JP2016506963A5 - - Google Patents
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- Publication number
- JP2016506963A5 JP2016506963A5 JP2015556109A JP2015556109A JP2016506963A5 JP 2016506963 A5 JP2016506963 A5 JP 2016506963A5 JP 2015556109 A JP2015556109 A JP 2015556109A JP 2015556109 A JP2015556109 A JP 2015556109A JP 2016506963 A5 JP2016506963 A5 JP 2016506963A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydropyridin
- oxo
- benzamide
- trifluoromethyl
- fluoro
- 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
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- -1 t- butyl Chemical group 0.000 claims description 404
- 229910052736 halogen Inorganic materials 0.000 claims description 89
- 150000002367 halogens Chemical class 0.000 claims description 89
- 150000001875 compounds Chemical class 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 44
- 208000002193 Pain Diseases 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 27
- 125000002723 alicyclic group Chemical group 0.000 claims description 17
- 208000004296 neuralgia Diseases 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 208000021722 neuropathic pain Diseases 0.000 claims description 7
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 6
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- 239000003814 drug Substances 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- YXHMFJXQQXHKRO-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 YXHMFJXQQXHKRO-UHFFFAOYSA-N 0.000 claims description 5
- 206010065390 Inflammatory pain Diseases 0.000 claims description 5
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- PRBIFBCFSMEHTE-UHFFFAOYSA-N 5-fluoro-n-(2-oxo-1h-pyridin-4-yl)-2-phenoxybenzamide Chemical compound C1=CNC(=O)C=C1NC(=O)C1=CC(F)=CC=C1OC1=CC=CC=C1 PRBIFBCFSMEHTE-UHFFFAOYSA-N 0.000 claims description 4
- 208000005890 Neuroma Diseases 0.000 claims description 4
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- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- IBHSESFTJVMJEA-UHFFFAOYSA-N 4-cyano-2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(C#N)=CC=C1C(=O)NC1=CC(=O)NC=C1 IBHSESFTJVMJEA-UHFFFAOYSA-N 0.000 claims description 3
- 206010034620 Peripheral sensory neuropathy Diseases 0.000 claims description 3
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
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- 201000005572 sensory peripheral neuropathy Diseases 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
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- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 32
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims 10
- XNAAGHKLQDFJAV-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 XNAAGHKLQDFJAV-UHFFFAOYSA-N 0.000 claims 4
- CSKLRKQUNQCFCW-UHFFFAOYSA-N 4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC(=O)NC=C1 CSKLRKQUNQCFCW-UHFFFAOYSA-N 0.000 claims 4
- FZRXMWNNMIDCAX-UHFFFAOYSA-N 4-chloro-2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(Cl)=CC=C1C(=O)NC1=CC(=O)NC=C1 FZRXMWNNMIDCAX-UHFFFAOYSA-N 0.000 claims 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 4
- 208000004550 Postoperative Pain Diseases 0.000 claims 3
- JLOCNBNTRGBNSU-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound FC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 JLOCNBNTRGBNSU-UHFFFAOYSA-N 0.000 claims 2
- GIJKDQHCVRCMIN-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 GIJKDQHCVRCMIN-UHFFFAOYSA-N 0.000 claims 2
- JKAMBBDGLZFTHQ-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 JKAMBBDGLZFTHQ-UHFFFAOYSA-N 0.000 claims 2
- UXNUHKSSUVUOKZ-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 UXNUHKSSUVUOKZ-UHFFFAOYSA-N 0.000 claims 2
- WGJBFMMLUYGFBM-UHFFFAOYSA-N 2-[(5-fluoro-2-hydroxyphenyl)methoxy]-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound OC1=CC=C(F)C=C1COC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 WGJBFMMLUYGFBM-UHFFFAOYSA-N 0.000 claims 2
- HAHBFCDZJMZPDT-UHFFFAOYSA-N 2-[4-fluoro-2-(hydroxymethyl)phenoxy]-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound OCC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 HAHBFCDZJMZPDT-UHFFFAOYSA-N 0.000 claims 2
- WLRVZQGFKCYIOQ-UHFFFAOYSA-N 4-chloro-2-(2-chloro-4-fluorophenoxy)-5-fluoro-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound ClC1=CC(F)=CC=C1OC1=CC(Cl)=C(F)C=C1C(=O)NC1=CC(=O)NC=C1 WLRVZQGFKCYIOQ-UHFFFAOYSA-N 0.000 claims 2
- UUAIQHMLXPMLDV-UHFFFAOYSA-N 4-chloro-2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=CC=C1C(=O)NC1=CC(=O)NC=C1 UUAIQHMLXPMLDV-UHFFFAOYSA-N 0.000 claims 2
- CKTPSKKTZVSXLI-UHFFFAOYSA-N 4-tert-butyl-n-(2-oxo-1h-pyridin-4-yl)-2-[6-(trifluoromethyl)pyridin-3-yl]oxybenzamide Chemical compound C=1C=C(C(F)(F)F)N=CC=1OC1=CC(C(C)(C)C)=CC=C1C(=O)NC=1C=CNC(=O)C=1 CKTPSKKTZVSXLI-UHFFFAOYSA-N 0.000 claims 2
- IDCLDFZOZFUTLI-UHFFFAOYSA-N 5-chloro-2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC=C(Cl)C=C1C(=O)NC1=CC(=O)NC=C1 IDCLDFZOZFUTLI-UHFFFAOYSA-N 0.000 claims 2
- KYRYYQRTAJIXDA-UHFFFAOYSA-N 5-fluoro-n-(2-oxo-1h-pyridin-4-yl)-2-[4-(trifluoromethoxy)phenoxy]benzamide Chemical compound C1=CNC(=O)C=C1NC(=O)C1=CC(F)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 KYRYYQRTAJIXDA-UHFFFAOYSA-N 0.000 claims 2
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- INIMUMMAVCNJFA-UHFFFAOYSA-N n-(2-oxo-1h-pyridin-4-yl)-2-[4-(trifluoromethoxy)phenoxy]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 INIMUMMAVCNJFA-UHFFFAOYSA-N 0.000 claims 2
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- 206010037660 Pyrexia Diseases 0.000 description 1
- 102100031374 Sodium channel protein type 10 subunit alpha Human genes 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 210000003461 brachial plexus Anatomy 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361759059P | 2013-01-31 | 2013-01-31 | |
| US61/759,059 | 2013-01-31 | ||
| PCT/US2014/013652 WO2014120808A1 (en) | 2013-01-31 | 2014-01-29 | Pyridone amides as modulators of sodium channels |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018027902A Division JP6741704B2 (ja) | 2013-01-31 | 2018-02-20 | ナトリウムチャネルの調節剤としてのピリドンアミド |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016506963A JP2016506963A (ja) | 2016-03-07 |
| JP2016506963A5 true JP2016506963A5 (enExample) | 2017-03-09 |
| JP6389194B2 JP6389194B2 (ja) | 2018-09-12 |
Family
ID=50073531
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015556109A Active JP6389194B2 (ja) | 2013-01-31 | 2014-01-29 | ナトリウムチャネルの調節剤としてのピリドンアミド |
| JP2018027902A Active JP6741704B2 (ja) | 2013-01-31 | 2018-02-20 | ナトリウムチャネルの調節剤としてのピリドンアミド |
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| RS56015B1 (sr) | 2013-01-31 | 2017-09-29 | Vertex Pharma | Piridon amidi kao modulatori natrijumovih kanala |
| RU2683788C2 (ru) | 2013-01-31 | 2019-04-02 | Вертекс Фармасьютикалз Инкорпорейтед | Амиды хинолина и хиназолина, полезные в качестве модуляторов натриевых каналов |
| UA119147C2 (uk) | 2013-07-19 | 2019-05-10 | Вертекс Фармасьютікалз Інкорпорейтед | Сульфонаміди як модулятори натрієвих каналів |
| CA2931550C (en) | 2013-12-13 | 2023-09-26 | Vertex Pharmaceuticals Incorporated | Prodrugs of pyridone amides useful as modulators of sodium channels |
| AU2018300150A1 (en) | 2017-07-11 | 2020-01-30 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| US11529337B2 (en) | 2018-02-12 | 2022-12-20 | Vertex Pharmaceuticals Incorporated | Method of treating pain |
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