Patents Examined by Paul M. Coughlan, Jr.
  • Patent number: 4501741
    Abstract: 7.beta.-[2-Amino-2-(benzothien-4,5,6, and 7-yl)acetylamino]-3-substituted-3-cepham-4-carboxylic acids and 7.beta.-[2-amino-2-(2,3-dihydrobenzothien-4,5,6, and 7 yl)acetylamino]-3H- or 3-substituted-3-cephem-4-carboxylic acids (1), e.g. 7.beta.-[2-amino-2-(benzothien-4-yl)acetylamino]-3-methyl-3-cephem-4-carbo xylic acid, are orally effective antibiotics. Also provided are benzothienyl oximino compounds, the corresponding 2,3-dihydro compounds (2) useful as intermediates to (1) and as antibiotics, as well as 7.beta.-(2,2-dialkyl-5-oxo-4-benzothienyl-1-imidazolidinyl)-3H-(3-substitu ted)-3-cephem-4-carboxylic acids and the corresponding 2,3-dihydro compounds (3) useful as antibiotics, and prepared with (1) by condensation with ketones. Pharmaceutical formulations of antibiotic compounds (1), (2), and (3) are provided.
    Type: Grant
    Filed: April 12, 1983
    Date of Patent: February 26, 1985
    Assignee: Eli Lilly and Company
    Inventors: Bernard J. Graves, Stjepan Kukolja
  • Patent number: 4501743
    Abstract: Cephalosporins of the formula ##STR1## wherein R is hydrogen, sodium, potassium or certain ester groups; R.sub.1 is in the .alpha.-configuration and is hydrogen or methoxy; R.sub.2 is hydrogen, ##STR2## X is hydrogen, ##STR3## R.sub.4 is hydrogen or lower alkyl; R.sub.5 is hydrogen, lower alkyl, ##STR4## --(CH.sub.2).sub.n --N--(lower alkyl).sub.2 ; R.sub.6 is hydrogen, sodium, or potassium; n is an integer from 1 to 4; are disclosed. These compounds are useful as anti-bacterial agents.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: February 26, 1985
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Hermann Breuer, Uwe D. Treuner, Theodor Denzel
  • Patent number: 4500539
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently lower alkyl having from 1 to 4 carbon atoms; and R.sup.3 is lower alkyl having from 1 to 6 carbon atoms, lower cycloalkyl having from 3 to 6 carbon atoms optionally substituted with methyl or ethyl, lower alkoxyalkyl having up to a total of 8 carbon atoms or lower alkylthioalkyl having up to a total of 8 carbon atoms are insecticidal.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: February 19, 1985
    Assignee: Chevron Research Company
    Inventor: Laroy H. Edwards
  • Patent number: 4500711
    Abstract: In the synthesis of calcium leucovorin (calcium 5-formyl-5,6,7,8-tetrahydrofolate), the use of an amine base in the conversion of anhydroleucovorin (5,10-methenyl-5,6,7,8-tetrahydrofolic acid) to leucovorin unexpectedly results in a pure (USP) product directly from the reaction mixture.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: February 19, 1985
    Assignee: Burroughs Wellcome Co.
    Inventors: James C. Wisowaty, Roy A. Swaringen, David A. Yeowell
  • Patent number: 4500709
    Abstract: This invention relates to novel compounds useful as intermediates in the preparation of cephalosporin compounds of antibacterial activity, having the formula ##STR1## wherein R.sup.1 is a group of the formula ##STR2## in which X is sulfur, oxygen or substituted or unsubstituted imino, andR.sup.2 is hydrogen or a saturated or unsaturated aliphatic hydrocarbon residue,a derivative at the carboxy group thereof and salt thereof.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: February 19, 1985
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Takashi Masugi, Takashi Ogino, Kiyoshi Tsuji
  • Patent number: 4500716
    Abstract: Highly active substantially pure Z-isomers of cephalosporins are produced by the following synthesis: ##STR1## in which R.sup.1, R.sup.4 and R.sup.5 ae various organic radicals,R.sup.2 is alkoxycarbonyl,Y is Cl, Br or --O--SO.sub.2 --R.sup.5, andX is a conventional cephalosporin substituent.Many of the intermediates are new, especially in pure Z-form.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: February 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Gunther Kinast
  • Patent number: 4499098
    Abstract: Compounds of the formula: ##STR1## wherein X is oxygen or sulfur; R.sup.1 and R.sup.2 are independently lower alkyl having from 1 to 4 carbon atoms; and R.sup.3 is lower alkyl having from 1 to 6 carbon atoms, lower cycloalkyl having from 3 to 6 carbon atoms optionally substituted with methyl or ethyl, lower alkoxyalkyl having up to a total of 8 carbon atoms or lower alkylthioalkyl having up to a total of 8 carbon atoms are insecticidal.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: February 12, 1985
    Assignee: Chevron Research Company
    Inventor: Laroy H. Edwards
  • Patent number: 4499088
    Abstract: This invention relates to novel cephem compounds, of antimicrobial activity, of the formula: ##STR1## wherein R.sup.1 is carboxy (C.sub.1 -C.sub.6) alkyl or esterified carboxy (C.sub.1 -C.sub.6) alkyl,R.sup.2 is carboxy or an esterified carboxy group, andR.sup.3 is (C.sub.1 -C.sub.6) alkanoylamino, (C.sub.1 -C.sub.6) alkanesulfonyl, triazolylthio, tetrazolylthio having (C.sub.1 -C.sub.6) alkyl, pyridazinylthio having (C.sub.1 -C.sub.6) alkyl, thiadiazolylthio having (C.sub.1 -C.sub.6) alkyl, triazolopyridazinylthio or tetrazolopyridazinylthio, and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: January 4, 1983
    Date of Patent: February 12, 1985
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Hisashi Takasugi, Hideaki Yamanaka
  • Patent number: 4497814
    Abstract: Disclosed are 2-(pyridinyl)-1,2,4-triazolo[1,5-a]pyrimidines and derivatives which are effective in increasing cardiac contractility. These compounds are useful in the treatment of congestive heart failure preferably by oral or parenteral administration.
    Type: Grant
    Filed: August 16, 1982
    Date of Patent: February 5, 1985
    Assignee: Schering Corporation
    Inventor: Joseph T. Witkowski
  • Patent number: 4497809
    Abstract: Cephalosporin derivatives of the formula: ##STR1## wherein R.sub.1 is methyl or ethyl and R.sub.2 is a straight-chain or branched alkyl group of 5 to 7 carbon atoms, and their pharmaceutically acceptable salts, which are effective as orally administrable antibiotic agents against both gram-positive- and negative-bacteria, and the production and compositions thereof, are proposed.
    Type: Grant
    Filed: April 20, 1983
    Date of Patent: February 5, 1985
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshinobu Yoshimura, Naoru Hamaguchi, Takatsuka Yashiki
  • Patent number: 4497815
    Abstract: A 1-(N-substituted carbamoyl)-5-fluorouracil derivative represented by the following general formula: ##STR1## R is a 4-alkoxycyclohexyl group-containing radical which is 2,3,4-trimethoxycyclohexcylethyl, 2,3,4-trimethoxycyclohexyl, 2,4-dimethoxycyclohexylmethyl, 3,4-dimethoxycyclohexylethyl, 2,4-dimethoxycyclohexyl, 2,4,5-trimethoxycyclohexyl, 3,4-dimethoxycyclohexylmethyl, 3,4,5-trimethoxycyclohexyl, 4-ethoxycyclohexyl or 4-ethoxycyclohexylmethyl. The compounds are carcinostatic agents. The compounds are used in a therapeutically effective amount in the presence of a carrier.
    Type: Grant
    Filed: January 5, 1983
    Date of Patent: February 5, 1985
    Assignee: Shoichiro Ozaki
    Inventors: Shoichiro Ozaki, Tomonori Hoshiko, Tomio Ogasawara
  • Patent number: 4497651
    Abstract: Dichloroquinoline derivatives of the formula ##STR1## are prepared as described, and are used as herbicides.
    Type: Grant
    Filed: February 17, 1982
    Date of Patent: February 5, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Juergen Markert, Bruno Wuerzer
  • Patent number: 4496722
    Abstract: Compounds and methods featuring, in one aspect, compositions containing an organic boronic acid and one or more reporter groups.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: January 29, 1985
    Assignee: The Children's Medical Center Corporation
    Inventors: Paul M. Gallop, Mercedes Paz
  • Patent number: 4496720
    Abstract: A novel process for the preparation of thioethers comprising reacting a silylated thiol of the formulaR--S--SiR.sub.1 R.sub.2 R.sub.3 Iwherein R is an organic group and R.sub.1, R.sub.2 and R.sub.3 are individually selected from the group consisting of alkyl of 1 to 4 carbon atoms with an organic halide, sulfate or sulfonate in the presence of hexamethylphosphoric triamide as a solvent or co-solvent preferably under neutral conditions in aprotic solvents at a temperature between 0.degree. and 150.degree. C.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: January 29, 1985
    Assignee: Gist-Brocades N.V.
    Inventors: Cornelis A. Bruynes, Theodorus K. Jurriens
  • Patent number: 4495186
    Abstract: The invention relates to complex salts of N-cyclohexyl-piperazino-acetamides or propionamides with dihydroxy aluminum-.alpha.-hydroxy-carboxylates, a process for preparing them and the use thereof as antiulcer-antisecretive-buffering drugs.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: January 22, 1985
    Assignee: Camillo Corvi S.p.A.
    Inventor: Camillo C. Mora
  • Patent number: 4493833
    Abstract: Preparation of pharmaceutical composition comprising, treatment of human and animal diseases with, and compound of, 3,7-disubstituted-3-cephem-4-carboxylic acid.
    Type: Grant
    Filed: August 25, 1981
    Date of Patent: January 15, 1985
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Takashi Masugi, Hisashi Takasugi, Hiromu Kochi
  • Patent number: 4492692
    Abstract: A cephalosporin derivative of the formula: ##STR1## in which R.sup.0 is a hydrogen atom or a methyl radical, R.sup.1 is any one of the C-3 substituents from antibacterially-active cephalosporins known in the art; R.sup.2 is any one of the C-4 substituents from antibacterially-active cephalosporins known in the art; R.sup.3 is a hydrogen atom or a 1-6C alkoxy or 1-6C alkylthio radical; X.sup.1 is a sulphur or oxygen atom, a CH.sub.2 radical or a radical of the formula NR.sup.7 in which R.sup.7 is a hydrogen atom, a 1-6C alkyl, formyl or benzyl radical; X.sup.2 is a nitrogen atom or a radical of the formula N.sup..sym. -R.sup.7 ; R.sup.4 and R.sup.7, and R.sup.5 and R.sup.6 are a variety of substituents which are described in the specification; and the pharmaceutically-acceptable acid- or base-addition salts thereof. Pharmaceutical compositions, manufacturing processes and intermediates are also described.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: January 8, 1985
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Frederic H. Jung, Gareth M. Davies
  • Patent number: 4492694
    Abstract: 7-(3-Indolyl)glycylamido cephalosporins have good gram positive activity and favorable pharmacokinetics and are orally effective.
    Type: Grant
    Filed: April 12, 1983
    Date of Patent: January 8, 1985
    Assignee: Eli Lilly and Company
    Inventors: Larry C. Blaszczak, Jan R. Turner
  • Patent number: 4492792
    Abstract: A process for preparing a 4-amino-5-dialkoxymethylpyrimidine derivative of the formula: ##STR1## which comprises reacting a propanenitrile derivative represented by the formula (I) or the novel compound represented by formula (II): ##STR2## with an amidine of the formula: ##STR3## wherein R.sup.1 to R.sup.6 are as defined in the specification. Also disclosed is a process for making the novel compounds of formula (II).
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: January 8, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kozo Fujii, Keigo Nishihira, Hiroyuki Sawada, Shuji Tanaka, Mamoru Nakai, Hiroshi Yoshida, Teruhiko Inoue
  • Patent number: 4492699
    Abstract: These are described compounds of formula (I) ##STR1## or an acid addition salt thereof; in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, halogen, C.sub.1-4 haloalkyl, nitro, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylthio or phenylsulphonyl; in which R.sup.5 is a group of the formula ##STR2## where R.sup.7 is hydrogen or C.sub.1-6 alkyl, R.sup.8 is hydrogen or C.sub.1-4 alkyl and n is 0 or 1, provided that when R.sup.7 is hydrogen n is 0; and in which R.sup.6 is attached to the 1, 2 or 3 position of the triazole ring and is hydrogen, C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, phenyl, benzyl or acyl. These compounds are pharmaceutically active and are especially useful in the treatment of disorders of the central nervous system. They are prepared by reacting an amine of formula R.sup.
    Type: Grant
    Filed: October 13, 1983
    Date of Patent: January 8, 1985
    Assignee: Lilly Industries Limited
    Inventors: Jiban K. Chakrabarti, Terrence M. Hotten, David J. Steggles