SK3812003A3 - New thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors - Google Patents

New thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors Download PDF

Info

Publication number: SK3812003A3
Authority: SK; Slovakia
Prior art keywords: methyl; thiadiazol; group; dihydro; cyclohexylimino
Prior art date: 2000-10-02

Application number

SK381-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Fabrice Vergne

Pierre Ducrot

Charles Andrianjara

Patrick Bernardelli

Edwige Lorthiois

Original Assignee

Warner Lambert Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-10-02

Filing date

2001-10-01

Publication date

2004-05-04

2001-10-01 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2004-05-04 Publication of SK3812003A3 publication Critical patent/SK3812003A3/sk

Links

239000002606 phosphodiesterase VII inhibitor Substances 0.000 title claims abstract description 13
150000004867 thiadiazoles Chemical class 0.000 title claims description 5
150000004866 oxadiazoles Chemical class 0.000 title description 3
238000000034 method Methods 0.000 claims abstract description 207
125000000217 alkyl group Chemical group 0.000 claims abstract description 68
125000003118 aryl group Chemical group 0.000 claims abstract description 33
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 26
125000003367 polycyclic group Chemical group 0.000 claims abstract description 26
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 17
229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 claims abstract description 9
230000008569 process Effects 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract 2
-1 triazol-3-ylimino Chemical group 0.000 claims description 494
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 329
150000001875 compounds Chemical class 0.000 claims description 288
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 179
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 114
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 83
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 73
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 61
125000000623 heterocyclic group Chemical group 0.000 claims description 61
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 60
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 60
239000005711 Benzoic acid Substances 0.000 claims description 52
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 48
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 45
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
150000001412 amines Chemical class 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 36
235000010233 benzoic acid Nutrition 0.000 claims description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 25
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
125000002947 alkylene group Chemical group 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
125000005843 halogen group Chemical group 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
125000004430 oxygen atom Chemical group O* 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 20
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 20
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 17
125000004434 sulfur atom Chemical group 0.000 claims description 14
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 12
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
208000030507 AIDS Diseases 0.000 claims description 9
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 9
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
125000000732 arylene group Chemical group 0.000 claims description 8
125000002619 bicyclic group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000002993 cycloalkylene group Chemical group 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
150000003583 thiosemicarbazides Chemical class 0.000 claims description 8
101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 7
150000001263 acyl chlorides Chemical class 0.000 claims description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
150000002429 hydrazines Chemical class 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
BOWYQHCFTNADQJ-UHFFFAOYSA-N OC1=CN=NO1 Chemical compound OC1=CN=NO1 BOWYQHCFTNADQJ-UHFFFAOYSA-N 0.000 claims description 6
210000001744 T-lymphocyte Anatomy 0.000 claims description 6
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
229960001867 guaiacol Drugs 0.000 claims description 6
208000027866 inflammatory disease Diseases 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 5
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 5
208000023504 respiratory system disease Diseases 0.000 claims description 5
229960004889 salicylic acid Drugs 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
208000023275 Autoimmune disease Diseases 0.000 claims description 4
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
208000016222 Pancreatic disease Diseases 0.000 claims description 4
208000026935 allergic disease Diseases 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
230000002124 endocrine Effects 0.000 claims description 4
150000002540 isothiocyanates Chemical class 0.000 claims description 4
201000006417 multiple sclerosis Diseases 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
208000024691 pancreas disease Diseases 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
208000009935 visceral pain Diseases 0.000 claims description 4
SKISLNVJHACVTH-UHFFFAOYSA-N 2-[3-(dimethylamino)-3-hydroxypropyl]-N-ethylbenzenesulfonamide Chemical compound CN(C)C(CCC1=C(C=CC=C1)S(=O)(=O)NCC)O SKISLNVJHACVTH-UHFFFAOYSA-N 0.000 claims description 3
ICVKYWHJIBOFLA-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n,n-diethylbenzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N(CC)CC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 ICVKYWHJIBOFLA-UHFFFAOYSA-N 0.000 claims description 3
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
USLFVLJACFGLRO-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]phenol Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC(O)=C1 USLFVLJACFGLRO-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
UEGJNPXVRIZMIZ-UHFFFAOYSA-N 4-[5-(3,3-difluorocyclohexyl)imino-4-methyl-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1CCCC(F)(F)C1 UEGJNPXVRIZMIZ-UHFFFAOYSA-N 0.000 claims description 3
WIQKUJASFBFQQE-UHFFFAOYSA-N 4-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]cyclohexan-1-amine Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1CCC(N)CC1 WIQKUJASFBFQQE-UHFFFAOYSA-N 0.000 claims description 3
JVMJCWANJXNDNJ-UHFFFAOYSA-N 4-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]phenol Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=C(O)C=C1 JVMJCWANJXNDNJ-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
DTOXRIDDHGRZGL-UHFFFAOYSA-N 5-[4-chloro-3-(4-methylpiperazin-1-yl)sulfonylphenyl]-n-cyclohexyl-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=CC=C1Cl DTOXRIDDHGRZGL-UHFFFAOYSA-N 0.000 claims description 3
DYQQZSOTLIPYBH-NNUKFRKNSA-N C1C[C@@H](C)CC[C@@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 Chemical compound C1C[C@@H](C)CC[C@@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 DYQQZSOTLIPYBH-NNUKFRKNSA-N 0.000 claims description 3
DYQQZSOTLIPYBH-JNSHFYNHSA-N C1C[C@@H](C)CC[C@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 Chemical compound C1C[C@@H](C)CC[C@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 DYQQZSOTLIPYBH-JNSHFYNHSA-N 0.000 claims description 3
ZDVSFIAHGGFEGM-HDJSIYSDSA-N CN1N=C(C=2C=CC(=CC=2)C#N)SC1=N[C@H]1CC[C@H](O)CC1 Chemical compound CN1N=C(C=2C=CC(=CC=2)C#N)SC1=N[C@H]1CC[C@H](O)CC1 ZDVSFIAHGGFEGM-HDJSIYSDSA-N 0.000 claims description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
208000015114 central nervous system disease Diseases 0.000 claims description 3
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 3
150000004702 methyl esters Chemical class 0.000 claims description 3
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 3
229960000581 salicylamide Drugs 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
NZGADERMYAURIO-NSHDSACASA-N (2s)-2-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]butan-1-ol Chemical compound CN1C(=N[C@H](CO)CC)SC(C=2C=CC(Cl)=CC=2)=N1 NZGADERMYAURIO-NSHDSACASA-N 0.000 claims description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
SIYBWQRWGWUIRN-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-2-methylpropan-1-ol Chemical compound S1C(=NC(C)(C)CO)N(C)N=C1C1=CC=C(Cl)C=C1 SIYBWQRWGWUIRN-UHFFFAOYSA-N 0.000 claims description 2
DNQANHIDFUSEAV-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]cyclohexan-1-amine Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1CCCCC1N DNQANHIDFUSEAV-UHFFFAOYSA-N 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
OTGRFAYZICXAOC-UHFFFAOYSA-N 2-fluoro-5-[[3-methyl-5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-ylidene]amino]benzoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)S(C)(=O)=O)SC1=NC1=CC=C(F)C(C(O)=O)=C1 OTGRFAYZICXAOC-UHFFFAOYSA-N 0.000 claims description 2
JXLBVTSKHSZDRR-UHFFFAOYSA-N 3-[[5-(4-acetamidophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1C(S1)=NN(C)C1=NC1=CC=CC(C(O)=O)=C1 JXLBVTSKHSZDRR-UHFFFAOYSA-N 0.000 claims description 2
MWDFCYBLSGQXOU-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-2,5,6-trifluorobenzoic acid Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC(F)=C(F)C(C(O)=O)=C1F MWDFCYBLSGQXOU-UHFFFAOYSA-N 0.000 claims description 2
UXPHWRMTFNAKEB-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-n'-hydroxybenzenecarboximidamide Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC(C(=N)NO)=C1 UXPHWRMTFNAKEB-UHFFFAOYSA-N 0.000 claims description 2
LMSSHPYDUCJDQL-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]azepan-2-one Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1CCCCNC1=O LMSSHPYDUCJDQL-UHFFFAOYSA-N 0.000 claims description 2
FPBYAAMXDNYNQB-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzonitrile Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC(C#N)=C1 FPBYAAMXDNYNQB-UHFFFAOYSA-N 0.000 claims description 2
GVVFNEXWSYGWBJ-UHFFFAOYSA-N 3-[n-amino-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)anilino]-n,n-dimethyl-4-nitrobut-3-en-1-amine Chemical compound C1=CC(N(N)C(=C[N+]([O-])=O)CCN(C)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 GVVFNEXWSYGWBJ-UHFFFAOYSA-N 0.000 claims description 2
ULTYLDKYYJFVIP-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2-methylpropyl)benzamide Chemical compound C1=CC(C(=O)NCC(C)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 ULTYLDKYYJFVIP-UHFFFAOYSA-N 0.000 claims description 2
IHXREKDDXUEARQ-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(pyridin-3-ylmethyl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)SC1=NC1CCCCC1 IHXREKDDXUEARQ-UHFFFAOYSA-N 0.000 claims description 2
OBMUEOFVKJCUBT-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-[2-(dimethylamino)ethyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)N(C)CCN(C)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 OBMUEOFVKJCUBT-UHFFFAOYSA-N 0.000 claims description 2
UHQBOURKAHJZRS-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 UHQBOURKAHJZRS-UHFFFAOYSA-N 0.000 claims description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
LQYZIMHRPAYWSO-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-cyclohexyl-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C=C(Cl)C=CC=2)SC1=NC1CCCCC1 LQYZIMHRPAYWSO-UHFFFAOYSA-N 0.000 claims description 2
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BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
UQJLSMYQBOJUGG-UHFFFAOYSA-N tert-butyl 2,2,2-trifluoroacetate Chemical compound CC(C)(C)OC(=O)C(F)(F)F UQJLSMYQBOJUGG-UHFFFAOYSA-N 0.000 description 1
QZCKVDTUOCFVBW-UHFFFAOYSA-N tert-butyl 2-[[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoyl]amino]-3-(4-hydroxyphenyl)propanoate Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)OC(C)(C)C)SC1=NC1CCCCC1 QZCKVDTUOCFVBW-UHFFFAOYSA-N 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
150000003584 thiosemicarbazones Chemical class 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Virology (AREA)
Biomedical Technology (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
AIDS & HIV (AREA)
Transplantation (AREA)
Endocrinology (AREA)
Pain & Pain Management (AREA)
Tropical Medicine & Parasitology (AREA)
Diabetes (AREA)
Orthopedic Medicine & Surgery (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

SK381-2003A 2000-10-02 2001-10-01 New thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors SK3812003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00402710A EP1193261A1 (fr)	2000-10-02	2000-10-02	Thiadiazoles et leur utilisation comme inhibiteurs de phophodiestérase-7
PCT/EP2001/011330 WO2002028847A1 (fr)	2000-10-02	2001-10-01	Nouveaux thiadiazoles et oxadiazoles et utilisation de ceux-ci comme inhibiteurs de la phosphodiesterase de type 7

Publications (1)

Publication Number	Publication Date
SK3812003A3 true SK3812003A3 (en)	2004-05-04

Family

ID=8173891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK381-2003A SK3812003A3 (en)	2000-10-02	2001-10-01	New thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors

Country Status (43)

Country	Link
US (1)	US7122565B2 (fr)
EP (2)	EP1193261A1 (fr)
JP (1)	JP4177098B2 (fr)
KR (1)	KR100614158B1 (fr)
CN (1)	CN1639141A (fr)
AP (1)	AP1541A (fr)
AR (1)	AR035347A1 (fr)
AT (1)	ATE304003T1 (fr)
AU (2)	AU2001289945B2 (fr)
BG (1)	BG107654A (fr)
BR (1)	BR0114391A (fr)
CA (1)	CA2424279A1 (fr)
CZ (1)	CZ2003857A3 (fr)
DE (1)	DE60113283T2 (fr)
DK (1)	DK1326853T3 (fr)
DZ (1)	DZ3440A1 (fr)
EA (1)	EA007179B1 (fr)
EC (1)	ECSP034534A (fr)
EE (1)	EE200300134A (fr)
ES (1)	ES2247166T3 (fr)
GE (1)	GEP20053459B (fr)
GT (1)	GT200100196A (fr)
HN (1)	HN2001000217A (fr)
HR (1)	HRP20030247A2 (fr)
HU (1)	HUP0301248A3 (fr)
IL (1)	IL155122A0 (fr)
IS (1)	IS6759A (fr)
MA (1)	MA25916A1 (fr)
MX (1)	MXPA03002839A (fr)
NO (1)	NO20031482D0 (fr)
NZ (1)	NZ524852A (fr)
OA (1)	OA12518A (fr)
PA (1)	PA8529501A1 (fr)
PE (1)	PE20020419A1 (fr)
PL (1)	PL366332A1 (fr)
PT (1)	PT1326853E (fr)
SI (1)	SI1326853T1 (fr)
SK (1)	SK3812003A3 (fr)
SV (1)	SV2003000633A (fr)
TN (1)	TNSN01139A1 (fr)
WO (1)	WO2002028847A1 (fr)
YU (1)	YU24503A (fr)
ZA (1)	ZA200302346B (fr)

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ES2217956B1 (es) *	2003-01-23	2006-04-01	Almirall Prodesfarma, S.A.	Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo.
JP2006219374A (ja)	2003-06-13	2006-08-24	Daiichi Asubio Pharma Co Ltd	Ｐｄｅ７阻害作用を有するイミダゾトリアジノン誘導体
JP2006219373A (ja)	2003-06-13	2006-08-24	Daiichi Asubio Pharma Co Ltd	Ｐｄｅ７阻害作用を有するピリジニルピラゾロピリミジノン誘導体
PL1775298T3 (pl)	2004-07-01	2013-08-30	Daiichi Sankyo Co Ltd	Pochodna tienopirazolowa wykazująca aktywność hamowania PDE7
EP2258357A3 (fr)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenèse avec inhibiteur de l'acetylcholinestérase
CA2620333A1 (fr)	2005-08-26	2007-03-01	Braincells, Inc.	Neurogenese par modulation du recepteur muscarinique
WO2007047978A2 (fr)	2005-10-21	2007-04-26	Braincells, Inc.	Modulation de la neurogenese par inhibition de la pde
EP1942879A1 (fr)	2005-10-31	2008-07-16	Braincells, Inc.	Modulation de la neurogenese dont la mediation est assuree par recepteur gaba
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
WO2007134077A2 (fr)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenèse induite par le récepteur 5ht
JP2009536669A (ja)	2006-05-09	2009-10-15	ブレインセルス，インコーポレイティド	アンジオテンシン調節による神経新生
KR20090064418A (ko)	2006-09-08	2009-06-18	브레인셀즈 인코퍼레이션	4-아실아미노피리딘 유도체 포함 조합물
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
US8637528B2 (en)	2007-03-27	2014-01-28	Omeros Corporation	Use of PDE7 inhibitors for the treatment of movement disorders
EP2139475B1 (fr)	2007-03-27	2014-12-17	Omeros Corporation	Inhibiteurs de PDE7 pour le traitement de troubles du mouvement
WO2010099217A1 (fr)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation de neurogenèse à l'aide de combinaisons de d-cyclosérine
MD3995C2 (ro) *	2009-05-11	2010-07-31	Государственный Университет Молд0	Utilizare a di(µ-Ofenoxi)-di{[2-(4-aminobenzensulfamido)-5-etil-1,3,4-tiadiazol]-3,5-dibromosalicilidentiosemicarbazonato(-1)-cupru} în calitate de inhibitor al proliferării celulelor T-47D ale cancerului mamar
US8703768B2 (en)	2010-06-09	2014-04-22	Hoffmann-La Roche Inc.	Nitrogen containing heteroaryl compounds
US9220715B2 (en)	2010-11-08	2015-12-29	Omeros Corporation	Treatment of addiction and impulse-control disorders using PDE7 inhibitors
US20120115849A1 (en)	2010-11-08	2012-05-10	Demopulos Gregory A	Treatment of Addiction and Impulse-Control Disorders Using PDE7 Inhibitors
CN102276625B (zh) *	2011-08-24	2013-07-17	天津药物研究院	噻二唑衍生物
WO2013106547A1 (fr)	2012-01-10	2013-07-18	President And Fellows Of Harvard College	Composés promoteurs de réplication des cellules bêta et leurs procédés d'utilisation
CN103288777A (zh) *	2013-05-28	2013-09-11	浙江禾田化工有限公司	特丁噻草隆关键中间体2-甲基氨基-5-叔丁基-1,3,4-噻二唑的合成方法
US9416652B2 (en)	2013-08-08	2016-08-16	Vetco Gray Inc.	Sensing magnetized portions of a wellhead system to monitor fatigue loading
JP6855466B2 (ja) *	2015-06-12	2021-04-07	オリゾンジェノミックスソシエダッドアノニマ	Ｌｓｄ１阻害剤に関連するバイオマーカーおよびそれらの使用
HUE066069T2 (hu)	2016-12-16	2024-07-28	Baxter Int	Mikafungin készítmények
CN107674042B (zh) *	2017-09-28	2020-09-25	河南科技大学	一种超声波无溶剂合成噻二唑类化合物的方法
CN113480486B (zh) *	2021-07-30	2022-05-24	赣南师范大学	一种3-胺基-1,2,4-三唑类衍生物及其制备方法和应用
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2000
- 2000-10-02 EP EP00402710A patent/EP1193261A1/fr not_active Withdrawn
2001
- 2001-09-19 SV SV2001000633A patent/SV2003000633A/es not_active Application Discontinuation
- 2001-09-26 TN TNTNSN01139A patent/TNSN01139A1/en unknown
- 2001-09-27 PA PA20018529501A patent/PA8529501A1/es unknown
- 2001-09-27 AR ARP010104558A patent/AR035347A1/es unknown
- 2001-09-27 GT GT200100196A patent/GT200100196A/es unknown
- 2001-09-27 HN HN2001000217A patent/HN2001000217A/es unknown
- 2001-09-27 PE PE2001000964A patent/PE20020419A1/es not_active Application Discontinuation
- 2001-10-01 DK DK01969804T patent/DK1326853T3/da active
- 2001-10-01 AT AT01969804T patent/ATE304003T1/de not_active IP Right Cessation
- 2001-10-01 PL PL01366332A patent/PL366332A1/xx not_active Application Discontinuation
- 2001-10-01 AU AU2001289945A patent/AU2001289945B2/en not_active Ceased
- 2001-10-01 YU YU24503A patent/YU24503A/sh unknown
- 2001-10-01 SI SI200130423T patent/SI1326853T1/sl unknown
- 2001-10-01 NZ NZ524852A patent/NZ524852A/en unknown
- 2001-10-01 SK SK381-2003A patent/SK3812003A3/sk not_active Application Discontinuation
- 2001-10-01 OA OA1200300092A patent/OA12518A/en unknown
- 2001-10-01 WO PCT/EP2001/011330 patent/WO2002028847A1/fr not_active Ceased
- 2001-10-01 IL IL15512201A patent/IL155122A0/xx unknown
- 2001-10-01 DE DE60113283T patent/DE60113283T2/de not_active Expired - Fee Related
- 2001-10-01 AP APAP/P/2003/002764A patent/AP1541A/en active
- 2001-10-01 HU HU0301248A patent/HUP0301248A3/hu unknown
- 2001-10-01 ES ES01969804T patent/ES2247166T3/es not_active Expired - Lifetime
- 2001-10-01 BR BR0114391-3A patent/BR0114391A/pt not_active IP Right Cessation
- 2001-10-01 HR HR20030247A patent/HRP20030247A2/hr not_active Application Discontinuation
- 2001-10-01 US US09/968,371 patent/US7122565B2/en not_active Expired - Fee Related
- 2001-10-01 DZ DZ013440A patent/DZ3440A1/fr active
- 2001-10-01 JP JP2002532432A patent/JP4177098B2/ja not_active Expired - Fee Related
- 2001-10-01 CA CA002424279A patent/CA2424279A1/fr not_active Abandoned
- 2001-10-01 EE EEP200300134A patent/EE200300134A/xx unknown
- 2001-10-01 GE GE5120A patent/GEP20053459B/en unknown
- 2001-10-01 CN CNA018182070A patent/CN1639141A/zh active Pending
- 2001-10-01 PT PT01969804T patent/PT1326853E/pt unknown
- 2001-10-01 EA EA200300333A patent/EA007179B1/ru not_active IP Right Cessation
- 2001-10-01 MX MXPA03002839A patent/MXPA03002839A/es active IP Right Grant
- 2001-10-01 EP EP01969804A patent/EP1326853B1/fr not_active Expired - Lifetime
- 2001-10-01 KR KR1020037004728A patent/KR100614158B1/ko not_active Expired - Fee Related
- 2001-10-01 CZ CZ2003857A patent/CZ2003857A3/cs unknown
- 2001-10-01 AU AU8994501A patent/AU8994501A/xx active Pending
2003
- 2003-03-20 BG BG107654A patent/BG107654A/bg unknown
- 2003-03-26 ZA ZA200302346A patent/ZA200302346B/en unknown
- 2003-03-27 IS IS6759A patent/IS6759A/is unknown
- 2003-03-31 MA MA27082A patent/MA25916A1/fr unknown
- 2003-04-01 EC EC2003004534A patent/ECSP034534A/es unknown
- 2003-04-01 NO NO20031482A patent/NO20031482D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
ES2247166T3 (es)	2006-03-01
HN2001000217A (es)	2002-06-13
US7122565B2 (en)	2006-10-17
DZ3440A1 (fr)	2002-04-11
AP2003002764A0 (en)	2003-03-31
YU24503A (sh)	2006-03-03
SV2003000633A (es)	2003-04-03
GT200100196A (es)	2002-07-18
EA007179B1 (ru)	2006-08-25
CZ2003857A3 (cs)	2004-02-18
PA8529501A1 (es)	2003-06-30
GEP20053459B (en)	2005-02-25
WO2002028847A1 (fr)	2002-04-11
EP1326853B1 (fr)	2005-09-07
IS6759A (is)	2003-03-27
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ATE304003T1 (de)	2005-09-15
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EA200300333A1 (ru)	2003-10-30
JP4177098B2 (ja)	2008-11-05
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AU2001289945B2 (en)	2005-12-22
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