ZA200503231B - 3-Phenyl substituted pyridoindolone, preparation and therapeutic use thereof - Google Patents
3-Phenyl substituted pyridoindolone, preparation and therapeutic use thereof Download PDFInfo
- Publication number
- ZA200503231B ZA200503231B ZA200503231A ZA200503231A ZA200503231B ZA 200503231 B ZA200503231 B ZA 200503231B ZA 200503231 A ZA200503231 A ZA 200503231A ZA 200503231 A ZA200503231 A ZA 200503231A ZA 200503231 B ZA200503231 B ZA 200503231B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- formula
- dihydro
- phenyl
- pyrido
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- YNHGMRWHXVMPEN-UHFFFAOYSA-N pyrrolo[2,3-f]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)C=C3C=CC2=N1 YNHGMRWHXVMPEN-UHFFFAOYSA-N 0.000 title description 3
- 230000001225 therapeutic effect Effects 0.000 title description 2
- -1 hydroxyiminomethyl Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000005936 piperidyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 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 description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 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 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 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
- 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
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 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 description 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 description 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 description 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 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000007428 synaptic transmission, GABAergic Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200503231B true ZA200503231B (en) | 2006-06-28 |
Family
ID=32088223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200503231A ZA200503231B (en) | 2002-10-23 | 2005-04-21 | 3-Phenyl substituted pyridoindolone, preparation and therapeutic use thereof |
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
-
2008
- 2008-05-12 US US12/118,920 patent/US8012991B2/en not_active Expired - Lifetime
- 2008-07-29 CY CY20081100788T patent/CY1109785T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200503231B (en) | 3-Phenyl substituted pyridoindolone, preparation and therapeutic use thereof | |
| ES2360933T3 (es) | Derivados de heteroarilo condensados. | |
| US6608056B1 (en) | Fused heteroaryl derivatives | |
| EP1664032B1 (en) | N-substituted pyrazolyl-amidyl-benzimidazolyl c-kit inhibitors | |
| BR112021006905A2 (pt) | composto, sal e solvato do mesmo e agente agonístico de sting, composição farmacêutica que compreende o dito composto e uso do mesmo para suprimir a progressão de, suprimir a recorrência de e/ou tratar câncer ou doença infecciosa | |
| JP2018530539A (ja) | スルフィニルフェニル又はスルホンイミドイルフェニルベンザゼピン | |
| JP2023553835A (ja) | 大環状化合物およびそれらの使用 | |
| US20080221187A9 (en) | N-substituted pyrazolyl-amidyl-benzimidazolyl c-Kit inhibitors | |
| JP2015520186A (ja) | 増殖性疾患の治療にキナーゼ阻害剤として有用なジヒドロナフチリジン及び関連化合物 | |
| JP2004517072A (ja) | Ｃｎｓ障害の治療において有用な化合物 | |
| WO2004048330A8 (en) | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them | |
| AU2008208801A1 (en) | Purine derivatives | |
| EP1807419A1 (en) | (2-carboxamido)(3-amino) thiophene compounds | |
| NO20022124L (no) | Imidazopyridinderivater som fosfodiesterase VII-inhibitorer | |
| CA3162253A1 (en) | Inhibitors of enl/af9 yeats | |
| JP2006511498A5 (enExample) | ||
| EP2513089A1 (en) | 3-(indolyl)- or 3-(azaindolyl)-4-arylmaleimide compounds and their use in tumor treatment | |
| CA2490115A1 (en) | Arylalkyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them | |
| CN1953751A (zh) | 取代的1－苯基－1,5－二氢－吡啶并－[3,2－b]吲哚－2－酮和其它的hiv抑制剂的组合物 | |
| CN1953978B (zh) | 作为抗病毒剂的5-取代的1-苯基-1,5-二氢-吡啶并[3,2-b]吲哚-2-酮及其类似物 | |
| OA20485A (en) | IMIDAZO[4,5-C]pyridine derivatives as tolllike receptor agonsits | |
| CO5261490A1 (es) | Compuesto de anillo fusionado y uso farmaceutico del mismo |