MX2009005440A - Procedimiento para la produccion de derivados de fenilalanina que tienen estructuras de base de quinazolinodiona e intermediarios para la produccion. - Google Patents
Procedimiento para la produccion de derivados de fenilalanina que tienen estructuras de base de quinazolinodiona e intermediarios para la produccion.Info
- Publication number
- MX2009005440A MX2009005440A MX2009005440A MX2009005440A MX2009005440A MX 2009005440 A MX2009005440 A MX 2009005440A MX 2009005440 A MX2009005440 A MX 2009005440A MX 2009005440 A MX2009005440 A MX 2009005440A MX 2009005440 A MX2009005440 A MX 2009005440A
- Authority
- MX
- Mexico
- Prior art keywords
- quinazolinedione
- production
- phenylalanine derivatives
- skeletons
- derivative
- Prior art date
Links
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical group C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 150000002993 phenylalanine derivatives Chemical class 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000003672 ureas Chemical class 0.000 abstract 2
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012304 carboxyl activating agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Un procedimiento para la producción de derivados de fenilalanina que tienen anillos de quinazolinediona como se representa por la fórmula general (1) o sales farmacéuticamente aceptables de los mismos: (ver fórmula (1)) que comprende los siguientes pasos (a), (b) y (c): el paso (a) de hacer reaccionar un derivado de acilfenilalalnina representado por la fórmula general (2): (ver fórmula (2)) con un agente introductor de carbonilo y un derivado específico de ácido antranílico para formar un derivado de urea asimétrico de carboxi; el paso (b) de convertir el derivado de urea asimétrico de carboxi en una quinazolinediona correspondiente en presencia de im agente activador de carboxi, y el paso opcional (c) que comprende el paso de N-alquilación de reemplazar el átomo de hidrógeno fijado al átomo de nitrógeno que constituye el anillo de quinazolinediona mediante un grupo alquilo con un agente de N-alquilación y/o el paso de desbloqueo de desbloquear R3'(un grupo que corresponde a R3) cuando R3' está en un estado protegido; de acuerdo con el procedimiento, se pueden producir derivados de fenilalanina que tengan estructuras de quinazolinediona con alto rendimiento favorable para su industrialización.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006315837 | 2006-11-22 | ||
| PCT/JP2007/072615 WO2008062859A1 (en) | 2006-11-22 | 2007-11-22 | Process for production of phenylalanine derivatives having quinazolinedione skeletons and intermediates for the production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2009005440A true MX2009005440A (es) | 2009-07-29 |
| MX297306B MX297306B (es) | 2012-03-22 |
Family
ID=39429788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2009005440A MX297306B (es) | 2006-11-22 | 2007-11-22 | Procedimiento para la produccion de derivados de fenilalanina que tienen estructuras de base de quinazolinodiona e intermediarios para la produccion. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8058432B2 (es) |
| EP (1) | EP2103601B1 (es) |
| JP (1) | JP5273587B2 (es) |
| CN (1) | CN101589028B (es) |
| AT (1) | ATE549321T1 (es) |
| AU (1) | AU2007322637B2 (es) |
| BR (1) | BRPI0718988A2 (es) |
| ES (1) | ES2380135T3 (es) |
| IL (1) | IL198902A (es) |
| MX (1) | MX297306B (es) |
| RU (1) | RU2469028C2 (es) |
| WO (1) | WO2008062859A1 (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2548419T3 (es) * | 2003-02-20 | 2015-10-16 | Ajinomoto Co., Inc. | Procedimiento para producir un derivado de fenilalanina que tiene esqueleto de quinazolindiona e intermedio para el mismo |
| WO2005051925A1 (ja) * | 2003-11-27 | 2005-06-09 | Ajinomoto Co., Inc. | フェニルアラニン誘導体の結晶及びその製造方法 |
| KR101194176B1 (ko) * | 2003-12-22 | 2012-10-24 | 아지노모토 가부시키가이샤 | 신규한 페닐알라닌 유도체 |
| EP2402326A1 (en) * | 2005-06-21 | 2012-01-04 | Ajinomoto Co., Inc. | Crystals of hydrochloride salts of a Phenylalanine Derivative, Production Method Thereof and Use Thereof as alpha4 integrin Inhibitors |
| MX297306B (es) | 2006-11-22 | 2012-03-22 | Ajinomoto Kk | Procedimiento para la produccion de derivados de fenilalanina que tienen estructuras de base de quinazolinodiona e intermediarios para la produccion. |
| EP2853529A1 (en) | 2010-03-29 | 2015-04-01 | Ajinomoto Co., Inc. | Crystals of salts of phenylalanine derivatives |
| DK2842945T3 (en) * | 2012-04-24 | 2017-01-30 | Ea Pharma Co Ltd | Sulfonamide derivative and medical use thereof |
| WO2014201172A1 (en) * | 2013-06-11 | 2014-12-18 | Receptos, Inc. | Novel glp-1 receptor modulators |
| WO2015048819A1 (en) | 2013-09-30 | 2015-04-02 | The Regents Of The University Of California | Anti-alphavbeta1 integrin compounds and methods |
| WO2016051828A1 (ja) | 2014-09-29 | 2016-04-07 | 味の素株式会社 | 潰瘍性大腸炎の治療用医薬組成物 |
| CA2981371A1 (en) | 2015-03-10 | 2016-09-15 | The Regents Of The University Of California | Anti-alphavbeta1 integrin inhibitors and methods of use |
| CN107382897B (zh) * | 2017-07-10 | 2021-05-04 | 浙江宏元药业股份有限公司 | 一种贝曲西班的中间体及其制备方法和应用 |
| CN110964001B (zh) * | 2018-09-29 | 2022-07-22 | 沈阳中化农药化工研发有限公司 | 一种甲基化制备含异恶唑啉脲嘧啶类化合物的方法 |
| US11174256B2 (en) | 2018-10-30 | 2021-11-16 | Gilead Sciences, Inc. | Imidazopyridine derivatives |
| HRP20250191T1 (hr) | 2018-10-30 | 2025-04-11 | Gilead Sciences, Inc. | Derivati 3-(kinolin-8-il)-1,4-dihidropirido[3,4-d]pirimidin-2,4-diona kao inhibitori alfa4beta7 integrina za liječenje upalnih bolesti |
| JP7189369B2 (ja) | 2018-10-30 | 2022-12-13 | ギリアード サイエンシーズ, インコーポレイテッド | アルファ4β7インテグリンの阻害のための化合物 |
| AU2019373242B2 (en) | 2018-10-30 | 2023-07-13 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| EP4013499A1 (en) | 2019-08-14 | 2022-06-22 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| CN116283803A (zh) * | 2022-12-05 | 2023-06-23 | 上海旭东海普药业有限公司 | 一种氟马西尼中间体的制备方法 |
| CN116655543B (zh) * | 2023-06-02 | 2025-06-27 | 北京康立生医药技术开发有限公司 | 一种溃疡性结肠炎治疗药物的制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4054591A (en) * | 1975-10-03 | 1977-10-18 | American Home Products Corporation | 2-Cyano-3-or 4-(substituted amino)oxanilic acid derivatives |
| CA1061356A (en) * | 1975-10-03 | 1979-08-28 | Dieter H. Klaubert | 2-cyano-3- or 4-(substituted amino) oxanilic acid derivatives |
| US4665070A (en) * | 1985-06-25 | 1987-05-12 | Syntex (U.S.A.) Inc. | 2-oxy-4H-3,1-benzoxazin-4-ones and pharmaceutical use |
| US5985872A (en) * | 1995-05-24 | 1999-11-16 | G.D. Searle & Co. | 2-amino-benzoxazinones for the treatment of viral infections |
| KR100460932B1 (ko) * | 1995-05-24 | 2005-02-28 | 지.디. 썰 엘엘씨 | 바이러스감염치료용2-아미노-벤조옥사진온 |
| AU2001262089A1 (en) * | 2000-03-14 | 2001-09-24 | Novartis Ag | Alpha4beta1 and alpha4beta7 integrin inhibitors |
| NZ524122A (en) * | 2000-08-18 | 2005-02-25 | Ajinomoto Kk | Phenylalanine derivatives useful as pharmaceutical agents |
| US20040129606A1 (en) * | 2003-01-07 | 2004-07-08 | Catalytic Distillation Technologies | HDS process using selected naphtha streams |
| ES2548419T3 (es) | 2003-02-20 | 2015-10-16 | Ajinomoto Co., Inc. | Procedimiento para producir un derivado de fenilalanina que tiene esqueleto de quinazolindiona e intermedio para el mismo |
| PL1663982T3 (pl) * | 2003-07-31 | 2008-03-31 | Sanofi Aventis | Pochodne aminochinoliny i ich zastosowanie jako ligandów adenozyny A3 |
| WO2005046696A1 (ja) | 2003-11-14 | 2005-05-26 | Ajinomoto Co., Inc. | フェニルアラニン誘導体の固体分散体または固体分散体医薬製剤 |
| EP3216449A1 (en) | 2003-11-14 | 2017-09-13 | EA Pharma Co., Ltd. | Oral administration preparation of phenylalanine derivatives |
| WO2005051925A1 (ja) | 2003-11-27 | 2005-06-09 | Ajinomoto Co., Inc. | フェニルアラニン誘導体の結晶及びその製造方法 |
| KR101194176B1 (ko) * | 2003-12-22 | 2012-10-24 | 아지노모토 가부시키가이샤 | 신규한 페닐알라닌 유도체 |
| JP3950870B2 (ja) * | 2004-05-14 | 2007-08-01 | 株式会社シマノ | 自転車用ブレーキ装置 |
| EP2402326A1 (en) | 2005-06-21 | 2012-01-04 | Ajinomoto Co., Inc. | Crystals of hydrochloride salts of a Phenylalanine Derivative, Production Method Thereof and Use Thereof as alpha4 integrin Inhibitors |
| WO2007038571A2 (en) * | 2005-09-26 | 2007-04-05 | Smithkline Beecham Corporation | Prolyl hydroxylase antagonists |
| EP2049490A1 (en) * | 2006-06-09 | 2009-04-22 | Astra Zeneca AB | N-(benzoyl)-o- [2- (pyridin- 2 -ylamino) ethyl]-l-tyrosine derivatives and related compounds as a5b1 antagonists for the treatment of solid tumors |
| MX297306B (es) | 2006-11-22 | 2012-03-22 | Ajinomoto Kk | Procedimiento para la produccion de derivados de fenilalanina que tienen estructuras de base de quinazolinodiona e intermediarios para la produccion. |
-
2007
- 2007-11-22 MX MX2009005440A patent/MX297306B/es active IP Right Grant
- 2007-11-22 WO PCT/JP2007/072615 patent/WO2008062859A1/ja not_active Ceased
- 2007-11-22 RU RU2009123440/04A patent/RU2469028C2/ru not_active IP Right Cessation
- 2007-11-22 JP JP2008545444A patent/JP5273587B2/ja active Active
- 2007-11-22 AT AT07832344T patent/ATE549321T1/de active
- 2007-11-22 ES ES07832344T patent/ES2380135T3/es active Active
- 2007-11-22 CN CN200780050294.7A patent/CN101589028B/zh active Active
- 2007-11-22 EP EP07832344A patent/EP2103601B1/en active Active
- 2007-11-22 AU AU2007322637A patent/AU2007322637B2/en not_active Ceased
- 2007-11-22 BR BRPI0718988-5A2A patent/BRPI0718988A2/pt not_active IP Right Cessation
-
2009
- 2009-05-21 IL IL198902A patent/IL198902A/en active IP Right Grant
- 2009-05-22 US US12/470,846 patent/US8058432B2/en not_active Expired - Fee Related
-
2011
- 2011-08-26 US US13/218,946 patent/US8546610B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20090318688A1 (en) | 2009-12-24 |
| IL198902A0 (en) | 2010-02-17 |
| US8546610B2 (en) | 2013-10-01 |
| US20110313154A1 (en) | 2011-12-22 |
| EP2103601B1 (en) | 2012-03-14 |
| AU2007322637A1 (en) | 2008-05-29 |
| BRPI0718988A2 (pt) | 2014-02-11 |
| EP2103601A1 (en) | 2009-09-23 |
| RU2009123440A (ru) | 2010-12-27 |
| CN101589028B (zh) | 2014-02-19 |
| RU2469028C2 (ru) | 2012-12-10 |
| JP5273587B2 (ja) | 2013-08-28 |
| IL198902A (en) | 2015-02-26 |
| US8058432B2 (en) | 2011-11-15 |
| MX297306B (es) | 2012-03-22 |
| CN101589028A (zh) | 2009-11-25 |
| EP2103601A4 (en) | 2010-07-07 |
| AU2007322637B2 (en) | 2012-07-05 |
| ATE549321T1 (de) | 2012-03-15 |
| JPWO2008062859A1 (ja) | 2010-03-04 |
| ES2380135T3 (es) | 2012-05-08 |
| WO2008062859A1 (en) | 2008-05-29 |
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