ZA200402360B - Indole derivatives as COX II inhibitors. - Google Patents
Indole derivatives as COX II inhibitors. Download PDFInfo
- Publication number
- ZA200402360B ZA200402360B ZA200402360A ZA200402360A ZA200402360B ZA 200402360 B ZA200402360 B ZA 200402360B ZA 200402360 A ZA200402360 A ZA 200402360A ZA 200402360 A ZA200402360 A ZA 200402360A ZA 200402360 B ZA200402360 B ZA 200402360B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- compound according
- hydroxy
- hydrogen
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims description 11
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 4
- 150000002475 indoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 5
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 208000025978 Athletic injury Diseases 0.000 claims description 3
- 208000008035 Back Pain Diseases 0.000 claims description 3
- 206010006811 Bursitis Diseases 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 206010019233 Headaches Diseases 0.000 claims description 3
- 201000002481 Myositis Diseases 0.000 claims description 3
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
- 206010036600 Premature labour Diseases 0.000 claims description 3
- 208000010040 Sprains and Strains Diseases 0.000 claims description 3
- 208000000491 Tendinopathy Diseases 0.000 claims description 3
- 206010043255 Tendonitis Diseases 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 208000026440 premature labor Diseases 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
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- 201000004415 tendinitis Diseases 0.000 claims description 3
- GVUYJYPBPIQKHW-UHFFFAOYSA-N (6-methylsulfonyl-3-phenylsulfanyl-1h-indol-2-yl)methanol Chemical compound OCC=1NC2=CC(S(=O)(=O)C)=CC=C2C=1SC1=CC=CC=C1 GVUYJYPBPIQKHW-UHFFFAOYSA-N 0.000 claims description 2
- XAOIOAYWZAVEIW-UHFFFAOYSA-N 3-(2,4-difluorophenyl)sulfanyl-6-methylsulfonyl-1h-indole-2-carbonitrile Chemical compound N#CC=1NC2=CC(S(=O)(=O)C)=CC=C2C=1SC1=CC=C(F)C=C1F XAOIOAYWZAVEIW-UHFFFAOYSA-N 0.000 claims description 2
- VHSYYXRBWBHMNB-UHFFFAOYSA-N 3-(4-fluorophenoxy)-2-methyl-6-methylsulfonyl-1h-indole Chemical compound CC=1NC2=CC(S(C)(=O)=O)=CC=C2C=1OC1=CC=C(F)C=C1 VHSYYXRBWBHMNB-UHFFFAOYSA-N 0.000 claims description 2
- OHVHHRUUBCGBLX-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfanyl-6-methylsulfonyl-1h-indole-2-carbonitrile Chemical compound N#CC=1NC2=CC(S(=O)(=O)C)=CC=C2C=1SC1=CC=C(F)C=C1 OHVHHRUUBCGBLX-UHFFFAOYSA-N 0.000 claims description 2
- VNYCGFXZOQHLEM-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfinyl-2-methyl-6-methylsulfonyl-1h-indole Chemical compound CC=1NC2=CC(S(C)(=O)=O)=CC=C2C=1S(=O)C1=CC=C(F)C=C1 VNYCGFXZOQHLEM-UHFFFAOYSA-N 0.000 claims description 2
- JGGHRZWTRXUNBK-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-2-methyl-6-methylsulfonyl-1h-indole Chemical compound CC=1NC2=CC(S(C)(=O)=O)=CC=C2C=1CC1=CC=CC=C1Cl JGGHRZWTRXUNBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 21
- 125000000753 cycloalkyl group Chemical group 0.000 description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 17
- 125000003884 phenylalkyl group Chemical group 0.000 description 14
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- 150000003180 prostaglandins Chemical class 0.000 description 10
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- 150000003254 radicals Chemical class 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000004404 heteroalkyl group Chemical group 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
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- 125000004429 atom Chemical group 0.000 description 5
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- 238000006243 chemical reaction Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- PEZNEXFPRSOYPL-UHFFFAOYSA-N (bis(trifluoroacetoxy)iodo)benzene Chemical compound FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)C1=CC=CC=C1 PEZNEXFPRSOYPL-UHFFFAOYSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- 238000001727 in vivo Methods 0.000 description 4
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- 150000003457 sulfones Chemical class 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
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- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
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- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid 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
- 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
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P15/06—Antiabortive agents; Labour repressants
-
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32538901P | 2001-09-27 | 2001-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200402360B true ZA200402360B (en) | 2005-04-26 |
Family
ID=23267681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200402360A ZA200402360B (en) | 2001-09-27 | 2004-03-25 | Indole derivatives as COX II inhibitors. |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US6872744B2 (es) |
| EP (1) | EP1438289B1 (es) |
| JP (1) | JP4141954B2 (es) |
| KR (1) | KR20040047862A (es) |
| CN (1) | CN1261412C (es) |
| AR (1) | AR036624A1 (es) |
| AT (1) | ATE292115T1 (es) |
| BR (1) | BR0212925A (es) |
| CA (1) | CA2461670A1 (es) |
| CO (1) | CO5560557A2 (es) |
| DE (1) | DE60203529T2 (es) |
| DK (1) | DK1438289T3 (es) |
| ES (1) | ES2238616T3 (es) |
| HR (1) | HRPK20040271B3 (es) |
| HU (1) | HUP0401499A3 (es) |
| IL (1) | IL160752A0 (es) |
| MX (1) | MXPA04002824A (es) |
| NO (1) | NO20041237L (es) |
| NZ (1) | NZ531577A (es) |
| PL (1) | PL370342A1 (es) |
| PT (1) | PT1438289E (es) |
| RU (1) | RU2004113111A (es) |
| SI (1) | SI1438289T1 (es) |
| WO (1) | WO2003029212A1 (es) |
| ZA (1) | ZA200402360B (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040047862A (ko) * | 2001-09-27 | 2004-06-05 | 에프. 호프만-라 로슈 아게 | Ｃｏｘ ⅱ 억제제로서의 인돌 유도체 |
| SE0202241D0 (sv) * | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| AU2003258145A1 (en) * | 2002-08-07 | 2004-02-25 | Idenix (Cayman) Limited | Substituted phenylindoles for the treatment of hiv |
| MXPA06007054A (es) * | 2003-12-19 | 2007-04-17 | Elixir Pharmaceuticals Inc | Metodos para tratar una enfermedad. |
| EP1589016A1 (en) * | 2004-04-13 | 2005-10-26 | Cephalon France | Thio-substituted tricyclic and bicyclic aromatic methanesulfinyl derivatives |
| US7119214B2 (en) | 2004-04-13 | 2006-10-10 | Cephalon France | Thio-substituted tricyclic and bicyclic aromatic methanesulfinyl derivatives |
| US7423176B2 (en) | 2004-04-13 | 2008-09-09 | Cephalon, Inc. | Bicyclic aromatic sulfinyl derivatives |
| DE602005009209D1 (de) | 2004-06-18 | 2008-10-02 | Biolipox Ab | Zur behandlung von entzündungen geeignete indole |
| WO2006041961A1 (en) * | 2004-10-05 | 2006-04-20 | GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTHAND HUMAN SERVICES | Arylthioindole tubulin polymerization inhibitors and methods of treating or preventing cancer using same |
| ATE501119T1 (de) | 2005-01-19 | 2011-03-15 | Biolipox Ab | Entzündungshemmende indol-derivate |
| US7622495B2 (en) * | 2006-10-03 | 2009-11-24 | Neurim Pharmaceuticals (1991) Ltd. | Substituted aryl-indole compounds and their kynurenine/kynuramine-like metabolites as therapeutic agents |
| MX2009004898A (es) | 2006-11-09 | 2009-05-19 | Hoffmann La Roche | Derivados de indol y de benzofurano-2-carboxamida. |
| CN103201262B (zh) * | 2010-08-20 | 2016-06-01 | 艾米拉医药股份有限公司 | 自分泌运动因子抑制剂及其用途 |
| EP2714680B1 (en) | 2011-05-27 | 2015-11-25 | Amira Pharmaceuticals, Inc. | Heterocyclic autotaxin inhibitors and uses thereof |
| US9714240B2 (en) | 2013-09-17 | 2017-07-25 | Pharmakea, Inc. | Vinyl autotaxin inhibitor compounds |
| US9951026B2 (en) | 2013-09-17 | 2018-04-24 | Pharmakea, Inc. | Heterocyclic vinyl autotaxin inhibitor compounds |
| WO2015048301A1 (en) | 2013-09-26 | 2015-04-02 | Pharmakea, Inc. | Autotaxin inhibitor compounds |
| CR20160289A (es) | 2013-11-22 | 2016-09-27 | Pharmakea Inc | Compuestos de inhibidor de autotaxina |
| AU2016268250B2 (en) | 2015-05-27 | 2020-08-27 | Sabre Therapeutics Llc | Autotaxin inhibitors and uses thereof |
| KR102241064B1 (ko) | 2019-07-30 | 2021-04-16 | 부산대학교 산학협력단 | 신규한 인돌 유도체 및 이를 포함하는 염증성 질환 예방 또는 치료용 조성물 |
| CN113004187B (zh) * | 2021-03-16 | 2022-09-20 | 沈阳药科大学 | 一种具有抑制有机阴离子转运体1活性的化合物及制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4654360A (en) | 1984-06-01 | 1987-03-31 | Syntex (U.S.A.) Inc. | 1,2,3-trisubstituted indoles for treatment of inflammation |
| PT93943A (pt) | 1989-05-05 | 1991-02-08 | Searle & Co | Processo para a preparacao de composicoes contendo compostos indole-2-carboxilato para tratamento de perturbacoes do snc |
| DE4338770A1 (de) | 1993-11-12 | 1995-05-18 | Matthias Dr Lehr | Indol-2-alkansäuren und ihre Derivate als Hemmstoffe der Phospholipase A¶2¶ |
| WO1998008818A1 (en) | 1996-08-26 | 1998-03-05 | Genetics Institute, Inc. | Inhibitors of phospholipase enzymes |
| WO1998051667A1 (fr) * | 1997-05-16 | 1998-11-19 | Chugai Seiyaku Kabushiki Kaisha | Derives d'indole et derives de mono- et diazaindole |
| IL137540A0 (en) | 1998-02-25 | 2001-07-24 | Genetics Inst | Inhibitors of phospholipase a2 |
| MXPA00006605A (es) * | 1999-07-02 | 2004-12-09 | Pfizer | Compuestos de carbonil-indol biciclicos como agentes antiinflamatorios/analgesicos. |
| US6306890B1 (en) * | 1999-08-30 | 2001-10-23 | Vanderbilt University | Esters derived from indolealkanols and novel amides derived from indolealkylamides that are selective COX-2 inhibitors |
| US6376708B1 (en) * | 2000-04-11 | 2002-04-23 | Monsanto Technology Llc | Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts |
| KR20040047862A (ko) * | 2001-09-27 | 2004-06-05 | 에프. 호프만-라 로슈 아게 | Ｃｏｘ ⅱ 억제제로서의 인돌 유도체 |
| TW200400177A (en) * | 2002-06-04 | 2004-01-01 | Wyeth Corp | 1-(Aminoalkyl)-3-sulfonylindole and-indazole derivatives as 5-hydroxytryptamine-6 ligands |
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2002
- 2002-09-20 KR KR10-2004-7004428A patent/KR20040047862A/ko not_active Application Discontinuation
- 2002-09-20 PT PT02779382T patent/PT1438289E/pt unknown
- 2002-09-20 AT AT02779382T patent/ATE292115T1/de not_active IP Right Cessation
- 2002-09-20 MX MXPA04002824A patent/MXPA04002824A/es unknown
- 2002-09-20 CA CA002461670A patent/CA2461670A1/en not_active Abandoned
- 2002-09-20 JP JP2003532462A patent/JP4141954B2/ja not_active Expired - Fee Related
- 2002-09-20 SI SI200230116T patent/SI1438289T1/xx unknown
- 2002-09-20 BR BR0212925-6A patent/BR0212925A/pt not_active IP Right Cessation
- 2002-09-20 RU RU2004113111/04A patent/RU2004113111A/ru not_active Application Discontinuation
- 2002-09-20 HU HU0401499A patent/HUP0401499A3/hu unknown
- 2002-09-20 EP EP02779382A patent/EP1438289B1/en not_active Expired - Lifetime
- 2002-09-20 IL IL16075202A patent/IL160752A0/xx unknown
- 2002-09-20 WO PCT/EP2002/010557 patent/WO2003029212A1/en active IP Right Grant
- 2002-09-20 DK DK02779382T patent/DK1438289T3/da active
- 2002-09-20 CN CNB028191900A patent/CN1261412C/zh not_active Expired - Fee Related
- 2002-09-20 PL PL02370342A patent/PL370342A1/xx not_active Application Discontinuation
- 2002-09-20 DE DE60203529T patent/DE60203529T2/de not_active Expired - Fee Related
- 2002-09-20 NZ NZ531577A patent/NZ531577A/en unknown
- 2002-09-20 ES ES02779382T patent/ES2238616T3/es not_active Expired - Lifetime
- 2002-09-25 AR ARP020103595A patent/AR036624A1/es not_active Application Discontinuation
- 2002-09-26 US US10/255,891 patent/US6872744B2/en not_active Expired - Fee Related
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2004
- 2004-03-19 HR HR20040271A patent/HRPK20040271B3/xx not_active IP Right Cessation
- 2004-03-24 CO CO04027740A patent/CO5560557A2/es not_active Application Discontinuation
- 2004-03-24 NO NO20041237A patent/NO20041237L/no unknown
- 2004-03-25 ZA ZA200402360A patent/ZA200402360B/en unknown
-
2005
- 2005-02-25 US US11/065,841 patent/US7074939B2/en not_active Expired - Fee Related
-
2006
- 2006-03-02 US US11/391,655 patent/US7410994B2/en not_active Expired - Fee Related
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