GB1153464A - Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparation - Google Patents
Amino-Fluoro-Aliphatic Dicarboxylic Acids and a process for their preparationInfo
- 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
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.
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)
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 |
-
1965
- 1965-08-25 GB GB3653865A patent/GB1153464A/en not_active Expired
Cited By (6)
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 |