ZA200406613B - Novel 1,2,3-substituted indolizine derivatives, inhibitors of FGFS, method for making same and pharmaceutical compositions containing same - Google Patents
Novel 1,2,3-substituted indolizine derivatives, inhibitors of FGFS, method for making same and pharmaceutical compositions containing same Download PDFInfo
- Publication number
- ZA200406613B ZA200406613B ZA200406613A ZA200406613A ZA200406613B ZA 200406613 B ZA200406613 B ZA 200406613B ZA 200406613 A ZA200406613 A ZA 200406613A ZA 200406613 A ZA200406613 A ZA 200406613A ZA 200406613 B ZA200406613 B ZA 200406613B
- Authority
- ZA
- South Africa
- Prior art keywords
- radical
- alk
- carbon atoms
- formula
- compounds
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title 1
- 239000003112 inhibitor Chemical class 0.000 title 1
- -1 alkoxy radical Chemical class 0.000 claims description 113
- 150000003254 radicals Chemical class 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 98
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 238000007127 saponification reaction Methods 0.000 claims description 15
- 229920001577 copolymer Chemical class 0.000 claims description 14
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
- 230000029936 alkylation Effects 0.000 claims description 10
- 238000005804 alkylation reaction Methods 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 150000002478 indolizines Chemical class 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000010934 O-alkylation reaction Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 3
- 201000009030 Carcinoma Diseases 0.000 claims 2
- 206010008723 Chondrodystrophy Diseases 0.000 claims 2
- 208000008919 achondroplasia Diseases 0.000 claims 2
- 201000010072 hypochondroplasia Diseases 0.000 claims 2
- 201000003896 thanatophoric dysplasia Diseases 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- NZTABBRFNHSRFK-UHFFFAOYSA-N (4-amino-3-methoxyphenyl)-[1-[(3-methoxyphenyl)methoxy]-2-methylindolizin-3-yl]methanone Chemical group COC1=CC=CC(COC2=C3C=CC=CN3C(C(=O)C=3C=C(OC)C(N)=CC=3)=C2C)=C1 NZTABBRFNHSRFK-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 238000007737 ion beam deposition Methods 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 229940124639 Selective inhibitor Drugs 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical class [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical class [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 1
- 102000055025 Adenosine deaminases Human genes 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 1
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 1
- 102000003971 Fibroblast Growth Factor 1 Human genes 0.000 description 1
- 108090000386 Fibroblast Growth Factor 1 Proteins 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000003424 uricosuric effect Effects 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0204220A FR2838123B1 (fr) | 2002-04-04 | 2002-04-04 | Nouveaux derives d'indolozine-1,2,3 substituee, inhibiteurs selectifs du b-fgf |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200406613B true ZA200406613B (en) | 2007-12-27 |
Family
ID=28052118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200406613A ZA200406613B (en) | 2002-04-04 | 2003-04-02 | Novel 1,2,3-substituted indolizine derivatives, inhibitors of FGFS, method for making same and pharmaceutical compositions containing same |
Country Status (34)
| Country | Link |
|---|---|
| US (2) | US7442708B2 (es) |
| EP (1) | EP1495023B1 (es) |
| JP (1) | JP4741799B2 (es) |
| KR (1) | KR101022138B1 (es) |
| CN (1) | CN100413863C (es) |
| AR (1) | AR040404A1 (es) |
| AT (1) | ATE304013T1 (es) |
| AU (1) | AU2003240984B2 (es) |
| BR (1) | BR0309026A (es) |
| CA (1) | CA2476056C (es) |
| CO (1) | CO5631442A2 (es) |
| DE (1) | DE60301570T2 (es) |
| DK (1) | DK1495023T3 (es) |
| EA (1) | EA007902B1 (es) |
| EC (1) | ECSP045338A (es) |
| ES (1) | ES2247540T3 (es) |
| FR (1) | FR2838123B1 (es) |
| HK (1) | HK1074631A1 (es) |
| HR (1) | HRP20040912B1 (es) |
| IL (2) | IL163755A0 (es) |
| IS (1) | IS2475B (es) |
| MA (1) | MA27297A1 (es) |
| ME (2) | MEP22508A (es) |
| MX (1) | MXPA04009639A (es) |
| NO (1) | NO329025B1 (es) |
| NZ (1) | NZ534786A (es) |
| PL (1) | PL215265B1 (es) |
| RS (1) | RS51399B (es) |
| SI (1) | SI1495023T1 (es) |
| TN (1) | TNSN04188A1 (es) |
| TW (1) | TWI335222B (es) |
| UA (1) | UA78016C2 (es) |
| WO (1) | WO2003084956A1 (es) |
| ZA (1) | ZA200406613B (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2859997B1 (fr) * | 2003-09-18 | 2006-02-03 | Sanofi Synthelabo | Nouveaux derives d'indolizine 1,2,3,6,7,8 substituee, inhibiteurs des fgfs, leur procede de preparation et les compositions pharmaceutiques les contenant. |
| CA2544786A1 (en) * | 2003-11-04 | 2005-05-12 | Dnavec Research Inc. | Method for producing gene transferred dendritic cells |
| FR2865934B1 (fr) * | 2004-02-05 | 2006-05-05 | Sanofi Synthelabo | Utilisation de derives d'indolizine 1,2,3 substitues, inhibiteurs des fgfs, pour la preparation de medicaments utiles pour le traitement de maladies liees a une angiogenese pathologique choroidienne |
| CN101006172B (zh) * | 2004-06-24 | 2012-09-05 | 株式会社载体研究所 | 包含导入了rna病毒的树突状细胞的抗癌剂 |
| US20090042820A1 (en) * | 2004-11-22 | 2009-02-12 | Threshold Pharmaceuticals, Inc. | Tubulin Binding Anti Cancer Agents And Prodrugs Thereof |
| FR2883286B1 (fr) * | 2005-03-16 | 2008-10-03 | Sanofi Aventis Sa | NOUVEAUX DERIVES D'IMIDAZO[1,5-a]PYRIDINES, INHIBITEURS DE FGFs, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT |
| FR2896247B1 (fr) * | 2006-01-13 | 2008-02-29 | Sanofi Aventis Sa | Composes dimeres agonistes des recepteurs des fgfs (fgfrs), leur procede de preparation et leur application en therapeutique |
| EP1891955A1 (en) * | 2006-07-24 | 2008-02-27 | Sanofi-Aventis | Use of 1,2,3-substituted indolizine derivatives, inhibitors of FGFs, for the preparation of a medicament intended for the treatment of degenerative joint diseases |
| WO2010027762A1 (en) * | 2008-09-04 | 2010-03-11 | Boehringer Ingelheim International Gmbh | Indolizine inhibitors of leukotriene production |
| WO2010108503A1 (en) | 2009-03-24 | 2010-09-30 | Life & Brain Gmbh | Promotion of neuronal integration in neural stem cell grafts |
| EP2270043A1 (en) * | 2009-07-03 | 2011-01-05 | Sanofi-Aventis | Extracellular allosteric inhibitor binding domain from a tyrosine kinase receptor |
| CN101648953B (zh) * | 2009-09-24 | 2012-09-05 | 绍兴文理学院 | 一种咪唑并[1，2-b]吡咯并[1，2-f]哒嗪衍生物及其制备方法和用途 |
| FR2962437B1 (fr) | 2010-07-06 | 2012-08-17 | Sanofi Aventis | Derives d'imidazopyridine, leur procede de preparation et leur application en therapeutique |
| FR2962438B1 (fr) * | 2010-07-06 | 2012-08-17 | Sanofi Aventis | Derives d'indolizines, procedes de preparation et application en therapeutique |
| FR2967412B1 (fr) * | 2010-11-17 | 2012-12-14 | Sanofi Aventis | Nouveaux derives d'indolizine, leur preparation et leur application en therapeutique |
| FR2985258A1 (fr) * | 2011-12-28 | 2013-07-05 | Sanofi Sa | Composes dimeres agonistes des recepteurs des fgfs (fgfrs), leur procede de preparation et leur application en therapeutique |
| US10065955B2 (en) * | 2014-12-10 | 2018-09-04 | Ono Pharmaceutical Co., Ltd. | Dihydroindolizinone derivative |
| EP3318563A1 (en) * | 2016-11-07 | 2018-05-09 | Sanofi | Substituted pyrido[3,4-b]indoles for the treatment of cartilage disorders |
| CN108864083B (zh) * | 2018-06-07 | 2021-05-25 | 广东药科大学 | 一类具有抗癌活性的氨基取代吲嗪类化合物及其衍生物 |
| CN110251513A (zh) * | 2019-07-03 | 2019-09-20 | 南京大学 | 一种含吡唑的中氮茚化合物在制备抗肿瘤药物中的应用 |
| US11976066B1 (en) | 2023-10-23 | 2024-05-07 | King Faisal University | Substituted 7-amino-3-(substituted benzoyl)indolizine-1-carboxylates as anti-tubercular agents |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ193926A (en) | 1979-07-06 | 1984-05-31 | Labaz Sanofi Nv | 2-(alkyl or phenyl)-3(4-hydroxybenzoyl)indolizines |
| US4378362A (en) | 1979-12-06 | 1983-03-29 | S.A. Labaz N.V. | Indolizine derivatives and process for preparing the same |
| FR2528845A1 (fr) * | 1982-06-17 | 1983-12-23 | Sanofi Sa | Nouveaux derives d'indolizine, leur procede de preparation ainsi que les compositions therapeutiques les contenant |
| FR2594438B1 (fr) * | 1986-02-14 | 1990-01-26 | Labaz Sanofi Nv | Derives d'indolizine, leur procede de preparation ainsi que les compositions en contenant |
| GB9318790D0 (en) * | 1993-09-10 | 1993-10-27 | Fujisawa Pharmaceutical Co | Heterocyclic derivatives |
| CA2373990C (en) * | 1999-05-21 | 2007-05-08 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| EP1399442B1 (en) | 2001-06-06 | 2006-08-09 | Vertex Pharmaceuticals Incorporated | Cak inhibitors and uses thereof |
| FR2859997B1 (fr) * | 2003-09-18 | 2006-02-03 | Sanofi Synthelabo | Nouveaux derives d'indolizine 1,2,3,6,7,8 substituee, inhibiteurs des fgfs, leur procede de preparation et les compositions pharmaceutiques les contenant. |
-
2002
- 2002-04-04 FR FR0204220A patent/FR2838123B1/fr not_active Expired - Fee Related
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2003
- 2003-02-04 UA UA20040807138A patent/UA78016C2/uk unknown
- 2003-03-27 TW TW092106944A patent/TWI335222B/zh not_active IP Right Cessation
- 2003-04-02 JP JP2003582153A patent/JP4741799B2/ja not_active Expired - Lifetime
- 2003-04-02 AU AU2003240984A patent/AU2003240984B2/en not_active Expired
- 2003-04-02 NZ NZ534786A patent/NZ534786A/en not_active IP Right Cessation
- 2003-04-02 WO PCT/FR2003/001030 patent/WO2003084956A1/fr active IP Right Grant
- 2003-04-02 EA EA200400994A patent/EA007902B1/ru not_active IP Right Cessation
- 2003-04-02 US US10/509,919 patent/US7442708B2/en not_active Expired - Lifetime
- 2003-04-02 BR BR0309026-4A patent/BR0309026A/pt not_active IP Right Cessation
- 2003-04-02 ME MEP-225/08A patent/MEP22508A/xx unknown
- 2003-04-02 AR AR20030101142A patent/AR040404A1/es active IP Right Grant
- 2003-04-02 SI SI200330093T patent/SI1495023T1/sl unknown
- 2003-04-02 DE DE60301570T patent/DE60301570T2/de not_active Expired - Lifetime
- 2003-04-02 CN CNB038077361A patent/CN100413863C/zh not_active Expired - Lifetime
- 2003-04-02 RS YUP-864/04A patent/RS51399B/en unknown
- 2003-04-02 KR KR1020047015666A patent/KR101022138B1/ko not_active IP Right Cessation
- 2003-04-02 PL PL372812A patent/PL215265B1/pl unknown
- 2003-04-02 IL IL16375503A patent/IL163755A0/xx unknown
- 2003-04-02 AT AT03730302T patent/ATE304013T1/de active
- 2003-04-02 ME MEP-2008-225A patent/ME00118B/me unknown
- 2003-04-02 MX MXPA04009639A patent/MXPA04009639A/es active IP Right Grant
- 2003-04-02 EP EP03730302A patent/EP1495023B1/fr not_active Expired - Lifetime
- 2003-04-02 DK DK03730302T patent/DK1495023T3/da active
- 2003-04-02 ZA ZA200406613A patent/ZA200406613B/en unknown
- 2003-04-02 ES ES03730302T patent/ES2247540T3/es not_active Expired - Lifetime
- 2003-04-02 CA CA2476056A patent/CA2476056C/fr not_active Expired - Lifetime
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2004
- 2004-08-19 IS IS7413A patent/IS2475B/is unknown
- 2004-08-26 IL IL163755A patent/IL163755A/en not_active IP Right Cessation
- 2004-09-27 MA MA27876A patent/MA27297A1/fr unknown
- 2004-09-30 TN TNP2004000188A patent/TNSN04188A1/fr unknown
- 2004-09-30 NO NO20044156A patent/NO329025B1/no not_active IP Right Cessation
- 2004-10-01 CO CO04098197A patent/CO5631442A2/es not_active Application Discontinuation
- 2004-10-04 EC EC2004005338A patent/ECSP045338A/es unknown
- 2004-10-04 HR HRP20040912AA patent/HRP20040912B1/hr not_active IP Right Cessation
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2005
- 2005-10-04 HK HK05108770A patent/HK1074631A1/xx not_active IP Right Cessation
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2008
- 2008-08-26 US US12/198,545 patent/US7803811B2/en not_active Expired - Lifetime
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