FR2184511A1 - 4,5,7-Trimethyl-8-sulphamoyl coumarins - with oral hypoglycemic activity and low toxicity - Google Patents

4,5,7-Trimethyl-8-sulphamoyl coumarins - with oral hypoglycemic activity and low toxicity

Info

Publication number
FR2184511A1
FR2184511A1 FR7218025A FR7218025A FR2184511A1 FR 2184511 A1 FR2184511 A1 FR 2184511A1 FR 7218025 A FR7218025 A FR 7218025A FR 7218025 A FR7218025 A FR 7218025A FR 2184511 A1 FR2184511 A1 FR 2184511A1
Authority
FR
France
Prior art keywords
degrees
stage
sulphamoyl
coumarins
trimethyl
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.)
Granted
Application number
FR7218025A
Other languages
French (fr)
Other versions
FR2184511B1 (en
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.)
Synthelabo SA
Original Assignee
Synthelabo SA
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 Synthelabo SA filed Critical Synthelabo SA
Priority to FR7218025A priority Critical patent/FR2184511A1/en
Publication of FR2184511A1 publication Critical patent/FR2184511A1/en
Application granted granted Critical
Publication of FR2184511B1 publication Critical patent/FR2184511B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

(A) Compounds of formula (I) are new: where R,R' are same or different H, alkyl (C1-C5), or phenyl opt. substd. by one or more halogen, NH2, NO2 or SO2NH2; or NRR' is a satd. heterocycle (5-7 membered) opt. contg. a second heteroatom (O, N or S). (B) The intermediates (III) are also new (see "Preparation"). Oral hypoglycaemic agents for use in human and veterinary medicine. Stage 1 is pref. performed at 70-100 degrees C in conc. H2SO4; stage 2 at 100 to 150 degrees C in absence of solvent; stage 3 pref. at -5 to +25 degrees C in a suitable solvent. PHARMACOLOGY The most active compounds have a similar hypoglycaemic activity to that of chlorpropamide at 50 mg/kg. orally in mice but they are much less toxic (no deaths at 10g/kg; chlorpropamide LD50 is 1.1 g/kg.) Two compounds have slight diuretic activity.
FR7218025A 1972-05-19 1972-05-19 4,5,7-Trimethyl-8-sulphamoyl coumarins - with oral hypoglycemic activity and low toxicity Granted FR2184511A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7218025A FR2184511A1 (en) 1972-05-19 1972-05-19 4,5,7-Trimethyl-8-sulphamoyl coumarins - with oral hypoglycemic activity and low toxicity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7218025A FR2184511A1 (en) 1972-05-19 1972-05-19 4,5,7-Trimethyl-8-sulphamoyl coumarins - with oral hypoglycemic activity and low toxicity

Publications (2)

Publication Number Publication Date
FR2184511A1 true FR2184511A1 (en) 1973-12-28
FR2184511B1 FR2184511B1 (en) 1975-10-17

Family

ID=9098831

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7218025A Granted FR2184511A1 (en) 1972-05-19 1972-05-19 4,5,7-Trimethyl-8-sulphamoyl coumarins - with oral hypoglycemic activity and low toxicity

Country Status (1)

Country Link
FR (1) FR2184511A1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527768A (en) * 1967-11-24 1970-09-08 Monsanto Co Sulfonamido coumarin compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527768A (en) * 1967-11-24 1970-09-08 Monsanto Co Sulfonamido coumarin compounds

Also Published As

Publication number Publication date
FR2184511B1 (en) 1975-10-17

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Legal Events

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ST Notification of lapse