4-amidino pyrano (3,2-c) pyridine derivatives, and pharmaceutical compositions containing them

• US 5,185,345 A
• Filed: 03/12/1992
• Issued: 02/09/1993
• Est. Priority Date: 11/06/1989
• Status: Expired due to Fees

• Current Assignee: Sanofi S.A. (Sanofi-Synthélabo SA)
• Original Assignee: Sanofi
• Inventors: Gautier, Patrick, Garcia, Georges, Roux, Richard, Nisato, Dino
• Primary Examiner(s): Fan, Jane T.
• Application Number:
  US07/850,994
• Time in Patent Office: 334 Days
• Field of Search: 514/302, 546/115, 546/116
• US Class Current: 514/302
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 491/04 Ortho-condensed systems

Abstract

The present invention deals with 4-amidino chroman and 4-amidino pyrano (3,2-c) pyridine derivatives, a process for their preparation and pharmaceutical compositions containing them. Said derivatives have antihypertensive and antiarythmic activities. They respond to formula ##STR1## in which: A+B═--CH═CH--CH═N-- ou --CH═CR₄ --CR₅ ═CH--; X═N,N→O, C--Z;

R₁ ═H, CN, NO₂, C₁ -C₄, alkyl, OH, C₁ -C₄ alkoxy, CF₃ CO--, CH₃ --SO₂ --, ρ--SO₂ --;

R₂ ═H;

R₃ ═OH ou OCOCH₃ ou R₂ +R₃ ═double bond.

Claims

1. A compound of formula (I):

##STR10## in which;

A and B are linked together between N and C═

NR₁ and represent --CH═

CR₄ -CR₅ ═

CH--, wherein one of the substituents R₄ or R₅ denotes hydrogen and the other substituent is selected from the group consisting of hydrogen, halogen, nitro and C₁ -C₄ alkyl;

X represents a nitrogen atom or a N-oxide group;

R₁ represents hydrogen, cyano, nitro, C₁ -C₄ alkyl, hydroxyl, C₁ -C₄ alkoxy, trifluoroacetyl, methanesulfonyl, benzenesulfonyl, benzenesulfonyl unsubstituted or substituted on the phenyl by methyl, halogen or trifluoromethyl;

R₂ represents hydrogen; and

R₃ represents hydroxyl or acetyloxy or R₂ and R₃ together form a bond.

2. A pharmaceutical composition having an antihypertensive and/or antiarrhythmic effect which comprises an effective amount of one compound of formula (I) according to claim 1 in admixture with a pharmaceutically acceptable excipient.

3. A pharmaceutical composition according to claim 2 wherein the effective amount is 0.01 to 2 mg of active ingredient per dosage unit.

4. A method of treating a human or animal subject suffering from hypertension or arrhythmia comprising administering a pharmaceutically effective amount of a compound according to claim 2 to the human or animal subject.

5. A method according to claim 4, wherein the compound is administered orally, buccally, sublingually, subcutaneously, intramuscularly, intravenously or rectally.

6. A method according to claim 5, wherein the effective amount is 0.01 to 2 mg per kg of body weight administered 1 to 5 times per day.