ZA200302346B - 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 PDFInfo
- Publication number
- ZA200302346B ZA200302346B ZA200302346A ZA200302346A ZA200302346B ZA 200302346 B ZA200302346 B ZA 200302346B ZA 200302346 A ZA200302346 A ZA 200302346A ZA 200302346 A ZA200302346 A ZA 200302346A ZA 200302346 B ZA200302346 B ZA 200302346B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- thiadiazol
- dihydro
- cyclohexylimino
- phenyl
- Prior art date
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- 239000002606 phosphodiesterase VII inhibitor Substances 0.000 title claims description 11
- 150000004867 thiadiazoles Chemical class 0.000 title description 3
- 150000004866 oxadiazoles Chemical class 0.000 title description 2
- -1 5-trifluoromethyl-2H-[1,2,4]triazol-3- ylimino Chemical group 0.000 claims description 153
- 150000001875 compounds Chemical class 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000000623 heterocyclic group Chemical group 0.000 claims description 63
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 27
- 125000004450 alkenylene group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000003367 polycyclic group Chemical group 0.000 claims description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 239000005711 Benzoic acid Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004419 alkynylene group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 9
- 229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 claims description 7
- 208000030507 AIDS Diseases 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 6
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
- 150000002429 hydrazines Chemical class 0.000 claims description 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229960001867 guaiacol Drugs 0.000 claims description 4
- 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 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 208000023504 respiratory system disease Diseases 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- WDUPXXTYSQUFPJ-UHFFFAOYSA-N 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=C(C=CC=2)C(N)=O)SC1=NC1CCCCC1 WDUPXXTYSQUFPJ-UHFFFAOYSA-N 0.000 claims description 3
- NLINLEVJNCVGEZ-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzonitrile Chemical compound CN1N=C(C=2C=CC(=CC=2)C#N)SC1=NC1CCCCC1 NLINLEVJNCVGEZ-UHFFFAOYSA-N 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 230000002124 endocrine Effects 0.000 claims description 3
- 230000007717 exclusion Effects 0.000 claims description 3
- 210000003020 exocrine pancreas Anatomy 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 208000024691 pancreas disease Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 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 3
- 208000009935 visceral pain Diseases 0.000 claims description 3
- XPNJUASZEPIKFA-UHFFFAOYSA-N 2-[(3,5-diphenyl-1,3,4-thiadiazol-2-ylidene)amino]-1,4-diphenylbut-2-ene-1,4-dione Chemical compound C=1C=CC=CC=1C(=O)C=C(C(=O)C=1C=CC=CC=1)N=C1SC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 XPNJUASZEPIKFA-UHFFFAOYSA-N 0.000 claims description 2
- DHNRSEQFXUYVPS-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=C(C(Cl)=CC=2)C(N)=O)SC1=NC1CCCCC1 DHNRSEQFXUYVPS-UHFFFAOYSA-N 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
- RFWDXHYWMXMTSV-UHFFFAOYSA-N 3-[(5-cyclohexyl-3-methyl-1,3,4-thiadiazol-2-ylidene)amino]benzoic acid Chemical compound CN1N=C(C2CCCCC2)SC1=NC1=CC=CC(C(O)=O)=C1 RFWDXHYWMXMTSV-UHFFFAOYSA-N 0.000 claims description 2
- BHXLYBRKINDRDO-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-4-hydroxybenzoic acid Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC(C(O)=O)=CC=C1O BHXLYBRKINDRDO-UHFFFAOYSA-N 0.000 claims description 2
- MUZWYUALDIIJKU-UHFFFAOYSA-N 4-(5-cyclohex-3-en-1-ylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1CCC=CC1 MUZWYUALDIIJKU-UHFFFAOYSA-N 0.000 claims description 2
- JEJBLLHMDLAENE-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-oxadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)OC1=NC1CCCCC1 JEJBLLHMDLAENE-UHFFFAOYSA-N 0.000 claims description 2
- JYDUCTYSUKBEJA-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2-ethylpyrazol-3-yl)benzamide Chemical compound CCN1N=CC=C1NC(=O)C1=CC=C(C=2SC(=NC3CCCCC3)N(C)N=2)C=C1 JYDUCTYSUKBEJA-UHFFFAOYSA-N 0.000 claims description 2
- MLQLLPVQUQSOGV-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(O)=O)SC1=NC1CCCCC1 MLQLLPVQUQSOGV-UHFFFAOYSA-N 0.000 claims description 2
- POMCEBRLBHAHKV-UHFFFAOYSA-N 4-[4-methyl-5-(3-oxocyclohexyl)imino-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1CCCC(=O)C1 POMCEBRLBHAHKV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- DKYWZPJMHKCOHC-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methyl-n-propan-2-yl-1,3,4-thiadiazol-2-imine Chemical compound CN1C(=NC(C)C)SC(C=2C=CC(Cl)=CC=2)=N1 DKYWZPJMHKCOHC-UHFFFAOYSA-N 0.000 claims description 2
- UBKURFHJNUIRBY-UHFFFAOYSA-N 5-[(5-cyclohexyl-3-methyl-1,3,4-thiadiazol-2-ylidene)amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1N=C1N(C)N=C(C2CCCCC2)S1 UBKURFHJNUIRBY-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- UPLUFASLXPWQHZ-UHFFFAOYSA-N dimethyl 2-[[5-benzoyl-3-(4-methylphenyl)-1,3,4-thiadiazol-2-ylidene]amino]but-2-enedioate Chemical compound COC(=O)C=C(C(=O)OC)N=C1SC(C(=O)C=2C=CC=CC=2)=NN1C1=CC=C(C)C=C1 UPLUFASLXPWQHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 210000004153 islets of langerhan Anatomy 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WEIRZYTXAXQVPU-UHFFFAOYSA-N methyl 2-chloro-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 WEIRZYTXAXQVPU-UHFFFAOYSA-N 0.000 claims description 2
- PFBBNMXEKXLYRD-UHFFFAOYSA-N methyl 4-(5-cyclohexylimino-4-methyl-1,3,4-oxadiazol-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(O1)=NN(C)C1=NC1CCCCC1 PFBBNMXEKXLYRD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- HMLIQWYFUWNFED-UHFFFAOYSA-N n-[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 HMLIQWYFUWNFED-UHFFFAOYSA-N 0.000 claims description 2
- YYIIUTQRFSWRJY-UHFFFAOYSA-N n-cyclohexyl-3-methyl-5-(5-pyridin-2-ylthiophen-2-yl)-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2SC(=CC=2)C=2N=CC=CC=2)SC1=NC1CCCCC1 YYIIUTQRFSWRJY-UHFFFAOYSA-N 0.000 claims description 2
- PEOQETQTYREJOS-UHFFFAOYSA-N n-cyclohexyl-3-methyl-5-thiophen-3-yl-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C2=CSC=C2)SC1=NC1CCCCC1 PEOQETQTYREJOS-UHFFFAOYSA-N 0.000 claims description 2
- GSZGODOGJZULPX-UHFFFAOYSA-N n-cyclohexyl-5-(3-methoxy-4-nitrophenyl)-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 GSZGODOGJZULPX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims 9
- 238000007363 ring formation reaction Methods 0.000 claims 4
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims 3
- IVBQQHWJIIFRAO-UHFFFAOYSA-N 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenol Chemical compound CN1N=C(C=2C=C(O)C=CC=2)SC1=NC1CCCCC1 IVBQQHWJIIFRAO-UHFFFAOYSA-N 0.000 claims 2
- CSCMUJLCKQNLDE-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-[(3,4,5-trimethoxyphenyl)methyl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(CNC(=O)C=2C=CC(=CC=2)C=2SC(=NC3CCCCC3)N(C)N=2)=C1 CSCMUJLCKQNLDE-UHFFFAOYSA-N 0.000 claims 2
- ILHCAAUBKXDWAM-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1CCCCC1 ILHCAAUBKXDWAM-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- XWWSVPUEUSADRI-UHFFFAOYSA-N N-cyclohexyl-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound C1(CCCCC1)N=C1N(N=CS1)C XWWSVPUEUSADRI-UHFFFAOYSA-N 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- BOIIJURSKJYNBB-UHFFFAOYSA-N 2-[2-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]phenyl]ethanol Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC=C1CCO BOIIJURSKJYNBB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- HZCCNMVBAFUWEF-UHFFFAOYSA-N 2-[[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=C1O HZCCNMVBAFUWEF-UHFFFAOYSA-N 0.000 claims 1
- LWJNSRLBFASQLU-UHFFFAOYSA-N 2-chloro-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=C(Cl)C(C(N)=O)=CC=2)SC1=NC1CCCCC1 LWJNSRLBFASQLU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CDJWSCIHPHMIFO-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2-morpholin-4-ylethyl)-n-propan-2-ylbenzenesulfonamide Chemical compound C=1C(C=2SC(=NC3CCCCC3)N(C)N=2)=CC=C(Cl)C=1S(=O)(=O)N(C(C)C)CCN1CCOCC1 CDJWSCIHPHMIFO-UHFFFAOYSA-N 0.000 claims 1
- GCFAUDGLPSOEQB-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-ethyl-n-[2-(2-methoxyethoxy)ethyl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N(CCOCCOC)CC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 GCFAUDGLPSOEQB-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 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 1
- MKQNYQGIPARLKO-UHFFFAOYSA-N 2-methoxybenzenesulfonamide Chemical compound COC1=CC=CC=C1S(N)(=O)=O MKQNYQGIPARLKO-UHFFFAOYSA-N 0.000 claims 1
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- JSJGEFGEFQKFQY-UHFFFAOYSA-N methyl 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 JSJGEFGEFQKFQY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VFCQIYJQLBIQIA-UHFFFAOYSA-N n-cyclohexyl-3-methyl-5-(1,2-oxazol-5-yl)-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2ON=CC=2)SC1=NC1CCCCC1 VFCQIYJQLBIQIA-UHFFFAOYSA-N 0.000 description 1
- MRLVHNWBDMTSAS-UHFFFAOYSA-N n-cyclohexyl-3-methyl-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C=CC(=CC=2)[N+]([O-])=O)SC1=NC1CCCCC1 MRLVHNWBDMTSAS-UHFFFAOYSA-N 0.000 description 1
- GAJHWHRFULABHR-UHFFFAOYSA-N n-cyclohexyl-3-methyl-5-phenyl-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C=CC=CC=2)SC1=NC1CCCCC1 GAJHWHRFULABHR-UHFFFAOYSA-N 0.000 description 1
- GDULGJCGLRDGKU-UHFFFAOYSA-N n-cyclohexyl-5-(2,4-dichlorophenyl)-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C(=CC(Cl)=CC=2)Cl)SC1=NC1CCCCC1 GDULGJCGLRDGKU-UHFFFAOYSA-N 0.000 description 1
- RVCRXYXXOLXFGS-UHFFFAOYSA-N n-cyclohexyl-5-[4-(1-ethyltetrazol-5-yl)phenyl]-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound CCN1N=NN=C1C1=CC=C(C=2SC(=NC3CCCCC3)N(C)N=2)C=C1 RVCRXYXXOLXFGS-UHFFFAOYSA-N 0.000 description 1
- SGCKSDJIMSBTFY-UHFFFAOYSA-N n-sulfonylformamide Chemical compound O=CN=S(=O)=O SGCKSDJIMSBTFY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 101150009274 nhr-1 gene Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000009822 protein phosphorylation Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- SWFSRMBSDMJGOK-UHFFFAOYSA-N thiadiazol-4-ol Chemical compound OC1=CSN=N1 SWFSRMBSDMJGOK-UHFFFAOYSA-N 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Transplantation (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Neurology (AREA)
- AIDS & HIV (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00402710A EP1193261A1 (en) | 2000-10-02 | 2000-10-02 | New thiadiazoles and their use as phosphodiesterase-7 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302346B true ZA200302346B (en) | 2004-08-04 |
Family
ID=8173891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302346A ZA200302346B (en) | 2000-10-02 | 2003-03-26 | New thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors. |
Country Status (43)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003282087A1 (en) * | 2002-11-13 | 2004-06-03 | Bayer Healthcare Ag | DIAGNOSTICS AND THERAPEUTICS FOR DISEASES ASSOCIATED WITH HUMAN PHOSPHODIESTERASE 7A1 (PDE7a1) |
| 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 |
| EP1775298B1 (en) | 2004-07-01 | 2013-03-20 | Daiichi Sankyo Company, Limited | Thienopyrazole derivative having pde7 inhibitory activity |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| JP2009506069A (ja) | 2005-08-26 | 2009-02-12 | ブレインセルス，インコーポレイティド | ムスカリン性受容体調節による神経発生 |
| JP2009512711A (ja) | 2005-10-21 | 2009-03-26 | ブレインセルス，インコーポレイティド | Ｐｄｅ阻害による神経新生の調節 |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249435A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| AU2007292848A1 (en) | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| 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 |
| US20080260643A1 (en) * | 2007-03-27 | 2008-10-23 | Omeros Corporation | Use of pde7 inhibitors for the treatment of movement disorders |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| 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 |
| KR20170136020A (ko) | 2010-11-08 | 2017-12-08 | 오메로스 코포레이션 | Pde7 억제제를 사용한 중독 및 충동-조절 장애의 치료 |
| US9220715B2 (en) | 2010-11-08 | 2015-12-29 | Omeros Corporation | 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 |
| US20150119399A1 (en) | 2012-01-10 | 2015-04-30 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| 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 |
| MX2017015922A (es) * | 2015-06-12 | 2018-12-11 | Oryzon Genomics Sa | Biomarcadores asociados con inhibidores de lsd1 y usos de los mismos. |
| 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 |
| WO2024038090A1 (en) | 2022-08-18 | 2024-02-22 | Mitodicure Gmbh | Use of substituted benzoxazole and benzofuran compounds for the treatment and prevention of diseases associated with chronic fatigue, exhaustion and/or exertional intolerance |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE251979C (et) | ||||
| FR2388806A1 (fr) | 1977-04-25 | 1978-11-24 | Gulf Oil Corp | Nouvelles 3-benzyl-2-methylimino-5-phenyl4-1,3,4 thiadiazolines et leur application au desherbage chimique de cultures |
| DK270880A (da) | 1979-07-09 | 1981-01-10 | Gulf Oil Corp | Phenyliminothiadiazolidiner deres fremstilling og anvendelse i plantevaekstregulerende midler |
| DD247003A1 (de) * | 1985-11-07 | 1987-06-24 | Hydrierwerk Rodleben Veb | Verfahren zur herstellung von in 2-stellung mit amninhaltigen gruppen subst. 7 h-1,3,4-thiadiazolo(3,2-a)pyrimidinen |
| DD251979A1 (de) * | 1986-08-01 | 1987-12-02 | Neubauer T Paedagog Hochschule | Verfahren zur herstellung von s-triazinylsubstituierten 2-imino-1,3,4-oxadiazolinen |
| DE4418066A1 (de) | 1994-05-24 | 1995-11-30 | Bayer Ag | Substituierte Thiadiazoline |
| ES2203086T3 (es) * | 1998-02-17 | 2004-04-01 | Roche Diagnostics Gmbh | Empleo de derivados de tiadiazolo (4,3-a)piridina. |
-
2000
- 2000-10-02 EP EP00402710A patent/EP1193261A1/en 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 GT GT200100196A patent/GT200100196A/es unknown
- 2001-09-27 AR ARP010104558A patent/AR035347A1/es unknown
- 2001-09-27 PE PE2001000964A patent/PE20020419A1/es not_active Application Discontinuation
- 2001-09-27 HN HN2001000217A patent/HN2001000217A/es unknown
- 2001-09-27 PA PA20018529501A patent/PA8529501A1/es unknown
- 2001-10-01 CN CNA018182070A patent/CN1639141A/zh active Pending
- 2001-10-01 CZ CZ2003857A patent/CZ2003857A3/cs unknown
- 2001-10-01 MX MXPA03002839A patent/MXPA03002839A/es active IP Right Grant
- 2001-10-01 PT PT01969804T patent/PT1326853E/pt unknown
- 2001-10-01 ES ES01969804T patent/ES2247166T3/es not_active Expired - Lifetime
- 2001-10-01 CA CA002424279A patent/CA2424279A1/en not_active Abandoned
- 2001-10-01 PL PL01366332A patent/PL366332A1/xx not_active Application Discontinuation
- 2001-10-01 GE GE5120A patent/GEP20053459B/en unknown
- 2001-10-01 BR BR0114391-3A patent/BR0114391A/pt not_active IP Right Cessation
- 2001-10-01 AT AT01969804T patent/ATE304003T1/de not_active IP Right Cessation
- 2001-10-01 JP JP2002532432A patent/JP4177098B2/ja not_active Expired - Fee Related
- 2001-10-01 WO PCT/EP2001/011330 patent/WO2002028847A1/en active IP Right Grant
- 2001-10-01 AU AU2001289945A patent/AU2001289945B2/en not_active Ceased
- 2001-10-01 AP APAP/P/2003/002764A patent/AP1541A/en active
- 2001-10-01 EE EEP200300134A patent/EE200300134A/et unknown
- 2001-10-01 US US09/968,371 patent/US7122565B2/en not_active Expired - Fee Related
- 2001-10-01 KR KR1020037004728A patent/KR100614158B1/ko not_active IP Right Cessation
- 2001-10-01 SI SI200130423T patent/SI1326853T1/sl unknown
- 2001-10-01 DK DK01969804T patent/DK1326853T3/da active
- 2001-10-01 AU AU8994501A patent/AU8994501A/xx active Pending
- 2001-10-01 OA OA1200300092A patent/OA12518A/en unknown
- 2001-10-01 EP EP01969804A patent/EP1326853B1/en not_active Expired - Lifetime
- 2001-10-01 SK SK381-2003A patent/SK3812003A3/sk not_active Application Discontinuation
- 2001-10-01 IL IL15512201A patent/IL155122A0/xx unknown
- 2001-10-01 HU HU0301248A patent/HUP0301248A3/hu unknown
- 2001-10-01 DE DE60113283T patent/DE60113283T2/de not_active Expired - Fee Related
- 2001-10-01 DZ DZ013440A patent/DZ3440A1/fr active
- 2001-10-01 EA EA200300333A patent/EA007179B1/ru not_active IP Right Cessation
- 2001-10-01 NZ NZ524852A patent/NZ524852A/en unknown
- 2001-10-01 YU YU24503A patent/YU24503A/sh unknown
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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 NO NO20031482A patent/NO20031482D0/no not_active Application Discontinuation
- 2003-04-01 EC EC2003004534A patent/ECSP034534A/es unknown
- 2003-04-01 HR HR20030247A patent/HRP20030247A2/hr not_active Application Discontinuation
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