CN1386737A - Antifibrosis pyridinone medicine and its prepaing process - Google Patents
Antifibrosis pyridinone medicine and its prepaing process Download PDFInfo
- Publication number
- CN1386737A CN1386737A CN 02114190 CN02114190A CN1386737A CN 1386737 A CN1386737 A CN 1386737A CN 02114190 CN02114190 CN 02114190 CN 02114190 A CN02114190 A CN 02114190A CN 1386737 A CN1386737 A CN 1386737A
- Authority
- CN
- China
- Prior art keywords
- formula
- pyridone
- methyl
- medicine
- fibrosis
- 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.)
- Granted
Links
- 239000003814 drug Substances 0.000 title claims abstract description 25
- 230000002300 anti-fibrosis Effects 0.000 title claims abstract description 18
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title abstract description 10
- 230000008569 process Effects 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 9
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 9
- 229960000583 acetic acid Drugs 0.000 claims abstract description 7
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 7
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000003672 processing method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 claims description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 150000005299 pyridinones Chemical class 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 abstract 2
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical class C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004317 sodium nitrate Substances 0.000 abstract 1
- 235000010344 sodium nitrate Nutrition 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 201000010099 disease Diseases 0.000 description 6
- 230000003176 fibrotic effect Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- -1 1-monosubstituted phenyl-5-methyl-2 (IH) pyridone Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 201000002793 renal fibrosis Diseases 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- QLFMOQVBGPZBAY-UHFFFAOYSA-N 1-(2-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1Br QLFMOQVBGPZBAY-UHFFFAOYSA-N 0.000 description 1
- MCAAQJLJBILPBZ-UHFFFAOYSA-N 1-(3-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Br)=C1 MCAAQJLJBILPBZ-UHFFFAOYSA-N 0.000 description 1
- PYZJZGLJFOVHRH-UHFFFAOYSA-N 1-(4-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Br)C=C1 PYZJZGLJFOVHRH-UHFFFAOYSA-N 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010028594 Myocardial fibrosis Diseases 0.000 description 1
- JXRWUCWQCGMRQQ-UHFFFAOYSA-N NCC1=C(C=CC=C1)N1C(C=CC(=C1)C)=O Chemical compound NCC1=C(C=CC=C1)N1C(C=CC(=C1)C)=O JXRWUCWQCGMRQQ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02114190 CN1218942C (en) | 2002-06-11 | 2002-06-11 | Antifibrosis pyridinone medicine and its prepaing process |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02114190 CN1218942C (en) | 2002-06-11 | 2002-06-11 | Antifibrosis pyridinone medicine and its prepaing process |
Publications (2)
Publication Number | Publication Date |
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CN1386737A true CN1386737A (en) | 2002-12-25 |
CN1218942C CN1218942C (en) | 2005-09-14 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 02114190 Expired - Lifetime CN1218942C (en) | 2002-06-11 | 2002-06-11 | Antifibrosis pyridinone medicine and its prepaing process |
Country Status (1)
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CN (1) | CN1218942C (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005047256A1 (en) * | 2003-11-14 | 2005-05-26 | Shanghai Genomics, Inc. | The derivatives of pyridone and the use of them |
WO2006108354A1 (en) * | 2005-04-13 | 2006-10-19 | Xiangya Hospital Of Central South University | 1-(substituted phenyl)-5- methyl- 2 - (1h) pyridone in the manufacture of medicaments for treating fibrosis in organs or tissues |
CN100396669C (en) * | 2006-03-15 | 2008-06-25 | 浙江省医学科学院 | Production of pyriphenanthrenone as anti-fibrosis medicine |
WO2008131586A1 (en) * | 2007-04-27 | 2008-11-06 | Dieretech Investment Limited | Uses of 5-methyl-1-(substituted phenyl)-2(1h)-pyridones as anti-inflammatory and tnf-alpha-blocking agents |
WO2008147170A1 (en) * | 2007-05-29 | 2008-12-04 | Cell Therapy Technology, S.A. De C.V. | New process of synthesis for obtaining 5-methyl-1-phenyl-2 (ih) -pyridone, composition and use of the same |
WO2009111947A1 (en) * | 2008-03-10 | 2009-09-17 | 广东东阳关药业有限公司 | Crystalline 1-(3-fluorophenyl)-5-methyl-2-(1h)pyridone, the preparation methods, compositions and applications thereof |
WO2010045871A1 (en) * | 2008-10-21 | 2010-04-29 | Dieretech Investment Limited | Composition and method for treating proteinuria |
CN101723883A (en) * | 2008-10-24 | 2010-06-09 | 上海睿星基因技术有限公司 | Method for preparing oxycodone |
WO2010065755A1 (en) | 2008-12-04 | 2010-06-10 | Concert Pharmaceuticals, Inc. | Deuterated pyridinones |
CN102149683A (en) * | 2009-05-25 | 2011-08-10 | 中南大学 | 1-(substituted benzyl)-5-trifluoromethyl-2-(1H) pyridone compounds and their salts, their preparation methods and use thereof |
CN102149682A (en) * | 2009-05-25 | 2011-08-10 | 中南大学 | Preparation methods and uses of 1-(substituted aryl)-5-trifluoromethyl-2-(1H)-pyridone compounds and their salts |
US8304413B2 (en) | 2008-06-03 | 2012-11-06 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
US8519140B2 (en) | 2009-06-03 | 2013-08-27 | Intermune, Inc. | Method for synthesizing pirfenidone |
CN103570630A (en) * | 2012-07-18 | 2014-02-12 | 广东东阳光药业有限公司 | Heterocyclic nitrogen derivative and application thereof in medicines |
US8741936B2 (en) | 2005-05-10 | 2014-06-03 | Intermune, Inc. | Method of modulating stress-activated protein kinase system |
WO2015153683A1 (en) | 2014-04-02 | 2015-10-08 | Intermune, Inc. | Anti-fibrotic pyridinones |
CN105085383A (en) * | 2015-08-19 | 2015-11-25 | 四川大学 | 5-methyl-2(1H)pyridone derivatives, and preparation method and application thereof |
CN105130884A (en) * | 2015-07-30 | 2015-12-09 | 四川大学 | 5-methyl-2(1H)pyridone derivatives, preparation method and applications thereof |
CN105175326A (en) * | 2015-08-19 | 2015-12-23 | 四川国康药业有限公司 | 5-methyl-2(1H)pyridone derivatives, preparation method and application |
CN105330598A (en) * | 2015-12-02 | 2016-02-17 | 新发药业有限公司 | Preparing method for pirfenidone |
US9359379B2 (en) | 2012-10-02 | 2016-06-07 | Intermune, Inc. | Anti-fibrotic pyridinones |
WO2017072216A1 (en) | 2015-10-29 | 2017-05-04 | Procos S.P.A. | Process for the synthesis of pirfenidone |
US9902712B2 (en) | 2013-12-19 | 2018-02-27 | Sunshine Lake Pharma Co., Ltd. | Nitrogenous heterocyclic derivatives and their application in drugs |
-
2002
- 2002-06-11 CN CN 02114190 patent/CN1218942C/en not_active Expired - Lifetime
Cited By (55)
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CN100358872C (en) * | 2003-11-14 | 2008-01-02 | 上海睿星基因技术有限公司 | The derivatives of pyridone and use thereof |
US7825133B2 (en) | 2003-11-14 | 2010-11-02 | Shanghai Genomics, Inc. | Derivatives of pyridone and the use of them |
US8022087B2 (en) | 2003-11-14 | 2011-09-20 | Shangai Genomics, Inc. | Derivatives of pyridone and use thereof |
US8084465B2 (en) | 2003-11-14 | 2011-12-27 | Shanghai Genomics, Inc. | Derivatives of pryidone and use thereof |
WO2005047256A1 (en) * | 2003-11-14 | 2005-05-26 | Shanghai Genomics, Inc. | The derivatives of pyridone and the use of them |
CN1953749B (en) * | 2005-04-13 | 2010-04-14 | 深圳市东阳光实业发展有限公司 | Application of 1-(substituted phenyl)-5-methyl-2-(1H)-pyridone (I) compound in preparing medicine for anti-organifibrosis or tissue fibrosis |
WO2006108354A1 (en) * | 2005-04-13 | 2006-10-19 | Xiangya Hospital Of Central South University | 1-(substituted phenyl)-5- methyl- 2 - (1h) pyridone in the manufacture of medicaments for treating fibrosis in organs or tissues |
US8741936B2 (en) | 2005-05-10 | 2014-06-03 | Intermune, Inc. | Method of modulating stress-activated protein kinase system |
US9527816B2 (en) | 2005-05-10 | 2016-12-27 | Intermune, Inc. | Method of modulating stress-activated protein kinase system |
US10010536B2 (en) | 2005-05-10 | 2018-07-03 | Intermune, Inc. | Method of modulating stress-activated protein kinase system |
CN100396669C (en) * | 2006-03-15 | 2008-06-25 | 浙江省医学科学院 | Production of pyriphenanthrenone as anti-fibrosis medicine |
WO2008131586A1 (en) * | 2007-04-27 | 2008-11-06 | Dieretech Investment Limited | Uses of 5-methyl-1-(substituted phenyl)-2(1h)-pyridones as anti-inflammatory and tnf-alpha-blocking agents |
WO2008147170A1 (en) * | 2007-05-29 | 2008-12-04 | Cell Therapy Technology, S.A. De C.V. | New process of synthesis for obtaining 5-methyl-1-phenyl-2 (ih) -pyridone, composition and use of the same |
WO2009111947A1 (en) * | 2008-03-10 | 2009-09-17 | 广东东阳关药业有限公司 | Crystalline 1-(3-fluorophenyl)-5-methyl-2-(1h)pyridone, the preparation methods, compositions and applications thereof |
US8232408B2 (en) | 2008-03-10 | 2012-07-31 | Sunshine Lake Pharma Co., Ltd. | Crystalline 1-(3-fluorophenyl)-5-methyl-2-(1H)pyridone, the preparation methods, compositions and applications thereof |
CN101986781B (en) * | 2008-03-10 | 2013-08-28 | 广东东阳光药业有限公司 | Crystalline I-(3-fluorophenyl)-5-methyl-2-(1H)pyridone, the preparation methods, compositions and applications thereof |
US8304413B2 (en) | 2008-06-03 | 2012-11-06 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
US9290450B2 (en) | 2008-06-03 | 2016-03-22 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
USRE47142E1 (en) | 2008-06-03 | 2018-11-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
US8969347B2 (en) | 2008-06-03 | 2015-03-03 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
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Also Published As
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