SI8811355A - Process for preparing of L-alanine-L-proline derivatives - Google Patents

Process for preparing of L-alanine-L-proline derivatives Download PDF

Info

Publication number: SI8811355A
Authority: SI; Slovenia
Prior art keywords: formula; proline; ethyl; hydrogen; ethoxycarbonyl
Prior art date: 1988-07-13

Application number

SI8811355A

Other languages

English (en)

Slovenian (sl)

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

1988-07-13

Publication date

1995-04-30

1988-07-13 Application filed by Krka Tovarna Zdravil filed Critical Krka Tovarna Zdravil

1995-04-30 Publication of SI8811355A publication Critical patent/SI8811355A/sl

Links

238000004519 manufacturing process Methods 0.000 title 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 20
229960002429 proline Drugs 0.000 claims abstract description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
229910052739 hydrogen Chemical group 0.000 claims abstract description 11
239000001257 hydrogen Chemical group 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 10
WPWUFUBLGADILS-WDSKDSINSA-N Ala-Pro Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O WPWUFUBLGADILS-WDSKDSINSA-N 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 5
239000003495 polar organic solvent Substances 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 10
-1 (S) -ethoxycarbonyl-3-phenylpropyl Chemical group 0.000 claims description 8
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000003412 L-alanyl group Chemical class [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 2
SYZWSSNHPZXGML-UHFFFAOYSA-N dichloromethane;oxolane Chemical compound ClCCl.C1CCOC1 SYZWSSNHPZXGML-UHFFFAOYSA-N 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 21
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract description 4
108010087924 alanylproline Proteins 0.000 abstract description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract description 4
229930182821 L-proline Natural products 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
239000002904 solvent Substances 0.000 abstract description 2
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 2
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 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
229960003767 alanine Drugs 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 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
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 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
CUKWUWBLQQDQAC-VEQWQPCFSA-N (3s)-3-amino-4-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s,3s)-1-[[(2s)-1-[(2s)-2-[[(1s)-1-carboxyethyl]carbamoyl]pyrrolidin-1-yl]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-ox 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](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 CUKWUWBLQQDQAC-VEQWQPCFSA-N 0.000 description 2
102000005862 Angiotensin II Human genes 0.000 description 2
101800000733 Angiotensin-2 Proteins 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical class C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
229950006323 angiotensin ii Drugs 0.000 description 2
108010058865 angiotensinase Proteins 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000005051 trimethylchlorosilane Substances 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
102000004881 Angiotensinogen Human genes 0.000 description 1
108090001067 Angiotensinogen Proteins 0.000 description 1
102000004506 Blood Proteins Human genes 0.000 description 1
108010017384 Blood Proteins Proteins 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
150000008534 L-alanines Chemical class 0.000 description 1
125000000174 L-prolyl group Chemical class [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
LZFZMUMEGBBDTC-QEJZJMRPSA-N enalaprilat (anhydrous) Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 LZFZMUMEGBBDTC-QEJZJMRPSA-N 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
238000005984 hydrogenation reaction Methods 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension 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)

SI8811355A 1988-07-13 1988-07-13 Process for preparing of L-alanine-L-proline derivatives SI8811355A (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 (1)

Publication Number	Publication Date
SI8811355A true SI8811355A (en)	1995-04-30

Family

ID=25553829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI8811355A SI8811355A (en)	1988-07-13	1988-07-13	Process for preparing of L-alanine-L-proline derivatives

Country Status (10)

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

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
CA2655061A1 (en) *	2006-06-27	2008-01-03	Sandoz Ag	New method for salt preparation

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
DD284028B5 (de)	1996-08-08
SU1757471A3 (ru)	1992-08-23
PL154625B1 (en)	1991-08-30
NO172894C (no)	1993-09-22
YU46919B (sh)	1994-06-24
NO892813L (no)	1990-01-15
AT394726B (de)	1992-06-10
ATA168189A (de)	1991-11-15
JPH0272195A (ja)	1990-03-12
NO172894B (no)	1993-06-14
YU135588A (en)	1990-02-28
JP2714447B2 (ja)	1998-02-16
PL280526A1 (en)	1990-02-05
UA18634A1 (uk)	1997-12-25
ES2015723A6 (es)	1990-09-01

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Legal Events

Date	Code	Title	Description
2005-01-10	IF	Valid on the prs date