JP2004504324A5 - - Google Patents
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- Publication number
- JP2004504324A5 JP2004504324A5 JP2002512190A JP2002512190A JP2004504324A5 JP 2004504324 A5 JP2004504324 A5 JP 2004504324A5 JP 2002512190 A JP2002512190 A JP 2002512190A JP 2002512190 A JP2002512190 A JP 2002512190A JP 2004504324 A5 JP2004504324 A5 JP 2004504324A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- methyl
- nitro
- tetrahydro
- 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 30
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- -1 azepin-6-yl Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 208000027089 Parkinsonian disease Diseases 0.000 claims 4
- 206010034010 Parkinsonism Diseases 0.000 claims 4
- 208000028017 Psychotic disease Diseases 0.000 claims 4
- 230000001154 acute effect Effects 0.000 claims 4
- 230000001684 chronic effect Effects 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 3
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 206010019233 Headaches Diseases 0.000 claims 2
- 208000010496 Heart Arrest Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000007101 Muscle Cramp Diseases 0.000 claims 2
- 206010057852 Nicotine dependence Diseases 0.000 claims 2
- 208000026251 Opioid-Related disease Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- 208000005392 Spasm Diseases 0.000 claims 2
- 208000025569 Tobacco Use disease Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 206010047700 Vomiting Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 230000036770 blood supply Effects 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 230000003925 brain function Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 231100000040 eye damage Toxicity 0.000 claims 2
- 230000006870 function Effects 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- 231100000869 headache Toxicity 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 230000007954 hypoxia Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 201000005040 opiate dependence Diseases 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 230000035935 pregnancy Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000020431 spinal cord injury Diseases 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 230000008673 vomiting Effects 0.000 claims 2
- PEIPZAXTFGYYAP-UHFFFAOYSA-N 2-methyl-5-nitro-6-(4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-6-yl)-1h-pyrimidin-4-one Chemical compound O=C1NC(C)=NC(N2CCC=3SC=NC=3CC2)=C1[N+]([O-])=O PEIPZAXTFGYYAP-UHFFFAOYSA-N 0.000 claims 1
- VQJHFBNQMZLWTB-UHFFFAOYSA-N 2-methyl-5-nitro-6-(4,5,7,8-tetrahydrothieno[2,3-d]azepin-6-yl)-1h-pyrimidin-4-one Chemical compound O=C1NC(C)=NC(N2CCC=3SC=CC=3CC2)=C1[N+]([O-])=O VQJHFBNQMZLWTB-UHFFFAOYSA-N 0.000 claims 1
- PPAHTKRIGLLFBZ-UHFFFAOYSA-N 2-methyl-5-nitro-6-(5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl)-1h-pyrimidin-4-one Chemical compound CC1=NC(O)=C([N+]([O-])=O)C(N2CCC3=NC=NC=C3CC2)=N1 PPAHTKRIGLLFBZ-UHFFFAOYSA-N 0.000 claims 1
- NFISWCGEIUQLHZ-UHFFFAOYSA-N 2-methyl-6-(2-methyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-6-yl)-5-nitro-1h-pyrimidin-4-one Chemical compound C1CC=2SC(C)=NC=2CCN1C=1N=C(C)NC(=O)C=1[N+]([O-])=O NFISWCGEIUQLHZ-UHFFFAOYSA-N 0.000 claims 1
- PZMDPBXWOPDNII-UHFFFAOYSA-N 6-(2-amino-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-6-yl)-2-methyl-5-nitro-1h-pyrimidin-4-one Chemical compound O=C1NC(C)=NC(N2CCC=3SC(N)=NC=3CC2)=C1[N+]([O-])=O PZMDPBXWOPDNII-UHFFFAOYSA-N 0.000 claims 1
- XBVZDDMQMBTZFS-UHFFFAOYSA-N 6-(6-ethoxy-2-methyl-5-nitropyrimidin-4-yl)-2-methyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepine Chemical compound CCOC1=NC(C)=NC(N2CCC=3SC(C)=NC=3CC2)=C1[N+]([O-])=O XBVZDDMQMBTZFS-UHFFFAOYSA-N 0.000 claims 1
- ZIXGMFSFXIBUFN-UHFFFAOYSA-N 6-(6-ethoxy-2-methyl-5-nitropyrimidin-4-yl)-4,5,7,8-tetrahydrothieno[2,3-d]azepine Chemical compound CCOC1=NC(C)=NC(N2CCC=3SC=CC=3CC2)=C1[N+]([O-])=O ZIXGMFSFXIBUFN-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 description 8
- 0 CCCCCN(C(C(C([N+]1)Br)[N+](O)=O)O)C1=* Chemical compound CCCCCN(C(C(C([N+]1)Br)[N+](O)=O)O)C1=* 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00115450 | 2000-07-18 | ||
| PCT/EP2001/008186 WO2002006288A1 (en) | 2000-07-18 | 2001-07-16 | Tetrahydro-heterocycloazepinyl pyrimidine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004504324A JP2004504324A (ja) | 2004-02-12 |
| JP2004504324A5 true JP2004504324A5 (enExample) | 2007-07-05 |
| JP4060705B2 JP4060705B2 (ja) | 2008-03-12 |
Family
ID=8169290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002512190A Expired - Fee Related JP4060705B2 (ja) | 2000-07-18 | 2001-07-16 | テトラヒドロ−ヘテロシクロアゼピニルピリミジン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6369222B1 (enExample) |
| EP (1) | EP1303521B1 (enExample) |
| JP (1) | JP4060705B2 (enExample) |
| KR (1) | KR100525214B1 (enExample) |
| CN (1) | CN1187358C (enExample) |
| AR (1) | AR031715A1 (enExample) |
| AT (1) | ATE288437T1 (enExample) |
| AU (2) | AU1041802A (enExample) |
| BR (1) | BR0112586A (enExample) |
| CA (1) | CA2415966C (enExample) |
| DE (1) | DE60108759T2 (enExample) |
| DK (1) | DK1303521T3 (enExample) |
| ES (1) | ES2236317T3 (enExample) |
| MX (1) | MXPA03000428A (enExample) |
| PT (1) | PT1303521E (enExample) |
| WO (1) | WO2002006288A1 (enExample) |
| ZA (1) | ZA200300163B (enExample) |
Families Citing this family (32)
| 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 |
| 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 |
| US20040215284A1 (en) * | 2003-01-30 | 2004-10-28 | Recordati S.A. | Treatment of neuromuscular dysfunction of the lower urinary tract with selective mGlu5 antagonists |
| 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 |
| DE102004001873A1 (de) | 2004-01-14 | 2005-09-29 | Bayer Healthcare Ag | Cyanopyrimidinone |
| DE102004019708A1 (de) * | 2004-04-20 | 2005-11-17 | Basf Ag | Offenzellige Schaumstoffe und Verfahren zu ihrer Herstellung |
| EP1778243B1 (en) * | 2004-06-30 | 2012-10-31 | Athersys, Inc. | Substituted azepine derivatives as serotonin receptor modulators |
| CN101068815B (zh) | 2004-10-04 | 2012-09-05 | 千禧药品公司 | 有效作为蛋白激酶抑制剂的内酰胺化合物 |
| JP2009520016A (ja) * | 2005-12-20 | 2009-05-21 | リヒター ゲデオン ニュルト | 新規な化合物 |
| PE20080145A1 (es) | 2006-03-21 | 2008-02-11 | Janssen Pharmaceutica Nv | Tetrahidro-pirimidoazepinas como moduladores de trpv1 |
| CN101821256A (zh) * | 2007-08-02 | 2010-09-01 | 瑞蔻达蒂爱尔兰有限公司 | 作为mGlu5拮抗剂的新型杂环化合物 |
| PE20091211A1 (es) | 2007-11-30 | 2009-09-14 | Boehringer Ingelheim Int | Derivados de pirazolopirimidina como moduladores de pde9a |
| US8288397B2 (en) | 2007-12-17 | 2012-10-16 | Janssen Pharmaceutica Nv | Imidazolo-, oxazolo-, and thiazolopyrimidine modulators of TRPV1 |
| 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 |
| CA2736304A1 (en) | 2008-09-08 | 2010-03-11 | Boehringer Ingelheim International Gmbh | Pyrazolopyrimidines and their use for the treatment of cns disorders |
| WO2010065134A1 (en) | 2008-12-05 | 2010-06-10 | Millennium Pharmaceuticals, Inc. | 5, 7-dihydro- 6h-pyrimido [ 5, 4-d] [ 1 ] benzazepin-6-thiones as plk inhibitors |
| EP2393780A1 (en) * | 2009-02-04 | 2011-12-14 | Recordati Ireland Limited | Heterocyclic derivatives as m-glu5 antagonists |
| GEP20146098B (en) | 2009-03-31 | 2014-05-27 | Boehringer Ingelheim Int | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their usage as pde9a modulators |
| WO2011029633A1 (en) | 2009-09-14 | 2011-03-17 | Recordati Ireland Limited | Heterocyclic mglu5 antagonists |
| JP2013529673A (ja) | 2010-07-09 | 2013-07-22 | レコルダーティ アイルランド リミテッド | Ｍｇｌｕ５アンタゴニストとしての新規スピロ複素環化合物 |
| MX344770B (es) | 2010-08-12 | 2017-01-06 | Boehringer Ingelheim Int Gmbh * | Derivados de 6-cicloalquil-1,5-dihidro-pirazolo (3,4-d) pirimidin-4-onas y su uso como inhibidores de pde9a. |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US8822464B2 (en) | 2011-11-28 | 2014-09-02 | Boehringer Ingelheim International Gmbh | N-aryl-piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
| US8741892B2 (en) | 2011-12-05 | 2014-06-03 | Boehringer Ingelheim International Gmbh | Compounds |
| US8796467B2 (en) * | 2011-12-13 | 2014-08-05 | Boehringer Ingelheim International Gmbh | Compounds |
| US8846948B2 (en) | 2011-12-13 | 2014-09-30 | Boehringer Ingelheim International Gmbh | Compounds |
| US8883789B2 (en) | 2011-12-14 | 2014-11-11 | Boehringer Ingelheim International Gmbh | Piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
| US8937176B2 (en) | 2011-12-14 | 2015-01-20 | Boehringer Ingelheim International Gmbh | Compounds |
| US8716277B2 (en) | 2011-12-14 | 2014-05-06 | Boehringer Ingelheim International Gmbh | Substituted imidazole compounds useful as positive allosteric modulators of mGlu5 receptor activity |
| US8889677B2 (en) | 2012-01-17 | 2014-11-18 | Boehringer Ingellheim International GmbH | Substituted triazoles useful as mGlu5 receptor modulators |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940395A (en) * | 1969-08-29 | 1976-02-24 | American Home Products Corporation | 4-Amino-2-phenyl-6-thiopryimidines |
| BG17968A3 (bg) * | 1970-08-14 | 1974-03-05 | Dr. Karl Thomae Gmbh | Метод за получаване на производни на азепина |
| BE790287A (fr) * | 1971-10-28 | 1973-04-19 | Delalande Sa | Acides pyrimidin-6yl acethydroxamiques, leur procede de preparation et leur application en therapeutique |
| FR2608607B1 (fr) | 1986-12-23 | 1989-04-28 | Sanofi Sa | Procede de preparation de thienylethylamines et dithienylethylamines ainsi obtenues |
| DE3820775A1 (de) | 1988-06-20 | 1989-12-21 | Thomae Gmbh Dr K | Neue 4,5,7,8-tetrahydro-6h-thiazolo(5,4,-d)azepine, ihre herstellung und ihre verwendung als arzneimittel |
| CA2095213A1 (en) * | 1990-11-06 | 1992-05-07 | Jotham W. Coe | Quinazoline derivatives for enhancing antitumor activity |
-
2001
- 2001-07-11 US US09/902,916 patent/US6369222B1/en not_active Expired - Fee Related
- 2001-07-16 AU AU1041802A patent/AU1041802A/xx active Pending
- 2001-07-16 BR BR0112586-9A patent/BR0112586A/pt not_active Application Discontinuation
- 2001-07-16 PT PT01978247T patent/PT1303521E/pt unknown
- 2001-07-16 AR ARP010103373A patent/AR031715A1/es not_active Application Discontinuation
- 2001-07-16 WO PCT/EP2001/008186 patent/WO2002006288A1/en not_active Ceased
- 2001-07-16 CN CNB018128459A patent/CN1187358C/zh not_active Expired - Fee Related
- 2001-07-16 AU AU2002210418A patent/AU2002210418B2/en not_active Ceased
- 2001-07-16 EP EP01978247A patent/EP1303521B1/en not_active Expired - Lifetime
- 2001-07-16 JP JP2002512190A patent/JP4060705B2/ja not_active Expired - Fee Related
- 2001-07-16 CA CA002415966A patent/CA2415966C/en not_active Expired - Fee Related
- 2001-07-16 DE DE60108759T patent/DE60108759T2/de not_active Expired - Lifetime
- 2001-07-16 ES ES01978247T patent/ES2236317T3/es not_active Expired - Lifetime
- 2001-07-16 AT AT01978247T patent/ATE288437T1/de not_active IP Right Cessation
- 2001-07-16 KR KR10-2003-7000783A patent/KR100525214B1/ko not_active Expired - Fee Related
- 2001-07-16 DK DK01978247T patent/DK1303521T3/da active
- 2001-07-16 MX MXPA03000428A patent/MXPA03000428A/es active IP Right Grant
-
2003
- 2003-01-07 ZA ZA200300163A patent/ZA200300163B/en unknown
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