HU182778B - Process for preparing 4-/n-alkyl-carbamoyloxy/-l-proline - Google Patents
Process for preparing 4-/n-alkyl-carbamoyloxy/-l-proline Download PDFInfo
- Publication number
- HU182778B HU182778B HU813412A HU341280A HU182778B HU 182778 B HU182778 B HU 182778B HU 813412 A HU813412 A HU 813412A HU 341280 A HU341280 A HU 341280A HU 182778 B HU182778 B HU 182778B
- Authority
- HU
- Hungary
- Prior art keywords
- proline
- formula
- benzyloxycarbonyl
- trans
- methylcarbamoyloxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 18
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 18
- 229960002429 proline Drugs 0.000 claims description 17
- -1 N-methylcarbamoyloxy Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 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 claims description 3
- 229930182821 L-proline Natural products 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- FGMPLJWBKKVCDB-BYPYZUCNSA-N (2s)-1-hydroxypyrrolidine-2-carboxylic acid Chemical class ON1CCC[C@H]1C(O)=O FGMPLJWBKKVCDB-BYPYZUCNSA-N 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 235000013930 proline Nutrition 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 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 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- WWVCWLBEARZMAH-MNOVXSKESA-N (2s,4r)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound C1[C@H](O)C[C@@H](C(O)=O)N1C(=O)OCC1=CC=CC=C1 WWVCWLBEARZMAH-MNOVXSKESA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 150000003147 proline derivatives Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US317879A | 1979-01-15 | 1979-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182778B true HU182778B (en) | 1984-03-28 |
Family
ID=21704564
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU813412A HU182778B (en) | 1979-01-15 | 1980-01-14 | Process for preparing 4-/n-alkyl-carbamoyloxy/-l-proline |
| HU808065A HU179621B (en) | 1979-01-15 | 1980-01-14 | Process for preparing carbamete derivatives of mercapto-acyl-hydroxy-l-proline |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU808065A HU179621B (en) | 1979-01-15 | 1980-01-14 | Process for preparing carbamete derivatives of mercapto-acyl-hydroxy-l-proline |
Country Status (21)
| Country | Link |
|---|---|
| JP (2) | JPS5598161A (OSRAM) |
| AT (1) | AT364377B (OSRAM) |
| AU (1) | AU526767B2 (OSRAM) |
| BE (1) | BE881153A (OSRAM) |
| CA (1) | CA1138452A (OSRAM) |
| CH (2) | CH646950A5 (OSRAM) |
| DE (1) | DE3001113A1 (OSRAM) |
| DK (1) | DK14980A (OSRAM) |
| FR (1) | FR2446281A1 (OSRAM) |
| GB (2) | GB2088875B (OSRAM) |
| GR (1) | GR73002B (OSRAM) |
| HU (2) | HU182778B (OSRAM) |
| IE (1) | IE49357B1 (OSRAM) |
| IT (1) | IT1140505B (OSRAM) |
| LU (1) | LU82082A1 (OSRAM) |
| NL (1) | NL8000206A (OSRAM) |
| NO (1) | NO800077L (OSRAM) |
| NZ (1) | NZ192522A (OSRAM) |
| PH (2) | PH14946A (OSRAM) |
| SE (1) | SE8000298L (OSRAM) |
| ZA (1) | ZA8035B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4316905A (en) * | 1980-07-01 | 1982-02-23 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of various 4-substituted prolines |
| CA1258853A (en) * | 1982-04-30 | 1989-08-29 | Rudiger D. Haugwitz | Substituted 4-phenoxy prolines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046889A (en) * | 1976-02-13 | 1977-09-06 | E. R. Squibb & Sons, Inc. | Azetidine-2-carboxylic acid derivatives |
| US4052511A (en) * | 1976-02-13 | 1977-10-04 | E. R. Squibb & Sons, Inc. | Carboxyacylproline derivatives |
| AU509899B2 (en) * | 1976-02-13 | 1980-05-29 | E.R. Squibb & Sons, Inc. | Proline derivatives and related compounds |
-
1980
- 1980-01-02 CA CA000342899A patent/CA1138452A/en not_active Expired
- 1980-01-03 AU AU54327/80A patent/AU526767B2/en not_active Ceased
- 1980-01-03 ZA ZA00800035A patent/ZA8035B/xx unknown
- 1980-01-04 NZ NZ192522A patent/NZ192522A/xx unknown
- 1980-01-10 IE IE48/80A patent/IE49357B1/en unknown
- 1980-01-10 FR FR8000500A patent/FR2446281A1/fr active Granted
- 1980-01-11 GR GR60934A patent/GR73002B/el unknown
- 1980-01-11 PH PH23504A patent/PH14946A/en unknown
- 1980-01-11 CH CH24080A patent/CH646950A5/de not_active IP Right Cessation
- 1980-01-14 HU HU813412A patent/HU182778B/hu not_active IP Right Cessation
- 1980-01-14 LU LU82082A patent/LU82082A1/fr unknown
- 1980-01-14 DE DE19803001113 patent/DE3001113A1/de not_active Ceased
- 1980-01-14 NL NL8000206A patent/NL8000206A/nl not_active Application Discontinuation
- 1980-01-14 NO NO800077A patent/NO800077L/no unknown
- 1980-01-14 IT IT19209/80A patent/IT1140505B/it active
- 1980-01-14 HU HU808065A patent/HU179621B/hu not_active IP Right Cessation
- 1980-01-14 SE SE8000298A patent/SE8000298L/xx not_active Application Discontinuation
- 1980-01-14 GB GB8200442A patent/GB2088875B/en not_active Expired
- 1980-01-14 DK DK14980A patent/DK14980A/da unknown
- 1980-01-14 JP JP300580A patent/JPS5598161A/ja active Granted
- 1980-01-14 GB GB8001117A patent/GB2040937B/en not_active Expired
- 1980-01-15 BE BE0/198972A patent/BE881153A/fr not_active IP Right Cessation
- 1980-01-15 AT AT0019080A patent/AT364377B/de not_active IP Right Cessation
- 1980-08-13 PH PH24438A patent/PH15318A/en unknown
-
1983
- 1983-11-17 CH CH619383A patent/CH646690A5/de not_active IP Right Cessation
-
1988
- 1988-12-16 JP JP63319342A patent/JPH01301656A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AT364377B (de) | 1981-10-12 |
| SE8000298L (sv) | 1980-07-16 |
| ZA8035B (en) | 1980-12-31 |
| GB2088875A (en) | 1982-06-16 |
| GB2040937B (en) | 1982-11-24 |
| JPH0125744B2 (OSRAM) | 1989-05-19 |
| JPH01301656A (ja) | 1989-12-05 |
| ATA19080A (de) | 1981-03-15 |
| CH646690A5 (de) | 1984-12-14 |
| NZ192522A (en) | 1982-06-29 |
| DK14980A (da) | 1980-07-16 |
| BE881153A (fr) | 1980-07-15 |
| PH15318A (en) | 1982-11-18 |
| LU82082A1 (fr) | 1980-04-23 |
| IE800048L (en) | 1980-07-15 |
| CA1138452A (en) | 1982-12-28 |
| NL8000206A (nl) | 1980-07-17 |
| GB2040937A (en) | 1980-09-03 |
| GB2088875B (en) | 1983-06-08 |
| DE3001113A1 (de) | 1980-07-24 |
| CH646950A5 (de) | 1984-12-28 |
| IT8019209A0 (it) | 1980-01-14 |
| JPH0378378B2 (OSRAM) | 1991-12-13 |
| PH14946A (en) | 1982-02-02 |
| JPS5598161A (en) | 1980-07-25 |
| IT1140505B (it) | 1986-10-01 |
| AU526767B2 (en) | 1983-01-27 |
| AU5432780A (en) | 1980-07-24 |
| FR2446281B1 (OSRAM) | 1984-01-20 |
| HU179621B (en) | 1982-11-29 |
| NO800077L (no) | 1980-07-16 |
| GR73002B (OSRAM) | 1984-01-24 |
| FR2446281A1 (fr) | 1980-08-08 |
| IE49357B1 (en) | 1985-09-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU747422A3 (ru) | Способ получени производных пролина | |
| KR100555970B1 (ko) | 2-아미노-1,3-프로판디올유도체의 제조방법 | |
| GB1575709A (en) | 1,1-cycloalkyldiacetic acid imide derivatives and their use for preparing 1-aminomethyl-1-cycloalkylacetic acids | |
| HU196198B (en) | Process for producing cis-1-aryl-2-(fluoromethyl)-oxiranes | |
| FR2545490A1 (fr) | Procede de production de chlorhydrate de diltiazem en tant que produit antagoniste du calcium | |
| US5144042A (en) | Process for preparing optically active 3-hydroxypyrrolidine derivatives | |
| HU205116B (en) | Process for producing 1,4-diazabicyclo/3.2.2./nonane | |
| HU182778B (en) | Process for preparing 4-/n-alkyl-carbamoyloxy/-l-proline | |
| HU176871B (en) | Process for producing 2-amino-oktahydro-oxasolo-square bracket-3,2-a-square bracket closed-pyrrolo-square bracket-2,1-c-square bracket closed-pyrasine derivatives | |
| US5399763A (en) | Process for preparing optically active 2-aminopropanal | |
| EP1864973A1 (en) | Process for the preparation of perindopril and salts thereof | |
| AU661722B2 (en) | Substituted hydroquinone derivatives | |
| US4170596A (en) | Novel monoesters of cis-cyclopentenediol, process for preparation thereof, and process for preparation of lactones from the monoesters | |
| US5142066A (en) | Stereoselective process for the preparation of 2-amino-ethanol derivatives having a central analgesic activity and intermidiates thereof | |
| HU196959B (en) | Process for producing merkapto-acyl-proline derivatives | |
| FI71933B (fi) | Nya l-vinsyra-o-monoestrar av 3-morfolino-4-(3'-tert -butylamino-2'-hydroxipropoxi)-1,2,5-tiadiazol och deras anvaendning saosom mellanprodukter | |
| US4217284A (en) | Process for preparation of optically pure lactones from monoesters of cis-cyclopentenediol | |
| CA1273932A (en) | Process for production of dihydropyridine compound or salts thereof | |
| US6172234B1 (en) | Optically active cyclic amino acid ester derivatives and processes for producing the same | |
| KR100209298B1 (ko) | 새로운 아민고리 화합물 | |
| US4851514A (en) | Process for preparing a compound useful in preparing ace inhibitors and intermediate produced thereby | |
| HU185493B (en) | Process for producing new azabicyclo-bracket-3.2.0-bracket closedheptene derivatives | |
| JP2818890B2 (ja) | アリルアミン化合物の製造方法および同化合物の製造用中間体の製造方法 | |
| KR20010095169A (ko) | 방향족 카복실산 유도체의 제조방법 | |
| JP2739505B2 (ja) | 光学活性３，４―デヒドロピロリジン化合物の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |