HRP20030247A2 - New thiadiazoles and oxadiazoles and their use asphosphodiesterase-7 inhibitors - Google Patents

Info

Publication number

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

Authority

HR

Croatia

Prior art keywords

methyl

thiadiazol

dihydro

phenyl

cyclohexylimino

Prior art date

2000-10-02

Links

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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
• 125000000732 arylene group Chemical group 0.000 claims description 8
• 210000003169 central nervous system Anatomy 0.000 claims description 8
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
• 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
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 206010028980 Neoplasm Diseases 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
• 239000007943 implant Substances 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 150000002540 isothiocyanates Chemical class 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 210000000496 pancreas Anatomy 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• CMKDBGFYMAVDPA-UHFFFAOYSA-N 2-[[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoyl]amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NC(CC=2C=CC(O)=CC=2)C(O)=O)SC1=NC1CCCCC1 CMKDBGFYMAVDPA-UHFFFAOYSA-N 0.000 claims description 3
• 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
• WLORUJFAFMCLAI-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound CN1N=C(C=2C=C(C(Cl)=CC=2)S(N)(=O)=O)SC1=NC1CCCCC1 WLORUJFAFMCLAI-UHFFFAOYSA-N 0.000 claims description 3
• 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
• 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 3
• BJGVLKHWOUYVPR-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NCCN2CCCC2)SC1=NC1CCCCC1 BJGVLKHWOUYVPR-UHFFFAOYSA-N 0.000 claims description 3
• 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
• CSCMUJLCKQNLDE-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-[(3,4,5-trimethoxyphenyl)methyl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(CNC(=O)C=2C=CC(=CC=2)C=2SC(=NC3CCCCC3)N(C)N=2)=C1 CSCMUJLCKQNLDE-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• 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
• 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 3
• KMIDPBNRYRAMOM-UHFFFAOYSA-N 4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n-quinolin-8-ylbenzamide Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)NC=2C3=NC=CC=C3C=CC=2)SC1=NC1CCCCC1 KMIDPBNRYRAMOM-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• 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 3
• 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 3
• 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 3
• DTOXRIDDHGRZGL-UHFFFAOYSA-N 5-[4-chloro-3-(4-methylpiperazin-1-yl)sulfonylphenyl]-n-cyclohexyl-3-methyl-1,3,4-thiadiazol-2-imine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=CC=C1Cl DTOXRIDDHGRZGL-UHFFFAOYSA-N 0.000 claims description 3
• PETGJGDVCGGLCU-UHFFFAOYSA-N 7-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-1h-quinazolin-4-one Chemical compound CN1N=C(C=2C=C3C(C(NC=N3)=O)=CC=2)SC1=NC1CCCCC1 PETGJGDVCGGLCU-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
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• 239000000460 chlorine Substances 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 125000004494 ethyl ester group Chemical group 0.000 claims description 3
• 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 3
• HMLIQWYFUWNFED-UHFFFAOYSA-N n-[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(S1)=NN(C)C1=NC1CCCCC1 HMLIQWYFUWNFED-UHFFFAOYSA-N 0.000 claims description 3
• RQDOCFUCSDZXNR-UHFFFAOYSA-N n-cyclohexyl-3-methyl-5-(4-methylsulfonylphenyl)-1,3,4-thiadiazol-2-imine Chemical compound CN1N=C(C=2C=CC(=CC=2)S(C)(=O)=O)SC1=NC1CCCCC1 RQDOCFUCSDZXNR-UHFFFAOYSA-N 0.000 claims description 3
• 210000002345 respiratory system Anatomy 0.000 claims description 3
• 125000000565 sulfonamide group Chemical group 0.000 claims description 3
• CMKDBGFYMAVDPA-NRFANRHFSA-N (2s)-2-[[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoyl]amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(O)=O)SC1=NC1CCCCC1 CMKDBGFYMAVDPA-NRFANRHFSA-N 0.000 claims description 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• KDTKWGNEUGWYSK-NMQBUZRESA-N (e)-1-n'-[4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]-2-nitroethene-1,1-diamine Chemical compound CN1N=C(C=2C=CC(N\C(N)=C\[N+]([O-])=O)=CC=2)SC1=NC1CCCCC1 KDTKWGNEUGWYSK-NMQBUZRESA-N 0.000 claims description 2
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• QFOAGJQZDHBRQX-UHFFFAOYSA-N 2,4-dichloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound CN1N=C(C=2C(=CC(Cl)=C(C=2)S(N)(=O)=O)Cl)SC1=NC1CCCCC1 QFOAGJQZDHBRQX-UHFFFAOYSA-N 0.000 claims description 2
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• XJBQVQUDAFFRLA-RBUJURCGSA-N 5-[(e)-2-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)ethenyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(S1)=NN(C)C1=NC1CCCCC1 XJBQVQUDAFFRLA-RBUJURCGSA-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
• RTVAXMAAIDVFHH-UHFFFAOYSA-N 5-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-2-fluorobenzoic acid Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=C(F)C(C(O)=O)=C1 RTVAXMAAIDVFHH-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
• VPWCFYYVODOTNQ-UHFFFAOYSA-N 5-[[5-(4-cyanophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]-2-fluorobenzoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C#N)SC1=NC1=CC=C(F)C(C(O)=O)=C1 VPWCFYYVODOTNQ-UHFFFAOYSA-N 0.000 claims description 2
• WRHWRRIHORYNHM-UHFFFAOYSA-N 7-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-1h-quinazoline-2,4-dione Chemical compound CN1N=C(C=2C=C3C(C(NC(=O)N3)=O)=CC=2)SC1=NC1CCCCC1 WRHWRRIHORYNHM-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
• DYQQZSOTLIPYBH-NNUKFRKNSA-N C1C[C@@H](C)CC[C@@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 Chemical compound C1C[C@@H](C)CC[C@@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 DYQQZSOTLIPYBH-NNUKFRKNSA-N 0.000 claims description 2
• DYQQZSOTLIPYBH-JNSHFYNHSA-N C1C[C@@H](C)CC[C@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 Chemical compound C1C[C@@H](C)CC[C@H]1N=C1N(C)N=C(C=2C=CC(=CC=2)C#N)S1 DYQQZSOTLIPYBH-JNSHFYNHSA-N 0.000 claims description 2
• 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
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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 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• VPXVKAVMTZIQPH-UHFFFAOYSA-N [4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2SC(=NC3CCCCC3)N(C)N=2)C=C1 VPXVKAVMTZIQPH-UHFFFAOYSA-N 0.000 claims description 2
• 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
• IHYQVUAJSWYMBX-UHFFFAOYSA-N [4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]-(4-pyrimidin-2-ylpiperazin-1-yl)methanone Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C=2N=CC=CN=2)SC1=NC1CCCCC1 IHYQVUAJSWYMBX-UHFFFAOYSA-N 0.000 claims description 2
• GBZRSYHVKIAJGI-UHFFFAOYSA-N [4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]-[3-(hydroxymethyl)piperidin-1-yl]methanone Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)N2CC(CO)CCC2)SC1=NC1CCCCC1 GBZRSYHVKIAJGI-UHFFFAOYSA-N 0.000 claims description 2
• DVHXRWXEENDZFQ-UHFFFAOYSA-N [4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)phenyl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound CN1N=C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)SC1=NC1CCCCC1 DVHXRWXEENDZFQ-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
• NYLIOFKAWIMZTB-UHFFFAOYSA-N [5-(4-methylphenyl)imino-4-phenyl-1,3,4-thiadiazol-2-yl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1N=C1N(C=2C=CC=CC=2)N=C(C(=O)C=2C=CC=CC=2)S1 NYLIOFKAWIMZTB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
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• 238000002955 isolation Methods 0.000 claims 5
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• HZCCNMVBAFUWEF-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-3-methyl-1,3,4-thiadiazol-2-ylidene]amino]phenol Chemical compound CN1N=C(C=2C=CC(Cl)=CC=2)SC1=NC1=CC=CC=C1O HZCCNMVBAFUWEF-UHFFFAOYSA-N 0.000 claims 1
• HQOAUCCKJKIOND-UHFFFAOYSA-N 2-amino-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzoic acid Chemical compound CN1N=C(C=2C=C(N)C(C(O)=O)=CC=2)SC1=NC1CCCCC1 HQOAUCCKJKIOND-UHFFFAOYSA-N 0.000 claims 1
• LWJNSRLBFASQLU-UHFFFAOYSA-N 2-chloro-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=C(Cl)C(C(N)=O)=CC=2)SC1=NC1CCCCC1 LWJNSRLBFASQLU-UHFFFAOYSA-N 0.000 claims 1
• QESDBSLFXXITNA-UHFFFAOYSA-N 2-chloro-4-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound CN1N=C(C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)SC1=NC1CCCCC1 QESDBSLFXXITNA-UHFFFAOYSA-N 0.000 claims 1
• DHNRSEQFXUYVPS-UHFFFAOYSA-N 2-chloro-5-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CN1N=C(C=2C=C(C(Cl)=CC=2)C(N)=O)SC1=NC1CCCCC1 DHNRSEQFXUYVPS-UHFFFAOYSA-N 0.000 claims 1
• CUNWREAQDGKTBW-UHFFFAOYSA-N 3-(5-cyclohexylimino-4-methyl-1,3,4-thiadiazol-2-yl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(C=2SC(=NC3CCCCC3)N(C)N=2)=C1 CUNWREAQDGKTBW-UHFFFAOYSA-N 0.000 claims 1
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