DK172005B1 - Fremgangsmåde til syntese af alpha-N-alkylerede aminosyrer og estere deraf - Google Patents
Fremgangsmåde til syntese af alpha-N-alkylerede aminosyrer og estere deraf Download PDFInfo
- Publication number
- DK172005B1 DK172005B1 DK515088A DK515088A DK172005B1 DK 172005 B1 DK172005 B1 DK 172005B1 DK 515088 A DK515088 A DK 515088A DK 515088 A DK515088 A DK 515088A DK 172005 B1 DK172005 B1 DK 172005B1
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- carbon atoms
- derivative
- synthesis
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 15
- 150000001413 amino acids Chemical class 0.000 title description 4
- 150000002148 esters Chemical class 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 239000007858 starting material Substances 0.000 claims abstract description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 108010016626 Dipeptides Proteins 0.000 abstract description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract description 2
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- -1 AcOC2H5 Chemical compound 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- AUVAVXHAOCLQBF-YUMQZZPRSA-N (2s)-2-[[(2s)-1-ethoxy-1-oxopentan-2-yl]azaniumyl]propanoate Chemical compound OC(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC AUVAVXHAOCLQBF-YUMQZZPRSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CHAJBHNQIZAJJM-RGMNGODLSA-N ethyl (2s)-2-aminopentanoate;hydrochloride Chemical compound Cl.CCC[C@H](N)C(=O)OCC CHAJBHNQIZAJJM-RGMNGODLSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229940107700 pyruvic acid Drugs 0.000 description 3
- 238000005932 reductive alkylation reaction Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- ADKDJHASTPQGEO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[b]pyrrole Chemical compound C1CNC2CCCC21 ADKDJHASTPQGEO-UHFFFAOYSA-N 0.000 description 1
- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 1
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 description 1
- PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 description 1
- ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical compound C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 description 1
- KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical compound C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 description 1
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000734 Angiotensin-1 Proteins 0.000 description 1
- 102400000344 Angiotensin-1 Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- 102400000967 Bradykinin Human genes 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 102000003729 Neprilysin Human genes 0.000 description 1
- 108090000028 Neprilysin Proteins 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 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 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- DPBOUPADTRCCIH-LURJTMIESA-N ethyl (2s)-2-aminopentanoate Chemical compound CCC[C@H](N)C(=O)OCC DPBOUPADTRCCIH-LURJTMIESA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229960002582 perindopril Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Indole Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8712901 | 1987-09-17 | ||
| FR8712901A FR2620699B1 (fr) | 1987-09-17 | 1987-09-17 | Procede de synthese d'alpha amino acides n alkyles et de leurs esters. application a la synthese de carboxyalkyl dipeptides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK515088D0 DK515088D0 (da) | 1988-09-15 |
| DK515088A DK515088A (da) | 1989-03-18 |
| DK172005B1 true DK172005B1 (da) | 1997-09-15 |
Family
ID=9354993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK515088A DK172005B1 (da) | 1987-09-17 | 1988-09-15 | Fremgangsmåde til syntese af alpha-N-alkylerede aminosyrer og estere deraf |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4902817A (xx) |
| EP (1) | EP0308340B1 (xx) |
| JP (1) | JPH0699373B2 (xx) |
| AT (1) | ATE61566T1 (xx) |
| AU (1) | AU606992B2 (xx) |
| CA (1) | CA1340570C (xx) |
| DE (1) | DE3862005D1 (xx) |
| DK (1) | DK172005B1 (xx) |
| ES (1) | ES2033451T3 (xx) |
| FR (1) | FR2620699B1 (xx) |
| GR (1) | GR3001875T3 (xx) |
| HK (1) | HK55096A (xx) |
| IE (1) | IE60994B1 (xx) |
| NZ (1) | NZ226225A (xx) |
| OA (1) | OA08959A (xx) |
| PT (1) | PT88529B (xx) |
| ZA (1) | ZA886930B (xx) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7105159B1 (en) * | 1992-11-05 | 2006-09-12 | Sloan-Kettering Institute For Cancer Research | Antibodies to prostate-specific membrane antigen |
| GB9507659D0 (en) * | 1995-04-13 | 1995-05-31 | Ass Octel | Alkylation process |
| FR2807037B1 (fr) * | 2000-03-31 | 2002-05-10 | Adir | NOUVEAU PROCEDE DE SYNTHESE DES ESTERS DE LA N-[(s)-1- CARBOXYBUTYL]-(S)-ALANINE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL |
| FR2807430B1 (fr) * | 2000-04-11 | 2002-05-17 | Adir | Nouveau procede de synthese des esters de la n-[(s)-1- carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
| AR036187A1 (es) * | 2001-07-24 | 2004-08-18 | Adir | Un proceso para la preparacion de perindopril, compuestos analogos y sus sales, compuesto intermediario 2,5-dioxo-oxazolidina y proceso para preparar un intermediario |
| EP1603558B1 (en) | 2003-02-28 | 2008-05-21 | Les Laboratoires Servier S.A. | Process for preparation of perindopril and salts thereof |
| GB0305066D0 (en) * | 2003-03-06 | 2003-04-09 | Ibm | System and method for publish/subscribe messaging |
| KR100525358B1 (ko) * | 2003-08-21 | 2005-11-04 | 주식회사 이엔에프테크놀로지 | 카르복실 벤조트리아졸 알킬에스테르의 제조방법 |
| ATE445588T1 (de) * | 2003-09-01 | 2009-10-15 | Servier Lab | Neues verfahren zur herstellung von estern des n- ((s)-1-carboxybutyl)-(s)-alanins und seine verwendung in der synthese von perindopril |
| ES2603856T3 (es) * | 2004-03-29 | 2017-03-01 | Les Laboratoires Servier | Procedimiento para preparar una composición farmacéutica sólida |
| SI21800A (sl) * | 2004-05-14 | 2005-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek sinteze perindoprila |
| WO2006006183A2 (en) * | 2004-07-12 | 2006-01-19 | Matrix Laboratories Ltd | An improved process for the preparation of n-[(s)-ethoxycarbonyl-l-butyl]-(s)-alanine |
| SI21881A (sl) | 2004-10-15 | 2006-04-30 | Diagen, Smartno Pri Ljubljani, D.O.O. | Nove kristalne oblike perindopril erbumin hidratov, postopek za njihovo pripravo in farmacevtske oblike, ki vsebujejo te spojine |
| EP1792896A1 (en) | 2005-12-01 | 2007-06-06 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the preparation of perindopril and salts thereof |
| FR2913302B1 (fr) | 2007-03-09 | 2011-07-15 | Robin Pepinieres | Conteneur pour la culture de plants et procede de preparation |
| EP3274586B1 (en) * | 2015-03-25 | 2019-11-20 | Pierburg Pump Technology GmbH | Vacuum pump |
| CN113980096A (zh) * | 2021-11-29 | 2022-01-28 | 绍兴市上虞区武汉理工大学高等研究院 | 一种吨级培哚普利叔丁胺的合成工艺方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2503155A2 (fr) * | 1980-10-02 | 1982-10-08 | Science Union & Cie | Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| US4344949A (en) * | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| US4296110A (en) * | 1980-10-28 | 1981-10-20 | E. I. Du Pont De Nemours And Company | Antihypertensive I-substituted cyclic lactam-2-carboxylic acids |
| JPS57203971A (en) * | 1981-06-09 | 1982-12-14 | Fuji Electric Co Ltd | Ac power meter |
| JPS5891974A (ja) * | 1981-11-21 | 1983-06-01 | Babcock Hitachi Kk | 気密性を高めたスライドダンパ装置 |
| DE3303344A1 (de) * | 1983-02-02 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von n-alkylierten aminosaeuren und deren estern |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| FR2620700B1 (fr) * | 1987-09-17 | 1990-06-01 | Adir | Procede de synthese d'alpha amino acides n alkyles et leurs esters. application a la synthese de carboxyalkyl dipeptides |
-
1987
- 1987-09-17 FR FR8712901A patent/FR2620699B1/fr not_active Expired - Lifetime
-
1988
- 1988-09-07 CA CA000577077A patent/CA1340570C/fr not_active Expired - Lifetime
- 1988-09-15 DK DK515088A patent/DK172005B1/da active IP Right Grant
- 1988-09-16 AU AU22355/88A patent/AU606992B2/en not_active Expired
- 1988-09-16 ES ES198888402338T patent/ES2033451T3/es not_active Expired - Lifetime
- 1988-09-16 DE DE8888402338T patent/DE3862005D1/de not_active Expired - Lifetime
- 1988-09-16 US US07/245,353 patent/US4902817A/en not_active Expired - Lifetime
- 1988-09-16 ZA ZA886930A patent/ZA886930B/xx unknown
- 1988-09-16 IE IE280588A patent/IE60994B1/en not_active IP Right Cessation
- 1988-09-16 JP JP63232124A patent/JPH0699373B2/ja not_active Expired - Lifetime
- 1988-09-16 PT PT88529A patent/PT88529B/pt not_active IP Right Cessation
- 1988-09-16 OA OA59435A patent/OA08959A/xx unknown
- 1988-09-16 EP EP19880402338 patent/EP0308340B1/fr not_active Expired - Lifetime
- 1988-09-16 NZ NZ226225A patent/NZ226225A/xx unknown
- 1988-09-16 AT AT88402338T patent/ATE61566T1/de not_active IP Right Cessation
-
1991
- 1991-04-29 GR GR91400547T patent/GR3001875T3/el unknown
-
1996
- 1996-03-28 HK HK55096A patent/HK55096A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0308340B1 (fr) | 1991-03-13 |
| JPH01110652A (ja) | 1989-04-27 |
| CA1340570C (fr) | 1999-06-01 |
| NZ226225A (en) | 1990-06-26 |
| IE60994B1 (en) | 1994-09-07 |
| ES2033451T3 (es) | 1993-03-16 |
| FR2620699B1 (fr) | 1990-06-01 |
| FR2620699A1 (fr) | 1989-03-24 |
| HK55096A (en) | 1996-04-03 |
| JPH0699373B2 (ja) | 1994-12-07 |
| US4902817A (en) | 1990-02-20 |
| OA08959A (fr) | 1990-11-30 |
| DK515088A (da) | 1989-03-18 |
| IE882805L (en) | 1989-03-17 |
| DE3862005D1 (de) | 1991-04-18 |
| AU2235588A (en) | 1989-03-23 |
| GR3001875T3 (en) | 1992-11-23 |
| ZA886930B (en) | 1989-05-30 |
| PT88529B (pt) | 1993-03-31 |
| DK515088D0 (da) | 1988-09-15 |
| EP0308340A1 (fr) | 1989-03-22 |
| PT88529A (pt) | 1988-10-01 |
| ATE61566T1 (de) | 1991-03-15 |
| AU606992B2 (en) | 1991-02-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK172005B1 (da) | Fremgangsmåde til syntese af alpha-N-alkylerede aminosyrer og estere deraf | |
| DK171470B1 (da) | Fremgangsmåde til industriel syntese af det tertiære butylaminsalt af (2S,3aS,7aS)-1-(2-[1-(ethoxycarbonyl)-(S)-butylamino]-(S)-propionyl)octahydroindol-2-carboxylsyre | |
| EP0308339B1 (fr) | Procédé de synthèse industrielle de l'acide perhydroindole carboxylique - 2 (2S, 3aS, 7aS). Application à la synthèse de carboxyalkyl dipeptides | |
| EP0309324B1 (fr) | Procédé de synthèse d'alpha amino N alkyles et de leurs esters. Application à la synthèse de carboxyalkyl dipeptides | |
| AU2005232938B2 (en) | Process for the preparation of perindopril | |
| BG65833B1 (bg) | Метод за синтез на n-[(s)-1-карбоксибутил]-(s)-аланинови естери и използването им в синтеза на периндоприл | |
| BG107234A (bg) | Нов метод за синтез на естери на n-[(s)-1-карбоксибутил]-(s)- аланин и приложението му при синтеза на периндоприл | |
| JP4563371B2 (ja) | （２ｓ，３ａｓ，７ａｓ）−ペルヒドロインドール−２−カルボン酸およびそのエステル類を合成する新規方法ならびにペリンドプリル合成のためのその使用 | |
| CN113980096A (zh) | 一种吨级培哚普利叔丁胺的合成工艺方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) |