Patents Examined by D. B. Springer
  • Patent number: 4622407
    Abstract: Racemic mixture of derivatives of 5-(1-methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole -2-carboxylic acid and analogs were resolved into pure l- or d-isomers via concomitant isomerization and functional crystallization.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: November 11, 1986
    Assignee: Merck & Co., Inc.
    Inventor: William K. Hagmann
  • Patent number: 4621145
    Abstract: 4-Amino-5-hexenoic acid is prepared by:(a) reacting 5-oxo-2-pyrrolidine-acetonitrile with hydrogen and dimethylamine in the presence of a palladium catalyst to form N,N-dimethyl-2-[5'-oxo-2'-pyrrolidine]ethylamine;(b) oxidizing N,N-dimethyl-2-[5'-oxo-2'-pyrrolidine]-ethylamine to produce the corresponding N-oxide derivative;(c) pyrolysis of the N-oxide derivative to form 5-vinyl-2-pyrrolidinone;(d) optionally, separating N,N-dimethyl-2-[5'-oxo-2'-pyrrolidine]ethylamine by-product from the 5-vinyl-2-pyrrolidinone product; and(e) hydrolyzing 5-vinyl-2-pyrrolidinone to form 4-amino-5-hexenoic acid.
    Type: Grant
    Filed: November 29, 1983
    Date of Patent: November 4, 1986
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Wolfgang Frieben, Fritz Gerhart
  • Patent number: 4620015
    Abstract: A novel, efficient, economical procedure for the synthesis of ethers of n-propanoldiamine having the formula: ##STR1## wherein R is a straight or branched chain lower alkyl group or an aralkyl group, Ar is an aromatic group, Ar.sup.1 is an aromatic or heterocyclic group, A is a tertiary aliphatic, cycloaliphatic or heterocyclic amino group and addition salts thereof with pharmacologically acceptable acids.
    Type: Grant
    Filed: August 10, 1983
    Date of Patent: October 28, 1986
    Assignee: Carter-Wallace, Inc.
    Inventor: Frank J. Stiefel
  • Patent number: 4618365
    Abstract: A compound having the formula the formula ##STR1## where R is C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.13 alkoxyalkyl, C.sub.7 -C.sub.9 aralkyl, phenyl, naphthyl, phenyl substituted with F, Cl, Br, I, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, methylenedioxy, NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 are the same or different and are hydrogen or C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.5 alkoxycarbonyl, phenoxy, NO.sub.2, cyano, trihalomethyl or trihalomethoxy where halo is F, Cl or Br or benzyl substituted with F, Cl, Br, I, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, methylenedioxy, C.sub.2 -C.sub.5 alkoxycarbonyl, carboxy, phenoxy, NO.sub.2, cyano, trihalomethyl or trihalomethoxy where halo is F, Cl or Br; R.sup.1 and R.sup.2 are the same or different and are C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkyl or R.sup.1 and R.sup.2 together are C.sub. 4 -C.sub.8 alkylene or C.sub.4 -C.sub.8 oxydialkylene is disclosed.
    Type: Grant
    Filed: December 9, 1983
    Date of Patent: October 21, 1986
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Rupert A. Covey, Patricia J. Forbes, Allyn R. Bell
  • Patent number: 4618684
    Abstract: 3-[(Alkoxy)(aryl or heteroaryl)methyl]-1H-indoles which are useful as color formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting 3-[(arylsulfonyl)(aryl or heteroaryl)methyl]-1H-indoles with alcohols in the presence of a base.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: October 21, 1986
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4617395
    Abstract: Quinoline and substituted quinolines are prepared by reacting aniline or a substituted aniline with an .alpha., .beta.-monounsaturated aldehyde in a high-boiling mineral oil by a method in which the high-boiling mineral oil is replaced when it becomes enriched with by-products, and the said mineral oil enriched with by-products is removed.
    Type: Grant
    Filed: October 15, 1984
    Date of Patent: October 14, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Helmut Hagen, Herbert Krug
  • Patent number: 4613669
    Abstract: A process for the preparation of 1,4-diketopyrrolo-[3,4-c]pyrroles of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 independently of the other is an isocyclic aromatic or non-basic heterocyclic aromatic radical, which process comprises reacting 1 mole of the compound of formula ##STR2## wherein M is a metal atom, Z is alkyl or aryl, X is halogen or acetate, and m is a value from 0 to 2, with 1 mole of a compound of the formulaYCH.sub.2 COOZ (III)wherein Y is halogen, and with 1 mole of a nitrile of the formulaR.sub.1 --CN (IV) or R.sub.2 --CN (V)in an organic solvent and at elevated temperature, and isolating the compound of formula I.The compounds obtained according to the invention are suitable for pigmenting organic material of high molecular weight.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: September 23, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Luigi Cassar, Abul Iqbal, Alain C. Rochat
  • Patent number: 4612325
    Abstract: Novel 5-aroyl-6-methylthio-, 6-methylsulfinyl-, or 6-methylsulfonyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids represented by the formulas ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, whereinR.sub.1 is lower alkylthio, lower alkylsulfinyl, or lower alkylsulfonyl;R.sub.2 is hydrogen, hydroxy, lower alkyl, vinyl, cyclohexyl, cyclopropyl, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, nitro, amino, lower alkylcarbonylamino, lower alkylthio, lower alkylsulfonyl, or lower alkylsulfinyl;X is oxygen, sulfur, N--R.sub.3 where R.sub.3 is hydrogen or lower alkyl.This invention describes intermediates of the process and the process for the production of these compounds and their pharmaceutically acceptable non-toxic salts and pharmaceutical composition thereof. The claimed compounds are useful as anti-inflammatories and analgesics in mammals.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: September 16, 1986
    Assignee: Syntex (U.S.A) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse
  • Patent number: 4608384
    Abstract: New thieno[2,3-b] pyrrole compounds of the formula: ##STR1## in which: R.sub.1 is hydrogen or lower alkyl,R.sub.2 is cyano, carboxy, COOM in which M is alkali alkaline-earth metal, ammonium mono-, di-, or tri-, (C.sub.1 -C.sub.5) alkylammonium optionally substituted by hydroxy, COOR in which R is lower alkyl, or ##STR2## in which R' and R" are hydrogen or lower alkyl; R.sub.3 is lower alkyl; andR.sub.4 is lower alkyl, phenyl, halophenyl, lower alkylphenyl, lower alkoxy-phenyl nitrophenyl and di-lower-alkylamino,and enatiomers thereof.These new compounds may be used as medicines especially in the treatment of acute and chronic pains.
    Type: Grant
    Filed: December 12, 1983
    Date of Patent: August 26, 1986
    Assignee: Adir, S.A.R.L.
    Inventors: Michel Wierzbicki, Jacques Bure
  • Patent number: 4605662
    Abstract: A novel 1-substituted pyrrolizidine derivative having the formula: ##STR1## (wherein R.sup.1 is hydrogen or a lower alkyl group; R.sup.2 is hydrogen, a lower alkyl or lower alkoxy group, or a halogen; R.sup.3 is hydrogen, a lower alkyl, lower alkoxy or amino group, or a halogen),which can be produced by reacting 1-chlorocarbonyl (or alkoxycarbonyl)pyrrolizidine with a corresponding substituted aniline (or an alkali metal salt thereof). The pyrrolizidine derivative has antiarrhythmic activity.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: August 12, 1986
    Assignee: Suntory Ltd.
    Inventors: Seiji Miyano, Kunihiro Sumoto, Fumio Satoh, Hidetsura Cho
  • Patent number: 4604403
    Abstract: The invention relates to novel substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, their analogs and their salts. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.
    Type: Grant
    Filed: May 1, 1984
    Date of Patent: August 5, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4604383
    Abstract: The invention relates to pyrrolidinones of the general formula: ##STR1## in which: R.sub.1 represents hydrogen or alkylR.sub.2 represents alkyl, phenyl or trimethylsilyl.R.sub.3 represents 2-thienyl or a phenyl possibly substituted once or twice with halogen, methyl, methoxy or a trifluoromethyl group. It relates also to a process for the production of these compounds and to the pharmaceutical compositions containing them.
    Type: Grant
    Filed: July 5, 1984
    Date of Patent: August 5, 1986
    Assignee: Societe Anonyme Styled: SANOFI
    Inventors: Kathleen Biziere, Jean-Pierre Chambon, Jean-Charles Molimard
  • Patent number: 4603217
    Abstract: A novel anti-inflammatory drug, which exhibits rapidly a pharmacological activity, maintains the activity for a long time, and is free from a side effect such as a gastrointestinal disorder or a central nervous disturbance is disclosed.The drug comprises a compound of an alkylcarbonyloxyalkylester or alkenylcarbonyloxyalkylester derivative of indolylacetic acid or anilinophenylacetic acid.The compound is prepared by an esterification reaction.
    Type: Grant
    Filed: July 25, 1984
    Date of Patent: July 29, 1986
    Assignee: Kaken Pharmaceutical Co., Ltd.
    Inventors: Katsuhiro Uchida, Mitsuo Mimura, Shozo Masumoto, Makoto Okumura, Masao Tohno, Misako Matsumura
  • Patent number: 4603210
    Abstract: A process for preparing acemetacin which process comprises removing a protecting group, which is other than tetrahydropyranyl group and is removable under acidic conditions, from an acemetacin ester represented by the formula ##STR1## wherein R means the protecting group, under the acidic conditions.
    Type: Grant
    Filed: April 11, 1984
    Date of Patent: July 29, 1986
    Assignees: Troponwerke GmbH & Co. KG., Kowa Company
    Inventors: Yasuo Kikugawa, Yoshinori Kyotani
  • Patent number: 4600783
    Abstract: Acemetacin is prepared by reaction of an indometacin with tert.-butyl halogenoacetate and subsequent cleavage with sulphuric acid and/or sulphonic acid.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: July 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Samir Samaan, Harald Horstmann
  • Patent number: 4600714
    Abstract: Fenoldopam 4',8-bis-hydrogen sulfate and its salts are useful prodrugs to obtain extended dopaminergic activity. A useful species is the monoammonium salt.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: July 15, 1986
    Assignee: SmithKline Beckman Corporation
    Inventors: Dimitri Gaitanopoulos, Joseph Weinstock
  • Patent number: 4600777
    Abstract: 1-C.sub.1-3 straight chain alkyl 7-oxodecahydroquinoline, chemical intermediates.
    Type: Grant
    Filed: August 2, 1984
    Date of Patent: July 15, 1986
    Assignee: Eli Lilly and Company
    Inventors: Diane L. Huser, John M. Schaus, Robert D. Titus, Leland O. Weigel
  • Patent number: 4599345
    Abstract: A chlorinated quinoline derivative of formula (I) ##STR1## wherein R.sup.1 is --CCl.sub.3, --CF.sub.3, --CHCl.sub.2 or --CH.sub.2 Cl, R.sup.2 is hydrogen when R.sup.3 is not hydrogen, or is halogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl or R.sup.1, R.sup.3 is hydrogen when R.sup.2 is not hydrogen or is halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or CF.sub.3, R.sup.6 is hydrogen or halogen, X is halogen. The compounds are made by chlorination of selected compounds as disclosed and the new compounds can have antimicrobial, antifungal or analgesic effects.
    Type: Grant
    Filed: December 1, 1983
    Date of Patent: July 8, 1986
    Assignee: Alkaloide Vegyeszeti Gyar
    Inventors: Zoltan Salamon, Ilona Imre nee Virag, Magdolna Sebestyen
  • Patent number: 4599343
    Abstract: A perfluorobicyclo compound of the general formula: ##STR1## wherein either or both of Ring A and Ring B may optionally be substituted with lower perfluoroalkyl group(s) and m and n each represent 3 or 4.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: July 8, 1986
    Assignee: The Green Cross Corporation
    Inventors: Kazumasa Yokoyama, Chikara Fukaya, Yoshio Tsuda, Taizo Ono, Yoshio Arakawa, Tadakazu Suyama
  • Patent number: 4598150
    Abstract: The present invention relates to a novel compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 respectively represent hydrogen atom, lower alkyl group of 1 to 5 carbon atoms, lower alkoxy group of 1 to 5 carbon atoms or halogen atom; R.sup.3 represents hydrogen atom, alkyl group of 1 to 12 carbon atoms, alkoxyalkyl group of 1 to 12 carbon atoms, halogenoalkyl group of 1 to 12 carbon atoms, phenyl group which may be substituted or benzyl group which may be substituted; and m and n are an integer of 1 or 2; providing the R.sup.1 and R.sup.2 do not represent hydrogen atom, methyl group and methoxy group when R.sup.3 represents hydrogen atom or methyl group.Further, the present invention relates to color developing compositions suitable for use in a recording material and pressure- or heat-sensitive recording sheet containing the novel compound of the formula (I).
    Type: Grant
    Filed: February 16, 1984
    Date of Patent: July 1, 1986
    Assignee: Yamada Chemical Co. Ltd
    Inventors: Hideaki Fujisaki, Seiichi Nieda, Katsuhiko Tsunemitsu