JP6290781B2 - [(3−ヒドロキシピリジン−2−カルボニル)アミノ]アルカン酸、エステル及びアミドの製造方法 - Google Patents
[(3−ヒドロキシピリジン−2−カルボニル)アミノ]アルカン酸、エステル及びアミドの製造方法 Download PDFInfo
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- JP6290781B2 JP6290781B2 JP2014514536A JP2014514536A JP6290781B2 JP 6290781 B2 JP6290781 B2 JP 6290781B2 JP 2014514536 A JP2014514536 A JP 2014514536A JP 2014514536 A JP2014514536 A JP 2014514536A JP 6290781 B2 JP6290781 B2 JP 6290781B2
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- acid
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- 0 *C(c(nc1)c([*-])cc1-c1ccccc1)=[U] Chemical compound *C(c(nc1)c([*-])cc1-c1ccccc1)=[U] 0.000 description 3
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
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- 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
- C07D213/79—Acids; Esters
-
- 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
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Enzymes And Modification Thereof (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161493536P | 2011-06-06 | 2011-06-06 | |
| US61/493,536 | 2011-06-06 | ||
| PCT/US2012/040833 WO2012170377A1 (en) | 2011-06-06 | 2012-06-05 | Process for preparing [(3-hydroxypyridine-2-carbonyl)amino]alkanoic acids, esters and amides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018020595A Division JP6510094B2 (ja) | 2011-06-06 | 2018-02-08 | [(3−ヒドロキシピリジン−2−カルボニル)アミノ]アルカン酸、エステル及びアミドの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014522409A JP2014522409A (ja) | 2014-09-04 |
| JP6290781B2 true JP6290781B2 (ja) | 2018-03-07 |
Family
ID=47262177
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014514536A Active JP6290781B2 (ja) | 2011-06-06 | 2012-06-05 | [(3−ヒドロキシピリジン−2−カルボニル)アミノ]アルカン酸、エステル及びアミドの製造方法 |
| JP2018020595A Active JP6510094B2 (ja) | 2011-06-06 | 2018-02-08 | [(3−ヒドロキシピリジン−2−カルボニル)アミノ]アルカン酸、エステル及びアミドの製造方法 |
| JP2019070979A Active JP6816195B2 (ja) | 2011-06-06 | 2019-04-03 | [(5−(ハロフェニル)−3−ヒドロキシピリジン−2−カルボニル)−アミノ]アルカン酸誘導体の調製における中間体としての5−((ハロフェニル)−3−ハロ−ピリジン−2−イル)−ニトリル誘導体 |
| JP2020213442A Active JP7039682B2 (ja) | 2011-06-06 | 2020-12-23 | [(5-(ハロフェニル)-3-ヒドロキシピリジン-2-カルボニル)-アミノ]アルカン酸誘導体の調製における中間体としての5-((ハロフェニル)-3-ハロ-ピリジン-2-イル)-ニトリル誘導体 |
| JP2022035813A Active JP7284309B2 (ja) | 2011-06-06 | 2022-03-09 | [(5-(ハロフェニル)-3-ヒドロキシピリジン-2-カルボニル)-アミノ]アルカン酸誘導体の調製における中間体としての5-((ハロフェニル)-3-ハロ-ピリジン-2-イル)-ニトリル誘導体 |
| JP2023081959A Active JP7685552B2 (ja) | 2011-06-06 | 2023-05-18 | [(5-(ハロフェニル)-3-ヒドロキシピリジン-2-カルボニル)-アミノ]アルカン酸誘導体の調製における中間体としての5-((ハロフェニル)-3-ハロ-ピリジン-2-イル)-ニトリル誘導体 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018020595A Active JP6510094B2 (ja) | 2011-06-06 | 2018-02-08 | [(3−ヒドロキシピリジン−2−カルボニル)アミノ]アルカン酸、エステル及びアミドの製造方法 |
| JP2019070979A Active JP6816195B2 (ja) | 2011-06-06 | 2019-04-03 | [(5−(ハロフェニル)−3−ヒドロキシピリジン−2−カルボニル)−アミノ]アルカン酸誘導体の調製における中間体としての5−((ハロフェニル)−3−ハロ−ピリジン−2−イル)−ニトリル誘導体 |
| JP2020213442A Active JP7039682B2 (ja) | 2011-06-06 | 2020-12-23 | [(5-(ハロフェニル)-3-ヒドロキシピリジン-2-カルボニル)-アミノ]アルカン酸誘導体の調製における中間体としての5-((ハロフェニル)-3-ハロ-ピリジン-2-イル)-ニトリル誘導体 |
| JP2022035813A Active JP7284309B2 (ja) | 2011-06-06 | 2022-03-09 | [(5-(ハロフェニル)-3-ヒドロキシピリジン-2-カルボニル)-アミノ]アルカン酸誘導体の調製における中間体としての5-((ハロフェニル)-3-ハロ-ピリジン-2-イル)-ニトリル誘導体 |
| JP2023081959A Active JP7685552B2 (ja) | 2011-06-06 | 2023-05-18 | [(5-(ハロフェニル)-3-ヒドロキシピリジン-2-カルボニル)-アミノ]アルカン酸誘導体の調製における中間体としての5-((ハロフェニル)-3-ハロ-ピリジン-2-イル)-ニトリル誘導体 |
Country Status (23)
| Country | Link |
|---|---|
| US (6) | US9145366B2 (enExample) |
| EP (5) | EP3290404B1 (enExample) |
| JP (6) | JP6290781B2 (enExample) |
| KR (5) | KR102000485B1 (enExample) |
| CN (1) | CN106518759B (enExample) |
| AU (4) | AU2012268426B2 (enExample) |
| CA (2) | CA2838194C (enExample) |
| CY (4) | CY1117177T1 (enExample) |
| DK (4) | DK3683209T3 (enExample) |
| ES (4) | ES2900572T3 (enExample) |
| HR (4) | HRP20151416T1 (enExample) |
| HU (4) | HUE034975T2 (enExample) |
| IL (1) | IL229775A (enExample) |
| LT (3) | LT3000808T (enExample) |
| MX (2) | MX337216B (enExample) |
| NO (1) | NO2686520T3 (enExample) |
| PL (4) | PL3290404T3 (enExample) |
| PT (4) | PT3290404T (enExample) |
| RS (3) | RS54517B1 (enExample) |
| RU (2) | RU2602083C2 (enExample) |
| SI (4) | SI2718265T1 (enExample) |
| SM (3) | SMT202000061T1 (enExample) |
| WO (1) | WO2012170377A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ601730A (en) | 2006-06-26 | 2014-04-30 | Akebia Therapeutics Inc | Prolyl hydroxylase inhibitors and methods of use |
| NO2686520T3 (enExample) | 2011-06-06 | 2018-03-17 | ||
| SMT202400092T1 (it) | 2013-06-13 | 2024-05-14 | Akebia Therapeutics Inc | Composizioni e metodi per il trattamento dell'anemia |
| EP3578546A1 (en) | 2013-11-15 | 2019-12-11 | Akebia Therapeutics Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
| WO2016034108A1 (zh) | 2014-09-02 | 2016-03-10 | 广东东阳光药业有限公司 | 喹啉酮类化合物及其应用 |
| HK1247201A1 (zh) | 2015-01-23 | 2018-09-21 | 阿克比治疗有限公司 | 2-(5-(3-氟苯基)-3-羟基吡啶甲醯胺)乙酸的固体形式、其组合物及用途 |
| EP3270922A4 (en) * | 2015-03-20 | 2018-08-01 | Akebia Therapeutics Inc. | Deuterium-enriched hypoxia-inducible factor prolyl hydroxylase enzyme inhibitors |
| CN106146395B (zh) | 2015-03-27 | 2019-01-01 | 沈阳三生制药有限责任公司 | 3-羟基吡啶化合物、其制备方法及其制药用途 |
| PL3277270T3 (pl) | 2015-04-01 | 2022-02-14 | Akebia Therapeutics, Inc. | Kompozycje i sposoby leczenia niedokrwistości |
| US10703724B2 (en) | 2016-12-13 | 2020-07-07 | Crystal Pharmaceutical (Suzhou) Co., Ltd. | Crystalline forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl] amino} acetic acid and processes for preparation thereof |
| IL269623B2 (en) * | 2017-03-29 | 2025-05-01 | Emerald Health Pharmaceuticals Inc | Cannabidiol derivatives as inhibitors of the hif prolyl hydroxylases activity |
| WO2019028150A1 (en) | 2017-08-01 | 2019-02-07 | Akebia Therapeutics, Inc. | COMPOSITIONS FOR USE IN METHODS OF TREATING HEMOGLOBINOPATHIES |
| CA3097219A1 (en) * | 2018-05-09 | 2019-11-14 | Akebia Therapeutics, Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| WO2020075199A1 (en) | 2018-10-12 | 2020-04-16 | Mylan Laboratories Limited | Polymorphic forms of vadadustat |
| WO2020108941A1 (en) | 2018-11-28 | 2020-06-04 | Sandoz Ag | Multi-component crystals of an orally available hif prolyl hydroxylase inhibitor |
| US12134600B2 (en) | 2019-04-26 | 2024-11-05 | Kaneka Corporation | Method for producing a vadadustat intermediate |
| US11524939B2 (en) | 2019-11-13 | 2022-12-13 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid |
| CN111087343B (zh) * | 2019-11-29 | 2022-02-18 | 万华化学集团股份有限公司 | 一种羟基吡啶配体及其制备方法和催化应用 |
| US12612367B2 (en) | 2019-12-10 | 2026-04-28 | Akebia Therapeutics, Inc. | Method for producing nitrogen-containing heteroarylcarboxamide acetic acid derivative |
| EP4094832A4 (en) | 2020-01-24 | 2024-04-17 | APS Japan Co., Ltd. | Photocatalyst unit and mask provided with photocatalyst unit |
| WO2022006427A1 (en) | 2020-07-02 | 2022-01-06 | Akebia Therapeutics, Inc. | Manufacturing process for 3,5-dichloropicolinonitrile for synthesis of vadadustat |
| GB202011431D0 (en) * | 2020-07-23 | 2020-09-09 | Johnson Matthey Plc | Polymorphs of vadadustat and methods for preparing the polymorphs |
| EP4447963A1 (en) | 2021-12-17 | 2024-10-23 | Akebia Therapeutics Inc. | Selective phd1 inhibitor compounds, compositions, and methods of use |
| WO2024165507A1 (en) | 2023-02-06 | 2024-08-15 | Institut National de la Santé et de la Recherche Médicale | Use of hif-1α stabilizing agents for the treatment of type i interferonopathies |
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| US3655679A (en) * | 1969-06-25 | 1972-04-11 | Merck & Co Inc | Certain aryl pyridine carboxylic acid derivatives |
| US3703582A (en) * | 1970-04-20 | 1972-11-21 | Merck & Co Inc | Aryl pyridine carboxylic acids in the treatment of inflammation |
| US3894920A (en) | 1971-12-21 | 1975-07-15 | Sagami Chem Res | Process for preparing alkyl-substituted 3,6-dihydro-o-dioxin derivatives |
| US4016287A (en) | 1972-07-17 | 1977-04-05 | Boehringer Ingelheim Gmbh | Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof |
| TW219933B (enExample) | 1990-02-26 | 1994-02-01 | Lilly Co Eli | |
| US5405613A (en) | 1991-12-11 | 1995-04-11 | Creative Nutrition Canada Corp. | Vitamin/mineral composition |
| TW352384B (en) | 1992-03-24 | 1999-02-11 | Hoechst Ag | Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals |
| DE4219158A1 (de) | 1992-06-11 | 1993-12-16 | Thomae Gmbh Dr K | Biphenylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| EP0650960B1 (de) | 1993-11-02 | 1997-03-05 | Hoechst Aktiengesellschaft | Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
| ATE149486T1 (de) | 1993-11-02 | 1997-03-15 | Hoechst Ag | Substituierte heterocyclische carbonsäureamide, 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 |
| DE4410480A1 (de) | 1994-03-25 | 1995-09-28 | Hoechst Ag | Sulfonamidocarbonylpyridin-2-carbonsäureesteramide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE4410423A1 (de) | 1994-03-25 | 1995-09-28 | Hoechst Ag | Sulfonamidocarbonylpyridin-2-carbonsäureamide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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| JPH09221476A (ja) | 1995-12-15 | 1997-08-26 | Otsuka Pharmaceut Co Ltd | 医薬組成物 |
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| DE19620041A1 (de) | 1996-05-17 | 1998-01-29 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| DE19650215A1 (de) | 1996-12-04 | 1998-06-10 | Hoechst Ag | 3-Hydroxypyridin-2-carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US6420427B1 (en) | 1997-10-09 | 2002-07-16 | Ono Pharmaceutical Co., Ltd. | Aminobutyric acid derivatives |
| DE19746287A1 (de) | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
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| US6159379A (en) | 1999-05-04 | 2000-12-12 | Baker Hughes Incorporated | Organic ammonium salts for the removal of water soluble organics in produced water |
| JP2001048786A (ja) | 1999-08-05 | 2001-02-20 | Yamanouchi Pharmaceut Co Ltd | 三環式ヘテロアリール誘導体 |
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