NO312365B1 - Substituerte isokinolin-3-karboksylsyreamider, deres fremstilling og deres anvendelse til fremstilling av legemiddel - Google Patents
Substituerte isokinolin-3-karboksylsyreamider, deres fremstilling og deres anvendelse til fremstilling av legemiddel Download PDFInfo
- Publication number
- NO312365B1 NO312365B1 NO19984877A NO984877A NO312365B1 NO 312365 B1 NO312365 B1 NO 312365B1 NO 19984877 A NO19984877 A NO 19984877A NO 984877 A NO984877 A NO 984877A NO 312365 B1 NO312365 B1 NO 312365B1
- Authority
- NO
- Norway
- Prior art keywords
- chlorine
- formula
- hydrogen
- alkoxy
- compounds
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 18
- 239000003814 drug Substances 0.000 title claims description 9
- 229940079593 drug Drugs 0.000 title claims description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
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- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NZSBEZMTLFUYJD-UHFFFAOYSA-N methyl 1,6,7-trichloro-4-hydroxyisoquinoline-3-carboxylate Chemical compound C1=C(Cl)C(Cl)=CC2=C(O)C(C(=O)OC)=NC(Cl)=C21 NZSBEZMTLFUYJD-UHFFFAOYSA-N 0.000 description 1
- JCLXQWPJRSUMFT-UHFFFAOYSA-N methyl 1-chloro-4-hydroxyisoquinoline-3-carboxylate Chemical compound C1=CC=CC2=C(O)C(C(=O)OC)=NC(Cl)=C21 JCLXQWPJRSUMFT-UHFFFAOYSA-N 0.000 description 1
- BPSBCFXSFAXTIV-UHFFFAOYSA-N methyl 2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetate Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)OC)=NC(Cl)=C21 BPSBCFXSFAXTIV-UHFFFAOYSA-N 0.000 description 1
- SNAIQLNIIAIHIC-UHFFFAOYSA-N methyl 2-[(8-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetate Chemical compound ClC1=CC=CC2=C(O)C(C(=O)NCC(=O)OC)=NC=C21 SNAIQLNIIAIHIC-UHFFFAOYSA-N 0.000 description 1
- JOURGLFWVLLAPY-UHFFFAOYSA-N methyl 4-hydroxy-1-oxo-2h-isoquinoline-3-carboxylate Chemical compound C1=CC=C2C(O)=C(C(=O)OC)NC(=O)C2=C1 JOURGLFWVLLAPY-UHFFFAOYSA-N 0.000 description 1
- WMQGVBYZDZCNKC-UHFFFAOYSA-N methyl 6,7-dichloro-4-hydroxy-1-oxo-2h-isoquinoline-3-carboxylate Chemical compound ClC1=C(Cl)C=C2C(O)=C(C(=O)OC)NC(=O)C2=C1 WMQGVBYZDZCNKC-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- KWDCBYBOHQWCKS-UHFFFAOYSA-N n-(2-aminoacetyl)-3-hydroxyquinoline-2-carboxamide Chemical class C1=CC=C2C=C(O)C(C(=O)NC(=O)CN)=NC2=C1 KWDCBYBOHQWCKS-UHFFFAOYSA-N 0.000 description 1
- IXAKZRUKCFYOPF-UHFFFAOYSA-N n-(2-hydroxyethyl)isoquinoline-3-carboxamide Chemical class C1=CC=C2C=NC(C(=O)NCCO)=CC2=C1 IXAKZRUKCFYOPF-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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- NWNGDHADXSESGZ-UHFFFAOYSA-N pentyl 2-[(1-chloro-4-hydroxy-6-methoxyisoquinoline-3-carbonyl)amino]acetate Chemical compound C1=CC(OC)=CC2=C(O)C(C(=O)NCC(=O)OCCCCC)=NC(Cl)=C21 NWNGDHADXSESGZ-UHFFFAOYSA-N 0.000 description 1
- SDEMTXKOSYZTHN-UHFFFAOYSA-N pentyl 2-[(1-chloro-4-hydroxy-7-methoxyisoquinoline-3-carbonyl)amino]acetate Chemical compound C1=C(OC)C=CC2=C(O)C(C(=O)NCC(=O)OCCCCC)=NC(Cl)=C21 SDEMTXKOSYZTHN-UHFFFAOYSA-N 0.000 description 1
- HKTWQRFIHHMWGI-UHFFFAOYSA-N pentyl 2-[(1-chloro-4-hydroxy-7-phenylmethoxyisoquinoline-3-carbonyl)amino]acetate Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)OCCCCC)=NC(Cl)=C2C=C1OCC1=CC=CC=C1 HKTWQRFIHHMWGI-UHFFFAOYSA-N 0.000 description 1
- OYFQFSFYDOUOGM-UHFFFAOYSA-N pentyl 2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]acetate Chemical compound C1=C(OC(C)C)C=CC2=C(O)C(C(=O)NCC(=O)OCCCCC)=NC(Cl)=C21 OYFQFSFYDOUOGM-UHFFFAOYSA-N 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
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- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
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- 230000009467 reduction Effects 0.000 description 1
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- 230000037390 scarring Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 238000012453 sprague-dawley rat model Methods 0.000 description 1
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- 210000004500 stellate cell Anatomy 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious 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
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19746287A DE19746287A1 (de) | 1997-10-20 | 1997-10-20 | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO984877D0 NO984877D0 (no) | 1998-10-19 |
| NO984877L NO984877L (no) | 1999-04-21 |
| NO312365B1 true NO312365B1 (no) | 2002-04-29 |
Family
ID=7846053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19984877A NO312365B1 (no) | 1997-10-20 | 1998-10-19 | Substituerte isokinolin-3-karboksylsyreamider, deres fremstilling og deres anvendelse til fremstilling av legemiddel |
Country Status (25)
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|---|---|
| US (1) | US6093730A (pt) |
| EP (2) | EP0911340B1 (pt) |
| JP (2) | JP3782591B2 (pt) |
| KR (1) | KR100618922B1 (pt) |
| CN (1) | CN1117079C (pt) |
| AR (1) | AR013696A1 (pt) |
| AT (2) | ATE299148T1 (pt) |
| AU (1) | AU755714B2 (pt) |
| BR (1) | BR9804504B1 (pt) |
| CA (2) | CA2250664A1 (pt) |
| CZ (1) | CZ337298A3 (pt) |
| DE (3) | DE19746287A1 (pt) |
| DK (2) | DK0911340T3 (pt) |
| ES (2) | ES2245471T3 (pt) |
| HK (1) | HK1019605A1 (pt) |
| HU (1) | HUP9802422A3 (pt) |
| ID (1) | ID21115A (pt) |
| IL (1) | IL126638A0 (pt) |
| NO (1) | NO312365B1 (pt) |
| NZ (1) | NZ332363A (pt) |
| PL (1) | PL192354B1 (pt) |
| PT (1) | PT911340E (pt) |
| SG (1) | SG87776A1 (pt) |
| TR (1) | TR199802106A2 (pt) |
| ZA (1) | ZA989505B (pt) |
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| AU2001275014A1 (en) * | 2000-05-30 | 2001-12-11 | Neurogen Corporation | Imidazoloisoquinolines |
| US6762318B2 (en) * | 2001-12-03 | 2004-07-13 | Novo Nordisk A/S | Glucagon antagonists |
| US8318703B2 (en) | 2001-12-06 | 2012-11-27 | Fibrogen, Inc. | Methods for improving kidney function |
| EP2324834B1 (en) * | 2001-12-06 | 2019-05-08 | Fibrogen, Inc. | Methods of Increasing Endogenous Erythropoietin (EPO) |
| EP2295060B1 (en) | 2001-12-06 | 2018-10-31 | Fibrogen, Inc. | Treatment or prevention of ischemic or hypoxic conditions |
| US8124582B2 (en) * | 2002-12-06 | 2012-02-28 | Fibrogen, Inc. | Treatment of diabetes |
| US7618940B2 (en) | 2002-12-06 | 2009-11-17 | Fibrogen, Inc. | Fat regulation |
| US20060251638A1 (en) * | 2003-06-06 | 2006-11-09 | Volkmar Guenzler-Pukall | Cytoprotection through the use of hif hydroxylase inhibitors |
| DK1644336T3 (da) * | 2003-06-06 | 2011-05-09 | Fibrogen Inc | Nitrogenholdige heteroarylforbindelser og deres anvendelse til forøgelse af endogent erythropoietin |
| US8614204B2 (en) * | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| WO2006133391A2 (en) * | 2005-06-06 | 2006-12-14 | Fibrogen, Inc. | Improved treatment for anemia using a hif-alpha stabilising agent |
| US8530404B2 (en) | 2005-06-15 | 2013-09-10 | Fibrogen, Inc. | Compounds and methods for treatment of cancer |
| WO2007070359A2 (en) | 2005-12-09 | 2007-06-21 | Amgen Inc. | Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity, and compositions, and uses thereof |
| EP2476669A1 (en) | 2006-01-27 | 2012-07-18 | Fibrogen, Inc. | Cyanoisoquinoline compounds and methods of use thereof |
| US7745461B1 (en) | 2006-02-27 | 2010-06-29 | Alcon Research, Ltd. | Method of treating dry eye disorders |
| WO2007101204A1 (en) * | 2006-02-27 | 2007-09-07 | Alcon Research, Ltd. | Method of treating glaucoma |
| KR100959538B1 (ko) * | 2006-03-30 | 2010-05-27 | 엘지전자 주식회사 | 비디오 신호를 디코딩/인코딩하기 위한 방법 및 장치 |
| JP5111491B2 (ja) | 2006-04-04 | 2013-01-09 | フィブロジェン， インコーポレイテッド | ピロロ−およびピラゾロ−ピリミジン化合物、およびそれらの使用方法 |
| LT3357911T (lt) | 2006-06-26 | 2022-08-10 | Akebia Therapeutics Inc. | Prolilo hidroksilazės inhibitoriai ir naudojimo būdai |
| AU2007334323B2 (en) | 2006-12-18 | 2011-03-10 | Amgen Inc. | Naphthalenone compounds exhibiting prolyl hydroxylase inhibitory activity, compositions, and uses thereof |
| AU2007334321B2 (en) | 2006-12-18 | 2012-03-08 | Amgen Inc. | Azaquinolone based compounds exhibiting prolyl hydroxylase inhibitory activity, compositions, and uses thereof |
| US7569726B2 (en) | 2007-04-18 | 2009-08-04 | Amgen Inc. | Indanone derivatives that inhibit prolyl hydroxylase |
| ES2442847T3 (es) | 2007-04-18 | 2014-02-13 | Amgen, Inc | Quinolonas y azaquinolonas que inhiben la prolil hidroxilasa |
| EP2155746A2 (en) | 2007-05-04 | 2010-02-24 | Amgen, Inc | Diazaquinolones that inhibit prolyl hydroxylase activity |
| EP2150251B9 (en) | 2007-05-04 | 2013-02-27 | Amgen, Inc | Thienopyridine and thiazolopyridine derivatives that inhibit prolyl hydroxylase activity |
| US8962530B2 (en) * | 2007-06-27 | 2015-02-24 | Regents Of The University Of Colorado | Inflammatory bowel disease therapies |
| CN101497584B (zh) * | 2008-01-29 | 2010-12-22 | 首都医科大学 | 异喹啉-3-甲酰氨基酸苄酯及其制备和应用 |
| WO2009134754A1 (en) | 2008-04-28 | 2009-11-05 | Janssen Pharmaceutica Nv | Benzoimidazole glycinamides as prolyl hydroxylase inhibitors |
| WO2010056767A1 (en) | 2008-11-14 | 2010-05-20 | Fibrogen, Inc. | Thiochromene derivatives as hip hydroxylase inhibitors |
| AU2010271732B2 (en) * | 2009-07-17 | 2016-08-25 | Japan Tobacco Inc. | Triazolopyridine compound, and action thereof as prolyl hydroxylase inhibitor and erythropoietin production inducer |
| NO2686520T3 (pt) | 2011-06-06 | 2018-03-17 | ||
| EP2734504B1 (en) * | 2011-07-22 | 2016-09-14 | Beijing Betta Pharmaceuticals Co., Ltd | Polymorphic forms of compounds as prolyl hydroxylase inhibitor, and uses thereof |
| BR112014009910B1 (pt) | 2011-10-25 | 2020-06-30 | Janssen Pharmaceutica N.V. | sal di-hidrato de meglumina de ácido 1-(5,6-dicloro-1h-benzo[d]imidazol-2-il)-1h-pirazol-4-carboxílico, composição farmacêuticae pomada tópica |
| WO2013134660A1 (en) | 2012-03-09 | 2013-09-12 | Fibrogen, Inc. | 4 -hydroxy- isoquinoline compounds as hif hydroxylase inhibitors |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| WO2014014834A1 (en) * | 2012-07-16 | 2014-01-23 | Fibrogen, Inc. | Process for making isoquinoline compounds |
| EP3470397B1 (en) | 2012-07-16 | 2021-12-29 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
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| DE4015255A1 (de) * | 1990-05-12 | 1991-11-14 | Hoechst Ag | Oxalyl-aminosaeurederivate, verfahren zu ihrer herstellung und ihrer verwendung als arzneimittel zur inhibierung der prolyl-hydroxylase |
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| DE59401923D1 (de) * | 1993-11-02 | 1997-04-10 | Hoechst Ag | Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
| TW406076B (en) * | 1993-12-30 | 2000-09-21 | Hoechst Ag | Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals |
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| IL135495A (en) * | 1995-09-28 | 2002-12-01 | Hoechst Ag | Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid |
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1997
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