RU2006100298A - Замещенные производные 3-алкил-и 3-алкенилазетидинов - Google Patents
Замещенные производные 3-алкил-и 3-алкенилазетидинов Download PDFInfo
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- RU2006100298A RU2006100298A RU2006100298/04A RU2006100298A RU2006100298A RU 2006100298 A RU2006100298 A RU 2006100298A RU 2006100298/04 A RU2006100298/04 A RU 2006100298/04A RU 2006100298 A RU2006100298 A RU 2006100298A RU 2006100298 A RU2006100298 A RU 2006100298A
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- RU
- Russia
- Prior art keywords
- methyl
- azetidin
- chlorophenyl
- difluorophenyl
- methylpropyl
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims 38
- -1 (2) pyridyl Chemical group 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 27
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 14
- OWDWPEKPZKOICB-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3-chlorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=CC(Cl)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 OWDWPEKPZKOICB-UHFFFAOYSA-N 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 11
- 208000008589 Obesity Diseases 0.000 claims 10
- 235000020824 obesity Nutrition 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 235000014632 disordered eating Nutrition 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 230000037406 food intake Effects 0.000 claims 8
- 235000012631 food intake Nutrition 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 208000030814 Eating disease Diseases 0.000 claims 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 7
- 150000001721 carbon Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 230000001404 mediated effect Effects 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 102000005962 receptors Human genes 0.000 claims 6
- 108020003175 receptors Proteins 0.000 claims 6
- NTAXGDGMWOECQL-FTJBHMTQSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-hydroxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 NTAXGDGMWOECQL-FTJBHMTQSA-N 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- JVUQFIFRWPWKGU-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JVUQFIFRWPWKGU-UHFFFAOYSA-N 0.000 claims 4
- OKFSGWKWCZLYOD-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(4-fluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=C(F)C=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 OKFSGWKWCZLYOD-UHFFFAOYSA-N 0.000 claims 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- UHFLYZUYHXDFBS-UHFFFAOYSA-N 1-[1-[(4-chlorophenyl)-(4-methylsulfonylphenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(=CC=1)S(C)(=O)=O)C1=CC=C(Cl)C=C1 UHFLYZUYHXDFBS-UHFFFAOYSA-N 0.000 claims 3
- BGIHCOSDPGRSPA-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 BGIHCOSDPGRSPA-UHFFFAOYSA-N 0.000 claims 3
- ATIDGLSLFKOOCE-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)propan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 ATIDGLSLFKOOCE-UHFFFAOYSA-N 0.000 claims 3
- HJVCJGUTCZTKBU-UHFFFAOYSA-N 3-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-3-(3,5-difluorophenyl)-2,2-dimethylpropanenitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(C#N)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 HJVCJGUTCZTKBU-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- MTAIRXFXLWRCRN-UHFFFAOYSA-N 1-[1-[(2-chlorophenyl)-(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C(=CC=CC=1)Cl)C1=CC=C(Cl)C=C1 MTAIRXFXLWRCRN-UHFFFAOYSA-N 0.000 claims 2
- ZEAAYFFEZQJVIG-UHFFFAOYSA-N 1-[1-[(2-chlorophenyl)-(4-fluorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C(=CC=CC=1)Cl)C1=CC=C(F)C=C1 ZEAAYFFEZQJVIG-UHFFFAOYSA-N 0.000 claims 2
- YAHCQOGXNFPDMT-UHFFFAOYSA-N 1-[1-[(3-chlorophenyl)-(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=C(Cl)C=CC=1)C1=CC=C(Cl)C=C1 YAHCQOGXNFPDMT-UHFFFAOYSA-N 0.000 claims 2
- NYGZMGGANWYLOM-UHFFFAOYSA-N 1-[1-[(4-chlorophenyl)-(4-fluorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(F)C=C1 NYGZMGGANWYLOM-UHFFFAOYSA-N 0.000 claims 2
- GKPPCRLZZIELCK-UHFFFAOYSA-N 1-[1-[(4-chlorophenyl)-phenylmethyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 GKPPCRLZZIELCK-UHFFFAOYSA-N 0.000 claims 2
- NKFYPGJRGHKNCW-UHFFFAOYSA-N 1-[1-[1-(4-chlorophenyl)pentyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)N(C1)CC1C(C(C)(C)O)C1=CC(F)=CC(F)=C1 NKFYPGJRGHKNCW-UHFFFAOYSA-N 0.000 claims 2
- XARIKKVJVOWHFL-UHFFFAOYSA-N 1-[1-[1-(4-chlorophenyl)pentyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)N(C1)CC1=C(C(C)(C)O)C1=CC(F)=CC(F)=C1 XARIKKVJVOWHFL-UHFFFAOYSA-N 0.000 claims 2
- XWTDLGLHFYWLAV-UHFFFAOYSA-N 3-[(4-chlorophenyl)-[3-[1-(3,5-difluorophenyl)-2,2-dimethylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(C)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(Cl)C=C1 XWTDLGLHFYWLAV-UHFFFAOYSA-N 0.000 claims 2
- CFSBYHISKWJSMI-UHFFFAOYSA-N 3-[(4-chlorophenyl)-[3-[2-fluoro-1-[3-fluoro-5-(1,2,4-triazol-4-yl)phenyl]-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(N2C=NN=C2)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(Cl)C=C1 CFSBYHISKWJSMI-UHFFFAOYSA-N 0.000 claims 2
- NTAXGDGMWOECQL-CLJLJLNGSA-N 3-[(r)-(4-chlorophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-hydroxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 NTAXGDGMWOECQL-CLJLJLNGSA-N 0.000 claims 2
- NTAXGDGMWOECQL-UIOOFZCWSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1r)-1-(3,5-difluorophenyl)-2-hydroxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 NTAXGDGMWOECQL-UIOOFZCWSA-N 0.000 claims 2
- SIGYZOKUSLPHLI-FTJBHMTQSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 SIGYZOKUSLPHLI-FTJBHMTQSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010010774 Constipation Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 208000010235 Food Addiction Diseases 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- GMFGENLXAWETEK-UHFFFAOYSA-N [1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)propan-2-yl] n-propan-2-ylcarbamate Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)OC(=O)NC(C)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 GMFGENLXAWETEK-UHFFFAOYSA-N 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
- 208000014797 chronic intestinal pseudoobstruction Diseases 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 230000001272 neurogenic effect Effects 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- BBJFJBNEEAFYJM-DEOSSOPVSA-N (1r)-1-(1-benzhydrylazetidin-3-yl)-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C1C([C@@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BBJFJBNEEAFYJM-DEOSSOPVSA-N 0.000 claims 1
- GKPPCRLZZIELCK-DQEYMECFSA-N (1r)-1-[1-[(s)-(4-chlorophenyl)-phenylmethyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C1([C@H](N2CC(C2)[C@@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(Cl)=CC=2)=CC=CC=C1 GKPPCRLZZIELCK-DQEYMECFSA-N 0.000 claims 1
- GKPPCRLZZIELCK-JWQCQUIFSA-N (1s)-1-[1-[(r)-(4-chlorophenyl)-phenylmethyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(Cl)=CC=2)=CC=CC=C1 GKPPCRLZZIELCK-JWQCQUIFSA-N 0.000 claims 1
- BBJFJBNEEAFYJM-UHFFFAOYSA-N 1-(1-benzhydrylazetidin-3-yl)-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BBJFJBNEEAFYJM-UHFFFAOYSA-N 0.000 claims 1
- NGTREPAVXJWHRY-UHFFFAOYSA-N 1-(1-methylimidazol-4-yl)propan-2-ol Chemical compound CC(O)CC1=CN(C)C=N1 NGTREPAVXJWHRY-UHFFFAOYSA-N 0.000 claims 1
- WDHVRBCSVCQYHO-UHFFFAOYSA-N 1-[(4-chlorophenyl)-(3-methylsulfonylphenyl)methyl]-3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)S(C)(=O)=O)C1=CC=C(Cl)C=C1 WDHVRBCSVCQYHO-UHFFFAOYSA-N 0.000 claims 1
- VXSZSBJPNRYPJD-UHFFFAOYSA-N 1-[1-[(4-chlorophenyl)-phenylmethyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 VXSZSBJPNRYPJD-UHFFFAOYSA-N 0.000 claims 1
- WRQMZGXBEMQPBW-UHFFFAOYSA-N 1-[1-[1,1-bis(4-chlorophenyl)ethyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C)(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 WRQMZGXBEMQPBW-UHFFFAOYSA-N 0.000 claims 1
- CRTLWCCTKGDSDV-UHFFFAOYSA-N 1-[1-[1-(4-chlorophenyl)ethyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=C(Cl)C=CC=1C(C)N(C1)CC1=C(C(C)(C)O)C1=CC(F)=CC(F)=C1 CRTLWCCTKGDSDV-UHFFFAOYSA-N 0.000 claims 1
- XGCDPNFYJGFQLI-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)-2,2-dimethylpropan-1-ol Chemical compound C=1C(F)=CC(F)=CC=1C(O)(C(C)(C)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 XGCDPNFYJGFQLI-UHFFFAOYSA-N 0.000 claims 1
- QLHXUURSZHULTA-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3,5-difluorophenyl)propan-2-one Chemical compound C=1C(F)=CC(F)=CC=1C(C(=O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 QLHXUURSZHULTA-UHFFFAOYSA-N 0.000 claims 1
- NMJOVINQOXNVRA-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3-chlorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=CC(Cl)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 NMJOVINQOXNVRA-UHFFFAOYSA-N 0.000 claims 1
- ZHRXBRLKJALMRK-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3-fluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 ZHRXBRLKJALMRK-UHFFFAOYSA-N 0.000 claims 1
- PUYRJPWWRFWFHX-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-2-methyl-1-(4-methylsulfonylphenyl)propan-2-ol Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 PUYRJPWWRFWFHX-UHFFFAOYSA-N 0.000 claims 1
- LKCUWXNVISGTQI-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-2-methyl-1-pyridin-3-ylpropan-2-ol Chemical compound C=1C=CN=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LKCUWXNVISGTQI-UHFFFAOYSA-N 0.000 claims 1
- QIJVLWPHWMVSTN-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)-2-methylpropan-2-amine Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(N)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 QIJVLWPHWMVSTN-UHFFFAOYSA-N 0.000 claims 1
- JRWFXJMIFMVHEY-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3-fluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=CC(F)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JRWFXJMIFMVHEY-UHFFFAOYSA-N 0.000 claims 1
- JWBGEFWLKHNGHR-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-2-methyl-1-[3-(trifluoromethyl)phenyl]propan-2-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JWBGEFWLKHNGHR-UHFFFAOYSA-N 0.000 claims 1
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- BQJDSAYFESAZKO-XMMPIXPASA-N 1-[bis(4-chlorophenyl)methyl]-3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidine Chemical compound C1C([C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 BQJDSAYFESAZKO-XMMPIXPASA-N 0.000 claims 1
- GINXZQMJLLIVAT-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]-3-[1-(3,5-difluorophenyl)-1-fluoro-2,2-dimethylpropyl]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(F)(C(C)(C)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 GINXZQMJLLIVAT-UHFFFAOYSA-N 0.000 claims 1
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- GJXINXYTURSTGR-XMMPIXPASA-N 1-benzhydryl-3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidine Chemical compound C1C([C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GJXINXYTURSTGR-XMMPIXPASA-N 0.000 claims 1
- GJXINXYTURSTGR-UHFFFAOYSA-N 1-benzhydryl-3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GJXINXYTURSTGR-UHFFFAOYSA-N 0.000 claims 1
- QTVMNDFLTGOAED-UHFFFAOYSA-N 1-benzhydryl-3-[1-(3,5-difluorophenyl)-2-methylprop-1-enyl]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(=C(C)C)C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 QTVMNDFLTGOAED-UHFFFAOYSA-N 0.000 claims 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
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- ZPRDZRXMXWWPMZ-RRPNLBNLSA-N 3-[(1r)-1-[1-[(r)-(4-chlorophenyl)-(3-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 ZPRDZRXMXWWPMZ-RRPNLBNLSA-N 0.000 claims 1
- PNDHRQSCKWHPNP-SVBPBHIXSA-N 3-[(1r)-1-[1-[(s)-(3-bromophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(Br)C=CC=2)=CC=C(C#N)C=C1 PNDHRQSCKWHPNP-SVBPBHIXSA-N 0.000 claims 1
- LYSLISZPAZFYMF-NSOVKSMOSA-N 3-[(1r)-1-[1-[(s)-(3-cyanophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 LYSLISZPAZFYMF-NSOVKSMOSA-N 0.000 claims 1
- ZPRDZRXMXWWPMZ-SVBPBHIXSA-N 3-[(1r)-1-[1-[(s)-(4-chlorophenyl)-(3-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 ZPRDZRXMXWWPMZ-SVBPBHIXSA-N 0.000 claims 1
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- PNDHRQSCKWHPNP-KAYWLYCHSA-N 3-[(1s)-1-[1-[(r)-(3-bromophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(Br)C=CC=2)=CC=C(C#N)C=C1 PNDHRQSCKWHPNP-KAYWLYCHSA-N 0.000 claims 1
- LYSLISZPAZFYMF-VSGBNLITSA-N 3-[(1s)-1-[1-[(r)-(3-cyanophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 LYSLISZPAZFYMF-VSGBNLITSA-N 0.000 claims 1
- ZPRDZRXMXWWPMZ-KAYWLYCHSA-N 3-[(1s)-1-[1-[(r)-(4-chlorophenyl)-(3-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 ZPRDZRXMXWWPMZ-KAYWLYCHSA-N 0.000 claims 1
- PNDHRQSCKWHPNP-SXOMAYOGSA-N 3-[(1s)-1-[1-[(s)-(3-bromophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(Br)C=CC=2)=CC=C(C#N)C=C1 PNDHRQSCKWHPNP-SXOMAYOGSA-N 0.000 claims 1
- LYSLISZPAZFYMF-IZLXSDGUSA-N 3-[(1s)-1-[1-[(s)-(3-cyanophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 LYSLISZPAZFYMF-IZLXSDGUSA-N 0.000 claims 1
- ZPRDZRXMXWWPMZ-SXOMAYOGSA-N 3-[(1s)-1-[1-[(s)-(4-chlorophenyl)-(3-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 ZPRDZRXMXWWPMZ-SXOMAYOGSA-N 0.000 claims 1
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- YBNGGOLHSADUAS-UHFFFAOYSA-N 3-[(4-chlorophenyl)-[3-[1-(3,5-difluorophenyl)-2,2-dimethylpropylidene]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(C)C)=C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(Cl)C=C1 YBNGGOLHSADUAS-UHFFFAOYSA-N 0.000 claims 1
- NTAXGDGMWOECQL-UHFFFAOYSA-N 3-[(4-chlorophenyl)-[3-[1-(3,5-difluorophenyl)-2-hydroxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(Cl)C=C1 NTAXGDGMWOECQL-UHFFFAOYSA-N 0.000 claims 1
- OQBPYWPOWHBEDF-UHFFFAOYSA-N 3-[(4-chlorophenyl)-[3-[1-(3,5-difluorophenyl)-2-methylprop-1-enyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(=C(C)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(Cl)C=C1 OQBPYWPOWHBEDF-UHFFFAOYSA-N 0.000 claims 1
- QHSQRHALZNSPIZ-UHFFFAOYSA-N 3-[(4-cyanophenyl)-[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(C#N)C=C1 QHSQRHALZNSPIZ-UHFFFAOYSA-N 0.000 claims 1
- OLBHHMPXXWOJMC-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)-[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(Cl)N=C1 OLBHHMPXXWOJMC-UHFFFAOYSA-N 0.000 claims 1
- KQSHLPYMGZRTAN-CLJLJLNGSA-N 3-[(r)-(4-chloro-3-iodophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(I)C(Cl)=CC=2)=CC=CC(C#N)=C1 KQSHLPYMGZRTAN-CLJLJLNGSA-N 0.000 claims 1
- CAUZGGWERABMQG-CLJLJLNGSA-N 3-[(r)-(4-chloro-3-iodophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-hydroxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=C(I)C(Cl)=CC=2)=CC=CC(C#N)=C1 CAUZGGWERABMQG-CLJLJLNGSA-N 0.000 claims 1
- NTAXGDGMWOECQL-IZZNHLLZSA-N 3-[(r)-(4-chlorophenyl)-[3-[(1r)-1-(3,5-difluorophenyl)-2-hydroxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 NTAXGDGMWOECQL-IZZNHLLZSA-N 0.000 claims 1
- QXECPSSAILBAJK-URLMMPGGSA-N 3-[(r)-(4-chlorophenyl)-[3-[(1r)-2-fluoro-1-(3-fluoro-5-imidazol-1-ylphenyl)-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(C=C(F)C=2)N2C=NC=C2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 QXECPSSAILBAJK-URLMMPGGSA-N 0.000 claims 1
- CFSBYHISKWJSMI-WUFINQPMSA-N 3-[(r)-(4-chlorophenyl)-[3-[(1r)-2-fluoro-1-[3-fluoro-5-(1,2,4-triazol-4-yl)phenyl]-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(C=C(F)C=2)N2C=NN=C2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 CFSBYHISKWJSMI-WUFINQPMSA-N 0.000 claims 1
- QHSQRHALZNSPIZ-RRPNLBNLSA-N 3-[(r)-(4-cyanophenyl)-[3-[(1r)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 QHSQRHALZNSPIZ-RRPNLBNLSA-N 0.000 claims 1
- QHSQRHALZNSPIZ-KAYWLYCHSA-N 3-[(r)-(4-cyanophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 QHSQRHALZNSPIZ-KAYWLYCHSA-N 0.000 claims 1
- BAMSWPNFBCDNFE-KAYWLYCHSA-N 3-[(r)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]-(3-methylsulfonylphenyl)methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)S(C)(=O)=O)=CC=CC(C#N)=C1 BAMSWPNFBCDNFE-KAYWLYCHSA-N 0.000 claims 1
- SBSDAUPZKGDHQH-CLJLJLNGSA-N 3-[(r)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]-[4-(trifluoromethyl)phenyl]methyl]benzonitrile Chemical compound C1([C@@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(C(F)(F)F)C=C1 SBSDAUPZKGDHQH-CLJLJLNGSA-N 0.000 claims 1
- CAUZGGWERABMQG-FTJBHMTQSA-N 3-[(s)-(4-chloro-3-iodophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-hydroxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(O)C)C=2C=C(F)C=C(F)C=2)C=2C=C(I)C(Cl)=CC=2)=CC=CC(C#N)=C1 CAUZGGWERABMQG-FTJBHMTQSA-N 0.000 claims 1
- AVALOMWDXGWDHD-SXOMAYOGSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-methoxy-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(C)OC)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 AVALOMWDXGWDHD-SXOMAYOGSA-N 0.000 claims 1
- DAGYRJXBSXAZKP-SXOMAYOGSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 DAGYRJXBSXAZKP-SXOMAYOGSA-N 0.000 claims 1
- PONLDEGOMWQMSA-IZLXSDGUSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-1-(3-ethylsulfanyl-5-fluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound CCSC1=CC(F)=CC([C@H](C2CN(C2)[C@@H](C=2C=CC(Cl)=CC=2)C=2C=C(C=CC=2)C#N)C(C)(C)F)=C1 PONLDEGOMWQMSA-IZLXSDGUSA-N 0.000 claims 1
- QXECPSSAILBAJK-WDYNHAJCSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-2-fluoro-1-(3-fluoro-5-imidazol-1-ylphenyl)-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)N2C=NC=C2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 QXECPSSAILBAJK-WDYNHAJCSA-N 0.000 claims 1
- OOPYMCKIALOYEP-IZLXSDGUSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-2-fluoro-1-[3-fluoro-5-(1,2,4-triazol-1-yl)phenyl]-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)N2N=CN=C2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 OOPYMCKIALOYEP-IZLXSDGUSA-N 0.000 claims 1
- QHSQRHALZNSPIZ-SVBPBHIXSA-N 3-[(s)-(4-cyanophenyl)-[3-[(1r)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 QHSQRHALZNSPIZ-SVBPBHIXSA-N 0.000 claims 1
- QHSQRHALZNSPIZ-SXOMAYOGSA-N 3-[(s)-(4-cyanophenyl)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 QHSQRHALZNSPIZ-SXOMAYOGSA-N 0.000 claims 1
- BAMSWPNFBCDNFE-SXOMAYOGSA-N 3-[(s)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]-(3-methylsulfonylphenyl)methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)S(C)(=O)=O)=CC=CC(C#N)=C1 BAMSWPNFBCDNFE-SXOMAYOGSA-N 0.000 claims 1
- SBSDAUPZKGDHQH-FTJBHMTQSA-N 3-[(s)-[3-[(1s)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]-[4-(trifluoromethyl)phenyl]methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(F)C=C(F)C=2)C=2C=C(C=CC=2)C#N)=CC=C(C(F)(F)F)C=C1 SBSDAUPZKGDHQH-FTJBHMTQSA-N 0.000 claims 1
- PHOVKOIFKLFBMB-WDYNHAJCSA-N 3-[(s)-[3-[(1s)-1-[3-(azetidin-1-yl)-5-fluorophenyl]-2-fluoro-2-methylpropyl]azetidin-1-yl]-(4-chlorophenyl)methyl]benzonitrile Chemical compound C1([C@H](N2CC(C2)[C@H](C(C)(F)C)C=2C=C(C=C(F)C=2)N2CCC2)C=2C=C(C=CC=2)C#N)=CC=C(Cl)C=C1 PHOVKOIFKLFBMB-WDYNHAJCSA-N 0.000 claims 1
- YPIOMNBXBMTSEN-UHFFFAOYSA-N 3-[1-(1-benzhydrylazetidin-3-yl)-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C=1C(F)=CC(C#N)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YPIOMNBXBMTSEN-UHFFFAOYSA-N 0.000 claims 1
- PNDHRQSCKWHPNP-UHFFFAOYSA-N 3-[1-[1-[(3-bromophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C=1C(F)=CC(C#N)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(Br)C=CC=1)C1=CC=C(C#N)C=C1 PNDHRQSCKWHPNP-UHFFFAOYSA-N 0.000 claims 1
- LYSLISZPAZFYMF-UHFFFAOYSA-N 3-[1-[1-[(3-cyanophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C=1C(F)=CC(C#N)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(C#N)C=C1 LYSLISZPAZFYMF-UHFFFAOYSA-N 0.000 claims 1
- ZPRDZRXMXWWPMZ-UHFFFAOYSA-N 3-[1-[1-[(4-chlorophenyl)-(3-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C=1C(F)=CC(C#N)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(Cl)C=C1 ZPRDZRXMXWWPMZ-UHFFFAOYSA-N 0.000 claims 1
- LYSLISZPAZFYMF-PLYLYKGUSA-N 3-[1-[1-[(r)-(3-cyanophenyl)-(4-cyanophenyl)methyl]azetidin-3-yl]-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C1([C@@H](N2CC(C2)C(C(C)(F)C)C=2C=C(C=C(F)C=2)C#N)C=2C=C(C=CC=2)C#N)=CC=C(C#N)C=C1 LYSLISZPAZFYMF-PLYLYKGUSA-N 0.000 claims 1
- MMHZUWHXBKQAKY-UHFFFAOYSA-N 3-[1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-2-hydroxy-2-methylpropyl]benzonitrile Chemical compound C=1C=CC(C#N)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 MMHZUWHXBKQAKY-UHFFFAOYSA-N 0.000 claims 1
- SIMTWPKHLQXANO-UHFFFAOYSA-N 3-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-3-(3,5-difluorophenyl)-2,2-dimethyl-n-propan-2-ylpropanamide Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(C)C(=O)NC(C)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 SIMTWPKHLQXANO-UHFFFAOYSA-N 0.000 claims 1
- JUGPFYHFHHYOOW-UHFFFAOYSA-N 3-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-3-(3,5-difluorophenyl)-2-methylpropanenitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C#N)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JUGPFYHFHHYOOW-UHFFFAOYSA-N 0.000 claims 1
- QHMPVHOOKZWETL-UHFFFAOYSA-N 3-[[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]-(4-fluorophenyl)methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(F)C=C1 QHMPVHOOKZWETL-UHFFFAOYSA-N 0.000 claims 1
- XXCKZUUPSRTUIZ-UHFFFAOYSA-N 3-[[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]-(4-methylphenyl)methyl]benzonitrile Chemical compound C1=CC(C)=CC=C1C(C=1C=C(C=CC=1)C#N)N1CC(C(C=2C=C(F)C=C(F)C=2)C(C)(C)F)C1 XXCKZUUPSRTUIZ-UHFFFAOYSA-N 0.000 claims 1
- SBSDAUPZKGDHQH-UHFFFAOYSA-N 3-[[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]-[4-(trifluoromethyl)phenyl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(C=CC=1)C#N)C1=CC=C(C(F)(F)F)C=C1 SBSDAUPZKGDHQH-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 1
- GYRYYHJVEMQHIT-UHFFFAOYSA-N 4-[(3-bromophenyl)-[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=C(Br)C=CC=1)C1=CC=C(C#N)C=C1 GYRYYHJVEMQHIT-UHFFFAOYSA-N 0.000 claims 1
- CKZAKMWDOZQZME-UHFFFAOYSA-N 4-[(4-chlorophenyl)-[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]-2-methylpyridine Chemical compound C1=NC(C)=CC(C(N2CC(C2)C(C=2C=C(F)C=C(F)C=2)C(C)(C)F)C=2C=CC(Cl)=CC=2)=C1 CKZAKMWDOZQZME-UHFFFAOYSA-N 0.000 claims 1
- STXHKUOSYUFBAB-UHFFFAOYSA-N 4-[3-[1-(1-benzhydrylazetidin-3-yl)-2-fluoro-2-methylpropyl]-5-fluorophenyl]-1,2,4-triazole Chemical compound C=1C(F)=CC(N2C=NN=C2)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 STXHKUOSYUFBAB-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- MGUZSGTUEPWHIX-UHFFFAOYSA-N 5-[(4-chlorophenyl)-[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]thiophene-3-carbonitrile Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC(C#N)=CS1 MGUZSGTUEPWHIX-UHFFFAOYSA-N 0.000 claims 1
- ZTHREXJRXDCCFH-UHFFFAOYSA-N 5-[1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-2-hydroxy-2-methylpropyl]pyridine-3-carbonitrile Chemical compound C=1N=CC(C#N)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 ZTHREXJRXDCCFH-UHFFFAOYSA-N 0.000 claims 1
- LHUFXJVQLYIJRS-UHFFFAOYSA-N 5-chloro-2-[(4-chlorophenyl)-[3-[1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl]methyl]pyridine Chemical compound C=1C(F)=CC(F)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1N=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LHUFXJVQLYIJRS-UHFFFAOYSA-N 0.000 claims 1
- OZMRPDXRDVXFFA-UHFFFAOYSA-N CC(CN(C)C(=O)O)C(=C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F Chemical compound CC(CN(C)C(=O)O)C(=C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F OZMRPDXRDVXFFA-UHFFFAOYSA-N 0.000 claims 1
- SDAKJAGQMDDQAP-UHFFFAOYSA-N CC(CN(C)C(=O)O)C(C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F Chemical compound CC(CN(C)C(=O)O)C(C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F SDAKJAGQMDDQAP-UHFFFAOYSA-N 0.000 claims 1
- QRMRPUSDXJKDGU-UHFFFAOYSA-N [1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)propan-2-yl] (4-nitrophenyl) carbonate Chemical compound C1N(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)CC1=C(C=1C=C(F)C=C(F)C=1)C(C)OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 QRMRPUSDXJKDGU-UHFFFAOYSA-N 0.000 claims 1
- LTTVSJQZENMTLY-UHFFFAOYSA-N [2-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-2-(3,5-difluorophenyl)ethyl] (4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OCC(C=1C=C(F)C=C(F)C=1)=C1CN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C1 LTTVSJQZENMTLY-UHFFFAOYSA-N 0.000 claims 1
- USBUUECPFQBXCM-UHFFFAOYSA-N [2-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-2-(3,5-difluorophenyl)ethyl] n-propan-2-ylcarbamate Chemical compound C=1C(F)=CC(F)=CC=1C(COC(=O)NC(C)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 USBUUECPFQBXCM-UHFFFAOYSA-N 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([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
- 208000030212 nutrition disease Diseases 0.000 claims 1
- 208000019180 nutritional disease Diseases 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
Classifications
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- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47785003P | 2003-06-11 | 2003-06-11 | |
| US60/477,850 | 2003-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2006100298A true RU2006100298A (ru) | 2006-05-10 |
Family
ID=33551769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006100298/04A RU2006100298A (ru) | 2003-06-11 | 2004-06-09 | Замещенные производные 3-алкил-и 3-алкенилазетидинов |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7485732B2 (https=) |
| EP (1) | EP1636181A1 (https=) |
| JP (3) | JP3939744B2 (https=) |
| KR (1) | KR20060019587A (https=) |
| CN (1) | CN1802351A (https=) |
| AU (1) | AU2004252109B2 (https=) |
| BR (1) | BRPI0411131A (https=) |
| CA (1) | CA2527933C (https=) |
| CO (1) | CO5650244A2 (https=) |
| EC (1) | ECSP056207A (https=) |
| IL (1) | IL172417A0 (https=) |
| IS (1) | IS8146A (https=) |
| MA (1) | MA27847A1 (https=) |
| MX (1) | MXPA05013583A (https=) |
| NO (1) | NO20060141L (https=) |
| NZ (1) | NZ543451A (https=) |
| RU (1) | RU2006100298A (https=) |
| UA (1) | UA83230C2 (https=) |
| WO (1) | WO2005000809A1 (https=) |
| ZA (1) | ZA200509019B (https=) |
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| EP1575901B1 (en) | 2002-12-19 | 2012-10-10 | Merck Sharp & Dohme Corp. | Substituted amides |
| 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 |
| EP1682494A4 (en) | 2003-10-30 | 2006-11-08 | Merck & Co Inc | ARALKYLAMINES AS MODULATORS OF CANNABINOID RECEPTORS |
| EP1879582A4 (en) * | 2005-05-02 | 2009-05-13 | Merck & Co Inc | COMBINATION OF A DIPEPTIDYLPEPTIDASE IV HEMMER AND A CANNABINOID CB1 RECEPTOR ANTAGONIST FOR THE TREATMENT OF DIABETES AND ADIPOSITAS |
| EP1940842B1 (en) | 2005-09-29 | 2012-05-30 | Merck Sharp & Dohme Corp. | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
| AR058199A1 (es) * | 2005-11-28 | 2008-01-23 | Merck & Co Inc | Derivados de 3- alquilazetidina sustituidos con heterociclos |
| US7906652B2 (en) | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| PE20071092A1 (es) * | 2005-12-08 | 2007-12-10 | Aventis Pharma Inc | Composicion farmaceutica que comprende un antagonista de cb1 y un agente antisicotico |
| CA2638800A1 (en) | 2006-02-22 | 2007-09-07 | Merck & Co., Inc. | Oxyntomodulin derivatives |
| 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 |
| US8173629B2 (en) | 2006-09-22 | 2012-05-08 | Merck Sharp & Dohme Corp. | Method of treatment using fatty acid synthesis inhibitors |
| WO2008118141A2 (en) * | 2006-10-17 | 2008-10-02 | Acadia Pharmaceuticals Inc. | Use of cannabinoid modulating compounds in combination with other therapeutic compounds for adjunctive therapy |
| US7999107B2 (en) | 2007-01-31 | 2011-08-16 | Merck Sharp & Dohme Corp. | Substituted pyrano[2,3-B]pyridine derivatives as cannabinoid-1 receptor modulators |
| JP5319518B2 (ja) | 2007-04-02 | 2013-10-16 | Msd株式会社 | インドールジオン誘導体 |
| EP2170065A4 (en) | 2007-06-20 | 2011-11-23 | Merck Sharp & Dohme | DIPHENYL SUBSTITUTED ALKANES |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| JP2011502119A (ja) * | 2007-10-24 | 2011-01-20 | メルク・シャープ・エンド・ドーム・コーポレイション | Cb−1アンタゴニスト/逆アゴニストの合成及び結晶体 |
| EP2095814A1 (de) * | 2008-02-26 | 2009-09-02 | Wolfgang J. Kox | Medikamentengestützter Nikotinentzug |
| UY31968A (es) | 2008-07-09 | 2010-01-29 | Sanofi Aventis | Nuevos derivados heterocíclicos, sus procesos para su preparación, y sus usos terapéuticos |
| JP2012504630A (ja) | 2008-10-03 | 2012-02-23 | シェーリング コーポレイション | グルカゴン受容体アンタゴニストとしてのスピロイミダゾロン誘導体 |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| MX2011004551A (es) | 2008-10-30 | 2011-05-25 | Merck Sharp & Dohme | Antagonistas del receptor de orexina de isonicotinamida. |
| 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 |
| WO2010144664A1 (en) | 2009-06-12 | 2010-12-16 | Schering Corporation | Thiophenes as glucagon receptor antagonists, compositions, and methods for their use |
| 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 |
| US8450350B2 (en) | 2010-05-05 | 2013-05-28 | Infinity Pharmaceuticals, Inc. | Triazoles as inhibitors of fatty acid synthase |
| CA2798330A1 (en) | 2010-05-05 | 2011-11-10 | Infinity Pharmaceuticals, Inc. | Tetrazolones as inhibitors of fatty acid synthase |
| 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 |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| KR101273566B1 (ko) | 2011-09-05 | 2013-06-11 | 한국과학기술연구원 | 신규한 아제티딘 유도체 및 이를 함유하는 항우울제 조성물 |
| AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
| RU2015106909A (ru) | 2012-08-02 | 2016-09-27 | Мерк Шарп И Доум Корп. | Антидиабетические трициклические соединения |
| US9682940B2 (en) | 2015-08-25 | 2017-06-20 | Janssen Pharmaceutica Nv | Indazole derivatives useful as CB-1 inverse agonists |
| WO2017185037A1 (en) | 2016-04-22 | 2017-10-26 | Acceleron Pharma Inc. | Alk7 binding proteins and uses thereof |
| JP2021535203A (ja) | 2018-08-20 | 2021-12-16 | ベッソール ファルマ、エルエルシー | 既知および新規カンナビノイドの適用 |
| WO2020167701A1 (en) | 2019-02-13 | 2020-08-20 | Merck Sharp & Dohme Corp. | Pyrrolidine orexin receptor agonists |
| US11098029B2 (en) | 2019-02-13 | 2021-08-24 | Merck Sharp & Dohme Corp. | 5-alkyl pyrrolidine orexin receptor agonists |
| WO2021026047A1 (en) | 2019-08-08 | 2021-02-11 | Merck Sharp & Dohme Corp. | Heteroaryl pyrrolidine and piperidine orexin receptor agonists |
| BR112023002957A2 (pt) | 2020-08-18 | 2023-04-04 | Merck Sharp & Dohme Llc | Composto, composição farmacêutica, e, métodos para tratar narcolepsia e para tratar hipersonia em um sujeito mamífero |
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| US4052383A (en) | 1974-10-30 | 1977-10-04 | Schering Corporation | N-diphenylalkyl-2-benzyl azacyclic compounds |
| US4133881A (en) * | 1977-04-27 | 1979-01-09 | A. H. Robins Company, Incorporated | Azetidinyl acetonitrile and acetamide antiarrhythmia compositions and methods |
| US4242261A (en) | 1979-07-19 | 1980-12-30 | A. H. Robins Company, Inc. | Production of methylene-cycloamines |
| EP0912494A1 (en) | 1996-06-07 | 1999-05-06 | Nps Pharmaceuticals, Inc. | Coumpounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| CA2296314A1 (en) | 1997-07-25 | 1999-02-04 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
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| AU2001241927A1 (en) | 2000-02-28 | 2001-09-12 | Scios Inc. | Inhibitors of p38-alpha kinase |
| FR2805817B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives d'azetidine, les nouveaux derives d'azetidine et leur preparation |
| FR2805810B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives de 3- amino-azetidine, les nouveaux derives et leur preparation |
| US6355631B1 (en) * | 2000-03-03 | 2002-03-12 | Aventis Pharma S.A. | Pharmaceutical compositions containing azetidine derivatives, novel azetidine derivatives and their preparation |
| US6479479B2 (en) | 2000-03-03 | 2002-11-12 | Aventis Pharma S.A. | Azetidine derivatives, their preparation and pharmaceutical compositions containing them |
| FR2805818B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les compositions pharmaceutiques les contenant |
| GB0019006D0 (en) | 2000-08-04 | 2000-09-20 | Astrazeneca Ab | Novel compounds |
| FR2814678B1 (fr) | 2000-10-04 | 2002-12-20 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et de sibutramine, les compositions pharmaceutiques les contenant et leur utilisation pour la traitement de l'obesite |
| GB0117387D0 (en) | 2001-07-17 | 2001-09-05 | Novartis Ag | Organic compounds |
| FR2829028B1 (fr) | 2001-08-29 | 2004-12-17 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et d'un produit qui active la neurotransmission dopaminergique dans le cerveau, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de |
| FR2829027A1 (fr) | 2001-08-29 | 2003-03-07 | Aventis Pharma Sa | Association avec un antagoniste du recepteur cb1, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de parkinson |
| JP4660199B2 (ja) | 2002-12-23 | 2011-03-30 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換1−ピペリジン−4−イル−4−アゼチジン−3−イル−ピペラジン誘導体およびそれらのニューロキニン拮抗薬としての使用 |
| AU2004234125A1 (en) | 2003-05-01 | 2004-11-11 | Vernalis Research Limited | Azetidinecarboxamide derivatives and their use in the treatment of CB1 receptor mediated disorders |
| WO2004096794A1 (en) | 2003-05-01 | 2004-11-11 | Vernalis Research Limited | Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordrs |
| 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 |
| JP2007522255A (ja) | 2004-02-17 | 2007-08-09 | ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ | 置換アゼチジン化合物、その製造および医薬品としての使用 |
| US7906652B2 (en) * | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
-
2004
- 2004-06-09 CN CNA2004800160109A patent/CN1802351A/zh active Pending
- 2004-06-09 EP EP04776404A patent/EP1636181A1/en not_active Withdrawn
- 2004-06-09 UA UAA200600239A patent/UA83230C2/ru unknown
- 2004-06-09 AU AU2004252109A patent/AU2004252109B2/en not_active Ceased
- 2004-06-09 BR BRPI0411131-1A patent/BRPI0411131A/pt not_active IP Right Cessation
- 2004-06-09 NZ NZ543451A patent/NZ543451A/en unknown
- 2004-06-09 JP JP2006533655A patent/JP3939744B2/ja not_active Expired - Fee Related
- 2004-06-09 CA CA002527933A patent/CA2527933C/en not_active Expired - Fee Related
- 2004-06-09 RU RU2006100298/04A patent/RU2006100298A/ru not_active Application Discontinuation
- 2004-06-09 WO PCT/US2004/018348 patent/WO2005000809A1/en not_active Ceased
- 2004-06-09 US US10/557,246 patent/US7485732B2/en not_active Expired - Fee Related
- 2004-06-09 KR KR1020057023696A patent/KR20060019587A/ko not_active Ceased
- 2004-06-09 MX MXPA05013583A patent/MXPA05013583A/es unknown
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2005
- 2005-11-08 ZA ZA200509019A patent/ZA200509019B/en unknown
- 2005-11-24 IS IS8146A patent/IS8146A/is unknown
- 2005-12-05 CO CO05123378A patent/CO5650244A2/es not_active Application Discontinuation
- 2005-12-05 MA MA28634A patent/MA27847A1/fr unknown
- 2005-12-06 IL IL172417A patent/IL172417A0/en unknown
- 2005-12-08 EC EC2005006207A patent/ECSP056207A/es unknown
-
2006
- 2006-01-10 NO NO20060141A patent/NO20060141L/no not_active Application Discontinuation
-
2007
- 2007-02-13 JP JP2007031781A patent/JP2007186518A/ja active Pending
-
2008
- 2008-10-21 US US12/288,518 patent/US7906503B2/en not_active Expired - Fee Related
-
2011
- 2011-03-11 JP JP2011053759A patent/JP2011144196A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004252109B2 (en) | 2010-04-08 |
| US7906503B2 (en) | 2011-03-15 |
| NO20060141L (no) | 2006-03-13 |
| JP2007186518A (ja) | 2007-07-26 |
| US7485732B2 (en) | 2009-02-03 |
| JP3939744B2 (ja) | 2007-07-04 |
| NZ543451A (en) | 2008-08-29 |
| EP1636181A1 (en) | 2006-03-22 |
| CN1802351A (zh) | 2006-07-12 |
| CO5650244A2 (es) | 2006-06-30 |
| WO2005000809A1 (en) | 2005-01-06 |
| KR20060019587A (ko) | 2006-03-03 |
| MA27847A1 (fr) | 2006-04-03 |
| CA2527933C (en) | 2009-08-11 |
| IS8146A (is) | 2005-11-24 |
| US20090069284A1 (en) | 2009-03-12 |
| BRPI0411131A (pt) | 2006-07-18 |
| AU2004252109A1 (en) | 2005-01-06 |
| ZA200509019B (en) | 2006-11-29 |
| ECSP056207A (es) | 2006-04-19 |
| IL172417A0 (en) | 2006-04-10 |
| JP2007500246A (ja) | 2007-01-11 |
| UA83230C2 (ru) | 2008-06-25 |
| US20060293299A1 (en) | 2006-12-28 |
| JP2011144196A (ja) | 2011-07-28 |
| MXPA05013583A (es) | 2006-03-09 |
| CA2527933A1 (en) | 2005-01-06 |
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