Burroughs Wellcome Co.

Other

John W Findlay

Geoffrey G Coker

Richard M Welch

Robert F Butz

John D McDermed

The present invention provides compounds of the formula (I): ##STR1## or salts, esters or amide derivatives thereof, wherein R.sub.1 is --CO.sub.2 H, --CH.dbd.CH--CO.sub.2 H, --(CH.sub.2).sub.n CO.sub.2 H, or --O--(CH.sub.2).sub.n CO.sub.2 H (n=1 to 4); R.sub.2 is C.sub.1.varies. alkyl or benzyl which is optionally substituted by a C.sub.1-4 alkyl group or groups; R.sub.3 is C.sub.1-4 alkoxy, C.sub.1-4 alkyl or halogen. Also provided are pharmaceutical formulations containing the compounds of the formula (I) and methods for the preparation of the compounds. The above mentioned compounds have antihistaminic activity.

Piperazinyl benzyl acids having antihistamine activity

The invention provides compounds of the formula (I) ##STR1## or salts, esters, or amides or other protected forms thereof; wherein R.sub.1 is a C.sub.1-7 bivalent aliphatic hydrocarbon group or a single bond;

Pyridylvinyl-1H tetrazole having antihistamine activity

This disclosure describes compounds of Formula I. ##STR1## (including their pharmaceutically acceptable salts and esters) which have potent antihistamine activity which are substantially free from sedative effects.

3-[6-[3-pyrrolidino-1-(4-tolyl)prop-1e-enyl]-2-pyridyl]propionic acid

This disclosure describes a compound of Formula I ##STR1## (including its pharmaceutically acceptable salts and esters) which has potent antihistamine activity which is substantially free from sedative effects and which has little or no anticholinergic effects.

Antihistaminic compositions and methods containing pyridine derivatives

This disclosure describes a compound of Formula 1 ##STR1## (including its pharmaceutically acceptable salts and esters) which has potent antihistamine activity which is substantially free from sedative effects and which has little or no anticholinergic effects.

Use of trifluoromethyl compounds

The compound 2-[10-(2-Dimethylaminopropyl)-2-phenothiazinyl]-2-methylpropionic acid or a pharmaceutically acceptable salt thereof. The compound and salt are useful as antihistamines.

Branched chain phenothiazine

This disclosure describes compounds of formula I. ##STR1## wherein X is Cl or Br (including their pharmaceutically acceptable salts and esters) which have potent antihistamine activity and which are substantially free from sedative effects.

Anti-histaminic pyridyl compounds

The invention provides a compound of the formula (I): ##STR1## or a salt, ester or amide thereof; wherein R.sub.1 is hydrogen or C.sub.1-4 alkyl and R.sub.2 is C.sub.1-4 alkyl substituted by a group R.sub.3 CO.sub.2 H or R.sub.1 and R.sub.2 taken together with the nitrogen comprise a nitrogen-containing heterocyclic ring having four to six ring members substituted by a group R.sub.3 CO.sub.2 H, wherein R.sub.3 is a C.sub.1-7 aliphatic hydrocarbon group or a single bond; R.sub.4 is hydrogen, halogen, hydroxy, cyano, C.sub.1-4 acyloxy, C.sub.1-4 alkoxy or C.sub.1-4 alkyl optionally substituted by one to three halogen atoms; X is --N.dbd. or --CH.dbd.; and A and B each represent hydrogen atoms or --CA--CB-- represents --C.dbd.C--. The invention also provides a method for the preparation of compounds of the formula (I), novel chemical intermediates in their preparation and pharmaceutical formulations. Compounds of the formula (I) have antihistaminic activity.

Certain 1,1-diaryl-propenyl-3-(1-pyrrolidino-2-carboxylic acids,

The present invention provides a compound of the formula (I): ##STR1## or a salt, ester or amide thereof; wherein R.sub.1 is --COOH, --CH.dbd.CH--COOH, --CH.sub.2 COOH, or (CH.sub.2).sub.2 COOH. R.sub.2 is alkoxy (1-4 carbons), alkyl (1-4 carbons), hydrogen, or halogen. R.sub.3 and R.sub.4 may be the same or different and can be hydrogen, or lower alkyl(1-4 carbons) or NR.sub.3 R.sub.4 is pyrrolidino. Also disclosed are methods for the preparation of the above compounds and pharmaceutical formulations containing them. The above compounds have antihistaminic activity.

Antihistaminic 2-(amino ethylamino) pyridines

Pyridyl acrylate compound

Diphenylmethane compounds

6-[3-Amino-1-(4-tolyl)prop-1E-enyl]pyridine-2-carboxylic acid

3-{6-[3-Pyrrolidino-1-(4-tolyl)prop-1-enyl]-2-pyridyl}acrylic acid and

A radioimmunoassay proceedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--O--(CH.sub.2).sub.q --COOH where Q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or

Bupropion radioimmunoassay, and kit

A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--O--(CH.sub.2).sub.q --COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or

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Chapel Hill, NC, United States of America

John W Findlay