JP2007186518A5 - - Google Patents
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- Publication number
- JP2007186518A5 JP2007186518A5 JP2007031781A JP2007031781A JP2007186518A5 JP 2007186518 A5 JP2007186518 A5 JP 2007186518A5 JP 2007031781 A JP2007031781 A JP 2007031781A JP 2007031781 A JP2007031781 A JP 2007031781A JP 2007186518 A5 JP2007186518 A5 JP 2007186518A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- chlorophenyl
- azetidin
- difluorophenyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 89
- 125000001424 substituent group Chemical group 0.000 claims 53
- -1 (2) pyridyl Chemical group 0.000 claims 43
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000003118 aryl group Chemical group 0.000 claims 32
- 150000002367 halogens Chemical class 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 25
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 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 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 229910052799 carbon Inorganic materials 0.000 claims 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 15
- 125000003342 alkenyl group Chemical group 0.000 claims 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 150000001721 carbon Chemical group 0.000 claims 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 claims 8
- 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 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 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 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 5
- 208000030814 Eating disease Diseases 0.000 claims 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 5
- 208000008589 Obesity Diseases 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 235000014632 disordered eating Nutrition 0.000 claims 5
- 235000020824 obesity Nutrition 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 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 4
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical group NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000037406 food intake Effects 0.000 claims 4
- 235000012631 food intake Nutrition 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims 3
- 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
- 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 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
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 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
- 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
- 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 2
- 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 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
- SIGYZOKUSLPHLI-CLJLJLNGSA-N 3-[(r)-(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-CLJLJLNGSA-N 0.000 claims 2
- LNMYLXDJQSWDJY-SXOMAYOGSA-N 3-[(s)-(4-chlorophenyl)-[3-[(1s)-2-fluoro-1-(3-fluoro-5-methylsulfanylphenyl)-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound CSC1=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 LNMYLXDJQSWDJY-SXOMAYOGSA-N 0.000 claims 2
- 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 2
- 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 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
- MHEVPMYEQARYHI-UHFFFAOYSA-N CC(C)N(C(C)C(=C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F)C(=O)O Chemical compound CC(C)N(C(C)C(=C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F)C(=O)O MHEVPMYEQARYHI-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 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
- OIWVOZPUSMHYSI-UHFFFAOYSA-N 1-[(4-bromothiophen-2-yl)-(4-chlorophenyl)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=CC(Cl)=CC=1)C1=CC(Br)=CS1 OIWVOZPUSMHYSI-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
- 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 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
- 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 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
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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-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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- 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
- 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 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
- SIGYZOKUSLPHLI-IZZNHLLZSA-N 3-[(r)-(4-chlorophenyl)-[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(Cl)C=C1 SIGYZOKUSLPHLI-IZZNHLLZSA-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
- 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 1
- LNMYLXDJQSWDJY-KAYWLYCHSA-N 3-[(r)-(4-chlorophenyl)-[3-[(1s)-2-fluoro-1-(3-fluoro-5-methylsulfanylphenyl)-2-methylpropyl]azetidin-1-yl]methyl]benzonitrile Chemical compound CSC1=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 LNMYLXDJQSWDJY-KAYWLYCHSA-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
- 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
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-
2004
- 2004-06-09 KR KR1020057023696A patent/KR20060019587A/ko not_active Ceased
- 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 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 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 UA UAA200600239A patent/UA83230C2/ru unknown
- 2004-06-09 CN CNA2004800160109A patent/CN1802351A/zh active Pending
- 2004-06-09 JP JP2006533655A patent/JP3939744B2/ja not_active Expired - Fee Related
- 2004-06-09 NZ NZ543451A patent/NZ543451A/en unknown
- 2004-06-09 MX MXPA05013583A patent/MXPA05013583A/es unknown
- 2004-06-09 AU AU2004252109A patent/AU2004252109B2/en not_active Ceased
-
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
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2011
- 2011-03-11 JP JP2011053759A patent/JP2011144196A/ja not_active Withdrawn
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