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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| CN102659628B (zh) * | 2012-04-26 | 2014-07-02 | 四川大学 | 含芳酰胺的邻苯二甲腈单体及其合成方法和用其固化制备的聚邻苯二甲腈树脂 |
| CN105073738B (zh) | 2013-01-31 | 2018-01-05 | 沃泰克斯药物股份有限公司 | 作为钠通道调节剂的喹啉及喹喔啉酰胺类 |
| AR094668A1 (es) | 2013-01-31 | 2015-08-19 | Vertex Pharma | Amidas como moduladores de canales de sodio |
| TWI606048B (zh) | 2013-01-31 | 2017-11-21 | 帝人製藥股份有限公司 | 唑苯衍生物 |
| ES2857687T3 (es) | 2013-01-31 | 2021-09-29 | Vertex Pharma | Piridona amidas como moduladores de los canales de sodio |
| PE20160548A1 (es) | 2013-07-19 | 2016-05-21 | Vertex Pharma | Sulfonamidas como moduladores de canales de sodio |
| CA2931550C (en) | 2013-12-13 | 2023-09-26 | Vertex Pharmaceuticals Incorporated | Prodrugs of pyridone amides useful as modulators of sodium channels |
| CA3069720A1 (en) | 2017-07-11 | 2019-01-17 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| WO2019157505A1 (en) | 2018-02-12 | 2019-08-15 | Vertex Pharmaceuticals Incorporated | A method of treating pain |
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