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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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Urology & Nephrology (AREA)
- 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=) |
Families Citing this family (52)
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| NZ534757A (en) | 2002-03-12 | 2006-07-28 | Merck & Co Inc | Substituted amides |
| EP1558252B1 (en) | 2002-08-02 | 2007-10-10 | Merck & Co., Inc. | Substituted furo [2,3-b]pyridine derivatives |
| EP1575901B1 (en) | 2002-12-19 | 2012-10-10 | Merck Sharp & Dohme Corp. | Substituted amides |
| AU2004252109B2 (en) * | 2003-06-11 | 2010-04-08 | Merck Sharp & Dohme Corp. | Substituted 3-alkyl and 3-alkenyl azetidine derivatives |
| WO2005044785A1 (en) | 2003-10-30 | 2005-05-19 | Merck & Co., Inc. | Aralkyl amines as cannabinoid receptor modulators |
| CA2606188A1 (en) * | 2005-05-02 | 2006-11-09 | Merck & Co., Inc. | Combination of dipeptidyl peptidase-iv inhibitor and a cannabinoid cb1 receptor antagonist for the treatment of diabetes and obesity |
| BRPI0616463A2 (pt) | 2005-09-29 | 2011-06-21 | Merck & Co Inc | composto, composição farmacêutica, e, uso de um composto |
| US7906652B2 (en) * | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| AR058199A1 (es) * | 2005-11-28 | 2008-01-23 | Merck & Co Inc | Derivados de 3- alquilazetidina sustituidos con heterociclos |
| DOP2006000273A (es) * | 2005-12-08 | 2007-10-15 | Aventis Pharma Inc | Uso de un antagonista de cb1 para tratar efectos secundarios y sintomas negativos de la esquizofrenia |
| CN101389648B (zh) | 2006-02-22 | 2013-07-17 | 默沙东公司 | 肽胃泌酸调节素衍生物 |
| 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 |
| JP5489333B2 (ja) | 2006-09-22 | 2014-05-14 | メルク・シャープ・アンド・ドーム・コーポレーション | 脂肪酸合成阻害剤を用いた治療の方法 |
| 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 |
| CA2682727C (en) | 2007-04-02 | 2016-03-22 | Banyu Pharmaceutical Co., Ltd. | Indoledione derivative |
| EP2546232A1 (en) | 2007-06-20 | 2013-01-16 | Merck Sharp & Dohme Corp. | 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 |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| EP2350020B1 (en) | 2008-10-03 | 2014-08-13 | Merck Sharp & Dohme Corp. | Spiro-imidazolone derivatives as glucagon receptor antagonists |
| WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP5635991B2 (ja) | 2008-10-30 | 2014-12-03 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | イソニコチンアミドオレキシン受容体アンタゴニスト |
| 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 |
| WO2010144664A1 (en) | 2009-06-12 | 2010-12-16 | Schering Corporation | Thiophenes as glucagon receptor antagonists, compositions, and methods for their use |
| 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 |
| EP3159331A1 (en) | 2010-05-05 | 2017-04-26 | Infinity Pharmaceuticals, Inc. | Tetrazolones as inhibitors of fatty acid synthase |
| US8450350B2 (en) | 2010-05-05 | 2013-05-28 | Infinity Pharmaceuticals, Inc. | Triazoles as inhibitors of fatty acid synthase |
| 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 |
| 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 |
| 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 |
| 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 |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, 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 |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| 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 |
| 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 |
| 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 |
| 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 |
| US9527875B2 (en) | 2012-08-02 | 2016-12-27 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| US9682940B2 (en) | 2015-08-25 | 2017-06-20 | Janssen Pharmaceutica Nv | Indazole derivatives useful as CB-1 inverse agonists |
| CN116217731B (zh) | 2016-04-22 | 2025-12-30 | 艾科赛扬制药股份有限公司 | Alk7结合蛋白及其用途 |
| WO2020041322A1 (en) | 2018-08-20 | 2020-02-27 | Berkowitz Barry A | Novel cannabinoids and cannabinoid acids and their derivatives |
| 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 |
| US12312332B2 (en) | 2019-08-08 | 2025-05-27 | Merck Sharp & Dohme Llc | 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 |
| WO1997046511A1 (en) | 1996-06-07 | 1997-12-11 | Nps Pharmaceuticals, Inc. | Coumpounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| WO1999004794A1 (en) | 1997-07-25 | 1999-02-04 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
| FR2783246B1 (fr) | 1998-09-11 | 2000-11-17 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les medicaments les contenant |
| IL141769A0 (en) | 1998-09-11 | 2002-03-10 | Aventis Pharma Sa | Azetidine derivatives, preparation and medicines containing them |
| JP2003500392A (ja) | 1999-05-25 | 2003-01-07 | セプラコール, インク. | 複素環式鎮痛性化合物およびその使用方法 |
| US6635661B2 (en) | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
| AU2001241927A1 (en) | 2000-02-28 | 2001-09-12 | Scios Inc. | Inhibitors of p38-alpha kinase |
| FR2805818B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les compositions pharmaceutiques les contenant |
| 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 |
| 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 |
| CA2509406C (en) | 2002-12-23 | 2012-07-03 | Janssen Pharmaceutica N.V. | Substituted 1-piperidin-4-yl-4-azetidin-3-yl-piperazine derivatives and their use as neurokinin antagonists |
| JP2006525299A (ja) | 2003-05-01 | 2006-11-09 | ヴァーナリス リサーチ リミテッド | アゼチジンカルボキサミド誘導体及びcb1レセプター媒介障害の治療におけるその使用 |
| ATE453620T1 (de) | 2003-05-01 | 2010-01-15 | Vernalis Res Ltd | Azetidincarboxamid-derivate zur verwendung zur behandlung von cb1-rezeptor-vermittelten krankheiten |
| AU2004252109B2 (en) | 2003-06-11 | 2010-04-08 | Merck Sharp & Dohme Corp. | Substituted 3-alkyl and 3-alkenyl azetidine derivatives |
| KR20060124756A (ko) | 2004-02-17 | 2006-12-05 | 라보라토리오스 델 드라. 에스테브.에스.에이. | 치환된 아제티딘 화합물, 그 제조 및 약제로써의 용도 |
| US7906652B2 (en) * | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
-
2004
- 2004-06-09 AU AU2004252109A patent/AU2004252109B2/en not_active Ceased
- 2004-06-09 RU RU2006100298/04A patent/RU2006100298A/ru not_active Application Discontinuation
- 2004-06-09 US US10/557,246 patent/US7485732B2/en not_active Expired - Fee Related
- 2004-06-09 CN CNA2004800160109A patent/CN1802351A/zh active Pending
- 2004-06-09 MX MXPA05013583A patent/MXPA05013583A/es unknown
- 2004-06-09 KR KR1020057023696A patent/KR20060019587A/ko not_active Ceased
- 2004-06-09 UA UAA200600239A patent/UA83230C2/ru unknown
- 2004-06-09 NZ NZ543451A patent/NZ543451A/en unknown
- 2004-06-09 CA CA002527933A patent/CA2527933C/en not_active Expired - Fee Related
- 2004-06-09 BR BRPI0411131-1A patent/BRPI0411131A/pt not_active IP Right Cessation
- 2004-06-09 WO PCT/US2004/018348 patent/WO2005000809A1/en not_active Ceased
- 2004-06-09 EP EP04776404A patent/EP1636181A1/en not_active Withdrawn
- 2004-06-09 JP JP2006533655A patent/JP3939744B2/ja not_active Expired - Fee Related
-
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 |
|---|---|
| MA27847A1 (fr) | 2006-04-03 |
| NO20060141L (no) | 2006-03-13 |
| CO5650244A2 (es) | 2006-06-30 |
| ECSP056207A (es) | 2006-04-19 |
| US7485732B2 (en) | 2009-02-03 |
| WO2005000809A1 (en) | 2005-01-06 |
| JP2007186518A (ja) | 2007-07-26 |
| BRPI0411131A (pt) | 2006-07-18 |
| KR20060019587A (ko) | 2006-03-03 |
| IL172417A0 (en) | 2006-04-10 |
| JP2011144196A (ja) | 2011-07-28 |
| JP2007500246A (ja) | 2007-01-11 |
| EP1636181A1 (en) | 2006-03-22 |
| US7906503B2 (en) | 2011-03-15 |
| JP3939744B2 (ja) | 2007-07-04 |
| CA2527933C (en) | 2009-08-11 |
| NZ543451A (en) | 2008-08-29 |
| IS8146A (is) | 2005-11-24 |
| US20090069284A1 (en) | 2009-03-12 |
| UA83230C2 (ru) | 2008-06-25 |
| US20060293299A1 (en) | 2006-12-28 |
| MXPA05013583A (es) | 2006-03-09 |
| CA2527933A1 (en) | 2005-01-06 |
| AU2004252109A1 (en) | 2005-01-06 |
| AU2004252109B2 (en) | 2010-04-08 |
| CN1802351A (zh) | 2006-07-12 |
| ZA200509019B (en) | 2006-11-29 |
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