BG107654A - Нови тиадиазоли и оксадиазоли и тяхното използване като инхибитори на фосфодиестераза-7 - Google Patents

Нови тиадиазоли и оксадиазоли и тяхното използване като инхибитори на фосфодиестераза-7 Download PDF

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Publication number: BG107654A
Authority: BG; Bulgaria
Prior art keywords: methyl; thiadiazol; dihydro; phenyl; cyclohexylimino
Prior art date: 2000-10-02

Application number

BG107654A

Other languages

Bulgarian (bg)

English (en)

Inventor

Fabrice Vergne

Pierre Ducrot

Charles Andrianjara

Patrick Bernardelli

Edwige Lorthiois

Original Assignee

Warner-Lambert Company, Llc

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

2003-03-20

Publication date

2003-12-31

2003-03-20 Application filed by Warner-Lambert Company, Llc filed Critical Warner-Lambert Company, Llc

2003-12-31 Publication of BG107654A publication Critical patent/BG107654A/bg

Links

239000002606 phosphodiesterase VII inhibitor Substances 0.000 title claims abstract description 8
150000004867 thiadiazoles Chemical class 0.000 title claims description 4
150000004866 oxadiazoles Chemical class 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 141
125000000217 alkyl group Chemical group 0.000 claims abstract description 58
125000003118 aryl group Chemical group 0.000 claims abstract description 39
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 39
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 31
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
125000003367 polycyclic group Chemical group 0.000 claims abstract description 24
229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
238000002360 preparation method Methods 0.000 claims abstract description 20
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 8
229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 7
238000004519 manufacturing process Methods 0.000 claims abstract 2
-1 C 2 -C 6 alkenylene Chemical group 0.000 claims description 374
150000001875 compounds Chemical class 0.000 claims description 280
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 207
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 81
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 71
125000000623 heterocyclic group Chemical group 0.000 claims description 66
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 38
239000005711 Benzoic acid Substances 0.000 claims description 34
150000002367 halogens Chemical class 0.000 claims description 34
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
125000002947 alkylene group Chemical group 0.000 claims description 27
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 24
125000001188 haloalkyl group Chemical group 0.000 claims description 23
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 21
201000010099 disease Diseases 0.000 claims description 21
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 claims description 13
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
125000002619 bicyclic group Chemical group 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 11
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
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101100240521 Caenorhabditis elegans nhr-16 gene Proteins 0.000 claims description 8
150000001412 amines Chemical class 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
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 7
150000001263 acyl chlorides Chemical class 0.000 claims description 7
125000000732 arylene group Chemical group 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
239000001257 hydrogen Substances 0.000 claims description 7
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 7
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 6
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
210000001744 T-lymphocyte Anatomy 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
238000002560 therapeutic procedure Methods 0.000 claims description 6
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
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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 5
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
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 4
ISXIFBSAGNTJIC-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(pyridin-4-ylmethyl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NCC=2C=CN=CC=2)SC1=NC1CCCCC1 ISXIFBSAGNTJIC-UHFFFAOYSA-N 0.000 claims description 4
SZNZUZROGZEZQD-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-[2-(dimethylamino)ethyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 SZNZUZROGZEZQD-UHFFFAOYSA-N 0.000 claims description 4
NMZRIDXUJNXCNG-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 NMZRIDXUJNXCNG-UHFFFAOYSA-N 0.000 claims description 4
GPXKFJSQIAPXSL-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)aniline Chemical compound CN1N=C(C=2C=CC(N)=CC=2)SC1=NC1CCCCC1 GPXKFJSQIAPXSL-UHFFFAOYSA-N 0.000 claims description 4
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 4
SKVDDXFAECGHTI-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methyl-n-[3-(2h-tetrazol-5-yl)phenyl]-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC(C=1)=CC=CC=1C1=NN=NN1 SKVDDXFAECGHTI-UHFFFAOYSA-N 0.000 claims description 4
BWNHTMVTQMRNRC-UHFFFAOYSA-N 5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2,3-dimethoxyphenol Chemical compound OC1=C(OC)C(OC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 BWNHTMVTQMRNRC-UHFFFAOYSA-N 0.000 claims description 4
UZDBDDOQDGKSBO-UHFFFAOYSA-N 5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-methoxybenzene-1,3-diol Chemical compound C1=C(O)C(OC)=C(O)C=C1C(S1)=NN(C)C1=NC1CCCCC1 UZDBDDOQDGKSBO-UHFFFAOYSA-N 0.000 claims description 4
208000023275 Autoimmune disease Diseases 0.000 claims description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
208000019693 Lung disease Diseases 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
150000001299 aldehydes Chemical class 0.000 claims description 4
125000004450 alkenylene group Chemical group 0.000 claims description 4
208000026935 allergic disease Diseases 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
201000011510 cancer Diseases 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
150000002148 esters Chemical class 0.000 claims description 4
229960001867 guaiacol Drugs 0.000 claims description 4
150000002540 isothiocyanates Chemical class 0.000 claims description 4
201000006417 multiple sclerosis Diseases 0.000 claims description 4
MCCMFNCVPDGNOO-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)SC1=NC1CCCCC1 MCCMFNCVPDGNOO-UHFFFAOYSA-N 0.000 claims description 4
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125000001424 substituent group Chemical group 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
FNMQXLNHFVKAQN-UHFFFAOYSA-N 1-[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 FNMQXLNHFVKAQN-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
FBFDHLUQTUXBAH-UHFFFAOYSA-N 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoic acid Chemical compound CN1N=C(C=2C=C(C=CC=2)C(O)=O)SC1=NC1CCCCC1 FBFDHLUQTUXBAH-UHFFFAOYSA-N 0.000 claims description 3
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 3
QTDSDEGMBLGUMB-UHFFFAOYSA-N 3-[[5-(4-carbamoylphenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1=CC=CC(C(O)=O)=C1 QTDSDEGMBLGUMB-UHFFFAOYSA-N 0.000 claims description 3
DJXDQVVNDSVVRH-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-2-hydroxybenzoic acid Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC(C(O)=O)=C1O DJXDQVVNDSVVRH-UHFFFAOYSA-N 0.000 claims description 3
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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
LYBBWEKSYDRJRN-UHFFFAOYSA-N 3-[[5-(4-cyanophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C#N)SC1=NC1=CC=CC(C(O)=O)=C1 LYBBWEKSYDRJRN-UHFFFAOYSA-N 0.000 claims description 3
LJHUZMRHUNPYOK-UHFFFAOYSA-N 4-(5-cycloheptylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzonitrile Chemical compound CN1N=C(C=2C=CC(=CC=2)C#N)SC1=NC1CCCCCC1 LJHUZMRHUNPYOK-UHFFFAOYSA-N 0.000 claims description 3
NBYBBIPNGNEWRS-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2,6-dimethoxypyridin-3-yl)benzamide Chemical compound COC1=NC(OC)=CC=C1NC(=O)C1=CC=C(C=2SC(=NC3CCCCC3)N(C)N=2)C=C1 NBYBBIPNGNEWRS-UHFFFAOYSA-N 0.000 claims description 3
QCKDGBXRPUNDPF-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 QCKDGBXRPUNDPF-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
PQHKACLNJNHBHH-UHFFFAOYSA-N 4-(5-cyclopentylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1CCCC1 PQHKACLNJNHBHH-UHFFFAOYSA-N 0.000 claims description 3
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 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
OHGJXAQKPJSZKQ-UHFFFAOYSA-N 4-[5-(3-bicyclo[2.2.1]heptanylimino)-4-methyl-1,3,4-thiadiazol-2-yl]benzamide Chemical compound S1C(=NC2C3CCC(C3)C2)N(C)N=C1C1=CC=C(C(N)=O)C=C1 OHGJXAQKPJSZKQ-UHFFFAOYSA-N 0.000 claims description 3
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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
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
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LCRFIZVHXGNPNI-JOCQHMNTSA-N CN1N=C(C=2C=CC(=CC=2)C(O)=O)SC1=N[C@H]1CC[C@H](O)CC1 Chemical compound CN1N=C(C=2C=CC(=CC=2)C(O)=O)SC1=N[C@H]1CC[C@H](O)CC1 LCRFIZVHXGNPNI-JOCQHMNTSA-N 0.000 claims description 3
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BOWYQHCFTNADQJ-UHFFFAOYSA-N OC1=CN=NO1 Chemical compound OC1=CN=NO1 BOWYQHCFTNADQJ-UHFFFAOYSA-N 0.000 claims description 3
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VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
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WBMNVLQRJXIFQG-UHFFFAOYSA-N 2-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenol Chemical compound CN1N=C(C=2C(=CC=CC=2)O)SC1=NC1CCCCC1 WBMNVLQRJXIFQG-UHFFFAOYSA-N 0.000 claims description 2
LINLBKJCPLXTLW-UHFFFAOYSA-N 2-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)quinolin-8-ol Chemical compound CN1N=C(C=2N=C3C(O)=CC=CC3=CC=2)SC1=NC1CCCCC1 LINLBKJCPLXTLW-UHFFFAOYSA-N 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
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 description 2
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 2
YXKICBCNUDHBDD-UHFFFAOYSA-N 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2-hydroxyethyl)benzamide Chemical compound CN1N=C(C=2C=C(C=CC=2)C(=O)NCCO)SC1=NC1CCCCC1 YXKICBCNUDHBDD-UHFFFAOYSA-N 0.000 claims description 2
IUDUMODOMZGTSO-UHFFFAOYSA-N 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 IUDUMODOMZGTSO-UHFFFAOYSA-N 0.000 claims description 2
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 2
LUZWOXPDDXACLY-UHFFFAOYSA-N 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound CN1N=C(C=2C=C(C=CC=2)S(N)(=O)=O)SC1=NC1CCCCC1 LUZWOXPDDXACLY-UHFFFAOYSA-N 0.000 claims description 2
KXBWQIVURGRGEI-UHFFFAOYSA-N 3-[[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=CC(C(O)=O)=C1 KXBWQIVURGRGEI-UHFFFAOYSA-N 0.000 claims description 2
LSORXHDZDWCVOC-UHFFFAOYSA-N 3-[[3-methyl-5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-ylidene]amino]cyclohexane-1-carboxylic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)S(C)(=O)=O)SC1=NC1CCCC(C(O)=O)C1 LSORXHDZDWCVOC-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
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
ARXGWWJAFSVHBR-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzoic acid Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC(C(O)=O)=C1 ARXGWWJAFSVHBR-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
OXJZLTQIGAWFGX-UHFFFAOYSA-N 4-(5-cycloheptylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1CCCCCC1 OXJZLTQIGAWFGX-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
FIMPQBSSYHIJFI-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 FIMPQBSSYHIJFI-UHFFFAOYSA-N 0.000 claims description 2
COFGHUOJFZGYFU-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-hydroxybenzamide Chemical compound CN1N=C(C=2C=C(O)C(C(N)=O)=CC=2)SC1=NC1CCCCC1 COFGHUOJFZGYFU-UHFFFAOYSA-N 0.000 claims description 2
AUHBJNGBLVOSHF-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-methoxybenzamide Chemical compound C1=C(C(N)=O)C(OC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 AUHBJNGBLVOSHF-UHFFFAOYSA-N 0.000 claims description 2
JCEZCXZIMXMQGD-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 JCEZCXZIMXMQGD-UHFFFAOYSA-N 0.000 claims description 2
ABNOHYZWJQIMFA-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-methylbenzamide Chemical compound C1=C(C(N)=O)C(C)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 ABNOHYZWJQIMFA-UHFFFAOYSA-N 0.000 claims description 2
UVZCMOWXEHFMHN-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-methylbenzonitrile Chemical compound C1=C(C#N)C(C)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 UVZCMOWXEHFMHN-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
PSKQOVGZNYRGBI-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NCCN2CCOCC2)SC1=NC1CCCCC1 PSKQOVGZNYRGBI-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
KZGMVDKUPXVYNH-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-[(1-ethylpyrrolidin-2-yl)methyl]benzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=C(C=2SC(=NC3CCCCC3)N(C)N=2)C=C1 KZGMVDKUPXVYNH-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
IJYWJWFPUHRWCK-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-[3-(4-methylpiperazin-1-yl)propyl]benzamide Chemical compound C1CN(C)CCN1CCCNC(=O)C1=CC=C(C=2SC(=NC3CCCCC3)N(C)N=2)C=C1 IJYWJWFPUHRWCK-UHFFFAOYSA-N 0.000 claims description 2
BEVDNSMMQAWGSV-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-hydroxybenzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NO)SC1=NC1CCCCC1 BEVDNSMMQAWGSV-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
SMLSCBYVKRXOCN-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzene-1,2-diol Chemical compound CN1N=C(C=2C=C(O)C(O)=CC=2)SC1=NC1CCCCC1 SMLSCBYVKRXOCN-UHFFFAOYSA-N 0.000 claims description 2
OFEHNIXMCHRJCA-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound CN1N=C(C=2C=CC(=CC=2)S(N)(=O)=O)SC1=NC1CCCCC1 OFEHNIXMCHRJCA-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
HBXOHYHTNOFVFZ-UHFFFAOYSA-N 4-(5-cyclopentylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzonitrile Chemical compound CN1N=C(C=2C=CC(=CC=2)C#N)SC1=NC1CCCC1 HBXOHYHTNOFVFZ-UHFFFAOYSA-N 0.000 claims description 2
GYSBHZFLOPZMLK-UHFFFAOYSA-N 4-[4-methyl-5-(4-methylcyclohexyl)imino-1,3,4-thiadiazol-2-yl]benzamide Chemical compound C1CC(C)CCC1N=C1N(C)N=C(C=2C=CC(=CC=2)C(N)=O)S1 GYSBHZFLOPZMLK-UHFFFAOYSA-N 0.000 claims description 2
BTUHNCACMDIGRD-UHFFFAOYSA-N 4-[5-(3-hydroxyphenyl)imino-4-methyl-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1=CC=CC(O)=C1 BTUHNCACMDIGRD-UHFFFAOYSA-N 0.000 claims description 2
KZKJNLCJWFIVQQ-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)imino-4-methyl-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1=CC=C(F)C=C1 KZKJNLCJWFIVQQ-UHFFFAOYSA-N 0.000 claims description 2
IUDADGVGCUIJPK-UHFFFAOYSA-N 4-[5-(4-hydroxycyclohexyl)imino-4-methyl-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1CCC(O)CC1 IUDADGVGCUIJPK-UHFFFAOYSA-N 0.000 claims description 2
CDWRTACTPFUHEY-UHFFFAOYSA-N 4-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzoic acid Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=C(C(O)=O)C=C1 CDWRTACTPFUHEY-UHFFFAOYSA-N 0.000 claims description 2
CSYAYZJHCVUALR-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methyl-n-pentan-3-yl-1,3,4-thiadiazol-2-imine Chemical compound CN1C(=NC(CC)CC)SC(C=2C=CC(Cl)=CC=2)=N1 CSYAYZJHCVUALR-UHFFFAOYSA-N 0.000 claims description 2
WVJMWSNMVJLMTK-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methyl-n-propyl-1,3,4-thiadiazol-2-imine Chemical compound CN1C(=NCCC)SC(C=2C=CC(Cl)=CC=2)=N1 WVJMWSNMVJLMTK-UHFFFAOYSA-N 0.000 claims description 2
FJCRZXZLVGKCAE-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-fluorophenyl)-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=C(F)C=C1 FJCRZXZLVGKCAE-UHFFFAOYSA-N 0.000 claims description 2
BPAFBKRURGLGNH-UHFFFAOYSA-N 5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 BPAFBKRURGLGNH-UHFFFAOYSA-N 0.000 claims description 2
MGDACKWJQPSPMO-UHFFFAOYSA-N 5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzene-1,2,3-triol Chemical compound CN1N=C(C=2C=C(O)C(O)=C(O)C=2)SC1=NC1CCCCC1 MGDACKWJQPSPMO-UHFFFAOYSA-N 0.000 claims description 2
RVKMOHCHMGEETK-UHFFFAOYSA-N 5-[[5-(4-carbamoylphenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-2-fluorobenzoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(N)=O)SC1=NC1=CC=C(F)C(C(O)=O)=C1 RVKMOHCHMGEETK-UHFFFAOYSA-N 0.000 claims description 2
RZUPSYPYOYBGEM-UHFFFAOYSA-N 5-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-2-hydroxybenzoic acid Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=C(O)C(C(O)=O)=C1 RZUPSYPYOYBGEM-UHFFFAOYSA-N 0.000 claims description 2
HBBSXUJVGLTTQR-UHFFFAOYSA-N 5-cyclohexyl-3-methyl-n-(3-methylsulfonylphenyl)-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C2CCCCC2)SC1=NC1=CC=CC(S(C)(=O)=O)=C1 HBBSXUJVGLTTQR-UHFFFAOYSA-N 0.000 claims description 2
UENIZMKYBVMIKJ-UHFFFAOYSA-N 6-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-1h-pyridin-2-one Chemical compound CN1N=C(C=2N=C(O)C=CC=2)SC1=NC1CCCCC1 UENIZMKYBVMIKJ-UHFFFAOYSA-N 0.000 claims description 2
LWVQVYMUENBZPT-UHFFFAOYSA-N 7-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)quinazolin-4-amine Chemical compound CN1N=C(C=2C=C3N=CN=C(N)C3=CC=2)SC1=NC1CCCCC1 LWVQVYMUENBZPT-UHFFFAOYSA-N 0.000 claims description 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
PMGUBCGDIYCGFX-SHTZXODSSA-N C1=CC(NC(=O)C)=CC=C1C(S1)=NN(C)C1=N[C@@H]1CC[C@@H](O)CC1 Chemical compound C1=CC(NC(=O)C)=CC=C1C(S1)=NN(C)C1=N[C@@H]1CC[C@@H](O)CC1 PMGUBCGDIYCGFX-SHTZXODSSA-N 0.000 claims description 2
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 2
NVXONQNITFWGAT-WKILWMFISA-N CN1N=C(C=2C=CC(=CC=2)C(=O)NC(C)(C)CO)SC1=N[C@H]1CC[C@H](O)CC1 Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NC(C)(C)CO)SC1=N[C@H]1CC[C@H](O)CC1 NVXONQNITFWGAT-WKILWMFISA-N 0.000 claims description 2
UYDGKECYIROGIC-UHFFFAOYSA-N [4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]urea Chemical compound CN1N=C(C=2C=CC(NC(N)=O)=CC=2)SC1=NC1CCCCC1 UYDGKECYIROGIC-UHFFFAOYSA-N 0.000 claims description 2
HCPHEWISSWMDIU-UHFFFAOYSA-N [4-phenyl-5-[[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]imino]-1,3,4-thiadiazol-2-yl]-thiophen-2-ylmethanone Chemical compound FC(F)(F)C1=NNC(N=C2N(N=C(S2)C(=O)C=2SC=CC=2)C=2C=CC=CC=2)=N1 HCPHEWISSWMDIU-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
HCGQHTRAKJWMKB-UHFFFAOYSA-N methyl 2-amino-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 HCGQHTRAKJWMKB-UHFFFAOYSA-N 0.000 claims description 2
GNNDTQIHBNTADU-UHFFFAOYSA-N methyl 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 GNNDTQIHBNTADU-UHFFFAOYSA-N 0.000 claims description 2
WBYMOVQFGNAKKM-UHFFFAOYSA-N methyl 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 WBYMOVQFGNAKKM-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
XYRVHQKWTLFBOZ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound S1C(=NC2C3CCN(CC3)C2)N(C)N=C1C1=CC=C(Cl)C=C1 XYRVHQKWTLFBOZ-UHFFFAOYSA-N 0.000 claims description 2
TYWZTRYEHPOCOE-UHFFFAOYSA-N n-(3-chlorophenyl)-5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC(Cl)=C1 TYWZTRYEHPOCOE-UHFFFAOYSA-N 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
IQUHBKNFCDGODB-UHFFFAOYSA-N phenyl-[4-phenyl-5-[[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]imino]-1,3,4-thiadiazol-2-yl]methanone Chemical compound FC(F)(F)C1=NNC(N=C2N(N=C(S2)C(=O)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 IQUHBKNFCDGODB-UHFFFAOYSA-N 0.000 claims description 2
229920002554 vinyl polymer Polymers 0.000 claims description 2
208000009935 visceral pain Diseases 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims 3
150000002431 hydrogen Chemical class 0.000 claims 2
230000003993 interaction Effects 0.000 claims 2
238000002955 isolation Methods 0.000 claims 2
NZGADERMYAURIO-LLVKDONJSA-N (2r)-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-LLVKDONJSA-N 0.000 claims 1
WFZINELXBSJWGR-LBPRGKRZSA-N (2s)-2-[[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)N[C@@H](C)C(O)=O)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 WFZINELXBSJWGR-LBPRGKRZSA-N 0.000 claims 1
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 1
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WPGILNAZLHDZKC-UHFFFAOYSA-N n-cyclohexyl-5-(4-methoxyphenyl)-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound C1=CC(OC)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 WPGILNAZLHDZKC-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
UMEQDKDCPNNBLR-UHFFFAOYSA-N n-cyclohexyl-n,5-di(thiophen-3-yl)-1,3,4-thiadiazol-2-amine Chemical group C1CCCCC1N(C=1SC(=NN=1)C1=CSC=C1)C1=CSC=C1 UMEQDKDCPNNBLR-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
RBVFKMBFVHRPCU-UHFFFAOYSA-N n-trimethylsilylhydroxylamine Chemical compound C[Si](C)(C)NO RBVFKMBFVHRPCU-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
MLPVBIWIRCKMJV-UHFFFAOYSA-N o-aminoethylbenzene Natural products CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical group CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 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
MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000005541 phosphonamide group Chemical group 0.000 description 1
229940081066 picolinic acid Drugs 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
206010036784 proctocolitis Diseases 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
229960004063 propylene glycol Drugs 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
239000012264 purified product Substances 0.000 description 1
NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 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
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
230000004044 response Effects 0.000 description 1
229960000581 salicylamide Drugs 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 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
208000018556 stomach disease Diseases 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000001308 synthesis method Methods 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
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
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
KNRUQUSSDKZTSQ-UHFFFAOYSA-N tetrazol-1-amine Chemical compound NN1C=NN=N1 KNRUQUSSDKZTSQ-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical group 0.000 description 1
SWFSRMBSDMJGOK-UHFFFAOYSA-N thiadiazol-4-ol Chemical compound OC1=CSN=N1 SWFSRMBSDMJGOK-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 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
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000011345 viscous material 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)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Virology (AREA)
Rheumatology (AREA)
Transplantation (AREA)
Neurosurgery (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Endocrinology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Biomedical Technology (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)

BG107654A 2000-10-02 2003-03-20 Нови тиадиазоли и оксадиазоли и тяхното използване като инхибитори на фосфодиестераза-7 BG107654A (bg)

Applications Claiming Priority (2)

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
PCT/EP2001/011330 WO2002028847A1 (en)	2000-10-02	2001-10-01	New thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors

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US (1)	US7122565B2 (is)
EP (2)	EP1193261A1 (is)
JP (1)	JP4177098B2 (is)
KR (1)	KR100614158B1 (is)
CN (1)	CN1639141A (is)
AP (1)	AP1541A (is)
AR (1)	AR035347A1 (is)
AT (1)	ATE304003T1 (is)
AU (2)	AU8994501A (is)
BG (1)	BG107654A (is)
BR (1)	BR0114391A (is)
CA (1)	CA2424279A1 (is)
CZ (1)	CZ2003857A3 (is)
DE (1)	DE60113283T2 (is)
DK (1)	DK1326853T3 (is)
DZ (1)	DZ3440A1 (is)
EA (1)	EA007179B1 (is)
EC (1)	ECSP034534A (is)
EE (1)	EE200300134A (is)
ES (1)	ES2247166T3 (is)
GE (1)	GEP20053459B (is)
GT (1)	GT200100196A (is)
HN (1)	HN2001000217A (is)
HR (1)	HRP20030247A2 (is)
HU (1)	HUP0301248A3 (is)
IL (1)	IL155122A0 (is)
IS (1)	IS6759A (is)
MA (1)	MA25916A1 (is)
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NO (1)	NO20031482D0 (is)
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PE (1)	PE20020419A1 (is)
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SK (1)	SK3812003A3 (is)
SV (1)	SV2003000633A (is)
TN (1)	TNSN01139A1 (is)
WO (1)	WO2002028847A1 (is)
YU (1)	YU24503A (is)
ZA (1)	ZA200302346B (is)

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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
CA2569530C (en)	2004-07-01	2013-07-30	Daiichi Asubio Pharma Co.,Ltd.	Thienopyrazole derivative having pde 7 inhibitory activity
EP1928437A2 (en)	2005-08-26	2008-06-11	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation
EP2258359A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation with sabcomelin
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
WO2007053596A1 (en)	2005-10-31	2007-05-10	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
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EP2026813A2 (en)	2006-05-09	2009-02-25	Braincells, Inc.	5 ht receptor mediated neurogenesis
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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
MX2009010450A (es)	2007-03-27	2009-11-23	Omeros Corp	El uso de inhibidores de la fosfodiesterasa 7 para el tratamiento transtornos del movimiento.
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Also Published As

Publication number	Publication date
DE60113283T2 (de)	2006-06-08
EA200300333A1 (ru)	2003-10-30
TNSN01139A1 (en)	2005-11-10
US7122565B2 (en)	2006-10-17
NO20031482L (no)	2003-04-01
EP1326853B1 (en)	2005-09-07
ECSP034534A (es)	2003-07-25
WO2002028847A1 (en)	2002-04-11
EP1326853A1 (en)	2003-07-16
GT200100196A (es)	2002-07-18
ZA200302346B (en)	2004-08-04
KR20030068542A (ko)	2003-08-21
SV2003000633A (es)	2003-04-03
ES2247166T3 (es)	2006-03-01
GEP20053459B (en)	2005-02-25
SI1326853T1 (sl)	2005-12-31
AU2001289945B2 (en)	2005-12-22
JP4177098B2 (ja)	2008-11-05
AP1541A (en)	2006-01-11
EP1193261A1 (en)	2002-04-03
YU24503A (sh)	2006-03-03
MA25916A1 (fr)	2003-10-01
CZ2003857A3 (cs)	2004-02-18
HUP0301248A3 (en)	2005-06-28
OA12518A (en)	2006-05-29
AU8994501A (en)	2002-04-15
IS6759A (is)	2003-03-27
PT1326853E (pt)	2005-11-30
AR035347A1 (es)	2004-05-12
IL155122A0 (en)	2003-10-31
SK3812003A3 (en)	2004-05-04
PL366332A1 (en)	2005-01-24
MXPA03002839A (es)	2004-09-10
KR100614158B1 (ko)	2006-08-21
DE60113283D1 (de)	2005-10-13
HUP0301248A2 (hu)	2003-10-28
EE200300134A (et)	2003-08-15
CN1639141A (zh)	2005-07-13
NZ524852A (en)	2004-09-24
DZ3440A1 (fr)	2002-04-11
HRP20030247A2 (en)	2005-04-30
CA2424279A1 (en)	2002-04-11
NO20031482D0 (no)	2003-04-01
PE20020419A1 (es)	2002-07-18
BR0114391A (pt)	2003-06-24
ATE304003T1 (de)	2005-09-15
PA8529501A1 (es)	2003-06-30
EA007179B1 (ru)	2006-08-25
US20030045557A1 (en)	2003-03-06
AP2003002764A0 (en)	2003-03-31
JP2004510769A (ja)	2004-04-08
DK1326853T3 (da)	2005-12-12
HN2001000217A (es)	2002-06-13

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