JP2006511498A5 - - Google Patents
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- Publication number
- JP2006511498A5 JP2006511498A5 JP2004549256A JP2004549256A JP2006511498A5 JP 2006511498 A5 JP2006511498 A5 JP 2006511498A5 JP 2004549256 A JP2004549256 A JP 2004549256A JP 2004549256 A JP2004549256 A JP 2004549256A JP 2006511498 A5 JP2006511498 A5 JP 2006511498A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- dihydro
- pyrido
- phenyl
- indol
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 4
- -1 hydroxy, hydroxymethyl Chemical group 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005936 piperidyl group Chemical group 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- OBXBXDREPHLMNM-UHFFFAOYSA-N 1,6-dimethyl-3-[3-(pyridin-2-ylamino)phenyl]-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C(C=1)=CC=CC=1NC1=CC=CC=N1 OBXBXDREPHLMNM-UHFFFAOYSA-N 0.000 claims 1
- UOPPWPAWPJQPLM-UHFFFAOYSA-N 1,6-dimethyl-3-[3-(pyrimidin-2-ylamino)phenyl]-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C(C=1)=CC=CC=1NC1=NC=CC=N1 UOPPWPAWPJQPLM-UHFFFAOYSA-N 0.000 claims 1
- BXYOWBPGACEZSO-UHFFFAOYSA-N 1,6-dimethyl-3-[3-(trifluoromethyl)phenyl]-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 BXYOWBPGACEZSO-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
- KWNZLDPPJVSTOZ-UHFFFAOYSA-N 3-(1,6-dimethyl-2-oxo-9h-pyrido[2,3-b]indol-3-yl)benzonitrile Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC(C#N)=C1 KWNZLDPPJVSTOZ-UHFFFAOYSA-N 0.000 claims 1
- XGALXJUJMUEJPR-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=C(Cl)C=C1Cl XGALXJUJMUEJPR-UHFFFAOYSA-N 0.000 claims 1
- YVMLHKHLLYTELY-UHFFFAOYSA-N 3-(2,4-dimethoxyphenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound COC1=CC(OC)=CC=C1C(C(N1C)=O)=CC2=C1NC1=CC=C(C)C=C12 YVMLHKHLLYTELY-UHFFFAOYSA-N 0.000 claims 1
- OCCMDWFWUXEDEB-UHFFFAOYSA-N 3-(2,4-dimethoxyphenyl)-1,9-dimethyl-2-oxopyrido[2,3-b]indole-6-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1C(C(N1C)=O)=CC2=C1N(C)C1=CC=C(C(O)=O)C=C12 OCCMDWFWUXEDEB-UHFFFAOYSA-N 0.000 claims 1
- UOCLWKVLEWVWGN-UHFFFAOYSA-N 3-(2-anilinophenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC=C1NC1=CC=CC=C1 UOCLWKVLEWVWGN-UHFFFAOYSA-N 0.000 claims 1
- MHFNCUATIPSVOJ-UHFFFAOYSA-N 3-(3-acetylphenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound CC(=O)C1=CC=CC(C=2C(N(C)C=3NC4=CC=C(C)C=C4C=3C=2)=O)=C1 MHFNCUATIPSVOJ-UHFFFAOYSA-N 0.000 claims 1
- NDKNXKCTYKUROA-UHFFFAOYSA-N 3-(4-aminophenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=C(N)C=C1 NDKNXKCTYKUROA-UHFFFAOYSA-N 0.000 claims 1
- PMWVBWVFGYECTN-UHFFFAOYSA-N 3-(6-chloro-1,3-benzodioxol-5-yl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C(C(=C1)Cl)=CC2=C1OCO2 PMWVBWVFGYECTN-UHFFFAOYSA-N 0.000 claims 1
- WHIUBYFLQYSILN-UHFFFAOYSA-N 3-[3-(hydroxymethyl)phenyl]-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC(CO)=C1 WHIUBYFLQYSILN-UHFFFAOYSA-N 0.000 claims 1
- KJBZXISVZRELEI-UHFFFAOYSA-N 6-bromo-3-(3,5-dimethylphenyl)-1-methyl-9h-pyrido[2,3-b]indol-2-one Chemical compound CC1=CC(C)=CC(C=2C(N(C)C=3NC4=CC=C(Br)C=C4C=3C=2)=O)=C1 KJBZXISVZRELEI-UHFFFAOYSA-N 0.000 claims 1
- HICQTMQGDQCZEM-UHFFFAOYSA-N C12=CC(C)=CC=C2N2CCCN(C3=O)C2=C1C=C3C1=CC=C(Cl)C=C1Cl Chemical compound C12=CC(C)=CC=C2N2CCCN(C3=O)C2=C1C=C3C1=CC=C(Cl)C=C1Cl HICQTMQGDQCZEM-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- AEGVQQVCBQMNBE-UHFFFAOYSA-N methyl 9-(cyanomethyl)-3-(2,4-dichlorophenyl)-2-oxo-1h-pyrido[2,3-b]indole-6-carboxylate Chemical compound C=1C=2C3=CC(C(=O)OC)=CC=C3N(CC#N)C=2NC(=O)C=1C1=CC=C(Cl)C=C1Cl AEGVQQVCBQMNBE-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000004565 tumor cell growth Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- LRCWLSRBJPAEFN-UHFFFAOYSA-N 9-(3-aminopropyl)-3-(2,4-dichlorophenyl)-1,6-dimethylpyrido[2,3-b]indol-2-one hydrochloride Chemical compound CC1=CC2=C(C=C1)N(C3=C2C=C(C(=O)N3C)C4=C(C=C(C=C4)Cl)Cl)CCCN.Cl LRCWLSRBJPAEFN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 1
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 1
- YONVOJHDRVGOHS-UHFFFAOYSA-N 2-[3-[3-(2,4-dichlorophenyl)-1,6-dimethyl-2-oxopyrido[2,3-b]indol-9-yl]propyl]isoindole-1,3-dione Chemical compound C=1C=2C3=CC(C)=CC=C3N(CCCN3C(C4=CC=CC=C4C3=O)=O)C=2N(C)C(=O)C=1C1=CC=C(Cl)C=C1Cl YONVOJHDRVGOHS-UHFFFAOYSA-N 0.000 description 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0213264A FR2846329B1 (fr) | 2002-10-23 | 2002-10-23 | Derives de pyridoindolone substitues en -3 par un phenyle, leur preparation et leur application en therapeutique |
| PCT/FR2003/003110 WO2004041817A1 (fr) | 2002-10-23 | 2003-10-21 | Derives de pyridoindolone substitues en -3 par un phenyle, leur preparation et leur application en therapeutique. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006511498A JP2006511498A (ja) | 2006-04-06 |
| JP2006511498A5 true JP2006511498A5 (enExample) | 2009-07-02 |
| JP4488899B2 JP4488899B2 (ja) | 2010-06-23 |
Family
ID=32088223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004549256A Expired - Fee Related JP4488899B2 (ja) | 2002-10-23 | 2003-10-21 | ３−フェニル置換ピリドインドロン、それらの製造方法および治療用途 |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US7390818B2 (enExample) |
| EP (1) | EP1556382B1 (enExample) |
| JP (1) | JP4488899B2 (enExample) |
| KR (1) | KR101051859B1 (enExample) |
| CN (1) | CN100345850C (enExample) |
| AR (1) | AR041689A1 (enExample) |
| AT (1) | ATE396994T1 (enExample) |
| AU (1) | AU2003296769B2 (enExample) |
| BR (1) | BR0314883A (enExample) |
| CA (1) | CA2502769C (enExample) |
| CY (1) | CY1109785T1 (enExample) |
| DE (1) | DE60321372D1 (enExample) |
| DK (1) | DK1556382T3 (enExample) |
| EA (1) | EA010833B1 (enExample) |
| ES (1) | ES2304546T3 (enExample) |
| FR (1) | FR2846329B1 (enExample) |
| HR (1) | HRP20050362B1 (enExample) |
| IL (1) | IL168133A (enExample) |
| IS (1) | IS2641B (enExample) |
| MA (1) | MA27455A1 (enExample) |
| ME (1) | ME00102B (enExample) |
| MX (1) | MXPA05004349A (enExample) |
| NO (1) | NO331297B1 (enExample) |
| NZ (1) | NZ539866A (enExample) |
| PL (1) | PL214867B1 (enExample) |
| PT (1) | PT1556382E (enExample) |
| RS (1) | RS51605B (enExample) |
| SI (1) | SI1556382T1 (enExample) |
| TW (1) | TWI325864B (enExample) |
| UA (1) | UA79317C2 (enExample) |
| WO (1) | WO2004041817A1 (enExample) |
| ZA (1) | ZA200503231B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2823975B1 (fr) | 2001-04-27 | 2003-05-30 | Sanofi Synthelabo | Nouvelle utilisation de pyridoindolone |
| US7456193B2 (en) | 2002-10-23 | 2008-11-25 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics |
| US20100297252A1 (en) | 2003-03-03 | 2010-11-25 | Elan Pharma International Ltd. | Nanoparticulate meloxicam formulations |
| US8512727B2 (en) * | 2003-03-03 | 2013-08-20 | Alkermes Pharma Ireland Limited | Nanoparticulate meloxicam formulations |
| FR2869316B1 (fr) * | 2004-04-21 | 2006-06-02 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -6, leur preparation et leur application en therapeutique. |
| FR2876377B1 (fr) * | 2004-10-11 | 2007-03-16 | Univ Claude Bernard Lyon | Nouveaux derives de 9h-pyrido[2,3-b]indole, leur procede de preparation, ainsi que les compositions pharmaceutiques contenant de tels composes |
| FR2892416B1 (fr) * | 2005-10-20 | 2008-06-27 | Sanofi Aventis Sa | Derives de 6-heteroarylpyridoindolone, leur preparation et leur application en therapeutique |
| FR2945950A1 (fr) | 2009-05-27 | 2010-12-03 | Elan Pharma Int Ltd | Compositions de nanoparticules anticancereuses et procedes pour les preparer |
| FR2959133A1 (fr) | 2010-04-22 | 2011-10-28 | Sanofi Aventis | Formulation pharmaceutique anticancereuse |
| HUE032426T2 (en) | 2009-05-27 | 2017-09-28 | Alkermes Pharma Ireland Ltd | Inhibition of flake aggregation in nanoparticulate meloxicam formulations |
| CN107459481A (zh) * | 2017-07-25 | 2017-12-12 | 广州大学 | 一种3‑（4‑甲氧基苯基）‑6‑甲氧基‑4‑氯‑5,7‑二溴喹啉的合成方法 |
| EP3919492A4 (en) * | 2019-02-01 | 2022-11-09 | Medshine Discovery Inc. | TRICYCLIC COMPOUND CONTAINING PYRIMIDINYL GROUP AS C-MET INHIBITOR |
| CN113329276B (zh) | 2020-02-28 | 2022-10-28 | 华为技术有限公司 | 数据传输方法、装置、网关、芯片及存储介质 |
| CN116171156B (zh) * | 2020-07-31 | 2025-07-04 | 江苏奥赛康药业有限公司 | 含嘧啶基团的三并环类化合物的盐型、晶型及其制备方法 |
| US20240132446A1 (en) * | 2021-05-26 | 2024-04-25 | Refined Technologies, Inc. | Compositions and methods for removal of n-methyl-2-pyrrolidone (nmp) degradation products and other foulants from nmp purification systems |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268772A (en) | 1968-03-15 | 1972-03-29 | Glaxo Lab Ltd | NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME |
| US4263304A (en) * | 1978-06-05 | 1981-04-21 | Sumitomo Chemical Company, Limited | 7 H-indolo[2,3-c]isoquinolines |
| SU833971A1 (ru) | 1979-07-10 | 1981-05-30 | Ленинградский Химико-Фармацевтическийинститут | Способ получени 3-фенил-2-оксо- - КАРбОлиНОВ |
| FR2595701B1 (fr) * | 1986-03-17 | 1988-07-01 | Sanofi Sa | Derives du pyrido-indole, leur application a titre de medicaments et les compositions les renfermant |
| JPH10501686A (ja) | 1994-04-13 | 1998-02-17 | ザ ロックフェラー ユニヴァーシティ | 神経系の細胞へのｄｎａのａａｖ仲介送達 |
| DE19502753A1 (de) * | 1995-01-23 | 1996-07-25 | Schering Ag | Neue 9H-Pyrido[3,4-b]indol-Derivate |
| FR2765582B1 (fr) | 1997-07-03 | 1999-08-06 | Synthelabo | Derives de 3-alkyl-1,9-dihydro-2h-pyrido[2,3-b]indol-2-one leur preparation et leur application en therapeutique |
| FR2765581B1 (fr) * | 1997-07-03 | 1999-08-06 | Synthelabo | Derives de 3-aryl-1,9-dihydro-2h-pyrido[2,3-b]indol-2-one, leur preparation et leur application en therapeutique |
| CA2326319A1 (en) | 1998-04-02 | 1999-10-14 | Neurogen Corporation | Aminoalkyl substituted 5,6,7,8-tetrahydro-9h pyrimidino[2,3-b]indole and 5,6,7,8-tetrahydro-9h-pyrimidino[4,5-b]indole derivatives: crf1 specific ligands |
| IT1313592B1 (it) * | 1999-08-03 | 2002-09-09 | Novuspharma Spa | Derivati di 1h-pirido 3,4-b indol-1-one. |
| US20020156016A1 (en) | 2001-03-30 | 2002-10-24 | Gerald Minuk | Control of cell growth by altering cell membrane potentials |
| FR2823975B1 (fr) * | 2001-04-27 | 2003-05-30 | Sanofi Synthelabo | Nouvelle utilisation de pyridoindolone |
| FR2846330B1 (fr) | 2002-10-23 | 2004-12-03 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -3 par groupe heterocyclique, leur preparation et leur application en therapeutique |
| US7456193B2 (en) * | 2002-10-23 | 2008-11-25 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics |
| FR2869316B1 (fr) | 2004-04-21 | 2006-06-02 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -6, leur preparation et leur application en therapeutique. |
| FR2892416B1 (fr) | 2005-10-20 | 2008-06-27 | Sanofi Aventis Sa | Derives de 6-heteroarylpyridoindolone, leur preparation et leur application en therapeutique |
-
2002
- 2002-10-23 FR FR0213264A patent/FR2846329B1/fr not_active Expired - Fee Related
-
2003
- 2003-10-21 HR HRP20050362AA patent/HRP20050362B1/hr not_active IP Right Cessation
- 2003-10-21 MX MXPA05004349A patent/MXPA05004349A/es active IP Right Grant
- 2003-10-21 JP JP2004549256A patent/JP4488899B2/ja not_active Expired - Fee Related
- 2003-10-21 BR BR0314883-1A patent/BR0314883A/pt not_active IP Right Cessation
- 2003-10-21 CN CNB2003801072280A patent/CN100345850C/zh not_active Expired - Fee Related
- 2003-10-21 DE DE60321372T patent/DE60321372D1/de not_active Expired - Lifetime
- 2003-10-21 EP EP03810495A patent/EP1556382B1/fr not_active Expired - Lifetime
- 2003-10-21 EA EA200500521A patent/EA010833B1/ru not_active IP Right Cessation
- 2003-10-21 KR KR20057006949A patent/KR101051859B1/ko not_active Expired - Fee Related
- 2003-10-21 PT PT03810495T patent/PT1556382E/pt unknown
- 2003-10-21 NZ NZ539866A patent/NZ539866A/en not_active IP Right Cessation
- 2003-10-21 ES ES03810495T patent/ES2304546T3/es not_active Expired - Lifetime
- 2003-10-21 AT AT03810495T patent/ATE396994T1/de active
- 2003-10-21 DK DK03810495T patent/DK1556382T3/da active
- 2003-10-21 UA UAA200503772A patent/UA79317C2/uk unknown
- 2003-10-21 SI SI200331333T patent/SI1556382T1/sl unknown
- 2003-10-21 CA CA2502769A patent/CA2502769C/en not_active Expired - Fee Related
- 2003-10-21 AU AU2003296769A patent/AU2003296769B2/en not_active Ceased
- 2003-10-21 ME MEP-2008-222A patent/ME00102B/me unknown
- 2003-10-21 RS YU20050362A patent/RS51605B/sr unknown
- 2003-10-21 PL PL376790A patent/PL214867B1/pl unknown
- 2003-10-21 WO PCT/FR2003/003110 patent/WO2004041817A1/fr not_active Ceased
- 2003-10-22 AR ARP030103840A patent/AR041689A1/es unknown
- 2003-10-23 TW TW092129440A patent/TWI325864B/zh not_active IP Right Cessation
-
2005
- 2005-04-19 US US11/109,068 patent/US7390818B2/en not_active Expired - Lifetime
- 2005-04-19 MA MA28228A patent/MA27455A1/fr unknown
- 2005-04-19 IL IL168133A patent/IL168133A/en not_active IP Right Cessation
- 2005-04-20 IS IS7815A patent/IS2641B/is unknown
- 2005-04-21 ZA ZA200503231A patent/ZA200503231B/en unknown
- 2005-04-22 NO NO20051983A patent/NO331297B1/no not_active IP Right Cessation
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2008
- 2008-05-12 US US12/118,920 patent/US8012991B2/en not_active Expired - Lifetime
- 2008-07-29 CY CY20081100788T patent/CY1109785T1/el unknown
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