ES486572A1 - Procedimiento para la fabricacion de acidos treo-3-amino-2- hidroxibutanoil amonoaceticos. - Google Patents
Procedimiento para la fabricacion de acidos treo-3-amino-2- hidroxibutanoil amonoaceticos.Info
- Publication number
- ES486572A1 ES486572A1 ES486572A ES486572A ES486572A1 ES 486572 A1 ES486572 A1 ES 486572A1 ES 486572 A ES486572 A ES 486572A ES 486572 A ES486572 A ES 486572A ES 486572 A1 ES486572 A1 ES 486572A1
- Authority
- ES
- Spain
- Prior art keywords
- amino
- image
- general formula
- threo
- represented
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 150000002148 esters Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- MUQYXPVMHCCFJE-UHFFFAOYSA-N 2-amino-2-hydroxy-4-oxobutanoic acid Chemical compound OC(=O)C(O)(N)CC=O MUQYXPVMHCCFJE-UHFFFAOYSA-N 0.000 abstract 1
- QVPLPSZGHFSYEQ-UHFFFAOYSA-N 2-amino-2-hydroxybutanoic acid Chemical compound CCC(N)(O)C(O)=O QVPLPSZGHFSYEQ-UHFFFAOYSA-N 0.000 abstract 1
- QTRAXZHIRXYYPP-UHFFFAOYSA-N 3-amino-2-hydroxybutanoic acid Chemical compound CC(N)C(O)C(O)=O QTRAXZHIRXYYPP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003974 3-carbamimidamidopropyl group Chemical group C(N)(=N)NCCC* 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- -1 amino, hydroxy Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 238000005897 peptide coupling reaction Methods 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/54—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings 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
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
El ácido (2s, 3R)-3-amino-2-hidroxi-4- fenilibutanoil-aminoacético es una substancia poco tóxica aislada a partir de filtrados de cultivos de strptomices olivoreticuli como inhibidor de la aminopeptidasa B que se ha descubierto muestra un efecto creciente de inmunorrespuesta tal como hiperestesia deferida, mecanismo de activación de defensas en vivo y posee asimismo efectos inhibidores para el cáncer y dicho compuesto se espera tenga aplicaciones útiles como producto farmacéutico. También es sabido que varios ácidos 3-amino-2-hidroxibutanoil-aminoaceticos distintos de la bestatina, presentan una actividad inhibidora igual o mayor a la aminopeptidasa B que la misma bestatina
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14550978A JPS5572151A (en) | 1978-11-25 | 1978-11-25 | Threo-(2rs)-3-amino-2-hydroxy-4-oxo-4-phenylbutyric acid, its ester, and their preparation |
JP15315778A JPS5579353A (en) | 1978-12-13 | 1978-12-13 | Preparation of (2s,3r)-3-amino-2-hydroxy-4- phenylbutanoylaminoacetic acid and its intermediate |
Publications (1)
Publication Number | Publication Date |
---|---|
ES486572A1 true ES486572A1 (es) | 1980-09-16 |
Family
ID=26476602
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES486572A Expired ES486572A1 (es) | 1978-11-25 | 1979-11-22 | Procedimiento para la fabricacion de acidos treo-3-amino-2- hidroxibutanoil amonoaceticos. |
Country Status (13)
Country | Link |
---|---|
US (3) | US4281180A (es) |
AR (1) | AR227636A1 (es) |
AU (1) | AU530362B2 (es) |
CA (3) | CA1182125A (es) |
CH (3) | CH650265A5 (es) |
DE (2) | DE2954076C2 (es) |
DK (1) | DK162288C (es) |
ES (1) | ES486572A1 (es) |
FR (3) | FR2442227A1 (es) |
GB (2) | GB2090595B (es) |
IT (2) | IT1194593B (es) |
NL (2) | NL188162C (es) |
SE (3) | SE452888B (es) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4370318A (en) * | 1980-07-07 | 1983-01-25 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Bestatin-related compounds as immunopotentiator |
JPS5767516A (en) * | 1980-09-24 | 1982-04-24 | Microbial Chem Res Found | Novel analgesic agent |
GB2094786B (en) * | 1981-03-04 | 1985-09-11 | Ici Plc | Herbicidal and fungicidal amide derivatives |
JPS58110553A (ja) * | 1981-12-24 | 1983-07-01 | Microbial Chem Res Found | ベスタチンのγ型結晶及びその製造法 |
JPS606647A (ja) * | 1983-06-17 | 1985-01-14 | Microbial Chem Res Found | アルフアメニン及びその関連化合物と合成法 |
JPS62205095A (ja) * | 1986-03-04 | 1987-09-09 | Toyo Jozo Co Ltd | 新生理活性物質アルドスタチンおよびその製造法 |
US4681972A (en) * | 1986-09-16 | 1987-07-21 | Warner-Lambert Company | Separation of diastereomers |
US4871870A (en) * | 1987-03-16 | 1989-10-03 | Biomeasure, Inc. | Immunomodulators and method of making same |
IT1216104B (it) * | 1988-03-16 | 1990-02-22 | Zambon Spa | Peptidi ad attivita' farmaceutica. |
IT1217567B (it) * | 1988-05-11 | 1990-03-30 | Zambon Spa | Processo diastereoselettivo per la preparazione di intermedi utili per la sintesi di derivati peptidici |
JPH0759507B2 (ja) * | 1989-02-23 | 1995-06-28 | 日本化薬株式会社 | 骨髄異形成症候群治療剤 |
NL9101380A (nl) * | 1991-08-13 | 1993-03-01 | Dsm Nv | Werkwijze voor de bereiding van een alfa-aminozuur, de overeenkomstige ester en amide. |
US5455353A (en) * | 1993-03-24 | 1995-10-03 | Hoffmann-La Roche Inc. | 4-(benzyl-2-oxo-oxazolidin-5 ylmethyl)N tertbutyl-decahydroisoquinoline-3-carboxamides |
US5656603A (en) * | 1995-05-31 | 1997-08-12 | Loyola University Of Chicago | Aminopeptidase P inhibitors and uses thereof |
CA2312385A1 (en) * | 1999-06-22 | 2000-12-22 | Daiso Co., Ltd. | Process for producing erythro-3-amino-2-hydroxybutyric acid derivatives |
JP2005029470A (ja) * | 2001-06-21 | 2005-02-03 | Japan Energy Electronic Materials Inc | 新規ノルスタチン誘導体 |
UY32662A (es) * | 2009-05-28 | 2010-12-31 | Novartis Ag | Derivados amino-propionicos sustituidos como inhibidores de neprilisina |
WO2010136474A2 (en) | 2009-05-28 | 2010-12-02 | Novartis Ag | Substituted aminobutyric derivatives as neprilysin inhibitors |
JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
CN101891647B (zh) * | 2010-03-15 | 2012-12-19 | 浙江普洛康裕制药有限公司 | 一种乌苯美司的制备方法 |
MX2013006805A (es) * | 2010-12-15 | 2013-07-29 | Theravance Inc | Inhibidores de la neprilisina. |
CN102391145B (zh) * | 2011-08-31 | 2014-07-02 | 深圳万乐药业有限公司 | 一种乌苯美司中间体的光学异构体的拆分方法 |
EA026989B1 (ru) | 2013-02-14 | 2017-06-30 | Новартис Аг | Производные замещенной бисфенилбутановой кислоты в качестве ингибиторов nep с улучшенной in vivo эффективностью |
US9163040B2 (en) | 2013-02-14 | 2015-10-20 | Novartis Ag | Substituted bisphenyl butanoic phosphonic acid derivatives as NEP inhibitors |
CN103360277A (zh) * | 2013-04-01 | 2013-10-23 | 上海信谊万象药业股份有限公司 | 一种乌苯美司重结晶的方法 |
CN103333089A (zh) * | 2013-06-20 | 2013-10-02 | 深圳万乐药业有限公司 | N-[(2s,3r)-4-苯基-3-苄基-3-苄氧甲酰氨基-2-羟基丁酰]-l-亮氨酸苄酯的晶型及其制备方法 |
CN106117075B (zh) * | 2016-01-14 | 2020-06-12 | 上海信谊万象药业股份有限公司 | 一种新型乌苯美司重结晶方法 |
WO2018007919A1 (en) * | 2016-07-05 | 2018-01-11 | Novartis Ag | New process for early sacubitril intermediates |
CN106631880B (zh) * | 2016-08-01 | 2018-06-01 | 四川青木制药有限公司 | 一种乌苯美司δ晶型及其制备方法 |
CN106831473B (zh) * | 2017-02-22 | 2019-07-16 | 江西瑞雅药业有限公司 | 3-酰胺基-4-(2’-烷氧基-4-联苯基)丁酸衍生物及其制备方法、药物组合物 |
AU2022376563A1 (en) | 2021-11-01 | 2023-12-07 | Alkahest, Inc. | Benzodioxane modulators of leukotriene a4 hydrolase (lta4h) for prevention and treatment of aging-associated diseases |
CN115784918B (zh) * | 2022-11-24 | 2024-10-15 | 四川青木制药有限公司 | 一种高纯度乌苯美司中间体的制备方法 |
CN115594606A (zh) * | 2022-12-16 | 2023-01-13 | 成都傲科新技术有限责任公司(Cn) | 苏式-2-羟基-3-乙酰氨基-4-苯基羰基丁酸不对称合成方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2242086A1 (en) * | 1973-09-03 | 1975-03-28 | Aries Robert | Antibacterial, antiviral dihydroxy butyric acid derivs - active against Gram-positive and -negative cocci and bacilli |
US4179573A (en) * | 1974-07-01 | 1979-12-18 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid |
US4052449A (en) * | 1974-07-01 | 1977-10-04 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Biologically active substance, bestatin, and production thereof |
US4029547A (en) * | 1974-07-01 | 1977-06-14 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Biologically active substance, bestatin, and production thereof |
US4189604A (en) * | 1975-07-22 | 1980-02-19 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Bestatin |
GB1510477A (en) | 1975-07-22 | 1978-05-10 | Microbial Chem Res Found | Peptides and to amino acid intermediates thereof |
CH614928A5 (es) * | 1975-09-12 | 1979-12-28 | Nobel Hoechst Chimie | |
FR2351952A1 (fr) * | 1975-09-12 | 1977-12-16 | Nobel Hoechst Chimie | Procede de fabrication de derives n-acyles de glycines a substituees par des radicaux aromatiques |
JPS609487B2 (ja) * | 1976-03-26 | 1985-03-11 | 財団法人微生物化学研究会 | 免疫制癌剤 |
US4105789A (en) * | 1976-05-10 | 1978-08-08 | E. R. Squibb & Sons, Inc. | Carboxyalkylacylamino acids |
GB1540019A (en) * | 1977-06-01 | 1979-02-07 | Microbial Chem Res Found | Bestatin derivatives |
FR2393788A2 (fr) * | 1977-06-10 | 1979-01-05 | Microbial Chem Res Found | Derives de bestatine |
JPS6026099B2 (ja) * | 1977-09-21 | 1985-06-21 | 財団法人微生物化学研究会 | ペプチド、その酸附加塩およびその製造法 |
US4243678A (en) * | 1977-12-30 | 1981-01-06 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Acylhydrocarbylaminoalkanoic acids, compositions and uses |
-
1979
- 1979-11-22 CH CH10433/79A patent/CH650265A5/de not_active IP Right Cessation
- 1979-11-22 NL NLAANVRAGE7908510,A patent/NL188162C/xx not_active IP Right Cessation
- 1979-11-22 AU AU53115/79A patent/AU530362B2/en not_active Ceased
- 1979-11-22 GB GB8200496A patent/GB2090595B/en not_active Expired
- 1979-11-22 DK DK496379A patent/DK162288C/da active
- 1979-11-22 SE SE7909655A patent/SE452888B/sv not_active IP Right Cessation
- 1979-11-22 DE DE2954076A patent/DE2954076C2/de not_active Expired
- 1979-11-22 DE DE19792947140 patent/DE2947140A1/de active Granted
- 1979-11-22 AR AR278992A patent/AR227636A1/es active
- 1979-11-22 GB GB7940413A patent/GB2037754B/en not_active Expired
- 1979-11-22 CA CA000340428A patent/CA1182125A/en not_active Expired
- 1979-11-22 CH CH6192/83A patent/CH653669A5/de not_active IP Right Cessation
- 1979-11-22 FR FR7928830A patent/FR2442227A1/fr active Granted
- 1979-11-22 IT IT27487/79A patent/IT1194593B/it active
- 1979-11-22 CH CH5649/81A patent/CH653687A5/de not_active IP Right Cessation
- 1979-11-22 ES ES486572A patent/ES486572A1/es not_active Expired
- 1979-11-23 US US06/096,693 patent/US4281180A/en not_active Expired - Lifetime
-
1980
- 1980-05-12 FR FR8010563A patent/FR2449078A1/fr active Granted
- 1980-11-28 US US06/211,035 patent/US4391986A/en not_active Expired - Lifetime
-
1981
- 1981-07-10 FR FR8113611A patent/FR2483409B1/fr not_active Expired
- 1981-10-06 NL NL8104545A patent/NL8104545A/nl not_active Application Discontinuation
- 1981-10-14 SE SE8106084A patent/SE453748B/sv not_active IP Right Cessation
- 1981-12-15 IT IT8125614A patent/IT1211147B/it active
- 1981-12-31 US US06/336,492 patent/US4453003A/en not_active Expired - Lifetime
-
1982
- 1982-06-14 CA CA000405157A patent/CA1170667A/en not_active Expired
- 1982-08-24 CA CA000410051A patent/CA1167464A/en not_active Expired
-
1984
- 1984-07-31 SE SE8403931A patent/SE466200B/sv not_active IP Right Cessation
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FD1A | Patent lapsed |
Effective date: 19970519 |