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 (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| SI1599468T1 (sl) * | 2003-01-14 | 2008-02-29 | Arena Pharm Inc | 1,2,3-trisubstituirani arilni in heteroarilni derivati kot modulatorji metabolizma ter profilaksa in zdravljenje motenj v zvezi z njim, kot diabetesain hiperglikemije |
| UA92450C2 (ru) * | 2003-01-14 | 2010-11-10 | Арена Фармасьютикалз, Инк. | 1,2,3-тризамещенные арильные и гетероарильные производные как модуляторы метаболизма, профилактика и лечение расстройств, связанных с ним, таких как диабет и гипергликемия |
| RS20050532A (sr) * | 2003-01-14 | 2007-12-31 | Arena Pharmaceuticals Inc., | Derivati 1,2,3-trisupstituisanog arila i heteroarila kao modulatori metabolizma za profilaksu i tretman poremećaja povezanih sa njim, kao što su dijebetes i hiperglikemija |
| AU2004226450A1 (en) | 2003-03-26 | 2004-10-14 | 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 |
| KR20060056944A (ko) | 2003-07-14 | 2006-05-25 | 아레나 파마슈티칼스, 인크. | 대사 조절제로서 융합된 아릴 및 헤테로아릴 유도체 및이에 관련된 장애의 예방 또는 치료 |
| CA2531619A1 (en) * | 2003-07-16 | 2005-01-27 | Neurogen Corporation | Biaryl piperazinyl-pyridine analogues |
| TWI258478B (en) | 2003-10-31 | 2006-07-21 | Arena Pharm Inc | Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof |
| 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 |
| US8278446B2 (en) * | 2005-12-21 | 2012-10-02 | Janssen Pharmaceutica N.V. | Process for preparing substituted diaminopyrimidine oximes |
| 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 |
| 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 |
| US8648085B2 (en) | 2007-11-30 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-D) pyrimidin-4-one derivatives and their use as PDE9A mudulators for the treatment of CNS disorders |
| CA2720049A1 (en) * | 2008-03-31 | 2009-10-08 | Zenyaku Kogyo Kabushikikaisha | Pyrimidine derivative having cell protecting effect and uses thereof |
| 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 |
| CN102143965A (zh) | 2008-09-08 | 2011-08-03 | 贝林格尔.英格海姆国际有限公司 | 吡唑并嘧啶酮及其在治疗中枢神经系统疾病中的用途 |
| UY32531A (es) | 2009-03-31 | 2010-10-29 | Boehringer Ingelheim Int | Nuevos compuestos para el tratamiento de trastornos del snc |
| BR112013003097B1 (pt) | 2010-08-12 | 2021-03-16 | Boehringer Ingelheim International Gmbh | 6-cicloalquil-pirazolopirimidinonas e composição farmacêutica |
| CN103221410B (zh) | 2010-09-22 | 2017-09-15 | 艾尼纳制药公司 | Gpr119受体调节剂和对与其相关的障碍的治疗 |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| UA117779C2 (uk) | 2014-02-14 | 2018-09-25 | Такеда Фармасьютікал Компані Лімітед | Піразини як модулятори gpr6 |
| CA3002540C (en) | 2015-01-06 | 2023-11-07 | Arena Pharmaceuticals, Inc. | Use of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid for treating conditions related to the s1p1 receptor |
| JP6838744B2 (ja) | 2015-06-22 | 2021-03-03 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１Ｐ１レセプター関連障害における使用のための（Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸（化合物１）の結晶性Ｌ−アルギニン塩 |
| 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 |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| CN110520127B (zh) * | 2017-03-26 | 2023-05-16 | 武田药品工业株式会社 | 作为gpr6的调节剂的经哌啶基取代的杂芳族羧酰胺和经哌嗪基取代的杂芳族羧酰胺 |
| JP7397011B2 (ja) | 2018-06-06 | 2023-12-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１ｐ１受容体に関連する状態を治療する方法 |
| WO2026032256A1 (zh) * | 2024-08-06 | 2026-02-12 | 上海齐鲁制药研究中心有限公司 | 单环类gpr6反向激动剂及其用途 |
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 BR BR0210102-5A patent/BR0210102A/pt not_active Application Discontinuation
- 2002-05-27 AT AT02748720T patent/ATE448210T1/de not_active IP Right Cessation
- 2002-05-27 ES ES02748720T patent/ES2332505T3/es not_active Expired - Lifetime
- 2002-05-27 MX MXPA03010822A patent/MXPA03010822A/es active IP Right Grant
- 2002-05-27 DE DE60234338T patent/DE60234338D1/de not_active Expired - Lifetime
- 2002-05-27 CA CA002448602A patent/CA2448602C/en not_active Expired - Fee Related
- 2002-05-27 WO PCT/EP2002/005788 patent/WO2002098864A1/en not_active Ceased
- 2002-05-27 KR KR1020037015685A patent/KR100602927B1/ko not_active Expired - Fee Related
- 2002-05-27 DK DK02748720.6T patent/DK1397351T3/da active
- 2002-05-27 EP EP02748720A patent/EP1397351B1/en not_active Expired - Lifetime
- 2002-05-27 CN CNB028109872A patent/CN1245391C/zh not_active Expired - Fee Related
- 2002-05-27 PT PT02748720T patent/PT1397351E/pt unknown
- 2002-05-27 AU AU2002319183A patent/AU2002319183B2/en not_active Ceased
- 2002-05-27 JP JP2003501988A patent/JP4049742B2/ja 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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