RU2007141892A - 5-метил-1-(замещенный фенил)-2-(1н)-пиридон для производства медикаментов для лечения фиброза в органах и тканях - Google Patents
5-метил-1-(замещенный фенил)-2-(1н)-пиридон для производства медикаментов для лечения фиброза в органах и тканях Download PDFInfo
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- RU2007141892A RU2007141892A RU2007141892/15A RU2007141892A RU2007141892A RU 2007141892 A RU2007141892 A RU 2007141892A RU 2007141892/15 A RU2007141892/15 A RU 2007141892/15A RU 2007141892 A RU2007141892 A RU 2007141892A RU 2007141892 A RU2007141892 A RU 2007141892A
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- Prior art keywords
- methyl
- pyridone
- compounds
- use according
- fibrosis
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- 206010016654 Fibrosis Diseases 0.000 title claims abstract 11
- 230000004761 fibrosis Effects 0.000 title claims abstract 11
- -1 5-METHYL-1- (SUBSTITUTED PHENYL) -2- (1H) -PYRIDONE Chemical class 0.000 title claims abstract 8
- 239000003814 drug Substances 0.000 title claims abstract 6
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 210000000056 organ Anatomy 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract 14
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 229940079593 drug Drugs 0.000 claims abstract 5
- 125000001424 substituent group Chemical group 0.000 claims abstract 5
- IFCIIDXNZSQOPD-UHFFFAOYSA-N 1-(2,3-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Br)=C1Br IFCIIDXNZSQOPD-UHFFFAOYSA-N 0.000 claims abstract 2
- XYPVXRNOJDTEDJ-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Cl)=C1Cl XYPVXRNOJDTEDJ-UHFFFAOYSA-N 0.000 claims abstract 2
- BLHHEWJJZFVRNB-UHFFFAOYSA-N 1-(2,4-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Br)C=C1Br BLHHEWJJZFVRNB-UHFFFAOYSA-N 0.000 claims abstract 2
- IXSFWFDBKAFHHA-UHFFFAOYSA-N 1-(2,5-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Br)=CC=C1Br IXSFWFDBKAFHHA-UHFFFAOYSA-N 0.000 claims abstract 2
- ZEICHSKCYQRIIG-UHFFFAOYSA-N 1-(2,6-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(Br)C=CC=C1Br ZEICHSKCYQRIIG-UHFFFAOYSA-N 0.000 claims abstract 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 claims abstract 2
- LNCCSHHBXXNHHJ-UHFFFAOYSA-N 1-(2-fluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1F LNCCSHHBXXNHHJ-UHFFFAOYSA-N 0.000 claims abstract 2
- DCDSWTUVNHBRJZ-UHFFFAOYSA-N 1-(2-iodophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1I DCDSWTUVNHBRJZ-UHFFFAOYSA-N 0.000 claims abstract 2
- PPEKVFBDIFWVEV-UHFFFAOYSA-N 1-(3,4-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Br)C(Br)=C1 PPEKVFBDIFWVEV-UHFFFAOYSA-N 0.000 claims abstract 2
- NUFQXKSYNQFJSW-UHFFFAOYSA-N 1-(3,5-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Br)=CC(Br)=C1 NUFQXKSYNQFJSW-UHFFFAOYSA-N 0.000 claims abstract 2
- 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 claims abstract 2
- JDZYVVUJIQYGRX-UHFFFAOYSA-N 1-(3-fluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(F)=C1 JDZYVVUJIQYGRX-UHFFFAOYSA-N 0.000 claims abstract 2
- QOXOVUCNQVZUEH-UHFFFAOYSA-N 1-(3-iodophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(I)=C1 QOXOVUCNQVZUEH-UHFFFAOYSA-N 0.000 claims abstract 2
- 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 claims abstract 2
- NNOLFDHGQTWVGS-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(F)C=C1 NNOLFDHGQTWVGS-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 210000001519 tissue Anatomy 0.000 claims 5
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 210000003734 kidney Anatomy 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 3
- 238000002347 injection Methods 0.000 claims 3
- 239000007924 injection Substances 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 206010060932 Postoperative adhesion Diseases 0.000 claims 2
- 206010036940 Prostatic adenoma Diseases 0.000 claims 2
- 241000242678 Schistosoma Species 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 208000034189 Sclerosis Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 230000003176 fibrotic effect Effects 0.000 claims 2
- 206010061989 glomerulosclerosis Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000003902 lesion Effects 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 210000004165 myocardium Anatomy 0.000 claims 2
- 210000003491 skin Anatomy 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- MIUCEBJFPNOZFC-UHFFFAOYSA-N 1-(2,3-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(F)=C1F MIUCEBJFPNOZFC-UHFFFAOYSA-N 0.000 claims 1
- DIVMPFRJHNDQHW-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Cl)C=C1Cl DIVMPFRJHNDQHW-UHFFFAOYSA-N 0.000 claims 1
- ICETYRMEWRWSJX-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(F)C=C1F ICETYRMEWRWSJX-UHFFFAOYSA-N 0.000 claims 1
- LUYVIZYIGZWLEK-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Cl)=CC=C1Cl LUYVIZYIGZWLEK-UHFFFAOYSA-N 0.000 claims 1
- MDXCTWOGPDQWFR-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(F)=CC=C1F MDXCTWOGPDQWFR-UHFFFAOYSA-N 0.000 claims 1
- IFJQAFSORYKHGW-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC=C(OC)C(N2C(C=CC(C)=C2)=O)=C1 IFJQAFSORYKHGW-UHFFFAOYSA-N 0.000 claims 1
- LVXOEVCZHWSZMZ-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-5-methylpyridin-2-one Chemical compound CC1=CC=C(C)C(N2C(C=CC(C)=C2)=O)=C1 LVXOEVCZHWSZMZ-UHFFFAOYSA-N 0.000 claims 1
- DMZNWOKZNPSKSP-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(Cl)C=CC=C1Cl DMZNWOKZNPSKSP-UHFFFAOYSA-N 0.000 claims 1
- CXIJPJZPSZHTNT-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(F)C=CC=C1F CXIJPJZPSZHTNT-UHFFFAOYSA-N 0.000 claims 1
- PIZBPTZVIPMEJT-UHFFFAOYSA-N 1-(2,6-dimethoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC=CC(OC)=C1N1C(=O)C=CC(C)=C1 PIZBPTZVIPMEJT-UHFFFAOYSA-N 0.000 claims 1
- BHBNMKITFOZDAB-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(C)C=CC=C1C BHBNMKITFOZDAB-UHFFFAOYSA-N 0.000 claims 1
- MJWRQZILSOKOTB-UHFFFAOYSA-N 1-(2-methoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC=CC=C1N1C(=O)C=CC(C)=C1 MJWRQZILSOKOTB-UHFFFAOYSA-N 0.000 claims 1
- GAHWJIZKEGFRLL-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-5-methylpyridin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1N1C(=O)C=CC(C)=C1 GAHWJIZKEGFRLL-UHFFFAOYSA-N 0.000 claims 1
- KXSZGLHSEASUBA-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(C)C(C)=C1 KXSZGLHSEASUBA-UHFFFAOYSA-N 0.000 claims 1
- RMHNSSKWHOINQA-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 RMHNSSKWHOINQA-UHFFFAOYSA-N 0.000 claims 1
- CEKMQLXFPZYWRU-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC(OC)=CC(N2C(C=CC(C)=C2)=O)=C1 CEKMQLXFPZYWRU-UHFFFAOYSA-N 0.000 claims 1
- DLAIQUGBQRXOBE-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(C)=CC(C)=C1 DLAIQUGBQRXOBE-UHFFFAOYSA-N 0.000 claims 1
- NUUFOILDYXVXLL-UHFFFAOYSA-N 1-(3-methoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC=CC(N2C(C=CC(C)=C2)=O)=C1 NUUFOILDYXVXLL-UHFFFAOYSA-N 0.000 claims 1
- CPJBLJUDFSFZEP-UHFFFAOYSA-N 1-[2,3-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(C(F)(F)F)=C1C(F)(F)F CPJBLJUDFSFZEP-UHFFFAOYSA-N 0.000 claims 1
- WMCCIACZTXJBNZ-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WMCCIACZTXJBNZ-UHFFFAOYSA-N 0.000 claims 1
- QQOSQRFHCXTCMT-UHFFFAOYSA-N 1-[2,6-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(C(F)(F)F)C=CC=C1C(F)(F)F QQOSQRFHCXTCMT-UHFFFAOYSA-N 0.000 claims 1
- LZWXKBBDHOJVPZ-UHFFFAOYSA-N 1-[3,4-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(C(F)(F)F)C(C(F)(F)F)=C1 LZWXKBBDHOJVPZ-UHFFFAOYSA-N 0.000 claims 1
- JQCDQYWMVOPHJK-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JQCDQYWMVOPHJK-UHFFFAOYSA-N 0.000 claims 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- VYXSRCVSKXRDAN-UHFFFAOYSA-N 5-methyl-1-(2-methylphenyl)pyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1C VYXSRCVSKXRDAN-UHFFFAOYSA-N 0.000 claims 1
- NDGCMBKTLPWHDG-UHFFFAOYSA-N 5-methyl-1-(3-methylphenyl)pyridin-2-one Chemical compound CC1=CC=CC(N2C(C=CC(C)=C2)=O)=C1 NDGCMBKTLPWHDG-UHFFFAOYSA-N 0.000 claims 1
- RRHMWKBGPCGEOI-UHFFFAOYSA-N 5-methyl-1-[2-(trifluoromethyl)phenyl]pyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1C(F)(F)F RRHMWKBGPCGEOI-UHFFFAOYSA-N 0.000 claims 1
- IKTCWTVJVXLKRU-UHFFFAOYSA-N 5-methyl-1-[4-(trifluoromethyl)phenyl]pyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1 IKTCWTVJVXLKRU-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 210000000626 ureter Anatomy 0.000 claims 1
Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Dermatology (AREA)
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Applications Claiming Priority (2)
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| CNA2005100314457A CN1846699A (zh) | 2005-04-13 | 2005-04-13 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
| CN200510031445.7 | 2005-04-13 |
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| RU2007141892A true RU2007141892A (ru) | 2009-05-20 |
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| EP (1) | EP1878428A4 (enExample) |
| JP (1) | JP2008535871A (enExample) |
| KR (1) | KR20080018857A (enExample) |
| CN (2) | CN1846699A (enExample) |
| AU (1) | AU2006233433A1 (enExample) |
| CA (1) | CA2603763A1 (enExample) |
| RU (1) | RU2007141892A (enExample) |
| TW (1) | TW200808315A (enExample) |
| WO (1) | WO2006108354A1 (enExample) |
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| US9733625B2 (en) | 2006-03-20 | 2017-08-15 | General Electric Company | Trip optimization system and method for a train |
| US8924049B2 (en) | 2003-01-06 | 2014-12-30 | General Electric Company | System and method for controlling movement of vehicles |
| JP4614884B2 (ja) | 2003-11-14 | 2011-01-19 | シャンハイ ゲノミックス インク | ピリドンの誘導体とその使用 |
| CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
| PT1928454E (pt) | 2005-05-10 | 2014-12-04 | Intermune Inc | Derivativos da piridona para modulação do sistema de proteína quinase ativada pelo stress |
| US9689681B2 (en) | 2014-08-12 | 2017-06-27 | General Electric Company | System and method for vehicle operation |
| US8370006B2 (en) | 2006-03-20 | 2013-02-05 | General Electric Company | Method and apparatus for optimizing a train trip using signal information |
| US8126601B2 (en) | 2006-03-20 | 2012-02-28 | General Electric Company | System and method for predicting a vehicle route using a route network database |
| US9156477B2 (en) | 2006-03-20 | 2015-10-13 | General Electric Company | Control system and method for remotely isolating powered units in a vehicle system |
| US8290645B2 (en) | 2006-03-20 | 2012-10-16 | General Electric Company | Method and computer software code for determining a mission plan for a powered system when a desired mission parameter appears unobtainable |
| CN101652138B (zh) * | 2007-09-19 | 2011-07-06 | 中南大学 | 1-取代芳基-2（1h）-吡啶酮化合物的新医药用途 |
| CN101235013A (zh) | 2008-03-10 | 2008-08-06 | 广东东阳光药业有限公司 | 结晶型1-（3-氟苯基）-5-甲基-2-（1h）吡啶酮、其制备方法、及其组合物和应用 |
| US8304413B2 (en) | 2008-06-03 | 2012-11-06 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US20100099719A1 (en) * | 2008-10-21 | 2010-04-22 | Dierepharma, Inc. | Composition and method for treating proteinuria |
| US7566729B1 (en) | 2008-11-10 | 2009-07-28 | Intermune, Inc. | Modifying pirfenidone treatment for patients with atypical liver function |
| US7635707B1 (en) | 2008-11-10 | 2009-12-22 | Intermune, Inc. | Pirfenidone treatment for patients with atypical liver function |
| US8016980B2 (en) | 2008-11-25 | 2011-09-13 | Dixie Consumer Products Llc | Paper products |
| US9834237B2 (en) | 2012-11-21 | 2017-12-05 | General Electric Company | Route examining system and method |
| CN101921225B (zh) * | 2009-06-11 | 2013-04-03 | 北京凯得尔森生物技术有限公司 | 吡啡尼酮类化合物、其制备方法和应用 |
| US8084475B2 (en) | 2009-12-04 | 2011-12-27 | Intermune, Inc. | Pirfenidone therapy and inducers of cytochrome P450 |
| US7816383B1 (en) | 2009-12-04 | 2010-10-19 | Intermune, Inc. | Methods of administering pirfenidone therapy |
| JP6021117B2 (ja) | 2011-01-31 | 2016-11-02 | ジェノア ファーマシューティカルズ，インク． | エアロゾルのピルフェニドンおよびピリドンアナログの化合物、および、その使用 |
| US10105356B2 (en) | 2011-01-31 | 2018-10-23 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| MX2015000830A (es) | 2012-07-18 | 2015-10-26 | Sunshine Lake Pharma Co Ltd | Derivados heterociclicos nitrogenosos y su aplicacion en farmacos. |
| CA2819967C (en) | 2012-08-31 | 2016-03-22 | Intermune, Inc. | Use of pirfenidone concomitantly with ciprofloxacin |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US9669851B2 (en) | 2012-11-21 | 2017-06-06 | General Electric Company | Route examination system and method |
| US9682716B2 (en) | 2012-11-21 | 2017-06-20 | General Electric Company | Route examining system and method |
| US9902712B2 (en) | 2013-12-19 | 2018-02-27 | Sunshine Lake Pharma Co., Ltd. | Nitrogenous heterocyclic derivatives and their application in drugs |
| EP4491180A1 (en) | 2014-01-10 | 2025-01-15 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| EP3117220B1 (en) * | 2014-03-12 | 2020-07-08 | Icahn School of Medicine at Mount Sinai | Method for identifying kidney allograft recipients at risk for chronic injury |
| KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
| WO2015200887A2 (en) | 2014-06-26 | 2015-12-30 | Icahn School Of Medicine At Mount Sinai | Method for diagnosing subclinical and clinical acute rejection by analysis of predictive gene sets |
| EP3194025A4 (en) * | 2014-09-18 | 2018-05-23 | Rush University Medical Center | Methods for preventing or treating osteoarthritis |
| DE102015217418A1 (de) | 2015-09-11 | 2017-03-16 | Mühlbauer Technology Gmbh | Radikalisch polymerisierbares Dentalmaterial |
| EP3308765B1 (de) | 2016-10-17 | 2022-07-13 | Mühlbauer Technology GmbH | Radikalisch polymerisierbare verbindung |
| WO2019011163A1 (en) * | 2017-07-14 | 2019-01-17 | Sunshine Lake Pharma Co., Ltd. | PROCESS FOR THE PREPARATION OF A PYRIMIDONE COMPOUND |
| WO2019204267A1 (en) | 2018-04-16 | 2019-10-24 | Icahn School Of Medicine At Mount Sinai | Method and kits for prediction of acute rejection and renal allograft loss using pre-transplant transcriptomic signatures in recipient blood |
| CN113274389B (zh) * | 2021-07-09 | 2022-11-08 | 中南大学 | 氟非尼酮在制备治疗急性肺损伤药物中的应用 |
| CN113456636A (zh) * | 2021-07-09 | 2021-10-01 | 中南大学 | 一种氟非尼酮在制备急性肝损伤药物中的应用 |
| CN114716365B (zh) * | 2022-01-04 | 2024-03-01 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮化合物或其可药用盐在治疗肺纤维化中的应用 |
| WO2024235145A1 (zh) * | 2023-05-12 | 2024-11-21 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮及内过氧化物的制备和应用 |
| CN118526493A (zh) * | 2023-10-30 | 2024-08-23 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮化合物在治疗癌症和缓解纤维化中的应用 |
| CN120053452B (zh) * | 2023-11-30 | 2025-12-05 | 长沙晶易医药科技股份有限公司 | 一种2,4-二取代-5-氟嘧啶衍生物的新用途 |
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| US4042699A (en) | 1972-12-18 | 1977-08-16 | Affiliated Medical Research, Inc. | Method for reducing serum glucose levels |
| US4052509A (en) | 1972-12-18 | 1977-10-04 | Affiliated Medical Research, Inc. | Method for reducing serum uric acid levels |
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| JPH02215719A (ja) | 1989-02-15 | 1990-08-28 | Yamauchi Akitomo | 線維化病変組織の修復並びに線維化病変の阻止剤 |
| US5716632A (en) | 1989-11-22 | 1998-02-10 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| US5310562A (en) * | 1989-11-22 | 1994-05-10 | Margolin Solomon B | Composition and method for reparation and prevention of fibrotic lesions |
| US5518729A (en) | 1989-11-22 | 1996-05-21 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| CN2114190U (zh) | 1992-01-09 | 1992-08-26 | 王刚 | 恒流一体化集成电源器件 |
| US5716623A (en) * | 1994-12-07 | 1998-02-10 | Immunex Corporation | Isolated Herpesvirus saimiri proteins that bind MHC Class II molecules |
| JP3496553B2 (ja) * | 1998-08-07 | 2004-02-16 | 株式会社高尾 | 弾球遊技機 |
| CN1218942C (zh) * | 2002-06-11 | 2005-09-14 | 中南大学湘雅医学院 | 抗纤维化吡啶酮化合物及其生产工艺方法 |
| CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
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2005
- 2005-04-13 CN CNA2005100314457A patent/CN1846699A/zh active Pending
-
2006
- 2006-04-11 AU AU2006233433A patent/AU2006233433A1/en not_active Abandoned
- 2006-04-11 RU RU2007141892/15A patent/RU2007141892A/ru not_active Application Discontinuation
- 2006-04-11 JP JP2008505716A patent/JP2008535871A/ja active Pending
- 2006-04-11 WO PCT/CN2006/000651 patent/WO2006108354A1/zh not_active Ceased
- 2006-04-11 CA CA002603763A patent/CA2603763A1/en not_active Abandoned
- 2006-04-11 KR KR1020077018590A patent/KR20080018857A/ko not_active Ceased
- 2006-04-11 CN CN2006800002161A patent/CN1953749B/zh active Active
- 2006-04-11 EP EP06722303A patent/EP1878428A4/en not_active Withdrawn
- 2006-08-04 TW TW095128659A patent/TW200808315A/zh unknown
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2007
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2008
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2009
- 2009-06-25 US US12/491,506 patent/US20090258911A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2603763A1 (en) | 2006-10-19 |
| EP1878428A4 (en) | 2008-09-03 |
| WO2006108354A1 (fr) | 2006-10-19 |
| US20090005424A9 (en) | 2009-01-01 |
| TW200808315A (en) | 2008-02-16 |
| CN1953749B (zh) | 2010-04-14 |
| US20080319027A1 (en) | 2008-12-25 |
| CN1846699A (zh) | 2006-10-18 |
| AU2006233433A1 (en) | 2006-10-19 |
| CN1953749A (zh) | 2007-04-25 |
| KR20080018857A (ko) | 2008-02-28 |
| US20070203203A1 (en) | 2007-08-30 |
| JP2008535871A (ja) | 2008-09-04 |
| EP1878428A1 (en) | 2008-01-16 |
| US20090258911A1 (en) | 2009-10-15 |
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