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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (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 (https=) |
| EP (1) | EP1556382B1 (https=) |
| JP (1) | JP4488899B2 (https=) |
| KR (1) | KR101051859B1 (https=) |
| CN (1) | CN100345850C (https=) |
| AR (1) | AR041689A1 (https=) |
| AT (1) | ATE396994T1 (https=) |
| AU (1) | AU2003296769B2 (https=) |
| BR (1) | BR0314883A (https=) |
| CA (1) | CA2502769C (https=) |
| CY (1) | CY1109785T1 (https=) |
| DE (1) | DE60321372D1 (https=) |
| DK (1) | DK1556382T3 (https=) |
| EA (1) | EA010833B1 (https=) |
| ES (1) | ES2304546T3 (https=) |
| FR (1) | FR2846329B1 (https=) |
| HR (1) | HRP20050362B1 (https=) |
| IL (1) | IL168133A (https=) |
| IS (1) | IS2641B (https=) |
| MA (1) | MA27455A1 (https=) |
| ME (1) | ME00102B (https=) |
| MX (1) | MXPA05004349A (https=) |
| NO (1) | NO331297B1 (https=) |
| NZ (1) | NZ539866A (https=) |
| PL (1) | PL214867B1 (https=) |
| PT (1) | PT1556382E (https=) |
| RS (1) | RS51605B (https=) |
| SI (1) | SI1556382T1 (https=) |
| TW (1) | TWI325864B (https=) |
| UA (1) | UA79317C2 (https=) |
| WO (1) | WO2004041817A1 (https=) |
| ZA (1) | ZA200503231B (https=) |
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 |
| HUE032426T2 (en) | 2009-05-27 | 2017-09-28 | Alkermes Pharma Ireland Ltd | Inhibition of flake aggregation in nanoparticulate meloxicam formulations |
| FR2959133A1 (fr) | 2010-04-22 | 2011-10-28 | Sanofi Aventis | Formulation pharmaceutique anticancereuse |
| FR2945950A1 (fr) | 2009-05-27 | 2010-12-03 | Elan Pharma Int Ltd | Compositions de nanoparticules anticancereuses et procedes pour les preparer |
| 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 |
| CN113365997B (zh) * | 2019-02-01 | 2022-06-07 | 南京明德新药研发有限公司 | 作为c-Met抑制剂的含嘧啶基团的三并环类化合物 |
| 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 |
| WO2022022687A1 (zh) * | 2020-07-31 | 2022-02-03 | 南京明德新药研发有限公司 | 含嘧啶基团的三并环类化合物的盐型、晶型及其制备方法 |
| CA3221565A1 (en) | 2021-05-26 | 2022-12-01 | 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 |
| CA2187626C (en) | 1994-04-13 | 2009-11-03 | Michael G. Kaplitt | Aav-mediated delivery of dna to cells of the nervous system |
| DE19502753A1 (de) * | 1995-01-23 | 1996-07-25 | Schering Ag | Neue 9H-Pyrido[3,4-b]indol-Derivate |
| 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 |
| 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 |
| JP2002510686A (ja) | 1998-04-02 | 2002-04-09 | ニューロゲン コーポレイション | アミノアルキルで置換された５，６，７，８−テトラヒドロ−９Ｈ−ピリジノ［２，３−ｂ］インドール及び５，６，７，８−テトラヒドロ−９Ｈピリミジノ［４，５−Ｂ］インドール誘導体：ＣＲＦ１特異的配位子 |
| 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 EP EP03810495A patent/EP1556382B1/fr not_active Expired - Lifetime
- 2003-10-21 ME MEP-2008-222A patent/ME00102B/me unknown
- 2003-10-21 AT AT03810495T patent/ATE396994T1/de active
- 2003-10-21 SI SI200331333T patent/SI1556382T1/sl unknown
- 2003-10-21 WO PCT/FR2003/003110 patent/WO2004041817A1/fr not_active Ceased
- 2003-10-21 JP JP2004549256A patent/JP4488899B2/ja not_active Expired - Fee Related
- 2003-10-21 PL PL376790A patent/PL214867B1/pl unknown
- 2003-10-21 BR BR0314883-1A patent/BR0314883A/pt not_active IP Right Cessation
- 2003-10-21 AU AU2003296769A patent/AU2003296769B2/en not_active Ceased
- 2003-10-21 CN CNB2003801072280A patent/CN100345850C/zh not_active Expired - Fee Related
- 2003-10-21 MX MXPA05004349A patent/MXPA05004349A/es active IP Right Grant
- 2003-10-21 ES ES03810495T patent/ES2304546T3/es not_active Expired - Lifetime
- 2003-10-21 RS YU20050362A patent/RS51605B/sr unknown
- 2003-10-21 PT PT03810495T patent/PT1556382E/pt unknown
- 2003-10-21 UA UAA200503772A patent/UA79317C2/uk unknown
- 2003-10-21 NZ NZ539866A patent/NZ539866A/en not_active IP Right Cessation
- 2003-10-21 EA EA200500521A patent/EA010833B1/ru not_active IP Right Cessation
- 2003-10-21 DE DE60321372T patent/DE60321372D1/de not_active Expired - Lifetime
- 2003-10-21 KR KR20057006949A patent/KR101051859B1/ko not_active Expired - Fee Related
- 2003-10-21 DK DK03810495T patent/DK1556382T3/da active
- 2003-10-21 CA CA2502769A patent/CA2502769C/en not_active Expired - Fee Related
- 2003-10-22 AR ARP030103840A patent/AR041689A1/es unknown
- 2003-10-23 TW TW092129440A patent/TWI325864B/zh not_active IP Right Cessation
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2005
- 2005-04-19 IL IL168133A patent/IL168133A/en not_active IP Right Cessation
- 2005-04-19 US US11/109,068 patent/US7390818B2/en not_active Expired - Lifetime
- 2005-04-19 MA MA28228A patent/MA27455A1/fr unknown
- 2005-04-20 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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