JP2013535414A5 - - Google Patents
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- Publication number
- JP2013535414A5 JP2013535414A5 JP2013517548A JP2013517548A JP2013535414A5 JP 2013535414 A5 JP2013535414 A5 JP 2013535414A5 JP 2013517548 A JP2013517548 A JP 2013517548A JP 2013517548 A JP2013517548 A JP 2013517548A JP 2013535414 A5 JP2013535414 A5 JP 2013535414A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetrazol
- chlorophenyl
- compound
- morpholine
- 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 32
- 150000003839 salts Chemical class 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims 14
- 125000004122 cyclic group Chemical group 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- AAKSTVXHRNNNGZ-UHFFFAOYSA-N 4-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]morpholine Chemical compound C1=CC(Cl)=CC=C1N1C(CN2CCOCC2)=NN=N1 AAKSTVXHRNNNGZ-UHFFFAOYSA-N 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 6
- GOZVGSRNTQFFKY-UHFFFAOYSA-N 4-[[1-[3-(trifluoromethyl)phenyl]tetrazol-5-yl]methyl]morpholine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(N2C(=NN=N2)CN2CCOCC2)=C1 GOZVGSRNTQFFKY-UHFFFAOYSA-N 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 6
- XXVLFQVLMTUGNV-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-(pyrrolidin-1-ylmethyl)tetrazole Chemical compound C1=CC(Cl)=CC=C1N1C(CN2CCCC2)=NN=N1 XXVLFQVLMTUGNV-UHFFFAOYSA-N 0.000 claims 5
- ZGQWDNSVOSVNCA-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]-2-methylpiperidine Chemical compound CC1CCCCN1CC1=NN=NN1C1=CC=C(Cl)C=C1 ZGQWDNSVOSVNCA-UHFFFAOYSA-N 0.000 claims 5
- ONLZASKPAVQAMQ-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]-4-ethylsulfonylpiperazine Chemical compound C1CN(S(=O)(=O)CC)CCN1CC1=NN=NN1C1=CC=C(Cl)C=C1 ONLZASKPAVQAMQ-UHFFFAOYSA-N 0.000 claims 5
- AGMZBXBHWYHIFZ-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=NN=NN1C1=CC=C(Cl)C=C1 AGMZBXBHWYHIFZ-UHFFFAOYSA-N 0.000 claims 5
- FEHRBCZAIUPUGI-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]-4-propylsulfonylpiperazine Chemical compound C1CN(S(=O)(=O)CCC)CCN1CC1=NN=NN1C1=CC=C(Cl)C=C1 FEHRBCZAIUPUGI-UHFFFAOYSA-N 0.000 claims 5
- VCOKNESLRBSXPG-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]azepane Chemical compound C1=CC(Cl)=CC=C1N1C(CN2CCCCCC2)=NN=N1 VCOKNESLRBSXPG-UHFFFAOYSA-N 0.000 claims 5
- ZCYUQYOJBIYMDU-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]piperazine Chemical compound C1=CC(Cl)=CC=C1N1C(CN2CCNCC2)=NN=N1 ZCYUQYOJBIYMDU-UHFFFAOYSA-N 0.000 claims 5
- OMBVIHTZXXZALD-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1N1C(CN2CCCCC2)=NN=N1 OMBVIHTZXXZALD-UHFFFAOYSA-N 0.000 claims 5
- GYHNTOWCMLSOGI-UHFFFAOYSA-N 4-[[1-[3-(trifluoromethyl)phenyl]tetrazol-5-yl]methyl]morpholine Chemical compound FC(F)(F)C1=CC=CC(N2C(=NN=N2)CN2CCOCC2)=C1 GYHNTOWCMLSOGI-UHFFFAOYSA-N 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- MSZHJMWLOVWRKS-UHFFFAOYSA-N 1-[[1-(3,4-dichlorophenyl)tetrazol-5-yl]methyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(CN2CCCCC2)=NN=N1 MSZHJMWLOVWRKS-UHFFFAOYSA-N 0.000 claims 4
- UNGDBWBPQGCVTF-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]-4-methylsulfonylpiperazine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NN=NN1C1=CC=C(Cl)C=C1 UNGDBWBPQGCVTF-UHFFFAOYSA-N 0.000 claims 4
- DXVLZRVZWXLZEZ-UHFFFAOYSA-N 4-[[1-(3,4-dichlorophenyl)tetrazol-5-yl]methyl]morpholine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(CN2CCOCC2)=NN=N1 DXVLZRVZWXLZEZ-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 4
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical group C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims 3
- DIQOUXNTSMWQSA-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.1]heptane Chemical group C1OC2CNC1C2 DIQOUXNTSMWQSA-UHFFFAOYSA-N 0.000 claims 3
- 206010065390 Inflammatory pain Diseases 0.000 claims 3
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 206010027599 migraine Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- -1 trifluoromethoxy, difluoromethoxy Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- YARHEMFUSLFKJV-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)tetrazol-5-yl]methyl]-4-methylpiperidine Chemical compound C1CC(C)CCN1CC1=NN=NN1C1=CC=C(Cl)C=C1 YARHEMFUSLFKJV-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- ONHPOXROAPYCGT-UHFFFAOYSA-N 2,3,4,6,7,8,9,9a-octahydro-1h-pyrido[1,2-a]pyrazine Chemical group C1CNCC2CCCCN21 ONHPOXROAPYCGT-UHFFFAOYSA-N 0.000 claims 1
- HHIOFHJYOIVJJK-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decan-1-one Chemical group O=C1NCCC11CCNCC1 HHIOFHJYOIVJJK-UHFFFAOYSA-N 0.000 claims 1
- KAOCOULWFIQMLH-UHFFFAOYSA-N 3,3a,4,5,6,7-hexahydro-2h-[1,2]thiazolo[2,3-a]pyrazine Chemical group C1NCCN2SCCC21 KAOCOULWFIQMLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- WVOPWZRQDAOXEB-UHFFFAOYSA-N 4-[5-[(3,4-dimethylpiperazin-1-yl)methyl]tetrazol-1-yl]benzonitrile;dihydrochloride Chemical compound Cl.Cl.C1CN(C)C(C)CN1CC1=NN=NN1C1=CC=C(C#N)C=C1 WVOPWZRQDAOXEB-UHFFFAOYSA-N 0.000 claims 1
- LBOGIHKNXFTJEK-UHFFFAOYSA-N 4-[5-[(4-methylpiperazin-1-yl)methyl]tetrazol-1-yl]benzonitrile;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1CC1=NN=NN1C1=CC=C(C#N)C=C1 LBOGIHKNXFTJEK-UHFFFAOYSA-N 0.000 claims 1
- HMCUJCQGYSFLJS-UHFFFAOYSA-N 4-[5-[(4-propan-2-ylpiperazin-1-yl)methyl]tetrazol-1-yl]benzonitrile;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1CC1=NN=NN1C1=CC=C(C#N)C=C1 HMCUJCQGYSFLJS-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 0 CCC(C)=NN(C(*N(*)*)=NC)c1c(C)c(C)c(*)c(*)c1* Chemical compound CCC(C)=NN(C(*N(*)*)=NC)c1c(C)c(C)c(*)c(*)c1* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36271210P | 2010-07-09 | 2010-07-09 | |
| US61/362,712 | 2010-07-09 | ||
| PCT/GB2011/051276 WO2012004604A1 (en) | 2010-07-09 | 2011-07-08 | Tetrazole compounds as calcium channel blockers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013535414A JP2013535414A (ja) | 2013-09-12 |
| JP2013535414A5 true JP2013535414A5 (https=) | 2014-08-14 |
| JP5815029B2 JP5815029B2 (ja) | 2015-11-17 |
Family
ID=44358712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013517548A Expired - Fee Related JP5815029B2 (ja) | 2010-07-09 | 2011-07-08 | カルシウムチャネル遮断薬としてのテトラゾール化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9115132B2 (https=) |
| EP (1) | EP2590953B1 (https=) |
| JP (1) | JP5815029B2 (https=) |
| ES (1) | ES2529233T3 (https=) |
| WO (1) | WO2012004604A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201416348A (zh) * | 2012-08-29 | 2014-05-01 | Gruenenthal Chemie | 以氟甲基取代之吡咯甲醯胺 |
| CN103570584B (zh) * | 2013-11-04 | 2015-01-07 | 上海应用技术学院 | 一种取代苯甲脒类化合物的合成方法 |
| CN103553967B (zh) * | 2013-11-04 | 2015-02-18 | 上海应用技术学院 | 一种n,n-二乙基-2,4-二氯苯甲脒化合物及其制备方法 |
| MX2016007955A (es) * | 2013-12-19 | 2016-09-09 | Gruenenthal Gmbh | Pirrol carboxamidas iii fluorometil-sustituidas. |
| JP2016540820A (ja) | 2013-12-19 | 2016-12-28 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ＣａＶ２．２カルシウムチャネルブロッカーとしてのフルオロメチル置換ピロールカルボキサミド |
| MX2016007951A (es) | 2013-12-19 | 2016-09-09 | Gruenenthal Gmbh | Pirrol carboxamidas iv fluorometil-sustituidas. |
| NL2015814B1 (en) * | 2015-11-19 | 2017-06-06 | Stichting Vu-Vumc | Pyridine-based isocyanides as novel reagents for multicomponent reactions. |
| JP6943857B2 (ja) | 2015-12-22 | 2021-10-06 | シンジェンタ パーティシペーションズ アーゲー | 有害生物防除活性ピラゾール誘導体 |
| CN109897051B (zh) * | 2019-03-31 | 2021-07-09 | 白银乐天园化学有限责任公司 | 一种3-氧杂-8-氮杂-双环[3,2,1]辛烷盐酸盐的制备方法 |
| US20260049068A1 (en) * | 2022-08-08 | 2026-02-19 | Bristol-Myers Squibb Company | Substituted Tetrazolyl Compounds Useful as T Cell Activators |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2470084A (en) | 1945-09-25 | 1949-05-17 | Bilhuber Inc E | Substituted alpha-halogen alkyl tetrazoles and process for obtaining the same |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5466823A (en) | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| US5633272A (en) | 1995-02-13 | 1997-05-27 | Talley; John J. | Substituted isoxazoles for the treatment of inflammation |
| ES2183935T3 (es) | 1995-02-13 | 2003-04-01 | Searle & Co | Isoxazoles sustituidos para el tratamiento de la inflamacion. |
| UA57002C2 (uk) | 1995-10-13 | 2003-06-16 | Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі. | Похідне (метилсульфоніл)феніл-2-(5н)-фуранону, фармацевтична композиція та спосіб лікування |
| SK285353B6 (sk) | 1996-04-12 | 2006-11-03 | G. D. Searle & Co. | Substituované benzénsulfónamidy ako proliečivá COX-2 inhibítorov, farmaceutická kompozícia a spôsobich prípravy a použitia |
| IL127441A (en) | 1996-07-18 | 2003-02-12 | Merck Frosst Canada Inc | Substituted pyridines, pharmaceutical compositions comprising them and their use in the preparation of anti-inflammatory medicaments or as selective cyclooxygenase-2 inhibitors |
| CO4960662A1 (es) | 1997-08-28 | 2000-09-25 | Novartis Ag | Ciertos acidos 5-alquil-2-arilaminofenilaceticos y sus derivados |
| ES2256817T3 (es) | 1997-09-05 | 2006-07-16 | Glaxo Group Limited | Composiciones farmaceuticas que comprenden derivados de 2,3-diaril-pirazolo(1,5-b)piridazina. |
| HUP0104204A3 (en) | 1998-11-03 | 2002-06-28 | Glaxo Group Ltd | Pyrazolopyridine derivatives as cox-2 inhibitors, process for their preparation and pharmaceutical compositions thereof |
| US6025683A (en) | 1998-12-23 | 2000-02-15 | Stryker Corporation | Motor control circuit for regulating a D.C. motor |
| US6498166B1 (en) | 1999-02-27 | 2002-12-24 | Smithkline Beecham Corporation | Pyrazolopyridines |
| GB9927844D0 (en) | 1999-11-26 | 2000-01-26 | Glaxo Group Ltd | Chemical compounds |
| GB0003224D0 (en) | 2000-02-11 | 2000-04-05 | Glaxo Group Ltd | Chemical compounds |
| GB0021494D0 (en) | 2000-09-01 | 2000-10-18 | Glaxo Group Ltd | Chemical comkpounds |
| CN1816332A (zh) * | 2003-05-30 | 2006-08-09 | 神经医药技术股份有限公司 | 3－氨基甲基－吡咯烷作为n－型钙通道阻断剂 |
| SI1651621T1 (sl) | 2003-08-08 | 2008-12-31 | Janssen Pharmaceutica Nv | 2-(kinoksalin-5-ilsulfonilamino)-benzamidne spojine kot modulatorji CCK2 |
| US20060211739A1 (en) | 2005-02-08 | 2006-09-21 | Arturo Perez-Medrano | Use of selective P2X7 receptor antagonists |
| EP1928886B1 (en) | 2005-09-09 | 2011-04-13 | GlaxoSmithKline LLC | Pyridine derivatives and their use in the treatment of psychotic disorders |
| EP1966146B1 (en) | 2005-12-20 | 2011-03-02 | Abbott Healthcare Products B.V. | 4,5-dihydro- (1h)-pyrazole derivatives as cannabinoid cb1 receptor modulators |
| WO2007118323A1 (en) * | 2006-04-17 | 2007-10-25 | Neuromed Pharmaceuticals Ltd. | Isoxazole derivatives as calcium channel blockers |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| US20110257177A1 (en) * | 2008-09-22 | 2011-10-20 | Calcimedica, Inc. | Benzylthiotetrazole inhibitors of store operated calcium release |
-
2011
- 2011-07-08 EP EP11738465.1A patent/EP2590953B1/en not_active Not-in-force
- 2011-07-08 ES ES11738465.1T patent/ES2529233T3/es active Active
- 2011-07-08 US US13/808,243 patent/US9115132B2/en not_active Expired - Fee Related
- 2011-07-08 WO PCT/GB2011/051276 patent/WO2012004604A1/en not_active Ceased
- 2011-07-08 JP JP2013517548A patent/JP5815029B2/ja not_active Expired - Fee Related
-
2015
- 2015-07-17 US US14/802,982 patent/US9750719B2/en not_active Expired - Fee Related
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