JP2006516610A - チエノ［２，３−ｃ］ピリジン誘導体を含む薬剤組成物、及びその使用 - Google Patents
チエノ［２，３−ｃ］ピリジン誘導体を含む薬剤組成物、及びその使用 Download PDFInfo
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- JP2006516610A JP2006516610A JP2006502633A JP2006502633A JP2006516610A JP 2006516610 A JP2006516610 A JP 2006516610A JP 2006502633 A JP2006502633 A JP 2006502633A JP 2006502633 A JP2006502633 A JP 2006502633A JP 2006516610 A JP2006516610 A JP 2006516610A
- Authority
- JP
- Japan
- 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.)
- Ceased
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 68
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical class C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 228
- 229920002683 Glycosaminoglycan Polymers 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 71
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 70
- 230000003993 interaction Effects 0.000 claims abstract description 46
- 201000010099 disease Diseases 0.000 claims abstract description 40
- 230000001404 mediated effect Effects 0.000 claims abstract description 40
- 238000011282 treatment Methods 0.000 claims abstract description 33
- 208000035475 disorder Diseases 0.000 claims abstract description 30
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 201000011510 cancer Diseases 0.000 claims abstract description 17
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
- 206010002022 amyloidosis Diseases 0.000 claims abstract description 7
- 230000003612 virological effect Effects 0.000 claims abstract description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
- -1 2-[[4-[[Ethyl (phenylmethyl) amino] sulfonyl] benzoyl] amino] -6-ethyl-4,5,6,7-tetrahydrothieno [2,3-c] pyridine-3-carboxamide Thieno [2,3-c] pyridine compound Chemical class 0.000 claims description 128
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 110
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 109
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 103
- 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 72
- 229920000669 heparin Polymers 0.000 claims description 70
- 229960002897 heparin Drugs 0.000 claims description 67
- 108010092694 L-Selectin Proteins 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 40
- 210000004027 cell Anatomy 0.000 claims description 37
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 35
- 239000004480 active ingredient Substances 0.000 claims description 31
- 210000000265 leukocyte Anatomy 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 230000000694 effects Effects 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 108010035766 P-Selectin Proteins 0.000 claims description 25
- 102100023472 P-selectin Human genes 0.000 claims description 25
- 210000000440 neutrophil Anatomy 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims description 21
- 229920002971 Heparan sulfate Polymers 0.000 claims description 20
- 235000005152 nicotinamide Nutrition 0.000 claims description 20
- 239000011570 nicotinamide Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 18
- 230000021164 cell adhesion Effects 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 230000004054 inflammatory process Effects 0.000 claims description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 201000006417 multiple sclerosis Diseases 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 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
- 239000003814 drug Substances 0.000 claims description 12
- 238000001727 in vivo Methods 0.000 claims description 12
- 230000008595 infiltration Effects 0.000 claims description 12
- 238000001764 infiltration Methods 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 206010027476 Metastases Diseases 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 230000006378 damage Effects 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000004494 ethyl ester group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000005973 Carvone Substances 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 230000009401 metastasis Effects 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
- 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 10
- 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 10
- 230000008569 process Effects 0.000 claims description 10
- 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 9
- 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 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000000338 in vitro Methods 0.000 claims description 9
- 206010053567 Coagulopathies Diseases 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
- 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 8
- 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 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 208000032839 leukemia Diseases 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 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
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 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
- 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 5
- 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 5
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 5
- 229920000045 Dermatan sulfate Polymers 0.000 claims description 5
- 230000001363 autoimmune Effects 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000003857 carboxamides Chemical class 0.000 claims description 5
- 229940059329 chondroitin sulfate Drugs 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
- 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
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- 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
- CBSHUWKSSHJYPZ-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(4-methylpiperazin-1-yl)sulfonylbenzamide Chemical compound C1N(CC)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 CBSHUWKSSHJYPZ-UHFFFAOYSA-N 0.000 claims description 5
- YMDJVTMDUDKYKZ-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(4-methylpiperazin-1-yl)sulfonylbenzamide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C=3CCN(C)CC=3S2)C=2SC3=CC=CC=C3N=2)C=C1 YMDJVTMDUDKYKZ-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
- 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
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims description 4
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical group CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 claims description 4
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- 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 3
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| 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 |
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| JP2006516610A true JP2006516610A (ja) | 2006-07-06 |
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| EP (1) | EP1589970A4 (enExample) |
| JP (1) | JP2006516610A (enExample) |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014533733A (ja) * | 2011-11-29 | 2014-12-15 | ギリアド ファーマセット エルエルシー | Ｃ型肝炎ウイルスを処置するための組成物および方法 |
| JP2020514308A (ja) * | 2017-01-13 | 2020-05-21 | 東菱薬品工業株式会社 | 好中球活性化調節剤 |
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| 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 |
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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
- 2004-02-05 CN CNA2004800093693A patent/CN1771037A/zh active Pending
- 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
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2014533733A (ja) * | 2011-11-29 | 2014-12-15 | ギリアド ファーマセット エルエルシー | Ｃ型肝炎ウイルスを処置するための組成物および方法 |
| JP2016053096A (ja) * | 2011-11-29 | 2016-04-14 | ギリアド ファーマセット エルエルシー | Ｃ型肝炎ウイルスを処置するための組成物および方法 |
| JP2020514308A (ja) * | 2017-01-13 | 2020-05-21 | 東菱薬品工業株式会社 | 好中球活性化調節剤 |
| JP7100854B2 (ja) | 2017-01-13 | 2022-07-14 | 東菱薬品工業株式会社 | 好中球活性化調節剤 |
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 |
| CA2515102A1 (en) | 2004-08-19 |
| 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 |
| KR20050100655A (ko) | 2005-10-19 |
| MXPA05008397A (es) | 2006-02-17 |
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