HRP20030247A2 - New thiadiazoles and oxadiazoles and their use asphosphodiesterase-7 inhibitors - Google Patents
New thiadiazoles and oxadiazoles and their use asphosphodiesterase-7 inhibitors Download PDFInfo
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- HRP20030247A2 HRP20030247A2 HR20030247A HRP20030247A HRP20030247A2 HR P20030247 A2 HRP20030247 A2 HR P20030247A2 HR 20030247 A HR20030247 A HR 20030247A HR P20030247 A HRP20030247 A HR P20030247A HR P20030247 A2 HRP20030247 A2 HR P20030247A2
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- HR
- Croatia
- Prior art keywords
- methyl
- thiadiazol
- dihydro
- phenyl
- cyclohexylimino
- Prior art date
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- 150000004867 thiadiazoles Chemical class 0.000 title claims description 5
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000004866 oxadiazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 284
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 214
- 238000000034 method Methods 0.000 claims description 208
- -1 SO3R5 Proteins 0.000 claims description 171
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 161
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 71
- 125000000623 heterocyclic group Chemical group 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 52
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 201000010099 disease Diseases 0.000 claims description 28
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 26
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000005711 Benzoic acid Substances 0.000 claims description 25
- 125000004450 alkenylene group Chemical group 0.000 claims description 24
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 24
- 125000003367 polycyclic group Chemical group 0.000 claims description 24
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 24
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 101100240521 Caenorhabditis elegans nhr-16 gene Proteins 0.000 claims description 14
- 150000004702 methyl esters Chemical class 0.000 claims description 12
- 101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims description 11
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 11
- 239000002606 phosphodiesterase VII inhibitor Substances 0.000 claims description 11
- 229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 claims description 10
- 125000004419 alkynylene group Chemical group 0.000 claims description 10
- 230000001351 cycling effect Effects 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 claims description 9
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 9
- 208000030507 AIDS Diseases 0.000 claims description 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 8
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
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- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
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- 210000001744 T-lymphocyte Anatomy 0.000 claims description 7
- 150000001263 acyl chlorides Chemical class 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 150000002429 hydrazines Chemical class 0.000 claims description 7
- 230000008569 process Effects 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
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 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 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 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 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 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
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- AYCNLFPKXSXOKW-UHFFFAOYSA-N 2-amino-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=C(N)C(C(N)=O)=CC=2)SC1=NC1CCCCC1 AYCNLFPKXSXOKW-UHFFFAOYSA-N 0.000 claims description 3
- AAHRRMCXCRMPOW-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2,3-dihydroxypropyl)-n-ethylbenzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N(CC(O)CO)CC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 AAHRRMCXCRMPOW-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- JRNONBMYGGXGIU-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(pyridin-4-ylmethyl)benzenesulfonamide Chemical compound CN1N=C(C=2C=C(C(Cl)=CC=2)S(=O)(=O)NCC=2C=CN=CC=2)SC1=NC1CCCCC1 JRNONBMYGGXGIU-UHFFFAOYSA-N 0.000 claims description 3
- YMYNQULHHVYCBW-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-ethyl-n-(2-hydroxy-3-pyrrolidin-1-ylpropyl)benzenesulfonamide Chemical compound C=1C(C=2SC(=NC3CCCCC3)N(C)N=2)=CC=C(Cl)C=1S(=O)(=O)N(CC)CC(O)CN1CCCC1 YMYNQULHHVYCBW-UHFFFAOYSA-N 0.000 claims description 3
- NTTPZIXUCBUUKG-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-ethyl-n-(2-morpholin-4-ylethyl)benzenesulfonamide Chemical compound C=1C(C=2SC(=NC3CCCCC3)N(C)N=2)=CC=C(Cl)C=1S(=O)(=O)N(CC)CCN1CCOCC1 NTTPZIXUCBUUKG-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- LKHKGUJZRJJYTR-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-ethylbenzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)NCC)=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 LKHKGUJZRJJYTR-UHFFFAOYSA-N 0.000 claims description 3
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- OJSBTELXHMNYBM-UHFFFAOYSA-N 3-[[5-(3-cyanophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzoic acid Chemical compound CN1N=C(C=2C=C(C=CC=2)C#N)SC1=NC1=CC=CC(C(O)=O)=C1 OJSBTELXHMNYBM-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
- 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 3
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- 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 3
- 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 3
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- 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 3
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- INFWFVGZGDXGEI-UHFFFAOYSA-N [4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]-(4-pyridin-2-ylpiperazin-1-yl)methanone Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C=2N=CC=CC=2)SC1=NC1CCCCC1 INFWFVGZGDXGEI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940029575 guanosine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 230000021633 leukocyte mediated immunity Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- CHSDCWKLSHPKFY-UHFFFAOYSA-N methyl 1-aminocyclopropane-1-carboxylate;hydrochloride Chemical compound [Cl-].COC(=O)C1([NH3+])CC1 CHSDCWKLSHPKFY-UHFFFAOYSA-N 0.000 description 1
- XIQSMCXDFBPPBP-UHFFFAOYSA-N methyl 2-[5-(4-chlorophenyl)-2-cyclohexylimino-1,3,4-thiadiazol-3-yl]acetate Chemical compound COC(=O)CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1CCCCC1 XIQSMCXDFBPPBP-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- UIJNDYUKONYBJJ-UHFFFAOYSA-N methyl 3-[(3-methyl-5-pyridin-2-yl-1,3,4-thiadiazol-2-ylidene)amino]benzoate Chemical compound COC(=O)C1=CC=CC(N=C2N(N=C(S2)C=2N=CC=CC=2)C)=C1 UIJNDYUKONYBJJ-UHFFFAOYSA-N 0.000 description 1
- LNDSCSUMVQLMJS-UHFFFAOYSA-N methyl 3-[(5-pyridin-2-yl-1,3,4-thiadiazol-2-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2SC(=NN=2)C=2N=CC=CC=2)=C1 LNDSCSUMVQLMJS-UHFFFAOYSA-N 0.000 description 1
- CMGHWWIEHBYHLO-UHFFFAOYSA-N methyl 3-[[5-(3-cyanophenyl)-1,3,4-thiadiazol-2-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2SC(=NN=2)C=2C=C(C=CC=2)C#N)=C1 CMGHWWIEHBYHLO-UHFFFAOYSA-N 0.000 description 1
- KQIZYRLXMBXNQE-UHFFFAOYSA-N methyl 3-[[5-(3-cyanophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]benzoate Chemical compound COC(=O)C1=CC=CC(N=C2N(N=C(S2)C=2C=C(C=CC=2)C#N)C)=C1 KQIZYRLXMBXNQE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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
- RVOOZYXDFHDOOC-UHFFFAOYSA-N methyl n-[(6-acetamidopyridine-3-carbonyl)amino]-n-methylcarbamodithioate Chemical compound CSC(=S)N(C)NC(=O)C1=CC=C(NC(C)=O)N=C1 RVOOZYXDFHDOOC-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical class CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- XRYGCVVVDCEPRL-UHFFFAOYSA-N n,1-dimethylpiperidin-4-amine Chemical compound CNC1CCN(C)CC1 XRYGCVVVDCEPRL-UHFFFAOYSA-N 0.000 description 1
- OUNWLIIWNCCQHW-UHFFFAOYSA-N n-[4-[4-methyl-5-(3-oxocyclohexyl)imino-1,3,4-thiadiazol-2-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(S1)=NN(C)C1=NC1CC(=O)CCC1 OUNWLIIWNCCQHW-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 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
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- DDQLSOTYWAJVGB-UHFFFAOYSA-N n-cyclohexyl-5-thiophen-3-yl-1,3,4-thiadiazol-2-amine Chemical compound C1CCCCC1NC1=NN=C(C2=CSC=C2)S1 DDQLSOTYWAJVGB-UHFFFAOYSA-N 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002773 nucleotide Substances 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
- AEKHNNJSMVVESS-UHFFFAOYSA-N o-trimethylsilylhydroxylamine Chemical compound C[Si](C)(C)ON AEKHNNJSMVVESS-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
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- 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
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- 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
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
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- 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
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002265 prevention Effects 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
- 230000009822 protein phosphorylation Effects 0.000 description 1
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 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
- 238000011160 research Methods 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
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003456 sulfonamides Chemical class 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
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HAKYRVIKISAXRL-HNNXBMFYSA-N tert-butyl (2s)-2-[[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoyl]amino]propanoate Chemical compound C1=CC(C(=O)N[C@@H](C)C(=O)OC(C)(C)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 HAKYRVIKISAXRL-HNNXBMFYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M tetrabutylammoniumhydrogensulfate Substances OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 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
- KNRUQUSSDKZTSQ-UHFFFAOYSA-N tetrazol-1-amine Chemical compound NN1C=NN=N1 KNRUQUSSDKZTSQ-UHFFFAOYSA-N 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
- 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
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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
-
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- 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
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- A61P11/00—Drugs for disorders of the respiratory system
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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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]
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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)
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- Animal Behavior & Ethology (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- 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 (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 |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20030247A2 true HRP20030247A2 (en) | 2005-04-30 |
Family
ID=8173891
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20030247A HRP20030247A2 (en) | 2000-10-02 | 2003-04-01 | New thiadiazoles and oxadiazoles and their use asphosphodiesterase-7 inhibitors |
Country Status (43)
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
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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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