PL154625B1 - Method of obtaining l-alanyl-l-proline - Google Patents

Method of obtaining l-alanyl-l-proline

Info

Publication number: PL154625B1
Authority: PL; Poland
Prior art keywords: formula; proline; ethyl; alanyl; hydrogen
Prior art date: 1988-07-13

Application number

PL28052689A

Other languages

English (en)

Polish (pl)

Other versions

PL280526A1 (en

Inventor

Marjo Merslavic

Pavel Zupet

Vesna Flego

Miha Japelj

Branko Stanovnik

Janja Cirnski

Original Assignee

Krka Tovarna Zdravil

Priority date (The priority date 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 date listed.)

1988-07-13

Filing date

1989-07-11

Publication date

1991-08-30

1989-07-11 Application filed by Krka Tovarna Zdravil filed Critical Krka Tovarna Zdravil

1990-02-05 Publication of PL280526A1 publication Critical patent/PL280526A1/xx

1991-08-30 Publication of PL154625B1 publication Critical patent/PL154625B1/pl

Links

WPWUFUBLGADILS-WDSKDSINSA-N Ala-Pro Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O WPWUFUBLGADILS-WDSKDSINSA-N 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 12
108010087924 alanylproline Proteins 0.000 title abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
229910052739 hydrogen Chemical group 0.000 claims abstract description 7
239000001257 hydrogen Chemical group 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
229960002429 proline Drugs 0.000 claims abstract description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 3
239000003495 polar organic solvent Substances 0.000 claims abstract description 3
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 abstract 2
150000001875 compounds Chemical class 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract description 5
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 abstract description 3
239000011976 maleic acid Substances 0.000 abstract description 3
229930182821 L-proline Natural products 0.000 abstract description 2
239000002904 solvent Substances 0.000 abstract description 2
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
101800000734 Angiotensin-1 Proteins 0.000 description 3
102400000344 Angiotensin-1 Human genes 0.000 description 3
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
102000005862 Angiotensin II Human genes 0.000 description 2
101800000733 Angiotensin-2 Proteins 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 2
108090000783 Renin Proteins 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229960003767 alanine Drugs 0.000 description 2
229950006323 angiotensin ii Drugs 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
102000004881 Angiotensinogen Human genes 0.000 description 1
108090001067 Angiotensinogen Proteins 0.000 description 1
108010064733 Angiotensins Proteins 0.000 description 1
102000015427 Angiotensins Human genes 0.000 description 1
101100189068 Bacillus subtilis (strain 168) proI gene Proteins 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
102100028255 Renin Human genes 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
STPXIOGYOLJXMZ-UHFFFAOYSA-N ethyl 2-oxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CCC1=CC=CC=C1 STPXIOGYOLJXMZ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940037201 oris Drugs 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000008279 sol Substances 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1

Landscapes

Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)

PL28052689A 1988-07-13 1989-07-11 Method of obtaining l-alanyl-l-proline PL154625B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
YU135588A YU46919B (sh)	1988-07-13	1988-07-13	Postupak za dobijanje derivata l-alanil-l-prolina

Publications (2)

Publication Number	Publication Date
PL280526A1 PL280526A1 (en)	1990-02-05
PL154625B1 true PL154625B1 (en)	1991-08-30

Family

ID=25553829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL28052689A PL154625B1 (en)	1988-07-13	1989-07-11	Method of obtaining l-alanyl-l-proline

Country Status (10)

Country	Link
JP (1)	JP2714447B2 (de)
AT (1)	AT394726B (de)
DD (1)	DD284028B5 (de)
ES (1)	ES2015723A6 (de)
NO (1)	NO172894C (de)
PL (1)	PL154625B1 (de)
SI (1)	SI8811355A (de)
SU (1)	SU1757471A3 (de)
UA (1)	UA18634A1 (de)
YU (1)	YU46919B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5847135A (en) *	1994-06-17	1998-12-08	Vertex Pharmaceuticals, Incorporated	Inhibitors of interleukin-1β converting enzyme
AU2003272077A1 (en) *	2003-07-31	2005-02-14	Lupin Limited	Alpha-amino acid benzothiazolylthio ester as intermediates for manufacture of ace inhibitors and process for preparation thereof
CN101484411A (zh) *	2006-06-27	2009-07-15	桑多斯股份公司	盐的新制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4442089A (en) *	1982-07-06	1984-04-10	E. R. Squibb & Sons, Inc.	Method for treating glaucoma with topical or systemic ACE inhibitor compositions
JPS6248696A (ja) *	1985-08-27	1987-03-03	Kanegafuchi Chem Ind Co Ltd	Ｎ−〔１（ｓ）−エトキシカルボニル−３−フエニルプロピル〕−ｌ−アラニル−ｌ−プロリンの製造法

1988
- 1988-07-13 SI SI8811355A patent/SI8811355A/sl unknown
- 1988-07-13 YU YU135588A patent/YU46919B/sh unknown
1989
- 1989-07-07 NO NO892813A patent/NO172894C/no unknown
- 1989-07-10 ES ES8902425A patent/ES2015723A6/es not_active Expired - Lifetime
- 1989-07-11 AT AT168189A patent/AT394726B/de not_active IP Right Cessation
- 1989-07-11 PL PL28052689A patent/PL154625B1/pl unknown
- 1989-07-11 DD DD33068889A patent/DD284028B5/de active IP Right Maintenance
- 1989-07-12 UA UA4614532A patent/UA18634A1/uk unknown
- 1989-07-12 SU SU894614532A patent/SU1757471A3/ru active
- 1989-07-13 JP JP1179211A patent/JP2714447B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO892813D0 (no)	1989-07-07
UA18634A1 (uk)	1997-12-25
SU1757471A3 (ru)	1992-08-23
JPH0272195A (ja)	1990-03-12
NO172894B (no)	1993-06-14
PL280526A1 (en)	1990-02-05
NO892813L (no)	1990-01-15
SI8811355A (en)	1995-04-30
AT394726B (de)	1992-06-10
NO172894C (no)	1993-09-22
JP2714447B2 (ja)	1998-02-16
ATA168189A (de)	1991-11-15
YU135588A (en)	1990-02-28
ES2015723A6 (es)	1990-09-01
DD284028B5 (de)	1996-08-08
YU46919B (sh)	1994-06-24

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US5359086A (en)	1994-10-25	Process for preparing alkyl-L-alanyl-L-proline derivatives
EP0316218B1 (de)	1993-09-15	L-Prolin-Derivate, deren Herstellung und deren biologische Anwendungen
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KR890004365B1 (ko)	1989-10-31	디플루오로사이클로스타틴 함유 폴리펩티드 유도체의 제조방법
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JPWO1999045000A1 (ja)	2002-10-15	４−チアゾリルメチル誘導体の製造方法
KR100971347B1 (ko)	2010-07-20	씨형 간염바이러스 감염 치료용 엔에스3 프로테아제 억제제
SI9600169A (en)	1997-12-31	Process for preparation of compounds with ace inhibitory effect
JPH0560828B2 (de)	1993-09-03
JPS63275552A (ja)	1988-11-14	新規なアミノ酸誘導体
JPS61186397A (ja)	1986-08-20	レニン及び酸プロテアーゼを抑制するペプチド誘導体
JPS62120370A (ja)	1987-06-01	新規なアミノ酸誘導体
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