ZA200303015B - 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
- ZA200303015B ZA200303015B ZA200303015A ZA200303015A ZA200303015B ZA 200303015 B ZA200303015 B ZA 200303015B ZA 200303015 A ZA200303015 A ZA 200303015A ZA 200303015 A ZA200303015 A ZA 200303015A ZA 200303015 B ZA200303015 B ZA 200303015B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- chlorophenyl
- bis
- methylsulfonyl
- phenyl
- Prior art date
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- 208000008589 Obesity Diseases 0.000 title description 7
- 235000020824 obesity Nutrition 0.000 title description 7
- 229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 title description 2
- 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 title description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 278
- -1 -COORs Chemical group 0.000 claims description 238
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 185
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 153
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 128
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 99
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 83
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 73
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 34
- 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
- 150000003254 radicals Chemical class 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 239000011593 sulfur Substances 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 28
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 241001484259 Lacuna Species 0.000 claims description 21
- 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 21
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 239000005557 antagonist Substances 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
- 229960004425 sibutramine Drugs 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 17
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 11
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 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
- 125000003118 aryl group Chemical group 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
- 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
- 125000004212 difluorophenyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=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
- 229920006395 saturated elastomer Polymers 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
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 150000002390 heteroarenes Chemical class 0.000 claims description 6
- 150000004702 methyl esters Chemical class 0.000 claims description 6
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-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
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- ZIMKTAJRBXSZIV-UHFFFAOYSA-N 4-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]phenyl]piperazine-1-carboxylic acid Chemical compound C=1C=CC(N2CCN(CC2)C(O)=O)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 ZIMKTAJRBXSZIV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-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
- 239000003085 diluting agent Substances 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 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 3
- DXICLXSALAKMGX-UHFFFAOYSA-N 1-[bis[4-(trifluoromethyl)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(=CC=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 DXICLXSALAKMGX-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
- UYMOXHDJOGNHGD-UHFFFAOYSA-N 2-[(4-chlorophenyl)-[3-[methylsulfonyl(phenyl)methylidene]azetidin-1-yl]methyl]-1,3-thiazole Chemical compound C=1C=CC=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=NC=CS1 UYMOXHDJOGNHGD-UHFFFAOYSA-N 0.000 claims description 3
- NAZAQWONMUGWMU-UHFFFAOYSA-N 2-amino-1-[4-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]phenyl]piperazin-1-yl]ethanone Chemical compound C=1C=CC(N2CCN(CC2)C(=O)CN)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 NAZAQWONMUGWMU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- HVBYMRXIWXCJAR-UHFFFAOYSA-N 4-[(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]benzamide Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(=CC=1)C(N)=O)C1=CC=C(Cl)C=C1 HVBYMRXIWXCJAR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- UHXKSFQELBLXHI-NRFANRHFSA-N FC1=CC(F)=CC(CN(C2CN(C2)[C@@H](C=2C=CC(Cl)=CC=2)C=2C=NC=NC=2)S(=O)=O)=C1 Chemical compound FC1=CC(F)=CC(CN(C2CN(C2)[C@@H](C=2C=CC(Cl)=CC=2)C=2C=NC=NC=2)S(=O)=O)=C1 UHXKSFQELBLXHI-NRFANRHFSA-N 0.000 claims description 3
- UHXKSFQELBLXHI-OAQYLSRUSA-N FC1=CC(F)=CC(CN(C2CN(C2)[C@H](C=2C=CC(Cl)=CC=2)C=2C=NC=NC=2)S(=O)=O)=C1 Chemical compound FC1=CC(F)=CC(CN(C2CN(C2)[C@H](C=2C=CC(Cl)=CC=2)C=2C=NC=NC=2)S(=O)=O)=C1 UHXKSFQELBLXHI-OAQYLSRUSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- IDMCHISNPXIXBA-UHFFFAOYSA-N methyl 4-[[3-acetyloxy-3-[(3,5-difluorophenyl)-methylsulfonylmethyl]azetidin-1-yl]-(4-methoxycarbonylphenyl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(C=1C=CC(=CC=1)C(=O)OC)N1CC(C(C=2C=C(F)C=C(F)C=2)S(C)(=O)=O)(OC(C)=O)C1 IDMCHISNPXIXBA-UHFFFAOYSA-N 0.000 claims description 3
- PGIXKIWCCAODMS-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)-pyridin-3-ylmethyl]azetidin-3-yl]-3,5-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=NC=CC=2)=C1 PGIXKIWCCAODMS-UHFFFAOYSA-N 0.000 claims description 3
- OQOSZSCVVSOVAX-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)-pyrimidin-5-ylmethyl]azetidin-3-yl]-3,5-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=NC=NC=2)=C1 OQOSZSCVVSOVAX-UHFFFAOYSA-N 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 claims description 3
- JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical group CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 claims description 3
- BIHRKCOQNANFPP-UHFFFAOYSA-N 1-[(4-chlorophenyl)-(2,4-dichlorophenyl)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)Cl)C1=CC=C(Cl)C=C1 BIHRKCOQNANFPP-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- PWMHUENFWNXUSI-UHFFFAOYSA-N 1-[4-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]phenyl]piperazin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCN1C1=CC=CC(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 PWMHUENFWNXUSI-UHFFFAOYSA-N 0.000 claims description 2
- ZCBHZANVPPHMRW-UHFFFAOYSA-N 1-[4-[3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=CC(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 ZCBHZANVPPHMRW-UHFFFAOYSA-N 0.000 claims description 2
- ZGLXDYITFVRVCG-UHFFFAOYSA-N 1-[[4-[(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]pyrrolidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(CN2CCCC2)=CC=1)C1=CC=C(Cl)C=C1 ZGLXDYITFVRVCG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 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 2
- 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 2
- FKKHCIPUNAWTLT-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-2-methylphenol Chemical compound CC1=C(O)C=CC=C1C(S(C)(=O)=O)=C1CN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C1 FKKHCIPUNAWTLT-UHFFFAOYSA-N 0.000 claims description 2
- YHLBBKRNEGXKNL-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(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 YHLBBKRNEGXKNL-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- QBXYOSLUFLDMRF-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-(2-phenylpropyl)benzamide Chemical compound C=1C=CC=CC=1C(C)CNC(=O)C(C=1)=CC=CC=1C(S(C)(=O)=O)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 QBXYOSLUFLDMRF-UHFFFAOYSA-N 0.000 claims description 2
- LRDRFHMXIBTQOL-UHFFFAOYSA-N 3-[[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-methylsulfonylmethyl]-n-(cyclohexylmethyl)benzamide Chemical compound C=1C=CC(C(=O)NCC2CCCCC2)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LRDRFHMXIBTQOL-UHFFFAOYSA-N 0.000 claims description 2
- ADYFILJCNRRPGL-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(C(=C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(C)(=O)=O)=C1 ADYFILJCNRRPGL-UHFFFAOYSA-N 0.000 claims description 2
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- JCIXVVKUDFFJAG-HHHXNRCGSA-N 1-[[4-[(r)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]imidazole Chemical compound C1([C@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CN3C=NC=C3)=CC=2)=CC=C(Cl)C=C1 JCIXVVKUDFFJAG-HHHXNRCGSA-N 0.000 claims 1
- JCIXVVKUDFFJAG-MHZLTWQESA-N 1-[[4-[(s)-(4-chlorophenyl)-[3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidin-1-yl]methyl]phenyl]methyl]imidazole Chemical compound C1([C@@H](N2CC(C2)=C(S(=O)(=O)C)C=2C=C(F)C=C(F)C=2)C=2C=CC(CN3C=NC=C3)=CC=2)=CC=C(Cl)C=C1 JCIXVVKUDFFJAG-MHZLTWQESA-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
- HTAFPFCNDMXLIB-UHFFFAOYSA-N 1-benzhydryl-3-[methylsulfonylmethylsulfonyl(naphthalen-1-yl)methylidene]azetidine Chemical compound C=1C=CC2=CC=CC=C2C=1C(S(=O)(=O)CS(=O)(=O)C)=C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HTAFPFCNDMXLIB-UHFFFAOYSA-N 0.000 claims 1
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- 239000010452 phosphate Substances 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
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- 150000003217 pyrazoles Chemical class 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 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
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- 229940095064 tartrate Drugs 0.000 description 1
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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)
- 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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303015B true ZA200303015B (en) | 2004-02-26 |
Family
ID=8854974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303015A ZA200303015B (en) | 2000-10-04 | 2003-04-16 | Association of the CB1 receptor antagonist and sibutramin, for treating obesity. |
Country Status (29)
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| EP (1) | EP1328269B2 (sk) |
| JP (1) | JP4221221B2 (sk) |
| KR (1) | KR20030036885A (sk) |
| CN (1) | CN100409845C (sk) |
| AT (1) | ATE267595T1 (sk) |
| AU (2) | AU2001293936B2 (sk) |
| BG (1) | BG107739A (sk) |
| BR (1) | BR0114410A (sk) |
| CA (1) | CA2424934A1 (sk) |
| DE (1) | DE60103556T3 (sk) |
| DK (1) | DK1328269T5 (sk) |
| EA (1) | EA005924B1 (sk) |
| EE (1) | EE200300121A (sk) |
| ES (1) | ES2217191T5 (sk) |
| FR (1) | FR2814678B1 (sk) |
| HR (1) | HRP20030249A2 (sk) |
| HU (1) | HUP0302044A3 (sk) |
| IL (1) | IL155236A0 (sk) |
| MX (1) | MXPA03002845A (sk) |
| NO (1) | NO20031521L (sk) |
| NZ (1) | NZ524904A (sk) |
| PL (1) | PL362833A1 (sk) |
| PT (1) | PT1328269E (sk) |
| SI (1) | SI1328269T2 (sk) |
| SK (1) | SK4032003A3 (sk) |
| TR (1) | TR200401264T4 (sk) |
| WO (1) | WO2002028346A2 (sk) |
| YU (1) | YU26103A (sk) |
| ZA (1) | ZA200303015B (sk) |
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 |
| EP1496838B1 (en) | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Substituted amides |
| WO2003082190A2 (en) | 2002-03-26 | 2003-10-09 | Merck & Co., Inc. | Spirocyclic amides as cannabinoid receptor modulators |
| WO2003082191A2 (en) | 2002-03-28 | 2003-10-09 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
| CA2481313A1 (en) | 2002-04-12 | 2003-10-23 | Merck & Co., Inc. | Bicyclic amides |
| RU2304580C2 (ru) | 2002-07-29 | 2007-08-20 | Ф.Хоффманн-Ля Рош Аг | Новые бензодиоксолы |
| PL378244A1 (pl) | 2003-01-02 | 2006-03-20 | F. Hoffmann-La Roche Ag | Pirolilotiazole i ich zastosowanie jako odwrotnych agonistów receptora CB 1 |
| WO2004060870A1 (en) | 2003-01-02 | 2004-07-22 | F. Hoffmann-La Roche Ag | Novel cb 1 receptour inverse agonists |
| 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 |
| US7485732B2 (en) | 2003-06-11 | 2009-02-03 | Merck & Co., Inc. | Substituted 3-alkyl and 3-alkenyl azetidine derivatives |
| ES2303077T3 (es) | 2003-06-20 | 2008-08-01 | F. Hoffmann-La Roche Ag | 2-aminobenzotiazoles como agonistas inversos del receptor de cb1. |
| 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 |
| EP1663215A1 (en) * | 2003-09-02 | 2006-06-07 | 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 |
| CN100509808C (zh) | 2003-12-08 | 2009-07-08 | 霍夫曼-拉罗奇有限公司 | 新型噻唑衍生物 |
| EP1716132B1 (en) | 2004-01-28 | 2010-08-25 | F. Hoffmann-La Roche AG | Spiro-benzodioxoles and their use as cb1 antagonists |
| JP2007536298A (ja) | 2004-05-10 | 2007-12-13 | エフ．ホフマン−ラ ロシュ アーゲー | 肥満を処置するためのピロールまたはイミダゾールアミド |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| WO2006039334A1 (en) * | 2004-09-29 | 2006-04-13 | Schering Corporation | Combinations of substituted azetidonones and cb1 antagonists |
| 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 |
| CA2585175A1 (en) | 2004-10-25 | 2006-05-04 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising cb1 cannabinoid receptor antagonists and potassium channel openers for the treatment of diabetes mellitus type i, obesity and related conditions |
| ES2309812T3 (es) | 2004-10-27 | 2008-12-16 | F. Hoffmann-La Roche Ag | Nuevos derivados de indol o benzimidazol. |
| EP1812418B1 (en) | 2004-11-09 | 2010-10-27 | F. Hoffmann-La Roche AG | Dibenzosuberone derivatives |
| DE602006007563D1 (de) | 2005-04-06 | 2009-08-13 | Hoffmann La Roche | Agonisten |
| US7906652B2 (en) | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| US20080027087A1 (en) * | 2006-02-21 | 2008-01-31 | 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 |
| WO2007118854A1 (en) | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and the use thereof |
| US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| 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 |
| WO2008026219A2 (en) * | 2006-09-01 | 2008-03-06 | Hetero Drugs Limited | Novel polymorphs of rimonabant |
| US7781593B2 (en) | 2006-09-14 | 2010-08-24 | Hoffmann-La Roche Inc. | 5-phenyl-nicotinamide derivatives |
| CA2664310A1 (en) * | 2006-09-25 | 2008-04-03 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| 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 |
| WO2008124118A1 (en) | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use therof |
| US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| EA019315B1 (ru) * | 2007-12-18 | 2014-02-28 | Санофи-Авентис | Производные азетидинов, их получение и применение в терапии |
| 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 |
| GB2343550A (en) * | 1997-07-29 | 2000-05-10 | Silicon Genesis Corp | Cluster tool method and apparatus 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 CN CNB018182682A patent/CN100409845C/zh not_active Expired - Fee Related
- 2001-10-01 EE EEP200300121A patent/EE200300121A/xx unknown
- 2001-10-01 IL IL15523601A patent/IL155236A0/xx unknown
- 2001-10-01 PT PT01974413T patent/PT1328269E/pt unknown
- 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 AU AU2001293936A patent/AU2001293936B2/en not_active Ceased
- 2001-10-01 DK DK01974413T patent/DK1328269T5/da active
- 2001-10-01 TR TR2004/01264T patent/TR200401264T4/xx unknown
- 2001-10-01 HU HU0302044A patent/HUP0302044A3/hu unknown
- 2001-10-01 BR BR0114410-3A patent/BR0114410A/pt not_active IP Right Cessation
- 2001-10-01 SK SK403-2003A patent/SK4032003A3/sk not_active Application Discontinuation
- 2001-10-01 CA CA002424934A patent/CA2424934A1/fr not_active Abandoned
- 2001-10-01 WO PCT/FR2001/003022 patent/WO2002028346A2/fr active IP Right Grant
- 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 EP EP01974413A patent/EP1328269B2/fr not_active Expired - Lifetime
- 2001-10-01 ES ES01974413T patent/ES2217191T5/es not_active Expired - Lifetime
- 2001-10-01 AT AT01974413T patent/ATE267595T1/de not_active IP Right Cessation
- 2001-10-01 AU AU9393601A patent/AU9393601A/xx active Pending
- 2001-10-01 DE DE60103556T patent/DE60103556T3/de not_active Expired - Lifetime
- 2001-10-01 NZ NZ524904A patent/NZ524904A/en unknown
- 2001-10-01 SI SI200130139T patent/SI1328269T2/sl unknown
- 2001-10-01 YU YU26103A patent/YU26103A/sh unknown
- 2001-10-01 KR KR10-2003-7004772A patent/KR20030036885A/ko not_active Application Discontinuation
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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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