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
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| 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 |
| AU2007222069A1 (en) * | 2006-02-21 | 2007-09-13 | Ampla Pharmaceuticals Inc. | CB1 antagonists and inverse agonists |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CA2709863A1 (fr) * | 2007-12-18 | 2009-09-03 | Sanofi-Aventis | Derives d'azetidines, leur preparation et leur application en therapeutique |
| FR2925051B1 (fr) * | 2007-12-18 | 2010-05-21 | Sanofi Aventis | Derives d'azetidines,leur preparation et leur application en therapeutique |
| WO2009157006A1 (en) * | 2008-06-26 | 2009-12-30 | Micro Labs Limited | Process of preparing ebastine |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP5557845B2 (ja) | 2008-10-31 | 2014-07-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病用剤として有用な新規環状ベンゾイミダゾール誘導体 |
| 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 |
| MX2012001729A (es) | 2009-08-26 | 2012-06-13 | Sanofi Sa | Nuevos hidratos cristalinos de fluoroglicosido heteroaromatico, productos farmaceuticos que comprenden estos compuestos, y su empleo. |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| BR112013021236B1 (pt) | 2011-02-25 | 2021-05-25 | Merck Sharp & Dohme Corp | composto derivado de benzimidazol, e, composição |
| 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 |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte 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 |
| US9527875B2 (en) | 2012-08-02 | 2016-12-27 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| RU2015140066A (ru) | 2013-02-22 | 2017-03-30 | Мерк Шарп И Доум Корп. | Противодиабетические бициклические соединения |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| EP3013958B1 (en) * | 2013-06-25 | 2019-12-25 | The United States of America, as represented by the Secretary, Department 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 |
| AU2017260706B2 (en) | 2016-05-04 | 2023-05-11 | Inmed Pharmaceuticals Inc. | Use of topical formulations of cannabinoids in the treatment of epidermolysis bullosa and related connective tissue disorders |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| EP3684353A4 (en) | 2017-09-22 | 2021-06-23 | Inmed Pharmaceuticals Inc. | TOPICAL FORMULATIONS OF CANNABINOIDS AND THEIR USES FOR PAIN TREATMENT |
| 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 |
| MX2023002224A (es) | 2020-09-03 | 2023-03-15 | Hoffmann La Roche | Compuestos heterociclicos. |
| 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 |
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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 |
| DE69911373T2 (de) * | 1998-01-23 | 2004-07-01 | Vernalis Research Ltd., Winnersh | Azetidincarboxamidderivate zur behandlung von zns-erkrankungen |
| 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 |
| NZ543322A (en) * | 2003-05-01 | 2009-03-31 | Vernalis Res Ltd | The use of azetidinecarboxamide derivates in therapy |
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2004
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- 2005-11-30 NO NO20055654A patent/NO20055654L/no not_active Application Discontinuation