CA2526663C - Derives indoliques possedant une activite d'induction de l'apoptose - Google Patents
Derives indoliques possedant une activite d'induction de l'apoptose Download PDFInfo
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- CA2526663C CA2526663C CA2526663A CA2526663A CA2526663C CA 2526663 C CA2526663 C CA 2526663C CA 2526663 A CA2526663 A CA 2526663A CA 2526663 A CA2526663 A CA 2526663A CA 2526663 C CA2526663 C CA 2526663C
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- Prior art keywords
- tautomer
- stereoisomer
- indole derivative
- substituted
- physiologically tolerated
- 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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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
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- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 206010063344 microscopic polyangiitis Diseases 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 208000013371 ovarian adenocarcinoma Diseases 0.000 description 1
- 201000006588 ovary adenocarcinoma Diseases 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical compound OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 231100000588 tumorigenic Toxicity 0.000 description 1
- 230000000381 tumorigenic effect Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47627703P | 2003-06-05 | 2003-06-05 | |
| US60/476,277 | 2003-06-05 | ||
| EP03012868A EP1484329A1 (fr) | 2003-06-06 | 2003-06-06 | Dérivés d'indole déstinés à l'induction d'apoptose |
| EP03012868.0 | 2003-06-06 | ||
| EP04011598.2 | 2004-05-15 | ||
| EP04011598A EP1595878A1 (fr) | 2004-05-15 | 2004-05-15 | Derives d'indole destines a l'induction d'apoptose |
| PCT/EP2004/005593 WO2004108702A1 (fr) | 2003-06-05 | 2004-05-25 | Derives indoliques possedant une activite d'induction de l'apoptose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2526663A1 CA2526663A1 (fr) | 2004-12-16 |
| CA2526663C true CA2526663C (fr) | 2011-07-19 |
Family
ID=43661564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2526663A Expired - Fee Related CA2526663C (fr) | 2003-06-05 | 2004-05-25 | Derives indoliques possedant une activite d'induction de l'apoptose |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1641777A1 (fr) |
| JP (1) | JP4878285B2 (fr) |
| KR (1) | KR101132599B1 (fr) |
| CN (1) | CN1816543B (fr) |
| AU (1) | AU2004245198B2 (fr) |
| BR (1) | BRPI0410998A (fr) |
| CA (1) | CA2526663C (fr) |
| MX (1) | MXPA05013121A (fr) |
| NZ (1) | NZ543853A (fr) |
| RS (1) | RS20050901A (fr) |
| RU (1) | RU2327696C2 (fr) |
| WO (1) | WO2004108702A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2628039A1 (fr) * | 2005-11-11 | 2007-05-18 | Aeterna Zentaris Gmbh | Nouvelle pyridopyrazine et son utilisation pour la modulation de kinases |
| US8217042B2 (en) | 2005-11-11 | 2012-07-10 | Zentaris Gmbh | Pyridopyrazines and their use as modulators of kinases |
| EP1790342A1 (fr) | 2005-11-11 | 2007-05-30 | Zentaris GmbH | Dérivés de pyridopyrazine et leur utilisation comme modulateurs de transduction de signal |
| AU2006318212C1 (en) | 2005-11-23 | 2012-08-30 | The Board Of Regents Of The University Of Texas System | Oncogenic ras-specific cytotoxic compound and methods of use thereof |
| SG176477A1 (en) * | 2006-08-07 | 2011-12-29 | Ironwood Pharmaceuticals Inc | Indole compounds |
| EP2091532A1 (fr) * | 2006-11-28 | 2009-08-26 | Ziopharm Oncology, Inc. | Utilisation de dérivés d'acide indolyl-3-glyoxylique comprenant de l'indibuline, seuls ou combinés à d'autres agents, pour traiter le cancer |
| PL2349259T3 (pl) * | 2008-10-16 | 2016-07-29 | Array Biopharma Inc | Inhibitory mitozy do zwiększania apoptozy w terapii |
| WO2012017325A2 (fr) * | 2010-07-19 | 2012-02-09 | Procaps Sa | Dispositif et procédé pour encapsuler des microparticules avec du liquide dans des capsules molles |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9216009D0 (en) * | 1992-07-28 | 1992-09-09 | Almirall Lab | New indol derivatives |
| DE19814838C2 (de) * | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| TWI269654B (en) * | 1999-09-28 | 2007-01-01 | Baxter Healthcare Sa | N-substituted indole-3-glyoxylamide compounds having anti-tumor action |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| IT1318641B1 (it) * | 2000-07-25 | 2003-08-27 | Novuspharma Spa | Ammidi di acidi 2-(1h-indol-3-il)-2-oxo-acetici ad attivita'antitumorale. |
| DE10037310A1 (de) * | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
| EP1427416A2 (fr) * | 2001-09-13 | 2004-06-16 | Synta Pharmaceuticals Corporation | 3-glyoxlylamide-indoles pour traitement du cancer |
-
2004
- 2004-05-25 NZ NZ543853A patent/NZ543853A/en not_active IP Right Cessation
- 2004-05-25 WO PCT/EP2004/005593 patent/WO2004108702A1/fr not_active Ceased
- 2004-05-25 CA CA2526663A patent/CA2526663C/fr not_active Expired - Fee Related
- 2004-05-25 KR KR1020057023347A patent/KR101132599B1/ko not_active Expired - Fee Related
- 2004-05-25 BR BRPI0410998-8A patent/BRPI0410998A/pt not_active IP Right Cessation
- 2004-05-25 RU RU2006100022/04A patent/RU2327696C2/ru not_active IP Right Cessation
- 2004-05-25 CN CN2004800192716A patent/CN1816543B/zh not_active Expired - Fee Related
- 2004-05-25 AU AU2004245198A patent/AU2004245198B2/en not_active Ceased
- 2004-05-25 JP JP2006508197A patent/JP4878285B2/ja not_active Expired - Fee Related
- 2004-05-25 RS YUP-2005/0901A patent/RS20050901A/sr unknown
- 2004-05-25 MX MXPA05013121A patent/MXPA05013121A/es active IP Right Grant
- 2004-05-25 EP EP04734662A patent/EP1641777A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004245198A1 (en) | 2004-12-16 |
| NZ543853A (en) | 2009-09-25 |
| KR101132599B1 (ko) | 2012-06-21 |
| JP4878285B2 (ja) | 2012-02-15 |
| JP2007523850A (ja) | 2007-08-23 |
| CN1816543B (zh) | 2011-01-19 |
| BRPI0410998A (pt) | 2006-07-04 |
| CA2526663A1 (fr) | 2004-12-16 |
| RU2327696C2 (ru) | 2008-06-27 |
| EP1641777A1 (fr) | 2006-04-05 |
| WO2004108702A1 (fr) | 2004-12-16 |
| MXPA05013121A (es) | 2006-03-17 |
| AU2004245198B2 (en) | 2009-04-23 |
| RS20050901A (sr) | 2007-12-31 |
| RU2006100022A (ru) | 2006-05-27 |
| CN1816543A (zh) | 2006-08-09 |
| KR20060034230A (ko) | 2006-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140527 |