Ucb Societe Anonyme

Ucb Pharmaceuticals, Inc.

Ludovic Rodriguez

Jacques Leclercq

Eric Cossement

Pierre Ykman

Lucien Marchal

Eugene Baltes

Paul Croisier

Jean De Lannoy

Jacques Leclerca

New 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids, their amides and their salts, processes for the preparation thereof and therapeutic compositions. These compounds have the formula ##STR1## wherein Y=--OH or --NH.sub.2 ; X and X'=H, halogen, alkoxy or trifluoromethyl; m=1 or 2 and n=1 or 2. The amides of the 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids are prepared either by reacting a 1-(diphenylmethyl)-piperazine with an omegahaloacetamide, or by reacting an alkali metal salt of an omega-[4-(diphenylmethyl)-1-piperazinyl]-alkanol with a 2-haloacetamide, or yet by reacting ammonia with a halide or alkyl ester of a 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acid, whereas the 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids are prepared by hydrolyzing the corresponding amide or lower alkyl ester. These compounds have in particular an antiallergic, spasmolytic and antihistaminic activity.

2-[4-(Diphenylmethyl)-1-piperazinyl]-acetic acids and their amides

New 2-[4-(diphenylmethylene)-1-piperidinyl]-acetic acids and their amides, processes for the preparation thereof and therapeutic compositions. These compounds have the formula ##STR1## wherein Y=--OH or --NR.sub.1 R.sub.2, R.sub.1 and R.sub.2 =H, alkyl or phenyl; X=H, halogen or alkoxy; m=0, 1 or 2 and n=1 or 2. The 2-[4-(diphenylmethylene)-1-piperidinyl]-acetic acids are prepared by hydrolyzing the corresponding amide or lower alkyl ester, whereas the amides are prepared either by reacting a 4-(diphenylmethylene)-piperidine with an omega-haloacetamide, or by reacting an alkali metal salt of an omega-[4-diphenylmethylene)-1-piperidinyl]-alkanol (m=1 or 2) with a 2-haloacetamide, or by reacting a nitrogen compound (HNR.sub.1 R.sub.2) with a halide or alkyl ester of a 2-[4-(diphenylmethylene)-1-piperidinyl]-acetic acid. These compounds have in particular an antiallergic, spasmolytic, antihistaminic and broncholytic activity.

2-[4-(Diphenylmethylene)-1-piperidinyl]-acetic acids and their amides

6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acid derivatives having the formula ##STR1## wherein R is a methyl, phenyl or benzyl radical, Z.sub.1 is a hydrogen atom and Z.sub.2 is a radical selected from those known from penicillin chemistry and is preferably a 2-phenylacetyl, 2-amino-2-phenylacetyl, 5-methyl-3-phenyl-4-isoxazolecarbonyl or 2,6-dimethoxybenzoyl radical, or Z.sub.1 and Z.sub.2 together represent a bivalent radical Z.sub.3 and preferably a (hexahydro-1H-azepin-1-yl)methylene radical, as well as the pharmaceutically acceptable non-toxic salts thereof and process for preparing the same. These compounds have valuable antibacterial properties and are useful as therapeutic agents in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.

6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acid, antibacterial

6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acids, salts and esters thereof of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl or an alkali metal or ammonium ion and R.sub.2 is methyl, phenyl or benzyl and process for preparing the same. These compounds are useful as intermediates in the synthesis of a new group of antibiotics having properties similar to penicillins, besides own antibiotic activity with a broad antibacterial spectrum. Therefore, they are useful as antibacterials agents and as therapeutic agents for humans and for animals in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.

6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acids, antibacterial

New lactam-N-acetic acids and amides thereof having the formula ##STR1## wherein R.sub.1 and R.sub.2 =H, C.sub.1 -C.sub.4 -alkyl, aryl or halogen-substituted aryl,

Lactam-N-acetic acids and their amides

New physiologically active N-substituted lactams having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7, represent independently a hydrogen atom, an alkyl radical containing 1 to 4 carbon atoms or a phenyl group, R.sub.8 is a hydrogen atom or R.sub.8 and R.sub.3 together form the ethylene or trimethylene radical, and n is 3, 4 or 5, processes for the preparation thereof and pharmaceutical compositions containing the same.

N-substituted lactams

6'-Amino-spiro�cycloalkane-1,2'-penam!-3'-carboxylic acid derivatives having the formula ##STR1## WHEREIN N IS A WHOLE NUMBER OF FROM 3 TO 6 AND R.sub.1 and R.sub.2 represent substituents known in the chemistry of penicillins, and their pharmaceutically acceptable, non-toxic salts, have valuable antibacterial properties and are useful as therapeutic agents in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria. Processes for preparing these compounds are also described.

6'-Amino-spiro�cycloalkane-1,2'-penam!-3'-carboxylic acid derivatives

Amino-spiro[oxa(or thia)cycloalkane-penam]-carboxylic acid derivatives having the formula ##STR1## WHEREIN X is a sulfur or oxygen atom or the sulfinyl group, n is 1 or 2, m is 1 or 2, R.sub.1 is hydrogen, R.sub.2 is one of the radicals known in the chemistry of the penicillins, preferably 2-phenylacetyl, 2-amino-2-phenylacetyl, 5-methyl-3-phenyl-4-isoxazolecarbonyl or 2,6-dimethoxybenzoyl, or R.sub.1 and R.sub.2 together represent a bivalent radical R.sub.3, preferably (hexahydro-1H-azepin-1-yl)methylene and their therapeutically acceptable non-toxic salts and process for preparing the same. These compounds have valuable antibacterial properties and are useful as therapeutic agents in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.

Amino-spiro[oxa(or thia)cycloalkane-penam]-carboxylic acid derivatives

Amino-spiro[oxa(or thia)cycloalkane-penam]-carboxylic acid, a salt or an ester thereof, of the formula ##STR1## wherein Z is a hydrogen or an alkali metal atom, or a group protecting the carboxylic function, X is a sulfur or oxygen atom, n is 1 or 2, m is 1 or 2, and process of preparing the same. These compounds are useful as intermediates in the synthesis of a new group of antibiotics having properties similar to penicillins, besides own antibiotic activity with a broad antibacterial spectrum.

Amino-spiro[oxa(or thia)cycloalkane-penam]-carboxylic

6'-Amino-spiro[cycloalkane-1,2'-penam]-3'-carboxylic acids of the formula ##STR1## WHEREIN Z is a hydrogen or an alkali metal atom, or a protective group, and n a whole number of from 3 to 6, and process of preparing the same. These compounds are useful as intermediates in the synthesis of a new group of antibiotics having properties similar to the penicillins.

6'-Amino-spiro(cycloalkane-1,2'-penam)-3'-carboxylic acids

New physiologically active 2-carbamoyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-ones having the general formula ##STR1## wherein R.sub.1 is hydrogen or phenyl, R.sub.2 is morpholino or amino mono- or di-substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.5 -C.sub.6 -cycloalkyl or phenyl, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.5 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkoxy, R.sub.8 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl, processes for the preparation thereof and pharmaceutical compositions containing the same. In particular, the compounds of this invention are useful in the treatment of memory disorders.

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Brussels, Belgium

Ludovic Rodriguez