JP2004536814A5 - - Google Patents
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- Publication number
- JP2004536814A5 JP2004536814A5 JP2003501988A JP2003501988A JP2004536814A5 JP 2004536814 A5 JP2004536814 A5 JP 2004536814A5 JP 2003501988 A JP2003501988 A JP 2003501988A JP 2003501988 A JP2003501988 A JP 2003501988A JP 2004536814 A5 JP2004536814 A5 JP 2004536814A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- phenyl
- alkyl
- carbonitrile
- 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 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 21
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- -1 p -pyridyl Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- XQJJVSKZRKYETA-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-(4-phenylpiperidin-1-yl)-6-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound OCCNC1=NC(OCC(F)(F)F)=C(C#N)C(N2CCC(CC2)C=2C=CC=CC=2)=N1 XQJJVSKZRKYETA-UHFFFAOYSA-N 0.000 claims 1
- SZDRMFIBAQVXRC-UHFFFAOYSA-N 2-(cyclopropylamino)-4-(2-hydroxyethylamino)-6-(4-phenylpiperazin-1-yl)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCN(CC2)C=2C=CC=CC=2)=C(C#N)C(NCCO)=NC=1NC1CC1 SZDRMFIBAQVXRC-UHFFFAOYSA-N 0.000 claims 1
- ATHYGWDFZLNGSU-UHFFFAOYSA-N 2-(cyclopropylamino)-4-(2-hydroxyethylamino)-6-(4-phenylpiperidin-1-yl)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCC(CC2)C=2C=CC=CC=2)=C(C#N)C(NCCO)=NC=1NC1CC1 ATHYGWDFZLNGSU-UHFFFAOYSA-N 0.000 claims 1
- XPCJOWNVLUTJEY-UHFFFAOYSA-N 2-(cyclopropylamino)-4-[4-(4-fluorophenyl)piperazin-1-yl]-6-(2-hydroxyethylamino)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCN(CC2)C=2C=CC(F)=CC=2)=C(C#N)C(NCCO)=NC=1NC1CC1 XPCJOWNVLUTJEY-UHFFFAOYSA-N 0.000 claims 1
- GUIBPEGBMRNZEX-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-4-(2-hydroxyethylamino)-6-(4-phenylpiperazin-1-yl)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCN(CC2)C=2C=CC=CC=2)=C(C#N)C(NCCO)=NC=1NCC1CC1 GUIBPEGBMRNZEX-UHFFFAOYSA-N 0.000 claims 1
- ZZTVMDZWZADEJR-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-4-(2-hydroxyethylamino)-6-(4-phenylpiperidin-1-yl)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCC(CC2)C=2C=CC=CC=2)=C(C#N)C(NCCO)=NC=1NCC1CC1 ZZTVMDZWZADEJR-UHFFFAOYSA-N 0.000 claims 1
- MLLHCQYZLJRAMG-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-4-[4-(4-fluorophenyl)piperazin-1-yl]-6-(2-hydroxyethylamino)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCN(CC2)C=2C=CC(F)=CC=2)=C(C#N)C(NCCO)=NC=1NCC1CC1 MLLHCQYZLJRAMG-UHFFFAOYSA-N 0.000 claims 1
- UFNWEBRZVIBAKV-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-4-[4-(4-fluorophenyl)piperidin-1-yl]-6-(2-hydroxyethylamino)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCC(CC2)C=2C=CC(F)=CC=2)=C(C#N)C(NCCO)=NC=1NCC1CC1 UFNWEBRZVIBAKV-UHFFFAOYSA-N 0.000 claims 1
- YSRVJHFURSGIDG-UHFFFAOYSA-N 2-[6-[4-(4-fluorophenyl)piperazin-1-yl]-2-methyl-5-nitropyrimidin-4-yl]oxyethanol Chemical compound CC1=NC(OCCO)=C([N+]([O-])=O)C(N2CCN(CC2)C=2C=CC(F)=CC=2)=N1 YSRVJHFURSGIDG-UHFFFAOYSA-N 0.000 claims 1
- BYWNGKMBKPMAMZ-UHFFFAOYSA-N 2-methyl-5-nitro-6-(4-phenylpiperidin-1-yl)-3-(2,2,2-trifluoroethyl)pyrimidin-4-one Chemical compound O=C1N(CC(F)(F)F)C(C)=NC(N2CCC(CC2)C=2C=CC=CC=2)=C1[N+]([O-])=O BYWNGKMBKPMAMZ-UHFFFAOYSA-N 0.000 claims 1
- WETWIACDXYEMAE-UHFFFAOYSA-N 3-(2-hydroxyethylamino)-5-(4-phenyl-3,6-dihydro-2h-pyridin-1-yl)-1,2,4-triazine-6-carbonitrile Chemical group OCCNC1=NN=C(C#N)C(N2CC=C(CC2)C=2C=CC=CC=2)=N1 WETWIACDXYEMAE-UHFFFAOYSA-N 0.000 claims 1
- CAVHNPFNSQJIBO-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)piperazin-1-yl]-5-methyl-6-phenylpyrazine-2-carbonitrile Chemical compound N#CC=1N=C(C=2C=CC=CC=2)C(C)=NC=1N(CC1)CCN1C1=CC=C(F)C=C1 CAVHNPFNSQJIBO-UHFFFAOYSA-N 0.000 claims 1
- MUJXTUPZYNZRIG-UHFFFAOYSA-N 4-(2-hydroxyethylamino)-6-(4-phenylpiperidin-1-yl)-2-(pyridin-3-ylmethylamino)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCC(CC2)C=2C=CC=CC=2)=C(C#N)C(NCCO)=NC=1NCC1=CC=CN=C1 MUJXTUPZYNZRIG-UHFFFAOYSA-N 0.000 claims 1
- KAYMQNZOONGXTI-UHFFFAOYSA-N 4-(4-phenylpiperidin-1-yl)-2-(pyridin-3-ylmethylamino)-6-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCC(CC2)C=2C=CC=CC=2)=C(C#N)C(OCC(F)(F)F)=NC=1NCC1=CC=CN=C1 KAYMQNZOONGXTI-UHFFFAOYSA-N 0.000 claims 1
- DBVWLINRVSEHBF-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)piperidin-1-yl]-2-(2-hydroxyethylamino)-6-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound OCCNC1=NC(OCC(F)(F)F)=C(C#N)C(N2CCC(CC2)C=2C=CC(F)=CC=2)=N1 DBVWLINRVSEHBF-UHFFFAOYSA-N 0.000 claims 1
- JZYSFRCVPMRUKL-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)piperidin-1-yl]-2-(pyridin-3-ylmethylamino)-6-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1CCN(C=2C(=C(OCC(F)(F)F)N=C(NCC=3C=NC=CC=3)N=2)C#N)CC1 JZYSFRCVPMRUKL-UHFFFAOYSA-N 0.000 claims 1
- SWWDHOHMVFMUDK-UHFFFAOYSA-N 4-chloro-2-(2-hydroxyethylamino)-6-(4-phenylpiperidin-1-yl)pyrimidine-5-carbonitrile Chemical compound OCCNC1=NC(Cl)=C(C#N)C(N2CCC(CC2)C=2C=CC=CC=2)=N1 SWWDHOHMVFMUDK-UHFFFAOYSA-N 0.000 claims 1
- DUTMZYIWHLQZTH-UHFFFAOYSA-N 5-ethyl-6-methyl-3-(4-phenyl-3,6-dihydro-2h-pyridin-1-yl)pyrazine-2-carbonitrile Chemical compound N1=C(C)C(CC)=NC(N2CC=C(CC2)C=2C=CC=CC=2)=C1C#N DUTMZYIWHLQZTH-UHFFFAOYSA-N 0.000 claims 1
- RYGSYSQTYIDSSG-UHFFFAOYSA-N 5-ethyl-6-methyl-3-(4-phenylpiperidin-1-yl)pyrazine-2-carbonitrile Chemical compound N1=C(C)C(CC)=NC(N2CCC(CC2)C=2C=CC=CC=2)=C1C#N RYGSYSQTYIDSSG-UHFFFAOYSA-N 0.000 claims 1
- DWDNQKHCVOKXBO-UHFFFAOYSA-N 6-[4-(4-fluorophenyl)piperazin-1-yl]-2-methyl-5-nitro-3-(2,2,2-trifluoroethyl)pyrimidin-4-one Chemical compound O=C1N(CC(F)(F)F)C(C)=NC(N2CCN(CC2)C=2C=CC(F)=CC=2)=C1[N+]([O-])=O DWDNQKHCVOKXBO-UHFFFAOYSA-N 0.000 claims 1
- WWMAVCQJXALCEP-UHFFFAOYSA-N 6-[4-(4-fluorophenyl)piperazin-1-yl]-3-(2-hydroxyethyl)-2-methyl-5-nitropyrimidin-4-one Chemical compound O=C1N(CCO)C(C)=NC(N2CCN(CC2)C=2C=CC(F)=CC=2)=C1[N+]([O-])=O WWMAVCQJXALCEP-UHFFFAOYSA-N 0.000 claims 1
- PAIAITMMROUGMU-UHFFFAOYSA-N 6-[4-(4-fluorophenyl)piperidin-1-yl]-2-methyl-5-nitro-3-(2,2,2-trifluoroethyl)pyrimidin-4-one Chemical compound O=C1N(CC(F)(F)F)C(C)=NC(N2CCC(CC2)C=2C=CC(F)=CC=2)=C1[N+]([O-])=O PAIAITMMROUGMU-UHFFFAOYSA-N 0.000 claims 1
- DJPFNIBTNYHCHV-UHFFFAOYSA-N 6-[4-(4-fluorophenyl)piperidin-1-yl]-3-(2-methoxyethyl)-2-methyl-5-nitropyrimidin-4-one Chemical compound O=C1N(CCOC)C(C)=NC(N2CCC(CC2)C=2C=CC(F)=CC=2)=C1[N+]([O-])=O DJPFNIBTNYHCHV-UHFFFAOYSA-N 0.000 claims 1
- NUUCWXKVRPMGDL-UHFFFAOYSA-N 6-ethyl-5-methyl-3-(4-phenyl-3,6-dihydro-2h-pyridin-1-yl)pyrazine-2-carbonitrile Chemical compound N1=C(C)C(CC)=NC(C#N)=C1N1CC=C(C=2C=CC=CC=2)CC1 NUUCWXKVRPMGDL-UHFFFAOYSA-N 0.000 claims 1
- XGWHHFSNYXBNAY-UHFFFAOYSA-N 6-ethyl-5-methyl-3-(4-phenylpiperazin-1-yl)pyrazine-2-carbonitrile Chemical compound N1=C(C)C(CC)=NC(C#N)=C1N1CCN(C=2C=CC=CC=2)CC1 XGWHHFSNYXBNAY-UHFFFAOYSA-N 0.000 claims 1
- ARTMWBNETUDYDF-UHFFFAOYSA-N 6-ethyl-5-methyl-3-(4-phenylpiperidin-1-yl)pyrazine-2-carbonitrile Chemical compound N1=C(C)C(CC)=NC(C#N)=C1N1CCC(C=2C=CC=CC=2)CC1 ARTMWBNETUDYDF-UHFFFAOYSA-N 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01113379 | 2001-06-01 | ||
| PCT/EP2002/005788 WO2002098864A1 (en) | 2001-06-01 | 2002-05-27 | Pyrimidine, triazine and pyrazine derivatives as glutamate receptors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004536814A JP2004536814A (ja) | 2004-12-09 |
| JP2004536814A5 true JP2004536814A5 (enExample) | 2005-09-15 |
| JP4049742B2 JP4049742B2 (ja) | 2008-02-20 |
Family
ID=8177617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003501988A Expired - Fee Related JP4049742B2 (ja) | 2001-06-01 | 2002-05-27 | グルタミン酸受容体としてのピリミジン、トリアジン及びピラジン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6673795B2 (enExample) |
| EP (1) | EP1397351B1 (enExample) |
| JP (1) | JP4049742B2 (enExample) |
| KR (1) | KR100602927B1 (enExample) |
| CN (1) | CN1245391C (enExample) |
| AR (1) | AR036075A1 (enExample) |
| AT (1) | ATE448210T1 (enExample) |
| AU (1) | AU2002319183B2 (enExample) |
| BR (1) | BR0210102A (enExample) |
| CA (1) | CA2448602C (enExample) |
| DE (1) | DE60234338D1 (enExample) |
| DK (1) | DK1397351T3 (enExample) |
| ES (1) | ES2332505T3 (enExample) |
| MX (1) | MXPA03010822A (enExample) |
| PT (1) | PT1397351E (enExample) |
| WO (1) | WO2002098864A1 (enExample) |
| ZA (1) | ZA200308859B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| KR101078098B1 (ko) * | 2003-01-14 | 2011-10-28 | 아레나 파마슈티칼스, 인크. | 대사 조절제로서의 １,２,３-삼치환된 아릴 및 헤테로아릴유도체, 및 당뇨병 및 고혈당증을 비롯한 이에 관련된장애의 예방 및 치료 |
| CN1835943B (zh) * | 2003-01-14 | 2012-03-07 | 阿伦纳药品公司 | 作为代谢调节剂的1，2，3-三取代的芳基和杂芳基衍生物及其应用 |
| EP1927594A1 (en) * | 2003-01-14 | 2008-06-04 | Arena Pharmaceuticals, Inc. | 1,2,3-Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| US7507836B2 (en) | 2003-03-26 | 2009-03-24 | Merck & Co. Inc. | Benzamide modulators of metabotropic glutamate receptors |
| DE10320785A1 (de) | 2003-05-09 | 2004-11-25 | Bayer Healthcare Ag | 6-Arylmethyl-substituierte Pyrazolopyrimidine |
| DE10328479A1 (de) | 2003-06-25 | 2005-01-13 | Bayer Ag | 6-Arylamino-5-cyano-4-pyrimidinone |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| AR045697A1 (es) | 2003-07-14 | 2005-11-09 | Arena Pharm Inc | Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo |
| AU2004257289A1 (en) * | 2003-07-16 | 2005-01-27 | Neurogen Corporation | Biaryl piperazinyl-pyridine analogues |
| PE20050483A1 (es) | 2003-10-31 | 2005-08-25 | Arena Pharm Inc | Derivados de tetrazol de formula (i), sus composiciones farmaceuticas y procesos para producir composiciones farmaceuticas |
| GB0325956D0 (en) * | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| SE0303492D0 (sv) * | 2003-12-19 | 2003-12-19 | Astrazeneca Ab | New use VII |
| DE102004001873A1 (de) * | 2004-01-14 | 2005-09-29 | Bayer Healthcare Ag | Cyanopyrimidinone |
| MY145822A (en) * | 2004-08-13 | 2012-04-30 | Neurogen Corp | Substituted biaryl piperazinyl-pyridine analogues |
| JP4958787B2 (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 | ヒトステアロイル−ＣｏＡデサチュラーゼを阻害するためのピリジン誘導体 |
| WO2007081630A2 (en) * | 2005-12-21 | 2007-07-19 | Janssen Pharmaceutica, N.V. | Substituted pyrimidinyl kinase inhibitors |
| US8153791B2 (en) | 2005-12-21 | 2012-04-10 | Janssen Pharmaceutica N.V. | Substituted pyrimidinyl oxime kinase inhibitors |
| US8278446B2 (en) * | 2005-12-21 | 2012-10-02 | Janssen Pharmaceutica N.V. | Process for preparing substituted diaminopyrimidine oximes |
| US7834178B2 (en) * | 2006-03-01 | 2010-11-16 | Bristol-Myers Squibb Company | Triazine 11-beta hydroxysteroid dehydrogenase type 1 inhibitors |
| WO2007109783A2 (en) * | 2006-03-23 | 2007-09-27 | Janssen Pharmaceutica, N.V. | Substituted pyrimidine kinase inhibitors |
| EP2217602B1 (en) | 2007-11-30 | 2018-08-29 | Boehringer Ingelheim International GmbH | 1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one derivatives and their use as pde9a modulators for the treatment of cns disorders |
| CN102046609B (zh) * | 2008-03-31 | 2014-05-14 | 全药工业株式会社 | 具有细胞保护效果的嘧啶衍生物及其应用 |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| PE20110383A1 (es) | 2008-09-08 | 2011-07-15 | Boehringer Ingelheim Int | Pirazolopirimidinonas como inhibidores de la fosfodiesterasa 9a (pde9a) |
| CA2757231A1 (en) | 2009-03-31 | 2010-10-07 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| CA2807687C (en) | 2010-08-12 | 2019-01-08 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-1, 5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors |
| SG188548A1 (en) | 2010-09-22 | 2013-04-30 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| GEAP201814266A (en) * | 2014-02-14 | 2018-05-10 | Takeda Pharmaceuticals Co | Pyrazines modulators of gpr6 |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| HUE060476T2 (hu) | 2015-06-22 | 2023-03-28 | Arena Pharm Inc | (R)-2-(7-(4-ciklopentil-3-(trifluormetil)benziloxi)-1,2,3,4- tetrahidrociklopenta[B]indol-3-il)ecetsav kristályos L-arginin-sója S1P1 receptorral kapcsolatos rendellenességek esetén való alkalmazásra |
| CN105153042B (zh) * | 2015-07-17 | 2017-11-24 | 四川大学 | 一种化合物及其在制备治疗可卡因成瘾的药物中的用途 |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| US11426397B2 (en) | 2017-03-26 | 2022-08-30 | Takeda Pharmaceutical Company Limited | Piperidinyl- and piperazinyl-substituted heteroaromatic carboxamides as modulators of GPR6 |
| US12156866B2 (en) | 2018-06-06 | 2024-12-03 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1074549B1 (en) * | 1999-08-06 | 2003-11-19 | F. Hoffmann-La Roche Ag | Tetrahydro-benzo(d)azepines and their use as antagonists at metabotropic glutamate receptors |
-
2002
- 2002-05-27 DK DK02748720.6T patent/DK1397351T3/da active
- 2002-05-27 ES ES02748720T patent/ES2332505T3/es not_active Expired - Lifetime
- 2002-05-27 PT PT02748720T patent/PT1397351E/pt unknown
- 2002-05-27 CN CNB028109872A patent/CN1245391C/zh not_active Expired - Fee Related
- 2002-05-27 CA CA002448602A patent/CA2448602C/en not_active Expired - Fee Related
- 2002-05-27 BR BR0210102-5A patent/BR0210102A/pt not_active Application Discontinuation
- 2002-05-27 WO PCT/EP2002/005788 patent/WO2002098864A1/en not_active Ceased
- 2002-05-27 JP JP2003501988A patent/JP4049742B2/ja not_active Expired - Fee Related
- 2002-05-27 DE DE60234338T patent/DE60234338D1/de not_active Expired - Lifetime
- 2002-05-27 MX MXPA03010822A patent/MXPA03010822A/es active IP Right Grant
- 2002-05-27 AU AU2002319183A patent/AU2002319183B2/en not_active Ceased
- 2002-05-27 AT AT02748720T patent/ATE448210T1/de not_active IP Right Cessation
- 2002-05-27 EP EP02748720A patent/EP1397351B1/en not_active Expired - Lifetime
- 2002-05-27 KR KR1020037015685A patent/KR100602927B1/ko not_active Expired - Fee Related
- 2002-05-29 US US10/157,338 patent/US6673795B2/en not_active Expired - Fee Related
- 2002-05-31 AR ARP020102040A patent/AR036075A1/es unknown
-
2003
- 2003-11-13 ZA ZA200308859A patent/ZA200308859B/en unknown
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