GB1367674A - 3-fluoroalanines - Google Patents

3-fluoroalanines

Info

Publication number
GB1367674A
GB1367674A GB3488671A GB3488671A GB1367674A GB 1367674 A GB1367674 A GB 1367674A GB 3488671 A GB3488671 A GB 3488671A GB 3488671 A GB3488671 A GB 3488671A GB 1367674 A GB1367674 A GB 1367674A
Authority
GB
United Kingdom
Prior art keywords
alanine
fluoro
deacetylation
acetylation
sequence
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
Application number
GB3488671A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1367674A publication Critical patent/GB1367674A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms
    • C07C53/21—Acids containing three or more carbon atoms containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/38—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

Abstract

1367674 3-Fluoro-alanines MERCK & CO Inc 26 July 1971 [3 Aug 1970 3 June 1971] 34886/71 Heading C2C Novel D-isomers of the formula wherein each of x and y is 1 or 2 (thus each of x and y represent hydrogen or deuterium) and pharmaceutically acceptable salt thereof are prepared: (a) by the action of fluoroxyperfluoroalkane or fluoroxypentafluorosulphur on D- alanine under free radical initiation followed by chromatographic separation of the product to isolate 3-fluoro-alanine; (b) by the action of alanine racemase (an enzyme preparation from Staphylococcus aureus) in <SP>2</SP>H 2 O on L-alanine to incorporate deuterium into the alpha-position of D-alanine (the deuterated D-alanine is separated by the sequence N-acetylation, chromatographic separation and deacetylation), the thus produced 2-<SP>2</SP>H-D-alanine in subjected to the procedure under (a) above to form 2-<SP>2</SP>H-3-fluoro-D- alanine; and (c) 3,3,3-<SP>2</SP>H-D-alanine (obtained by the resolution of perdeutero alanine racemate using the sequence N-acetylation and deacetylation) is fluorinated as in (a) to form 3,3,2-<SP>2</SP>H- 3-fluoro-D-alanine. Pharmaceutical compositions and disinfectant compositions having anti-bacterial activity comprise the above novel compounds and a carrier therefore.
GB3488671A 1970-08-03 1971-07-26 3-fluoroalanines Expired GB1367674A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6064570A 1970-08-03 1970-08-03
US14981471A 1971-06-03 1971-06-03

Publications (1)

Publication Number Publication Date
GB1367674A true GB1367674A (en) 1974-09-18

Family

ID=26740157

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3488671A Expired GB1367674A (en) 1970-08-03 1971-07-26 3-fluoroalanines

Country Status (13)

Country Link
JP (1) JPS565217B1 (en)
AU (1) AU468229B2 (en)
BE (1) BE770888A (en)
CA (1) CA956646A (en)
CH (1) CH563961A5 (en)
DE (1) DE2136067C3 (en)
FR (1) FR2101198B1 (en)
GB (1) GB1367674A (en)
HK (1) HK86379A (en)
IE (1) IE35489B1 (en)
IL (1) IL37429A (en)
IT (1) IT1061753B (en)
NL (1) NL174248C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985004395A1 (en) * 1984-03-23 1985-10-10 Commonwealth Scientific And Industrial Research Or Deuterated compounds
WO2007109080A3 (en) * 2006-03-16 2007-11-15 Vertex Pharma Deuterated hepatitis c protease inhibitors
EP2295401A3 (en) * 2006-03-16 2012-07-25 Vertex Pharmaceuticals Incorporated Deuterated hepatitis C protease inhibitors
RU2465264C2 (en) * 2006-03-16 2012-10-27 Вертекс Фармасьютикалз Инкорпорейтед Deuterated hepatitis c protease inhibitors

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985004395A1 (en) * 1984-03-23 1985-10-10 Commonwealth Scientific And Industrial Research Or Deuterated compounds
WO2007109080A3 (en) * 2006-03-16 2007-11-15 Vertex Pharma Deuterated hepatitis c protease inhibitors
EP2295401A3 (en) * 2006-03-16 2012-07-25 Vertex Pharmaceuticals Incorporated Deuterated hepatitis C protease inhibitors
US8247532B2 (en) 2006-03-16 2012-08-21 Vertex Pharmaceuticals Incorporated Deuterated hepatitis C protease inhibitors
RU2465264C2 (en) * 2006-03-16 2012-10-27 Вертекс Фармасьютикалз Инкорпорейтед Deuterated hepatitis c protease inhibitors
AU2007227544B2 (en) * 2006-03-16 2012-11-01 Vertex Pharmaceuticals Incorporated Deuterated hepatitis C protease inhibitors

Also Published As

Publication number Publication date
HK86379A (en) 1979-12-28
NL7109947A (en) 1972-02-07
DE2136067B2 (en) 1980-01-17
NL174248C (en) 1984-05-16
IL37429A (en) 1975-05-22
NL174248B (en) 1983-12-16
FR2101198B1 (en) 1975-08-01
AU468229B2 (en) 1976-01-08
IT1061753B (en) 1983-04-30
DE2136067A1 (en) 1972-02-10
DE2136067C3 (en) 1980-09-11
FR2101198A1 (en) 1972-03-31
CH563961A5 (en) 1975-07-15
IL37429A0 (en) 1971-11-29
CA956646A (en) 1974-10-22
BE770888A (en) 1972-02-03
IE35489B1 (en) 1976-03-03
JPS565217B1 (en) 1981-02-04
IE35489L (en) 1972-02-03
AU3146471A (en) 1973-01-25

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE20 Patent expired after termination of 20 years