DE8259T1

DE8259T1 - New piperidylbenxime kUioUnon derivatives, process for their preparation and pharmaceutical preparations containing them

Info

Publication number: DE8259T1
Application number: DE1979400509
Authority: DE
Inventors: Jacques Croissy Seine; Dhainaut Alain Gennevilliers; Regnier Gilbert Chatenay-Malabry; Boulanger Michelle Marly-le-Roi Duhault (Frankreich)
Original assignee: Science Union et Cie Societe Francaise de Recherche Medicale, Suresnes (Frankreich)
Priority date: 1978-07-20
Filing date: 1979-07-19
Publication date: 1980-09-04

Claims

QQQ825S

Translation of the claims of the European patent application No. 79 4oo 5o9.o (publication number ooo8259)

Applicant: Science Union et Cie., Societe Fran? Aise de Recherche Medicale, 14, rue du VaI d'Or, F - 9215o Suresnes, France

Title: New Piperidylbenzimidazolinone Derivatives,

Process for their production and pharmaceutical preparations containing them

Claims

1 . Piperidylbenzimidazolinone derivatives e'er general Formula I.

-> π / - \ y

^! CH - CH - * ' ^{lv lI} - ^Z

OH

in the

R is a hydrogen atom, a hydroxyl group (OH-), a Hydroxymethyl group (HO-CH-), a methoxycarbonyl group (CH ^ -O-C-), a formamido group (H-CO-NH-),

^: . -J Il

5 57 / 00AC

an acetamido group (CH - CO-NH-), a mesylamino group (CH-SO-NH-), an oxalamino group (HOOC-CO-NH-), an ethoxalylamino group (CH OOC-CO-NH-), a carbamoy! group (, 7 "" N-CO-), an ureido group
( _πΙΙ N-CO-NH-) or a sulfamoylamino group

(,, N ^- SO -NH-),

where R 'and R "in these formulas are identical or
be of the same type and each hydrogen atoms or
Can represent alkyl groups with 1 to 5 carbon atoms,

T is a hydrogen atom, a halogen atom or an alkyl or alkoxy group each having 1 to 5 carbon atoms and

Z represents a hydrogen atom or a straight-chain or branched one Alkyl or alkenyl groups, each with 1 to

5 carbon atoms
mean.

2. The addition salts of the compounds of claim with suitable acids.

3. The salts according to claim 2, which are physiologically acceptable.

4. 1 - {/ 2- (3,4-Dihydroxyphenyl) -2-hydroxy7-ethyl} -4- (2-oxo-benζimidazοlin-1-yl) piperidine.

5. 1 - {/ 2- (4-Hydroxyphenyl) '- 2-hydroxy7-ethyl3r-.4- (2-

oxo-benzimidazoline-1-yl) piperidine.
'_:;'V. ^: - ■

6. 1 - {/ 2- (3,5-dihydroxyphenyl) -2-hydroxy7-ethyl} -4- (2-oxo-benzimidazolin-1-yl) -piperidine and its hydrochloride.

05 57 / OO4C

7. A process for the preparation of the compounds according to claim 1, characterized in that a haloacetophenone of the general formula II

CO - CH - X (II)CO - CH - X (II)

in the

X is a chlorine atom or a bromine atom, R is a hydrogen atom or an easily hydrolyzable

re or hydrogenolyzable protective group and R "a hydrogen atom, a hydroxyl group, an acetoxy group, a benzyloxy group, a hydroxymethyl group, an acetoxymethyl group, a benzyloxymethyl group, a methoxycarbonyl group (CH -0-C-),

J Il

a formamido group (H-CO-NH-), an acetamido group (CH-CO-NH-), a mesylamino group (CH-SO-NH-), an oxalamino group (HOOC-CO-NH-), an ethoxalylamino group (C ₃ H OOC-CO-NH-), a carbamoyl group (^, 'r ~ N-CO-), an ureido group (^,', ^ N-CO-NH-) or R - ■ - "K

π ι

a sulfamoylamino group ("N-SO -NH-), where R ¹ and R" have the meanings given in claim 1,

with a piperidylbenzimidazolinone of the general formula III (

_IJ:; ■ (III)

567/0040:

1o

in the

T and Z have the meanings given in claim 1,

converts the compound of the general formula IV obtained in this way

R,

CO - CH -

ο U

(IV)

in the

R, R ", T and Z have the meanings given above,

reduced and, if the reduced compound has protecting groups, it splits off in a manner known per se.

8. A method for the preparation of the compounds according to claim 1, characterized in that you get a mix of the

defined in claim 7 piperidylbenzimidazolinone of the general formula III and a phenylglyoxal of the general Formula V

3o

CO-C

■ H

in the

R and R have the meanings given in claim 7 own,

030557/0046

subjected to an alkylating reduction.

9. A method for the preparation of the compounds according to claim 1, characterized in that the defined in claim 7 piperidylbenzimidazolinone of the general formula III with a halohydrin of the general formula VI

CHOH - CH ₂ - X (VI)

in the

X, R and R "have the meanings given in claim 7 own,

converts and, if the condensed compound, protecting groups has, this splits off in a manner known per se.

10. Pharmaceutical preparations, characterized in that they are an active ingredient Compound according to claims 1 or 3 to 6 together with suitable pharmaceutical carrier materials.

11. Pharmaceutical preparations according to claim 1o, characterized in that they are in one Form, which are particularly suitable for the treatment of autoimmune diseases, allergic diseases and Inflammatory diseases and suitable for the treatment of breathing disorders occurring in asthma diseases is.

030557 / OO4C