Quaternary salts of dibenzo[1,4]diazepinones, pyrido-[1,4]benzodiazepinones, pyrido[1,5]benzodiazepinones with antiulcer, antisecretory, spasmolytic and antimusarinic activities

• US 4,594,190 A
• Filed: 05/09/1984
• Issued: 06/10/1986
• Est. Priority Date: 05/17/1983
• Status: Expired due to Term

• Current Assignee: Dompe Farmaceutici S.p.A (Sergio Dompé SRL)
• Original Assignee: Dompe Farmaceutici S.p.A (Sergio Dompé SRL)
• Inventors: Tonon, Giancarlo, Giani, Roberto, Parini, Ettore
• Primary Examiner(s): Daus, Donald G.
• Assistant Examiner(s): TSANG, CECILIA J
• Application Number:
  US06/609,102
• Time in Patent Office: 762 Days
• Field of Search: 260/243.3, 260/239 BD, 260/239 DD, 260/244.4, 260/245.7, 260/239.3 R, 260/239.3 T, 514/220
• US Class Current: 514/220
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 21/02 Muscle relaxants, e.g. for tetanus or cramps
• CPC Class Codes: A61P 25/02 for peripheral neuropathies
• CPC Class Codes: C07D 243/38 [b, e]- or [b, f]-condensed with six-membered rings
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

Quaternary salts of 11-acyl derivatives of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one and 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one are described.

Said quaternary salts are endowed with antiulcer, antisecretory, spasmolytic and antimuscarinic activity.

Claims

1. A compound of formula I ##STR39## wherein Y is N or CH,

A is NH,

B is C═

O or C═

S or vice versa,

R is a group of formula ##STR40## wherein R₁ is hydrogen or C₁ -C₄ alkyl and n is 1 or 2, M represents one of the following groups ##STR41## wherein X^- is the anion of an halogenidric acid, R₂, R₃ and R₄, which may be the same or different, represent linear or branched C₁ -C₄ alkyl, C₃ -C₇ cycloalkyl, pivaloyloxymethyl, benzyl or R₂ has one of said meanings and R₃ and R₄ together form one of the following cyclic groups ##STR42## wherein R₇ is hydrogen or methyl and X.sup.⊖

has the above defined meaning, or

R₂, R₃ and R₄, taken together, form one of the following groups;

##STR43## R₅ and R₆, which can be the same or different, represent methyl, ethyl, benzyl, 3,4-methylenedioxybenzyl or pivaloyloxymethyl.

2. A compound according to claim 1 wherein Y is N, A is NH, B is C═

O.

3. A compound according to claim 1 wherein Y is N, A is C═

O and B is NH.

4. A compound according to claim 1 wherein Y is CH, A is C═

O and B is NH.

5. A compound according to claim 1 wherein n is 1, R₁ is hydrogen, M is a group of formula ##STR44## at least one of the R₂, R₃ or R₄ groups being methyl.

6. A compound according to claim 5 wherein R₂ is methyl and R₃ and R₄ taken together form one of the following cyclic groups ##STR45## wherein R₇ and X^- have the above defined meanings.

7. A compound according to claim 1 wherein R₂, R₃ and R₄ taken together form one of the following groups:

##STR46##

8. A compound according to claim 1 wherein M is a group ##STR47## wherein R₅ and R₆, which may be the same or different, are methyl, ethyl, benzyl, 3,4-methylenedioxybenzyl, pivaloyloxymethyl.

9. A pharmaceutical composition having antiscretoric, antiulcerogenic, spasmolytic and antimuscarinic activities containing as the principal active ingredient an antisecretoric, antiulcerogenic, spasmolytic and antimuscarinic effective amount of a compound according to claim 1 in admixture with a pharmaceutically acceptable carrier.