The Nitrogen Is Bonded Directly To A -c(=x)- Group, Wherein X Is Chalcogen Patents (Class 549/441)
  • Patent number: 5407902
    Abstract: A methoxyiminoacetic acid derivative represented by the following formula (I): ##STR1## wherein X represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; A represents a methoxy group or a methylamino group; when A is a methoxy group, B represents --O--CO-- or --N=C(R.sup.1)-- and when A is a methylamino group, B represents --O--CR.sup.1 R.sup.2 --, wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group; and Ar represents an optionally substituted aryl group or an optionally substituted heteroaryl group, and an agricultural/horticultural fungicide containing the same as an active ingredient.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: April 18, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Masatsugu Oda, Manabu Katsurada, Hirofumi Tomita
  • Patent number: 5382595
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: January 17, 1995
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5378727
    Abstract: Novel substituted heterocyclic derivatives are provided which inhibit platelet aggregation. This invention also pertains to pharmaceutical compositions and methods of using such derivatives.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: January 3, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Philippe R. Bovy, Joseph G. Rico, Thomas E. Rogers, Foe S. Tjoeng, Jeffery A. Zablocki
  • Patent number: 5356924
    Abstract: Compounds of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each independently represents a halogen atom or an alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, alkenoxy, cyano or nitro group; R.sub.3 and R.sub.4 each independently represents a hydrogen atom or an alkyl group; R.sub.5 represents a hydrogen atom, or an alkyl, alkoxy or alkoxycarbonylalkyl group; X and Y each independently represents an oxygen or sulphur atom or a group N--R, in which R is a hydrogen atom or an alkyl group; n is 0-3; r is 0 or 1; m is 0-4; and A or B represents a group of the general formula: ##STR2## wherein R.sub.6 represents a hydrogen or halogen atom, or an alkyl group; and R.sub.7 represents a halogen atom or an alkyl group; the other of A and B being a hydrogen atom or as for R.sub.1 or R.sub.2, have useful pesticidal activity.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: October 18, 1994
    Assignee: Shell Research Limited
    Inventors: Martin Anderson, Antony G. Brinnand, Roger E. Woodall
  • Patent number: 5292901
    Abstract: A new benzodioxole derivative has a substituent in the phenyl ring which is a carboxyalkylthioalkyl or the like and is effective to treat a liver disease.
    Type: Grant
    Filed: February 6, 1992
    Date of Patent: March 8, 1994
    Assignee: Eisai Co., Ltd.
    Inventors: Yoshitake Ogata, Makoto Ikeda, Seiichiro Nomoto, Makoto Okita, Naoyuki Shimomura, Toshihiko Kaneko, Takashi Yamanaka, Ieharu Hishinuma, Junichi Nagakawa, Kazuo Hirota, Kaname Miyamoto, Toru Horie, Tsuneo Wakabayashi
  • Patent number: 5242944
    Abstract: The present invention provides novel phenylacetamide derivatives having the following formula ##STR1## wherein: X is a hydrogen, halogen, hydroxy, nitro, amino, R.sup.1, NR.sup.1 R.sup.2, NHR.sup.1 or OR.sup.1 wherein R.sup.1 and R.sup.2 are an optionally substituted C.sub.1-8 alkyl, cycloalkyl or benzyl group, respectively; Y, which may be the same or different when p is greater than 1, is a hydrogen, halogen, methylenedioxy, hydroxy, trifluoromethyl, R.sup.3 or OR.sup.3 wherein R.sup.3 is an optionally substituted C.sub.1-8 alkyl or benzyl group;n is an integer from 1 to 6; andp is an integer from 1 to 5; and pharmaceutically acceptable salts thereof which have powerful analgesic and anti-inflammatory activities.The invention also provides processes for preparing these compounds and pharmaceutical compositions containing them as an active ingredient.
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: September 7, 1993
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: No S. Park, Deok C. Ha, Joong K. Choi, Hyun S. Kim, Mi S. Hong, Hee J. Lim, Kwang S. Lee
  • Patent number: 5220050
    Abstract: This invention relates to having the following formula ##STR1## or a pharmaceutically acceptable salt which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidines derivatives.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: June 15, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Philippe R. Bovy, Dudley E. McMackins, Joseph G. Rico, Foe S. Tjoeng, Mihaly V. Toth, Robert B. Garland, Masateru Miyano, Jeffery A. Zablocki
  • Patent number: 5202351
    Abstract: A novel 1-phenylalkyl-3-phenylurea derivative represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.5 represent independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.5 alkoxyl or halo; R.sup.2 represents hydrogen or C.sub.1 -C.sub.15 alkyl; R.sup.3 represents C.sub.1 -C.sub.15 alkyl or R.sup.3 represents together with R.sup.2 C.sub.2 -C.sub.9 alkylene; R.sup.4 and R.sup.5 represent independently C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxyl or halo; X represents oxygen or sulfur; Y represents --O--(CH.sub.2).sub.l --O-- wherein l is an integer of 1 to 3 or --(CH.sub.2).sub.p -- wherein p is an integer of 3 to 5; m is 0 or an integer of 1 to 5; and n is 0 or an integer of 1 to 3, is provided. The 1-phenylalkyl-3-phenylurea derivative (I) have the action of reducing cholesterol in blood by ACAT inhibition, and therefore, useful for treating hyperlipemia and atherosclerosis.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: April 13, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Sekiya, Shinya Inoue, Chiaki Hyodo, Hiromi Okushima, Kohei Umezu, Kazuo Suzuki
  • Patent number: 5202349
    Abstract: Substituted phenylacetylenes of the formula ##STR1## wherein one of the groups R.sub.1 is a hydrogen atom and the other represents the group of the formula ##STR2## in which R.sub.3 is hydrogen, methyl or ethyl and R.sub.4 is a methyl or an amino group and wherein R.sub.2 represents mono- or binuclear aromatic or heterocyclic residues containing sulfur, nitrogen or oxygen as hetero atoms and optionally being substituted by 1 to 3 substituents as defined, which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes.The compounds may be prepared by reacting a compound of the formula ##STR3## wherein R.sub.2 has the same meaning as above and one of the groups R.sub.7 is a hydrogen atom and the other represents the group of the formula --COR.sub.3, with hydroxylamine to form the oxime which then is reduced to the corresponding hydroxylamine compound into which the group of the formula --COR.sub.4 is introduced.
    Type: Grant
    Filed: July 18, 1991
    Date of Patent: April 13, 1993
    Assignee: Gruenenthal GmbH
    Inventors: Oswald Zimmer, Werner Vollenberg, Ulrich Seipp, Werner Englberger, Michael Haurand, Brigitte J. Bosman, Johannes Schneider
  • Patent number: 5194628
    Abstract: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 l in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 l is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: March 16, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
  • Patent number: 5162367
    Abstract: Insecticidal and acaricidal compounds of FormulaAR(CH.sub.2).sub.x O(CH.sub.2).sub.m A(CH.sub.2).sub.n (CE.sup.1 =CE.sup.2).sub.a (CE.sup.3 =CE.sup.4)CONR.sup.1 R.sup.2 (I)whereinAr is phenyl or naphthyl, in either case optionally substituted by one or more of optionally substituted C.sub.1-6 alkyl, optionally substituted C.sub.1-6 -alkylthio or C.sub.1-6 alkylthiooxy, halogen or optionally substituted C.sub.1-6 alkoxy,x=0 or 1m=1 to 7n=1 to 7A=CH.sub.2 or oxygena=0 or 1R.sup.1 and R.sup.2 are independently selected from hydrogen, C.sub.1-6 alkyl and C.sub.3-6 cycloalkyl (either of which may be substituted by one or more of halo, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, CF.sub.2-6 alkoxy, C.sub.2-6 alkynyl, dioxalanyl and C.sub.3-6 cycloalkyl)E.sup.1, E.sup.2, E.sup.3 and E.sup.4 are independently selected from hydrogen, C.sub.1-4 alkyl, optionally substituted by halo, and nitrile, provided that at least one of E.sup.1, E.sup.2, E.sup.3 and E.sup.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: November 10, 1992
    Assignee: The Wellcome Foundation Limited
    Inventors: Robert J. Blade, John E. Robinson
  • Patent number: 5047417
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydrogen or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: September 10, 1991
    Assignee: Eisai Co. Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5030738
    Abstract: To synthesize molecules with antiulcer action, specifically ranitidine, niperotidine and cimetidine, having the formula: ##STR1## wherein R.sub.1 is hydrogen or together with R.sub.2 represents the rest of a cycloaliphatic or heterocyclic optionally substituted ring with 5 or 6 carbon atoms, R.sub.2 represents H, alkyl, alkyl substituted with a simple or substituted aromatic ring or with a single or substituted heterocyclic ring, Ar represents a simple or substituted phenyl group, a simple or substituted heterocyclic aromatic group, N=1, 2, 3, 4, 5 or 6 and X represents CH--NO.sub.2, S, N--C.tbd.N, the compound (II) is prepared through the following process sequence: ##STR2## wherein Z=H, NO.sub.2, halogen and R.sub.3 =--(CH.sub.2).sub.n Ar, --(CH.sub.2).sub.n --SH, --(CH.sub.2).sub.n --S--S--(CH.sub.2).sub.n, --(CH.sub.2).sub.n --S--CH.sub.2 Ar Y being halogen.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: July 9, 1991
    Assignee: Janus Farmaceutici S.r.l.
    Inventor: Alberto Reiner
  • Patent number: 5028256
    Abstract: A composition for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides contains as active ingredient an acylamine derivative of the formula I ##STR1## wherein X is oxygen, sulfur, --SO-- or --SO.sub.2 --,Q is an alkyl, alkenyl, alkinyl group, which may be interrupted by oxygen sulfur sulfonyl or sulfonyl, or a test 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-4-alkyl, 2,2-dialkyl-1,3-dioxolan-4-ylalkyl, 1,3-dioxan-2-ylalkyl, 2-benzopyranylalkyl, alkoxycarbonyl alkenyloxycarbonyl or tetrahydrofurylalkyl, or the groupQ--X represents also a halogenoalkyl radical,n is 1, 2 or 3,Z is hydrogen, halogen, alkyl or dioxymethylene, alkoxy, alkenyloxy or alkinyloxy, A is a C.sub.1 -C.sub.8 -hydrocarbon radical which may be straight-chained, branched or cyclic and which is unsubstituted or substituted by alkoxy, alkylthio, cyano or halogen,R is halogenoalkyl or halogenoalkenyl,R.sub.1 is hydrogen, a C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl or C.sub.3 -C.sub.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: July 2, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Martin
  • Patent number: 5013734
    Abstract: The esters of phenylalkanoic acid of the formula: ##STR1## wherein R.sup.1 is 4-10 membered, saturated or unsaturated, mono- or bi-cyclic hetero ring containing as hetero atoms:(i) one or two nitrogen,(ii) two or three of nitrogen and sulfur in total, or(iii) one or two sulfur;R.sup.2 is hydrogen; orR.sup.1 and R.sup.2, taken together with a nitrogen to which they are attached, form 4-7 membered, saturated or unsaturated, mono-cyclic hetero ring containing as hetero atoms:(i) one or two nitrogen, or(ii) two or three of nitrogen and oxygen in total,the aforementioned hetero rings, represented by R.sup.1 or formed by R.sup.1 and R.sup.2, taken together with a nitrogen to which they are attached, may be substituted by one substituent selected from C1-4 alkyl and C2-5 acyl;R.sup.3 each, independently, is hydrogen or C1-4 alkyl;R.sup.4 is hydrogen, halogen, trihalomethyl, C1-4 alkyl, C1-4 alkoxy, C2-5 acyl, cyano, nitro or nitroxy;R.sup.5 each, independently, is hydrogen, C1-4 alkyl or phenyl; or the two R.sup.
    Type: Grant
    Filed: May 11, 1990
    Date of Patent: May 7, 1991
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Sadahiko Iguchi, Masanori Kawamura, Tsumoru Miyamoto
  • Patent number: 5001159
    Abstract: A compound of formula (I) ##STR1## in which: X denotes hydrogen, a halogen, a trifluoromethyl group, a C.sub.1 -C.sub.4 alkyl group or a C.sub.1 -C.sub.4 alkoxy group;R.sub.1 denotes a linear or branched C.sub.2 -C.sub.8 alkyl group, a C.sub.3 -C.sub.5 cycloalkyl group or a cycloalkylmethyl group in which the cycloalkyl moiety has from 3 to 5 carbon atoms;R.sub.2 denotes hydrogen or a C.sub.1 -C.sub.4 alkyl group;R.sub.3 denotes hydrogen, a C.sub.1 -C.sub.4 alkyl group, an optionally substituted phenylalkyl group or a pyridylalkyl group;or R.sub.2 and R.sub.3 denote, together with the nitrogen to which they are attached, a pyrrolidinyl, piperidyl, morpholinyl, perhydrothiazinyl, piperazinyl or 4-methylpiperazinyl ring; andAr denotes a phenyl group, optionally having from one to three substituents, each of which is, independently, a halogen or a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: March 19, 1991
    Assignee: Synthelabo
    Inventors: Christian Hoornaert, Jean-Claude Muller, Nigel Beeley
  • Patent number: 4968677
    Abstract: 1-Aryl-2-naphthoylamines of formula I are described ##STR1## wherein R.sub.1 is halogen, nitro, cyano, C.sub.1 -C.sub.6 alkyl that is unsubstituted or mono- or poly-substituted by halogen and/or C.sub.1 -C.sub.3 alkoxy, or is C.sub.3 -C.sub.6 cycloalkyl, OR.sub.4, NR.sub.5 R.sub.6, CO2R.sub.5, CONR.sub.5 R.sub.6 or NHCOR.sub.7, or wherein two adjacent positions in the nucleus are bridged by a methylenedioxy or ethylenedioxy group that is unsubstituted or mono- or poly-substituted by fluorine, wherein further R.sub.4 is hydrogen or C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.4 alkenyl, 2-propynyl, 3-halo-2-propynyl, ##STR2## or COR.sub.7, each of R.sub.5 and R.sub.6, independently of the other, is H or C.sub.1 -C.sub.4 alkyl, R.sub.7 is C.sub.1 -C.sub.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Riebli
  • Patent number: 4943591
    Abstract: The invention provides compounds of the general formula (I) ##STR1## wherein X represents a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain andY represents a bond, or a C.sub.1-4 alkylene, C.sub.2-4 alkenylene or C.sub.2-4 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is not more than 8;Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms or the groups C.sub.1-3 alkyl, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, C.sub.1-3 alkoxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom, or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O-- or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: July 24, 1990
    Assignee: Glaxo Group Limited
    Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor, Ian B. Campbell
  • Patent number: 4937360
    Abstract: N-substituted amide derivative represented by the formula ##STR1## wherein A is --CH(OH)-- or --C(.dbd.O)--, R.sup.1 is a hydrogen atom or an lkyl group having 1 to 3 carbon atoms, and R.sup.2 is an alkyl group having 1 to 6 carbon atoms, are disclosed. These compounds are useful for prevention and therapy for liver diseases.
    Type: Grant
    Filed: June 28, 1989
    Date of Patent: June 26, 1990
    Assignees: Taisho Pharmaceutical Co., Ltd., The Institute of Materia Medica of Chinese Academy of Medical Sciences
    Inventors: Geng-tao Liu, Liang Huang, Er-chang Rao, Jin Zhou, Yan Li, Katsuo Hatayama, Tatsuhiko Sano, Kensei Yoshikawa, Shohei Higuchi, Iwao Arai
  • Patent number: 4929741
    Abstract: Propiolophenone derivatives of the formula ##STR1## wherein R.sup.6 is hydrogen, lower alkyl or a group of the formula ##STR2## as well as corresponding hydroxy compounds of the formula ##STR3## wherein R.sup.6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula--C(R.sup.14)(R.sup.15)OR.sup.16' (f'):exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.
    Type: Grant
    Filed: March 17, 1988
    Date of Patent: May 29, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Albert Fischli, Eva-Maria Gutknecht, Daniel Obrecht
  • Patent number: 4912221
    Abstract: The instant invention relates to optically pure, L-(S)forms of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid compounds and their method of preparation from optionally pure L-phenylalanine precursor compounds and their preparation utilizing novel in situ cationic catalyst systems.
    Type: Grant
    Filed: October 27, 1988
    Date of Patent: March 27, 1990
    Assignee: Occidental Chemical Corporation
    Inventors: Neil J. O'Reilly, Henry C. Lin
  • Patent number: 4908386
    Abstract: The present invention provides compounds of general formula (I) ##STR1## wherein Ar represents an unsubstituted or substituted phenyl gorup;R.sup.1 and R.sup.2 each represents a hydrogen atom or a C.sub.1-3 alkyl group;X represents a bond or a C.sub.1-7 alkylene, C.sub.2-7 alkenylene or C.sub.2-7 alkynylene chain;Y represents a bond or a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain;Q represents a substituted phenyl or pyridyl ring;and physiologically acceptable salts and solvates thereof useful as stimulants of .sub.2 -adrenoreceptors and particularly in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.
    Type: Grant
    Filed: December 20, 1988
    Date of Patent: March 13, 1990
    Assignee: Glaxo Group Limited
    Inventors: Harry Finch, Lawrence H. C. Lunts, Alan Naylor, Ian F. Skidmore, Ian B. Campbell, David Middlemiss, Charles Willbe
  • Patent number: 4897109
    Abstract: A composition for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides contains as active ingredient an acylamine derivative of the formula I ##STR1## wherein X is oxygen, sulfur, --SO-- or --SO.sub.2 --,Q is an alkyl, alkenyl, alkinyl group, which may be interupted by oxygen, sulfur, sulfinyl or sulfonyul, or a test 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-4-alkyl, 2,2-dialkyl-1,3-dioxolan-4-ylalkyl, 1,3-dioxan-2-ylalkyl, 2-benzopyranylalkyl, alkoxycarbonyl alkenyl-oxycarbonyl or tetrahydrofurylalkyl, or the groupOX represents also a halogenoalkyl radical,n is 1, 2 or 3,Z is hydrogen, halogen, alkyl or dioxymethylene,A is a C.sub.1 -C.sub.8 -hydrocarbon radical which may be staight-chained, branched or cyclic and which is unsubstituted or substituted by alkoxy, alkylthio, cyano or halogen,B is hydrogen, a C.sub.1 -C.sub.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: January 30, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Martin
  • Patent number: 4840967
    Abstract: A compound which is a carbamate or urea derivative of general formula (I) ##STR1## wherein X is hydrogen, halogen or methylthio,Y is oxygen or ##STR2## R is C.sub.1 -C.sub.4 alkyl, R.sub.1 is hydrogen, one or two halogen atoms or trifluoromethyl groups, a methyl group, a methyl group, a cyano group, a nitro group, a methoxycarbonyl group, a methylenedioxy group linked to two adjacent carbon atoms of the benzene ring to which it is attached, or a fused benzo group forming an .alpha.-naphthyl or .beta.-naphthyl group with the benzene ring to which it is attached,R.sub.2 is a linear or branched C.sub.1 -C.sub.8 alkyl or alkenyl group optionally substituted with halogen atoms or a methoxy group, a cyclopropylmethyl group, or a phenyl group optionally substituted with one or two halogen atoms or methyl groups,n is 1 or 2, andm is 2 or 3, or an addition salt thereof with a pharmacologically acceptable acid is pharmacologically active as a calcium antagonist.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: June 20, 1989
    Assignee: Synthelabo
    Inventors: Nigel Beeley, Gerard Cremer
  • Patent number: 4822775
    Abstract: The invention relates to novel substituted tyrosyl alanine dipeptide amides of the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein R.sup.1 is hydrogen, lower alkyl, hydroxy, --OCO.sub.2 lower alkyl, lower alkoxy, --O(CH.sub.2).sub.n -phenyl with the phenyl optionally substituted by halogen, --NO.sub.2, --CN, --NH.sub.2 or lower alkyl wherein n is 1 to 4; R.sup.2 and R.sup.3 represent lower alkyl, halogen, or lower alkoxy, or either one of R.sup.2 or R.sup.3 is hydrogen and the other is lower alkyl, lower alkoxy or halogen; R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 may be the same or different and represent hydrogen or lower alkyl; R.sup.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: April 18, 1989
    Assignee: G. D. Searle & Co.
    Inventors: Donald W. Hansen, Jr., Barnett S. Pitzele, Michael Clare, Robert W. Hamilton
  • Patent number: 4820828
    Abstract: The present invention relates to cinnamohydroxamic acids. These compounds inhibit 5-lipoxygenase and are useful as bronchodilators.
    Type: Grant
    Filed: March 4, 1987
    Date of Patent: April 11, 1989
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: James P. Demers, William V. Murray, Richard B. Sulsky
  • Patent number: 4755619
    Abstract: Compounds of formula (II) ##STR1## wherein R.sub.1 and R.sub.2 are each separately selected from hydrogen, alkyl, alkenyl and alkynyl groups having up to a maximum of four carbon atoms and being unsubstituted, and alkyl, alkenyl and alkynyl groups having up to a maximum of three carbon atoms and being substituted by one, or in the case of fluoro by one or more, substitutents but with the proviso that when R.sub.1 is hydrogen then R.sub.2 is hydrogen or methyl, or R.sub.1 and R.sub.2 together constitute an ethylene bridging group, and R.sub.3 is a group which under physiological conditions undergoes elimination with the formation of a 3,5-dioxopiperazinyl ring, with the further proviso that the compound is in the meso or erythro configuration when each of R.sub.1 and R.sub.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: July 5, 1988
    Assignee: National Research Development Corporation
    Inventors: Andrew M. Creighton, William A. Jeffery
  • Patent number: 4730008
    Abstract: The invention provides compounds of the general formula (I) ##STR1## wherein Ar, R.sup.1, R.sup.2, X, Y and Q are defined in the specification and physiologically acceptable salts and solvates thereof.The compounds have a selective stimulant action at .beta..sub.2 -adrenoreceptors and may be used, inter alia, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.
    Type: Grant
    Filed: January 10, 1986
    Date of Patent: March 8, 1988
    Assignee: Glaxo Group Limited
    Inventors: Ian F. Skidmore, Harry Finch, Alan Naylor, Lawrence H. C. Lunts, Ian B. Campbell
  • Patent number: 4725602
    Abstract: Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: February 16, 1988
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • Patent number: 4701541
    Abstract: The compounds 1-(3,4-methylenedioxyphenyl)-3-(N-benzylamino)butane and methyl 5-[[4-(3,4-methylenedioxyphenyl)-N-benzyl-2-butylamino]acetyl]salicylate are intermediates in the preparation of medroxalol.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: October 20, 1987
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Richard E. Donaldson, John F. Hoops
  • Patent number: 4697024
    Abstract: The compounds 1-(3,4-methylenedioxyphenyl)-3-(N-benzylamino)butane and methyl 5-[[4-(3,4-methylenedioxyphenyl)-N-benzyl-2-butylamino]acetyl]salicylate are intermediates in the preparation of medroxalol.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: September 29, 1987
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Richard E. Donaldson, John F. Hoops
  • Patent number: 4675439
    Abstract: A process for preparing an N-acylphenylalanine represented by the formula (II): ##STR1## wherein R.sub.3 and R.sub.4 mean individually a hydrogen atom or an alkyl, alkoxy, phenoxy, hydroxy or methylenedioxy group, and R denotes a methyl or phenyl group, which comprises catalytically reducing an N-acyl-.beta.-phenylserine represented by the formula (I): ##STR2## wherein R.sub.1 and R.sub.2 mean individually a hydrogen atom or an alkyl, alkoxy, phenoxy, benzyloxy or methylenedioxy group, and R has the same meaning as defined in the formula (II), in the presence of a reducing catalyst or both reducing catalyst and acid, in a solvent.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: June 23, 1987
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
  • Patent number: 4612388
    Abstract: Disclosed herein is a process for producing an N-acyl-substituted or unsubstituted phenylalanine comprising hydrolyzing a 2-substituted-4-substituted or unsubstituted benzylidene-5-oxazolone with alkali, adjusting pH of the reaction solution containing its hydrolysis product with acid at 5-9 and reducing the resultant reaction solution catalytically in the presence of a palladium or platinum reducing catalyst.In accordance with the process of the present invention, time duration required for effecting the reduction can be shortened markedly in comparison with the reduction in an aqueous strong alkaline solution. Moreover, the catalyst recovered after completion of the reduction can be used repeatedly without any additional treatment and without any observed lowering in its activity. Accordingly, the reduction using the recovered catalyst may proceed in practically the same time as in the case of using a fresh catalyst.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: September 16, 1986
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
  • Patent number: 4612313
    Abstract: The present invention provides phenylacetonitrile derivatives of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5, which can be the same or different, are hydrogen or haolgen atoms or alkyl, alkoxy, nitro, amino or acylamino radicals and two adjacent substituents can together also form a methylenedioxy or ethylenedioxy radical, A is a radical of the general formula: ##STR2## in which R.sub.6 is a straight-chained, cyclic or branched, saturated or unsaturated alkyl radical containing 2 to 12 carbon atoms, R.sub.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: September 16, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Herbert Leinert, Wolfgang Kampe, Klaus Strein, Bernd Muller-Beckmann, Wolfgang Bartsch
  • Patent number: 4605667
    Abstract: Pesticidal water-soluble aminoacid sulfenylated carbamates useful as broad spectrum insecticides and miticides, particularly useful as systemic insecticides.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: August 12, 1986
    Assignee: Union Carbide Corporation
    Inventors: Chennupati K. Rao, Themistocles D. D'Silva
  • Patent number: 4602023
    Abstract: The present invention provides various novel diphenic acid monoamide compounds, novel pharmaceutical compositions and methods of use thereof, as well as novel methods of synthesis therefor. The novel diphenic acid monoamides of the present invention are leukotriene antagonists, 5-lipoxygenase inhibitors, and mediator release inhibitors providing activity useful for treating asthma, allergies, cardiovascular diseases, migraines, and immunoinflammatory conditions.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: July 22, 1986
    Assignee: Warner-Lambert Company
    Inventors: John S. Kiely, Suchin Huang
  • Patent number: 4556649
    Abstract: Insecticidally active novel substituted malonic acid diamide insecticides of the formula ##STR1## wherein R.sup.1 represents aryl or heteroaryl, each of which can optionally be substituted,R.sup.2 represents hydrogen or trialkylsilyl, and represents alkyl, cycloalkyl, alkenyl, alkinyl, aralkyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphenyl, arylsulphenyl, alkylsulphonyl, arylsulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, arylaminosulphonyl or arylalkylaminosulphonyl, each of which can optionally be substituted, and represents radicals of the formula--CO--NR.sup.5 R.sup.6whereinR.sup.5 and R.sup.6 independently of one another represent hydrogen, alkyl, cycloalkyl, aryl, alkylaminocarbonyl, arylaminocarbonyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphonyl or arylsulphonyl, it being possible for these radicals to be optionally substituted,R.sup.3 represents hydrogen or the radical R.sup.4,R.sup.7 and R.sup.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: December 3, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Salzburg, Rudolf Fauss, Kurt Findeisen, Bernhard Homeyer
  • Patent number: 4551472
    Abstract: Unsymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4535090
    Abstract: 3,5-diphenyl-1H-1,2,4-triazoles with contragestational activity of the following formula ##STR1## wherein R may be located on one or the other of the two adjacent nitrogen atoms and may represent hydrogen or a group R.sub.5 CO-- wherein R.sub.5 is an aliphatic saturated or unsaturated hydrocarbyl containing from 1 to 20 carbon atoms, R.sub.1, R.sub.2 and R.sub.3, each independently are selected from hydrogen, lower alkyl and lower alkoxy or R.sub.2 and R.sub.3 together may represent a methylenedioxy group, and R.sub.4 is an aliphatic saturated or unsaturated hydrocarbyl group of from 1 to 20 carbons, with the proviso that when R is hydrogen or an R.sub.5 CO-- group wherein R.sub.5 contains 4 or less carbon atoms, R.sub.4 must contain 5 or more carbons.These compounds have proven to be highly effective in terminating pregnancy in several animal species after a single parenteral injection.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: August 13, 1985
    Assignee: Gruppo Lepetit S.p.A.
    Inventors: Giulio Galliani, Amedeo Omodei-Sale, Pietro Consonni, Alessandro Assandri
  • Patent number: 4502994
    Abstract: A novel enantiomeric synthesis from ascorbic acid of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-azetidinone-1-sulfate, an intermediate for an antibiotic compound.
    Type: Grant
    Filed: December 9, 1982
    Date of Patent: March 5, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Chung-Chen Wei, Manfred Weigele
  • Patent number: 4480109
    Abstract: A process for producing an optically active threo-3-(3,4-dihydroxyphenyl)serine represented by the formula ##STR1## which is useful as a remedy for peripheral orthostatic hypotension or as an antidepressant, which process comprises treating threo-3-(3,4-methylenedioxyphenyl)serine or an N-carbobenzoxy derivative thereof represented by the formula ##STR2## wherein A represents a hydrogen atom or a carbobenzoxy group, with a Lewis acid to form threo-3-(3,4-dihydroxyphenyl)serine or an N-carbobenzoxy derivative thereof represented by the formula ##STR3## wherein A is as defined above, and, if A is a carbobenzoxy group, catalytically reducing the resulting compound of formula [2]; a racemic or optically active threo-N-carbobenzoxy-3-(3,4-methylenedioxyphenyl)serine represented by the formula ##STR4## which is a novel compound useful as an intermediate in the above synthesis; and a process for producing said novel compound.
    Type: Grant
    Filed: January 3, 1983
    Date of Patent: October 30, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naohito Ohashi, Shoji Nagata, Kikuo Ishizumi
  • Patent number: 4418069
    Abstract: The present invention is related to new benzisoselenazolones having the general formula I ##STR1## new products having the general formula II ##STR2## used as intermediary products in the production of the compounds of formula I and a method for the treatment of rheumatic diseases using a compound of formula I as active agent.
    Type: Grant
    Filed: July 9, 1981
    Date of Patent: November 29, 1983
    Assignee: A. Nattermann & Cie GmbH
    Inventors: Andre Welter, Leon Christiaens, Ferdinand Wirtz-Peitz
  • Patent number: 4390710
    Abstract: Aromatic esters of carbamic acid derivatives, e.g., p-chlorophenyl-N-methyl carbamate, are prepared by reaction of the corresponding aromatic alcohol, e.g., p-chlorophenol, and monoisocyanate, e.g., methyl isocyanate, in the presence of a catalytic amount of a combination of a 4-aminopyridine catalyst, e.g., 4-dimethylaminopyridine, and pyridine or methyl substituted pyridines. The product is substantially pure, having less than 0.80 weight percent allophanate ester by-product, e.g., p-chlorophenyl-N,N'-dimethyl allophanate, and less than 0.50 weight percent unreacted aromatic alcohol, e.g., p-chlorophenol. The reaction is readily controlled and characterized by the substantial absence of reflux. The product can be retained in the liquid state at reaction temperature for extended periods of time without significantly increasing the level of allophanate ester by-product.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: June 28, 1983
    Assignee: PPG Industries, Inc.
    Inventor: James A. Manner
  • Patent number: 4386031
    Abstract: The present invention refers to N-Benzoyl-.omega.
    Type: Grant
    Filed: November 6, 1981
    Date of Patent: May 31, 1983
    Assignee: A. Nattermann & Cie GmbH
    Inventors: Gerd Hilboll, Hans-Heiner Lautenschlager, Brigitte Stoll, Manfred Probst
  • Patent number: 4381935
    Abstract: Oximecarbamate derivatives of the formula: ##STR1## wherein R.sub.1 is methyl or methoxy, R.sub.2 is lower alkyl, lower alkoxy, methylenedioxy, methylthio, halogen or trifluoromethyl, R.sub.3 is hydrogen, methyl or ethyl, X and Z are each oxygen or sulfur, m is an integer of 0 to 5 when R.sub.2 is fluorine or an integer of 0 to 3 when R.sub.2 is other than fluorine, R.sub.2 being same or different in case of m being an integer of 2 or 3, n and r are each an integer of 0 or 1 but when one of them is zero, the other is not zero, q is an integer of 0 or 1 and t is an integer of 0 to 4, which are useful as herbicides having high selectivity to crop plants.
    Type: Grant
    Filed: November 3, 1981
    Date of Patent: May 3, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiaki Kosuge, Ryo Yoshida, Seizo Sumida, Hirofumi Oshita, Soji Otsuki, Katsuzo Kamoshita
  • Patent number: 4377593
    Abstract: The invention relates to .alpha.-isopropyl- and .alpha.-cyclopropylphenylacetates of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, allenyl, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl, R.sub.2 is unsubstituted or substituted alkenyl or alkynyl, R.sub.3 is isopropyl or cyclopropyl, and each of R.sub.4 and R.sub.5 is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, or both together are the methylenedioxy radical.A process for the production of these compounds and their use in pest control are disclosed.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: March 22, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
  • Patent number: RE32944
    Abstract: Novel aromatic carboxylic amides of the general formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is a hydrogen atom or an alkyl group having 1-4 carbon atoms, R.sub.3 and R.sub.4 are hydrogen atoms or together form another chemical bond, each X is a hydroxyl group, a halogen atom, an alkyl group having 1-4 carbon atoms and an alkoxy group containing 1-4 carbon atoms, and n is an integer of 1-3 with the proviso that when .[.Xs.]. .Iadd.X's .Iaddend.are alkyl or alkoxy groups, they may be connected together to form a ring, as well as pharmaceutically acceptable salts thereof.These compounds possess a strong antiallergenic action and are thus useful for treatment of asthma, hay fever, .[.anticaria.]. .Iadd.urticaria .Iaddend.and atopic dermatitis.The above aromatic carboxylic amides can be prepared by reacting a reactive functional derivative of the general formula: ##STR2## where R.sub.1, R.sub.2, R.sub.3, R.sub.
    Type: Grant
    Filed: June 1, 1977
    Date of Patent: June 6, 1989
    Assignee: Kissei Yakuhin Kogyo Kabushiki
    Inventors: Kozaburo Harita, Yukiyoshi Ajisawa, Kinji Iizuka, Yukihiko Kinoshita, Tetsuhide Kamijo, Michihiro Kobayashi