DE60304596T2 - In 3-position heterocyclisch substituierte pyridoindolonderivate, ihre herstellung und ihre therapeutische verwendung - Google Patents
In 3-position heterocyclisch substituierte pyridoindolonderivate, ihre herstellung und ihre therapeutische verwendung Download PDFInfo
- Publication number
- DE60304596T2 DE60304596T2 DE60304596T DE60304596T DE60304596T2 DE 60304596 T2 DE60304596 T2 DE 60304596T2 DE 60304596 T DE60304596 T DE 60304596T DE 60304596 T DE60304596 T DE 60304596T DE 60304596 T2 DE60304596 T2 DE 60304596T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- indol
- pyrido
- dihydro
- 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.)
- Expired - Lifetime
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- 238000002360 preparation method Methods 0.000 title claims description 22
- 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 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 97
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- -1 N-oxidopyridyl Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001041 indolyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
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- 125000002541 furyl group Chemical group 0.000 claims description 5
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- WJRBFFNOZCHACV-UHFFFAOYSA-N 3-(1-benzothiophen-5-yl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C1=C2SC=CC2=CC(C=2C(=O)N(C)C=3NC4=CC=C(C=C4C=3C=2)C)=C1 WJRBFFNOZCHACV-UHFFFAOYSA-N 0.000 claims description 3
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- DYFRQOGYSMSLER-UHFFFAOYSA-N 3-(2,6-dimethoxypyridin-4-yl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound COC1=NC(OC)=CC(C=2C(N(C)C=3NC4=CC=C(C)C=C4C=3C=2)=O)=C1 DYFRQOGYSMSLER-UHFFFAOYSA-N 0.000 claims description 3
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- OXKUGUNOYLYMMT-UHFFFAOYSA-N methyl 2-(3-chloropyridin-4-yl)acetate Chemical compound COC(=O)CC1=CC=NC=C1Cl OXKUGUNOYLYMMT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- 201000005987 myeloid sarcoma Diseases 0.000 description 1
- FNNWEHZGFLTFFV-UHFFFAOYSA-N n,5-dimethyl-1h-indol-2-amine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=C2NC(NC)=CC2=C1 FNNWEHZGFLTFFV-UHFFFAOYSA-N 0.000 description 1
- CCGKDXITQVRPNY-UHFFFAOYSA-N n-dianilinophosphinothioylaniline Chemical compound C=1C=CC=CC=1NP(NC=1C=CC=CC=1)(=S)NC1=CC=CC=C1 CCGKDXITQVRPNY-UHFFFAOYSA-N 0.000 description 1
- CSPUMYYMBHFYNX-UHFFFAOYSA-N n-methyl-n'-(4-methylphenyl)acetohydrazide Chemical compound CC(=O)N(C)NC1=CC=C(C)C=C1 CSPUMYYMBHFYNX-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 201000006958 oropharynx cancer Diseases 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 201000002511 pituitary cancer Diseases 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
- 229960000624 procarbazine Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000006825 purine synthesis Effects 0.000 description 1
- 230000006824 pyrimidine synthesis Effects 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000011110 re-filtration Methods 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 229960003440 semustine Drugs 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 201000002314 small intestine cancer Diseases 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007428 synaptic transmission, GABAergic Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 229940063683 taxotere Drugs 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
- 201000003120 testicular cancer Diseases 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229960003433 thalidomide Drugs 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000003741 urothelium Anatomy 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0213270 | 2002-10-23 | ||
| FR0213270A FR2846330B1 (fr) | 2002-10-23 | 2002-10-23 | Derives de pyridoindolone substitues en -3 par groupe heterocyclique, leur preparation et leur application en therapeutique |
| PCT/FR2003/003111 WO2004037821A1 (fr) | 2002-10-23 | 2003-10-21 | Derives de pyridoindolone substitues en -3 par un groupe heterocyclique, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60304596D1 DE60304596D1 (de) | 2006-05-24 |
| DE60304596T2 true DE60304596T2 (de) | 2007-05-10 |
Family
ID=32088226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60304596T Expired - Lifetime DE60304596T2 (de) | 2002-10-23 | 2003-10-21 | In 3-position heterocyclisch substituierte pyridoindolonderivate, ihre herstellung und ihre therapeutische verwendung |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1556380B1 (enExample) |
| JP (1) | JP4599164B2 (enExample) |
| AR (1) | AR041690A1 (enExample) |
| AT (1) | ATE323091T1 (enExample) |
| AU (1) | AU2003292285A1 (enExample) |
| CY (1) | CY1105158T1 (enExample) |
| DE (1) | DE60304596T2 (enExample) |
| DK (1) | DK1556380T3 (enExample) |
| ES (1) | ES2263033T3 (enExample) |
| FR (1) | FR2846330B1 (enExample) |
| PT (1) | PT1556380E (enExample) |
| TW (1) | TW200418853A (enExample) |
| WO (1) | WO2004037821A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2823975B1 (fr) | 2001-04-27 | 2003-05-30 | Sanofi Synthelabo | Nouvelle utilisation de pyridoindolone |
| FR2846329B1 (fr) | 2002-10-23 | 2004-12-03 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -3 par un phenyle, leur preparation et leur application en therapeutique |
| 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 |
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4263304A (en) * | 1978-06-05 | 1981-04-21 | Sumitomo Chemical Company, Limited | 7 H-indolo[2,3-c]isoquinolines |
| 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 |
-
2002
- 2002-10-23 FR FR0213270A patent/FR2846330B1/fr not_active Expired - Fee Related
-
2003
- 2003-10-21 DE DE60304596T patent/DE60304596T2/de not_active Expired - Lifetime
- 2003-10-21 WO PCT/FR2003/003111 patent/WO2004037821A1/fr not_active Ceased
- 2003-10-21 PT PT03767851T patent/PT1556380E/pt unknown
- 2003-10-21 ES ES03767851T patent/ES2263033T3/es not_active Expired - Lifetime
- 2003-10-21 AU AU2003292285A patent/AU2003292285A1/en not_active Abandoned
- 2003-10-21 DK DK03767851T patent/DK1556380T3/da active
- 2003-10-21 JP JP2004546105A patent/JP4599164B2/ja not_active Expired - Fee Related
- 2003-10-21 EP EP03767851A patent/EP1556380B1/fr not_active Expired - Lifetime
- 2003-10-21 AT AT03767851T patent/ATE323091T1/de active
- 2003-10-22 AR ARP030103841A patent/AR041690A1/es unknown
- 2003-10-22 TW TW092129284A patent/TW200418853A/zh unknown
-
2006
- 2006-07-12 CY CY20061100971T patent/CY1105158T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE323091T1 (de) | 2006-04-15 |
| AR041690A1 (es) | 2005-05-26 |
| DK1556380T3 (da) | 2006-08-14 |
| CY1105158T1 (el) | 2010-03-03 |
| JP4599164B2 (ja) | 2010-12-15 |
| AU2003292285A1 (en) | 2004-05-13 |
| FR2846330A1 (fr) | 2004-04-30 |
| JP2006505577A (ja) | 2006-02-16 |
| FR2846330B1 (fr) | 2004-12-03 |
| ES2263033T3 (es) | 2006-12-01 |
| DE60304596D1 (de) | 2006-05-24 |
| TW200418853A (en) | 2004-10-01 |
| EP1556380B1 (fr) | 2006-04-12 |
| EP1556380A1 (fr) | 2005-07-27 |
| WO2004037821A1 (fr) | 2004-05-06 |
| PT1556380E (pt) | 2006-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |