRENNUAAK-DHIUTWEWSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-[[2-(4-hydroxypiperidin-1-yl)acetyl]-methylamino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C(NC(=O)[C@@H]2N(C[C@H](O)C2)C(=O)NC=2C=CC(Cl)=CC=2)C=CC=1N(C)C(=O)CN1CCC(O)CC1 RMEZNVRENNUAAK-DHIUTWEWSA-N 0.000 claims 1
- GCFOVMYEESURTR-FGZHOGPDSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-[methyl-(2-morpholin-4-ylacetyl)amino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C(NC(=O)[C@@H]2N(C[C@H](O)C2)C(=O)NC=2C=CC(Cl)=CC=2)C=CC=1N(C)C(=O)CN1CCOCC1 GCFOVMYEESURTR-FGZHOGPDSA-N 0.000 claims 1
- OZNXWSRDSQCMDV-FGZHOGPDSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-[methyl-[2-(2-methylimidazol-1-yl)acetyl]amino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C(NC(=O)[C@@H]2N(C[C@H](O)C2)C(=O)NC=2C=CC(Cl)=CC=2)C=CC=1N(C)C(=O)CN1C=CN=C1C OZNXWSRDSQCMDV-FGZHOGPDSA-N 0.000 claims 1
- IHYKVAZEZVIFLC-RTBURBONSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-[methyl-[2-(methylamino)acetyl]amino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)CNC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 IHYKVAZEZVIFLC-RTBURBONSA-N 0.000 claims 1
- MEHKTVPSVCLVSX-NHCUHLMSSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-[methyl-[2-(propan-2-ylamino)acetyl]amino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)CNC(C)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 MEHKTVPSVCLVSX-NHCUHLMSSA-N 0.000 claims 1
- WMRBQGQJNWKGEC-IAGOWNOFSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[5-[(2-methoxyacetyl)-methylamino]pyridin-2-yl]pyrrolidine-1,2-dicarboxamide Chemical compound N1=CC(N(C)C(=O)COC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 WMRBQGQJNWKGEC-IAGOWNOFSA-N 0.000 claims 1
- RPGRSSXPCNKXRS-NHCUHLMSSA-N (2r,4r)-1-n-(4-ethynylphenyl)-4-hydroxy-2-n-[4-[(2-methoxyacetyl)-methylamino]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)COC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(=CC=2)C#C)C[C@H](O)C1 RPGRSSXPCNKXRS-NHCUHLMSSA-N 0.000 claims 1
- BPBSNKGJQDSFEN-FGZHOGPDSA-N (2r,4r)-2-n-[4-[(2-butoxyacetyl)-methylamino]phenyl]-1-n-(4-chlorophenyl)-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)COCCCC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 BPBSNKGJQDSFEN-FGZHOGPDSA-N 0.000 claims 1
- HESJRWAJNALPQC-QZTJIDSGSA-N (2r,4r)-2-n-[4-[(2-chloroacetyl)-methylamino]phenyl]-1-n-(4-chlorophenyl)-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C(=O)CCl)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 HESJRWAJNALPQC-QZTJIDSGSA-N 0.000 claims 1
- CVVOUXPFIQSNGP-FGZHOGPDSA-N (2r,4r)-2-n-[4-[[2-(dimethylamino)acetyl]-methylamino]phenyl]-1-n-(4-ethynylphenyl)-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C)C(=O)CN(C)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(=CC=2)C#C)C[C@H](O)C1 CVVOUXPFIQSNGP-FGZHOGPDSA-N 0.000 claims 1
- FNLBMMCNIOCYRG-NHCUHLMSSA-N (2r,4r)-2-n-[4-[[2-(tert-butylamino)acetyl]-methylamino]phenyl]-1-n-(4-chlorophenyl)-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C(=O)CNC(C)(C)C)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 FNLBMMCNIOCYRG-NHCUHLMSSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 108010054265 Factor VIIa Proteins 0.000 claims 1
- 108010074860 Factor Xa Proteins 0.000 claims 1
- FUYFVQGJIBPFPP-WOJBJXKFSA-N [2-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-n-methylanilino]-2-oxoethyl] acetate Chemical compound C1=CC(N(C(=O)COC(C)=O)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 FUYFVQGJIBPFPP-WOJBJXKFSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- LIPXKYLULLAUAS-YOQGVNIDSA-N methyl (2R)-2-[[2-[[4-[[(4R)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]phenyl]methylamino]-2-oxoethyl]amino]-4-methylpentanoate Chemical compound ClC1=CC=C(C=C1)NC(=O)N1C(C[C@H](C1)O)C(=O)NC1=CC=C(C=C1)CNC(=O)CN[C@@H](C(=O)OC)CC(C)C LIPXKYLULLAUAS-YOQGVNIDSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002980 postoperative effect Effects 0.000 claims 1
- 0 CC1(/C=*/C(/NC(C(C*(*)CC2)N2C(Nc2ccc(*)cc2)=O)=O)=*\*(*)/C=C1)N(*)C(C*)=O Chemical compound CC1(/C=*/C(/NC(C(C*(*)CC2)N2C(Nc2ccc(*)cc2)=O)=O)=*\*(*)/C=C1)N(*)C(C*)=O 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10358814.0 | 2003-12-16 | ||
| DE10358814A DE10358814A1 (de) | 2003-12-16 | 2003-12-16 | Prolinylarylacetamide |
| PCT/EP2004/013509 WO2005058817A1 (de) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007513988A JP2007513988A (ja) | 2007-05-31 |
| JP2007513988A5 true JP2007513988A5 (https=) | 2008-01-17 |
| JP4800969B2 JP4800969B2 (ja) | 2011-10-26 |
Family
ID=34683363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006544256A Expired - Fee Related JP4800969B2 (ja) | 2003-12-16 | 2004-11-26 | プロリニルアリールアセトアミド |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7732481B2 (https=) |
| EP (1) | EP1697318B1 (https=) |
| JP (1) | JP4800969B2 (https=) |
| KR (1) | KR20060113729A (https=) |
| CN (1) | CN1894210A (https=) |
| AR (1) | AR046765A1 (https=) |
| AT (1) | ATE406350T1 (https=) |
| AU (1) | AU2004299197B2 (https=) |
| BR (1) | BRPI0417630A (https=) |
| CA (1) | CA2549589A1 (https=) |
| DE (2) | DE10358814A1 (https=) |
| ES (1) | ES2310772T3 (https=) |
| MX (1) | MXPA06006740A (https=) |
| RU (1) | RU2006125509A (https=) |
| WO (1) | WO2005058817A1 (https=) |
| ZA (1) | ZA200605841B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1818330A1 (de) | 2006-02-14 | 2007-08-15 | Boehringer Ingelheim Pharma GmbH & Co.KG | Substituierte Prolinamide, deren Herstellung und deren Verwendung als Arzneimittel |
| MY146623A (en) | 2006-05-16 | 2012-09-14 | Boehringer Ingelheim Int | Substituted prolinamides, manufacturing, and the use thereof as medicaments |
| WO2009000878A1 (en) * | 2007-06-28 | 2008-12-31 | Novartis Ag | Kallikrein 7 modulators |
| WO2011027888A1 (ja) * | 2009-09-07 | 2011-03-10 | 大日本住友製薬株式会社 | ジアミド－フェニル誘導体、またはその薬学的に許容される塩 |
| CN109761957B (zh) * | 2019-01-18 | 2020-05-19 | 西安交通大学 | 一种含有羟脯氨酸的化合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7030141B2 (en) | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| BRPI0408444A (pt) * | 2003-04-03 | 2006-04-04 | Merck Patent Gmbh | derivados de 1-n-(fenil)-2-n-(fenil) pirazolidina-1,2-dicarboxamida como inibidores de fator xa de coagulação para o tratamento de trombose |
| PL377633A1 (pl) * | 2003-04-03 | 2006-02-06 | Merck Patent Gmbh | Związki karbonylowe |
| DE102004014945A1 (de) * | 2004-03-26 | 2005-10-13 | Merck Patent Gmbh | Prolinylderivate |
-
2003
- 2003-12-16 DE DE10358814A patent/DE10358814A1/de not_active Withdrawn
-
2004
- 2004-11-26 AU AU2004299197A patent/AU2004299197B2/en not_active Ceased
- 2004-11-26 RU RU2006125509/04A patent/RU2006125509A/ru not_active Application Discontinuation
- 2004-11-26 US US10/583,094 patent/US7732481B2/en not_active Expired - Fee Related
- 2004-11-26 AT AT04820404T patent/ATE406350T1/de not_active IP Right Cessation
- 2004-11-26 JP JP2006544256A patent/JP4800969B2/ja not_active Expired - Fee Related
- 2004-11-26 MX MXPA06006740A patent/MXPA06006740A/es not_active Application Discontinuation
- 2004-11-26 KR KR1020067011704A patent/KR20060113729A/ko not_active Withdrawn
- 2004-11-26 WO PCT/EP2004/013509 patent/WO2005058817A1/de not_active Ceased
- 2004-11-26 CN CNA2004800376989A patent/CN1894210A/zh active Pending
- 2004-11-26 CA CA002549589A patent/CA2549589A1/en not_active Abandoned
- 2004-11-26 BR BRPI0417630-8A patent/BRPI0417630A/pt not_active Application Discontinuation
- 2004-11-26 ES ES04820404T patent/ES2310772T3/es not_active Expired - Lifetime
- 2004-11-26 DE DE502004007959T patent/DE502004007959D1/de not_active Expired - Lifetime
- 2004-11-26 EP EP04820404A patent/EP1697318B1/de not_active Expired - Lifetime
- 2004-12-15 AR ARP040104656A patent/AR046765A1/es unknown
-
2006
- 2006-07-14 ZA ZA200605841A patent/ZA200605841B/en unknown
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