SI9720039B - Postopek za pripravo 1-alkoksikarbonil-3-fenil-propilnega derivata - Google Patents
Postopek za pripravo 1-alkoksikarbonil-3-fenil-propilnega derivata Download PDFInfo
- Publication number
- SI9720039B SI9720039B SI9720039A SI9720039A SI9720039B SI 9720039 B SI9720039 B SI 9720039B SI 9720039 A SI9720039 A SI 9720039A SI 9720039 A SI9720039 A SI 9720039A SI 9720039 B SI9720039 B SI 9720039B
- Authority
- SI
- Slovenia
- Prior art keywords
- process according
- phenylpropyl
- alkoxycarbonyl
- derivative
- formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 21
- 238000002360 preparation method Methods 0.000 title claims 3
- 239000002253 acid Substances 0.000 claims abstract 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000002904 solvent Substances 0.000 claims abstract 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims 7
- CEIWXEQZZZHLDM-AAEUAGOBSA-N (2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoic acid Chemical compound CCOC(=O)[C@@H](N[C@@H](C)C(O)=O)CCC1=CC=CC=C1 CEIWXEQZZZHLDM-AAEUAGOBSA-N 0.000 claims 3
- -1 1-carboxyl-3-phenylpropyl Chemical class 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- CEIWXEQZZZHLDM-WCQYABFASA-N (2s)-2-[[(2r)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azaniumyl]propanoate Chemical compound CCOC(=O)[C@H]([NH2+][C@@H](C)C([O-])=O)CCC1=CC=CC=C1 CEIWXEQZZZHLDM-WCQYABFASA-N 0.000 claims 2
- 238000006845 Michael addition reaction Methods 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 229960003767 alanine Drugs 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000007810 chemical reaction solvent Substances 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000006722 reduction reaction Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or 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
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
-
- 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
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- 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
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
-
- 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
-
- 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)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Claims (19)
1 PATENTNI ZAHTEVKI 1. Postopek za pripravo l-alkoksikarbonil-3-fenilpropilnega derivata s formulo (II)
ch2-ch2-ch-x-yI COOR (II) kjer je R alkilna skupina, X je -Ala-, -Gly-, -Leu-, -Ile-, -Val-, -Om-, Lys- ali -Hly-, kjer so co-amino skupine od -Om-, -Lys- in -Hly- zaščitene z acilno zaščitno skupino, Y je hidroksilna skupina, označen s tem, da katalitsko reduciramo 1-alkoksi-karbonil-3-okso-3-fenilpropilni derivat s formulo (I) c-ch2-ch-x-y 0 COOR ( I ) kjer so R, X in Y enaki, kot je definirano zgoraj, pri čemer zgoraj omenjeno katalitsko redukcijo izvedemo v alkoholu ali topilu, ki vsebuje alkohol, v prisotnosti močne kisline s koncentracijo od 0,4 do 5 N, pri čemer je količina močne kisline vsaj 3 ekvivalente na osnovi 1 ekvivalenta l-alkoksikarbonil-3-okso-3-fenilpropilnega derivata (1 mol), da kontroliramo nastanek l-alkoksikarbonil-3-cikloheksilpropilnega derivata s formulo (III) C H2 — C H2
CH —X — YI COOR kjer so R, X in Y enaki, kot je definirano zgoraj. (III) 2
2. Postopek po zahtevku 1, označen s tem, da obsega ločenje l-alkoksikarbonil-3-fenilpropilnega derivata s formulo (II) iz reakcijske raztopine, dobljene s katalitsko redukcijo, pri čemer l-karboksil-3-fenilpropilni derivat s formulo (IV)
COOH (IV) kjer sta X in Y enaka, kot je definirano zgoraj, kot stranski produkt odstranimo.
3. Postopek po zahtevku 2, označen s tem, da močno kislino nevtraliziramo na pH 4,6±1,5.
4. Postopek po zahtevku 1, 2 ali 3, označen s tem, daje X -L-Ala-.
5. Postopek po zahtevku 1, 2 ali 3, označen s tem, da je X -L-Lys-, katerega ω-amino skupina je zaščitena z acilno zaščitno skupino.
6. Postopek po zahtevku 2, označen s tem, da ločenje l-alkoksikarbonil-3-fenilpropilnega derivata s formulo (II) izvedemo s kristalizacijo iz vodne raztopine.
7. Postopek po zahtevku 6, označen s tem, da kristalizacijo izvedemo pri temperaturi ne manj kot 30 °C.
8. Postopek po zahtevku 1, 2 ali 3, označen s tem, da za katalitsko redukcijo uporabimo Michaelovo adicijsko reakcijsko zmes, ki vsebuje l-alkoksikarbonil-3-okso-3-fenilpropilni derivat s formulo (I), dobljen z Michaelovo adicijsko reakcijo β-benzoil akrilata in amino kisline ali njenega derivata. 3
9. Postopek po zahtevku 1, 2 ali 3, označen s tem, da kot reakcijsko topilo uporabimo alkohol, katerega vsebnost vode je največ 50 % (m/m).
10. Postopek po zahtevku 9, označen s tem, da kot reakcijsko topilo uporabimo alkohol, katerega vsebnost vode je v območju od 2 do 30 % (m/m).
11. Postopek po zahtevku 1, 2 ali 3, označen s tem, da kot močno kislino uporabimo žveplovo kislino.
12. Postopek po zahtevku 1, 2 ali 3, označen s tem, da močno kislino uporabimo v koncentraciji v območju od 3 do 15 ekvivalentov na osnovi 1 mola 1-alkoksikarbonil-3-okso-3-fenilpropilnega derivata s formulo (I) kot 1 ekvivalenta.
13. Postopek po zahtevku 1, 2 ali 3, označen s tem, da kot redukcijski katalizator uporabimo paladij ev katalizator.
14. Postopek po zahtevku 13, označen s tem, da kot redukcijski katalizator uporabimo Pd-C, Pd-glinico ali Pd-zeolit.
15. Postopek po zahtevku 1, 2 ali 3, označen s tem, da je reakcijska temperatura katalitske redukcije v območju od 10° do 35 °C.
16. Postopek po zahtevku 1, 2 ali 3, označen s tem, da je tlak vodika pri katalitski redukciji v območju od atmosferskega tlaka do 2 kg/cm2G.
17. Postopek po zahtevku 1, 2 ali 3, označen s tem, da katalitsko redukcijsko reakcijo ustavimo, preden izgine intermediat s formulo 4 4
ch-ch2-ch-x-y I I OH C O OR kjer je R alkilna skupina, X je -Ala-, -Gly-, -Leu-, -Ile-, -Val-, -Om-, Lys- ali -Hly-, kjer so ω-amino skupine od -Om-, -Lys- in -Hly- zaščitene z acilno zaščitno skupino in je Y hidroksilna skupina.
18. Postopek za pripravo N-(l(S)-etoksikarbonil-3-fenilpropil)-L-alanina, označen s tem, da kristaliziramo N-(l(S)-etoksikarbonil-3-fenilpropil)-L-alanin v prisotnosti vsaj enega izmed N-(l-karboksi-3-fenilpropil)-L-alanina in N-(l(R)-etoksikarbonil-3-fenilpropil)-L-alanina v vodni raztopini, da dobimo N-(l(S)-etoksikarbonil-3-fenilpropil)-L-alanin ter da odstranimo N-(l-karboksi-3-fenilpropil)-L-alanin in (N-(1 (R)-etoksikarbonil-3-fenilpropil)-L-alanin.
19. Postopek po zahtevku 18, označen s tem, da je vrednost pH vodne raztopine 4,6±1,5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11654596A JP3792777B2 (ja) | 1996-05-10 | 1996-05-10 | １−アルコキシカルボニル−３−フェニルプロピル誘導体の製造方法 |
| PCT/JP1997/001543 WO1997043246A1 (en) | 1996-05-10 | 1997-05-08 | Process for the preparation of 1-alkoxycarbonyl-3-phenylpropyl derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9720039A SI9720039A (sl) | 1999-08-31 |
| SI9720039B true SI9720039B (sl) | 2002-02-28 |
Family
ID=14689775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9720039A SI9720039B (sl) | 1996-05-10 | 1997-05-08 | Postopek za pripravo 1-alkoksikarbonil-3-fenil-propilnega derivata |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6118010A (sl) |
| EP (2) | EP1679303B1 (sl) |
| JP (1) | JP3792777B2 (sl) |
| KR (1) | KR100382633B1 (sl) |
| CN (1) | CN1159286C (sl) |
| AT (1) | ATE481378T1 (sl) |
| CA (1) | CA2254972C (sl) |
| DE (2) | DE69735667T2 (sl) |
| ES (2) | ES2257775T3 (sl) |
| HU (1) | HU227430B1 (sl) |
| IN (2) | IN183558B (sl) |
| SI (1) | SI9720039B (sl) |
| WO (1) | WO1997043246A1 (sl) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69934084T2 (de) * | 1998-09-22 | 2007-04-05 | Kaneka Corp. | Verfahren zur herstellung von n2-(1(s)-carboxy-3-phenylpropyl)-l-lysyl-l-prolin |
| AU2000239828A1 (en) * | 2000-04-18 | 2001-10-30 | Scinopharm Singapore Pte Ltd | Process for preparation of 3-((1'-(alkoxycarbonyl)-3'-phenylpropyl)amino)-2-oxo-(1)- benzazepine and its derivatives |
| AR033048A1 (es) | 2001-03-19 | 2003-12-03 | Kaneka Corp | Metodo para la purificacion de la n-(1(s)-etoxicarbonil-3-fenilpropil) -l-alanina |
| JP2003026644A (ja) * | 2001-07-11 | 2003-01-29 | Kanegafuchi Chem Ind Co Ltd | Ｎ２−（１（ｓ）−エトキシカルボニル−３−フェニルプロピル）−ｎ６−トリフルオロアセチル−ｌ−リジンの精製方法 |
| SI21101A (sl) * | 2001-11-26 | 2003-06-30 | LEK farmacevtska dru�ba d.d. | Koncentriranje vodnih frakcij lisinoprila z reverzno osmozo |
| US20070093664A1 (en) * | 2002-06-19 | 2007-04-26 | Tuncer Aslan | Process for the production of lisinopril |
| JP4744979B2 (ja) * | 2005-08-24 | 2011-08-10 | 独立行政法人理化学研究所 | ゼオライトを用いたタンパク質結晶化方法 |
| CA2677045C (en) | 2007-01-31 | 2016-10-18 | Dana-Farber Cancer Institute, Inc. | Stabilized p53 peptides and uses thereof |
| AU2008232709C1 (en) | 2007-03-28 | 2015-01-15 | President And Fellows Of Harvard College | Stitched polypeptides |
| CN101239923B (zh) * | 2007-12-31 | 2010-09-15 | 浙江工业大学 | (s,s)n-(1-乙氧羰基-3-苯丙基)-l-氨基酸衍生物的制备方法与精制方法 |
| SI2603600T1 (sl) | 2010-08-13 | 2019-04-30 | Aileron Therapeutics, Inc. | Peptidomimetični makrocikli |
| CN101973904B (zh) * | 2010-09-28 | 2014-01-01 | 雅本化学股份有限公司 | 一种具有高光学纯度的n2-[1-(s)-乙氧羰基-3-苯丙基]-n6-三氟乙酰基-l-赖氨酸的制备方法 |
| TWI643868B (zh) | 2011-10-18 | 2018-12-11 | 艾利倫治療公司 | 擬肽巨環化合物 |
| US8987414B2 (en) | 2012-02-15 | 2015-03-24 | Aileron Therapeutics, Inc. | Triazole-crosslinked and thioether-crosslinked peptidomimetic macrocycles |
| KR102112373B1 (ko) | 2012-02-15 | 2020-05-18 | 에일러론 테라퓨틱스 인코포레이티드 | 펩티드모방체 마크로사이클 |
| AU2013337388B2 (en) * | 2012-11-01 | 2018-08-02 | Aileron Therapeutics, Inc. | Disubstituted amino acids and methods of preparation and use thereof |
| CN105294827A (zh) * | 2014-07-21 | 2016-02-03 | 常州制药厂有限公司 | 一种马来酸依那普利的制备方法 |
| WO2016049359A1 (en) | 2014-09-24 | 2016-03-31 | Aileron Therapeutics, Inc. | Peptidomimetic macrocycles and uses thereof |
| AU2015320545C1 (en) | 2014-09-24 | 2020-05-14 | Aileron Therapeutics, Inc. | Peptidomimetic macrocycles and formulations thereof |
| MX2017011834A (es) | 2015-03-20 | 2018-04-11 | Aileron Therapeutics Inc | Macrociclos peptidomimeticos y usos de los mismos. |
| CN106220545B (zh) * | 2016-07-21 | 2019-08-13 | 成都摩尔生物医药有限公司 | 一种acei药物环己基杂质的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1327787A3 (ru) * | 1981-11-05 | 1987-07-30 | Хехст Аг (Фирма) | Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей |
| DE3246503A1 (de) * | 1982-12-16 | 1984-06-20 | Hoechst Ag, 6230 Frankfurt | Derivate der cis, endo-2-azabicyclo-(5.3.0)-decan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung |
| DE3660868D1 (en) * | 1985-02-04 | 1988-11-10 | Kanegafuchi Chemical Ind | Process for preparing ethyl-alpha-(1-carboxyethyl)-amino-gamma-oxo-gamma-phenylbutyrate |
| JPH01104034A (ja) * | 1986-03-27 | 1989-04-21 | Kanegafuchi Chem Ind Co Ltd | Ｎ↑２−（１−カルボキシ−３−フエニルプロピル）−ｌ−リジン誘導体の製造法 |
| DE3770301D1 (de) * | 1986-03-27 | 1991-07-04 | Kanegafuchi Chemical Ind | N2-(1-carboxy-3-oxo-3-phenylpropyl)-l-lysinverbindungen und deren abkoemmlinge. |
| JPS62239062A (ja) * | 1986-04-11 | 1987-10-19 | Matsushita Electric Ind Co Ltd | 交差コイル式メ−タの駆動回路 |
| JPH03115254A (ja) * | 1990-09-12 | 1991-05-16 | Kanegafuchi Chem Ind Co Ltd | α―（１―カルボキシエチル）アミノ―γ―フエニル酪酸エチルの製造法 |
| JPH06336495A (ja) * | 1993-05-28 | 1994-12-06 | Kyowa Hakko Kogyo Co Ltd | Ｌ−アラニル−ｌ−プロリン誘導体の製造法 |
-
1996
- 1996-05-10 JP JP11654596A patent/JP3792777B2/ja not_active Expired - Fee Related
-
1997
- 1997-05-08 HU HU9903214A patent/HU227430B1/hu not_active IP Right Cessation
- 1997-05-08 US US09/147,255 patent/US6118010A/en not_active Expired - Lifetime
- 1997-05-08 SI SI9720039A patent/SI9720039B/sl not_active IP Right Cessation
- 1997-05-08 AT AT06005434T patent/ATE481378T1/de not_active IP Right Cessation
- 1997-05-08 DE DE69735667T patent/DE69735667T2/de not_active Expired - Lifetime
- 1997-05-08 EP EP06005434A patent/EP1679303B1/en not_active Expired - Lifetime
- 1997-05-08 ES ES97918383T patent/ES2257775T3/es not_active Expired - Lifetime
- 1997-05-08 CN CNB971945292A patent/CN1159286C/zh not_active Expired - Lifetime
- 1997-05-08 WO PCT/JP1997/001543 patent/WO1997043246A1/ja active IP Right Grant
- 1997-05-08 EP EP97918383A patent/EP0903337B1/en not_active Expired - Lifetime
- 1997-05-08 KR KR10-1998-0708981A patent/KR100382633B1/ko not_active IP Right Cessation
- 1997-05-08 CA CA002254972A patent/CA2254972C/en not_active Expired - Fee Related
- 1997-05-08 ES ES06005434T patent/ES2353151T3/es not_active Expired - Lifetime
- 1997-05-08 DE DE69739998T patent/DE69739998D1/de not_active Expired - Lifetime
- 1997-05-09 IN IN838CA1997 patent/IN183558B/en unknown
-
1998
- 1998-09-24 IN IN1723CA1998 patent/IN187140B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0903337A1 (en) | 1999-03-24 |
| HU227430B1 (hu) | 2011-06-28 |
| CN1218454A (zh) | 1999-06-02 |
| ATE481378T1 (de) | 2010-10-15 |
| DE69735667T2 (de) | 2007-04-26 |
| DE69739998D1 (de) | 2010-10-28 |
| WO1997043246A1 (en) | 1997-11-20 |
| DE69735667D1 (de) | 2006-05-24 |
| CN1159286C (zh) | 2004-07-28 |
| JPH09301938A (ja) | 1997-11-25 |
| CA2254972A1 (en) | 1997-11-20 |
| EP0903337B1 (en) | 2006-04-12 |
| HUP9903214A3 (en) | 2002-12-28 |
| CA2254972C (en) | 2005-08-02 |
| IN183558B (sl) | 2000-02-12 |
| US6118010A (en) | 2000-09-12 |
| JP3792777B2 (ja) | 2006-07-05 |
| EP1679303B1 (en) | 2010-09-15 |
| ES2257775T3 (es) | 2006-08-01 |
| ES2353151T3 (es) | 2011-02-25 |
| SI9720039A (sl) | 1999-08-31 |
| EP1679303A1 (en) | 2006-07-12 |
| KR20000010840A (ko) | 2000-02-25 |
| EP0903337A4 (en) | 2001-02-28 |
| IN187140B (sl) | 2002-02-09 |
| KR100382633B1 (ko) | 2003-07-12 |
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Effective date: 20160112 |