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GB1191015A - Iodinated Imido-Benzoic Acids - Google Patents

Iodinated Imido-Benzoic Acids

Info

Publication number
GB1191015A
GB1191015A GB21897/67A GB2189767A GB1191015A GB 1191015 A GB1191015 A GB 1191015A GB 21897/67 A GB21897/67 A GB 21897/67A GB 2189767 A GB2189767 A GB 2189767A GB 1191015 A GB1191015 A GB 1191015A
Authority
GB
United Kingdom
Prior art keywords
compound
alkanoyl
general formula
carbon atoms
lower alkanoyl
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
GB21897/67A
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.)
STWB Inc
Original Assignee
Sterling Drug 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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB1191015A publication Critical patent/GB1191015A/en
Priority to US00109631A priority Critical patent/US3770820A/en
Priority to US05/478,052 priority patent/US4031088A/en
Priority to US05/733,298 priority patent/US4111937A/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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
    • 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • 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
    • C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—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 two 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,191,015. Iodophenyl imides; N-(3-carboxy- 5-nitro and amino-phenyl)-imides. STERLING DRUG Inc. 11 May, 1967 [17 May, 1966], No. 21897/67. Heading C2C. The invention comprises compounds of the general formula wherein Y is a lower alkylene group having from 2 to 6 carbon atoms such that 2 or 3 carbon atoms separate the carbonyl groups, or a 1,3-propylene group having from 2 to 4-carbon atoms wherein the 2-carbon atom is replaced by O, S, SO or SO 2 ; R is H, H 2 N, (lower alkanoyl)NH, (lower alkanoyl)N(lower alkyl), (lower alkoxy-lower alkanoyl)NH, (lower alkoxy-lower alkanoyl)N(lower alkyl), HOOC, (lower alkyl) NHCO, or HOOC-Y-CO-N-(lower alkyl) wherein Y is as defined above, and wherein "lower alkyl" and "lower alkoxy" are groups containing from 1 to 4 carbon atoms and "lower alkanyol" is a group containing from 1 to 6 carbon atoms, and the pharmaceutically acceptable salts thereof. The compounds may be prepared by the following methods: (a) when R is other than -NH 2 , (lower alkanoyl)NH- or (lower alkoxylower alkanoyl)NH-, by reaction of a compound of the general formula with an acid anhydride of the general formula wherein Y is as defined above or an acid chloride of the general formula wherein Y is a lower alkylene group as defined above; (b) when R is -NH 2 , (lower alkanoyl)- NH- or (lower alkoxy-lower alkanoyl)NH-, by reaction of 3-amino-5-nitrobenzoic acid with an anhydride as defined in method (a) above to give a compound of the general formula hydrogenating this compound to give a compound of the general formula reacting this compound with KICl 2 to give a compound of the invention wherein R is -NH 2 , and optionally, acylating this compound with an appropriate acid anhydride to give a compound of the invention wherein R is (lower alkanoyl)NH- or (lower alkoxy-lower alkanoyl)NH-; (c) when R is -N(CO) 2 Y and the Y groups are identical, by reacting 3,5-diamino-2,4,6-triiodobenzoic acid with at least 2 equivalents of an anhydride as defined in method (a) above; (d) when Y is a lower alkylene group interrupted by -SO- or -SO 2 -, by per-acid oxidation of the corresponding compounds containing an interrupting group -S-. The salts are obtained in conventional manner. The compounds of the invention in the form of their water-soluble salts are employed as X-ray contrast agents.
GB21897/67A 1966-05-17 1967-05-11 Iodinated Imido-Benzoic Acids Expired GB1191015A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US00109631A US3770820A (en) 1967-05-11 1971-01-25 Iodinated anilic acids
US05/478,052 US4031088A (en) 1967-05-11 1974-06-10 Iodinated anilic acids
US05/733,298 US4111937A (en) 1967-05-11 1976-10-18 Iodinated anilic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US55061466A 1966-05-17 1966-05-17

Publications (1)

Publication Number Publication Date
GB1191015A true GB1191015A (en) 1970-05-06

Family

ID=24197895

Family Applications (2)

Application Number Title Priority Date Filing Date
GB21897/67A Expired GB1191015A (en) 1966-05-17 1967-05-11 Iodinated Imido-Benzoic Acids
GB5739968A Expired GB1191016A (en) 1966-05-17 1967-05-11 Iodinated Carboxyacylamino-Benzoic Acids

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB5739968A Expired GB1191016A (en) 1966-05-17 1967-05-11 Iodinated Carboxyacylamino-Benzoic Acids

Country Status (3)

Country Link
FR (1) FR6447M (en)
GB (2) GB1191015A (en)
SE (1) SE316176B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374220A (en) 1968-09-18 1983-02-15 Raychem Corporation Imide flame retardants and compositions containing them
US4535170A (en) * 1968-09-18 1985-08-13 Raychem Corporation Flame retardants and compositions containing them
US4644066A (en) * 1968-09-18 1987-02-17 Raychem Corporation Flame retardants and compositions containing them
US5628980A (en) * 1989-11-29 1997-05-13 Bracco International B.V. Nonionic radiographic contrast agents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3745170A (en) * 1969-03-19 1973-07-10 Sumitomo Chemical Co Novel n-(3,5-dihalophenyl)-imide compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374220A (en) 1968-09-18 1983-02-15 Raychem Corporation Imide flame retardants and compositions containing them
US4535170A (en) * 1968-09-18 1985-08-13 Raychem Corporation Flame retardants and compositions containing them
US4644066A (en) * 1968-09-18 1987-02-17 Raychem Corporation Flame retardants and compositions containing them
US5628980A (en) * 1989-11-29 1997-05-13 Bracco International B.V. Nonionic radiographic contrast agents

Also Published As

Publication number Publication date
SE316176B (en) 1969-10-20
FR6447M (en) 1968-11-12
GB1191016A (en) 1970-05-06

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees