CA2269035A1 - Indenes inhibiteurs du cox-2 - Google Patents
Indenes inhibiteurs du cox-2 Download PDFInfo
- Publication number
- CA2269035A1 CA2269035A1 CA002269035A CA2269035A CA2269035A1 CA 2269035 A1 CA2269035 A1 CA 2269035A1 CA 002269035 A CA002269035 A CA 002269035A CA 2269035 A CA2269035 A CA 2269035A CA 2269035 A1 CA2269035 A1 CA 2269035A1
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- hydrogen
- alkyl
- halogen
- fluoroalkoxy
- 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.)
- Abandoned
Links
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 3
- 101150071146 COX2 gene Proteins 0.000 title 1
- 101100114534 Caenorhabditis elegans ctc-2 gene Proteins 0.000 title 1
- 101150000187 PTGS2 gene Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical group 0.000 claims abstract description 21
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
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- 238000010998 test method Methods 0.000 description 3
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- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- PTUSXMWNCXRKAX-UHFFFAOYSA-N 2-(1h-inden-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)C=CC2=C1 PTUSXMWNCXRKAX-UHFFFAOYSA-N 0.000 description 2
- BMUDPLZKKRQECS-UHFFFAOYSA-K 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid iron(3+) hydroxide Chemical compound [OH-].[Fe+3].[N-]1C2=C(C)C(CCC(O)=O)=C1C=C([N-]1)C(CCC(O)=O)=C(C)C1=CC(C(C)=C1C=C)=NC1=CC(C(C)=C1C=C)=NC1=C2 BMUDPLZKKRQECS-UHFFFAOYSA-K 0.000 description 2
- -1 CFg Chemical group 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
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- 101000605122 Homo sapiens Prostaglandin G/H synthase 1 Proteins 0.000 description 2
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- 238000012153 long-term therapy Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012740 non-selective inhibitor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003358 phospholipase A2 inhibitor Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003757 reverse transcription PCR Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- DDMGAAYEUNWXSI-UHFFFAOYSA-M sodium;icosa-5,8,11,14-tetraenoate Chemical compound [Na+].CCCCCC=CCC=CCC=CCC=CCCCC([O-])=O DDMGAAYEUNWXSI-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- KJLXVAPBVMFHOL-UHFFFAOYSA-N thiolane-2,4-dione Chemical compound O=C1CSC(=O)C1 KJLXVAPBVMFHOL-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
La présente invention concerne des composés représentés par la structure (1) de la formule générale (I). Dans cette formule, R<1> est hydrogène, halogène, alkyl, alcoxy, fluoroalcoxy, trifluorométhyl, alkylthio ou SCF3; R<2> et R<3> sont chacun indépendamment hydrogène ou alkyl, ou bien R<2> et R<3> peuvent, ensemble, former un cycle cycloalkyl saturé. Enfin, R<4>, R<5>, R<6>, R<7> et R<8> sont chacun indépendamment hydrogène, alkyl, alcoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halogène, fluoroalcoxy, CF3 ou SCF3. Ces composés conviennent particulièrement au traitement de troubles arthritiques, du cancer colorectal et de la maladie d'Alzheimer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74794896A | 1996-11-12 | 1996-11-12 | |
| US08/747,948 | 1996-11-12 | ||
| PCT/US1997/020231 WO1998021195A1 (fr) | 1996-11-12 | 1997-11-10 | Indenes inhibiteurs du cox-2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2269035A1 true CA2269035A1 (fr) | 1998-05-22 |
Family
ID=25007366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002269035A Abandoned CA2269035A1 (fr) | 1996-11-12 | 1997-11-10 | Indenes inhibiteurs du cox-2 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0948493A1 (fr) |
| JP (1) | JP2001504118A (fr) |
| KR (1) | KR20000053227A (fr) |
| CN (1) | CN1237162A (fr) |
| AU (1) | AU5105598A (fr) |
| BR (1) | BR9713346A (fr) |
| CA (1) | CA2269035A1 (fr) |
| HU (1) | HUP9904696A2 (fr) |
| WO (1) | WO1998021195A1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001045703A1 (fr) | 1999-12-23 | 2001-06-28 | Nitromed, Inc. | Inhibiteurs de cyclooxygenase-2 nitroses et nitrosyles, compositions et procedes d'utilisation |
| ES2275218T3 (es) | 2003-05-07 | 2007-06-01 | Osteologix A/S | Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos. |
| CN101365461B (zh) | 2006-01-04 | 2013-07-24 | 南方研究所 | 舒林酸衍生物、其用途和其制备 |
| CN104592091B (zh) * | 2015-01-27 | 2017-07-04 | 冉瑞琼 | 一种含吲哚乙酸核心结构的化合物及其应用 |
| US20240165148A1 (en) | 2021-03-15 | 2024-05-23 | Saul Yedgar | Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory diseases |
| CN116635368A (zh) * | 2021-10-15 | 2023-08-22 | 北京安健熹医药科技有限公司 | 2,3-二甲氧基-5-甲基-1,4-苯醌烷基醇衍生物及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647858A (en) * | 1970-05-01 | 1972-03-07 | Merck & Co Inc | Process for preparing 1-benzylidene-3-indenyl acetic acids |
| MX9302419A (es) * | 1992-04-28 | 1994-03-31 | American Home Prod | Derivados de acido tetronico, tiotetronico y tetramico. |
| GB9403857D0 (en) * | 1994-03-01 | 1994-04-20 | Scotia Holdings Plc | Fatty acid derivatives |
-
1997
- 1997-11-10 CA CA002269035A patent/CA2269035A1/fr not_active Abandoned
- 1997-11-10 JP JP52266398A patent/JP2001504118A/ja active Pending
- 1997-11-10 CN CN97199655A patent/CN1237162A/zh active Pending
- 1997-11-10 AU AU51055/98A patent/AU5105598A/en not_active Abandoned
- 1997-11-10 WO PCT/US1997/020231 patent/WO1998021195A1/fr not_active Application Discontinuation
- 1997-11-10 KR KR1019990704202A patent/KR20000053227A/ko not_active Application Discontinuation
- 1997-11-10 BR BR9713346-9A patent/BR9713346A/pt not_active Application Discontinuation
- 1997-11-10 HU HU9904696A patent/HUP9904696A2/hu unknown
- 1997-11-10 EP EP97945622A patent/EP0948493A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998021195A1 (fr) | 1998-05-22 |
| HUP9904696A2 (hu) | 2000-05-28 |
| KR20000053227A (ko) | 2000-08-25 |
| BR9713346A (pt) | 2000-05-09 |
| JP2001504118A (ja) | 2001-03-27 |
| EP0948493A1 (fr) | 1999-10-13 |
| AU5105598A (en) | 1998-06-03 |
| CN1237162A (zh) | 1999-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |