GB1153464A - Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparation - Google Patents

Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparation

Info

Publication number
GB1153464A
GB1153464A GB3653865A GB3653865A GB1153464A GB 1153464 A GB1153464 A GB 1153464A GB 3653865 A GB3653865 A GB 3653865A GB 3653865 A GB3653865 A GB 3653865A GB 1153464 A GB1153464 A GB 1153464A
Authority
GB
United Kingdom
Prior art keywords
acid
fluoropimelic
fluoro
cooh
amino
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
GB3653865A
Inventor
Bruno Cavalleri
Elvio Bellasio
Emilio Testa
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.)
Gruppo Lepetit SpA
Original Assignee
Gruppo Lepetit SpA
Lepetit SpA
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 Gruppo Lepetit SpA, Lepetit SpA filed Critical Gruppo Lepetit SpA
Priority to GB3653865A priority Critical patent/GB1153464A/en
Publication of GB1153464A publication Critical patent/GB1153464A/en
Expired legal-status Critical Current

Links

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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/32—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Indole Compounds (AREA)

Abstract

1,153,464. Amino-fluoro-aliphatic dicarboxylic acids. GRUPPO LEPETIT S.p.A. 7 July, 1966 [25 Aug., 1965], No. 36538/65. Heading C2C. Novel compounds of the formula (I) COOH-CHNH 2 -(CH 2 )m-CHF- (CH 2 ) n -(CHNH 2 ) p -COOH wherein m is an integer from 1 to 4 inclusive, n is 0, 1 or 2 and p is 0 or 1, but when p is 0, n is also 0, are obtained by treating a fluorinated dicarboxylic acid HOOC.CH 2 (CH 2 ) m .CHF(CH 2 ) x COOH, where x is 0, 1, 2 or 3, with bromine whereby a bromine atom is substituted for a hydrogen atom in a position adjacent to a carboxy group and substituting the bromine atom with an amino group by the action of an aminating agent, such as ammonia or potassium phthalimide. The compounds are useful antimetabolites. The following intermediates are also described: α-Fluoropimelic acid dichloride is obtained by refluxing α-fluoropimelic acid with SOCl 2 , and the dichloride is reacted with Br 2 in the presence of strong light at 90‹ C. to form α-fluoro-α<SP>1</SP>-bromopimelic acid. γ-Nitropimelic acid dimethyl ester is obtained by reacting together nitromethane, triethylamine and methyl acrylate. The ester is hydrolysed with conc.HCl to form γ-nitropimelic acid which is hydrogenated to γ-aminopimelic acid. The latter is heated to melting point under nitrogen and kept at 180-200‹ for 1 hour, and 2-pyrrolidone-5- propionic acid is obtained. This product is dissolved in aqueous HF and treated with NaNO 2 with heating and γ - fluoropimelic acid is obtained. The latter is converted by the above method successively to α,α<SP>1</SP>-dibromo-γ-fluoropimelic acid diethyl ester and α,α<SP>1</SP>-diphthalimido- γ-fluoropimelic acid diethyl ester.
GB3653865A 1965-08-25 1965-08-25 Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparation Expired GB1153464A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3653865A GB1153464A (en) 1965-08-25 1965-08-25 Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3653865A GB1153464A (en) 1965-08-25 1965-08-25 Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparation

Publications (1)

Publication Number Publication Date
GB1153464A true GB1153464A (en) 1969-05-29

Family

ID=10389070

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3653865A Expired GB1153464A (en) 1965-08-25 1965-08-25 Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparation

Country Status (1)

Country Link
GB (1) GB1153464A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989010348A1 (en) * 1988-04-19 1989-11-02 Synpharm Ltd Fatty amino acids, and homo- and hetero-oligomers and conjugates thereof
DE4334873A1 (en) * 1993-10-13 1995-04-20 Nycomed Arzneimittel Gmbh Asymmetrically substituted diaminodicarboxylic acid derivatives and process for their preparation
WO2017151938A1 (en) * 2016-03-04 2017-09-08 University Of Pittsburgh- Of The Commonwealth System Of Higher Education Prevention, treatment and reversal of disease using therapeutically effective amounts of dicarboxylic acid compounds

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989010348A1 (en) * 1988-04-19 1989-11-02 Synpharm Ltd Fatty amino acids, and homo- and hetero-oligomers and conjugates thereof
DE4334873A1 (en) * 1993-10-13 1995-04-20 Nycomed Arzneimittel Gmbh Asymmetrically substituted diaminodicarboxylic acid derivatives and process for their preparation
WO2017151938A1 (en) * 2016-03-04 2017-09-08 University Of Pittsburgh- Of The Commonwealth System Of Higher Education Prevention, treatment and reversal of disease using therapeutically effective amounts of dicarboxylic acid compounds
CN109071405A (en) * 2016-03-04 2018-12-21 高等教育联邦系统-匹兹堡大学 It is prevented, treated using the dicarboxylic acid compound of therapeutically effective amount and reverse disease
US10751310B2 (en) 2016-03-04 2020-08-25 University of Pittsburgh—of the Commonwealth System of Higher Education Prevention, treatment and reversal of disease using therapeutically effective amounts of dicarboxylic acid compounds
US11642325B2 (en) 2016-03-04 2023-05-09 University of Pittsburgh—of the Commonwealth System of Higher Education Prevention, treatment and reversal of disease using therapeutically effective amounts of dicarboxylic acid compounds

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees