Chalcogen Bonded Directly At The 2-position Of The Oxazole Ring Patents (Class 548/221)
  • Patent number: 4287348
    Abstract: Sulphoalkyl quaternary salts of the formula ##STR1## wherein X is --O--, --Se--, --S--, --NR-- or --CR(R)--, R is hydrogen or alkyl, R.sub.1 is hydrogen, methyl or ethyl, R.sub.2 and R.sub.3 are each hydrogen or substituents or together represent the atoms necessary to complete an optionally substituted benzene ring, R.sub.4 is optionally substituted alkylene of 3 or 4 carbon atoms and n is 1 or 0, except that when n is 1, R.sub.1 cannot be hydrogen, are prepared by heating at a temperature above 80.degree. C. a heterocyclic base of the formula ##STR2## wherein X, R.sub.1, R.sub.2, R.sub.3 and n have the indicated meanings with a hydroxysulphonic acid of the formula HOR.sub.4 SO.sub.3 H.
    Type: Grant
    Filed: June 5, 1978
    Date of Patent: September 1, 1981
    Assignee: Ciba-Geigy AG
    Inventors: Rainer Kitzing, Geoffrey E. Ficken, Victor W. Dolden
  • Patent number: 4286096
    Abstract: Azole and azoline disulfides useful as corrosion inhibitors and antiwear agents are prepared by the halogen-induced coupling of a thiol reactant e.g., hydrocarbyl mercaptans, with a metal azole thiolate, e.g. the potassium salt of 3,5-bis-mercapto 1,2,4-thiadiazole or 2,5-bis-mercapto 1,3,4-thiadiazole in a 2-phase reaction medium comprising a mixture of a hydrocarbon and water.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: August 25, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Stanley J. Brois, Antonio Gutierrez
  • Patent number: 4275193
    Abstract: Fortimicin B-4,5-carbamates represented by the formula: ##STR1## wherein R is hydrogen or an amine-protecting group; R.sub.1 is hydrogen or an amine-protecting group; R.sub.2 is hydrogen or loweralkoxycarbonyl; and R.sub.4 is hydrogen or loweralkoxycarbonyl. The compounds are useful as intermediates in the preparation the 2-epi-fortimicins.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: June 23, 1981
    Assignee: Abbott Laboratories
    Inventors: John S. Tananier, Jerry R. Martin
  • Patent number: 4271158
    Abstract: Racemic and optically active compounds of the formulaQ--C.sub.n H.sub.2n --NH--RwhereinQ is ##STR1## where R.sub.1 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl or amino,R.sub.2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atomsor trifluoromethyl,R.sub.1 and R.sub.2, together with each other, are methylenedioxy or ethylenedioxy, andA is --O--, --CH.sub.2 --CH.sub.2 --, or --NR.sub.3 -- where R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms,n is an integer from 2 to 6, inclusive, andR is hydrogen, benzyl or ##STR2## where R.sub.4 is hydrogen, methyl or ethyl,R.sub.5, R.sub.6 and R.sub.7, which may be identical to or different from each other, are each hydrogen, halogen, hydroxymethyl, trifluoromethyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, cyano, --CONHR.sub.3, --CONHOH, --COOR.sub.3, R.sub.8 O--, methylsulfonylmethyl or, when one or two of R.sub.5 through R.sub.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: June 2, 1981
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Anton Mentrup, Kurt Schromm, Ernst-Otto Renth, Richard Reichl
  • Patent number: 4269970
    Abstract: A 1,2-carbamate of fortimicin B and derivatives represented by the formula: ##STR1## wherein: R is hydrogen or monocyclicaryloxycarbonyl, R.sub.1 is hydrogen or monocyclicaryloxycarbonyl; and R.sub.2 is selected from the group consisting of loweralkyl, loweralkoxycarbonyl aminoloweralkyl, hydroxyloweralkyl, hydroxy-substituted aminolowerakyl, an amino acid residue, and N-protected amino acid residue, or when R and R.sub.1 are hydrogen, R.sub.2 can also be hydrogen; and the acid addition salts thereof when R,R.sub.1 or R.sub.2 are hydrogen or an unprotected aminoacid residue.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: May 26, 1981
    Assignee: Abbott Laboratories
    Inventors: John S. Tadanier, Jerry R. Martin
  • Patent number: 4263429
    Abstract: A fortimicin intermediate selected from the group consisting of 1,2',6'-tri-N-benzyloxycarbonylfortimicin B-4,5-carbamate and 1,2',6'-tri-N-acetylfortimicin A-4,5-carbamate. The compounds are useful as intermediates in the preparation of 2-epi-fortimicin B.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: April 21, 1981
    Assignee: Abbott Laboratories
    Inventors: John S. Tadanier, Jerry R. Martin
  • Patent number: 4263440
    Abstract: Heterocyclic phenyl ethers of the formula ##STR1## in which (R).sub.n is hydrogen or up to three identical or different substituents selected from halogen, CF.sub.3, NO.sub.2, CN, alkyl, alkoxy and alkylthio, and A is oxygen, sulfur or N(C.sub.1 -C.sub.4)alkyl, provided that the --OH group is not in para-position if (R).sub.n is hydrogen and A is sulfur, are useful as starting materials for the manufacture of selective herbicides.
    Type: Grant
    Filed: August 28, 1978
    Date of Patent: April 21, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Reinhard Handte
  • Patent number: 4247689
    Abstract: The present invention relates to a new organic heterocyclic isocyanate which is the reaction product of an organic diisocyanate and an amino or hydroxy nitrile. The invention also relates to a process of producing such isocyanates by reacting an excess of the diisocyanate with the nitrile under conditions under which the nitrile will not decompose and then maintaining the reaction mixture at an elevated temperature until the isocyanate nitrile adduct cyclizes. The reaction may be carried out in the presence of a catalyst for isocyanate addition reactions. Additionally, the invention relates to a process for the production of polyurethane by the reaction of the heterocyclic isocyanates with compounds carrying at least two isocyanate reactive hydrogen atoms per molecule.
    Type: Grant
    Filed: June 11, 1979
    Date of Patent: January 27, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Kuno Wagner, Walter Uerdingen
  • Patent number: 4227915
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein X, Y and W represent independently oxygen or sulfur;T represents lower alkyl, lower alkoxy, halo, CF.sub.3 or NO.sub.2 ;m is an integer of from 0 to 2;n is an integer of from 1 to 3; andR is selected from the group consisting of ##STR2## morpholino, pyrrolidyl, pyrrolidyl substituted by from 1 to 2 lower alkyl or lower alkoxy moieties and ##STR3## where a is an integer of from 5 to 8 inclusive; R.sub.1 represents lower alkyl, lower alkenyl, benzyl, phenyl or phenyl substituted by from 1 to 3 lower alkyl, lower alkoxy, lower alkenyl, CF.sub.3 or NO.sub.2 moieties;R.sub.2 represents hydrogen, lower alkyl or lower alkenyl moieties, with the proviso that when X is oxygen, R.sub.1 and R.sub.2 cannot equal methyl. The invention also relates to the use of said compounds in a method of regulating leguminous plant growth as well as to plant growth regulant compositions.
    Type: Grant
    Filed: May 18, 1978
    Date of Patent: October 14, 1980
    Assignee: Monsanto Company
    Inventor: John J. D'Amico
  • Patent number: 4228292
    Abstract: N-substituted benzothiazolines and benzoxazolines having the formula ##STR1## have been found to be effective as herbicides and plant growth regulants.
    Type: Grant
    Filed: July 20, 1978
    Date of Patent: October 14, 1980
    Assignee: Monsanto Company
    Inventor: John J. D'Amico
  • Patent number: 4215119
    Abstract: Racemic and optically active compounds of the formulaQ-C.sub.n H.sub.2n -NH-Rwherein Q is ##STR1## where R.sub.1 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl or amino,R.sub.2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or trifluoromethyl,R.sub.1 and R.sub.2, together with each other, are methylenedioxy or ethylenedioxy, andA is --O--, --CH.sub.2 --CH.sub.2 --, or --NR.sub.3 -- where R.sub.3 is hydrogen or alkyl or 1 to 4 carbon atoms,n is an integer from 2 to 6, inclusive, andR is hydrogen, benzyl or ##STR2## where R.sub.4 is hydrogen, methyl or ethyl,R.sub.5, R.sub.6 and R.sub.7, which may be identical to or different from each other, are each hydrogen, halogen, hydroxymethyl, trifluoromethyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, cyano, --CONHR.sub.3, --CONHOH, --COOR.sub.3, R.sub.8 O--, methylsulfonylmethyl or, when one or two of R.sub.5 through R.sub.
    Type: Grant
    Filed: April 3, 1979
    Date of Patent: July 29, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Anton Mentrup, Kurt Schromm, Ernst-Otto Renth, Richard Reichl, Werner Traunecker, Wolfgang Hoefke
  • Patent number: 4191703
    Abstract: An improved and novel process has been found for the esterification of amino-benzoxazolone compounds containing a .beta.-hydroxyethylsulfonyl group, by means of sulfuric acid or sulfur trioxide, with simultaneous or subsequent hydrolytic cleavage of the oxazolone ring, wherein the esterification and optional hydrolytic ring cleavage are performed in a machine which is operating with a kneading action and effect, using per mol of .beta.-hydroxyethylsulfonyl compound 1 to 20 times the equivalent molar amount of concentrated sulfuric acid, oleum or sulfur trioxide. This novel process has the great advantage that great amounts of sulfuric acid are saved which would contaminate the waste-water, also in form of sodium sulfate formed after the required neutralization. Furthermore, the .beta.-sulfatoethylsulfonyl compounds formed as end-products in the esterification process are obtained in higher yields, in a higher esterification rate and in a higher purity.
    Type: Grant
    Filed: June 8, 1978
    Date of Patent: March 4, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans H. Steuernagel, Ernst Hoyer
  • Patent number: 4174958
    Abstract: New herbicidally active compounds have the formula ##STR1## wherein R.sup.1 is H, alkyl, alkenyl, cycloalkyl, R.sup.2 is CF.sub.3, NO.sub.2, CN, halogen, alkyl, alkoxy or alkyl, and --X--Y--Z-- is ##STR2## in which R.sup.3 is H, or alkyl, R.sup.4 is H, alkyl or cycloalkyl, R.sup.5 is H or alkyl or when --Y--Z-- contains two vicinal R.sup.4 groups then these R.sup.4 groups taken together with the ring carbon atoms to which they are attached form a saturated or unsaturated hydrocarbyl ring containing 5 or 6 carbon atoms.
    Type: Grant
    Filed: September 15, 1978
    Date of Patent: November 20, 1979
    Assignee: Shell Oil Company
    Inventor: Kurt H. G. Pilgram
  • Patent number: 4173646
    Abstract: Tricyclicdicarboximides representatively prepared by the Diels-Alder condensation of a cyclic diene such as cycloheptatriene, cyclooctatetraene and the like with a dienophile such as substituted N-phenylmaleimide and the like are disclosed having pharmaceutical utility as minor tranquilizers and anti-convulsants. Also disclosed are processes for the preparation of such tricyclicdicarboximides; pharmaceutical compositions comprising such compounds and their salt; ester and amide or derivatives; and methods of treatment comprising administering such compounds and compositions.
    Type: Grant
    Filed: September 28, 1978
    Date of Patent: November 6, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Kenneth L. Shepard, William J. Paleveda, Jr.