JP2006525298A5 - - Google Patents
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- JP2006525298A5 JP2006525298A5 JP2006506198A JP2006506198A JP2006525298A5 JP 2006525298 A5 JP2006525298 A5 JP 2006525298A5 JP 2006506198 A JP2006506198 A JP 2006506198A JP 2006506198 A JP2006506198 A JP 2006506198A JP 2006525298 A5 JP2006525298 A5 JP 2006525298A5
- Authority
- JP
- Japan
- Prior art keywords
- azetidine
- carboxamide
- trifluoromethyl
- butyl
- dichlorobenzhydryloxy
- 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.)
- Pending
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- -1 2,4'-Dichlorobenzhydryloxy Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- PVXOUGHWLCBJOW-UHFFFAOYSA-N azetidine-1-carboxamide Chemical compound NC(=O)N1CCC1 PVXOUGHWLCBJOW-UHFFFAOYSA-N 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 235000014632 disordered eating Nutrition 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229960002715 nicotine Drugs 0.000 claims 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 3
- 201000009032 substance abuse Diseases 0.000 claims 3
- 125000004001 thioalkyl group Chemical group 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 2
- 208000010643 digestive system disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000037406 food intake Effects 0.000 claims 2
- 235000012631 food intake Nutrition 0.000 claims 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000005586 smoking cessation Effects 0.000 claims 2
- 231100000736 substance abuse Toxicity 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- LAXPNMTYJFUPLS-UHFFFAOYSA-N 3-[(2-chlorophenyl)-(4-chlorophenyl)methoxy]-n-(2-methylbutan-2-yl)azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)CC)CC1OC(C=1C(=CC=CC=1)Cl)C1=CC=C(Cl)C=C1 LAXPNMTYJFUPLS-UHFFFAOYSA-N 0.000 claims 1
- PTVKXSFBTUPKHX-UHFFFAOYSA-N 3-[(4-bromo-2-fluorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]-n-tert-butylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(Br)C=C1F PTVKXSFBTUPKHX-UHFFFAOYSA-N 0.000 claims 1
- NIHKEECPBZMVNP-KEJDIYNNSA-N 3-[(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]-n-[(1s)-1-phenylethyl]azetidine-1-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)N(C1)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(Cl)C=C1 NIHKEECPBZMVNP-KEJDIYNNSA-N 0.000 claims 1
- SXKYOXHYTLPEKN-UHFFFAOYSA-N 3-[(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]-n-cyclohexylazetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=1C=CC(Cl)=CC=1)OC1CN(C(=O)NC2CCCCC2)C1 SXKYOXHYTLPEKN-UHFFFAOYSA-N 0.000 claims 1
- HWLAWTMTIUBMRV-UHFFFAOYSA-N 3-[(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]-n-prop-2-enylazetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=1C=CC(Cl)=CC=1)OC1CN(C(=O)NCC=C)C1 HWLAWTMTIUBMRV-UHFFFAOYSA-N 0.000 claims 1
- FCGQYTCSXQCYAE-KEJDIYNNSA-N 3-[(4-fluorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]-n-[(1s)-1-phenylethyl]azetidine-1-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)N(C1)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(F)C=C1 FCGQYTCSXQCYAE-KEJDIYNNSA-N 0.000 claims 1
- LSJZXKGOYIYDQD-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]-n-prop-2-enylazetidine-1-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NCC=C)C1 LSJZXKGOYIYDQD-UHFFFAOYSA-N 0.000 claims 1
- WMDFBQORZPFSTC-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]-n-propan-2-ylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)C)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(OC(F)F)C=C1 WMDFBQORZPFSTC-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010020710 Hyperphagia Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- ZDEVQOADMXOMDO-UHFFFAOYSA-N n-(1-adamantyl)-3-[(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=1C=CC(Cl)=CC=1)OC1CN(C(=O)NC23CC4CC(CC(C4)C2)C3)C1 ZDEVQOADMXOMDO-UHFFFAOYSA-N 0.000 claims 1
- JWESBCIKCOHJSY-UHFFFAOYSA-N n-(1-adamantyl)-3-[(4-fluorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC23CC4CC(CC(C4)C2)C3)C1 JWESBCIKCOHJSY-UHFFFAOYSA-N 0.000 claims 1
- PZIOEWGGOWVPEF-UHFFFAOYSA-N n-(1-adamantyl)-3-[(4-methoxyphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC23CC4CC(CC(C4)C2)C3)C1 PZIOEWGGOWVPEF-UHFFFAOYSA-N 0.000 claims 1
- WJBNQPICTCHOQS-UHFFFAOYSA-N n-(1-adamantyl)-3-[(4-methylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC23CC4CC(CC(C4)C2)C3)C1 WJBNQPICTCHOQS-UHFFFAOYSA-N 0.000 claims 1
- CENFVFWZOPWHSC-UHFFFAOYSA-N n-(1-adamantyl)-3-[(4-methylsulfanylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(SC)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC23CC4CC(CC(C4)C2)C3)C1 CENFVFWZOPWHSC-UHFFFAOYSA-N 0.000 claims 1
- BOEIGWVMFZGJKU-UHFFFAOYSA-N n-benzyl-3-[(4-chlorophenyl)-[4-fluoro-2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1C(C=1C=CC(Cl)=CC=1)OC1CN(C(=O)NCC=2C=CC=CC=2)C1 BOEIGWVMFZGJKU-UHFFFAOYSA-N 0.000 claims 1
- VGZODVVTKYTELC-UHFFFAOYSA-N n-benzyl-3-[(4-methylsulfanylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(SC)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NCC=2C=CC=CC=2)C1 VGZODVVTKYTELC-UHFFFAOYSA-N 0.000 claims 1
- AALJQBMGLBJRRK-UHFFFAOYSA-N n-benzyl-3-[[4-(trifluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NCC=2C=CC=CC=2)C1 AALJQBMGLBJRRK-UHFFFAOYSA-N 0.000 claims 1
- AYFRSZYMSBZIOY-UHFFFAOYSA-N n-benzyl-3-[phenyl-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=1C=CC=CC=1)OC1CN(C(=O)NCC=2C=CC=CC=2)C1 AYFRSZYMSBZIOY-UHFFFAOYSA-N 0.000 claims 1
- BAMHKCNSETUOBO-UHFFFAOYSA-N n-butan-2-yl-3-[(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)CC)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(Cl)C=C1 BAMHKCNSETUOBO-UHFFFAOYSA-N 0.000 claims 1
- CKUZPZFYFGZOSU-UHFFFAOYSA-N n-butan-2-yl-3-[(4-chlorophenyl)-[4-fluoro-2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)CC)CC1OC(C=1C(=CC(F)=CC=1)C(F)(F)F)C1=CC=C(Cl)C=C1 CKUZPZFYFGZOSU-UHFFFAOYSA-N 0.000 claims 1
- OGDZECLEZAVEGM-UHFFFAOYSA-N n-butan-2-yl-3-[(4-fluorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)CC)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(F)C=C1 OGDZECLEZAVEGM-UHFFFAOYSA-N 0.000 claims 1
- PQQGOZKVEOKNQU-UHFFFAOYSA-N n-butan-2-yl-3-[(4-methylsulfanylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)CC)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(SC)C=C1 PQQGOZKVEOKNQU-UHFFFAOYSA-N 0.000 claims 1
- BMSHUEMPIVDLSO-UHFFFAOYSA-N n-butan-2-yl-3-[[4-(difluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)CC)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(OC(F)F)C=C1 BMSHUEMPIVDLSO-UHFFFAOYSA-N 0.000 claims 1
- SZTJHJQPGRWWOH-UHFFFAOYSA-N n-butan-2-yl-3-[[4-(trifluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)CC)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(OC(F)(F)F)C=C1 SZTJHJQPGRWWOH-UHFFFAOYSA-N 0.000 claims 1
- BHSWRGGHCFTVNO-UHFFFAOYSA-N n-butan-2-yl-3-[phenyl-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)CC)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=CC=C1 BHSWRGGHCFTVNO-UHFFFAOYSA-N 0.000 claims 1
- AMPJXPAFTWUKMF-UHFFFAOYSA-N n-butyl-3-[(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NCCCC)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(Cl)C=C1 AMPJXPAFTWUKMF-UHFFFAOYSA-N 0.000 claims 1
- MPZMPPJJGNTVHR-UHFFFAOYSA-N n-cyclohexyl-3-[(4-fluorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC2CCCCC2)C1 MPZMPPJJGNTVHR-UHFFFAOYSA-N 0.000 claims 1
- UJOARMFZGDVVQP-UHFFFAOYSA-N n-cyclohexyl-3-[(4-methylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC2CCCCC2)C1 UJOARMFZGDVVQP-UHFFFAOYSA-N 0.000 claims 1
- ORJHHJOWGFPRHF-UHFFFAOYSA-N n-cyclohexyl-3-[(4-methylsulfanylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(SC)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC2CCCCC2)C1 ORJHHJOWGFPRHF-UHFFFAOYSA-N 0.000 claims 1
- DRNWAWJUXFFRSU-UHFFFAOYSA-N n-cyclohexyl-3-[[4-(difluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC2CCCCC2)C1 DRNWAWJUXFFRSU-UHFFFAOYSA-N 0.000 claims 1
- AHAYYOYPIVITNU-UHFFFAOYSA-N n-cyclohexyl-3-[phenyl-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C(C=1C=CC=CC=1)OC1CN(C(=O)NC2CCCCC2)C1 AHAYYOYPIVITNU-UHFFFAOYSA-N 0.000 claims 1
- NAQXOHUKTAFNDO-UHFFFAOYSA-N n-tert-butyl-3-[(4-chlorophenyl)-(2,4-dichlorophenyl)methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(Cl)C=C1 NAQXOHUKTAFNDO-UHFFFAOYSA-N 0.000 claims 1
- QLFCAMOXLZVIQX-UHFFFAOYSA-N n-tert-butyl-3-[(4-chlorophenyl)-[4-fluoro-2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC(F)=CC=1)C(F)(F)F)C1=CC=C(Cl)C=C1 QLFCAMOXLZVIQX-UHFFFAOYSA-N 0.000 claims 1
- MBCVORKWWTUQEI-UHFFFAOYSA-N n-tert-butyl-3-[(4-fluorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(F)C=C1 MBCVORKWWTUQEI-UHFFFAOYSA-N 0.000 claims 1
- IKANRRQTBDVMDU-UHFFFAOYSA-N n-tert-butyl-3-[(4-methoxyphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC(C)(C)C)C1 IKANRRQTBDVMDU-UHFFFAOYSA-N 0.000 claims 1
- NCZIGNURHCMRNY-UHFFFAOYSA-N n-tert-butyl-3-[(4-methylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC(C)(C)C)C1 NCZIGNURHCMRNY-UHFFFAOYSA-N 0.000 claims 1
- XMOQEKAEOOOHFV-UHFFFAOYSA-N n-tert-butyl-3-[(4-methylsulfanylphenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1=CC(SC)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NC(C)(C)C)C1 XMOQEKAEOOOHFV-UHFFFAOYSA-N 0.000 claims 1
- OFSKFPDEPXQBGO-UHFFFAOYSA-N n-tert-butyl-3-[[2-fluoro-4-(piperidine-1-carbonyl)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(C(=O)N2CCCCC2)C=C1F OFSKFPDEPXQBGO-UHFFFAOYSA-N 0.000 claims 1
- JTUXDFJRCBYXNX-UHFFFAOYSA-N n-tert-butyl-3-[[4-(difluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(OC(F)F)C=C1 JTUXDFJRCBYXNX-UHFFFAOYSA-N 0.000 claims 1
- DCBWYROPEMAPBJ-UHFFFAOYSA-N n-tert-butyl-3-[[4-(trifluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=C(OC(F)(F)F)C=C1 DCBWYROPEMAPBJ-UHFFFAOYSA-N 0.000 claims 1
- NMVHPPLPCPNGLX-UHFFFAOYSA-N n-tert-butyl-3-[phenyl-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)(C)C)CC1OC(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=CC=C1 NMVHPPLPCPNGLX-UHFFFAOYSA-N 0.000 claims 1
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- 230000007823 neuropathy Effects 0.000 claims 1
- 125000005593 norbornanyl group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229940127240 opiate Drugs 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000000391 smoking effect Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 *C(*)OC(C1)CN1C(N*)=O Chemical compound *C(*)OC(C1)CN1C(N*)=O 0.000 description 1
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Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004233644A1 (en) * | 2003-05-01 | 2004-11-11 | Vernalis Research Limited | The use of azetidinecarboxamide derivatives in therapy |
| CN1802351A (zh) | 2003-06-11 | 2006-07-12 | 麦克公司 | 被取代的3－烷基和3－链烯基氮杂环丁烷衍生物 |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| CA2613678A1 (en) | 2005-06-02 | 2006-12-07 | Glenmark Pharmaceuticals S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| US7906652B2 (en) | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| US20090264470A1 (en) * | 2006-02-21 | 2009-10-22 | Bennett Teresa A | CB1 Antagonists and Inverse Agonists |
| EP2061767B1 (de) | 2006-08-08 | 2014-12-17 | Sanofi | Arylaminoaryl-alkyl-substituierte Imidazolidin-2,4-dione, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und ihre Verwendung |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| FR2925051B1 (fr) * | 2007-12-18 | 2010-05-21 | Sanofi Aventis | Derives d'azetidines,leur preparation et leur application en therapeutique |
| EP2234966B1 (fr) * | 2007-12-18 | 2013-09-11 | Sanofi | Derives d'azetidines, leur preparation et leur application en therapeutique |
| PT2009157006W (pt) * | 2008-06-26 | 2012-10-17 | Micro Labs Ltd | Processo de preparação de ebastina |
| UY31968A (es) | 2008-07-09 | 2010-01-29 | Sanofi Aventis | Nuevos derivados heterocíclicos, sus procesos para su preparación, y sus usos terapéuticos |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| US8329914B2 (en) | 2008-10-31 | 2012-12-11 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| KR20120060207A (ko) | 2009-08-26 | 2012-06-11 | 사노피 | 신규한 결정성 헤테로방향족 플루오로글리코시드 수화물, 이들 화합물을 포함하는 약제 및 이들의 용도 |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| SG192941A1 (en) | 2011-02-25 | 2013-09-30 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| RU2015106909A (ru) | 2012-08-02 | 2016-09-27 | Мерк Шарп И Доум Корп. | Антидиабетические трициклические соединения |
| KR20150118158A (ko) | 2013-02-22 | 2015-10-21 | 머크 샤프 앤드 돔 코포레이션 | 항당뇨병 비시클릭 화합물 |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| US10077446B2 (en) | 2013-06-25 | 2018-09-18 | The United States Of America, As Represented By The Secretary, Dept. Of Health And Human Services | Glucan-encapsulated siRNA for treating type 2 diabetes mellitus |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| CN105218474B (zh) * | 2015-10-22 | 2017-12-05 | 山东国邦药业股份有限公司 | (4r,5r)‑2‑二氯甲基‑4,5‑二氢‑5‑(4‑甲砜基苯基)‑4‑恶唑甲醇的合成方法 |
| CN109689045A (zh) | 2016-05-04 | 2019-04-26 | 因美制药公司 | 大麻素的局部制剂在治疗大疱性表皮松解症和相关结缔组织病症中的用途 |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| US12357604B2 (en) | 2017-09-22 | 2025-07-15 | Inmed Pharmaceuticals Inc. | Topical formulations of cannabinoids and use thereof in the treatment of pain |
| WO2019134985A1 (en) | 2018-01-08 | 2019-07-11 | F. Hoffmann-La Roche Ag | Octahydropyrido[1,2-alpha]pyrazines as magl inhibitors |
| EP3669876A1 (en) * | 2018-12-18 | 2020-06-24 | Aelis Farma | 3béta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disorders |
| CA3190277A1 (en) | 2020-09-03 | 2022-03-10 | Joerg Benz | Heterocyclic compounds |
| US11141404B1 (en) * | 2020-11-18 | 2021-10-12 | Anebulo Pharmaceuticals, Inc. | Formulations and methods for treating acute cannabinoid overdose |
| AU2022362107A1 (en) * | 2021-10-11 | 2024-05-02 | Anebulo Pharmaceuticals, Inc. | Crystalline forms of a cannabinoid receptor type 1 (cb1) modulator and methods of use and preparation thereof |
| AU2023351188A1 (en) * | 2022-09-26 | 2025-04-17 | Anebulo Pharmaceuticals, Inc. | Treatment of acute cannabinoid overdose |
| WO2025090133A1 (en) | 2023-10-23 | 2025-05-01 | Inmed Pharmaceuticals Inc. | Compositions and methods for use of cannabinol compounds in neuroprotection |
| WO2025090587A1 (en) | 2023-10-23 | 2025-05-01 | Inmed Pharmaceuticals Inc. | Cannabinoids compounds and their use in the treatment of neuronal disorders |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4261990A (en) * | 1979-03-09 | 1981-04-14 | Ciba-Geigy Corporation | N-alkyleneiminoalkyl-dicarboximides as antiallergics and antiasthmatics |
| JPH03264562A (ja) * | 1989-05-22 | 1991-11-25 | Hokuriku Seiyaku Co Ltd | ピペリジン誘導体 |
| JP3194355B2 (ja) * | 1996-10-24 | 2001-07-30 | 宇部興産株式会社 | ピペリジン化合物及びその製法 |
| WO1999037612A1 (en) * | 1998-01-23 | 1999-07-29 | Vernalis Research Limited | Azetidinecarboxamide derivatives for treating cns disorders |
| GB9917386D0 (en) * | 1999-07-23 | 1999-09-22 | Cerebrus Ltd | Chemical compounds-II |
| US6566356B2 (en) * | 2000-03-03 | 2003-05-20 | Aventis Pharma S.A. | Pharmaceutical compositions containing 3-aminoazetidine derivatives, novel derivatives and their preparation |
| AU2004233644A1 (en) * | 2003-05-01 | 2004-11-11 | Vernalis Research Limited | The use of azetidinecarboxamide derivatives in therapy |
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- 2004-04-29 DE DE602004024880T patent/DE602004024880D1/de not_active Expired - Fee Related
- 2004-04-29 AT AT04730296T patent/ATE453620T1/de not_active IP Right Cessation
- 2004-04-29 US US10/552,575 patent/US7504522B2/en not_active Expired - Fee Related
- 2004-04-29 KR KR1020057020649A patent/KR20060010770A/ko not_active Ceased
- 2004-04-29 WO PCT/GB2004/001831 patent/WO2004096763A1/en not_active Ceased
- 2004-04-29 CN CNA2004800115989A patent/CN1802350A/zh active Pending
- 2004-04-29 BR BRPI0409938-9A patent/BRPI0409938A/pt not_active IP Right Cessation
- 2004-04-29 EP EP04730296A patent/EP1620395B1/en not_active Expired - Lifetime
- 2004-04-29 MX MXPA05011670A patent/MXPA05011670A/es active IP Right Grant
- 2004-04-29 NZ NZ543016A patent/NZ543016A/en unknown
- 2004-04-29 EA EA200501585A patent/EA010583B1/ru not_active IP Right Cessation
- 2004-04-29 CA CA002524251A patent/CA2524251A1/en not_active Abandoned
- 2004-04-29 JP JP2006506198A patent/JP2006525298A/ja active Pending
-
2005
- 2005-10-31 ZA ZA200508831A patent/ZA200508831B/en unknown
- 2005-11-30 NO NO20055654A patent/NO20055654L/no not_active Application Discontinuation
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