Plural Acyclic Nitrogens Bonded Directly To The Same Carbon Or Single Bonded Directly To Each Other Patents (Class 546/306)
  • Patent number: 5053504
    Abstract: A process is disclosed for providing benzazepine intermediates of the formulae ##STR1## wherein R.sub.3, R.sub.4 and Y are as defined herein, which intermediates are useful in a process for the preparation of pharmaceutically useful benzazepine derivatives.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: October 1, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Wen-Sen Li, John K. Thottathil, Michael Murphy
  • Patent number: 5008276
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: April 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 5006539
    Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1]heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: April 9, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4996318
    Abstract: The amino-9,10-secosteroids ##STR1## of the present invention contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain and are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: February 26, 1991
    Assignee: The Upjohn Company
    Inventors: Martin Gall, Robert I. Higuchi
  • Patent number: 4994473
    Abstract: Insecticides of the general formula ##STR1## wherein R.sub.1 is an optionally substituted 5- to 10-member heterocyclic moiety; R.sub.2 is an optionally substituted alkyl, cycloalkyl or alkenyl moiety; X is oxygen, sulfur or --NH--; and R.sub.3 is: (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl, 3-(pyridyloxy)phenalkyl, 3-phenylaminophenoalkyl, 3-benzylphenalkyl or 3-benzyloxyphenalkyl moiety; (b) a benzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl or tetrafluorobenzyl moiety; (d) 4-phenoxy-2-butyn-2-yl; or (e) 2-methyl-3-phenylbenzyl.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: February 19, 1991
    Assignee: ICI Americas Inc.
    Inventor: Michael D. Broadhurst
  • Patent number: 4990507
    Abstract: The invention relates to a pharmaceutical composition as a therapeutic agent for ischemic disease comprising a compound of the formula ##STR1## wherein R.sup.1 is carbamoyl substituted with morpholino (lower) alkyl, thiomorpholino(lower)alkyl or lower alkylamino(lower)alkyl; or ureido substituted with lower alkylamino(lower)alkyl; andR.sup.2 is phenyl substituted with nitro, andR.sup.4 is lower alkyl; orR.sup.2 is lower alkyl, andR.sup.4 is phenyl substituted with nitro;with proviso that R.sup.1 is carbamoyl substituted with thiomorpholino(lower)alkyl or lower alkylamino(lower)alkyl; or ureido substituted with lower alkylamino(lower)alkyl when R.sup.4 is lower alkyl; or its salt, as an active ingredient, in association with a pharmaceutically acceptable, substantially nontoxic carrier or excipient.
    Type: Grant
    Filed: January 9, 1989
    Date of Patent: February 5, 1991
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Hisashi Takasugi, Kimio Esumi, Atsushi Kuno, Hiroyoshi Sakai, Kazuhiro Maeda, Yoshie Sakamoto
  • Patent number: 4981965
    Abstract: A base precursor in the form of a salt of an organic base with a carboxylic acid is disclosed. The organic base is a diacidic to tetraacidic base which is composed of two to four guanidine moieties and at least one linking group for the guanidine moities. The organic base is such a hydrophilic compound that the number of carbon atoms contained in the organic base is not more than six times the number of the guanidine moieties. The linking group is a residue of a hydrocarbon or a heterocyclic ring. The guanidine moiety corresponds to an atomic group formed by removing one or two hydrogen atoms from a compound having the following formula (I): ##STR1## where each of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aralkyl group, an aryl group or a heterocyclic group, each of which may have one or more substituent groups, and any two of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 1, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yoshiharu Yabuki, Jiro Tsukahara, Taku Nakamura
  • Patent number: 4962113
    Abstract: Novel pyridinium derivatives represented by the formula (I): ##STR1## wherein ##STR2## is an optionally substituted pyridinium ring; R.sup.1 is a lower alkyl group or aralkyl group;R.sup.7 and R.sup.10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group;l is 0 or 1;R.sup.5 is a phenylene group or an alkylene group which may be substituted;R.sup.11 is an alkyl group or aryl group;X is a group of the formula: --CH.sub.2 OCH.sub.2 -- or a group of the formula: ##STR3## wherein R.sup.6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3;U is a group of the formula: ##STR4## wherein R.sup.
    Type: Grant
    Filed: July 26, 1988
    Date of Patent: October 9, 1990
    Assignee: Takeda Chemical Industries, Ltd
    Inventors: Susumu Tsushima, Muneo Takatani, Kohei Nishikawa
  • Patent number: 4954628
    Abstract: The invention relates to a process for preparing sulphonyl-ureas of the general formula (I) ##STR1## wherein Ar.sub.1 represents a phenyl, naphthyl or thienyl group, the derivatives thereof substituted by C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, (halo)alkoxycarbonyl, (halo)alkyloxy, nitro, cyano groups as well as by halogen atoms,Ar.sub.2 represents a phenyl, pyridyl, pirimidinyl or triazinyl group and the derivatives thereof substituted by C.sub.1-4 (halo)alkyl, C.sub.1-4 (halo)alkyloxy, amino, O-acyl, O-arylsulphonyl, O-(substituted carbamoyl) groups as well as by halogen atoms.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: September 4, 1990
    Assignees: Nitrokaelepek, Magyar Tudomanyos Akademia Kozponti Kemiai Kutato Intezete
    Inventors: Gabor Besenyei, Sandor Nemeth, Laszlo Simandi, Maria Belak, Maria Szabo, Jozsef Dukai, Lajos Nagy, Elemer Tomordi, Csaba Soptei, Erzsebet E. Dioszegine
  • Patent number: 4948891
    Abstract: Compounds of the formula ##STR1## where Het is a heterocyclic group, n is an integer of 0 to 2 and R.sup.1 is hydrogen or lower alkyl are protease inhibitors useful as anti-plasmin and anti-thrombin agents.
    Type: Grant
    Filed: August 9, 1989
    Date of Patent: August 14, 1990
    Assignee: Pfizer Inc.
    Inventors: Rodney C. Schnur, Anton F. J. Fliri
  • Patent number: 4946854
    Abstract: Novel compounds of formula I ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3, R.sup.7, R.sup.8 and R.sup.9, independently of the others, is H or halogen,R.sup.4 is H, R.sup.10 CO-- or R.sup.11 NHCO-- wherein R.sup.10 is a C.sub.1 -C.sub.4 alkyl group which is unsubstituted or substituted by one to three identical or different substituents selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 - acyloxy and --COOG, wherein G is H, an alkali metal cation or an alkaline earth metal cation, and R.sup.11 is an unsubstituted or halo-substituted C.sub.1 -C.sub.4 alkyl or phenyl group,each of R.sup.5 and R.sup.6, independently of the other, is H, halogen, alkyl or haloalkyl andX is O, S(O)n or NH wherein n is 0, 1 or 2, the preparation of the novel compounds and their use against parasites in and on productive livestock and against insect pests, and novel starting materials and their preparation.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: August 7, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Jean-Claude Gehret, Bruno Frei
  • Patent number: 4945111
    Abstract: Fungicidal N,N'-diacylaminals of the formula ##STR1## in which R.sup.1 is optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl,R.sup.2 and R.sup.3 are hydrogen or various organic radicals, andX is oxygen or sulphur.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: July 31, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Winfried Lunkenheimer, Dieter Berg, Wilhelm Brandes
  • Patent number: 4908451
    Abstract: A process is disclosed for the preparation of .alpha.-substituted carbonyl compounds, wherein .alpha.-substituted ketone is prepared by the following reaction: ##STR1## .alpha.-azo ester is prepared by the following reaction: ##STR2## and .alpha.-hydrozono ester is prepared by the following reaction: ##STR3## wherein the .alpha.-azo ester and .alpha.-hydrazono ester obtained by the above reactions include novel compounds, which are also disclosed.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: March 13, 1990
    Assignee: Agency of Industrial Science and Technology
    Inventors: Masato Tanaka, Toshiyasu Sakakura
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • Patent number: 4874864
    Abstract: Compounds of the formula ##STR1## where HET is a heterocyclic group, n is an integer of 0 to 2 and R.sup.1 is hydrogen or lower alkyl are protease inhibitors use as anti-plasmin and anti-thrombin agents.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: October 17, 1989
    Assignee: Pfizer Inc.
    Inventors: Rodney C. Schnur, Anton F. J. Fliri
  • Patent number: 4845090
    Abstract: Diagnostic media suitable for NMR diagnoses contain compounds of Formula I ##STR1## wherein is a single bond or a double bond, X is the grouping --(CH.sub.2).sub.n -- or, if is a single bond, also the grouping --NHCO(CH.sub.2).sub.n -- wherein n means 0 to 4,m means the numbers 0, 1, or 2,R.sub.1 is an alkyl residue substituted by hydroxy groups, acyloxy groups and/or alkylidenedioxy groups,R.sub.2 has the same meanings as R.sub.1 or is a hydrogen atom or an alkyl residue,R.sub.3 and R.sub.4 are alkyl residues, andR.sub.5 and R.sub.6 are alkyl residues optionally substituted by hydroxy groups.
    Type: Grant
    Filed: September 24, 1985
    Date of Patent: July 4, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinz Gries, Ulrich Niedballa, Hanns-Joachim Weinmann
  • Patent number: 4837234
    Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.
    Type: Grant
    Filed: July 22, 1986
    Date of Patent: June 6, 1989
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4831030
    Abstract: The invention relates to compounds for treatment of hypertension, and cardiovascular and cerebrovascular diseases, which compounds are of the formula: ##STR1## wherein R.sup.1 is piperazinyl(lower)alkyl, carbamoyl substituted with piperazinyl(lower)alkyl, or piperazinylcarbonyl, in each of which a piperazinyl group may be substituted with lower alkyl, andR.sup.3 is hydrogen or halogen;R.sup.2 is phenyl substituted with nitro, andR.sup.4 is lower alkyl or halo(lower)alkyl; orR.sup.2 is lower alkyl, andR.sup.4 is phenyl substitured with nitro;and a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: May 16, 1989
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Hisashi Takasugi, Atsushi Kuno, Hiroyoshi Sakai, Yoshie Sugiyama, Takao Takaya
  • Patent number: 4831044
    Abstract: Novel fungicidal pyridyl cyclopropane carboxamidines having the general structural formula ##STR1## and tautomers thereof wherein R is selected from the group consisting of hydrogen, pyridyl, substituted pyridyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.6 alkyl, acyl, carbamoyl, sulfonyl and cyano;R.sub.1 is selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy and C.sub.2 -C.sub.3 alkenyloxy;R.sub.2 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.3 alkyl;R.sub.3 is selected from the group consisting of hydrogen, alkyl, aryl or arylalkyl;and fungicidally acceptable organic and inorganic salts thereof.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: May 16, 1989
    Assignee: ICI Americas Inc.
    Inventors: Don R. Baker, Keith H. Brownell
  • Patent number: 4818271
    Abstract: Pyridinylurea compounds of the formula ##STR1## and acid addition salts thereof; wherein R is cyclo alkyl, alkenyl, or an alkyl group optionally substituted with halogen, hydroxy, cycloalkyl, alkoxy, dialkylamino or phenyl; R.sup.1 is hydrogen or alkyl; R and R.sup.1 together with the nitrogen atom of the NRR.sup.1 group optionally define a heterocycle containing 4 to 6 ring carbon atoms; X is hydrogen, halogen, haloalkyl, alkoxy, alkylthio or alkylsulfonyl; Y is hydrogen, halogen, haloalkyl, alkoxy, alkylthio or alkylsulfonyl; and wherein the NHCONRR.sup.1 group is bonded to the pyridinyl ring in the 3- or 4-position; provided that at least one of X and Y is other than hydrogen and when both R and R.sup.1 are alkyl, R is 1,1-dimethylethyl or cyclopentyl and R.sup.1 is methyl. The compounds are useful in agriculture as plant growth regulators.
    Type: Grant
    Filed: October 31, 1985
    Date of Patent: April 4, 1989
    Assignee: FMC Corporation
    Inventor: Robert N. Henrie, II
  • Patent number: 4808722
    Abstract: Pyridinylurea N-oxides of the formula ##STR1## and acid addition salts thereof; wherein R is cycloalkyl (C.sub.3 -C.sub.8), alkenyl (C.sub.3 -C.sub.8), or an alkyl (C.sub.1 -C.sub.6) group optionally substituted with halogen, hydroxy, cycloalkyl (C.sub.3 -C.sub.8) alkoxy (C.sub.1 -C.sub.6), dialkyl (C.sub.1 -C.sub.6)amino or phenyl; R.sup.1 is hydrogen or alkyl (C.sub.1 -C.sub.6); R and R.sup.1 together with the nitrogen atom of the NRR.sup.1 group optionally define a nonaromatic heterocycle containing 4 to 6 ring carbon atoms; each X independently is halogen, alkyl (C.sub.1 -C.sub.6), haloalkyl (C.sub.1 -C.sub.6), alkoxy (C.sub.1 -C.sub.6), hydroxy, 2-pyridinyl, alkyl(C.sub.1 -C.sub.6)thio or alkyl (C.sub.1 -C.sub.6)sulfonyl; A is 1 to 4; and wherein the NHCONRR.sup.1 group is bonded to the pyridinyl ring in the 3- or 4-position. The compounds are useful in agriculture as plant growth regulators.
    Type: Grant
    Filed: October 31, 1985
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventor: Robert N. Henrie, II
  • Patent number: 4791123
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: December 13, 1988
    Assignee: Schering Akt.
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: 4787931
    Abstract: N-phenyl-N'-(pyridinyl-N-oxide)ureas of the formula ##STR1## and their use as plant regulators are disclosed and exemplified.
    Type: Grant
    Filed: June 17, 1986
    Date of Patent: November 29, 1988
    Assignee: FMC Corporation
    Inventors: Robert Henrie, II, Christine M. Green, Robert E. Sticker
  • Patent number: 4783485
    Abstract: The invention relates to new benzoylurea compounds having insecticidal and acaricidal activity, of the general formula ##STR1## wherein R.sub.1 is a hydrogen atom or represents 1 or 2 halogen atoms;Ar is a para-phenylene group or a para-pyridylene group, which groups may be substituted with 1 or 2 substituents selected from the group consisting of chlorine, methyl and trifluoromethyl;B is an oxygen atom or represents a group having the formula ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: November 8, 1988
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt, Roelof Van Hes
  • Patent number: 4766134
    Abstract: Novel fungicidal pyridyl cyclopropane carboxamides having the general structural formula ##STR1## in which R is selected from the group halogen C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, R.sub.1 is selected from the group of --H and --C.tbd.N; and R.sub.2 is selected from the group of --H, 1-CH.sub.3 and 2-CH.sub.3 ; X is O or S; and fungicidally acceptable organic and inorganic salts thereof. These compounds provide excellent control of fungal growth.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: August 23, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Don R. Baker, Keith H. Brownell
  • Patent number: 4762932
    Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: August 9, 1988
    Assignees: Imperial Chemical Industries, Ltd., ICI Americas, Inc.
    Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
  • Patent number: 4762928
    Abstract: A novel amino-trifluoromethylpyridine compound selected from the group consisting of 3-amino-5-trifluoromethylpyridine, 2-amino-4-trifluoromethylpyridine, and 2-amino-4,6-bis(trifluoromethyl)pyridine, and, a process for preparing the same by reacting a halogeno-trifluoromethylpyridine compound with ammonia at a temperature of 50.degree. to 200.degree. C. The compound is useful as an intermediate from which a compound effective in controlling various harmful organisms or an effective component compound of medicines can be easily derived.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: August 9, 1988
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Yasuhiro Tsujii, Tatsuo Isogai, Takao Awazu, Hisayoshi Jyonishi, Tokiya Kimura
  • Patent number: 4748244
    Abstract: The invention relates to a process for the preparation of pyridine-2,3-dicarboxylic acid derivatives of formula ##STR1## which process comprises reacting a hydrazone of formula II ##STR2## with a maleic acid derivative of formula III ##STR3## to give a 1-amino-1,4-dihydropyridine-2,3-dicarboxylic acid derivative of formula IV ##STR4## and subsequently removing R.sub.9 R.sub.10 NH. In the above formulae, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.9, R.sub.10 and X are as defined in claim 1. The pyridine-2,3-dicarboxylic acid derivatives of formula I are intermediates for the preparation of herbicidal compounds.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: May 31, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Adrian Waldner, Achim Roloff, Daniel Bellus
  • Patent number: 4748165
    Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 31, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4739070
    Abstract: 2- and 4-(Dichloromethyl)pyridines containing electron withdrawing substituents on the ring are prepared by the reaction of the corresponding 2- or 4-halopyridines with excess chloroform in the presence of a strong base in a medium containing a dipolar aprotic solvent or a phase transfer catalyst. 3-Chloro-5-(trifluoromethyl)-2-(dichloromethyl)pyridine, for example, is prepared by the reaction of 2,3-dichloro-5-(trifluoromethyl)pyridine with chloroform in the presence of sodium hydroxide and N-methylpyrrolidone. Substituted 2-(dichloromethyl)pyridines are useful as agricultural pesticides and as intermediates for the preparation of agricultural pesticides.
    Type: Grant
    Filed: April 23, 1986
    Date of Patent: April 19, 1988
    Assignee: The Dow Chemical Company
    Inventor: Jon A. Orvik
  • Patent number: 4725608
    Abstract: New semicarbazide derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen,R.sup.2 is hydrogen, lower alkyl, ar(lower)alkyl, lower alkenyl or aryl,R.sup.3 is lower alkyl, ar(lower)alkyl, lower alkenyl or aryl, orR.sup.2 and R.sup.3 are taken together to form (C.sub.2 -C.sub.6)alkylidene group optionally substituted with aryl or taken together with the adjacent nitrogen atom to form a saturated or unsaturated, 5- or 6-membered heterocyclic group optionally substituted with aryl; orR.sup.1 and R.sup.2 are taken together with the adjacent nitrogen atoms to form a saturated or unsaturated, 5- or 6-membered heterocyclic group or 1,2-diazaspiroalkane-1,2-diyl group,R.sup.3 is hydrogen, lower alkyl, ar(lower)alkyl, lower alkenyl or aryl;R.sup.4 is aryl which may have substituent(s) selected from lower alkyl, halogen, lower alkoxy, lower alkylamino, halo(lower)alkyl, hydroxy, lower alkanoyl, esterified carboxy and carboxy,R.sup.
    Type: Grant
    Filed: November 21, 1984
    Date of Patent: February 16, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Osamu Nakaguchi, Norihiko Shimazaki, Yoshio Kawai, Masashi Hashimoto, Michie Nakatuka
  • Patent number: 4701447
    Abstract: This invention relates to organic acid-substituted guanidine compounds. Also disclosed are methods for preparing the compounds, compositions containing them, and methods for their use as anthelmintics.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: October 20, 1987
    Assignee: Schering Corporation
    Inventors: Dhiru B. Vashi, Jeffrey N. Clark, Neil A. Lindo
  • Patent number: 4681943
    Abstract: 5-Alkyl-1-(2-pyridinyl)-1H-1,2,4-triazol-3-ols are prepared in good yield by reacting an appropriate 1-acyl-1-(2-pyridinyl)-semicarbazide with a base in the presence of a non-nucleophilic solvent. The compounds so prepared are intermediates used in the preparation of insecticides. The starting semicarbazide materials are novel compounds.
    Type: Grant
    Filed: March 17, 1986
    Date of Patent: July 21, 1987
    Assignee: The Dow Chemical Company
    Inventors: Charles E. Whitten, R. Garth Pews
  • Patent number: 4672121
    Abstract: A process for preparing a 4-substituted pyridine product from a starting pyridine substituted in the 4-position by a leaving group susceptible to nucleophilic displacement when the starting pyridine is in quaternized form, comprises,quaternizing the starting pyridine under effective acidic conditions with acrylamide, N-monoalkylacrylamide or N-dialkylacrylamide,subjecting the resultant, corresponding quaternized starting pyridine, to a nucleophilic displacement reaction with a reagent which reacts with it to produce the corresponding quaternary salt of the 4-substituted pyridine product, anddequaternizing the latter under effective basic conditions to liberate the 4-substituted pyridine product.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: June 9, 1987
    Assignee: Nepera Chemical Co.
    Inventor: Laurence J. Nummy
  • Patent number: 4665073
    Abstract: The invention relates to guanidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-15C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 --E--W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O,S or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: May 12, 1987
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman
  • Patent number: 4629731
    Abstract: N-(2,6-Disubstitutedphenyl)-N'-3- and 4-pyridinyl ureas and pharmaceutically acceptable acid addition salts having anticonvulsant activity are described as well as a process for their manufacture, formulations containing the compounds and a method of treating epilepsy using the compounds in unit dosage form.
    Type: Grant
    Filed: April 30, 1985
    Date of Patent: December 16, 1986
    Assignee: Warner-Lambert Company
    Inventors: Sandra J. Lobbestael, Ivan C. Nordin, Robert Fleming
  • Patent number: 4619944
    Abstract: Provided are antihypertensive compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl, and may be the same or different,m is an integer from 0 to 2 inclusive,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl.Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl, heterocyclic, --CO--SR, --CS--SR, ##STR2## CH.sub.2 CO.sub.2 R, --CHM--CO.sub.2 R, --CH.sub.2 --CO--SR, --CN, ##STR3## --CO--NH--CH.sub.2 CO.sub.2 R, ##STR4## or --CO--CO.sub.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: October 28, 1986
    Assignee: USV Pharmaceutical Corporation
    Inventors: Raymond D. Youssefyeh, Howard Jones
  • Patent number: 4604465
    Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: August 5, 1986
    Assignees: ICI Americas, Inc., Imperial Chemical Industries, Limited
    Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
  • Patent number: 4602938
    Abstract: Guanidine derivatives of the formula ##STR1## in which R.sup.2 represents a six-membered aromatic heterocyclic structure which contains at least one nitrogen atom and is substituted by halogen, amino, cyano or formyl and/or by optionally substituted radicals from the series comprising alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl and alkoxycarbonyl, and/or is optionally fused,R.sup.3 represents hydrogen, an optionally substituted radical from the series comprising alkyl, cycloalkyl, alkenyl, alkinyl and aralkyl, or the radical --S(O).sub.n --R.sup.6,the other radicals can have varied meanings, andacid adducts and salts thereof,which possess herbicidal and plant growth regulating activity.
    Type: Grant
    Filed: February 9, 1984
    Date of Patent: July 29, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Koichi Moriya, Theodor Pfister, Hans-Jochem Riebel, Ludwig Eue, Robert R. Schmidt, Klaus Lurssen
  • Patent number: 4594352
    Abstract: There are described compounds of formula: ##STR1## in which one of R and R.sup.1 is F or Cl and the other is H, F or Cl;X is a 1,4-phenylene or pyridyl bound in positions 2 and 5, optionally substituted;Y is a phenyl, 2- or 3-pyridyl, optionally substituted.The compounds of formula I are endowed with a high insecticide activity which is mainly directed against insect larvae and eggs.
    Type: Grant
    Filed: April 19, 1984
    Date of Patent: June 10, 1986
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Franco Bettarini, Gabriele Giovarruscio, Paolo Piccardi, Franca Reggiori, Vincenzo Caprioli, Angelo Longoni
  • Patent number: 4567272
    Abstract: New 2-aminonitropyridine derivatives are disclosed of the formula: ##STR1## wherein the nitro group is in the 3- or 5-position and X represents hydrogen, an alkoxy group with 1 to 3 C atoms or an unsubstituted or alkyl- or hydroxyalkyl substituted amino group, the alkyl portion of which has 1 to 3 C atomsR.sub.1 and R.sub.2 may be the same or different and represent hydrogen, divalent alkyl- with 1 to 3 C atoms, divalent cyclopropyl- or divalent alkenyl with 1 to 3 C atoms, phenylene- or divalent pyrrol andY and Z may be the same or different and represent hydrogen, hydroxyl- or amino group of the formula II: ##STR2## wherein R.sub.3 and R.sub.4 may be the same or different and represent hydrogen, an unsubstituted alkyl or alkyl with 1 to 3 C atoms, substituted at any position by hydroxy or amino with 1 to 3 C atoms, with the proviso that whenever X represents hydrogen, then R.sub.1 and R.sub.2 cannot both be hydrogen, and R.sub.1 is not hydrogen, R.sub.
    Type: Grant
    Filed: September 11, 1984
    Date of Patent: January 28, 1986
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Winfried Orth, Werner Fickert
  • Patent number: 4567188
    Abstract: Compounds of the formula ##STR1## in which R.sup.1 is an optionally substituted aryl or heteroaryl radical,R.sup.2 is an alkyl or alkenyl radical which is optionally substituted by alkoxy or cycloalkyl, or an optionally substituted aryl or heteroaryl radical, and X is an optionally aklyl-substituted methylene radical or a direct bond, but if X is a direct bond R.sup.2 is not aryl,or physiologically acceptable acid addition salts thereof, exhibit activity on the circulation system particularly as hypotensive agents.
    Type: Grant
    Filed: August 10, 1983
    Date of Patent: January 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ekkehard Niemers, Andreas Knorr, Bernward Garthoff
  • Patent number: 4556668
    Abstract: Described herein are compounds of the formula ##STR1## wherein R.sub.1 is alkyl of from 1 to about 5 carbon atoms, alkenyl of from 2 to about 5 carbon atoms, alkynyl of from 3 to about 5 carbon atoms, cycloalkyl of from 3 to about 7 carbon atoms, alkylcarboxymethyl wherein the alkyl portion is from 1 to about 5 carbon atoms, arylcarboxymethyl wherein the aryl portion is from 6 to about 10 carbon atoms, aryl of from 6 to about 10 carbon atoms, or aralkyl wherein the alkyl portion is from 1 to about 5 carbon atoms and the aryl portion is from about 6 to about 10 carbon atoms; R.sub.2 and R.sub.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: December 3, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: Paul W. Erhardt, Chi Woo
  • Patent number: 4514571
    Abstract: A process for the preparation of a urea derivative having the formula: ##STR1## in which A represents a straight- or branched-chain alkyl group having 1-20 carbon atoms, an aryl group, or a heterocyclic group, and each of R.sup.1 and R.sup.2 represents hydrogen, a straight- or branched-chain alkyl group having 1-20 carbon atoms, an alicyclic group, or an aryl groups, which comprises:reacting sodium salt of an N-halogenamide with a quaternary ammonium salt to obtain its addition salt and then,reacting said addition salt with an amine derivative in the absence or presence of an organic solvent.
    Type: Grant
    Filed: May 19, 1983
    Date of Patent: April 30, 1985
    Assignee: UBE Industries, Ltd.
    Inventors: Mamoru Nakai, Fumio Iwata, Teruhiko Inoue
  • Patent number: 4496573
    Abstract: 1-Acyl-3-pyridyl guanidine and 1-acyl-3-pyridylalkyl guanidine compounds, methods for the treatment of blood pressure disorders, including hypertension, in humans and other mammals.
    Type: Grant
    Filed: August 24, 1982
    Date of Patent: January 29, 1985
    Assignee: William H. Rorer, Inc.
    Inventors: William L. Studt, Harry K. Zimmerman
  • Patent number: 4464374
    Abstract: The invention relates to a guanidine derivative of the formula: ##STR1## in which W is a 2-6C alkylene chain optionally substituted by 1 or 2 1-4C alkyls; E is O, S, SO, SO.sub.2 or NR.sup.3 in which R.sup.3 is H or 1-6C alkyl; R.sup.1 is H or a straight chain 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls; or R.sup.1 and R.sup.3 are joined to form a morpholine, pyrrolidine, piperidine or piperazine ring; X, P, Y, Q and R.sup.2 are as defined in the specification, and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing process, pharmaceutical compositions and intermediates are also described. The compounds of the formula I are histamine H-2 antagonists.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: August 7, 1984
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman, Derrick F. Jones, Keith Oldham
  • Patent number: 4447441
    Abstract: The invention relates to guanidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I:- ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 --E--W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O,S or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.
    Type: Grant
    Filed: March 1, 1982
    Date of Patent: May 8, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman
  • Patent number: 4436911
    Abstract: This invention relates to a novel class of heterocyclic amidinourea and heterocylic amidinothiourea compounds wherein the heterocyclic substitution is at the 1-N urea nitrogen atom. These compounds exhibit pharmaceutical activity and may be incorporated into pharmaceutical preparations for producing anti-ulcerogenic, antisecretory, antispasmodic, antimotility, cardiovascular, antidiarrheal or antiparasitic action.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: March 13, 1984
    Assignee: William H. Rorer, Inc.
    Inventors: William L. Studt, Harry K. Zimmerman, George H. Douglas
  • Patent number: 4426387
    Abstract: The invention concerns compounds of formula ##STR1## and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula ##STR2## in which Q is O,S,--CR.sup.7 .dbd.CR.sup.8 --, --N.dbd.CR.sup.8 -- and --N.dbd.N--; R.sup.4, R.sup.5 and R.sup.6, and R.sup.7 and R.sup.8 when present, each represent hydrogen or defined substituents and additionally either R.sup.4 and R.sup.5 when adjacent or R.sup.6 and R.sup.8 when adjacent, together with the carbon atoms to which they are attached also represent a fused five or six membered carbocyclic or heterocyclic ring optionally carrying one or more defined substituents; R is an optionally substituted aryl or heteroaryl radical or a cycloalkyl radical containing 5 to 7 carbon atoms; R.sup.1, R.sup.2, R.sup.3 and R.sup.9 are each hydrogen or a lower alkyl group; n is 0 or 1; X is .dbd.O, .dbd.S or .dbd.NH; Y is --O-- or a direct bond and Z is --CO-- or --CH.sub.
    Type: Grant
    Filed: April 7, 1982
    Date of Patent: January 17, 1984
    Assignee: John Wyeth & Brother Ltd.
    Inventors: John L. Archibald, Terrence J. Ward
  • Patent number: RE31550
    Abstract: N-(2-Chloro-4-pyridyl)ureas represented by the formula (I): ##STR1## wherein R.sub.1 represents hydrogen or alkyl, R.sub.2 represents an aromatic group, especially phenyl, which may be substituted by alkyl, alkoxyl, hydroxyl or halogen, and X is oxygen or sulfur, and acid addition salts thereof, useful as plant growth regulators, are disclosed. Method of making and using same and agricultural compositions thereof are also disclosed.
    Type: Grant
    Filed: September 25, 1981
    Date of Patent: April 10, 1984
    Assignees: Koichi Shudo, Toshihiko Okamoto, Yo Isogai, Soshiro Takahashi
    Inventors: Koichi Shudo, Toshihiko Okamoto, Yo Isogai, Soshiro Takahashi