NO850943L - Fremgangsmaate ved fremstilling av dl-beta-arylaminosyrer - Google Patents
Fremgangsmaate ved fremstilling av dl-beta-arylaminosyrerInfo
- Publication number
- NO850943L NO850943L NO850943A NO850943A NO850943L NO 850943 L NO850943 L NO 850943L NO 850943 A NO850943 A NO 850943A NO 850943 A NO850943 A NO 850943A NO 850943 L NO850943 L NO 850943L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- hydantoin
- sub
- aryl
- amount
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000002253 acid Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 150000007513 acids Chemical class 0.000 title 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229940091173 hydantoin Drugs 0.000 claims abstract description 24
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims abstract description 23
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000011541 reaction mixture Substances 0.000 claims abstract description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004471 Glycine Substances 0.000 claims abstract description 10
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 239000004202 carbamide Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 5
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 54
- 239000000243 solution Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 10
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- FZEZBTXZYHRMPD-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methyl]imidazolidine-2,4-dione Chemical compound COC1=CC=CC=C1CC1C(=O)NC(=O)N1 FZEZBTXZYHRMPD-UHFFFAOYSA-N 0.000 description 9
- MIPHJRZSHMVBJB-UHFFFAOYSA-N 5-[(3,4,5-trimethoxyphenyl)methylidene]imidazolidine-2,4-dione Chemical compound COC1=C(OC)C(OC)=CC(C=C2C(NC(=O)N2)=O)=C1 MIPHJRZSHMVBJB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 5
- UDTSPKADQGPZFS-SOFGYWHQSA-N (5e)-5-benzylideneimidazolidine-2,4-dione Chemical compound N1C(=O)NC(=O)\C1=C/C1=CC=CC=C1 UDTSPKADQGPZFS-SOFGYWHQSA-N 0.000 description 4
- UDTSPKADQGPZFS-UHFFFAOYSA-N 1/7/3775 Natural products N1C(=O)NC(=O)C1=CC1=CC=CC=C1 UDTSPKADQGPZFS-UHFFFAOYSA-N 0.000 description 4
- FYWDUQCSMYWUHV-UHFFFAOYSA-N 3-chloro-5-hydroxypentan-2-one Chemical compound CC(=O)C(Cl)CCO FYWDUQCSMYWUHV-UHFFFAOYSA-N 0.000 description 4
- DBOMTIHROGSFTI-UHFFFAOYSA-N 5-benzylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1CC1=CC=CC=C1 DBOMTIHROGSFTI-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YOFKIDCKEYKPNO-SOFGYWHQSA-N (5e)-5-[(2-methoxyphenyl)methylidene]imidazolidine-2,4-dione Chemical compound COC1=CC=CC=C1\C=C\1C(=O)NC(=O)N/1 YOFKIDCKEYKPNO-SOFGYWHQSA-N 0.000 description 2
- XLTKBDZXXGQCSC-RMKNXTFCSA-N (5e)-5-[(4-methoxyphenyl)methylidene]imidazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1\C=C\1C(=O)NC(=O)N/1 XLTKBDZXXGQCSC-RMKNXTFCSA-N 0.000 description 2
- 150000008575 L-amino acids Chemical class 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- -1 lactic acid nitrile Chemical class 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
- SEUPQWHWULSGJC-UHFFFAOYSA-N 2-azaniumyl-3-(2-methoxyphenyl)propanoate Chemical compound COC1=CC=CC=C1CC(N)C(O)=O SEUPQWHWULSGJC-UHFFFAOYSA-N 0.000 description 1
- AYPXBNMIJGVJDE-UHFFFAOYSA-N 2-azaniumyl-3-(3,4,5-trimethoxyphenyl)propanoate Chemical compound COC1=CC(CC(N)C(O)=O)=CC(OC)=C1OC AYPXBNMIJGVJDE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- GSZKVZIUICNVHR-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]imidazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1CC1C(=O)NC(=O)N1 GSZKVZIUICNVHR-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- GEYBMYRBIABFTA-UHFFFAOYSA-N O-methyltyrosine Chemical compound COC1=CC=C(CC(N)C(O)=O)C=C1 GEYBMYRBIABFTA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910001422 barium ion Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU84981A HU204026B (en) | 1984-03-12 | 1984-03-12 | Process for producing di-beta-substituted phenylamino acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO850943L true NO850943L (no) | 1985-09-13 |
Family
ID=10952297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO850943A NO850943L (no) | 1984-03-12 | 1985-03-11 | Fremgangsmaate ved fremstilling av dl-beta-arylaminosyrer |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4647694A (fi) |
| EP (1) | EP0156582B1 (fi) |
| JP (1) | JPS60204750A (fi) |
| AT (1) | ATE37177T1 (fi) |
| AU (1) | AU3968185A (fi) |
| BG (1) | BG43688A3 (fi) |
| DD (1) | DD232260A5 (fi) |
| DE (1) | DE3564938D1 (fi) |
| DK (1) | DK109985A (fi) |
| ES (1) | ES541070A0 (fi) |
| FI (1) | FI850970L (fi) |
| HU (1) | HU204026B (fi) |
| IL (1) | IL74389A0 (fi) |
| NO (1) | NO850943L (fi) |
| PL (1) | PL252344A1 (fi) |
| RO (1) | RO92676B (fi) |
| SU (1) | SU1468409A3 (fi) |
| YU (1) | YU39085A (fi) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4613691A (en) * | 1984-08-17 | 1986-09-23 | Stauffer Chemical Company | Preparation of amino acids from unsaturated hydantoins |
| DE4137581A1 (de) * | 1991-11-15 | 1993-05-19 | Degussa | Verfahren zur chemischen racemisierung von 5-monosubstituierten hydantoinen, vorrichtung zur durchfuehrung des verfahrens und verwendung der hydantoine |
| FR2735126B1 (fr) * | 1995-06-12 | 1997-07-18 | Rhone Poulenc Rorer Sa | Procede de preparation des formes enantiomeres de l'acide amino alkylaminophenylpropanoique |
| DK1427721T3 (da) * | 2001-09-05 | 2008-06-02 | Solvay | Fremgangsmåde til syntese af 5 (3 pyridylmethylen)-imidazolidin-2,4 dion |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2479065A (en) * | 1945-09-06 | 1949-08-16 | Du Pont | Preparation of 5-benzylhydantoin |
| US2605282A (en) * | 1949-02-18 | 1952-07-29 | Dow Chemical Co | Process for production of beta-(3, 4-dihydroxyphenyl)-alanine |
| US2861079A (en) * | 1956-06-04 | 1958-11-18 | Dow Chemical Co | Process for making unsaturated hydantoins |
| GB991644A (en) * | 1961-10-30 | 1965-05-12 | Rafa House Biolog Lab Ltd | Manufacture of hydantoin derivatives |
| US3190914A (en) * | 1963-05-27 | 1965-06-22 | Rexall Drug Chemical | Process for the preparation of amino acids |
| US3215736A (en) * | 1964-03-20 | 1965-11-02 | Prod Chim Ind S P C I Soc D | Preparation of amino acids |
| NL128182C (fi) * | 1965-11-30 | |||
| CH483397A (de) * | 1966-12-01 | 1969-12-31 | Hoffmann La Roche | Verfahren zur Herstellung von Phenylalaninderivaten |
| GB1310510A (en) * | 1969-06-10 | 1973-03-21 | Zundel J | Preparation of alpha-aminoacids from hydantoins |
| GB1456857A (en) * | 1972-11-24 | 1976-12-01 | Teijin Ltd | Process for the production of hydantoin derivatives |
| US4175198A (en) * | 1976-10-07 | 1979-11-20 | W. R. Grace & Co. | 5-Secondary alkylidene hydantoins |
| JPS54106470A (en) * | 1978-02-09 | 1979-08-21 | Ajinomoto Co Inc | Preparation of 5-aryl-hydantoin |
| JPS54106469A (en) * | 1978-02-09 | 1979-08-21 | Ajinomoto Co Inc | Preparation of 5-aryl-hydantoin |
| JPS54128572A (en) * | 1978-03-25 | 1979-10-05 | Ajinomoto Co Inc | Preparation of 5-arylhydantoin |
| JPS54138559A (en) * | 1978-04-19 | 1979-10-27 | Ajinomoto Co Inc | Preparation of 5-aryl-hydantoin |
| DE3013626C2 (de) * | 1980-04-09 | 1985-06-27 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5-Arylidenhydantoinen (A) |
-
1984
- 1984-03-12 HU HU84981A patent/HU204026B/hu not_active IP Right Cessation
-
1985
- 1985-02-20 IL IL74389A patent/IL74389A0/xx unknown
- 1985-03-08 AU AU39681/85A patent/AU3968185A/en not_active Abandoned
- 1985-03-08 ES ES541070A patent/ES541070A0/es active Granted
- 1985-03-11 DD DD85274004A patent/DD232260A5/de unknown
- 1985-03-11 SU SU853865852A patent/SU1468409A3/ru active
- 1985-03-11 RO RO117934A patent/RO92676B/ro unknown
- 1985-03-11 BG BG8569188A patent/BG43688A3/xx unknown
- 1985-03-11 NO NO850943A patent/NO850943L/no unknown
- 1985-03-11 DK DK109985A patent/DK109985A/da not_active Application Discontinuation
- 1985-03-12 US US06/710,838 patent/US4647694A/en not_active Expired - Fee Related
- 1985-03-12 FI FI850970A patent/FI850970L/fi not_active Application Discontinuation
- 1985-03-12 AT AT85301707T patent/ATE37177T1/de active
- 1985-03-12 EP EP85301707A patent/EP0156582B1/en not_active Expired
- 1985-03-12 JP JP60047597A patent/JPS60204750A/ja active Pending
- 1985-03-12 PL PL25234485A patent/PL252344A1/xx unknown
- 1985-03-12 DE DE8585301707T patent/DE3564938D1/de not_active Expired
- 1985-03-12 YU YU00390/85A patent/YU39085A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU1468409A3 (ru) | 1989-03-23 |
| RO92676B (ro) | 1987-12-01 |
| BG43688A3 (en) | 1988-07-15 |
| HU204026B (en) | 1991-11-28 |
| EP0156582A1 (en) | 1985-10-02 |
| JPS60204750A (ja) | 1985-10-16 |
| RO92676A (ro) | 1987-11-30 |
| IL74389A0 (en) | 1985-05-31 |
| FI850970A0 (fi) | 1985-03-12 |
| EP0156582B1 (en) | 1988-09-14 |
| ES8601854A1 (es) | 1985-12-01 |
| FI850970L (fi) | 1985-09-13 |
| DE3564938D1 (en) | 1988-10-20 |
| YU39085A (en) | 1987-04-30 |
| ATE37177T1 (de) | 1988-09-15 |
| ES541070A0 (es) | 1985-12-01 |
| DD232260A5 (de) | 1986-01-22 |
| AU3968185A (en) | 1985-09-19 |
| PL252344A1 (en) | 1985-11-19 |
| DK109985D0 (da) | 1985-03-11 |
| US4647694A (en) | 1987-03-03 |
| DK109985A (da) | 1985-09-13 |
| HUT39717A (en) | 1986-10-29 |
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