JP2016525122A5 - - Google Patents
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- JP2016525122A5 JP2016525122A5 JP2016527141A JP2016527141A JP2016525122A5 JP 2016525122 A5 JP2016525122 A5 JP 2016525122A5 JP 2016527141 A JP2016527141 A JP 2016527141A JP 2016527141 A JP2016527141 A JP 2016527141A JP 2016525122 A5 JP2016525122 A5 JP 2016525122A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfamoylphenyl
- benzamide
- trifluoromethyl
- pain
- methoxyphenoxy
- 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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- 150000003839 salts Chemical class 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 50
- 208000002193 Pain Diseases 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 208000004296 neuralgia Diseases 0.000 claims description 13
- 208000021722 neuropathic pain Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 7
- 206010065390 Inflammatory pain Diseases 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 6
- 230000006378 damage Effects 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 208000005890 Neuroma Diseases 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010034620 Peripheral sensory neuropathy 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
- 239000001257 hydrogen Substances 0.000 claims description 4
- 210000005036 nerve Anatomy 0.000 claims description 4
- 201000005572 sensory peripheral neuropathy Diseases 0.000 claims description 4
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
- 230000007823 neuropathy Effects 0.000 claims description 3
- 230000003349 osteoarthritic effect Effects 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- GDAPYKKBLBYTMX-UHFFFAOYSA-N 2-(2-chloro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)-6-(trifluoromethyl)benzamide Chemical compound ClC1=CC(OC)=CC=C1OC1=CC=CC(C(F)(F)F)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 GDAPYKKBLBYTMX-UHFFFAOYSA-N 0.000 claims description 2
- NBMVKXLZBRBSKB-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-(3-sulfamoylphenyl)-6-(trifluoromethyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC=CC=2OC=2C(=CC=CC=2)Cl)C(F)(F)F)=C1 NBMVKXLZBRBSKB-UHFFFAOYSA-N 0.000 claims description 2
- JAZJBQYSZYFUEF-UHFFFAOYSA-N 2-(2-propoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound CCCOC1=CC=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 JAZJBQYSZYFUEF-UHFFFAOYSA-N 0.000 claims description 2
- TUQSVXNFVBKXJU-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethoxy)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(OC(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 TUQSVXNFVBKXJU-UHFFFAOYSA-N 0.000 claims description 2
- MGGSONOLOHCDPE-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-6-(trifluoromethyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC=CC(C(F)(F)F)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 MGGSONOLOHCDPE-UHFFFAOYSA-N 0.000 claims description 2
- ZUWPJBNZDVNRCL-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethoxy)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(OC(F)(F)F)=CC=2)OC=2C=CC(F)=CC=2)=C1 ZUWPJBNZDVNRCL-UHFFFAOYSA-N 0.000 claims description 2
- ALUKLBVCLDYRTQ-UHFFFAOYSA-N 4,5-dichloro-2-(2,4-dimethoxyphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound COC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 ALUKLBVCLDYRTQ-UHFFFAOYSA-N 0.000 claims description 2
- QUQAGYJLLRXYBS-UHFFFAOYSA-N 4,5-dichloro-2-(2-fluoro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound FC1=CC(OC)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 QUQAGYJLLRXYBS-UHFFFAOYSA-N 0.000 claims description 2
- CCXNRAYGQXCYHK-UHFFFAOYSA-N 4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 CCXNRAYGQXCYHK-UHFFFAOYSA-N 0.000 claims description 2
- JPJGZMFRWLIDAZ-UHFFFAOYSA-N 4-cyano-2-(4-fluoro-2-methylphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(C#N)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 JPJGZMFRWLIDAZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000008035 Back Pain Diseases 0.000 claims description 2
- 206010058019 Cancer Pain 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
- 101000654356 Homo sapiens Sodium channel protein type 10 subunit alpha Proteins 0.000 claims description 2
- 206010021639 Incontinence Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease 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
- 102100031374 Sodium channel protein type 10 subunit alpha Human genes 0.000 claims description 2
- 238000011225 antiretroviral therapy Methods 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 210000003461 brachial plexus Anatomy 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000002651 drug therapy Methods 0.000 claims description 2
- 231100000869 headache Toxicity 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
- 208000020431 spinal cord injury Diseases 0.000 claims description 2
- 230000036262 stenosis Effects 0.000 claims description 2
- 208000037804 stenosis Diseases 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 208000004371 toothache Diseases 0.000 claims description 2
- 230000000472 traumatic effect Effects 0.000 claims description 2
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 24
- -1 3-sulfamoylphenyl Chemical group 0.000 claims 11
- 208000004550 Postoperative Pain Diseases 0.000 claims 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 3
- 208000009935 visceral pain Diseases 0.000 claims 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 1
- UEYZYFUCYKOSPW-UHFFFAOYSA-N 2,4-dichloro-6-(2-fluoro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound FC1=CC(OC)=CC=C1OC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 UEYZYFUCYKOSPW-UHFFFAOYSA-N 0.000 claims 1
- RNZZISMBTWSALT-UHFFFAOYSA-N 2,4-dichloro-6-(4-chloro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound COC1=CC(Cl)=CC=C1OC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 RNZZISMBTWSALT-UHFFFAOYSA-N 0.000 claims 1
- BMIVUIPFPAOHMC-UHFFFAOYSA-N 2,4-dichloro-6-(4-fluoro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 BMIVUIPFPAOHMC-UHFFFAOYSA-N 0.000 claims 1
- PCMBTCRFWXBQNC-UHFFFAOYSA-N 2,4-dichloro-6-(4-fluoro-2-methylphenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 PCMBTCRFWXBQNC-UHFFFAOYSA-N 0.000 claims 1
- NMLQQAHRNXQEFD-UHFFFAOYSA-N 2,4-dichloro-6-(4-fluorophenoxy)-n-(3-sulfamoylphenyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(Cl)=CC=2Cl)OC=2C=CC(F)=CC=2)=C1 NMLQQAHRNXQEFD-UHFFFAOYSA-N 0.000 claims 1
- YOKWHBZXAZLEFL-UHFFFAOYSA-N 2,4-dichloro-n-(3-sulfamoylphenyl)-6-[4-(trifluoromethoxy)phenoxy]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(Cl)=CC=2Cl)OC=2C=CC(OC(F)(F)F)=CC=2)=C1 YOKWHBZXAZLEFL-UHFFFAOYSA-N 0.000 claims 1
- YLUWVMSCCKTLOH-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(=CC=2)C(F)(F)F)OC=2C(=CC(F)=CC=2)F)=C1 YLUWVMSCCKTLOH-UHFFFAOYSA-N 0.000 claims 1
- RMAKWANTNZBDRA-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)OC=2C(=CC(F)=CC=2)F)=C1 RMAKWANTNZBDRA-UHFFFAOYSA-N 0.000 claims 1
- MNRMMRMQCIGRBU-UHFFFAOYSA-N 2-(2,4-dimethoxyphenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 MNRMMRMQCIGRBU-UHFFFAOYSA-N 0.000 claims 1
- GNSNUJNIEWACEC-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-4-cyano-n-(3-sulfamoylphenyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(=CC=2)C#N)OC=2C(=CC(F)=CC=2)Cl)=C1 GNSNUJNIEWACEC-UHFFFAOYSA-N 0.000 claims 1
- YUZYENYAUKFUKJ-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-5-cyano-n-(3-sulfamoylphenyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC=C(C=2)C#N)OC=2C(=CC(F)=CC=2)Cl)=C1 YUZYENYAUKFUKJ-UHFFFAOYSA-N 0.000 claims 1
- RGZJXURZZYFNMU-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethoxy)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(OC(F)(F)F)=CC=2)OC=2C(=CC(F)=CC=2)Cl)=C1 RGZJXURZZYFNMU-UHFFFAOYSA-N 0.000 claims 1
- IDBBYSABYAPIPY-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)OC=2C(=CC(F)=CC=2)Cl)=C1 IDBBYSABYAPIPY-UHFFFAOYSA-N 0.000 claims 1
- GLYONJOHRRWFQM-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-n-(3-sulfamoylphenyl)-6-(trifluoromethyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC=CC=2OC=2C(=CC(F)=CC=2)Cl)C(F)(F)F)=C1 GLYONJOHRRWFQM-UHFFFAOYSA-N 0.000 claims 1
- MFHUOOPGPQUNMS-UHFFFAOYSA-N 2-(2-chloro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethoxy)benzamide Chemical compound ClC1=CC(OC)=CC=C1OC1=CC(OC(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 MFHUOOPGPQUNMS-UHFFFAOYSA-N 0.000 claims 1
- ZMECPDMZMKHKLY-UHFFFAOYSA-N 2-(2-chloro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound ClC1=CC(OC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 ZMECPDMZMKHKLY-UHFFFAOYSA-N 0.000 claims 1
- VNJBIHYNYPMISF-UHFFFAOYSA-N 2-(2-chloro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound ClC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 VNJBIHYNYPMISF-UHFFFAOYSA-N 0.000 claims 1
- PSKFFOPVTRAFGH-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethoxy)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(OC(F)(F)F)=CC=2)OC=2C(=CC=CC=2)Cl)=C1 PSKFFOPVTRAFGH-UHFFFAOYSA-N 0.000 claims 1
- OXHGDUJQQGLHPV-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC(=CC=2)C(F)(F)F)OC=2C(=CC=CC=2)Cl)=C1 OXHGDUJQQGLHPV-UHFFFAOYSA-N 0.000 claims 1
- BFJOQZKSSLACKF-UHFFFAOYSA-N 2-(2-fluoro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4,6-bis(trifluoromethyl)benzamide Chemical compound FC1=CC(OC)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 BFJOQZKSSLACKF-UHFFFAOYSA-N 0.000 claims 1
- AJQUXEOVUMRFJR-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound COC1=CC=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 AJQUXEOVUMRFJR-UHFFFAOYSA-N 0.000 claims 1
- FGHRJOAEJLKIBZ-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 FGHRJOAEJLKIBZ-UHFFFAOYSA-N 0.000 claims 1
- YUGVYVNFJHZSRT-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-6-(trifluoromethyl)benzamide Chemical compound COC1=CC=CC=C1OC1=CC=CC(C(F)(F)F)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 YUGVYVNFJHZSRT-UHFFFAOYSA-N 0.000 claims 1
- RGLBPVFURSZMTH-UHFFFAOYSA-N 2-(3-chloro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethoxy)benzamide Chemical compound COC1=C(Cl)C=CC=C1OC1=CC(OC(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 RGLBPVFURSZMTH-UHFFFAOYSA-N 0.000 claims 1
- PGQZXULSUGGSID-UHFFFAOYSA-N 2-(3-chloro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound COC1=C(Cl)C=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 PGQZXULSUGGSID-UHFFFAOYSA-N 0.000 claims 1
- JBJGODQCEGRHGM-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(OC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 JBJGODQCEGRHGM-UHFFFAOYSA-N 0.000 claims 1
- HXNKWCGOQXNUAR-UHFFFAOYSA-N 2-(3-fluoro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound COC1=C(F)C=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 HXNKWCGOQXNUAR-UHFFFAOYSA-N 0.000 claims 1
- QPVFFGGJYLWDCI-UHFFFAOYSA-N 2-(3-fluoro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound COC1=C(F)C=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 QPVFFGGJYLWDCI-UHFFFAOYSA-N 0.000 claims 1
- GWVLZDHEZXYWQV-UHFFFAOYSA-N 2-(3-fluoro-2-methylphenoxy)-n-(3-sulfamoylphenyl)-6-(trifluoromethyl)benzamide Chemical compound CC1=C(F)C=CC=C1OC1=CC=CC(C(F)(F)F)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 GWVLZDHEZXYWQV-UHFFFAOYSA-N 0.000 claims 1
- KAYRZLWFCJSCJU-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4,6-bis(trifluoromethyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 KAYRZLWFCJSCJU-UHFFFAOYSA-N 0.000 claims 1
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- ZXRGUFCLRCPMEQ-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethoxy)benzamide Chemical compound COC1=CC(Cl)=CC=C1OC1=CC(OC(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 ZXRGUFCLRCPMEQ-UHFFFAOYSA-N 0.000 claims 1
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- QGCPMZOILOAXFC-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC(Cl)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 QGCPMZOILOAXFC-UHFFFAOYSA-N 0.000 claims 1
- VZFDHOXVBHNNKD-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(Cl)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 VZFDHOXVBHNNKD-UHFFFAOYSA-N 0.000 claims 1
- TXOAOGMIUNBRND-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(3-sulfamoylphenyl)-5-(trifluoromethyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)OC=2C=CC(Cl)=CC=2)=C1 TXOAOGMIUNBRND-UHFFFAOYSA-N 0.000 claims 1
- ISQJMVKGBSZKDT-UHFFFAOYSA-N 2-(4-ethoxyphenoxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OCC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(S(N)(=O)=O)=C1 ISQJMVKGBSZKDT-UHFFFAOYSA-N 0.000 claims 1
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