JP2005529892A5 - - Google Patents
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- Publication number
- JP2005529892A5 JP2005529892A5 JP2003587801A JP2003587801A JP2005529892A5 JP 2005529892 A5 JP2005529892 A5 JP 2005529892A5 JP 2003587801 A JP2003587801 A JP 2003587801A JP 2003587801 A JP2003587801 A JP 2003587801A JP 2005529892 A5 JP2005529892 A5 JP 2005529892A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- compound
- salt according
- carboxylic acid
- decahydro
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- CRGYAECJZOWMDL-KXNHARMFSA-N methyl (3s,4ar,6r,8ar)-6-[2-(2h-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate Chemical compound C([C@@H]1C[C@@H]2C[C@H](NC[C@@H]2CC1)C(=O)OC)CC1=NN=NN1 CRGYAECJZOWMDL-KXNHARMFSA-N 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims 1
- NHYHKMQUHRGUEH-TWMKSMIVSA-N 2-ethylbutyl (3s,4ar,6r,8ar)-6-[2-(2h-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate Chemical compound C([C@@H]1C[C@@H]2C[C@H](NC[C@@H]2CC1)C(=O)OCC(CC)CC)CC1=NN=NN1 NHYHKMQUHRGUEH-TWMKSMIVSA-N 0.000 claims 1
- RBYBFCDCAMPKMA-BARDWOONSA-N 2-methylpropyl (3s,4ar,6r,8ar)-6-[2-(2h-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate Chemical compound C([C@@H]1C[C@@H]2C[C@H](NC[C@@H]2CC1)C(=O)OCC(C)C)CC=1N=NNN=1 RBYBFCDCAMPKMA-BARDWOONSA-N 0.000 claims 1
- GCLFJDWZLNXFDT-QXSJWSMHSA-N 3-methylbutyl (3s,4ar,6r,8ar)-6-[2-(2h-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate Chemical compound C([C@@H]1C[C@@H]2C[C@H](NC[C@@H]2CC1)C(=O)OCCC(C)C)CC=1N=NNN=1 GCLFJDWZLNXFDT-QXSJWSMHSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- MGJKOPKIWPCFHS-MHTWAQMVSA-N decyl (3s,4ar,6r,8ar)-6-[2-(2h-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate Chemical compound C([C@@H]1C[C@@H]2C[C@H](NC[C@@H]2CC1)C(=O)OCCCCCCCCCC)CC1=NN=NN1 MGJKOPKIWPCFHS-MHTWAQMVSA-N 0.000 claims 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
- UKKFWEFOTFPBAC-XQHKEYJVSA-N ethyl (3s,4ar,6r,8ar)-6-[2-(2h-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate Chemical compound C([C@@H]1C[C@@H]2C[C@H](NC[C@@H]2CC1)C(=O)OCC)CC1=NN=NN1 UKKFWEFOTFPBAC-XQHKEYJVSA-N 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NSENYWQRQUNUGD-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-2-ium-3-carboxylate Chemical compound C1CCCC2CNC(C(=O)O)CC21 NSENYWQRQUNUGD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NORQAGRTOSEGDN-UHFFFAOYSA-N ethyl 1-ethyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate Chemical compound C(C)OC(=O)C1NC(C2CCCCC2C1)CC NORQAGRTOSEGDN-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37612002P | 2002-04-26 | 2002-04-26 | |
| PCT/US2003/010466 WO2003091243A1 (en) | 2002-04-26 | 2003-04-14 | Ester derivatives of a decahydroisoquinoline-3-carboxylic acid as analgestics |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010142881A Division JP2010235623A (ja) | 2002-04-26 | 2010-06-23 | 鎮痛剤としてのデカヒドロイソキノリン−３−カルボン酸のエステルプロドラッグ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005529892A JP2005529892A (ja) | 2005-10-06 |
| JP2005529892A5 true JP2005529892A5 (https=) | 2008-03-27 |
Family
ID=29270765
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003587801A Pending JP2005529892A (ja) | 2002-04-26 | 2003-04-14 | 鎮痛剤としてのデカヒドロイソキノリン−３−カルボン酸のエステルプロドラッグ |
| JP2010142881A Pending JP2010235623A (ja) | 2002-04-26 | 2010-06-23 | 鎮痛剤としてのデカヒドロイソキノリン−３−カルボン酸のエステルプロドラッグ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010142881A Pending JP2010235623A (ja) | 2002-04-26 | 2010-06-23 | 鎮痛剤としてのデカヒドロイソキノリン−３−カルボン酸のエステルプロドラッグ |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7247644B2 (https=) |
| EP (1) | EP1511741B1 (https=) |
| JP (2) | JP2005529892A (https=) |
| KR (1) | KR100757787B1 (https=) |
| CN (1) | CN100436446C (https=) |
| AU (1) | AU2003226277B2 (https=) |
| BR (1) | BR0308911A (https=) |
| CA (1) | CA2480026C (https=) |
| DK (1) | DK1511741T3 (https=) |
| EA (1) | EA009526B1 (https=) |
| ES (1) | ES2398225T3 (https=) |
| IL (1) | IL164773A (https=) |
| MX (1) | MXPA04009857A (https=) |
| NZ (1) | NZ535245A (https=) |
| PT (1) | PT1511741E (https=) |
| SI (1) | SI1511741T1 (https=) |
| WO (1) | WO2003091243A1 (https=) |
| ZA (1) | ZA200409552B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100757787B1 (ko) * | 2002-04-26 | 2007-09-11 | 일라이 릴리 앤드 캄파니 | 진통제로서의 데카히드로이소퀴놀린-3-카르복실산의 에스테르 유도체 |
| US8603980B2 (en) | 2007-01-16 | 2013-12-10 | The Johns Hopkins University | Glutamate receptor antagonists and methods of use |
| MX2022016223A (es) | 2020-07-02 | 2023-02-23 | Sea Pharmaceuticals Llc | Composiciones farmaceuticas de acido 6-(2-(2h-tetrazol-5-il)etil)- 6-fluorodecahidroisoquinolina-3-carboxilico y derivados de ester del mismo. |
| WO2022261287A1 (en) * | 2021-06-09 | 2022-12-15 | Proniras Corporation | Methods of treating nerve agent-induced seizures |
| WO2023130008A2 (en) * | 2022-01-01 | 2023-07-06 | Sea Pharmaceuticals Llc | Pharmaceutical compositions of 6-(2-(2h-tetrazol-5-yl)ethyl)decahydroisoquinoline-3-carboxylic acid and derivatives thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK406686D0 (da) * | 1986-08-26 | 1986-08-26 | Hans Bundgaard | Carboxylsyrederivater |
| US4902695A (en) * | 1989-02-13 | 1990-02-20 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| US5284957A (en) * | 1992-09-03 | 1994-02-08 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| US5356902A (en) | 1992-11-06 | 1994-10-18 | Eli Lilly And Company | Decahydroisoquinoline compounds as excitatory amino acid receptor antagonists |
| US5446051A (en) | 1994-05-31 | 1995-08-29 | Eli Lilly And Company | Aryl-spaced decahydroisoquinoline-3-carboxylic acids as excitatory amino acid receptor antagonists |
| US5767117A (en) | 1994-11-18 | 1998-06-16 | The General Hospital Corporation | Method for treating vascular headaches |
| HUP0002030A3 (en) | 1997-04-07 | 2002-01-28 | Lilly Co Eli | Use of glur5 receptorantagonists for the treatment of pain |
| EP1200073B1 (en) | 1999-07-06 | 2007-01-10 | Eli Lilly And Company | SELECTIVE iGluR 5? RECEPTOR ANTAGONISTS FOR THE TREATMENT OF MIGRAINE |
| WO2001002367A2 (en) * | 1999-07-06 | 2001-01-11 | Eli Lilly And Company | Diester prodrugs of a decahydroisoquinoline-3-carboxylic acid |
| AU2574801A (en) | 1999-12-22 | 2001-07-03 | Eli Lilly And Company | Selective iGLUR5 receptor antagonists |
| WO2002053556A2 (en) | 2001-01-05 | 2002-07-11 | Eli Lilly And Company | Pyrrolidinylmethyl substituted decahydroisoquinolines as excitatory amino acid receptor antagonists |
| WO2003024453A1 (en) | 2001-01-05 | 2003-03-27 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| AU2002227020A1 (en) | 2001-01-05 | 2002-07-16 | Eli Lilly And Company | Pyrrolidinylmethyl- and piperidinyl substituted decahydroisoquinolines as excitatory amino acid receptor antagonists |
| WO2003024934A2 (en) | 2001-01-05 | 2003-03-27 | Eli Lilly And Company | Derivatives of the (3s, 4ar, 6s, 8ar) 6-phenylamino-1, 2, 3, 4, 4a, 5, 6, 7, 8, 8a-decahydro isoquinoline-3-carboxylic acid as excitatory amino acid receptor antagonists for the treatment of neurological disorders and neurodegenerative diseases |
| WO2003082856A1 (en) | 2002-03-22 | 2003-10-09 | Eli Lilly And Company | Isoquinoline-3-carboxylic acid derivatives as excitatory amino acid receptor antagonists |
| KR100757787B1 (ko) * | 2002-04-26 | 2007-09-11 | 일라이 릴리 앤드 캄파니 | 진통제로서의 데카히드로이소퀴놀린-3-카르복실산의 에스테르 유도체 |
-
2003
- 2003-04-14 KR KR1020047017143A patent/KR100757787B1/ko not_active Expired - Fee Related
- 2003-04-14 CN CNB038094606A patent/CN100436446C/zh not_active Expired - Fee Related
- 2003-04-14 JP JP2003587801A patent/JP2005529892A/ja active Pending
- 2003-04-14 NZ NZ535245A patent/NZ535245A/en not_active IP Right Cessation
- 2003-04-14 US US10/511,452 patent/US7247644B2/en not_active Expired - Fee Related
- 2003-04-14 WO PCT/US2003/010466 patent/WO2003091243A1/en not_active Ceased
- 2003-04-14 AU AU2003226277A patent/AU2003226277B2/en not_active Ceased
- 2003-04-14 CA CA2480026A patent/CA2480026C/en not_active Expired - Fee Related
- 2003-04-14 MX MXPA04009857A patent/MXPA04009857A/es active IP Right Grant
- 2003-04-14 PT PT37472693T patent/PT1511741E/pt unknown
- 2003-04-14 EA EA200401432A patent/EA009526B1/ru not_active IP Right Cessation
- 2003-04-14 BR BR0308911-8A patent/BR0308911A/pt active Search and Examination
- 2003-04-14 SI SI200332227T patent/SI1511741T1/sl unknown
- 2003-04-14 EP EP03747269A patent/EP1511741B1/en not_active Expired - Lifetime
- 2003-04-14 DK DK03747269.3T patent/DK1511741T3/da active
- 2003-04-14 ES ES03747269T patent/ES2398225T3/es not_active Expired - Lifetime
-
2004
- 2004-10-21 IL IL164773A patent/IL164773A/en not_active IP Right Cessation
- 2004-11-25 ZA ZA200409552A patent/ZA200409552B/xx unknown
-
2010
- 2010-06-23 JP JP2010142881A patent/JP2010235623A/ja active Pending