JP2000509047A - ３―アルコキシピリジン―２―カルボキサミドエステル類、その製法および薬剤としてのその使用 - Google Patents
３―アルコキシピリジン―２―カルボキサミドエステル類、その製法および薬剤としてのその使用Info
- Publication number
- JP2000509047A JP2000509047A JP09538479A JP53847997A JP2000509047A JP 2000509047 A JP2000509047 A JP 2000509047A JP 09538479 A JP09538479 A JP 09538479A JP 53847997 A JP53847997 A JP 53847997A JP 2000509047 A JP2000509047 A JP 2000509047A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- compound
- alkyl
- hydrogen
- 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.)
- Pending
Links
- 239000003814 drug Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 4
- 230000036570 collagen biosynthesis Effects 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 230000003176 fibrotic effect Effects 0.000 claims abstract description 6
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- -1 phenylbutyl Chemical group 0.000 claims description 14
- 102000008186 Collagen Human genes 0.000 claims description 11
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- 229920001436 collagen Polymers 0.000 claims description 11
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 10
- 206010016654 Fibrosis Diseases 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims description 10
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims description 10
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 3
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- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 125000000946 retinyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000037390 scarring Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 230000001766 physiological effect Effects 0.000 claims 1
- 230000035479 physiological effects, processes and functions Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000004471 Glycine Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 5
- YVBCULSIZWMTFY-UHFFFAOYSA-N Heptan-4-ol Chemical compound CCCC(O)CCC YVBCULSIZWMTFY-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 4
- MQFRBEILHZPVQG-UHFFFAOYSA-N 3-methoxypyridine-2-carboxylic acid;hydrochloride Chemical compound Cl.COC1=CC=CN=C1C(O)=O MQFRBEILHZPVQG-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
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- 102000029816 Collagenase Human genes 0.000 description 3
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- 238000001816 cooling Methods 0.000 description 3
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- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 description 2
- RYGXNMUVOHCPBF-UHFFFAOYSA-N 4-chloro-3-methoxy-2-methylpyridine Chemical compound COC1=C(C)N=CC=C1Cl RYGXNMUVOHCPBF-UHFFFAOYSA-N 0.000 description 2
- 208000032544 Cicatrix Diseases 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- LFFYDYKNMMFJMR-UHFFFAOYSA-N octyl 2-[(3-methoxypyridine-2-carbonyl)amino]acetate Chemical compound CCCCCCCCOC(=O)CNC(=O)C1=NC=CC=C1OC LFFYDYKNMMFJMR-UHFFFAOYSA-N 0.000 description 1
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- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
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- SLZJZJGPZQUKMO-UHFFFAOYSA-N propyl 2-[(3-methoxypyridine-2-carbonyl)amino]acetate Chemical compound CCCOC(=O)CNC(=O)C1=NC=CC=C1OC SLZJZJGPZQUKMO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1996/001793 WO1997041103A1 (fr) | 1996-04-30 | 1996-04-30 | Esters d'amide de 3-alcoxypyridine-2-acide carboxylique, leur preparation et leur utilisation comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000509047A true JP2000509047A (ja) | 2000-07-18 |
Family
ID=8166212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09538479A Pending JP2000509047A (ja) | 1996-04-30 | 1996-04-30 | ３―アルコキシピリジン―２―カルボキサミドエステル類、その製法および薬剤としてのその使用 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0900202A1 (fr) |
| JP (1) | JP2000509047A (fr) |
| KR (1) | KR20000065090A (fr) |
| AU (1) | AU5762896A (fr) |
| CA (1) | CA2253282A1 (fr) |
| NO (1) | NO984878L (fr) |
| WO (1) | WO1997041103A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003519215A (ja) * | 2000-01-06 | 2003-06-17 | アベンティス・クロップサイエンス・エス・アー | ３−ヒドロキシピコリン酸誘導体の調製方法 |
| JP2009541486A (ja) * | 2006-06-26 | 2009-11-26 | ザ プロクター アンド ギャンブル カンパニー | プロリルヒドロキシラーゼ阻害剤および使用方法 |
| WO2016190420A1 (fr) * | 2015-05-28 | 2016-12-01 | 日本たばこ産業株式会社 | Procédé de traitement ou de prévention de la néphropathie diabétique |
| JP2018504389A (ja) * | 2014-12-30 | 2018-02-15 | ダウ アグロサイエンシィズ エルエルシー | 殺真菌活性を有するピコリンアミド |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4590157B2 (ja) * | 2001-03-21 | 2010-12-01 | アイシス イノヴェイション リミテッド | アッセイ、方法および手段 |
| DK2298301T3 (en) * | 2001-12-06 | 2018-10-01 | Fibrogen Inc | MEDICINALS FOR TREATMENT OF ANEMIA ASSOCIATED WITH Kidney Disease |
| US7588924B2 (en) | 2006-03-07 | 2009-09-15 | Procter & Gamble Company | Crystal of hypoxia inducible factor 1 alpha prolyl hydroxylase |
| RS54010B1 (sr) | 2009-11-06 | 2015-10-30 | Aerpio Therapeutics Inc. | Inhibitori prolil hidroksilaze |
| WO2012170439A1 (fr) | 2011-06-06 | 2012-12-13 | The Ohio State University | Procédés de stabilisation d'un facteur 2-alpha induit par l'hypoxie en tant que méthode de traitement du cancer |
| NO2686520T3 (fr) | 2011-06-06 | 2018-03-17 | ||
| EP2938191B1 (fr) | 2012-12-28 | 2018-01-31 | Dow AgroSciences LLC | Mélanges fongicides synergiques destinés au contrôle d'infection fongique dans les céréales |
| JP2016521747A (ja) | 2013-06-13 | 2016-07-25 | アケビア セラピューティクス インコーポレイテッドＡｋｅｂｉａ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 貧血治療のための組成物及び方法 |
| MY180626A (en) | 2013-11-15 | 2020-12-03 | Akebia Therapeutics Inc | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
| US20170290333A1 (en) | 2014-12-30 | 2017-10-12 | Dow Agrosciences Llc | Picolinamide compounds with fungicidal activity |
| MX2017008444A (es) | 2014-12-30 | 2017-10-02 | Dow Agrosciences Llc | Picolinamidas como fungicidas. |
| MX2017008439A (es) * | 2014-12-30 | 2017-10-02 | Dow Agrosciences Llc | Compuestos de picolinamida con actividad fungicida. |
| AU2015374459A1 (en) | 2014-12-30 | 2017-06-29 | Dow Agrosciences Llc | Picolinamide compounds with fungicidal activity |
| US10150734B2 (en) | 2015-01-23 | 2018-12-11 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
| US11324734B2 (en) | 2015-04-01 | 2022-05-10 | Akebia Therapeutics, Inc. | Compositions and methods for treating anemia |
| TW201842851A (zh) | 2017-05-02 | 2018-12-16 | 美商陶氏農業科學公司 | 用於穀類中的真菌防治之協同性混合物 |
| TWI774761B (zh) | 2017-05-02 | 2022-08-21 | 美商科迪華農業科技有限責任公司 | 用於穀物中的真菌防治之協同性混合物 |
| US11191269B2 (en) | 2017-05-02 | 2021-12-07 | Dow Agrosciences Llc | Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses |
| BR102019004480B1 (pt) | 2018-03-08 | 2023-03-28 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
| US11713298B2 (en) | 2018-05-09 | 2023-08-01 | Akebia Therapeutics, Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| KR20210076072A (ko) | 2018-10-15 | 2021-06-23 | 코르테바 애그리사이언스 엘엘씨 | 옥시피콜린아미드의 합성 방법 |
| CN114554848A (zh) | 2019-10-18 | 2022-05-27 | 科迪华农业科技有限责任公司 | 用于合成吡啶酰胺的方法 |
| US11524939B2 (en) | 2019-11-13 | 2022-12-13 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid |
| WO2021117767A1 (fr) | 2019-12-10 | 2021-06-17 | 田辺三菱製薬株式会社 | Procédé de production d'un dérivé d'acide hétéroarylcarboxamide acétique contenant de l'azote |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE149485T1 (de) * | 1993-11-02 | 1997-03-15 | Hoechst Ag | Substituierte heterocyclische carbonsäureamidester, ihre herstellung und ihre verwendung als arzneimittel |
-
1996
- 1996-04-30 CA CA002253282A patent/CA2253282A1/fr not_active Abandoned
- 1996-04-30 EP EP96914152A patent/EP0900202A1/fr not_active Withdrawn
- 1996-04-30 WO PCT/EP1996/001793 patent/WO1997041103A1/fr not_active Ceased
- 1996-04-30 KR KR1019980708679A patent/KR20000065090A/ko not_active Withdrawn
- 1996-04-30 AU AU57628/96A patent/AU5762896A/en not_active Abandoned
- 1996-04-30 JP JP09538479A patent/JP2000509047A/ja active Pending
-
1998
- 1998-10-19 NO NO984878A patent/NO984878L/no not_active Application Discontinuation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003519215A (ja) * | 2000-01-06 | 2003-06-17 | アベンティス・クロップサイエンス・エス・アー | ３−ヒドロキシピコリン酸誘導体の調製方法 |
| JP2009541486A (ja) * | 2006-06-26 | 2009-11-26 | ザ プロクター アンド ギャンブル カンパニー | プロリルヒドロキシラーゼ阻害剤および使用方法 |
| JP2018504389A (ja) * | 2014-12-30 | 2018-02-15 | ダウ アグロサイエンシィズ エルエルシー | 殺真菌活性を有するピコリンアミド |
| JP2018505865A (ja) * | 2014-12-30 | 2018-03-01 | ダウ アグロサイエンシィズ エルエルシー | 殺真菌活性を有するピコリンアミド |
| WO2016190420A1 (fr) * | 2015-05-28 | 2016-12-01 | 日本たばこ産業株式会社 | Procédé de traitement ou de prévention de la néphropathie diabétique |
| JPWO2016190420A1 (ja) * | 2015-05-28 | 2018-03-15 | 日本たばこ産業株式会社 | 糖尿病性腎症を治療又は予防する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NO984878D0 (no) | 1998-10-19 |
| WO1997041103A1 (fr) | 1997-11-06 |
| NO984878L (no) | 1998-12-29 |
| CA2253282A1 (fr) | 1997-11-06 |
| AU5762896A (en) | 1997-11-19 |
| EP0900202A1 (fr) | 1999-03-10 |
| KR20000065090A (ko) | 2000-11-06 |
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