Abstract: Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivatives thereof) comprising the following steps: (a) reducing .alpha.-oxo-2-nitrobenzenepropanoic acid to .alpha.-hydroxy-2-nitrobenzenepropanoic acid, (b) replacing the hydroxyl group of the latter with a chlorine atom utilizing a selected Vilsmeier chlorinating reagent at temperatures of at least 20.degree. C., (c) reducing the nitro group of the resulting .alpha.-chloro-2-nitrobenzenepropanoic acid to obtain .alpha.-chloro-2-aminobenzenepropanoic acid, and (d) cyclizing the latter in aqueous base to form the desired indoline-2-carboxylic acid. Alternately, steps (c) and (d) may be combined in a one pot step by using, for example, a Raney nickel-hydrazine reducing medium.

Abstract: Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises:(a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV;(b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.

Abstract: Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivaties thereof) comprising the following step: (a) reducing .alpha.-oxo-2-nitrobenzenepropanoic acid to .alpha.-hydroxy-2-nitrobenzenepropanoic acid, (b) replacing the hydroxyl group of the latter with a chlorine atom utilizing a selected Vilsmeier chlorinating reagent at temperatures of at least 20.degree. C., (c) reducing the nitro group of the resulting .alpha.-chloro-2-nitrobenzenepropanoic acid to obtain .alpha.-chloro-2-aminobenzenepropanoic acid, and (d) cyclizing the latter in aqueous base to form the desired indoline-2-carboxylic acid. Alternately, steps (c) and (d) may be combined in a one pot step by using, for example, a Raney nickel-hydrazine reducing medium.

Abstract: Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises:(a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV;(b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.

Abstract: Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises:(a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV;(b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.

Abstract: Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivatives thereof) comprising the following steps: (a) reducing .alpha.-oxo-2-nitrobenzenepropanoic acid to .alpha.-hydroxy-2-nitrobenzenepropanoic acid, (b) replacing the hydroxyl group of the latter with a chlorine atom utilizing a selected Vilsmeier chlorinating reagent at temperatures of at least 20.degree. C., (c) reducing the nitro group of the resulting .alpha.-chloro-2-nitrobenzenepropanoic acid to obtain .alpha.-chloro-2-aminobenzenepropanoic acid, and (d) cyclizing the latter in aqueous base to form the desired indoline-2-carboxylic acid. Alternately, steps (c) and (d) may be combined in a one pot step by using, for example, a Raney nickel-hydrazine reducing medium.

Abstract: Disclosed herein is a process for obtaining indoline-2-carboxylic acid ester tin complexes directly from o-nitropyruvic acids using metallic tin and dry hydrogen chloride gas in a lower alkanol solvent, at atmospheric pressures.

Abstract: Disclosed herein are 2,3-dihydro-1H-indole-2-carboxylic acids substituted on the nitrogen with 3-mercapto-2-alkyl-1-oxoalkyl, 3-phosphoryl-2-alkyl-1-oxopropyl, or 2-amino-2-alkyl-1-oxoalkyl derivatives which act as inhibitors of angiotensin converting enzyme and as antihypertensive agents. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0;R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or aroyl;R.sub.5 is hydroxy, amino, or lower alkoxy;X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen;Y is hydrogen, lower alkyl, or aryl;Y is hydrogen, lower alkyl, or aryl;R.sub.4 is ##STR2## wherein: L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl);M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.10 are, independently, hydrogen, lower alkyl, or aryl);A is O, NR.sub.

Abstract: Disclosed herein are 2,3-dihydro-1H-indole-2-carboxylic acids substitued on the nitrogen with 3-mercapto-2-alkyl-1-oxoalkyl, 3-phosphoryl-2-alkyl-1-oxopropyl, or 2-amino-2-alkyl-1-oxoalkyl derivatives which act as inhibitors of angiotensin converting enzyme and as antihypertensive agents. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0;R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or aroyl;R.sub.5 is hydroxy, amino, or lower alkoxy;X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen; Y is hydrogen, lower alkyl, or aryl;Y is hydrogen, lower alkyl, or aryl;R.sub.4 is ##STR2## wherein: L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl);M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.10 are, independently, hydrogen, lower alkyl, or aryl);A is O, NR.sub.

Abstract: Disclosed herein are N-(3-mercapto-2-alkyl-1-oxopropyl)-2,3-dihydro-1H-indole-2-carboxylic acids and derivatives thereof which act as inhibitors of angiotensin converting enzyme and as anti-hypertensive agents. Derivatives include those in which the 3-mercapto group is substituted with phosphate derivatives or is replaced by a variously substituted amino group. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0;R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or aroyl;R.sub.5 is hydroxy, amino, or lower alkoxy;X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen;Y is hydrogen, lower alkyl, or aryl;R.sub.4 is -SH, ##STR2## wherein L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl);M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.

Abstract: Disclosed herein are N-(3-mercapto-2-alkyl-1-oxopropyl)-2,5-dihydro-1H-indole-2-carboxylic acids and derivatives thereof which act as inhibitors of angiotensin converting enzyme and as anti-hypertensive agents. Derivatives include those in which the 5-mercapto group is substituted with phosphate derivatives or is replaced by a variously substituted amino group. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0;R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or aroyl;R.sub.5 is hydroxy, amino, or lower alkoxy;X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen;Y is hydrogen, lower alkyl, or aryl;R.sub.4 is --SH, ##STR2## wherein L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl);M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.

Abstract: Disclosed herein are 3[[(2,3-dihydro-1H-indole-2-yl)carbonyl]thio]propanoic (and acetic) acids of the general formula: ##STR1## wherein: n is 1 or 0;R.sub.1 is hydrogen, lower alkyl, aryl, or aralkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or aroyl;X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen; andY is hydrogen, lower alkyl, or aryl; or salts thereof.These compounds are intermediates for the production of 1H,3H-[1,4]thiazepino[4,3-a]indoles and 1H-[1,4]thiazino[4,3-a]indoles which possess Angiotensin Converting Enzyme inhibition activity and anti-hypertensive activity.

Abstract: Disclosed herein are 2,3-dihydro-1H-indole-2-carboxylic acids substituted on the nitrogen with 3-mercapto-2-alkyl-1-oxoalkyl, 3-phosphoryl-2-alkyl-1-oxopropyl, or 2-amino-2-alkyl-1-oxoalkyl derivatives which act as inhibitors of angiotensin converting enzyme and as antihypertensive agents. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0;R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or aroyl;R.sub.5 is hydroxy, amino, or lower alkoxy;X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen;Y is hydrogen, lower alkyl, or aryl;Y is hydrogen, lower alkyl, or aryl;R.sub.4 is ##STR2## wherein: L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl);M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.10 are, independently, hydrogen, lower alkyl, or aryl);A is O, NR.sub.

Abstract: The compounds of this invention are designated as quinoxalinyl esters of carbamimidothioic acids and exhibit the pharmacological properties of preventing gastric ulcers, reducing gastric secretions and lowering blood pressure. The compounds have the following structural formula: ##STR1## in which Q is hydrogen or nitro;A is hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, carbomethoxy, carbethoxy, carbopropoxy, carbisopropoxy, carbobutoxy, carbisobutoxy, or carbo-t-butoxy; andR.sup.1, R.sup.2, and R.sup.3 are, independently, hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, allyl, or R.sup.1 and R.sup.3 may be concatenated with a carbon chain having 4 carbon atoms with R.sup.2 then being hydrogen; except that, when A and Q are hydrogen, R.sup.1, R.sup.2, and R.sup.3 may not all be hydrogen; and with the further exception that, where A is methyl and R.sup.1, R.sup.2, and Q are all hydrogen, R.sup.3 may not be ethyl;or a pharmaceutically acceptable salt thereof.

Abstract: Disclosed herein are N-(3-mercapto-2-alkyl-1-oxopropyl)-2,3-dihydro-1H-indole-2-carboxylic acids and derivatives thereof which act as inhibitors of angiotensin converting enzyme and as anti-hypertensive agents. Derivatives include those in which the 3-mercapto group is substituted with phosphate derivatives or is replaced by a variously substituted amino group. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0;R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or aroyl;R.sub.5 is hydroxy, amino, or lower alkoxy;X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen;Y is hydrogen, lower alkyl, or aryl;R.sub.4 is --SH, ##STR2## wherein L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl);M is R.sub.8, OR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.

Abstract: This invention is directed to novel central nervous system depressants of Formula I ##STR1## wherein R.sup.1 is selected from the group consisting of (lower)alkyl and ar(lower)alkyl; R.sup.2 is selected from the group consisting of di(lower)alkylamino(lower)alkyl and diaryl(lower)alkylamino(lower)alkyl; R.sup.1 and R.sup.2 may be concatenated to form a radical selected from the group consisting of ##STR2## wherein R.sup.4 is selected from the group consisting of (lower)alkyl, aryl, hydroxy(lower)alkyl, ar(lower)alkyl and (lower)alkoxy(lower)alkyl; R.sup.5 is selected from the group consisting of (lower)-alkylamino and piperidino; n is an integer from 3 to 5; m is an integer from 1-2; r is an integer from 2 to 3; s is an integer from 0 to 6; t is an integer from 0-6; with the proviso that the sum of s and t is 3 to 6; R.sup.

Abstract: Penicillin sulfoxides are converted to 3-halo-3-methyl-cepham-4-carboxylic acid esters and amides or the corresponding cephem derivatives by heating the penicillin sulfoxide precursor in a polyhaloalkane solvent to a temperature between 50.degree. to about 150.degree. C. in the presence of an equimolar amount of a neutral or basic catalyst, respectively. The catalysts employed are bases such as pyridine, picoline, lutidine, quinoline, isoquinoline, dimethylaniline or a quaternary ammonium salt. The 3-halo-cepham intermediates produced with a quaternary ammonium catalyst are dehydrohalogenated to afford known cephem derivatives or converted to the free 4-carboxylic acid and the alkali metal, alkaline earth metal or ammonium salts thereof to afford novel antibacterial agents.

Abstract: The antibacterial agents of this invention present the following structural formula: ##SPC1##In whichR.sup.1 is --OH, alkoxycarbonyloxy of 2 to 6 carbon atoms, arylsulfonyl of 6 to 10 carbon atoms or thiocyanato;R.sup.2 is --H, halo or phenyl;R.sup.3 is --H, an alkali metal or --NH.sub.4 ; andY is ##EQU1## wherein R.sup.

Abstract: The antibacterial agents of this invention present the following structural formula: ##SPC1##In whichA is a member selected from the group consisting of ##EQU1## M is a member selected from the group consisting of --H, an alkali metal and --NH.sub.4 ; andY is a member selected from the group consisting of ##EQU2## wherein R is --H, alkanoyloxy of 2 to 6 carbon atoms, ##SPC2##Or,When taken with the 3-carboxy group, ##SPC3## .

Abstract: Penicillin sulfoxides are converted to 3-halo-3-methyl-cepham-4-carboxylic acid esters and amides or the corresponding cephem derivatives by heating the penicillin sulfoxide precursor in a polyhaloalkane solvent to a temperature between 50.degree. to about 150.degree.C. in the presence of an equimolar amount of a neutral or basic catalyst, respectively. The catalysts employed are bases such as pyridine, picoline, lutidine, quinoline, isoquinoline, dimethylaniline or a quaternary ammonium salt. The 3-halo-cepham intermediates produced with a quaternary ammonium catalyst are dehydrohalogenated to afford known cephem derivatives or converted to the free 4-carboxylic acid and the alkali metal, alkaline earth metal or ammonium salts thereof to afford novel antibacterial agents.