CA1053697A - Synthesis of racemic 2-deutero-3-fluoro-alanine and its salts, and intermediates therefor - Google Patents
Synthesis of racemic 2-deutero-3-fluoro-alanine and its salts, and intermediates thereforInfo
- Publication number
- CA1053697A CA1053697A CA238,618A CA238618A CA1053697A CA 1053697 A CA1053697 A CA 1053697A CA 238618 A CA238618 A CA 238618A CA 1053697 A CA1053697 A CA 1053697A
- Authority
- CA
- Canada
- Prior art keywords
- fluoro
- salt
- solution
- deutero
- alanine
- 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.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 24
- UYTSRQMXRROFPU-MYSWAXPFSA-N (2r)-2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FC[C@@](N)([2H])C(O)=O UYTSRQMXRROFPU-MYSWAXPFSA-N 0.000 title abstract description 9
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 239000000543 intermediate Substances 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title 1
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 12
- CXABZTLXNODUTD-UHFFFAOYSA-N 3-fluoropyruvic acid Chemical compound OC(=O)C(=O)CF CXABZTLXNODUTD-UHFFFAOYSA-N 0.000 claims abstract description 11
- UYTSRQMXRROFPU-VMNATFBRSA-N 2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FCC(N)([2H])C(O)=O UYTSRQMXRROFPU-VMNATFBRSA-N 0.000 claims abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 47
- 239000000243 solution Substances 0.000 claims description 45
- 229910021529 ammonia Inorganic materials 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 14
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 230000002829 reductive effect Effects 0.000 claims description 10
- -1 alkaline earth metal salt Chemical class 0.000 claims description 9
- OSYXANRNDYBMOU-UHFFFAOYSA-N 3-fluoro-2-iminopropanoic acid Chemical compound OC(=O)C(=N)CF OSYXANRNDYBMOU-UHFFFAOYSA-N 0.000 claims description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims description 7
- 239000012354 sodium borodeuteride Substances 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- RRYOTPCFMILDDZ-UHFFFAOYSA-M lithium;3-fluoro-2-oxopropanoate;hydrate Chemical compound [Li+].O.[O-]C(=O)C(=O)CF RRYOTPCFMILDDZ-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- FOFLKNIFGIIGBK-UHFFFAOYSA-N 3-fluoro-2-oxopropanoic acid;hydrate Chemical compound O.OC(=O)C(=O)CF FOFLKNIFGIIGBK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims 2
- 229910003002 lithium salt Inorganic materials 0.000 claims 2
- 159000000002 lithium salts Chemical class 0.000 claims 2
- 230000000087 stabilizing effect Effects 0.000 claims 2
- AQVIWPOYCZKUAH-UHFFFAOYSA-N 2-amino-3-fluoro-2-hydroxypropanoic acid Chemical compound FCC(O)(N)C(O)=O AQVIWPOYCZKUAH-UHFFFAOYSA-N 0.000 claims 1
- NNUPCDRECHRJDC-UHFFFAOYSA-N 3-fluoro-2-iminopropanoic acid;hydrate Chemical compound O.OC(=O)C(=N)CF NNUPCDRECHRJDC-UHFFFAOYSA-N 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 abstract description 6
- UYTSRQMXRROFPU-LIIDHCAMSA-N (2s)-2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FC[C@](N)([2H])C(O)=O UYTSRQMXRROFPU-LIIDHCAMSA-N 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 244000052616 bacterial pathogen Species 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 238000006722 reduction reaction Methods 0.000 description 19
- 150000002466 imines Chemical class 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 10
- 229940076788 pyruvate Drugs 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000011067 equilibration Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DHALQLNIDMSKHU-UHFFFAOYSA-N 2-(fluoroamino)propanoic acid Chemical compound FNC(C)C(O)=O DHALQLNIDMSKHU-UHFFFAOYSA-N 0.000 description 2
- RLRSEGOXKMMOLT-UHFFFAOYSA-N 3-fluoro-2,2-dihydroxypropanoic acid Chemical compound OC(=O)C(O)(O)CF RLRSEGOXKMMOLT-UHFFFAOYSA-N 0.000 description 2
- RPFXMKLCYJSYDE-UHFFFAOYSA-N 3-fluoropropanoic acid Chemical compound OC(=O)CCF RPFXMKLCYJSYDE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DHALQLNIDMSKHU-REOHCLBHSA-N (2s)-2-(fluoroamino)propanoic acid Chemical compound FN[C@@H](C)C(O)=O DHALQLNIDMSKHU-REOHCLBHSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- UYTSRQMXRROFPU-UHFFFAOYSA-N 2-azaniumyl-3-fluoropropanoate Chemical compound FCC(N)C(O)=O UYTSRQMXRROFPU-UHFFFAOYSA-N 0.000 description 1
- UYIAUFVPRSSBGY-VMNATFBRSA-N 2-deuterio-3-fluoro-2-hydroxypropanoic acid Chemical compound FCC(O)([2H])C(O)=O UYIAUFVPRSSBGY-VMNATFBRSA-N 0.000 description 1
- ATIQEBQNQRNMEW-UHFFFAOYSA-N 2-fluoro-2-hydroxypropanoic acid Chemical compound CC(O)(F)C(O)=O ATIQEBQNQRNMEW-UHFFFAOYSA-N 0.000 description 1
- BLKAHDBNTYNLJN-UHFFFAOYSA-N 2-oxopropanoic acid;hydrate Chemical compound O.CC(=O)C(O)=O BLKAHDBNTYNLJN-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 229910013596 LiOH—H2O Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- APJSJVCWIQYDRG-UHFFFAOYSA-N diethyl 2-fluoro-3-oxobutanedioate;sodium Chemical compound [Na].CCOC(=O)C(F)C(=O)C(=O)OCC APJSJVCWIQYDRG-UHFFFAOYSA-N 0.000 description 1
- 229950010030 dl-alanine Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- WHXSMMKQMYFTQS-BKFZFHPZSA-N lithium-12 Chemical compound [12Li] WHXSMMKQMYFTQS-BKFZFHPZSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- POLUNJULUSSGMY-UHFFFAOYSA-M sodium;2-amino-3-fluoro-2-hydroxypropanoate Chemical compound [Na+].FCC(O)(N)C([O-])=O POLUNJULUSSGMY-UHFFFAOYSA-M 0.000 description 1
- YEXRRCHQJDSEJI-UHFFFAOYSA-M sodium;3-fluoro-2-oxopropanoate Chemical compound [Na+].[O-]C(=O)C(=O)CF YEXRRCHQJDSEJI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- 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
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Oncology (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)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/522,185 US3972921A (en) | 1974-11-08 | 1974-11-08 | Synthesis of racemic 2-deutero-3-fluoro-alanine and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053697A true CA1053697A (en) | 1979-05-01 |
Family
ID=24079796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA238,618A Expired CA1053697A (en) | 1974-11-08 | 1975-10-27 | Synthesis of racemic 2-deutero-3-fluoro-alanine and its salts, and intermediates therefor |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3972921A (en, 2012) |
| JP (1) | JPS5926614B2 (en, 2012) |
| AR (1) | AR208722A1 (en, 2012) |
| AT (1) | AT344136B (en, 2012) |
| BE (1) | BE835358A (en, 2012) |
| CA (1) | CA1053697A (en, 2012) |
| CH (1) | CH622772A5 (en, 2012) |
| CS (1) | CS199501B2 (en, 2012) |
| DD (1) | DD125839A5 (en, 2012) |
| DE (1) | DE2550121C2 (en, 2012) |
| DK (1) | DK474375A (en, 2012) |
| ES (1) | ES442154A1 (en, 2012) |
| FI (1) | FI752919A7 (en, 2012) |
| FR (1) | FR2290418A1 (en, 2012) |
| GB (1) | GB1480886A (en, 2012) |
| HU (1) | HU172273B (en, 2012) |
| IE (1) | IE42060B1 (en, 2012) |
| IT (1) | IT1048054B (en, 2012) |
| LU (1) | LU73734A1 (en, 2012) |
| NL (1) | NL7512383A (en, 2012) |
| NO (1) | NO147671C (en, 2012) |
| PL (1) | PL102608B1 (en, 2012) |
| SE (1) | SE7511734L (en, 2012) |
| SU (1) | SU626689A3 (en, 2012) |
| YU (1) | YU39750B (en, 2012) |
| ZA (1) | ZA757012B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028405A (en) * | 1974-10-15 | 1977-06-07 | Merck & Co., Inc. | Fluorinated amino acids |
| US4049708A (en) * | 1976-03-04 | 1977-09-20 | Merck & Co., Inc. | Fluorodesulfurization of alkyl mercaptans or alkyl dithianes |
| NZ194348A (en) * | 1979-07-26 | 1982-09-14 | Merrell Toraude & Co | Fluorinated methyl-beta-alanine derivatives and pharmaceutical compositions |
| JPS56113733A (en) * | 1979-12-29 | 1981-09-07 | Daikin Ind Ltd | 3-substituted-3-fluoropyruvic acid, its ester, salt and preparation thereof |
| US4582931A (en) * | 1984-12-24 | 1986-04-15 | Merck & Co., Inc. | Preparation of 2-Deutero-D-serine |
| US5254730A (en) * | 1992-01-14 | 1993-10-19 | Kilgore James L | Production of amino acids and amino acid derivatives bearing isotopic hydrogen labels |
| FR2707309B1 (fr) * | 1993-07-09 | 1995-08-11 | Trefileurope France Sa | Câble de levage. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610212A (en) * | 1950-04-24 | 1952-09-09 | Gen Mills Inc | Synthesis of amino acids |
| US2839547A (en) * | 1955-07-30 | 1958-06-17 | Inventa Ag | Process for the production of aminocarboxylic acids |
| JPS4936389B1 (en, 2012) * | 1969-03-03 | 1974-09-30 | ||
| US3585361A (en) * | 1969-06-18 | 1971-06-15 | Nordson Corp | Supply system for heating and dispensing molten thermoplastic material |
| JPS4841007B1 (en, 2012) * | 1970-10-22 | 1973-12-04 | ||
| JPS5225415B2 (en, 2012) * | 1972-01-17 | 1977-07-07 | ||
| JPS4935435A (en, 2012) * | 1972-08-09 | 1974-04-02 |
-
1974
- 1974-11-08 US US05/522,185 patent/US3972921A/en not_active Expired - Lifetime
-
1975
- 1975-10-20 SE SE7511734A patent/SE7511734L/xx unknown
- 1975-10-20 FI FI752919A patent/FI752919A7/fi not_active Application Discontinuation
- 1975-10-22 NL NL7512383A patent/NL7512383A/xx not_active Application Discontinuation
- 1975-10-22 DK DK474375A patent/DK474375A/da not_active Application Discontinuation
- 1975-10-23 NO NO753561A patent/NO147671C/no unknown
- 1975-10-27 YU YU2722/75A patent/YU39750B/xx unknown
- 1975-10-27 CA CA238,618A patent/CA1053697A/en not_active Expired
- 1975-10-27 GB GB44182/75A patent/GB1480886A/en not_active Expired
- 1975-10-28 ES ES442154A patent/ES442154A1/es not_active Expired
- 1975-10-28 AR AR260981A patent/AR208722A1/es active
- 1975-10-31 IT IT52036/75A patent/IT1048054B/it active
- 1975-10-31 SU SU752185056A patent/SU626689A3/ru active
- 1975-10-31 HU HU75ME00001914A patent/HU172273B/hu unknown
- 1975-11-04 CS CS757421A patent/CS199501B2/cs unknown
- 1975-11-04 AT AT838775A patent/AT344136B/de not_active IP Right Cessation
- 1975-11-05 FR FR7533779A patent/FR2290418A1/fr active Granted
- 1975-11-05 IE IE2407/75A patent/IE42060B1/en unknown
- 1975-11-05 DD DD189260A patent/DD125839A5/xx unknown
- 1975-11-06 PL PL1975184521A patent/PL102608B1/pl unknown
- 1975-11-06 LU LU73734A patent/LU73734A1/xx unknown
- 1975-11-06 CH CH1435875A patent/CH622772A5/de not_active IP Right Cessation
- 1975-11-07 DE DE2550121A patent/DE2550121C2/de not_active Expired
- 1975-11-07 JP JP50133150A patent/JPS5926614B2/ja not_active Expired
- 1975-11-07 BE BE161682A patent/BE835358A/xx not_active IP Right Cessation
- 1975-11-07 ZA ZA757012A patent/ZA757012B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7512383A (nl) | 1976-05-11 |
| CH622772A5 (en, 2012) | 1981-04-30 |
| IE42060L (en) | 1976-05-08 |
| AT344136B (de) | 1978-07-10 |
| FI752919A7 (en, 2012) | 1976-05-09 |
| FR2290418B1 (en, 2012) | 1979-01-05 |
| DD125839A5 (en, 2012) | 1977-05-25 |
| YU39750B (en) | 1985-04-30 |
| NO753561L (en, 2012) | 1976-05-11 |
| SU626689A3 (ru) | 1978-09-30 |
| NO147671B (no) | 1983-02-14 |
| DK474375A (da) | 1976-05-09 |
| BE835358A (fr) | 1976-05-07 |
| GB1480886A (en) | 1977-07-27 |
| IT1048054B (it) | 1980-11-20 |
| FR2290418A1 (fr) | 1976-06-04 |
| CS199501B2 (en) | 1980-07-31 |
| ATA838775A (de) | 1977-11-15 |
| JPS5170722A (en) | 1976-06-18 |
| DE2550121A1 (de) | 1976-05-20 |
| LU73734A1 (en, 2012) | 1976-09-06 |
| US3972921A (en) | 1976-08-03 |
| PL102608B1 (pl) | 1979-04-30 |
| JPS5926614B2 (ja) | 1984-06-29 |
| AR208722A1 (es) | 1977-02-28 |
| IE42060B1 (en) | 1980-05-21 |
| HU172273B (hu) | 1978-07-28 |
| ES442154A1 (es) | 1977-07-01 |
| ZA757012B (en) | 1977-06-29 |
| NO147671C (no) | 1983-05-25 |
| AU8605675A (en) | 1977-05-05 |
| SE7511734L (sv) | 1976-05-10 |
| DE2550121C2 (de) | 1984-08-16 |
| YU272275A (en) | 1982-02-28 |
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