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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- 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
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL154306 | 2003-02-05 | ||
| IL15430603A IL154306A0 (en) | 2003-02-05 | 2003-02-05 | Pharmaceutical compositions comprising thieno [2,3-c] pyridine derivatives and use thereof |
| 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 |
Family
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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 |
| EP1740176A2 (en) * | 2004-03-24 | 2007-01-10 | Rimonyx Pharmaceuticals Ltd. | Pharmaceutical compositions comprising anti-inflammatory quinazolinecarboxamide derivatives |
| PL1753512T3 (pl) | 2004-05-28 | 2009-03-31 | 4Sc Ag | Tetrahydropirydotiofeny |
| ATE397000T1 (de) | 2004-06-04 | 2008-06-15 | Nycomed Gmbh | Tetrahydropyridothiophenen zur verwendung in der behandlung von krebs |
| US7714134B2 (en) | 2004-06-11 | 2010-05-11 | 4Sc Ag | Compounds and use of tetrahydropyridothiophenes |
| US8338648B2 (en) * | 2004-06-12 | 2012-12-25 | Signum Biosciences, Inc. | Topical compositions and methods for epithelial-related conditions |
| AU2006212224A1 (en) | 2005-02-09 | 2006-08-17 | 4Sc Ag | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| WO2006084904A1 (en) | 2005-02-11 | 2006-08-17 | Nycomed Gmbh | Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer |
| US7714136B2 (en) | 2005-05-25 | 2010-05-11 | 4Sc Ag | Tetrahydropyridothiophenes |
| US7763728B2 (en) | 2005-05-25 | 2010-07-27 | 4Sc Ag | Tetrahydropyridothiophenes |
| US20100298370A1 (en) * | 2006-03-20 | 2010-11-25 | Paul Gregor | Benzothiazolyl thienopyridine derivatives and uses thereof |
| CA2696288A1 (en) * | 2007-08-15 | 2009-02-19 | Schering Corporation | 6-substituted sulfonyl azabicyclo[3.2.1]octanes useful to inhibit 11.beta.-hydroxysteroid dehydrogenase type-1 |
| 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 |
| JP2011526925A (ja) * | 2008-07-01 | 2011-10-20 | ザカロン ファーマシューティカルズ，インク． | ヘパラン硫酸阻害剤 |
| 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 |
| US20130029973A1 (en) | 2010-04-28 | 2013-01-31 | Astellas Pharma Inc. | Tetrahydrobenzothiophene compound |
| 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 |
| EP3777867A1 (en) * | 2011-11-29 | 2021-02-17 | Gilead Pharmasset LLC | Composition and methods for treating hepatitis c virus |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | 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 |
| WO2018122317A1 (en) * | 2016-12-29 | 2018-07-05 | Enyo Pharma | Thiophene derivatives as antiviral agents |
| TWI739983B (zh) * | 2017-01-13 | 2021-09-21 | 日商東菱藥品工業股份有限公司 | 嗜中性白血球活化調節劑 |
| 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 |
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| US6232320B1 (en) * | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| EP1090009A2 (en) * | 1998-06-04 | 2001-04-11 | Abbott Laboratories | Cell adhesion-inhibiting antinflammatory compounds |
| EP1181296A1 (en) * | 1999-06-03 | 2002-02-27 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| 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 MX MXPA05008397A patent/MXPA05008397A/es not_active Application Discontinuation
- 2004-02-05 US US10/543,065 patent/US7365080B2/en not_active Expired - Fee Related
- 2004-02-05 WO PCT/IL2004/000121 patent/WO2004069149A2/en not_active Ceased
- 2004-02-05 EP EP04708427A patent/EP1589970A4/en not_active Withdrawn
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- 2004-02-05 KR KR1020057014345A patent/KR20050100655A/ko not_active Withdrawn
- 2004-02-05 AU AU2004210241A patent/AU2004210241A1/en not_active Abandoned
- 2004-02-05 JP JP2006502633A patent/JP2006516610A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004069149A2 (en) | 2004-08-19 |
| IL154306A0 (en) | 2003-09-17 |
| AU2004210241A1 (en) | 2004-08-19 |
| CN1771037A (zh) | 2006-05-10 |
| EP1589970A4 (en) | 2008-05-21 |
| US20060135529A1 (en) | 2006-06-22 |
| WO2004069149A3 (en) | 2004-11-25 |
| EP1589970A2 (en) | 2005-11-02 |
| US7365080B2 (en) | 2008-04-29 |
| JP2006516610A (ja) | 2006-07-06 |
| KR20050100655A (ko) | 2005-10-19 |
| MXPA05008397A (es) | 2006-02-17 |
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