KR20040029075A - 소염제로서의 아미노피롤 화합물 - Google Patents
소염제로서의 아미노피롤 화합물 Download PDFInfo
- Publication number
- KR20040029075A KR20040029075A KR10-2004-7002895A KR20047002895A KR20040029075A KR 20040029075 A KR20040029075 A KR 20040029075A KR 20047002895 A KR20047002895 A KR 20047002895A KR 20040029075 A KR20040029075 A KR 20040029075A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- phenyl
- substituted phenyl
- compounds
- 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
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- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical class NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 title abstract description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 title 1
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 25
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- 229940002612 prodrug Drugs 0.000 claims abstract description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 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 abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- -1 3- (2,3-dihydroxypropoxy) phenyl Chemical group 0.000 claims description 47
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 21
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 18
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- 125000003545 alkoxy group Chemical group 0.000 claims description 13
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
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- 229940122696 MAP kinase inhibitor Drugs 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000002253 acid Substances 0.000 description 17
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 238000007363 ring formation reaction Methods 0.000 description 10
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- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 7
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 7
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- YCMSACSNYUSMOT-UHFFFAOYSA-N 2-(3-methoxybenzoyl)-4-oxo-4-pyridin-3-ylbutanenitrile Chemical compound COC1=CC=CC(C(=O)C(CC(=O)C=2C=NC=CC=2)C#N)=C1 YCMSACSNYUSMOT-UHFFFAOYSA-N 0.000 description 3
- KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 3
- VUMQGKYIBYYDIK-UHFFFAOYSA-N 2-benzoyl-4-oxo-4-pyridin-3-ylbutanenitrile Chemical compound C=1C=CN=CC=1C(=O)CC(C#N)C(=O)C1=CC=CC=C1 VUMQGKYIBYYDIK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- 238000012286 ELISA Assay Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- ULBAJOKWDAFCEB-UHFFFAOYSA-N [2-amino-1-(4-fluorophenyl)-5-pyridin-3-ylpyrrol-3-yl]-phenylmethanone Chemical compound C=1C=C(F)C=CC=1N1C(N)=C(C(=O)C=2C=CC=CC=2)C=C1C1=CC=CN=C1 ULBAJOKWDAFCEB-UHFFFAOYSA-N 0.000 description 3
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- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 208000018655 severe necrosis Diseases 0.000 description 1
- 230000011664 signaling Effects 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31616901P | 2001-08-30 | 2001-08-30 | |
| US60/316,169 | 2001-08-30 | ||
| PCT/EP2002/009505 WO2003020715A1 (en) | 2001-08-30 | 2002-08-26 | Aminopyrrole compounds as antiinflammatory agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040029075A true KR20040029075A (ko) | 2004-04-03 |
Family
ID=23227809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7002895A Abandoned KR20040029075A (ko) | 2001-08-30 | 2002-08-26 | 소염제로서의 아미노피롤 화합물 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6696471B2 (enExample) |
| EP (1) | EP1423378B1 (enExample) |
| JP (1) | JP2005506324A (enExample) |
| KR (1) | KR20040029075A (enExample) |
| CN (1) | CN1281603C (enExample) |
| AR (1) | AR037140A1 (enExample) |
| AT (1) | ATE309239T1 (enExample) |
| AU (1) | AU2002331179B2 (enExample) |
| BR (1) | BR0212077A (enExample) |
| CA (1) | CA2458808A1 (enExample) |
| DE (1) | DE60207273T2 (enExample) |
| ES (1) | ES2252509T3 (enExample) |
| MX (1) | MXPA04001810A (enExample) |
| PL (1) | PL373115A1 (enExample) |
| RU (1) | RU2315045C2 (enExample) |
| WO (1) | WO2003020715A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60331367D1 (de) | 2002-12-30 | 2010-04-01 | Angiotech Int Ag | Wirkstofffreisetzung von schnell gelierender polymerzusammensetzung |
| WO2006020365A2 (en) * | 2004-07-26 | 2006-02-23 | The Regents Of The University Of California | Method for prevention or treatment of inflamatory disease |
| US20100104536A1 (en) * | 2007-03-20 | 2010-04-29 | Indravadan Ambalal Modi | P38 inhibitors |
| WO2017075274A1 (en) | 2015-10-27 | 2017-05-04 | Children's Hospital Medical Center | Use of mapk inhibitors to reduce loss of hematopoietic stem cells during ex vivo culture and/or genetic manipulation |
| WO2017151409A1 (en) | 2016-02-29 | 2017-09-08 | University Of Florida Research Foundation, Incorporated | Chemotherapeutic methods |
| CA3127373A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068234A (en) * | 1990-02-26 | 1991-11-26 | Sterling Drug Inc. | 3-arylcarbonyl-1-(c-attached-n-heteryl)-1h-indoles |
| AU3044197A (en) | 1996-07-11 | 1998-02-09 | Pfizer Inc. | Pyridylpyrrole compounds useful as interleukin- and tnf antagonists |
| WO1998007425A1 (en) * | 1996-08-21 | 1998-02-26 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
| US5776954A (en) * | 1996-10-30 | 1998-07-07 | Merck & Co., Inc. | Substituted pyridyl pyrroles, compositions containing such compounds and methods of use |
| KR100404256B1 (ko) | 1998-05-05 | 2003-11-01 | 에프. 호프만-라 로슈 아게 | 피-38 엠에이피 키나제 저해제로서의 피라졸 유도체 |
| CA2331878A1 (en) * | 1998-05-14 | 1999-11-18 | G.D. Searle & Co. | 1,5-diaryl substituted pyrazoles as p38 kinase inhibitors |
-
2002
- 2002-08-26 CN CNB028166310A patent/CN1281603C/zh not_active Expired - Fee Related
- 2002-08-26 ES ES02767427T patent/ES2252509T3/es not_active Expired - Lifetime
- 2002-08-26 RU RU2004109817/04A patent/RU2315045C2/ru not_active IP Right Cessation
- 2002-08-26 BR BR0212077-1A patent/BR0212077A/pt not_active IP Right Cessation
- 2002-08-26 EP EP02767427A patent/EP1423378B1/en not_active Expired - Lifetime
- 2002-08-26 CA CA002458808A patent/CA2458808A1/en not_active Abandoned
- 2002-08-26 WO PCT/EP2002/009505 patent/WO2003020715A1/en not_active Ceased
- 2002-08-26 AU AU2002331179A patent/AU2002331179B2/en not_active Ceased
- 2002-08-26 MX MXPA04001810A patent/MXPA04001810A/es active IP Right Grant
- 2002-08-26 DE DE60207273T patent/DE60207273T2/de not_active Expired - Fee Related
- 2002-08-26 JP JP2003524985A patent/JP2005506324A/ja active Pending
- 2002-08-26 AT AT02767427T patent/ATE309239T1/de not_active IP Right Cessation
- 2002-08-26 PL PL02373115A patent/PL373115A1/xx not_active Application Discontinuation
- 2002-08-26 KR KR10-2004-7002895A patent/KR20040029075A/ko not_active Abandoned
- 2002-08-28 AR ARP020103226A patent/AR037140A1/es unknown
- 2002-08-29 US US10/231,792 patent/US6696471B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003020715A1 (en) | 2003-03-13 |
| JP2005506324A (ja) | 2005-03-03 |
| CN1547578A (zh) | 2004-11-17 |
| PL373115A1 (en) | 2005-08-08 |
| EP1423378B1 (en) | 2005-11-09 |
| DE60207273D1 (de) | 2005-12-15 |
| CA2458808A1 (en) | 2003-03-13 |
| EP1423378A1 (en) | 2004-06-02 |
| RU2004109817A (ru) | 2005-10-20 |
| AU2002331179B2 (en) | 2008-04-17 |
| MXPA04001810A (es) | 2004-07-08 |
| ATE309239T1 (de) | 2005-11-15 |
| AR037140A1 (es) | 2004-10-27 |
| CN1281603C (zh) | 2006-10-25 |
| US6696471B2 (en) | 2004-02-24 |
| RU2315045C2 (ru) | 2008-01-20 |
| DE60207273T2 (de) | 2006-07-20 |
| US20030130319A1 (en) | 2003-07-10 |
| BR0212077A (pt) | 2004-09-28 |
| ES2252509T3 (es) | 2006-05-16 |
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