SK4032003A3 - Association of the CB1 receptor antagonist and sibutramin, for treating obesity - Google Patents
Association of the CB1 receptor antagonist and sibutramin, for treating obesity Download PDFInfo
- Publication number
- SK4032003A3 SK4032003A3 SK403-2003A SK4032003A SK4032003A3 SK 4032003 A3 SK4032003 A3 SK 4032003A3 SK 4032003 A SK4032003 A SK 4032003A SK 4032003 A3 SK4032003 A3 SK 4032003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- chlorophenyl
- bis
- methylsulfonyl
- azetidine
- Prior art date
Links
- 208000008589 Obesity Diseases 0.000 title abstract description 8
- 235000020824 obesity Nutrition 0.000 title abstract description 8
- 229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 title abstract description 6
- 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 title abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 289
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 270
- -1 -COOR 5 Chemical group 0.000 claims description 215
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 128
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 72
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 67
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 61
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 60
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 239000011593 sulfur Chemical group 0.000 claims description 28
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 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 22
- 229960004425 sibutramine Drugs 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 229940124802 CB1 antagonist Drugs 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 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
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 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
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 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 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000002950 monocyclic 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-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
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- VKYOAPIHWDRWCF-VWLOTQADSA-N 4-[(s)-(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-VWLOTQADSA-N 0.000 claims description 5
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 5
- BIHRKCOQNANFPP-QHCPKHFHSA-N 1-[(s)-(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-QHCPKHFHSA-N 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 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
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 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
- SBNQHGQKWYWGIE-UHFFFAOYSA-N 1-[4-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]phenyl]piperazin-1-yl]-2-(methylamino)ethanone Chemical compound C1CN(C(=O)CNC)CCN1C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 SBNQHGQKWYWGIE-UHFFFAOYSA-N 0.000 claims description 3
- WKOAOEVZSBATJT-SSEXGKCCSA-N 1-[[4-[(r)-(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-SSEXGKCCSA-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
- NUBHCVLRJBDQQR-UHFFFAOYSA-N 1-[bis(4-methylphenyl)methyl]-3-[methylsulfonyl(phenyl)methylidene]azetidine Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC=CC=C1 NUBHCVLRJBDQQR-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
- 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
- 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
- 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
- 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 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
- 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
- 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
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 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
- HVBYMRXIWXCJAR-HSZRJFAPSA-N 4-[(r)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]benzamide Chemical compound C1([C@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(=CC=2)C(N)=O)=CC=C(Cl)C=C1 HVBYMRXIWXCJAR-HSZRJFAPSA-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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- WXNMZJIASLWWFS-UHFFFAOYSA-N C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC(N(CC=2C=C3C=CC=NC3=CC=2)S(=O)=O)C1 Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC(N(CC=2C=C3C=CC=NC3=CC=2)S(=O)=O)C1 WXNMZJIASLWWFS-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
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- NJUQAIXQRRQGRJ-UHFFFAOYSA-N 1-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]phenyl]-4-(2-methylpropyl)piperazine Chemical compound C1CN(CC(C)C)CCN1C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 NJUQAIXQRRQGRJ-UHFFFAOYSA-N 0.000 claims 1
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- FBWVTEZCNIQJRF-UHFFFAOYSA-N 1-[[4-[(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=C(C(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-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
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- OQODAQPQMPMKFB-UHFFFAOYSA-N 4-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]methylsulfonylmethyl]phenyl]-n-methylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NC)CCN1C1=CC=CC(CS(=O)(=O)C=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 OQODAQPQMPMKFB-UHFFFAOYSA-N 0.000 claims 1
- OIJLKMYMEOURJA-UHFFFAOYSA-N 4-[[4-[(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]morpholine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(CN2CCOCC2)=CC=1)C1=CC=C(Cl)C=C1 OIJLKMYMEOURJA-UHFFFAOYSA-N 0.000 claims 1
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- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
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- 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 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- 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 1
- XZLPOJOSMALGTC-QUZZAMIASA-N n-[(1s,3s,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-QUZZAMIASA-N 0.000 claims 1
- 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 1
- 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 1
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- QGEIDYNVEYDOHV-UHFFFAOYSA-N n-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-n-methylquinoline-8-sulfonamide Chemical compound C=1C=CC2=CC=CN=C2C=1S(=O)(=O)N(C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 QGEIDYNVEYDOHV-UHFFFAOYSA-N 0.000 claims 1
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- ZVCQSDQDTCYOGI-UHFFFAOYSA-N n-[[4-[(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]-n-propan-2-ylpropan-2-amine Chemical compound C1=CC(CN(C(C)C)C(C)C)=CC=C1C(C=1C=CC(Cl)=CC=1)N(C1)CC1=C(S(C)(=O)=O)C1=CC(F)=CC(F)=C1 ZVCQSDQDTCYOGI-UHFFFAOYSA-N 0.000 claims 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011680 zucker rat Methods 0.000 description 1
Classifications
-
- 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)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (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 |
|---|---|
| SK4032003A3 true SK4032003A3 (en) | 2003-09-11 |
Family
ID=8854974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK403-2003A SK4032003A3 (en) | 2000-10-04 | 2001-10-01 | Association of the CB1 receptor antagonist and sibutramin, for treating obesity |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP1328269B2 (ja) |
| JP (1) | JP4221221B2 (ja) |
| KR (1) | KR20030036885A (ja) |
| CN (1) | CN100409845C (ja) |
| AT (1) | ATE267595T1 (ja) |
| AU (2) | AU2001293936B2 (ja) |
| BG (1) | BG107739A (ja) |
| BR (1) | BR0114410A (ja) |
| CA (1) | CA2424934A1 (ja) |
| DE (1) | DE60103556T3 (ja) |
| DK (1) | DK1328269T5 (ja) |
| EA (1) | EA005924B1 (ja) |
| EE (1) | EE200300121A (ja) |
| ES (1) | ES2217191T5 (ja) |
| FR (1) | FR2814678B1 (ja) |
| HR (1) | HRP20030249A2 (ja) |
| HU (1) | HUP0302044A3 (ja) |
| IL (1) | IL155236A0 (ja) |
| MX (1) | MXPA03002845A (ja) |
| NO (1) | NO20031521L (ja) |
| NZ (1) | NZ524904A (ja) |
| PL (1) | PL362833A1 (ja) |
| PT (1) | PT1328269E (ja) |
| SI (1) | SI1328269T2 (ja) |
| SK (1) | SK4032003A3 (ja) |
| TR (1) | TR200401264T4 (ja) |
| WO (1) | WO2002028346A2 (ja) |
| YU (1) | YU26103A (ja) |
| ZA (1) | ZA200303015B (ja) |
Families Citing this family (46)
| 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 |
| NZ534757A (en) | 2002-03-12 | 2006-07-28 | Merck & Co Inc | Substituted amides |
| AU2003215024B2 (en) | 2002-03-26 | 2008-02-21 | Merck Sharp & Dohme Corp. | Spirocyclic amides as cannabinoid receptor modulators |
| US7271266B2 (en) | 2002-03-28 | 2007-09-18 | Merck & Co., Inc. | 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 |
| EP1532132B1 (en) | 2002-07-29 | 2008-03-19 | F.Hoffmann-La Roche Ag | Novel benzodioxoles |
| MXPA05007114A (es) | 2003-01-02 | 2005-08-26 | Hoffmann La Roche | Nuevos agonistas inversos del receptor cb1. |
| JP4271660B2 (ja) | 2003-01-02 | 2009-06-03 | エフ．ホフマン−ラ ロシュ アーゲー | ピロリル−チアゾール及びｃｂ１受容体逆作動物質としてのその使用 |
| 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 |
| CN1802351A (zh) | 2003-06-11 | 2006-07-12 | 麦克公司 | 被取代的3－烷基和3－链烯基氮杂环丁烷衍生物 |
| EP1638556B1 (en) | 2003-06-20 | 2008-04-02 | F. Hoffmann-La Roche Ag | 2-aminobenzothiazoles as cb1 receptor inverse agonists |
| EP1498123A1 (en) * | 2003-07-18 | 2005-01-19 | Aventis Pharma S.A. | Emulsifying systems containing azetidine derivatives |
| EP1498122A1 (en) * | 2003-07-18 | 2005-01-19 | Aventis Pharma S.A. | Semi-solid systems containing azetidine derivatives |
| WO2005020992A1 (en) * | 2003-09-02 | 2005-03-10 | Solvay Pharmaceuticals Gmbh | Novel medical use of selective cb1-receptor antagonists |
| FR2861303A1 (fr) * | 2003-10-24 | 2005-04-29 | Sanofi Synthelabo | Utilisation d'un derive de pyrazole pour la preparation de medicaments utiles dans la prevention et le traitement du syndrome metabolique |
| WO2005049615A1 (en) * | 2003-11-21 | 2005-06-02 | Pfizer Products Inc. | Pyrazolo`1,5-a!`1,3,5! triazin -4-one derivatives as cb1 receptor antagonists |
| JP4527729B2 (ja) | 2003-12-08 | 2010-08-18 | エフ．ホフマン−ラ ロシュ アーゲー | 新規チアゾール誘導体 |
| KR100843023B1 (ko) | 2004-01-28 | 2008-07-01 | 에프. 호프만-라 로슈 아게 | 스피로-5환 화합물 |
| CA2564986A1 (en) | 2004-05-10 | 2005-11-17 | F. Hoffmann-La Roche Ag | Pyrrole or imidazole amides for treating obesity |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| JP2008514718A (ja) * | 2004-09-29 | 2008-05-08 | シェーリング コーポレイション | 置換アゼチドノンおよびｃｂ１アンタゴニストの組み合わせ |
| FR2876689B1 (fr) | 2004-10-14 | 2008-02-22 | Aventis Pharma Sa | Nouveau procede et intermediaires de preparation de derives de n-(1-benzhydryl-azetidin-3-yl)-n-phenyl-methylsulfonamide |
| MX2007004889A (es) | 2004-10-25 | 2007-09-11 | Solvay Pharm Gmbh | Composiciones farmaceuticas que comprenden antagonistas del receptor cannabinoide cb1 y activadores de canales de potasio para el tratamiento de la diabetes mellitus tipo i, la obesidad y trastornos relacionados. |
| KR100912146B1 (ko) | 2004-10-27 | 2009-08-14 | 에프. 호프만-라 로슈 아게 | 인돌 또는 벤즈이미다졸 유도체 |
| EP1812418B1 (en) | 2004-11-09 | 2010-10-27 | F. Hoffmann-La Roche AG | Dibenzosuberone derivatives |
| WO2006106054A1 (en) | 2005-04-06 | 2006-10-12 | F. Hoffmann-La Roche Ag | Pyridine-3-carboxamide derivatives as cb1 inverse agonists |
| US7906652B2 (en) | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| EP1986638A2 (en) * | 2006-02-21 | 2008-11-05 | Ampla Pharmaceuticals Inc. | Cb1 antagonists and inverse agonists |
| WO2007110449A1 (en) * | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| TW200812963A (en) | 2006-04-13 | 2008-03-16 | Euro Celtique Sa | Benzenesulfonamide compounds and the use thereof |
| TW200815353A (en) | 2006-04-13 | 2008-04-01 | Euro Celtique Sa | Benzenesulfonamide compounds and their use |
| US7629346B2 (en) | 2006-06-19 | 2009-12-08 | Hoffmann-La Roche Inc. | Pyrazinecarboxamide derivatives as CB1 antagonists |
| WO2008038143A2 (en) * | 2006-06-22 | 2008-04-03 | Medichem, S.A. | Novel solid forms of rimonabant and synthetic processes for their preparation |
| US20100076022A1 (en) * | 2006-09-01 | 2010-03-25 | Hetero Drugs Limited | Novel polymorphs of rimonabant |
| US7781593B2 (en) | 2006-09-14 | 2010-08-24 | Hoffmann-La Roche Inc. | 5-phenyl-nicotinamide derivatives |
| CN101516839A (zh) * | 2006-09-25 | 2009-08-26 | 贝林格尔.英格海姆国际有限公司 | 调节cb2受体的化合物 |
| DE102007002260A1 (de) | 2007-01-16 | 2008-07-31 | Sanofi-Aventis | Verwendung von substituierten Pyranonsäurederivaten zur Herstellung von Medikamenten zur Behandlung des Metabolischen Syndroms |
| EP1953144A1 (en) * | 2007-01-30 | 2008-08-06 | Sandoz AG | Novel polymorphic forms of N-piperidino-5-(4-chlorophenyl)-1-(2, 4-dichlorphenyl)-4-methyl-3-pyrazolecarboxamide |
| US8399486B2 (en) | 2007-04-09 | 2013-03-19 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use thereof |
| US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| SI2234966T1 (sl) * | 2007-12-18 | 2014-01-31 | Sanofi | Derivati azetidinov, njihova priprava in njihova terapevtska uporaba |
| WO2010079241A1 (es) | 2009-01-12 | 2010-07-15 | Fundacion Hospital Nacional De Paraplejicos Para La Investigacion Y La Integracion | Uso de antagonistas y/o agonistas inversos de los receptores cb1 para la preparación de medicamentos que incrementen la excitabilidad de las motoneuronas |
| BRPI0902481B8 (pt) | 2009-07-31 | 2021-05-25 | Soc Beneficente De Senhoras Hospital Sirio Libanes | composição farmacêutica compreendendo hemopressina e seu uso. |
| US8410107B2 (en) | 2010-10-15 | 2013-04-02 | Hoffmann-La Roche Inc. | N-pyridin-3-yl or N-pyrazin-2-yl carboxamides |
| US8669254B2 (en) | 2010-12-15 | 2014-03-11 | Hoffman-La Roche Inc. | Pyridine, pyridazine, pyrimidine or pyrazine carboxamides as HDL-cholesterol raising agents |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE61928B1 (en) † | 1988-11-29 | 1994-11-30 | Boots Co Plc | Treatment of obesity |
| JPH04360167A (ja) * | 1991-06-06 | 1992-12-14 | Mitsubishi Kasei Corp | 近接帯電装置 |
| FR2713225B1 (fr) † | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
| JPH07209959A (ja) * | 1994-01-24 | 1995-08-11 | Ricoh Co Ltd | 帯電装置 |
| US5596106A (en) † | 1994-07-15 | 1997-01-21 | Eli Lilly And Company | Cannabinoid receptor antagonists |
| FR2735774B1 (fr) * | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| US6482927B1 (en) * | 1995-11-27 | 2002-11-19 | Millennium Pharmaceuticals, Inc. | Chimeric proteins comprising the extracellular domain of murine Ob receptor |
| GB9619961D0 (en) * | 1996-09-25 | 1996-11-13 | Knoll Ag | Medical treatment |
| JP2002516605A (ja) † | 1996-10-31 | 2002-06-04 | メルク エンド カンパニー インコーポレーテッド | 糖尿病および肥満の治療のための併用療法 |
| FR2758723B1 (fr) * | 1997-01-28 | 1999-04-23 | Sanofi Sa | Utilisation des antagonistes des recepteurs aux cannabinoides centraux pour la preparation de medicaments |
| US6321134B1 (en) * | 1997-07-29 | 2001-11-20 | Silicon Genesis Corporation | Clustertool system software using plasma immersion ion implantation |
| EP0920864A1 (en) † | 1997-12-03 | 1999-06-09 | Pfizer Products Inc. | Combination therapy including a specific beta-3 agonist and an anorectic agent |
| FR2783246B1 (fr) * | 1998-09-11 | 2000-11-17 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les medicaments les contenant |
| KR100652994B1 (ko) † | 1998-09-11 | 2006-11-30 | 아방티 파르마 소시에테 아노님 | 아제티딘 유도체, 이의 제조방법 및 이를 함유하는 약제 |
| 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 |
| 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 |
-
2000
- 2000-10-04 FR FR0012646A patent/FR2814678B1/fr not_active Expired - Fee Related
-
2001
- 2001-10-01 BR BR0114410-3A patent/BR0114410A/pt not_active IP Right Cessation
- 2001-10-01 EE EEP200300121A patent/EE200300121A/xx unknown
- 2001-10-01 SI SI200130139T patent/SI1328269T2/sl unknown
- 2001-10-01 ES ES01974413T patent/ES2217191T5/es not_active Expired - Lifetime
- 2001-10-01 MX MXPA03002845A patent/MXPA03002845A/es active IP Right Grant
- 2001-10-01 EA EA200300441A patent/EA005924B1/ru not_active IP Right Cessation
- 2001-10-01 WO PCT/FR2001/003022 patent/WO2002028346A2/fr active IP Right Grant
- 2001-10-01 JP JP2002531972A patent/JP4221221B2/ja not_active Expired - Fee Related
- 2001-10-01 PL PL01362833A patent/PL362833A1/xx not_active Application Discontinuation
- 2001-10-01 DE DE60103556T patent/DE60103556T3/de not_active Expired - Lifetime
- 2001-10-01 KR KR10-2003-7004772A patent/KR20030036885A/ko not_active Application Discontinuation
- 2001-10-01 IL IL15523601A patent/IL155236A0/xx unknown
- 2001-10-01 DK DK01974413T patent/DK1328269T5/da active
- 2001-10-01 TR TR2004/01264T patent/TR200401264T4/xx unknown
- 2001-10-01 AU AU2001293936A patent/AU2001293936B2/en not_active Ceased
- 2001-10-01 HU HU0302044A patent/HUP0302044A3/hu unknown
- 2001-10-01 CN CNB018182682A patent/CN100409845C/zh not_active Expired - Fee Related
- 2001-10-01 NZ NZ524904A patent/NZ524904A/en unknown
- 2001-10-01 SK SK403-2003A patent/SK4032003A3/sk not_active Application Discontinuation
- 2001-10-01 PT PT01974413T patent/PT1328269E/pt unknown
- 2001-10-01 YU YU26103A patent/YU26103A/sh unknown
- 2001-10-01 AU AU9393601A patent/AU9393601A/xx active Pending
- 2001-10-01 AT AT01974413T patent/ATE267595T1/de not_active IP Right Cessation
- 2001-10-01 CA CA002424934A patent/CA2424934A1/fr not_active Abandoned
- 2001-10-01 EP EP01974413A patent/EP1328269B2/fr not_active Expired - Lifetime
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2003
- 2003-04-02 HR HR20030249A patent/HRP20030249A2/hr not_active Application Discontinuation
- 2003-04-03 NO NO20031521A patent/NO20031521L/no not_active Application Discontinuation
- 2003-04-16 ZA ZA200303015A patent/ZA200303015B/en unknown
- 2003-04-17 BG BG107739A patent/BG107739A/bg unknown
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