Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen or lower alkyl; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl;are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.
Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen, lower alkyl, chloro or bromo; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl; are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.
Abstract: 5-benzoyl-7-halo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, represented by the formula ##STR1## and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein:R is hydrogen or lower alkyl;X is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, carboxyl, lower alkylcarbonyl, sulfonic acid, sulfonic acid alkyl ester, fluoro, chloro, or bromo; and Y is chloro or bromo, which are novel, and 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids which are represented by the formula ##STR2## wherein X and R are as above defined except that X cannot be chloro or bromo, are prepared by decarboxylation of the corresponding 1,1 dicarboxylates. Intermediates in said preparation are also disclosed.
Abstract: Novel 5-aroyl-6-chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-7-carboxylic acids represented by the formula ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein Y is chloro or bromo and Ar is an optionally substituted phenyl, 2-furyl, or 2-thienyl ring or a 3-furyl, 3-thienyl, 2-pyrrolyl or 1-alkyl-2-pyrrolyl ring. These compounds are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
Abstract: Nonapeptide and decapeptide analogs of LHRH which have the formula: ##STR1## and the pharmaceutically acceptable salts thereof, wherein: X is a D-alanyl residue wherein one hydrogen on C-3 is replaced by:(a) a carbocyclic aryl-containing radical selected from the group consisting of phenyl substituted with three or more straight chain lower alkyl groups, naphthyl, anthryl, fluorenyl, phenanthryl, biphenylyl and benzhydryl; or(b) a saturated carbocyclic radical selected from the group consisting of cyclohexyl substituted with three or more straight chain lower alkyl groups, perhydronaphthyl, perhydrobiphenylyl, perhydro-2,2-diphenylmethyl, and adamantyl; or(c) a heterocyclic aryl containing radical selected from the group consisting of radicals represented by the following structural formulas: ##STR2## wherein A" and A' are independently selected from the group consisting of hydrogen, lower alkyl, chlorine, and bromine, and G is selected from the group consisting of oxygen, nitrogen, and sulfur;A is an aminoac
Type:
Grant
Filed:
October 6, 1980
Date of Patent:
July 27, 1982
Assignee:
Syntex Inc.
Inventors:
John J. Nestor, Gordon H. Jones, Brian H. Vickery
Abstract: Compounds useful in the prevention and/or treatment of hypertension, congestive heart failure, arrhythmia, migraine, vasospastic disorders, and asthma are represented by the formula ##STR1## wherein: R, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently hydrogen or lower alkyl of one to four carbon atoms; andR.sup.5 and R.sup.6 are independently hydrogen, lower alkyl of one to four carbon atoms or lower alkoxy of one to four carbon atoms; andthe pharmaceutically acceptable acid addition salts thereof.
Abstract: Stable compositions of PGE-type compounds are achieved by dissolving those compounds in carbonate diester solvents which may contain water up to the solubility limit of the carbonate diester.
Abstract: A solution for cleaning, storing or wetting contact lenses which comprises a poly(oxyethylene)-poly(oxypropylene) substituted ethylenediamine surfactant having a molecular weight between 1,600 and 27,000; a germicidal agent; a viscosity builder; a tonicity agent; a sequestering agent and water.
Abstract: The 17-butyrate, 17-benzoate, 17,21-methyl orthobutyrate, 17,21-methyl orthobenzoate, and 17,21-dibutyrate esters of cloprednol (6-chloro-11.beta., 17.alpha., 21-trihydroxy-pregna-1,4,6-triene-3,20-dione) are useful as topical, anti-inflammatory steroids.
Type:
Grant
Filed:
March 9, 1978
Date of Patent:
April 6, 1982
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
John H. Fried, Denis J. Kertesz, Michael Marx
Abstract: Certain 1,4,5,6-tetrahydropyrimidine compounds which are substituted with an amino, amido or carbamate at the 2-position, with an optionally substituted phenyl at the 5-position or at the 4-position when there is no alkyl at the 1-position and optionally a lower alkyl at the 1-position when the phenyl is at the 5-position are useful as CNS agents and as antihypertensives.
Abstract: Compounds useful as anticonvulsant agents, antifungals and antibacterials are represented by the formula ##STR1## wherein R.sup.1 is phenyl optionally substituted by one or more substituents selected from the group consisting of halo, lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and trifluoromethyl; Z is ethylene or propylene optionally substituted by one or more lower alkyl groups of one to four carbon atoms; m is 1, 2, 3 or 4 and n is 0, 1, 2 or 3 with the proviso that the sum of m and n is 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.The ketone intermediates useful in preparing compounds of formula (I) also have anticonvulsant activity.
Abstract: Novel peptides of the formula: ##STR1## wherein: A, A' and A" are each independently Gly, D-Ala, D-Leu, or D-Trp, wherein A may optionally be N-alkylated or N-acylated;B is Pro, .DELTA..sup.3 -Pro, Thz, or diMeThz;C and C' are each independently Thr, Ser, Val, or alloThr;D is Glu, Gln, Asp, or Asn;R is hydrogen, or is lower alkyl or lower acyl, substituted for one of the hydrogens on the .epsilon.-amino group of the lysyl residue;X is Cys, Ala, ABU, or Cys(Me); andY is selected from the group consisting of hydroxy, Pro, Pro-Leu, and Pro-Leu-Met, -NH.sub.2, ProNH.sub.2, Pro-LeuNH.sub.2 and Pro-leu-MetNH.sub.2 ;and the pharmaceutically acceptable salts thereof, are useful for increasing immunologic competence. Methods for preparation of the peptides are also described.
Type:
Grant
Filed:
December 22, 1980
Date of Patent:
March 16, 1982
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Abraham White, deceased, John J. Nestor, Gordon H. Jones, Pamela M. Burton
Abstract: Nonapeptide and decapeptide analogs of LH-RH of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein: V is tryptophyl, phenylalanyl or 3-(1-naphthyl)-L-alanyl;W is tyrosyl, phenylalanyl or 3-(1-pentafluorophenyl)-L-alanyl;X is a D-amino acid residue of the formula: ##STR2## wherein R is a heterocyclic aryl containing radical selected from the group consisting of radicals represented by the following structural formulas: ##STR3## wherein A and A' are independently selected from the group consisting of hydrogen, lower alkyl, chlorine, and bromine, and G is selected from the group consisting of oxygen, nitrogen, and sulfur;Y is leucyl, isoleucyl, nor-leucyl or N-methyl-leucyl;Z is glycinamide or --NH--R.sup.1, wherein:R.sup.1 is lower alkyl, cycloalkyl, fluoro lower alkyl or ##STR4## wherein R.sup.2 is hydrogen or lower alkyl,are disclosed. These compounds exhibit potent LH-RH agonist properties.
Type:
Grant
Filed:
June 23, 1980
Date of Patent:
March 9, 1982
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
John J. Nestor, Gordon H. Jones, Brian H. Vickery
Abstract: Certain 16.beta.-methyl-3-oxoandrost-4-ene and 16.beta.-methyl-3-oxoandrosta-1,4-diene 17.beta.-thiocarboxylic acid esters are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 6.alpha.-position with fluoro or chloro; optionally substituted at the 9.alpha. position with fluoro, chloro or bromo; substituted at the 11 position with a keto, a .beta.-hydroxy or a .beta.-chloro (the latter only when there is a 9.alpha.-chloro); and substituted with 17.alpha.-hydroxy (or an ester thereof).
Abstract: 2-(1,4-Benzodioxan-2-ylalkyl)imidazoles having the general formula: ##STR1## wherein R.sup.1, and R.sup.2 and R.sup.3 are independently selected from the group consisting of hydrogen, and alkyl, and wherein n is an integer equal to 0, 1 or 2, and the pharmaceutically acceptable acid addition salts thereof, are useful as antidepressants.
Type:
Grant
Filed:
September 10, 1980
Date of Patent:
November 24, 1981
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Arthur F. Kluge, Arthur M. Strosberg, Roger Whiting, George Christie
Abstract: Compounds of the formula ##STR1## and the pharmaceutically acceptable, non-toxic salts thereof, wherein: R is hydrogen, lower alkyl, or benzyl;X is a substitution for hydrogen at any position in the benzene ring and is selected from the group consisting of lower alkyl, lower alkoxyl, benzyl and halo;m is an integer from 0 to 4; andn is an integer from 0 to 2;are novel. These compounds have been shown to be .alpha..sub.2 blockers, and are, therefore, anti-depressants.
Type:
Grant
Filed:
December 3, 1980
Date of Patent:
November 17, 1981
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Arthur F. Kluge, Arthur M. Strosberg, Roger Whiting, George A. Christie
Abstract: This process relates to the synthesis of unsaturated aliphatic esters useful as insect sex attractants, including gossyplure, the insect sex pheromone of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor. The process utilizes a cyclic phosphonium (Wittig) reagent.
Abstract: 4,5-Dihydro-2-lower alkoxycarbonylamino-4-phenyl imidazoles and substituted phenyl derivatives thereof lower the blood pressure in a human being when administered at low doses.
Abstract: Compounds of the formula ##STR1## wherein Z is C.sub.1 and C.sub.4 alkoxymethylene, hydroxymethylene, esterified hydroxymethylene, carbonyl, or ketal-protected carbonyl, and the pharmaceutically acceptable acid addition salts thereof, are useful as anticonvulsant and anti-secretory agents.
Abstract: Certain 3-oxoandrost-4-ene and 3-oxoandrosta-1,4-diene 17.beta.-carboxylic acids (and esters thereof) substituted at the 4-position with a fluoro or chloro, optionally substituted at the 6- position with fluoro or chloro and at 16.beta. with methyl are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 9.alpha. position with fluoro, chloro or bromo; substituted at the 11 with a keto, a beta-hydroxy or a beta-chloro (the latter only when there is a 9.alpha.-chloro); when there is a 17.alpha.-hydroxy (or an ester).