CA2515102A1 - Pharmaceutical compositions comprising thieno[2,3-c]pyridine derivatives and use thereof - Google Patents
Pharmaceutical compositions comprising thieno[2,3-c]pyridine derivatives and use thereof Download PDFInfo
- Publication number
- CA2515102A1 CA2515102A1 CA002515102A CA2515102A CA2515102A1 CA 2515102 A1 CA2515102 A1 CA 2515102A1 CA 002515102 A CA002515102 A CA 002515102A CA 2515102 A CA2515102 A CA 2515102A CA 2515102 A1 CA2515102 A1 CA 2515102A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridine
- amino
- benzoyl
- sulfonyl
- tetrahydrothieno
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 74
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical class C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 238
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 67
- 229920002683 Glycosaminoglycan Polymers 0.000 claims abstract description 62
- 230000003993 interaction Effects 0.000 claims abstract description 46
- 230000001404 mediated effect Effects 0.000 claims abstract description 40
- 208000035475 disorder Diseases 0.000 claims abstract description 36
- 201000010099 disease Diseases 0.000 claims abstract description 33
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 201000011510 cancer Diseases 0.000 claims abstract description 18
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 10
- 230000003612 virological effect Effects 0.000 claims abstract description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 87
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 84
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 78
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 75
- -1 thieno[2,3-c]pyridine compound Chemical class 0.000 claims description 75
- 229920000669 heparin Polymers 0.000 claims description 68
- 229960002897 heparin Drugs 0.000 claims description 65
- 108010092694 L-Selectin Proteins 0.000 claims description 56
- 238000011282 treatment Methods 0.000 claims description 42
- 239000004480 active ingredient Substances 0.000 claims description 40
- 210000004027 cell Anatomy 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 210000000265 leukocyte Anatomy 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 108010035766 P-Selectin Proteins 0.000 claims description 23
- 102100023472 P-selectin Human genes 0.000 claims description 23
- 210000000440 neutrophil Anatomy 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229920002971 Heparan sulfate Polymers 0.000 claims description 20
- 230000021164 cell adhesion Effects 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 18
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 18
- 230000004054 inflammatory process Effects 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 230000005764 inhibitory process Effects 0.000 claims description 16
- GQIDNMVCAHJPCE-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(diethylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(CC)C2)=C2S1 GQIDNMVCAHJPCE-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 230000008595 infiltration Effects 0.000 claims description 15
- 238000001764 infiltration Methods 0.000 claims description 15
- VPEMNPODXCXJJF-UHFFFAOYSA-N 2-[[4-[benzyl(ethyl)sulfamoyl]benzoyl]amino]-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NC2=C(C=3CCN(CC)CC=3S2)C(N)=O)C=CC=1S(=O)(=O)N(CC)CC1=CC=CC=C1 VPEMNPODXCXJJF-UHFFFAOYSA-N 0.000 claims description 14
- YRSSRCFBMMLSLW-UHFFFAOYSA-N 6-ethyl-2-[[4-(4-methylpiperazin-1-yl)sulfonylbenzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical compound C1N(CC)CCC(C=2C(N)=O)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 YRSSRCFBMMLSLW-UHFFFAOYSA-N 0.000 claims description 14
- 230000006378 damage Effects 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 201000006417 multiple sclerosis Diseases 0.000 claims description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 230000012292 cell migration Effects 0.000 claims description 12
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 12
- 238000001727 in vivo Methods 0.000 claims description 12
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 12
- 235000005152 nicotinamide Nutrition 0.000 claims description 12
- 239000011570 nicotinamide Substances 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 230000006806 disease prevention Effects 0.000 claims description 11
- 206010027476 Metastases Diseases 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 claims description 10
- BQHHKCLXPYGPGT-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-[butyl(ethyl)sulfamoyl]benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CCCC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(CC)C2)=C2S1 BQHHKCLXPYGPGT-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 101000799969 Escherichia coli (strain K12) Alpha-2-macroglobulin Proteins 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000000338 in vitro Methods 0.000 claims description 9
- 230000009401 metastasis Effects 0.000 claims description 9
- 206010053567 Coagulopathies Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
- XTNPTCYECQYVTN-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(diethylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(C)C2)=C2S1 XTNPTCYECQYVTN-UHFFFAOYSA-N 0.000 claims description 8
- CVAIQWZNGNUDNR-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-[methyl(phenyl)sulfamoyl]benzamide Chemical compound C=1C=C(C(=O)NC2=C(C=3CCN(C)CC=3S2)C=2SC3=CC=CC=C3N=2)C=CC=1S(=O)(=O)N(C)C1=CC=CC=C1 CVAIQWZNGNUDNR-UHFFFAOYSA-N 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 208000014674 injury Diseases 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005002 aryl methyl group Chemical group 0.000 claims description 6
- 230000001363 autoimmune Effects 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000012634 fragment Substances 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 5
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 5
- 229920000045 Dermatan sulfate Polymers 0.000 claims description 5
- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- 229940059329 chondroitin sulfate Drugs 0.000 claims description 5
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 claims description 5
- 229940051593 dermatan sulfate Drugs 0.000 claims description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
- USKFCOOWLKKDLE-UHFFFAOYSA-N ethyl 2-[[4-(4-ethoxycarbonylpiperazin-1-yl)sulfonylbenzoyl]amino]-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C=3CCN(CC=3S2)C(C)C)C(=O)OCC)C=C1 USKFCOOWLKKDLE-UHFFFAOYSA-N 0.000 claims description 5
- KLFOEZXNHITOJP-UHFFFAOYSA-N ethyl 3-(1,3-benzothiazol-2-yl)-2-[[4-(diethylsulfamoyl)benzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C1=CC=C(S(=O)(=O)N(CC)CC)C=C1 KLFOEZXNHITOJP-UHFFFAOYSA-N 0.000 claims description 5
- FLQYXSJREWKIED-UHFFFAOYSA-N ethyl 4-[4-[(3-carbamoyl-5,5,7,7-tetramethyl-4,6-dihydrothieno[2,3-c]pyridin-2-yl)carbamoyl]phenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C3=C(C(NC(C)(C)C3)(C)C)S2)C(N)=O)C=C1 FLQYXSJREWKIED-UHFFFAOYSA-N 0.000 claims description 5
- KMJHAJQYFYDERS-UHFFFAOYSA-N ethyl 4-[4-[[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]carbamoyl]phenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C=3CCN(C)CC=3S2)C=2SC3=CC=CC=C3N=2)C=C1 KMJHAJQYFYDERS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 208000017169 kidney disease Diseases 0.000 claims description 5
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 claims description 5
- QSSISUHOHCEHRQ-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-benzyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(diethylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(CC=2C=CC=CC=2)C2)=C2S1 QSSISUHOHCEHRQ-UHFFFAOYSA-N 0.000 claims description 5
- VXXJBJRWVMMHRU-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]benzamide Chemical compound C1=CC=C2SC(C3=C(NC(=O)C=4C=CC(=CC=4)S(=O)(=O)N4C5CC(CC(C)(C)C5)(C)C4)SC4=C3CCN(C4)C)=NC2=C1 VXXJBJRWVMMHRU-UHFFFAOYSA-N 0.000 claims description 5
- FLSOXNKHAMQZIN-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-morpholin-4-ylsulfonylbenzamide Chemical compound C1N(C)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 FLSOXNKHAMQZIN-UHFFFAOYSA-N 0.000 claims description 5
- VIYWMMCQNUKAEQ-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(diethylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(C2)C(C)C)=C2S1 VIYWMMCQNUKAEQ-UHFFFAOYSA-N 0.000 claims description 5
- UQKSAQVUELOLQL-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-morpholin-4-ylsulfonylbenzamide Chemical compound C1N(C(C)C)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 UQKSAQVUELOLQL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical group CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 claims description 4
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical group CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 4
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical group CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 4
- ZOMTULULPOPWSY-UHFFFAOYSA-N 6-ethyl-n-methyl-2-[[4-(4-methylpiperazin-1-yl)sulfonylbenzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical compound C1N(CC)CCC(C=2C(=O)NC)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 ZOMTULULPOPWSY-UHFFFAOYSA-N 0.000 claims description 4
- PYMLRHLGNABFST-UHFFFAOYSA-N 6-ethyl-n-methyl-2-[[4-[methyl(phenyl)sulfamoyl]benzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical compound C1N(CC)CCC(C=2C(=O)NC)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=CC=C1 PYMLRHLGNABFST-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 229920000288 Keratan sulfate Polymers 0.000 claims description 4
- 208000004852 Lung Injury Diseases 0.000 claims description 4
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 208000038016 acute inflammation Diseases 0.000 claims description 4
- 230000006022 acute inflammation Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
- 208000015294 blood coagulation disease Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920005556 chlorobutyl Polymers 0.000 claims description 4
- 208000037976 chronic inflammation Diseases 0.000 claims description 4
- 230000006020 chronic inflammation Effects 0.000 claims description 4
- 230000009852 coagulant defect Effects 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- ADQQLSYRNOPLSQ-UHFFFAOYSA-N ethyl 2-[[4-[butyl(methyl)sulfamoyl]benzoyl]amino]-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylate Chemical compound C1=CC(S(=O)(=O)N(C)CCCC)=CC=C1C(=O)NC1=C(C(=O)OCC)C(CCN(C2)C(C)C)=C2S1 ADQQLSYRNOPLSQ-UHFFFAOYSA-N 0.000 claims description 4
- KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 claims description 4
- 231100000515 lung injury Toxicity 0.000 claims description 4
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
- 201000008383 nephritis Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 208000030507 AIDS Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 208000005176 Hepatitis C Diseases 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 206010033647 Pancreatitis acute Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010061603 Respiratory syncytial virus infection Diseases 0.000 claims description 3
- 206010038910 Retinitis Diseases 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 206010046851 Uveitis Diseases 0.000 claims description 3
- 201000003229 acute pancreatitis Diseases 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 208000002672 hepatitis B Diseases 0.000 claims description 3
- 230000014508 negative regulation of coagulation Effects 0.000 claims description 3
- XBLVHTDFJBKJLG-UHFFFAOYSA-N nicotinic acid ethyl ester Natural products CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims description 3
- 230000007170 pathology Effects 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 230000009529 traumatic brain injury Effects 0.000 claims description 3
- 208000001034 Frostbite Diseases 0.000 claims description 2
- 206010061494 Rhinovirus infection Diseases 0.000 claims description 2
- 206010044541 Traumatic shock Diseases 0.000 claims description 2
- 206010022000 influenza Diseases 0.000 claims description 2
- 201000004792 malaria Diseases 0.000 claims description 2
- 230000035939 shock Effects 0.000 claims description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL15430603A IL154306A0 (en) | 2003-02-05 | 2003-02-05 | Pharmaceutical compositions comprising thieno [2,3-c] pyridine derivatives and use thereof |
| IL154306 | 2003-02-05 | ||
| PCT/IL2004/000121 WO2004069149A2 (en) | 2003-02-05 | 2004-02-05 | Pharmaceutical compositions comprising thieno[2,3-c]pyridine derivatives and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2515102A1 true CA2515102A1 (en) | 2004-08-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002515102A Abandoned CA2515102A1 (en) | 2003-02-05 | 2004-02-05 | Pharmaceutical compositions comprising thieno[2,3-c]pyridine derivatives and use thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7365080B2 (enExample) |
| EP (1) | EP1589970A4 (enExample) |
| JP (1) | JP2006516610A (enExample) |
| KR (1) | KR20050100655A (enExample) |
| CN (1) | CN1771037A (enExample) |
| AU (1) | AU2004210241A1 (enExample) |
| CA (1) | CA2515102A1 (enExample) |
| IL (1) | IL154306A0 (enExample) |
| MX (1) | MXPA05008397A (enExample) |
| WO (1) | WO2004069149A2 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060275214A1 (en) * | 2003-12-30 | 2006-12-07 | Rimonyx Pharmaceuticals Ltd. | Methods of screening for anti-inflammatory drugs and use thereof |
| WO2005089068A2 (en) * | 2004-03-24 | 2005-09-29 | Rimonyx Pharmaceuticals Ltd. | Pharmaceutical compositions comprising anti-inflammatory quinazolinecarboxamide derivatives |
| EP1753512B1 (en) | 2004-05-28 | 2008-07-09 | Nycomed GmbH | Tetrahydropyridothiophenes |
| DE602005007220D1 (de) | 2004-06-04 | 2008-07-10 | Nycomed Gmbh | Tetrahydropyridothiophenen zur verwendung in der behandlung von krebs |
| JP2008501768A (ja) * | 2004-06-11 | 2008-01-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規の化合物及びテトラヒドロピリドチオフェンの使用 |
| US8338648B2 (en) * | 2004-06-12 | 2012-12-25 | Signum Biosciences, Inc. | Topical compositions and methods for epithelial-related conditions |
| CA2596202A1 (en) | 2005-02-09 | 2006-08-17 | Altana Pharma Ag | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| JP2008530053A (ja) | 2005-02-11 | 2008-08-07 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌の治療のための抗増殖性剤としてのテトラヒドロピリドチオフェン |
| AU2006251167A1 (en) | 2005-05-25 | 2006-11-30 | 4Sc Ag | Tetrahydropyridothiophenes for use in the treatment of cancer |
| AU2006251169A1 (en) | 2005-05-25 | 2006-11-30 | 4Sc Ag | Tetrahydropyridothiophenes for use in the treatment of cancer |
| US20100298370A1 (en) * | 2006-03-20 | 2010-11-25 | Paul Gregor | Benzothiazolyl thienopyridine derivatives and uses thereof |
| US8466149B2 (en) | 2007-08-15 | 2013-06-18 | Merck Sharp & Dohme Corp. | 6-substituted sulfonyl azabicyclo[3.2.1]octanes useful to inhibit 11β-hydroxysteroid dehydrogenase type-I |
| RU2364597C1 (ru) * | 2007-12-14 | 2009-08-20 | Андрей Александрович Иващенко | ГЕТЕРОЦИКЛИЧЕСКИЕ ИНГИБИТОРЫ Hh-СИГНАЛЬНОГО КАСКАДА, ЛЕКАРСТВЕННЫЕ КОМПОЗИЦИИ НА ИХ ОСНОВЕ И СПОСОБ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЙ, СВЯЗАННЫХ С АББЕРАНТНОЙ АКТИВНОСТЬЮ Hh СИГНАЛЬНОЙ СИСТЕМЫ |
| EP2307440A4 (en) * | 2008-07-01 | 2012-12-19 | Zacharon Pharmaceuticals Inc | HEPARAN SULFATE INHIBITORS |
| ES2761295T3 (es) | 2009-03-02 | 2020-05-19 | Stemsynergy Therapeutics Inc | Métodos y composiciones para su uso en el tratamiento del cáncer y para reducir los efectos mediados por Wnt en una célula |
| MX2012012421A (es) | 2010-04-28 | 2012-12-17 | Astellas Pharma Inc | Compuestos tetrahidrobenzotiofena. |
| WO2012148889A1 (en) * | 2011-04-28 | 2012-11-01 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibitors of human apurinic/apyrimidinic endonuclease 1 |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| SG11201402609RA (en) * | 2011-11-29 | 2014-06-27 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis c virus |
| CN104829629B (zh) * | 2015-03-26 | 2017-03-15 | 天津药物研究院有限公司 | 含磺酰胺基的四氢噻吩并[2,3‑c]吡啶衍生物、其制备方法和用途 |
| WO2016197078A1 (en) * | 2015-06-05 | 2016-12-08 | Syros Pharmaceuticals, Inc. | Compounds for the modulation of myc activity |
| US10106290B2 (en) | 2015-12-14 | 2018-10-23 | Westrock Shared Services, Llc | Carton, blank, and method of folding |
| US10647725B2 (en) * | 2016-04-21 | 2020-05-12 | The University Of Toledo | Anti-infective 2-aminothiophenes |
| WO2017214941A1 (zh) * | 2016-06-16 | 2017-12-21 | 毛侃琅 | 一种提升SelP基因表达水平的慢病毒载体及其应用 |
| KR20190098204A (ko) | 2016-12-29 | 2019-08-21 | 엔요 파마 | 항바이러스제로서의 티오펜 유도체 |
| CA3049856C (en) * | 2017-01-13 | 2021-10-26 | Tobishi Pharmaceutical Co., Ltd. | Neutrophil activation regulator |
| WO2021050994A1 (en) * | 2019-09-13 | 2021-03-18 | Aerie Pharmaceuticals, Inc. | Heterobicyclic carboxamides and uses thereof |
| AU2022341967A1 (en) * | 2021-09-07 | 2024-05-16 | Gismo Therapeutics, Inc. | Compounds and pharmaceutical compositions comprising inhibitors of amyloid peptide interactions with glycosaminoglycans, methods of treatment, and use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AU4231299A (en) * | 1998-06-04 | 1999-12-20 | Abbott Laboratories | Cell adhesion-inhibiting antinflammatory compounds |
| US6232320B1 (en) * | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| HK1045306A1 (zh) * | 1999-06-03 | 2002-11-22 | Abbott Laboratories | 抑制细胞黏附的抗炎化合物 |
| JP4548882B2 (ja) * | 1999-11-30 | 2010-09-22 | 興和創薬株式会社 | ４，５，６，７−テトラヒドロチエノ〔２，３−ｃ〕ピリジン化合物 |
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2004
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- 2004-02-05 CN CNA2004800093693A patent/CN1771037A/zh active Pending
- 2004-02-05 MX MXPA05008397A patent/MXPA05008397A/es not_active Application Discontinuation
- 2004-02-05 WO PCT/IL2004/000121 patent/WO2004069149A2/en not_active Ceased
- 2004-02-05 US US10/543,065 patent/US7365080B2/en not_active Expired - Fee Related
- 2004-02-05 JP JP2006502633A patent/JP2006516610A/ja not_active Ceased
- 2004-02-05 CA CA002515102A patent/CA2515102A1/en not_active Abandoned
- 2004-02-05 EP EP04708427A patent/EP1589970A4/en not_active Withdrawn
- 2004-02-05 AU AU2004210241A patent/AU2004210241A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1589970A2 (en) | 2005-11-02 |
| KR20050100655A (ko) | 2005-10-19 |
| US7365080B2 (en) | 2008-04-29 |
| MXPA05008397A (es) | 2006-02-17 |
| US20060135529A1 (en) | 2006-06-22 |
| EP1589970A4 (en) | 2008-05-21 |
| CN1771037A (zh) | 2006-05-10 |
| WO2004069149A2 (en) | 2004-08-19 |
| AU2004210241A1 (en) | 2004-08-19 |
| WO2004069149A3 (en) | 2004-11-25 |
| IL154306A0 (en) | 2003-09-17 |
| JP2006516610A (ja) | 2006-07-06 |
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