JP2016508500A5 - - Google Patents
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- Publication number
- JP2016508500A5 JP2016508500A5 JP2015556113A JP2015556113A JP2016508500A5 JP 2016508500 A5 JP2016508500 A5 JP 2016508500A5 JP 2015556113 A JP2015556113 A JP 2015556113A JP 2015556113 A JP2015556113 A JP 2015556113A JP 2016508500 A5 JP2016508500 A5 JP 2016508500A5
- Authority
- JP
- Japan
- Prior art keywords
- benzamido
- alkyl
- pain
- halogen
- pharmaceutically acceptable
- 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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- 229910052736 halogen Inorganic materials 0.000 claims description 102
- 150000002367 halogens Chemical class 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 45
- 208000002193 Pain Diseases 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 28
- 208000004296 neuralgia Diseases 0.000 claims description 14
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 208000021722 neuropathic pain Diseases 0.000 claims description 7
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 206010065390 Inflammatory pain Diseases 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 210000005036 nerve Anatomy 0.000 claims description 5
- -1 t- butyl Chemical group 0.000 claims description 5
- 208000005890 Neuroma Diseases 0.000 claims description 4
- 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 claims description 4
- 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 206010034620 Peripheral sensory neuropathy Diseases 0.000 claims description 3
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
- 208000010261 Small Fiber Neuropathy Diseases 0.000 claims description 3
- 206010073928 Small fibre neuropathy Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000000968 intestinal effect Effects 0.000 claims description 3
- 230000003349 osteoarthritic effect Effects 0.000 claims description 3
- 208000017692 primary erythermalgia Diseases 0.000 claims description 3
- 201000005572 sensory peripheral neuropathy Diseases 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- POHBHELIQIIUKS-UHFFFAOYSA-N 3-methyl-4-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 POHBHELIQIIUKS-UHFFFAOYSA-N 0.000 claims description 2
- SZKVUKWDHVSELR-UHFFFAOYSA-N 4-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 SZKVUKWDHVSELR-UHFFFAOYSA-N 0.000 claims description 2
- ZYORVEKORXNUEM-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZYORVEKORXNUEM-UHFFFAOYSA-N 0.000 claims description 2
- CCFLCDDJGGMPDK-UHFFFAOYSA-N 4-[[2-[4-(trifluoromethoxy)phenoxy]-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(OC(F)(F)F)C=C1 CCFLCDDJGGMPDK-UHFFFAOYSA-N 0.000 claims description 2
- DZORGHOZKZHPLX-UHFFFAOYSA-N 4-[[4,5-dichloro-2-[4-(2,2,2-trifluoroethoxy)phenoxy]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(OCC(F)(F)F)C=C1 DZORGHOZKZHPLX-UHFFFAOYSA-N 0.000 claims description 2
- QPVZBOZWYRYQOY-UHFFFAOYSA-N 5-[[2-(2-chlorophenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1OC1=CC=CC=C1Cl QPVZBOZWYRYQOY-UHFFFAOYSA-N 0.000 claims description 2
- IUYUKZBMJINCLE-UHFFFAOYSA-N 5-[[2-(4-fluorophenoxy)-4-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(F)C=C1 IUYUKZBMJINCLE-UHFFFAOYSA-N 0.000 claims description 2
- NBWXLOUGPHXUKY-UHFFFAOYSA-N 5-[[2-(4-methoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)N=C1 NBWXLOUGPHXUKY-UHFFFAOYSA-N 0.000 claims description 2
- LFHRVAHCKMGOPT-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(2,4-dimethoxyphenoxy)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 LFHRVAHCKMGOPT-UHFFFAOYSA-N 0.000 claims description 2
- CGCFKBNXDFEYIJ-UHFFFAOYSA-N 5-[[4,5-dichloro-2-[2-(difluoromethoxy)phenoxy]benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1OC(F)F CGCFKBNXDFEYIJ-UHFFFAOYSA-N 0.000 claims description 2
- VJNROMFRLBVAHF-UHFFFAOYSA-N 5-chloro-2-methoxy-4-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC(=O)C=2C(=CC=CC=2)OC=2C=CC=CC=2)=C1Cl VJNROMFRLBVAHF-UHFFFAOYSA-N 0.000 claims description 2
- 206010003497 Asphyxia Diseases 0.000 claims description 2
- 208000008035 Back Pain Diseases 0.000 claims description 2
- 206010058019 Cancer Pain Diseases 0.000 claims description 2
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 206010021639 Incontinence Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000005615 Interstitial Cystitis Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 2
- 208000004983 Phantom Limb Diseases 0.000 claims description 2
- 206010056238 Phantom pain Diseases 0.000 claims description 2
- 208000008765 Sciatica Diseases 0.000 claims description 2
- 238000011225 antiretroviral therapy Methods 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000036262 stenosis Effects 0.000 claims description 2
- 208000037804 stenosis Diseases 0.000 claims description 2
- 230000000472 traumatic effect Effects 0.000 claims description 2
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
- 208000004550 Postoperative Pain Diseases 0.000 claims 3
- ZWSJDCCDISWMKX-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-5-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZWSJDCCDISWMKX-UHFFFAOYSA-N 0.000 claims 2
- KXJDXJMNXMKFQA-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 KXJDXJMNXMKFQA-UHFFFAOYSA-N 0.000 claims 2
- IFLJQZOHWQKXBE-UHFFFAOYSA-N 3-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound O(C1=CC=CC=C1)C1=C(C(=O)NC=2C=C(C(=O)O)C=CC=2)C=CC=C1 IFLJQZOHWQKXBE-UHFFFAOYSA-N 0.000 claims 1
- MZIVXQQTMDYTAZ-UHFFFAOYSA-N 4-[[2-(2,4-difluorophenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C(C(=CC(=C1)C(F)(F)F)C(F)(F)F)=C1OC1=CC=C(F)C=C1F MZIVXQQTMDYTAZ-UHFFFAOYSA-N 0.000 claims 1
- LLGVNUHNAGGBMF-UHFFFAOYSA-N 4-[[2-(2,4-difluorophenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)C(F)(F)F)C=C1OC1=CC=C(F)C=C1F LLGVNUHNAGGBMF-UHFFFAOYSA-N 0.000 claims 1
- MRBUJXKMAOIITA-UHFFFAOYSA-N 4-[[2-(2,4-difluorophenoxy)-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(F)C=C1F MRBUJXKMAOIITA-UHFFFAOYSA-N 0.000 claims 1
- BAVGXISUWOMPHG-UHFFFAOYSA-N 4-[[2-(2-chloro-4-fluorophenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)C(F)(F)F)C=C1OC1=CC=C(F)C=C1Cl BAVGXISUWOMPHG-UHFFFAOYSA-N 0.000 claims 1
- CAROJXJPUIPNPU-UHFFFAOYSA-N 4-[[2-(2-chloro-4-fluorophenoxy)-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1OC1=CC=C(F)C=C1Cl CAROJXJPUIPNPU-UHFFFAOYSA-N 0.000 claims 1
- ZDFFCDWYMIMFCV-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methoxyphenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZDFFCDWYMIMFCV-UHFFFAOYSA-N 0.000 claims 1
- IZPCPMZRYGDVDG-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)C=C1 IZPCPMZRYGDVDG-UHFFFAOYSA-N 0.000 claims 1
- AFMYVWVPIHWHLQ-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-4-(1,1,2,2,2-pentafluoroethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC=C(C(O)=O)C=C1 AFMYVWVPIHWHLQ-UHFFFAOYSA-N 0.000 claims 1
- WHSJMGMHKHPGIL-UHFFFAOYSA-N 4-[[2-(4-fluoro-2-methylphenoxy)-4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(C(O)=O)C=C1 WHSJMGMHKHPGIL-UHFFFAOYSA-N 0.000 claims 1
- FOTNRCKKBGVZMV-UHFFFAOYSA-N 4-[[2-(4-fluorophenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C(C(=CC(=C1)C(F)(F)F)C(F)(F)F)=C1OC1=CC=C(F)C=C1 FOTNRCKKBGVZMV-UHFFFAOYSA-N 0.000 claims 1
- WHKNHAUMJCTTLG-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2,4-difluorophenoxy)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(F)C=C1F WHKNHAUMJCTTLG-UHFFFAOYSA-N 0.000 claims 1
- PVLVVQUGLDODSS-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2,4-dimethoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 PVLVVQUGLDODSS-UHFFFAOYSA-N 0.000 claims 1
- OOZXERKWFWPVJT-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2-chloro-4-fluorophenoxy)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(F)C=C1Cl OOZXERKWFWPVJT-UHFFFAOYSA-N 0.000 claims 1
- ZTXIJQTYASXCNZ-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2-chloro-4-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound ClC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZTXIJQTYASXCNZ-UHFFFAOYSA-N 0.000 claims 1
- LMNGTJLHWMMCFG-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(2-fluoro-4-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound FC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 LMNGTJLHWMMCFG-UHFFFAOYSA-N 0.000 claims 1
- BOWBWUKGDFJJDA-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(3-fluoro-4-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound C1=C(F)C(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 BOWBWUKGDFJJDA-UHFFFAOYSA-N 0.000 claims 1
- FYSNDWMSTSNSPW-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-chloro-2-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound COC1=CC(Cl)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 FYSNDWMSTSNSPW-UHFFFAOYSA-N 0.000 claims 1
- ZPTZKRNZFFQAKZ-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-chloro-2-methylphenoxy)benzoyl]amino]benzoic acid Chemical compound CC1=CC(Cl)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 ZPTZKRNZFFQAKZ-UHFFFAOYSA-N 0.000 claims 1
- JPVADBDXDGHZBJ-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)benzoyl]amino]benzoic acid Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 JPVADBDXDGHZBJ-UHFFFAOYSA-N 0.000 claims 1
- OFOIUNYHRNAMCV-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-fluoro-2-methylphenoxy)benzoyl]amino]benzoic acid Chemical compound CC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 OFOIUNYHRNAMCV-UHFFFAOYSA-N 0.000 claims 1
- MECYBMKMICVTAK-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(4-fluorophenoxy)benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(F)C=C1 MECYBMKMICVTAK-UHFFFAOYSA-N 0.000 claims 1
- TWHKITDGPNXHCU-UHFFFAOYSA-N 4-[[4,5-dichloro-2-[2-(difluoromethoxy)phenoxy]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1OC(F)F TWHKITDGPNXHCU-UHFFFAOYSA-N 0.000 claims 1
- NJFDHBSKHZPRIL-UHFFFAOYSA-N 4-[[4,5-dichloro-2-[4-(trifluoromethoxy)phenoxy]benzoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=C(OC(F)(F)F)C=C1 NJFDHBSKHZPRIL-UHFFFAOYSA-N 0.000 claims 1
- JXVMPMSRFGGAGY-UHFFFAOYSA-N 4-chloro-3-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound ClC1=C(C=C(C(=O)O)C=C1)NC(C1=C(C=CC=C1)OC1=CC=CC=C1)=O JXVMPMSRFGGAGY-UHFFFAOYSA-N 0.000 claims 1
- WRZOPENWRAIPLT-UHFFFAOYSA-N 4-methyl-3-[(2-phenoxybenzoyl)amino]benzoic acid Chemical compound CC1=C(C=C(C(=O)O)C=C1)NC(C1=C(C=CC=C1)OC1=CC=CC=C1)=O WRZOPENWRAIPLT-UHFFFAOYSA-N 0.000 claims 1
- SEAWCQYTEVZJDD-UHFFFAOYSA-N 5-[(4,5-dichloro-2-phenoxybenzoyl)amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 SEAWCQYTEVZJDD-UHFFFAOYSA-N 0.000 claims 1
- JFTGNYZRKUMSAG-UHFFFAOYSA-N 5-[[2-(2,4-dimethoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)N=C1 JFTGNYZRKUMSAG-UHFFFAOYSA-N 0.000 claims 1
- NOKQAGXWKAATRB-UHFFFAOYSA-N 5-[[2-(2,4-dimethoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 NOKQAGXWKAATRB-UHFFFAOYSA-N 0.000 claims 1
- ZJDFLPLEPVWDIP-UHFFFAOYSA-N 5-[[2-(2-chloro-4-fluorophenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(F)C=C1Cl ZJDFLPLEPVWDIP-UHFFFAOYSA-N 0.000 claims 1
- KTHRLYGNINDXBX-UHFFFAOYSA-N 5-[[2-(2-chloro-4-fluorophenoxy)-6-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC(=O)C(C(=CC=C1)C(F)(F)F)=C1OC1=CC=C(F)C=C1Cl KTHRLYGNINDXBX-UHFFFAOYSA-N 0.000 claims 1
- HKWSUHGMFVMEIM-UHFFFAOYSA-N 5-[[2-(2-chloro-4-methoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound ClC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 HKWSUHGMFVMEIM-UHFFFAOYSA-N 0.000 claims 1
- QOJHXRSRBOSGMJ-UHFFFAOYSA-N 5-[[2-(2-methoxyphenoxy)-4,6-bis(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=C(C(O)=O)N=C1 QOJHXRSRBOSGMJ-UHFFFAOYSA-N 0.000 claims 1
- BQNMADFVJFWVJU-UHFFFAOYSA-N 5-[[2-(2-methoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 BQNMADFVJFWVJU-UHFFFAOYSA-N 0.000 claims 1
- SCVAJTQTAYTWBF-UHFFFAOYSA-N 5-[[2-(2-propan-2-yloxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound CC(C)OC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 SCVAJTQTAYTWBF-UHFFFAOYSA-N 0.000 claims 1
- BIRRZQIINJYINB-UHFFFAOYSA-N 5-[[2-(3-fluoro-2-methoxyphenoxy)-5-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid Chemical compound COC1=C(F)C=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(C(O)=O)N=C1 BIRRZQIINJYINB-UHFFFAOYSA-N 0.000 claims 1
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| NZ710270A (en) | 2013-01-31 | 2020-09-25 | Vertex Pharma | Pyridone amides as modulators of sodium channels |
| KR102226587B1 (ko) | 2013-01-31 | 2021-03-11 | 버텍스 파마슈티칼스 인코포레이티드 | 나트륨 채널의 조절제로서의 퀴놀린 및 퀴나졸린 아미드 |
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| EP3625214B1 (en) | 2017-05-16 | 2022-07-06 | Vertex Pharmaceuticals Incorporated | Deuterated pyridone amides and prodrugs thereof as modulators of sodium channels |
| BR112020000553A2 (pt) | 2017-07-11 | 2020-07-21 | Vertex Pharmaceuticals Incorporated | carboxamidas como moduladores de canal de sódio |
| US20190343817A1 (en) | 2018-02-12 | 2019-11-14 | Vertex Pharmaceuticals Incorporated | Method of treating pain |
| WO2020092187A1 (en) | 2018-11-02 | 2020-05-07 | Merck Sharp & Dohme Corp. | 2-amino-n-phenyl-nicotinamides as nav1.8 inhibitors |
| KR102860523B1 (ko) | 2018-11-02 | 2025-09-16 | 머크 샤프 앤드 돔 엘엘씨 | Nav1.8 억제제로서의 2-아미노-n-헤테로아릴-니코틴아미드 |
| AU2020205139A1 (en) * | 2019-01-04 | 2021-08-19 | Jiangsu Hengrui Medicine Co., Ltd. | 6-oxo-1,6-dihydropyridazine derivative, preparation method therefor and medical use thereof |
| US12441703B2 (en) | 2019-01-10 | 2025-10-14 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| WO2020146612A1 (en) | 2019-01-10 | 2020-07-16 | Vertex Pharmaceuticals Incorporated | Esters and carbamates as modulators of sodium channels |
| US20220162169A1 (en) * | 2019-02-20 | 2022-05-26 | Jiangsu Hengrui Medicine Co., Ltd. | 6-oxo-1,6-dihydropyridazine prodrug derivative, preparation method therefor, and application thereof in medicine |
| WO2020176763A1 (en) | 2019-02-27 | 2020-09-03 | Vertex Pharmaceuticals Incorporated | Dosage form comprising prodrug of na 1.8 sodium channel inhibitor |
| WO2020219867A1 (en) | 2019-04-25 | 2020-10-29 | Vertex Pharmaceuticals Incorporated | Pyridone amide co-crystal compositions for the treatment of pain |
| CN112479996B (zh) * | 2019-09-12 | 2023-05-26 | 上海济煜医药科技有限公司 | 吡啶氮氧化合物及其制备方法和用途 |
| AU2020397059A1 (en) * | 2019-12-06 | 2022-07-21 | Vertex Pharmaceuticals Incorporated | Substituted tetrahydrofurans as modulators of sodium channels |
| CN114437062B (zh) * | 2020-04-30 | 2024-05-17 | 成都海博为药业有限公司 | 一种可作为钠通道调节剂的化合物及其用途 |
| US12516046B2 (en) | 2020-06-17 | 2026-01-06 | Merck Sharp & Dohme Llc | 2-oxo-oxazolidine-5-carboxamides as NAV1.8 inhibitors |
| CR20220642A (es) | 2020-06-17 | 2023-02-15 | Merck Sharp & Dohme Llc | 2-oxoimidazolidin-4-carboxamidas como inhibidores de nav1.8 |
| CN113880771B (zh) * | 2020-07-03 | 2023-09-19 | 福建盛迪医药有限公司 | 一种选择性Nav抑制剂的结晶形式及其制备方法 |
| CN114031518B (zh) * | 2020-12-08 | 2023-08-18 | 成都海博为药业有限公司 | 一种苄胺或苄醇衍生物及其用途 |
| CN112225695B (zh) * | 2020-12-15 | 2021-03-02 | 上海济煜医药科技有限公司 | 一种氮氧化合物及其制备方法和用途 |
| BR112023018348A2 (pt) * | 2021-03-11 | 2023-12-05 | Jiangxi Jemincare Group Co Ltd | Forma de cristal de composto de óxido de nitrogênio e piridina e uso da mesma |
| CA3217565A1 (en) | 2021-05-07 | 2022-11-10 | Ashok Arasappan | Cycloalkyl 3-oxopiperazine carboxamides and cycloheteroalkyl 3-oxopiperazine carboxamides as nav1.8 inhibitors |
| CN117794918A (zh) | 2021-06-04 | 2024-03-29 | 沃泰克斯药物股份有限公司 | 经取代的四氢呋喃类似物作为钠通道调节剂 |
| US20240368135A1 (en) | 2021-06-04 | 2024-11-07 | Vertex Pharmaceuticals Incorporated | Substituted tetrahydrofuran-2-carboxamides as modulators of sodium channels |
| AU2022286511A1 (en) | 2021-06-04 | 2023-11-30 | Vertex Pharmaceuticals Incorporated | Hydroxy and (halo)alkoxy substituted tetrahydrofurans as modulators of sodium channels |
| US20240400544A1 (en) | 2021-06-04 | 2024-12-05 | Vertex Pharmaceuticals Incorporated | N-(hydroxyalkyl (hetero)aryl) tetrahydrofuran carboxamide analogs as modulators of sodium channels |
| IL308954A (en) | 2021-06-04 | 2024-01-01 | Vertex Pharma | Solid dosage forms and dosing regimens comprising (2r,3s,4s,5r)-4-[[3-(3,4-difluoro-2-methoxy-phenyl)-4,5-dimethyl-5-(trifluoromethyl) tetrahydrofuran-2-carbonyl]amino]pyridine-2-carboxamide |
| CN117794920A (zh) | 2021-06-04 | 2024-03-29 | 沃泰克斯药物股份有限公司 | N-(羟烷基(杂)芳基)四氢呋喃甲酰胺作为钠通道调节剂 |
| EP4511116A1 (en) | 2022-04-22 | 2025-02-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| CN119522214A (zh) | 2022-04-22 | 2025-02-25 | 沃泰克斯药物股份有限公司 | 用于治疗疼痛的杂芳基化合物 |
| US20250388543A1 (en) | 2022-04-22 | 2025-12-25 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| JP2025513452A (ja) | 2022-04-22 | 2025-04-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | 疼痛の治療のためのヘテロアリール化合物 |
| PE20251183A1 (es) | 2022-04-25 | 2025-04-23 | Siteone Therapeutics Inc | Inhibidores de amida heterociclica biciclica de sodio activado por voltaje 1.8 (nav 1.8) para el tratamiento del dolor |
| JP2026501116A (ja) | 2022-12-06 | 2026-01-14 | バーテックス ファーマシューティカルズ インコーポレイテッド | ナトリウムチャネルの置換テトラヒドロフラン調節因子の合成のための製造方法 |
| WO2024153856A1 (en) * | 2023-01-18 | 2024-07-25 | Orion Corporation | Process for the preparation of 3-(4,5-dichloro-2-(4-(trifluoromethoxy)phenoxy)benzamido)pyridine 1-oxide |
| WO2025090516A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Methods of preparing compounds for treating pain and solid forms thereof |
| WO2025090465A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| WO2025090480A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| WO2025090511A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Methods of preparing modulators of sodium channels and solid forms of the same for treating pain |
| WO2025122953A1 (en) | 2023-12-07 | 2025-06-12 | Vertex Pharmaceuticals Incorporated | Dosing regimens and formulations of suzetrigine for use in the treatment of acute and chronic pain |
| WO2025160286A1 (en) | 2024-01-24 | 2025-07-31 | Siteone Therapeutics, Inc. | 2-aryl cycloalkyl and heterocycloalkyl inhibitors of nav1.8 for the treatment of pain |
| WO2026006674A1 (en) | 2024-06-28 | 2026-01-02 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| WO2026013449A2 (en) | 2024-07-11 | 2026-01-15 | Sea4Us - Biotecnologia E Recursos Marinhos, Sa | Oxazolidone-derived compounds and their use in the treatment of chronic and acute pain |
Family Cites Families (6)
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| US8841483B2 (en) | 2006-04-11 | 2014-09-23 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of voltage-gated sodium channels |
| US8519137B2 (en) | 2007-10-11 | 2013-08-27 | Vertex Pharmaceuticals Incorporated | Heteroaryl amides useful as inhibitors of voltage-gated sodium channels |
| EP2212292B1 (en) | 2007-10-11 | 2012-12-05 | Vertex Pharmaceuticals Incorporated | Amides useful as inhibitors of voltage-gated sodium channels |
| MX2010003865A (es) * | 2007-10-11 | 2010-06-01 | Vertex Pharma | Aril amidas utiles como inhibidores de canales de sodio dependientes de voltaje. |
| US9101616B2 (en) * | 2009-05-29 | 2015-08-11 | Raqualia Pharma Inc. | Aryl substituted carboxamide derivatives as calcium or sodium channel blockers |
-
2014
- 2014-01-29 TW TW103103690A patent/TWI659945B/zh active
- 2014-01-29 CA CA2898653A patent/CA2898653C/en active Active
- 2014-01-29 JP JP2015556113A patent/JP6346622B2/ja active Active
- 2014-01-29 MX MX2015009591A patent/MX359882B/es active IP Right Grant
- 2014-01-29 WO PCT/US2014/013667 patent/WO2014120820A1/en not_active Ceased
- 2014-01-29 CN CN201480006878.4A patent/CN104968647B/zh active Active
- 2014-01-29 BR BR112015018284-4A patent/BR112015018284B1/pt not_active IP Right Cessation
- 2014-01-29 AR ARP140100282A patent/AR094668A1/es unknown
- 2014-01-29 SG SG11201505954RA patent/SG11201505954RA/en unknown
- 2014-01-29 KR KR1020157023600A patent/KR102226588B1/ko not_active Expired - Fee Related
- 2014-01-29 EP EP14704981.1A patent/EP2951155B1/en active Active
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