HRP20030249A2 - Association of the cb1 receptor antagonist and a sibutramin, pharmaceutical compositions containing same and use thereof for treating obesity - Google Patents
Association of the cb1 receptor antagonist and a sibutramin, pharmaceutical compositions containing same and use thereof for treating obesity Download PDFInfo
- Publication number
- HRP20030249A2 HRP20030249A2 HR20030249A HRP20030249A HRP20030249A2 HR P20030249 A2 HRP20030249 A2 HR P20030249A2 HR 20030249 A HR20030249 A HR 20030249A HR P20030249 A HRP20030249 A HR P20030249A HR P20030249 A2 HRP20030249 A2 HR P20030249A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- chlorophenyl
- methylsulfonyl
- bis
- azetidine
- Prior art date
Links
- 208000008589 Obesity Diseases 0.000 title abstract description 7
- 235000020824 obesity Nutrition 0.000 title abstract description 7
- 229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 title abstract description 5
- 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 title abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- -1 -COOR5 Chemical group 0.000 claims description 141
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 138
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 114
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 38
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 239000011593 sulfur Chemical group 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000002619 bicyclic group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 229940124802 CB1 antagonist Drugs 0.000 claims description 16
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 15
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims description 15
- 229960004425 sibutramine Drugs 0.000 claims description 14
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 12
- 150000001491 aromatic compounds Chemical class 0.000 claims description 12
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 150000002390 heteroarenes Chemical class 0.000 claims description 12
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
- RAVRTQMDHKJJIW-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 RAVRTQMDHKJJIW-UHFFFAOYSA-N 0.000 claims description 8
- MDIRSOMJVCIVSW-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-piperidin-1-ylbenzamide Chemical compound C=1C=CC(C(=O)NN2CCCCC2)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 MDIRSOMJVCIVSW-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims description 8
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 8
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 8
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- 125000005493 quinolyl group Chemical group 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 7
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- ZITKLNYNZGFLFM-UHFFFAOYSA-N n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-4-methylsulfonylbenzamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1CN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C1 ZITKLNYNZGFLFM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- ZGYFLQUPOCALIL-UHFFFAOYSA-N 1-benzhydryl-3-[methylsulfonyl-[3-(trifluoromethoxy)phenyl]methylidene]azetidine Chemical compound C=1C=CC(OC(F)(F)F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZGYFLQUPOCALIL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- BIHRKCOQNANFPP-HSZRJFAPSA-N 1-[(r)-(4-chlorophenyl)-(2,4-dichlorophenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C(=CC(Cl)=CC=2)Cl)=CC=C(Cl)C=C1 BIHRKCOQNANFPP-HSZRJFAPSA-N 0.000 claims description 3
- NVAZILBISPTELT-OAQYLSRUSA-N 1-[(r)-(4-chlorophenyl)-thiophen-2-ylmethyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C1([C@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(Cl)=CC=2)=CC=CS1 NVAZILBISPTELT-OAQYLSRUSA-N 0.000 claims description 3
- NVAZILBISPTELT-NRFANRHFSA-N 1-[(s)-(4-chlorophenyl)-thiophen-2-ylmethyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(Cl)=CC=2)=CC=CS1 NVAZILBISPTELT-NRFANRHFSA-N 0.000 claims description 3
- SDJUKPVOYHWILZ-UHFFFAOYSA-N 1-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]phenyl]pyrrolidine Chemical compound C=1C=CC(N2CCCC2)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 SDJUKPVOYHWILZ-UHFFFAOYSA-N 0.000 claims description 3
- SOPDUJWVNOSRDR-GDLZYMKVSA-N 1-[[4-[(r)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]piperidine Chemical compound C1([C@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CN3CCCCC3)=CC=2)=CC=C(Cl)C=C1 SOPDUJWVNOSRDR-GDLZYMKVSA-N 0.000 claims description 3
- WKOAOEVZSBATJT-PMERELPUSA-N 1-[[4-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]-3,3-dimethylpiperidine Chemical compound C1C(C)(C)CCCN1CC1=CC=C([C@H](N2CC(C2)=C(C=2C=C(F)C=C(F)C=2)S(C)(=O)=O)C=2C=CC(Cl)=CC=2)C=C1 WKOAOEVZSBATJT-PMERELPUSA-N 0.000 claims description 3
- FBWVTEZCNIQJRF-LJAQVGFWSA-N 1-[[4-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=C([C@H](N2CC(C2)=C(C=2C=C(F)C=C(F)C=2)S(C)(=O)=O)C=2C=CC(Cl)=CC=2)C=C1 FBWVTEZCNIQJRF-LJAQVGFWSA-N 0.000 claims description 3
- ZGLXDYITFVRVCG-NDEPHWFRSA-N 1-[[4-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]pyrrolidine Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CN3CCCC3)=CC=2)=CC=C(Cl)C=C1 ZGLXDYITFVRVCG-NDEPHWFRSA-N 0.000 claims description 3
- FFVNJEJANVAWEH-UHFFFAOYSA-N 1-[bis(2-fluorophenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C(=CC=CC=1)F)C1=CC=CC=C1F FFVNJEJANVAWEH-UHFFFAOYSA-N 0.000 claims description 3
- VZWQRIMUBIPTIM-UHFFFAOYSA-N 1-[bis(3-fluorophenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=C(F)C=CC=1)C1=CC=CC(F)=C1 VZWQRIMUBIPTIM-UHFFFAOYSA-N 0.000 claims description 3
- LVLGJPPXNPPWIO-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]-3-[(3-methoxyphenyl)-methylsulfonylmethylidene]azetidine Chemical compound COC1=CC=CC(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 LVLGJPPXNPPWIO-UHFFFAOYSA-N 0.000 claims description 3
- RGMVGFUHTMCAHQ-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]-3-[methylsulfonylmethylsulfonyl-[3-(trifluoromethylsulfanyl)phenyl]methylidene]azetidine Chemical compound C=1C=CC(SC(F)(F)F)=CC=1C(S(=O)(=O)CS(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 RGMVGFUHTMCAHQ-UHFFFAOYSA-N 0.000 claims description 3
- HBLQMBNUYUVOKF-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]-n-[(3,5-difluorophenyl)methyl]azetidin-3-amine Chemical compound FC1=CC(F)=CC(CNC2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 HBLQMBNUYUVOKF-UHFFFAOYSA-N 0.000 claims description 3
- DSIMSFUZYRACNE-UHFFFAOYSA-N 1-[bis(4-fluorophenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 DSIMSFUZYRACNE-UHFFFAOYSA-N 0.000 claims description 3
- ZUJLEGLMCBXZBA-UHFFFAOYSA-N 1-[bis(4-methoxyphenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 ZUJLEGLMCBXZBA-UHFFFAOYSA-N 0.000 claims description 3
- GXDNYOGWFZOREO-UHFFFAOYSA-N 1-[bis(4-methylphenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 GXDNYOGWFZOREO-UHFFFAOYSA-N 0.000 claims description 3
- HCYHNZJIUZTTFK-UHFFFAOYSA-N 1-[bis[4-(trifluoromethoxy)phenyl]methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(OC(F)(F)F)=CC=1)C1=CC=C(OC(F)(F)F)C=C1 HCYHNZJIUZTTFK-UHFFFAOYSA-N 0.000 claims description 3
- COEFGPCJQSWIJQ-UHFFFAOYSA-N 1-benzhydryl-3-[(2,3-dichlorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C=CC(Cl)=C(Cl)C=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 COEFGPCJQSWIJQ-UHFFFAOYSA-N 0.000 claims description 3
- ZXMARMGTUBBFHE-UHFFFAOYSA-N 1-benzhydryl-3-[(2,5-dichlorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(Cl)=CC=C(Cl)C=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZXMARMGTUBBFHE-UHFFFAOYSA-N 0.000 claims description 3
- USKXXLXCEAKGIL-UHFFFAOYSA-N 1-benzhydryl-3-[(3,5-dichlorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 USKXXLXCEAKGIL-UHFFFAOYSA-N 0.000 claims description 3
- BEZKBMXRTCXDEK-UHFFFAOYSA-N 1-benzhydryl-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BEZKBMXRTCXDEK-UHFFFAOYSA-N 0.000 claims description 3
- IHEGLFXGTJAGNN-UHFFFAOYSA-N 1-benzhydryl-3-[(3-bromophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C=CC(Br)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 IHEGLFXGTJAGNN-UHFFFAOYSA-N 0.000 claims description 3
- ATLHMTLEQJOFKX-UHFFFAOYSA-N 1-benzhydryl-3-[(3-chlorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C=CC(Cl)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ATLHMTLEQJOFKX-UHFFFAOYSA-N 0.000 claims description 3
- CXVCKVBWGQDVAX-UHFFFAOYSA-N 1-benzhydryl-3-[(3-fluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 CXVCKVBWGQDVAX-UHFFFAOYSA-N 0.000 claims description 3
- ZEHGNVXHYPKEHO-UHFFFAOYSA-N 1-benzhydryl-3-[(3-iodophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C=CC(I)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZEHGNVXHYPKEHO-UHFFFAOYSA-N 0.000 claims description 3
- VGLYSTYECJHDJB-UHFFFAOYSA-N 1-benzhydryl-3-[(3-methylphenyl)-methylsulfonylmethylidene]azetidine Chemical compound CC1=CC=CC(C(=C2CN(C2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)S(C)(=O)=O)=C1 VGLYSTYECJHDJB-UHFFFAOYSA-N 0.000 claims description 3
- JCXAARLJXDJMCB-UHFFFAOYSA-N 1-benzhydryl-3-[[3,5-bis(trifluoromethyl)phenyl]-methylsulfonylmethylidene]azetidine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JCXAARLJXDJMCB-UHFFFAOYSA-N 0.000 claims description 3
- OFVJVEPORFCDQL-UHFFFAOYSA-N 1-benzhydryl-3-[ethylsulfonyl(phenyl)methylidene]azetidine Chemical compound C=1C=CC=CC=1C(S(=O)(=O)CC)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 OFVJVEPORFCDQL-UHFFFAOYSA-N 0.000 claims description 3
- DYAHYJVGFCXPLL-UHFFFAOYSA-N 1-benzhydryl-3-[methylsulfonyl(phenyl)methylidene]azetidine Chemical compound C=1C=CC=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 DYAHYJVGFCXPLL-UHFFFAOYSA-N 0.000 claims description 3
- HLOUATKBBLVAOQ-UHFFFAOYSA-N 2-(benzenesulfonyl)-n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC(NC(=O)CS(=O)(=O)C=2C=CC=CC=2)C1 HLOUATKBBLVAOQ-UHFFFAOYSA-N 0.000 claims description 3
- UYMOXHDJOGNHGD-LJQANCHMSA-N 2-[(r)-(4-chlorophenyl)-[3-[methylsulfonyl(phenyl)methylidene]azetidin-1-yl]methyl]-1,3-thiazole Chemical compound C1([C@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=CS1 UYMOXHDJOGNHGD-LJQANCHMSA-N 0.000 claims description 3
- KSEYYUPAXNLWPF-IBGZPJMESA-N 2-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]-1,3-thiazole Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(Cl)=CC=2)=NC=CS1 KSEYYUPAXNLWPF-IBGZPJMESA-N 0.000 claims description 3
- UYMOXHDJOGNHGD-IBGZPJMESA-N 2-[(s)-(4-chlorophenyl)-[3-[methylsulfonyl(phenyl)methylidene]azetidin-1-yl]methyl]-1,3-thiazole Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=CS1 UYMOXHDJOGNHGD-IBGZPJMESA-N 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- CEAFTNGPOKSUCY-UHFFFAOYSA-N 3-[(1-benzhydrylazetidin-3-ylidene)-methylsulfonylmethyl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 CEAFTNGPOKSUCY-UHFFFAOYSA-N 0.000 claims description 3
- FRTCYRCXRQVABW-UHFFFAOYSA-N 3-[(1-benzhydrylazetidin-3-ylidene)-methylsulfonylmethyl]benzonitrile Chemical compound C=1C=CC(C#N)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 FRTCYRCXRQVABW-UHFFFAOYSA-N 0.000 claims description 3
- VGMIYPGXWOUQFS-XMMPIXPASA-N 3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]-1-[(r)-(4-methoxyphenyl)-phenylmethyl]azetidine Chemical compound C1=CC(OC)=CC=C1[C@@H](C=1C=CC=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 VGMIYPGXWOUQFS-XMMPIXPASA-N 0.000 claims description 3
- VGMIYPGXWOUQFS-DEOSSOPVSA-N 3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]-1-[(s)-(4-methoxyphenyl)-phenylmethyl]azetidine Chemical compound C1=CC(OC)=CC=C1[C@H](C=1C=CC=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 VGMIYPGXWOUQFS-DEOSSOPVSA-N 0.000 claims description 3
- WWFZLYVGAVYSHR-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=CC(C(=O)NCCN2CCOCC2)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 WWFZLYVGAVYSHR-UHFFFAOYSA-N 0.000 claims description 3
- FRPWVAZATMLFSJ-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-(3-morpholin-4-ylpropyl)benzamide Chemical compound C=1C=CC(C(=O)NCCCN2CCOCC2)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 FRPWVAZATMLFSJ-UHFFFAOYSA-N 0.000 claims description 3
- QOFJARYKNHCFOP-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1NC(=O)C1=CC=CC(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 QOFJARYKNHCFOP-UHFFFAOYSA-N 0.000 claims description 3
- UOUGWWQPFUAXGJ-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 UOUGWWQPFUAXGJ-UHFFFAOYSA-N 0.000 claims description 3
- MFOXSVVWCRZNKV-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-methylaniline Chemical compound CNC1=CC=CC(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 MFOXSVVWCRZNKV-UHFFFAOYSA-N 0.000 claims description 3
- OHSIVRGAGQXRCH-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 OHSIVRGAGQXRCH-UHFFFAOYSA-N 0.000 claims description 3
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- QQRVMMYVSMOPDG-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]phenol Chemical compound C=1C=CC(O)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 QQRVMMYVSMOPDG-UHFFFAOYSA-N 0.000 claims description 3
- NVWZAORPAUTJDW-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-(2,2-dimethylpropyl)benzamide Chemical compound CC(C)(C)CNC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 NVWZAORPAUTJDW-UHFFFAOYSA-N 0.000 claims description 3
- HZLYURCOFSSNJH-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-(2,2-diphenylethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N(C1)CC1=CS(=O)(=O)CC1=CC=CC(C(=O)NCC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HZLYURCOFSSNJH-UHFFFAOYSA-N 0.000 claims description 3
- LJMMGNDPDWRUDG-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-(2-ethylbutyl)benzamide Chemical compound CCC(CC)CNC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 LJMMGNDPDWRUDG-UHFFFAOYSA-N 0.000 claims description 3
- MXUGPRCHGYVTST-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-(2-methylbutyl)benzamide Chemical compound CCC(C)CNC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 MXUGPRCHGYVTST-UHFFFAOYSA-N 0.000 claims description 3
- QYGSMFQHYQQGGR-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-(2-methylpropyl)benzamide Chemical compound CC(C)CNC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 QYGSMFQHYQQGGR-UHFFFAOYSA-N 0.000 claims description 3
- CNMDTGYRPPZEBQ-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-(cyclohexylmethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N(C1)CC1=CS(=O)(=O)CC1=CC=CC(C(=O)NCC2CCCCC2)=C1 CNMDTGYRPPZEBQ-UHFFFAOYSA-N 0.000 claims description 3
- NVLVGHQEGLQVIL-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-(cyclopropylmethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N(C1)CC1=CS(=O)(=O)CC1=CC=CC(C(=O)NCC2CC2)=C1 NVLVGHQEGLQVIL-UHFFFAOYSA-N 0.000 claims description 3
- KTDXDPJKASEDKT-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-[(1-ethylpyrrolidin-2-yl)methyl]benzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 KTDXDPJKASEDKT-UHFFFAOYSA-N 0.000 claims description 3
- BWZFAJHFKSCWLS-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-[1-(dimethylamino)propan-2-yl]benzamide Chemical compound CN(C)CC(C)NC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 BWZFAJHFKSCWLS-UHFFFAOYSA-N 0.000 claims description 3
- OZHYCUGWABHDFR-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]-n-[3-(dimethylamino)propyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 OZHYCUGWABHDFR-UHFFFAOYSA-N 0.000 claims description 3
- ZUQQILFPHCUUQO-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ZUQQILFPHCUUQO-UHFFFAOYSA-N 0.000 claims description 3
- PGHBUQMOEMEUNT-UHFFFAOYSA-N 3-n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]benzene-1,3-disulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(S(=O)(=O)NC2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 PGHBUQMOEMEUNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- VKYOAPIHWDRWCF-RUZDIDTESA-N 4-[(r)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1[C@H](C=1C=CC(Cl)=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 VKYOAPIHWDRWCF-RUZDIDTESA-N 0.000 claims description 3
- GLXILTSCZKNOJQ-RUZDIDTESA-N 4-[(r)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1[C@H](C=1C=CC(Cl)=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 GLXILTSCZKNOJQ-RUZDIDTESA-N 0.000 claims description 3
- GLXILTSCZKNOJQ-VWLOTQADSA-N 4-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1[C@@H](C=1C=CC(Cl)=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 GLXILTSCZKNOJQ-VWLOTQADSA-N 0.000 claims description 3
- NANRSOWQCYTYCU-UHFFFAOYSA-N 4-[4-[3-[(1-benzhydrylazetidin-3-ylidene)methylsulfonylmethyl]phenoxy]butyl]morpholine Chemical compound C1N(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1=CS(=O)(=O)CC(C=1)=CC=CC=1OCCCCN1CCOCC1 NANRSOWQCYTYCU-UHFFFAOYSA-N 0.000 claims description 3
- OIJLKMYMEOURJA-MUUNZHRXSA-N 4-[[4-[(r)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]morpholine Chemical compound C1([C@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CN3CCOCC3)=CC=2)=CC=C(Cl)C=C1 OIJLKMYMEOURJA-MUUNZHRXSA-N 0.000 claims description 3
- OIJLKMYMEOURJA-NDEPHWFRSA-N 4-[[4-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]morpholine Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CN3CCOCC3)=CC=2)=CC=C(Cl)C=C1 OIJLKMYMEOURJA-NDEPHWFRSA-N 0.000 claims description 3
- RYNSGDFWBJWWSZ-UHFFFAOYSA-N 4-[[6-methoxy-2-(4-methoxyphenyl)-3-benzofuranyl]-oxomethyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C=2C=CC(=CC=2)C#N)C2=CC=C(OC)C=C2O1 RYNSGDFWBJWWSZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- PSZFVCAQCDIBRW-UHFFFAOYSA-N 5-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-(2-methylpropyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)NCC(C)C)=CC=C1C(S(C)(=O)=O)=C1CN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C1 PSZFVCAQCDIBRW-UHFFFAOYSA-N 0.000 claims description 3
- QBQRVMHAUZKPEQ-UHFFFAOYSA-N CC1=CSC(S(C)(=O)=O)=C1C=C.NC(C1)C(C(O)=O)N1C(C(C=C1)=CC=C1Cl)C(C=C1)=CC=C1Cl Chemical compound CC1=CSC(S(C)(=O)=O)=C1C=C.NC(C1)C(C(O)=O)N1C(C(C=C1)=CC=C1Cl)C(C=C1)=CC=C1Cl QBQRVMHAUZKPEQ-UHFFFAOYSA-N 0.000 claims description 3
- XQCLHPYLUJPZBT-UHFFFAOYSA-N CS(C1=CSC=C1Cl)(=O)=O.NC(C1)C(C(O)=O)N1C(C(C=C1)=CC=C1Cl)C(C=C1)=CC=C1Cl Chemical compound CS(C1=CSC=C1Cl)(=O)=O.NC(C1)C(C(O)=O)N1C(C(C=C1)=CC=C1Cl)C(C=C1)=CC=C1Cl XQCLHPYLUJPZBT-UHFFFAOYSA-N 0.000 claims description 3
- PGDDYDAGRXBVAI-UHFFFAOYSA-N FC1=CC(F)=CC(CN(C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(=O)=O)=C1 Chemical compound FC1=CC(F)=CC(CN(C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(=O)=O)=C1 PGDDYDAGRXBVAI-UHFFFAOYSA-N 0.000 claims description 3
- NAXUDNAEIIAYRQ-UHFFFAOYSA-N [3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]phenyl]methanol Chemical compound C=1C=CC(CO)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 NAXUDNAEIIAYRQ-UHFFFAOYSA-N 0.000 claims description 3
- AIZZQTVOXQNBPB-UHFFFAOYSA-N [4-[(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methanol Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(CO)=CC=1)C1=CC=C(Cl)C=C1 AIZZQTVOXQNBPB-UHFFFAOYSA-N 0.000 claims description 3
- AIZZQTVOXQNBPB-XMMPIXPASA-N [4-[(r)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methanol Chemical compound C1([C@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CO)=CC=2)=CC=C(Cl)C=C1 AIZZQTVOXQNBPB-XMMPIXPASA-N 0.000 claims description 3
- AIZZQTVOXQNBPB-DEOSSOPVSA-N [4-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methanol Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CO)=CC=2)=CC=C(Cl)C=C1 AIZZQTVOXQNBPB-DEOSSOPVSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- QKASKKMDZXXIET-UHFFFAOYSA-N methyl 3-[(1-benzhydrylazetidin-3-ylidene)-methylsulfonylmethyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=C2CN(C2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)S(C)(=O)=O)=C1 QKASKKMDZXXIET-UHFFFAOYSA-N 0.000 claims description 3
- GSURFFSJZXJJQJ-UHFFFAOYSA-N methyl 4-[[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]-(4-methoxycarbonylphenyl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(C=1C=CC(=CC=1)C(=O)OC)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 GSURFFSJZXJJQJ-UHFFFAOYSA-N 0.000 claims description 3
- WHWRHLAHKVGQMU-UHFFFAOYSA-N methyl 5-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C(S(C)(=O)=O)=C1CN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C1 WHWRHLAHKVGQMU-UHFFFAOYSA-N 0.000 claims description 3
- XZLPOJOSMALGTC-XKDCRVNJSA-N n-[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]-n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]methanesulfonamide Chemical compound CS(=O)(=O)N([C@H]1[C@@H]2CC[C@@H](C2)C1)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 XZLPOJOSMALGTC-XKDCRVNJSA-N 0.000 claims description 3
- TUHDYGZZOSVEIS-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)-pyridin-3-ylmethyl]azetidin-3-yl]-n-(3,5-difluorophenyl)methanesulfonamide Chemical compound C=1C(F)=CC(F)=CC=1N(S(=O)(=O)C)C(C1)CN1C(C=1C=NC=CC=1)C1=CC=C(Cl)C=C1 TUHDYGZZOSVEIS-UHFFFAOYSA-N 0.000 claims description 3
- TUHDYGZZOSVEIS-JOCHJYFZSA-N n-[1-[(r)-(4-chlorophenyl)-pyridin-3-ylmethyl]azetidin-3-yl]-n-(3,5-difluorophenyl)methanesulfonamide Chemical compound C1([C@@H](N2CC(C2)N(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=NC=CC=2)=CC=C(Cl)C=C1 TUHDYGZZOSVEIS-JOCHJYFZSA-N 0.000 claims description 3
- SIQYQDZVTXFIHU-JOCHJYFZSA-N n-[1-[(r)-(4-chlorophenyl)-pyridin-4-ylmethyl]azetidin-3-yl]-n-(3,5-difluorophenyl)methanesulfonamide Chemical compound C1([C@H](N2CC(C2)N(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(Cl)=CC=2)=CC=NC=C1 SIQYQDZVTXFIHU-JOCHJYFZSA-N 0.000 claims description 3
- LXSJIKMOZWBXLC-OAQYLSRUSA-N n-[1-[(r)-(4-chlorophenyl)-pyrimidin-5-ylmethyl]azetidin-3-yl]-n-(3,5-difluorophenyl)methanesulfonamide Chemical compound C1([C@@H](N2CC(C2)N(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=NC=NC=2)=CC=C(Cl)C=C1 LXSJIKMOZWBXLC-OAQYLSRUSA-N 0.000 claims description 3
- SIQYQDZVTXFIHU-QFIPXVFZSA-N n-[1-[(s)-(4-chlorophenyl)-pyridin-4-ylmethyl]azetidin-3-yl]-n-(3,5-difluorophenyl)methanesulfonamide Chemical compound C1([C@@H](N2CC(C2)N(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(Cl)=CC=2)=CC=NC=C1 SIQYQDZVTXFIHU-QFIPXVFZSA-N 0.000 claims description 3
- LXSJIKMOZWBXLC-NRFANRHFSA-N n-[1-[(s)-(4-chlorophenyl)-pyrimidin-5-ylmethyl]azetidin-3-yl]-n-(3,5-difluorophenyl)methanesulfonamide Chemical compound C1([C@H](N2CC(C2)N(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=NC=NC=2)=CC=C(Cl)C=C1 LXSJIKMOZWBXLC-NRFANRHFSA-N 0.000 claims description 3
- IPJQIXUTBWDAKL-UHFFFAOYSA-N n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-phenylmethanesulfonamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC(NS(=O)(=O)CC=2C=CC=CC=2)C1 IPJQIXUTBWDAKL-UHFFFAOYSA-N 0.000 claims description 3
- TWAKXQFGGJVBJY-UHFFFAOYSA-N n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 TWAKXQFGGJVBJY-UHFFFAOYSA-N 0.000 claims description 3
- PIJIMSMSLQEXCB-UHFFFAOYSA-N n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-2-(4-methylphenyl)sulfonylacetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(=O)NC1CN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C1 PIJIMSMSLQEXCB-UHFFFAOYSA-N 0.000 claims description 3
- XVKRTKCONIOYGB-UHFFFAOYSA-N n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-3,4-dichlorobenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)C1 XVKRTKCONIOYGB-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Plant Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0012646A FR2814678B1 (fr) | 2000-10-04 | 2000-10-04 | Association d'un antagoniste du recepteur cb1 et de sibutramine, les compositions pharmaceutiques les contenant et leur utilisation pour la traitement de l'obesite |
| PCT/FR2001/003022 WO2002028346A2 (fr) | 2000-10-04 | 2001-10-01 | Association d'un antagoniste du recepteur cb1 et de sibutramine, pour le traitement de l'obesite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20030249A2 true HRP20030249A2 (en) | 2005-02-28 |
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|---|---|---|---|
| HR20030249A HRP20030249A2 (en) | 2000-10-04 | 2003-04-02 | Association of the cb1 receptor antagonist and a sibutramin, pharmaceutical compositions containing same and use thereof for treating obesity |
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| EP (1) | EP1328269B2 (sh) |
| JP (1) | JP4221221B2 (sh) |
| KR (1) | KR20030036885A (sh) |
| CN (1) | CN100409845C (sh) |
| AT (1) | ATE267595T1 (sh) |
| AU (2) | AU9393601A (sh) |
| BG (1) | BG107739A (sh) |
| BR (1) | BR0114410A (sh) |
| CA (1) | CA2424934A1 (sh) |
| DE (1) | DE60103556T3 (sh) |
| DK (1) | DK1328269T5 (sh) |
| EA (1) | EA005924B1 (sh) |
| EE (1) | EE200300121A (sh) |
| ES (1) | ES2217191T5 (sh) |
| FR (1) | FR2814678B1 (sh) |
| HR (1) | HRP20030249A2 (sh) |
| HU (1) | HUP0302044A3 (sh) |
| IL (1) | IL155236A0 (sh) |
| MX (1) | MXPA03002845A (sh) |
| NO (1) | NO20031521L (sh) |
| NZ (1) | NZ524904A (sh) |
| PL (1) | PL362833A1 (sh) |
| PT (1) | PT1328269E (sh) |
| SI (1) | SI1328269T2 (sh) |
| SK (1) | SK4032003A3 (sh) |
| TR (1) | TR200401264T4 (sh) |
| WO (1) | WO2002028346A2 (sh) |
| YU (1) | YU26103A (sh) |
| ZA (1) | ZA200303015B (sh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2833842B1 (fr) * | 2001-12-21 | 2004-02-13 | Aventis Pharma Sa | Compositions pharmaceutiques a base de derives d'azetidine |
| CA2478183C (en) | 2002-03-12 | 2010-02-16 | Merck & Co. Inc. | Substituted amides |
| AU2003215024B2 (en) | 2002-03-26 | 2008-02-21 | Merck Sharp & Dohme Corp. | Spirocyclic amides as cannabinoid receptor modulators |
| AU2003225964B2 (en) | 2002-03-28 | 2008-11-20 | Merck Sharp & Dohme Corp. | Substituted 2,3-diphenyl pyridines |
| JP4459629B2 (ja) | 2002-04-12 | 2010-04-28 | メルク エンド カムパニー インコーポレーテッド | 二環式アミド |
| NZ537685A (en) | 2002-07-29 | 2007-06-29 | Hoffmann La Roche | Novel benzodioxoles |
| CA2511905A1 (en) | 2003-01-02 | 2004-07-22 | F. Hoffmann-La Roche Ag | Novel cb 1 receptor inverse agonists |
| RU2339618C2 (ru) | 2003-01-02 | 2008-11-27 | Ф.Хоффманн-Ля Рош Аг | Новые обратные агонисты рецептора св1 |
| US7329658B2 (en) * | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US20040224962A1 (en) * | 2003-05-09 | 2004-11-11 | Pfizer Inc | Pharmaceutical composition for the treatment of obesity or to facilitate or promote weight loss |
| UA83230C2 (ru) | 2003-06-11 | 2008-06-25 | Мерк Энд Ко., Инк. | Замещенные производные 3-алкил- и 3-алкенилазетидинов |
| AU2004251002B2 (en) | 2003-06-20 | 2009-10-29 | F. Hoffmann-La Roche Ag | 2-aminobenzothiazoles as CB1 receptor inverse agonists |
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| 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 |
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