SE452888B - Sett att framstella treo-3-amino-2-hydroxibutanoylaminoettiksyror - Google Patents
Sett att framstella treo-3-amino-2-hydroxibutanoylaminoettiksyrorInfo
- Publication number
- SE452888B SE452888B SE7909655A SE7909655A SE452888B SE 452888 B SE452888 B SE 452888B SE 7909655 A SE7909655 A SE 7909655A SE 7909655 A SE7909655 A SE 7909655A SE 452888 B SE452888 B SE 452888B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- threo
- acid
- amino
- general formula
- Prior art date
Links
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- 150000007513 acids Chemical class 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 77
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- 238000000034 method Methods 0.000 claims description 30
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- 239000001257 hydrogen Substances 0.000 claims description 27
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 claims description 5
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- QVPLPSZGHFSYEQ-UHFFFAOYSA-N 2-amino-2-hydroxybutanoic acid Chemical compound CCC(N)(O)C(O)=O QVPLPSZGHFSYEQ-UHFFFAOYSA-N 0.000 claims description 2
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 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 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- GLUJNGJDHCTUJY-UHFFFAOYSA-N beta-leucine Chemical compound CC(C)C(N)CC(O)=O GLUJNGJDHCTUJY-UHFFFAOYSA-N 0.000 claims 1
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- OBKXEAXTFZPCHS-UHFFFAOYSA-N gamma-phenylbutyric acid Natural products OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 claims 1
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- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 8
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- ODIKTWMCZYPCKQ-UHFFFAOYSA-N tert-butyl n-phenacylcarbamate Chemical compound CC(C)(C)OC(=O)NCC(=O)C1=CC=CC=C1 ODIKTWMCZYPCKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| SE7909655L SE7909655L (sv) | 1980-05-26 |
| SE452888B true SE452888B (sv) | 1987-12-21 |
Family
ID=26476602
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7909655A SE452888B (sv) | 1978-11-25 | 1979-11-22 | Sett att framstella treo-3-amino-2-hydroxibutanoylaminoettiksyror |
| SE8106084A SE453748B (sv) | 1978-11-25 | 1981-10-14 | (2s,3r)-3-amino-2-hydroxi-4-(4-metoxifenyl)-butanoyl-(s)-leucin |
| SE8403931A SE466200B (sv) | 1978-11-25 | 1984-07-31 | Treo-3-skyddad amino-2-hydroxi-4-oxosmoersyra eller dess ester samt ett saett foer framstaellning daerav |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8106084A SE453748B (sv) | 1978-11-25 | 1981-10-14 | (2s,3r)-3-amino-2-hydroxi-4-(4-metoxifenyl)-butanoyl-(s)-leucin |
| SE8403931A SE466200B (sv) | 1978-11-25 | 1984-07-31 | Treo-3-skyddad amino-2-hydroxi-4-oxosmoersyra eller dess ester samt ett saett foer framstaellning daerav |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US4281180A (ko) |
| AR (1) | AR227636A1 (ko) |
| AU (1) | AU530362B2 (ko) |
| CA (3) | CA1182125A (ko) |
| CH (3) | CH653687A5 (ko) |
| DE (2) | DE2954076C2 (ko) |
| DK (1) | DK162288C (ko) |
| ES (1) | ES486572A1 (ko) |
| FR (3) | FR2442227A1 (ko) |
| GB (2) | GB2037754B (ko) |
| IT (2) | IT1194593B (ko) |
| NL (2) | NL188162C (ko) |
| SE (3) | SE452888B (ko) |
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 |
| DE3276110D1 (en) * | 1981-03-04 | 1987-05-27 | Ici Plc | Amide derivatives, processes for preparing them, their use as fungicides and pesticidal compositions containing them |
| 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 |
| BRPI1011657A2 (pt) * | 2009-05-28 | 2019-04-16 | Novartis Ag | derivados aminopropiônicos substituídos como inibidores de neprilisina |
| EA201101672A1 (ru) | 2009-05-28 | 2012-06-29 | Новартис Аг | Замещенные производные аминомасляной кислоты в качестве ингибиторов неприлизина |
| 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 |
| ES2550324T3 (es) * | 2010-12-15 | 2015-11-06 | Theravance Biopharma R&D Ip, Llc | Inhibidores de 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 |
| CN105008337B (zh) | 2013-02-14 | 2017-08-04 | 诺华股份有限公司 | 具有改善的体内功效的作为nep抑制剂的取代的联苯基丁酸衍生物 |
| LT2956464T (lt) | 2013-02-14 | 2018-07-10 | Novartis Ag | Pakeisti bisfenilbutanoinės fosfonrūgšties dariniai, kaip nep (neutralios endopeptidazės) inhibitoriai |
| 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 |
| JP6944473B2 (ja) * | 2016-07-05 | 2021-10-06 | ノバルティス アーゲー | 初期サクビトリル中間体のための新規な方法 |
| 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 |
| CN115784918A (zh) * | 2022-11-24 | 2023-03-14 | 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 |
| US4029547A (en) * | 1974-07-01 | 1977-06-14 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Biologically active substance, bestatin, and production thereof |
| 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 |
| 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 |
| 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 |
| CA1066304A (en) * | 1975-09-12 | 1979-11-13 | Yani Christidis | Process for manufacturing n-acyl derivatives of hydroxyarylgycines and novel products resulting therefrom |
| 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 ES ES486572A patent/ES486572A1/es not_active Expired
- 1979-11-22 DE DE2954076A patent/DE2954076C2/de not_active Expired
- 1979-11-22 CH CH5649/81A patent/CH653687A5/de not_active IP Right Cessation
- 1979-11-22 CH CH10433/79A patent/CH650265A5/de not_active IP Right Cessation
- 1979-11-22 DE DE19792947140 patent/DE2947140A1/de active Granted
- 1979-11-22 NL NLAANVRAGE7908510,A patent/NL188162C/xx not_active IP Right Cessation
- 1979-11-22 IT IT27487/79A patent/IT1194593B/it 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 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 CH CH6192/83A patent/CH653669A5/de not_active IP Right Cessation
- 1979-11-22 FR FR7928830A patent/FR2442227A1/fr active Granted
- 1979-11-22 AU AU53115/79A patent/AU530362B2/en not_active Ceased
- 1979-11-22 AR AR278992A patent/AR227636A1/es active
- 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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