HRP20020122A2 - Methods for crystallization of n-(1(s)-ethoxycarbonyl-3-phenylpropyl)-l-alanine n-carboxyanhydride - Google Patents
Methods for crystallization of n-(1(s)-ethoxycarbonyl-3-phenylpropyl)-l-alanine n-carboxyanhydride Download PDFInfo
- Publication number
- HRP20020122A2 HRP20020122A2 HR20020122A HRP20020122A HRP20020122A2 HR P20020122 A2 HRP20020122 A2 HR P20020122A2 HR 20020122 A HR20020122 A HR 20020122A HR P20020122 A HRP20020122 A HR P20020122A HR P20020122 A2 HRP20020122 A2 HR P20020122A2
- Authority
- HR
- Croatia
- Prior art keywords
- solvent
- solution
- process according
- good solvent
- crystallization process
- Prior art date
Links
- 238000002425 crystallisation Methods 0.000 title claims abstract description 129
- 230000008025 crystallization Effects 0.000 title claims abstract description 128
- 238000000034 method Methods 0.000 title claims description 97
- GFZFELCFSBCPDB-AAEUAGOBSA-N ethyl (2s)-2-[(4s)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutanoate Chemical compound C([C@@H](C(=O)OCC)N1C(OC(=O)[C@@H]1C)=O)CC1=CC=CC=C1 GFZFELCFSBCPDB-AAEUAGOBSA-N 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 337
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 118
- 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 description 81
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 53
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 194
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 132
- 239000013078 crystal Substances 0.000 claims description 121
- 239000000203 mixture Substances 0.000 claims description 94
- 238000007792 addition Methods 0.000 claims description 41
- 238000002156 mixing Methods 0.000 claims description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 31
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 20
- 150000008282 halocarbons Chemical group 0.000 claims description 19
- -1 aliphatic anhydride Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 14
- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 12
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 12
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 12
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 11
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 8
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 8
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 8
- 229940011051 isopropyl acetate Drugs 0.000 claims description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- 229940043232 butyl acetate Drugs 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 6
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 6
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 229940017219 methyl propionate Drugs 0.000 claims description 6
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 229940090181 propyl acetate Drugs 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000013589 supplement Substances 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 3
- 229960003767 alanine Drugs 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 239000000126 substance Substances 0.000 description 79
- 230000008929 regeneration Effects 0.000 description 29
- 238000011069 regeneration method Methods 0.000 description 29
- 238000000967 suction filtration Methods 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 230000003287 optical effect Effects 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002245 particle Substances 0.000 description 13
- 238000001914 filtration Methods 0.000 description 12
- 238000004140 cleaning Methods 0.000 description 10
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 8
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 8
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- IFTRQJLVEBNKJK-UHFFFAOYSA-N Ethylcyclopentane Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- KDIAMAVWIJYWHN-UHFFFAOYSA-N propylcyclopentane Chemical compound CCCC1CCCC1 KDIAMAVWIJYWHN-UHFFFAOYSA-N 0.000 description 4
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000005119 centrifugation Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 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
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000011085 pressure filtration Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000837 carbohydrate group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/44—Two oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000141717 | 2000-05-15 | ||
| JP2000330339 | 2000-10-30 | ||
| JP2000352892 | 2000-11-20 | ||
| PCT/JP2001/004059 WO2001087858A1 (fr) | 2000-05-15 | 2001-05-15 | Procedes de cristallisation d'un n-carboxyanhydride de n-(1(s)-ethoxycarbonyl-3-phenylpropyl)-l-alanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020122A2 true HRP20020122A2 (en) | 2003-04-30 |
Family
ID=27343377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020122A HRP20020122A2 (en) | 2000-05-15 | 2002-02-11 | Methods for crystallization of n-(1(s)-ethoxycarbonyl-3-phenylpropyl)-l-alanine n-carboxyanhydride |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6784310B2 (es) |
| EP (1) | EP1283204B1 (es) |
| JP (1) | JP4149706B2 (es) |
| KR (1) | KR100527648B1 (es) |
| CN (1) | CN1184213C (es) |
| AT (1) | ATE423106T1 (es) |
| AU (1) | AU5675801A (es) |
| CZ (1) | CZ2002532A3 (es) |
| DE (1) | DE60137686D1 (es) |
| ES (1) | ES2320413T3 (es) |
| HR (1) | HRP20020122A2 (es) |
| HU (1) | HUP0202516A3 (es) |
| IS (1) | IS6224A (es) |
| PL (1) | PL351841A1 (es) |
| SI (1) | SI20817A (es) |
| TW (1) | TW527351B (es) |
| WO (1) | WO2001087858A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1659145B2 (en) | 2003-08-29 | 2016-06-08 | Sekisui Plastics Co., Ltd. | Pre-expanded particle of olefin-modified polystyrene resin, process for producing the same, and molded foam |
| JP4852282B2 (ja) * | 2005-08-29 | 2012-01-11 | 保土谷化学工業株式会社 | Ｎ−カルボン酸無水物の製造方法 |
| CN101293887A (zh) * | 2007-04-26 | 2008-10-29 | 中国科学院福建物质结构研究所 | 一种高纯度环状硫酸酯的纯化方法 |
| JP2011016790A (ja) | 2009-06-08 | 2011-01-27 | Sumitomo Chemical Co Ltd | ピラゾリノン誘導体の精製方法 |
| WO2014202659A1 (en) | 2013-06-21 | 2014-12-24 | Sanofi-Aventis Deutschland Gmbh | Process for the preparation of amides of n-[1-(s)-(ethoxycarbonyl)-3-phenylpropyl]-l-alanine |
| CN112912369A (zh) * | 2018-09-28 | 2021-06-04 | 隆萨有限公司 | 制备n-羧基内酸酐的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496542A (en) * | 1981-03-30 | 1985-01-29 | Usv Pharmaceutical Corporation | N-substituted-amido-amino acids |
| US4831184A (en) * | 1981-03-30 | 1989-05-16 | Rorer Pharmaceutical Corporation | N-substituted-amido-amino acids |
| 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 |
| SI9200213A (en) * | 1992-09-16 | 1994-03-31 | Krka | Process for preparing alkyl-l-alanil-l-proline derivates |
| PL177163B1 (pl) | 1992-11-13 | 1999-09-30 | Du Pont | Sposób wytwarzania 2,4-oksazolidynodionów oraz nowe triazolokarboksylany i imidazolokarboksylany |
| IN184759B (es) * | 1997-07-22 | 2000-09-23 | Kaneka Corp | |
| JP4505917B2 (ja) * | 1999-01-22 | 2010-07-21 | 田辺三菱製薬株式会社 | 新規微生物およびそれを用いるｌ−アミノ酸の製法 |
-
2001
- 2001-05-15 HU HU0202516A patent/HUP0202516A3/hu unknown
- 2001-05-15 EP EP01930174A patent/EP1283204B1/en not_active Expired - Lifetime
- 2001-05-15 DE DE60137686T patent/DE60137686D1/de not_active Expired - Lifetime
- 2001-05-15 JP JP2001584254A patent/JP4149706B2/ja not_active Expired - Fee Related
- 2001-05-15 TW TW090111623A patent/TW527351B/zh not_active IP Right Cessation
- 2001-05-15 WO PCT/JP2001/004059 patent/WO2001087858A1/ja active IP Right Grant
- 2001-05-15 CN CNB018012582A patent/CN1184213C/zh not_active Expired - Lifetime
- 2001-05-15 AU AU56758/01A patent/AU5675801A/en not_active Abandoned
- 2001-05-15 PL PL01351841A patent/PL351841A1/xx not_active IP Right Cessation
- 2001-05-15 SI SI200120002A patent/SI20817A/sl not_active IP Right Cessation
- 2001-05-15 KR KR10-2002-7000541A patent/KR100527648B1/ko active IP Right Grant
- 2001-05-15 US US10/019,318 patent/US6784310B2/en not_active Expired - Fee Related
- 2001-05-15 AT AT01930174T patent/ATE423106T1/de active
- 2001-05-15 ES ES01930174T patent/ES2320413T3/es not_active Expired - Lifetime
- 2001-05-15 CZ CZ2002532A patent/CZ2002532A3/cs unknown
-
2002
- 2002-01-09 IS IS6224A patent/IS6224A/is unknown
- 2002-02-11 HR HR20020122A patent/HRP20020122A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1283204A4 (en) | 2007-09-05 |
| TW527351B (en) | 2003-04-11 |
| HUP0202516A2 (hu) | 2003-01-28 |
| US6784310B2 (en) | 2004-08-31 |
| SI20817A (sl) | 2002-08-31 |
| EP1283204B1 (en) | 2009-02-18 |
| JP4149706B2 (ja) | 2008-09-17 |
| EP1283204A1 (en) | 2003-02-12 |
| CZ2002532A3 (cs) | 2002-05-15 |
| IS6224A (is) | 2002-01-09 |
| AU5675801A (en) | 2001-11-26 |
| ES2320413T3 (es) | 2009-05-22 |
| ATE423106T1 (de) | 2009-03-15 |
| KR100527648B1 (ko) | 2005-11-09 |
| PL351841A1 (en) | 2003-06-16 |
| US20020137944A1 (en) | 2002-09-26 |
| CN1380881A (zh) | 2002-11-20 |
| WO2001087858A1 (fr) | 2001-11-22 |
| HUP0202516A3 (en) | 2003-04-28 |
| KR20020038689A (ko) | 2002-05-23 |
| CN1184213C (zh) | 2005-01-12 |
| DE60137686D1 (de) | 2009-04-02 |
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