DE2824116A1 - Alpha -fluormethyl- alpha -amino- alkansaeuren - Google Patents
Alpha -fluormethyl- alpha -amino- alkansaeurenInfo
- Publication number
- DE2824116A1 DE2824116A1 DE19782824116 DE2824116A DE2824116A1 DE 2824116 A1 DE2824116 A1 DE 2824116A1 DE 19782824116 DE19782824116 DE 19782824116 DE 2824116 A DE2824116 A DE 2824116A DE 2824116 A1 DE2824116 A1 DE 2824116A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- compound according
- cooh
- meaning
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims description 20
- 150000007513 acids Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 claims description 2
- 101100019690 Homo sapiens KAT6B gene Proteins 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 36
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- 238000001816 cooling Methods 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 12
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 11
- 229940024606 amino acid Drugs 0.000 description 11
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- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 9
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- 238000002844 melting Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
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- 229960003104 ornithine Drugs 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
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- 239000000706 filtrate Substances 0.000 description 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 4
- KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 description 3
- MQDPXCNKVNOCEE-ZCFIWIBFSA-N (2s)-2-amino-2-(fluoromethyl)pentanedioic acid Chemical compound FC[C@@](N)(C(O)=O)CCC(O)=O MQDPXCNKVNOCEE-ZCFIWIBFSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
- 241001279009 Strychnos toxifera Species 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000002983 circular dichroism Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- 229960005453 strychnine Drugs 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NRNSHPCDKHOUOE-SNVBAGLBSA-N (2s)-2-amino-2-[(3,4-dihydroxyphenyl)methyl]-3-fluoropropanoic acid Chemical compound FC[C@@](N)(C(O)=O)CC1=CC=C(O)C(O)=C1 NRNSHPCDKHOUOE-SNVBAGLBSA-N 0.000 description 2
- AJFGLTPLWPTALJ-SSDOTTSWSA-N (2s)-2-azaniumyl-2-(fluoromethyl)-3-(1h-imidazol-5-yl)propanoate Chemical compound FC[C@@](N)(C(O)=O)CC1=CN=CN1 AJFGLTPLWPTALJ-SSDOTTSWSA-N 0.000 description 2
- -1 2-ethylhexyl Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- 206010020772 Hypertension Diseases 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
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- ITIRWANLQJECKK-FYZOBXCZSA-N (2s)-2-amino-2-(fluoromethyl)pentanedioic acid;hydrochloride Chemical compound Cl.FC[C@@](N)(C(O)=O)CCC(O)=O ITIRWANLQJECKK-FYZOBXCZSA-N 0.000 description 1
- QHSCIWIRXWFIGH-LURJTMIESA-N (2s)-2-amino-2-methylpentanedioic acid Chemical class OC(=O)[C@](N)(C)CCC(O)=O QHSCIWIRXWFIGH-LURJTMIESA-N 0.000 description 1
- SLEAPJHLNGFZHW-SCSAIBSYSA-N (2s)-2-amino-3-fluoro-2-methylpropanoic acid Chemical compound FC[C@](N)(C)C(O)=O SLEAPJHLNGFZHW-SCSAIBSYSA-N 0.000 description 1
- ZAJPVQSJWGQONE-SSDOTTSWSA-N (2s)-2-amino-5-(diaminomethylideneamino)-2-(fluoromethyl)pentanoic acid Chemical compound NC(=N)NCCC[C@@](N)(CF)C(O)=O ZAJPVQSJWGQONE-SSDOTTSWSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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- 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
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 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
- 230000036962 time dependent Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (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)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80238977A | 1977-06-01 | 1977-06-01 | |
| US05/802,391 US4325961A (en) | 1977-06-01 | 1977-06-01 | Fluorinated amino acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2824116A1 true DE2824116A1 (de) | 1978-12-14 |
| DE2824116C2 DE2824116C2 (en, 2012) | 1989-04-27 |
Family
ID=27122442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782824116 Granted DE2824116A1 (de) | 1977-06-01 | 1978-06-01 | Alpha -fluormethyl- alpha -amino- alkansaeuren |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5416423A (en, 2012) |
| AR (1) | AR223463A1 (en, 2012) |
| AT (1) | AT360509B (en, 2012) |
| AU (1) | AU518479B2 (en, 2012) |
| CA (1) | CA1120040A (en, 2012) |
| CH (1) | CH639639A5 (en, 2012) |
| DD (1) | DD138651A5 (en, 2012) |
| DE (1) | DE2824116A1 (en, 2012) |
| DK (1) | DK149841C (en, 2012) |
| ES (1) | ES470296A1 (en, 2012) |
| FI (1) | FI66840C (en, 2012) |
| FR (1) | FR2392958A1 (en, 2012) |
| GB (1) | GB1602525A (en, 2012) |
| GR (1) | GR64495B (en, 2012) |
| HK (1) | HK18184A (en, 2012) |
| HU (1) | HU181911B (en, 2012) |
| IE (1) | IE46983B1 (en, 2012) |
| IT (1) | IT1104709B (en, 2012) |
| LU (1) | LU79750A1 (en, 2012) |
| NL (1) | NL190485C (en, 2012) |
| NO (1) | NO147382C (en, 2012) |
| NZ (1) | NZ187377A (en, 2012) |
| PL (1) | PL115731B1 (en, 2012) |
| PT (1) | PT68102B (en, 2012) |
| SE (1) | SE7806440L (en, 2012) |
| YU (1) | YU129178A (en, 2012) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828738A1 (de) * | 1977-07-11 | 1979-02-01 | Merrell Toraude & Co | Alpha -halogenmethyl-aminosaeuren und verfahren zu ihrer herstellung |
| DE2828739A1 (de) * | 1977-07-11 | 1979-02-01 | Merrell Toraude & Co | Alpha -halogenmethylderivate von alpha-aminosaeuren |
| DE2832309A1 (de) * | 1977-07-28 | 1979-02-08 | Merrell Toraude & Co | Alpha -halogenmethylderivate von aminosaeuren |
| EP0007600A1 (en) * | 1978-07-24 | 1980-02-06 | Merck & Co. Inc. | Alpha-difluoromethyl amino acids and pharmaceutical composition containing the same |
| DE3012641A1 (de) * | 1979-04-26 | 1980-11-06 | Merrell Toraude & Co | Alpha -halogen-aminosaeuren und verfahren zu ihrer herstellung |
| EP0025370A3 (en) * | 1979-07-26 | 1981-06-03 | Merrell Toraude Et Compagnie | Preparation of fluorinated methylaminoalkanoic acids, process intermediates and their preparation |
| EP0040150A1 (en) * | 1980-05-09 | 1981-11-18 | Merrell Toraude Et Compagnie | Fluoromethylated tyrosine methyl ester |
| WO1995015940A1 (en) * | 1993-12-10 | 1995-06-15 | University Of Bristol | Alpha-quaternary-alpha-amino acids for use as cns agents |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL59481A0 (en) * | 1977-07-11 | 1980-05-30 | Merrell Toraude & Co | -halomethyl amino acids |
| CA1174603A (en) * | 1980-06-16 | 1984-09-18 | Albert Sjoerdsma | Method of inhibiting the growth of protozoa |
| US4421767A (en) * | 1981-06-01 | 1983-12-20 | Merrell Toraude Et Compagnie | Compounds and methods for treating depression |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3046300A (en) * | 1960-10-21 | 1962-07-24 | Merck & Co Inc | alpha-trifluoromethyloxyphenylalanines |
-
1978
- 1978-05-25 FR FR7815567A patent/FR2392958A1/fr active Granted
- 1978-05-25 GR GR56328A patent/GR64495B/el unknown
- 1978-05-25 NZ NZ187377A patent/NZ187377A/xx unknown
- 1978-05-26 FI FI781674A patent/FI66840C/fi not_active IP Right Cessation
- 1978-05-26 AR AR272336A patent/AR223463A1/es active
- 1978-05-29 AU AU36586/78A patent/AU518479B2/en not_active Expired
- 1978-05-29 CA CA000304318A patent/CA1120040A/en not_active Expired
- 1978-05-29 ES ES470296A patent/ES470296A1/es not_active Expired
- 1978-05-30 GB GB24330/78A patent/GB1602525A/en not_active Expired
- 1978-05-30 PT PT68102A patent/PT68102B/pt unknown
- 1978-05-30 DK DK237978A patent/DK149841C/da not_active IP Right Cessation
- 1978-05-30 DD DD78205669A patent/DD138651A5/xx unknown
- 1978-05-30 AT AT393278A patent/AT360509B/de not_active IP Right Cessation
- 1978-05-30 YU YU01291/78A patent/YU129178A/xx unknown
- 1978-05-30 IE IE1078/78A patent/IE46983B1/en unknown
- 1978-05-30 HU HU78ME2169A patent/HU181911B/hu unknown
- 1978-05-31 PL PL1978207242A patent/PL115731B1/pl unknown
- 1978-05-31 NO NO781892A patent/NO147382C/no unknown
- 1978-05-31 IT IT49637/78A patent/IT1104709B/it active
- 1978-05-31 CH CH597978A patent/CH639639A5/de not_active IP Right Cessation
- 1978-06-01 NL NLAANVRAGE7805981,A patent/NL190485C/xx not_active IP Right Cessation
- 1978-06-01 JP JP6501678A patent/JPS5416423A/ja active Granted
- 1978-06-01 SE SE7806440A patent/SE7806440L/xx unknown
- 1978-06-01 LU LU79750A patent/LU79750A1/xx unknown
- 1978-06-01 DE DE19782824116 patent/DE2824116A1/de active Granted
-
1984
- 1984-03-01 HK HK181/84A patent/HK18184A/en not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828738A1 (de) * | 1977-07-11 | 1979-02-01 | Merrell Toraude & Co | Alpha -halogenmethyl-aminosaeuren und verfahren zu ihrer herstellung |
| DE2828739A1 (de) * | 1977-07-11 | 1979-02-01 | Merrell Toraude & Co | Alpha -halogenmethylderivate von alpha-aminosaeuren |
| DE2832309A1 (de) * | 1977-07-28 | 1979-02-08 | Merrell Toraude & Co | Alpha -halogenmethylderivate von aminosaeuren |
| EP0007600A1 (en) * | 1978-07-24 | 1980-02-06 | Merck & Co. Inc. | Alpha-difluoromethyl amino acids and pharmaceutical composition containing the same |
| DE3012641A1 (de) * | 1979-04-26 | 1980-11-06 | Merrell Toraude & Co | Alpha -halogen-aminosaeuren und verfahren zu ihrer herstellung |
| DE3012581A1 (de) * | 1979-04-26 | 1980-11-13 | Merrell Toraude & Co | Verfahren zur herstellung von alpha -halogen-aminosaeuren |
| EP0025370A3 (en) * | 1979-07-26 | 1981-06-03 | Merrell Toraude Et Compagnie | Preparation of fluorinated methylaminoalkanoic acids, process intermediates and their preparation |
| EP0040150A1 (en) * | 1980-05-09 | 1981-11-18 | Merrell Toraude Et Compagnie | Fluoromethylated tyrosine methyl ester |
| WO1995015940A1 (en) * | 1993-12-10 | 1995-06-15 | University Of Bristol | Alpha-quaternary-alpha-amino acids for use as cns agents |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |