GB1075300A - N-substituted-5-sulfamoyl-4-trifluoromethylanthranilic acids - Google Patents

N-substituted-5-sulfamoyl-4-trifluoromethylanthranilic acids

Info

Publication number
GB1075300A
GB1075300A GB2321066A GB2321066A GB1075300A GB 1075300 A GB1075300 A GB 1075300A GB 2321066 A GB2321066 A GB 2321066A GB 2321066 A GB2321066 A GB 2321066A GB 1075300 A GB1075300 A GB 1075300A
Authority
GB
United Kingdom
Prior art keywords
acid
sulphamoyl
halo
give
carbon atoms
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
GB2321066A
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories Ltd
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 Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB1075300A publication Critical patent/GB1075300A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Abstract

The invention comprises compounds having the formula <FORM:1075300/C2/1> wherein R1 is a hydrogen atom or a C1- 6 alkyl group, R2 is furylmethylamino, thenylamino, benzylamino or dibenzylamino and carboxylic acid salts thereof. The novel compounds may be made by nitrating a 2-halo-4-trifluoromethylbenzoic acid to give a 2-halo-5-nitro-4-trifluoromethylbenzoic acid, reducing this to a 5-amino-2 - halo - 4 - trifluoromethylbenzoic acid, treating this product with conc. HCl and sodium nitrite followed by SO2 in acetic acid containing cuprous chloride, treating the resulting 4-chlorosulphonyl compound with ammonium hydroxide or an alkylamine to give a 2-halo-5 - sulphamoyl - 4 - trifluoromethyl benzoic acid and reacting this with R2H to give the desired product. Alternatively, a 2-bromo-5-trifluoromethylanilin is converted to 4-trifluoromethylanthranilonitrile. This benzonitrile may be reacted with chlorosulphonic acid and ammonium hydroxide or alkylamine to give 5 - sulphamoyl - 4 - trifluoromethylanthranilonitrile which is hydrolysed to the corresponding anthranilic acid. Alternatively, the benzonitrile may be hydrolysed first and then sulphamoylated. The 5-sulphamoyl-4-trifluoromethylanthranilic acid is reacted with RCHO in which R is phenyl, furyl or thienyl and the resulting Schiff base is reduced to give the desired N - substituted - 5 - sulphamoyl -4 -trifluoromethylanthranilic acid.ALSO:Pharmaceutical compositions having diuretic activity comprise a pharmaceutical carrier in association with an N-substituted-5-sulphamoyl - 4 - trifluoromethylanthranilic acid of the formula: <FORM:1075300/A5-A6/1> where R1 is hydrogen or alkyl having 1 to 6 carbon atoms and R2 is furylmethylamino thenylamino, benzylamino or dibenzlamino, or a carboxylic acid salt thereof, with or without a 2,4,7-triamino-6-phenyl pteridine of the formula: <FORM:1075300/A5-A6/2> where R3 is hydrogen or alkyl having 1 to 3 carbon atoms and R4 is hydrogen, alkyl having 1 to 3 carbon atoms, trifluoromethyl, halo or alkoxy having 1 to 3 carbon atoms. With a solid carrier, the composition may be in the form of tablets, hard gelatin capsules, troches or lozenges. With a liquid carrier, the composition may be in the form of a soft gelatin capule or a liquid suspension. The compositions may be administered orally or parentally
GB2321066A 1965-06-14 1966-05-24 N-substituted-5-sulfamoyl-4-trifluoromethylanthranilic acids Expired GB1075300A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US46389965A 1965-06-14 1965-06-14

Publications (1)

Publication Number Publication Date
GB1075300A true GB1075300A (en) 1967-07-12

Family

ID=23841734

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2321066A Expired GB1075300A (en) 1965-06-14 1966-05-24 N-substituted-5-sulfamoyl-4-trifluoromethylanthranilic acids

Country Status (2)

Country Link
DE (1) DE1543858A1 (en)
GB (1) GB1075300A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2321485A1 (en) * 1975-08-21 1977-03-18 Bayer Ag PROCESS FOR THE PRODUCTION OF TRIFLUOROMETHYL-AMINOBENZONITRILES
FR2609288A1 (en) * 1986-12-23 1988-07-08 Central Glass Co Ltd PROCESS FOR THE PREPARATION OF 4-TRIFLUOROMETHYL-3-NITROBENZOIC ACID THROUGH A NEW NITROBENZENE DERIVATIVE

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2321485A1 (en) * 1975-08-21 1977-03-18 Bayer Ag PROCESS FOR THE PRODUCTION OF TRIFLUOROMETHYL-AMINOBENZONITRILES
FR2609288A1 (en) * 1986-12-23 1988-07-08 Central Glass Co Ltd PROCESS FOR THE PREPARATION OF 4-TRIFLUOROMETHYL-3-NITROBENZOIC ACID THROUGH A NEW NITROBENZENE DERIVATIVE

Also Published As

Publication number Publication date
DE1543858A1 (en) 1970-01-02

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