JP2007535520A5 - - Google Patents
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- JP2007535520A5 JP2007535520A5 JP2007510035A JP2007510035A JP2007535520A5 JP 2007535520 A5 JP2007535520 A5 JP 2007535520A5 JP 2007510035 A JP2007510035 A JP 2007510035A JP 2007510035 A JP2007510035 A JP 2007510035A JP 2007535520 A5 JP2007535520 A5 JP 2007535520A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethoxy
- indole
- group
- methoxyphenyl
- carboxylic acid
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 17
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- -1 hydroxyethyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000002246 antineoplastic agent Substances 0.000 claims 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
- 125000003368 amide group Chemical group 0.000 claims 4
- 125000004185 ester group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 3
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002560 nitrile group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- LORDQUKLQXTKPZ-UHFFFAOYSA-N (5,6-dimethoxy-3-phenyl-1h-indol-2-yl)-morpholin-4-ylmethanone Chemical compound C=1C=CC=CC=1C=1C=2C=C(OC)C(OC)=CC=2NC=1C(=O)N1CCOCC1 LORDQUKLQXTKPZ-UHFFFAOYSA-N 0.000 claims 2
- VRDSTBRNIXSFGB-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)N(CCO)C2=CC(OC)=C(OC)C=C12 VRDSTBRNIXSFGB-UHFFFAOYSA-N 0.000 claims 2
- JZQJPQWAGWVGEO-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5,6-dimethoxy-3-phenylindole-2-carbonitrile Chemical compound N#CC=1N(CCO)C=2C=C(OC)C(OC)=CC=2C=1C1=CC=CC=C1 JZQJPQWAGWVGEO-UHFFFAOYSA-N 0.000 claims 2
- WRTBVIVYFUTKTG-UHFFFAOYSA-N 1-(3-hydroxypropyl)-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)N(CCCO)C2=CC(OC)=C(OC)C=C12 WRTBVIVYFUTKTG-UHFFFAOYSA-N 0.000 claims 2
- PJKNOXRGHPXFBD-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carbonitrile;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=C(C#N)N(CCN(C)C)C2=CC(OC)=C(OC)C=C12 PJKNOXRGHPXFBD-UHFFFAOYSA-N 0.000 claims 2
- HOADMTXRGXJPFH-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-5,6-dimethoxy-3-phenylindole-2-carbonitrile;hydrochloride Chemical compound Cl.N#CC=1N(CCN(C)C)C=2C=C(OC)C(OC)=CC=2C=1C1=CC=CC=C1 HOADMTXRGXJPFH-UHFFFAOYSA-N 0.000 claims 2
- OQNIVCOOZCMYBB-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)N(CCCN(C)C)C2=CC(OC)=C(OC)C=C12 OQNIVCOOZCMYBB-UHFFFAOYSA-N 0.000 claims 2
- OEKNNPPXKIXUBZ-UHFFFAOYSA-N 1-[7,8-dimethoxy-10-(4-methoxyphenyl)-3,4-dihydro-1h-pyrazino[1,2-a]indol-2-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCN(C(C)=O)C2 OEKNNPPXKIXUBZ-UHFFFAOYSA-N 0.000 claims 2
- KPJCTLDXBGZBOO-UHFFFAOYSA-N 2-(5,6-dimethoxy-3-phenyl-1h-indol-2-yl)-4,5-dihydro-1,3-oxazole Chemical compound C=1C=CC=CC=1C=1C=2C=C(OC)C(OC)=CC=2NC=1C1=NCCO1 KPJCTLDXBGZBOO-UHFFFAOYSA-N 0.000 claims 2
- PKQALAZFZVHRNK-UHFFFAOYSA-N 2-[5,6-dimethoxy-3-(4-methoxyphenyl)-1H-indol-2-yl]-5-methyl-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2OC(C)=NN=2)NC2=CC(OC)=C(OC)C=C12 PKQALAZFZVHRNK-UHFFFAOYSA-N 0.000 claims 2
- DAACTXYLMQNTLO-UHFFFAOYSA-N 2-[5,6-dimethoxy-3-(4-methoxyphenyl)-2-(5-methyl-1,3,4-oxadiazol-2-yl)indol-1-yl]-n,n-dimethylethanamine Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C1N1CCN(C)C)=C1C1=NN=C(C)O1 DAACTXYLMQNTLO-UHFFFAOYSA-N 0.000 claims 2
- LENZMQGXLVYFBT-UHFFFAOYSA-N 2-[5,6-dimethoxy-3-(4-methoxyphenyl)-2-(5-methyl-1,3,4-oxadiazol-2-yl)indol-1-yl]ethanol Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C1N1CCO)=C1C1=NN=C(C)O1 LENZMQGXLVYFBT-UHFFFAOYSA-N 0.000 claims 2
- XSTFNIJEXSUSAR-UHFFFAOYSA-N 2-indol-1-yl-3H-oxadiazole Chemical compound O1N(NC=C1)N1C=CC2=CC=CC=C12 XSTFNIJEXSUSAR-UHFFFAOYSA-N 0.000 claims 2
- GOMKJZNSPXZXQI-UHFFFAOYSA-N 5,6-dimethoxy-3-(4-methoxyphenyl)-1-(2-morpholin-4-ylethyl)indole-2-carbonitrile;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C(C#N)N1CCN1CCOCC1 GOMKJZNSPXZXQI-UHFFFAOYSA-N 0.000 claims 2
- TZAJMZPWHHOSDR-UHFFFAOYSA-N 5,6-dimethoxy-3-(4-methoxyphenyl)-1-(2-pyrrolidin-1-ylethyl)indole-2-carbonitrile;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C(C#N)N1CCN1CCCC1 TZAJMZPWHHOSDR-UHFFFAOYSA-N 0.000 claims 2
- MJIIFQSGKWOMJQ-UHFFFAOYSA-N 5,6-dimethoxy-3-(4-methoxyphenyl)-1-[2-(4-methylpiperazin-1-yl)ethyl]indole-2-carbonitrile;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C(C#N)N1CCN1CCN(C)CC1 MJIIFQSGKWOMJQ-UHFFFAOYSA-N 0.000 claims 2
- GDJLZLJTRKUMEJ-UHFFFAOYSA-N 5,6-dimethoxy-3-(4-methoxyphenyl)-1h-indole-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)NC2=CC(OC)=C(OC)C=C12 GDJLZLJTRKUMEJ-UHFFFAOYSA-N 0.000 claims 2
- KMTHJDFUUPIDOC-UHFFFAOYSA-N 5,6-dimethoxy-3-(4-methoxyphenyl)-2-(1H-1,2,4-triazol-5-yl)-1H-indole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2NN=CN=2)NC2=CC(OC)=C(OC)C=C12 KMTHJDFUUPIDOC-UHFFFAOYSA-N 0.000 claims 2
- TUYBZVBOPJMOCY-UHFFFAOYSA-N 5,6-dimethoxy-3-(4-methoxyphenyl)-2-(2H-tetrazol-5-yl)-1H-indole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2NN=NN=2)NC2=CC(OC)=C(OC)C=C12 TUYBZVBOPJMOCY-UHFFFAOYSA-N 0.000 claims 2
- SRLBTZMZYZDXTF-UHFFFAOYSA-N 5,6-dimethoxy-3-phenyl-1-propylindole-2-carbonitrile Chemical compound C12=CC(OC)=C(OC)C=C2N(CCC)C(C#N)=C1C1=CC=CC=C1 SRLBTZMZYZDXTF-UHFFFAOYSA-N 0.000 claims 2
- MOUMUITYHSHJGQ-UHFFFAOYSA-N 5,6-dimethoxy-3-phenyl-1h-indole-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C#N)=C1C1=CC=CC=C1 MOUMUITYHSHJGQ-UHFFFAOYSA-N 0.000 claims 2
- ILIFMLLAFSCLJM-UHFFFAOYSA-N 5,6-dimethoxy-3-phenyl-2-(1H-1,2,4-triazol-5-yl)-1H-indole Chemical compound C=1C=CC=CC=1C=1C=2C=C(OC)C(OC)=CC=2NC=1C1=NN=CN1 ILIFMLLAFSCLJM-UHFFFAOYSA-N 0.000 claims 2
- FLFYNTHFAXXVOE-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCNC2 FLFYNTHFAXXVOE-UHFFFAOYSA-N 0.000 claims 2
- OSMBPVBPUKXOQW-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-2,4-dihydro-1h-pyrazino[1,2-a]indol-3-one Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CC(=O)NC2 OSMBPVBPUKXOQW-UHFFFAOYSA-N 0.000 claims 2
- JQDPWKYSIKYUBZ-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrazino[1,2-a]indole Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCN(S(=O)(=O)C=1C=CC(C)=CC=1)C2 JQDPWKYSIKYUBZ-UHFFFAOYSA-N 0.000 claims 2
- NBKOJGYFPMCRLC-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-2-methyl-3,4-dihydro-1h-pyrazino[1,2-a]indole;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCN(C)C2 NBKOJGYFPMCRLC-UHFFFAOYSA-N 0.000 claims 2
- CCVOMIOATVNKPF-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-2-methylsulfonyl-3,4-dihydro-1h-pyrazino[1,2-a]indole Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCN(S(C)(=O)=O)C2 CCVOMIOATVNKPF-UHFFFAOYSA-N 0.000 claims 2
- WKFLURXVXBOZPW-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-2-propan-2-yl-3,4-dihydro-1h-pyrazino[1,2-a]indole;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCN(C(C)C)C2 WKFLURXVXBOZPW-UHFFFAOYSA-N 0.000 claims 2
- CROSEMLHHCGFEG-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-2-propan-2-ylsulfonyl-3,4-dihydro-1h-pyrazino[1,2-a]indole Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCN(S(=O)(=O)C(C)C)C2 CROSEMLHHCGFEG-UHFFFAOYSA-N 0.000 claims 2
- UCNZPMHYGWAUKW-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-3,4-dihydro-1h-[1,4]oxazino[4,3-a]indole Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCOC2 UCNZPMHYGWAUKW-UHFFFAOYSA-N 0.000 claims 2
- KTROSXPIJJZINL-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one Chemical compound C1=CC(OC)=CC=C1C(C1=CC(OC)=C(OC)C=C11)=C2N1CCNC2=O KTROSXPIJJZINL-UHFFFAOYSA-N 0.000 claims 2
- KAAZZEBFTFXGJQ-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-n-methyl-3,4-dihydro-1h-pyrazino[1,2-a]indole-2-carboxamide Chemical compound C1N(C(=O)NC)CCN(C2=CC(OC)=C(OC)C=C22)C1=C2C1=CC=C(OC)C=C1 KAAZZEBFTFXGJQ-UHFFFAOYSA-N 0.000 claims 2
- RSWFMUPFLONLLK-UHFFFAOYSA-N 7,8-dimethoxy-10-phenyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole;hydrochloride Chemical compound Cl.C=12CNCCN2C=2C=C(OC)C(OC)=CC=2C=1C1=CC=CC=C1 RSWFMUPFLONLLK-UHFFFAOYSA-N 0.000 claims 2
- LRXXWNGXTYIZBE-UHFFFAOYSA-N 7,8-dimethoxy-10-phenyl-3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one Chemical compound C=12C(=O)NCCN2C=2C=C(OC)C(OC)=CC=2C=1C1=CC=CC=C1 LRXXWNGXTYIZBE-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000001802 infusion Methods 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- KVDJLKCCIRQYTG-UHFFFAOYSA-N methyl 1-(2-amino-2-oxoethyl)-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CC(N)=O)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 KVDJLKCCIRQYTG-UHFFFAOYSA-N 0.000 claims 2
- YFEYHWKORAOCAF-UHFFFAOYSA-N methyl 1-(2-aminoethyl)-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2N(CCN)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 YFEYHWKORAOCAF-UHFFFAOYSA-N 0.000 claims 2
- YGLHNIWIMOFCRJ-UHFFFAOYSA-N methyl 1-(2-hydroxyethyl)-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CCO)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 YGLHNIWIMOFCRJ-UHFFFAOYSA-N 0.000 claims 2
- FCBGCWBDDDUSLI-UHFFFAOYSA-N methyl 1-(3-hydroxypropyl)-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CCCO)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 FCBGCWBDDDUSLI-UHFFFAOYSA-N 0.000 claims 2
- KXFOXHRUJNNQAQ-UHFFFAOYSA-N methyl 1-(cyanomethyl)-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CC#N)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 KXFOXHRUJNNQAQ-UHFFFAOYSA-N 0.000 claims 2
- QOPYGQMLZKFFPO-UHFFFAOYSA-N methyl 1-[2-(dimethylamino)-2-oxoethyl]-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CC(=O)N(C)C)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 QOPYGQMLZKFFPO-UHFFFAOYSA-N 0.000 claims 2
- KSBIKQMUESKOMW-UHFFFAOYSA-N methyl 1-[2-(dimethylamino)ethyl]-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2N(CCN(C)C)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 KSBIKQMUESKOMW-UHFFFAOYSA-N 0.000 claims 2
- KPDNFZPAGRGBCO-UHFFFAOYSA-N methyl 1-[3-(dimethylamino)propyl]-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2N(CCCN(C)C)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 KPDNFZPAGRGBCO-UHFFFAOYSA-N 0.000 claims 2
- PIFNRGUHVQRYKQ-UHFFFAOYSA-N methyl 1-benzyl-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CC=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 PIFNRGUHVQRYKQ-UHFFFAOYSA-N 0.000 claims 2
- RZACXYWBWBAXKO-UHFFFAOYSA-N methyl 5,6-dimethoxy-1-(2-methoxy-2-oxoethyl)-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CC(=O)OC)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 RZACXYWBWBAXKO-UHFFFAOYSA-N 0.000 claims 2
- FHLHBJCFQGAUSD-UHFFFAOYSA-N methyl 5,6-dimethoxy-1-(2-methoxyethyl)-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CCOC)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 FHLHBJCFQGAUSD-UHFFFAOYSA-N 0.000 claims 2
- ZLZSBGQEXCNVHA-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methoxyphenyl)-1-(2-morpholin-4-ylethyl)indole-2-carboxylate;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2N(CCN2CCOCC2)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 ZLZSBGQEXCNVHA-UHFFFAOYSA-N 0.000 claims 2
- JQORPSVTMQXKID-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methoxyphenyl)-1-(2-pyrrolidin-1-ylethyl)indole-2-carboxylate;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2N(CCN2CCCC2)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 JQORPSVTMQXKID-UHFFFAOYSA-N 0.000 claims 2
- ORFITJDJBBTDQZ-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methoxyphenyl)-1-[2-(4-methylpiperazin-1-yl)ethyl]indole-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2N(CCN2CCN(C)CC2)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 ORFITJDJBBTDQZ-UHFFFAOYSA-N 0.000 claims 2
- MXCOSTUYBATMQM-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methoxyphenyl)-1-[2-(methylamino)-2-oxoethyl]indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CC(=O)NC)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 MXCOSTUYBATMQM-UHFFFAOYSA-N 0.000 claims 2
- UAZIEQFZSVQFEC-UHFFFAOYSA-N n-[[5,6-dimethoxy-3-(4-methoxyphenyl)-1h-indol-2-yl]methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=C(CNC(C)=O)NC2=CC(OC)=C(OC)C=C12 UAZIEQFZSVQFEC-UHFFFAOYSA-N 0.000 claims 2
- AEIDURNZWCNQIM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazino[1,2-a]indole Chemical compound C1=CC=C2N3CCNCC3=CC2=C1 AEIDURNZWCNQIM-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- HVZAFNRIZAKUQS-UHFFFAOYSA-N 3,4-dihydro-1h-[1,4]oxazino[4,3-a]indole Chemical compound C1=CC=C2N3CCOCC3=CC2=C1 HVZAFNRIZAKUQS-UHFFFAOYSA-N 0.000 claims 1
- KRRWBFJXTNMYOZ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one Chemical compound C1=CC=C2N3CCNC(=O)C3=CC2=C1 KRRWBFJXTNMYOZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- TWLJBVBWKQFUQD-UHFFFAOYSA-N 5,6-dimethoxy-3-(4-methoxyphenyl)-1h-indole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(N)=O)NC2=CC(OC)=C(OC)C=C12 TWLJBVBWKQFUQD-UHFFFAOYSA-N 0.000 claims 1
- LRJRYRFBXQZDRU-UHFFFAOYSA-N 5,6-dimethoxy-3-phenyl-1h-indole-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C(N)=O)=C1C1=CC=CC=C1 LRJRYRFBXQZDRU-UHFFFAOYSA-N 0.000 claims 1
- GEDABJRCUZMZJI-UHFFFAOYSA-N 5,6-dimethoxy-n,n-dimethyl-3-phenyl-1h-indole-2-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C(=O)N(C)C)=C1C1=CC=CC=C1 GEDABJRCUZMZJI-UHFFFAOYSA-N 0.000 claims 1
- PNBJSBFFPBYBOR-UHFFFAOYSA-N 5,6-dimethoxy-n-methyl-3-phenyl-1h-indole-2-carboxamide Chemical compound CNC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=CC=C1 PNBJSBFFPBYBOR-UHFFFAOYSA-N 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000002699 Digestive System Neoplasms Diseases 0.000 claims 1
- 229940123237 Taxane Drugs 0.000 claims 1
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
- 239000002257 antimetastatic agent Substances 0.000 claims 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 208000025997 central nervous system neoplasm Diseases 0.000 claims 1
- 210000002249 digestive system Anatomy 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- JPDIBWCNNQFQEP-UHFFFAOYSA-N ethyl 3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=CC=C2C=1C1=CC=CC=C1 JPDIBWCNNQFQEP-UHFFFAOYSA-N 0.000 claims 1
- PVKRDBCQHZFPAX-UHFFFAOYSA-N ethyl 5,6-dimethoxy-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=CC=C1 PVKRDBCQHZFPAX-UHFFFAOYSA-N 0.000 claims 1
- FSLOLRKVZPTMHC-UHFFFAOYSA-N ethyl 5-chloro-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 FSLOLRKVZPTMHC-UHFFFAOYSA-N 0.000 claims 1
- XBBONQKRNZIXTH-UHFFFAOYSA-N ethyl 5-fluoro-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(F)C=C2C=1C1=CC=CC=C1 XBBONQKRNZIXTH-UHFFFAOYSA-N 0.000 claims 1
- LLBDOBISQBECLH-UHFFFAOYSA-N ethyl 5-hydroxy-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(O)C=C2C=1C1=CC=CC=C1 LLBDOBISQBECLH-UHFFFAOYSA-N 0.000 claims 1
- DOIDLAVLCKENCM-UHFFFAOYSA-N ethyl 5-methoxy-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(OC)C=C2C=1C1=CC=CC=C1 DOIDLAVLCKENCM-UHFFFAOYSA-N 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 239000007902 hard capsule Substances 0.000 claims 1
- 229940041682 inhalant solution Drugs 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- CHXQLKJUJCVMTK-UHFFFAOYSA-N methyl 3-(2-chlorophenyl)-5,6-dimethoxy-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=CC=C1Cl CHXQLKJUJCVMTK-UHFFFAOYSA-N 0.000 claims 1
- KFZGADIVBKXPKF-UHFFFAOYSA-N methyl 3-(3,4-dimethoxyphenyl)-5,6-dimethoxy-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C(OC)=C1 KFZGADIVBKXPKF-UHFFFAOYSA-N 0.000 claims 1
- NQCOHWFQRSVAHH-UHFFFAOYSA-N methyl 3-(3-chlorophenyl)-5,6-dimethoxy-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=CC(Cl)=C1 NQCOHWFQRSVAHH-UHFFFAOYSA-N 0.000 claims 1
- HLNDMBOAQWCCGQ-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-5,6-dimethoxy-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=C(Cl)C=C1 HLNDMBOAQWCCGQ-UHFFFAOYSA-N 0.000 claims 1
- RWBHWSUJSFZICA-UHFFFAOYSA-N methyl 3-(4-fluorophenyl)-5,6-dimethoxy-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=C(F)C=C1 RWBHWSUJSFZICA-UHFFFAOYSA-N 0.000 claims 1
- AZSXHQAYXGZVCY-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC=CC=C2C=1C1=CC=C(OC)C=C1 AZSXHQAYXGZVCY-UHFFFAOYSA-N 0.000 claims 1
- UCOFWTALVXAQCE-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methoxyphenyl)-1-propylindole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CCC)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 UCOFWTALVXAQCE-UHFFFAOYSA-N 0.000 claims 1
- IYNGKMZSLRPOQX-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methoxyphenyl)-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C=C1 IYNGKMZSLRPOQX-UHFFFAOYSA-N 0.000 claims 1
- PVFSUKCFXLNXNT-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methylphenyl)-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=C(C)C=C1 PVFSUKCFXLNXNT-UHFFFAOYSA-N 0.000 claims 1
- LFWJSDFFEOXJSR-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-[4-(trifluoromethyl)phenyl]-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=C(C(F)(F)F)C=C1 LFWJSDFFEOXJSR-UHFFFAOYSA-N 0.000 claims 1
- DZYDQRZYZTVOGA-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-phenyl-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=CC=C1 DZYDQRZYZTVOGA-UHFFFAOYSA-N 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 239000003094 microcapsule Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 150000003058 platinum compounds Chemical class 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000002534 radiation-sensitizing agent Substances 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 239000007901 soft capsule Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000029584 urinary system neoplasm Diseases 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000874A ITMI20040874A1 (it) | 2004-04-30 | 2004-04-30 | Derivati indolici ed azaindolici con azione antitumorale |
| PCT/EP2005/051908 WO2005105213A2 (en) | 2004-04-30 | 2005-04-27 | Indole and azaindole derivatives with antitumor action |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007535520A JP2007535520A (ja) | 2007-12-06 |
| JP2007535520A5 true JP2007535520A5 (https=) | 2008-06-19 |
Family
ID=34968098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007510035A Pending JP2007535520A (ja) | 2004-04-30 | 2005-04-27 | 抗腫瘍作用を有するインドール及びアザインドール誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20070248672A1 (https=) |
| EP (1) | EP1750687A2 (https=) |
| JP (1) | JP2007535520A (https=) |
| AU (1) | AU2005237788A1 (https=) |
| CA (1) | CA2564249A1 (https=) |
| IT (1) | ITMI20040874A1 (https=) |
| WO (1) | WO2005105213A2 (https=) |
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| TWI372624B (en) | 2004-03-30 | 2012-09-21 | Vertex Pharma | Azaindoles useful as inhibitors of jak and other protein kinases |
| EP1779848A1 (en) | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of inflammatory and autoimmune diseases |
| EP1779849A1 (en) * | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of septic shock |
| WO2008033464A2 (en) | 2006-09-15 | 2008-03-20 | Schering Corporation | Azetidinone derivatives for the treatment of disorders of the lipid metabolism |
| AU2007338754A1 (en) | 2006-12-21 | 2008-07-03 | Vertex Pharmaceuticals Incorporated | 5-cyan0-4- (pyrrolo [2, 3B] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors |
| EP2134176A4 (en) * | 2007-03-30 | 2012-08-29 | Brigham & Womens Hospital | COMPOUNDS AND METHODS FOR ENHANCING MHC CLASS II THERAPIES |
| MX2009011210A (es) * | 2007-04-16 | 2009-10-30 | Abbott Lab | Inhibidores de mcl1 de indol 7-no sustituido. |
| WO2010144611A2 (en) * | 2009-06-10 | 2010-12-16 | 3-V Biosciences, Inc. | Antivirals that target transporters, carriers, and ion channels |
| RS57869B1 (sr) | 2009-06-17 | 2018-12-31 | Vertex Pharma | Inhibitori replikacije virusa gripa |
| CN102791688B (zh) * | 2009-10-07 | 2014-11-12 | 卡罗生物股份公司 | 雌激素受体配体 |
| US8691830B2 (en) | 2010-10-25 | 2014-04-08 | G1 Therapeutics, Inc. | CDK inhibitors |
| KR102051881B1 (ko) | 2010-10-25 | 2019-12-04 | 쥐원 쎄라퓨틱스, 인크. | Cdk 억제제 |
| AU2011343642A1 (en) | 2010-12-16 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| GB201113538D0 (en) | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| SI2825541T1 (sl) | 2012-03-16 | 2016-10-28 | Vitae Pharmaceuticals, Inc. | Modulatorji jetrnega receptorja X |
| ES2607113T3 (es) | 2012-03-16 | 2017-03-29 | Vitae Pharmaceuticals, Inc. | Moduladores de los receptores X del hígado |
| AU2013239816B2 (en) | 2012-03-29 | 2017-08-24 | G1 Therapeutics, Inc. | Lactam kinase inhibitors |
| ES2734479T3 (es) * | 2012-09-21 | 2019-12-10 | Vivolux Ab | Medios y métodos para tratar tumores sólidos |
| HK1222766A1 (zh) | 2013-03-15 | 2017-07-14 | G1治疗公司 | 高效的抗赘生剂和抗增生剂 |
| DK2968290T3 (da) | 2013-03-15 | 2019-11-25 | G1 Therapeutics Inc | Transient beskyttelse af normale celler under kemoterapi |
| WO2014173901A1 (en) * | 2013-04-23 | 2014-10-30 | Laboratorios Del Dr. Esteve, S.A. | PYRAZINO[1,2-a]INDOLE COMPOUNDS, THEIR PREPARATION AND USE IN MEDICAMENTS |
| RS59144B1 (sr) | 2013-11-13 | 2019-09-30 | Vertex Pharma | Inhibitori replikacije virusa influence |
| HRP20181272T1 (hr) | 2013-11-13 | 2018-10-05 | Vertex Pharmaceuticals Incorporated | Postupci priprave inhibitora replikacije virusa influence |
| WO2015161285A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic lactams for use in the protection of hematopoietic stem and progenitor cells against ionizing radiation |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| WO2016040858A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| JP6857617B2 (ja) | 2015-05-13 | 2021-04-14 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤 |
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| US11866409B2 (en) | 2015-11-02 | 2024-01-09 | Carmel-Haifa University Economic Corporation Ltd. | Apoptosis related protein in the tgf-beta signaling pathway (ARTS) mimetic compounds, compositions, methods and uses thereof in induction of differentiation and/or apoptosis of premalignant and malignant cells, thereby restoring their normal-like phenotype |
| GB201521059D0 (en) | 2015-11-30 | 2016-01-13 | Isis Innovation | Inhibitors of metallo-beta-lactamases |
| EP3565558B1 (en) | 2017-01-06 | 2023-12-06 | G1 Therapeutics, Inc. | Combination therapy with a serd compound and a cdk4/6 inhibitor for the treatment of cancer |
| FI3645001T3 (fi) | 2017-06-29 | 2024-09-25 | G1 Therapeutics Inc | Git38:n morfisia muotoja ja niiden valmistusmenetelmiä |
| RS67557B1 (sr) | 2018-08-24 | 2026-01-30 | Pharmacosmos Holding As | Unapređena sinteza 1,4-diazaspiro[5.5]undekan-3-ona |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| US12404261B2 (en) * | 2020-12-22 | 2025-09-02 | Novartis Ag | Compounds and compositions for treating conditions associated with cGAS |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US105140A (en) * | 1870-07-05 | Improvement in cigar-wrapping machines | ||
| DE2005845A1 (de) * | 1969-02-12 | 1970-09-03 | Sumitomo Chemical Company, Ltd., Osaka (Japan) | Verfahren zur Herstellung von Benzodiazepinen und ihren Salzen |
| AR205437A1 (es) * | 1972-09-25 | 1976-05-07 | Hoffmann La Roche | Procedimiento para la preparacion de derivados de indoloquinolinona |
| CA1012147A (en) * | 1972-09-25 | 1977-06-14 | Hoffmann-La Roche Limited | Indolo quinoline derivatives |
| US4225711A (en) * | 1978-10-02 | 1980-09-30 | Schering Corporation | Substituted 2-[(methylsulfinyl)acetyl]-3-heterocyclicindoles and their use as immunosuppressants |
| CA2038925A1 (en) * | 1990-03-26 | 1991-09-27 | Takashi Sohda | Indole derivatives, their production and use |
| JPH04211651A (ja) * | 1990-03-26 | 1992-08-03 | Takeda Chem Ind Ltd | 骨吸収抑制剤およびインドール誘導体 |
| GB9319100D0 (en) * | 1993-09-15 | 1993-11-03 | Pfizer Ltd | 3-(3-pyridinyl)h-indoles |
| JP2001122855A (ja) * | 1999-10-27 | 2001-05-08 | Japan Tobacco Inc | インドール化合物及びその医薬用途 |
| US6323228B1 (en) * | 2000-09-15 | 2001-11-27 | Abbott Laboratories | 3-substituted indole angiogenesis inhibitors |
| WO2002102301A2 (en) * | 2000-12-07 | 2002-12-27 | Cytovia, Inc. | Substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| JP4279561B2 (ja) * | 2001-05-23 | 2009-06-17 | メルク フロスト カナダ リミテツド | プロスタグランジンＤ２受容体拮抗薬としてのジヒドロピロロ［１，２−ａ］インドールおよびテトラヒドロピリド［１，２−ａ］−インドール誘導体 |
| DE10155076A1 (de) * | 2001-11-09 | 2003-05-22 | Merck Patent Gmbh | Verwendung von Endothelin-Rezeptor-Antagonisten zur Behandlung von Tumorerkrankungen |
| US7268159B2 (en) * | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
-
2004
- 2004-04-30 IT IT000874A patent/ITMI20040874A1/it unknown
-
2005
- 2005-04-27 EP EP05743013A patent/EP1750687A2/en not_active Withdrawn
- 2005-04-27 CA CA002564249A patent/CA2564249A1/en not_active Abandoned
- 2005-04-27 JP JP2007510035A patent/JP2007535520A/ja active Pending
- 2005-04-27 US US11/579,237 patent/US20070248672A1/en not_active Abandoned
- 2005-04-27 WO PCT/EP2005/051908 patent/WO2005105213A2/en not_active Ceased
- 2005-04-27 AU AU2005237788A patent/AU2005237788A1/en not_active Abandoned
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