Thiomorpholines (i.e., Fully Hydrogenated 1,4-thiazines) Patents (Class 544/59)
  • Patent number: 4224244
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: September 23, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4223138
    Abstract: A process for the preparation of an aminoethanol is described wherein an amine is vaporized in a collection vessel and the vapors are caused to pass upwardly through a defined reaction zone into a condensation zone where they are condensed and caused to flow downwardly into the reaction zone. In the reaction zone the flow toward the collection zone is retarded and, while retarded, epoxide reactant is directed thereagainst. The aminoethanol so formed is removed into the collection zone such as by directing condensed amine thereagainst.
    Type: Grant
    Filed: March 29, 1978
    Date of Patent: September 16, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rudiger Schubart
  • Patent number: 4220650
    Abstract: A series of organic diamine base compounds derived from either an aromatic, alicyclic or heterocyclic ring and possessing, for the most part, an intervening methylene group between the ring and the aforesaid basic moiety have been prepared, including their pharmaceutically acceptable acid addition salts as well as oral pharmaceutical compositions containing same. These particular compounds are found to be useful in therapy as oral hypoglycemic agents. Preferred member compounds include 1,1'-[1,2-phenylenebis(methylene)]bispiperidine, 2,3-dihydro-2-[2-(1-piperidinomethyl)phenylmethyl]-1H-isoindole and 2,3-dihydro-2-[2-(4-morpholinomethyl)phenylmethyl]-1H-isoindole. Alternate methods of preparation are provided and the two principal synthetic routes leading to these compounds are described in some detail.
    Type: Grant
    Filed: October 18, 1978
    Date of Patent: September 2, 1980
    Assignee: Pfizer Inc.
    Inventor: John L. Belletire
  • Patent number: 4216326
    Abstract: N-{3- and 4-[R.sub.1 -(phenyl)-C(.dbd.X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 3- or 4-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3- or 4-lithiophenyl-lower-alkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)-lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.
    Type: Grant
    Filed: May 3, 1978
    Date of Patent: August 5, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4208423
    Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are the same or different and are C.sub.1 to C.sub.6 alkyl; C.sub.5 or C.sub.6 cycloalkyl; C.sub.5 or C.sub.6 cycloalkenyl; phenyl optionally substituted with a substitutent selected from the group C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkoxy and halo; or C.sub.4 or C.sub.5 heterocyclic aryl, the heteroatom selected from the group oxygen, nitrogen and sulfur; Y is the radical selected from (CH.sub.2).sub.n, (C.sub.4 H.sub.8 S), (C.sub.4 H.sub.8 O) and ##STR2## where R is hydrogen or C.sub.1 to C.sub.6 alkyl and n is the integer 4 or 5; and X is selected from the group methanesulfonate, benzenesulfonate, p-toluenesulfonate, nitrate, chloride, bromide and iodide. Methods for preparing these compounds are also disclosed. The compounds of the present invention are useful as anticholinergic agents.
    Type: Grant
    Filed: November 24, 1978
    Date of Patent: June 17, 1980
    Assignee: Syntex Inc.
    Inventor: Jurg R. Pfister
  • Patent number: 4192873
    Abstract: The invention relates to novel ortho-aminoacetophenones of the formula I ##STR1## and their tautomers, in which Z is hydrogen, halogen, lower alkyl, cycloalkyl, lower alkoxy, trifluoromethyl, nitro or substituted or unsubstituted sulphamoyl, m is 1 or 2, R is hydrogen, aryl or lower alkyl, R.sub.1 is hydrogen or lower alkyl, R.sub.2 is lower alkyl, cycloalkyl, aryl, cycloalkyl-lower alkyl, aryl-lower alkyl or substituted or unsubstituted pyridyl, R.sub.
    Type: Grant
    Filed: October 28, 1977
    Date of Patent: March 11, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Pier G. Ferrini, Richard Goschke, Alfred Sallmann, Alberto Rossi
  • Patent number: 4172945
    Abstract: Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: October 30, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Joseph E. Sundeen, Joyce Reid
  • Patent number: 4156723
    Abstract: Compounds are provided having the structure ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen or acyl, and R.sub.5 is hydrogen or acyl, X is a straight or branched bivalent alkylene radical and Y is ##STR2## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: August 4, 1977
    Date of Patent: May 29, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Michael E. Condon, Joyce Reid
  • Patent number: 4146711
    Abstract: This invention relates to N-alkyl sulfone containing quaternary ammonium derivatives of 1,4-thiazines; to the preparation thereof; and to the uses thereof, for example as corrosion inhibitors, microbiocides, etc.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: March 27, 1979
    Assignee: Petrolite Corporation
    Inventor: Patrick M. Quinlan
  • Patent number: 4146709
    Abstract: This invention relates to N-alkyl thioethers of quaternary ammonium derivatives of 1,4-thiazines; to the preparation thereof; and to the uses thereof for example as corrosion inhibitors, microbiocides, etc.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: March 27, 1979
    Assignee: Petrolite Corporation
    Inventor: Patrick M. Quinlan
  • Patent number: 4139626
    Abstract: Benzene ring substituted benzimidazole-2-carbamate derivatives represented by the formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; ##STR2## is a 5, 6, 7 or 8 membered heterocyclic ring containing 1 to 2 hetero atoms; the ##STR3## substitution being at the 5(6)-position; and the pharmaceutically acceptable salts thereof.The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: February 13, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Colin Beard
  • Patent number: 4129598
    Abstract: Trifluoromethylthiophenylethylamine derivatives, made from the corresponding acid chlorides by successive reduction, condensation with nitroethane, reduction, and condensation with an amine, possess anorexigenic properties, unaccompanied by central stimulant activity or cardiovascular effects.
    Type: Grant
    Filed: May 24, 1974
    Date of Patent: December 12, 1978
    Assignee: Synthelabo
    Inventors: Don P. R. L. Giudicelli, Henry Najer
  • Patent number: 4115416
    Abstract: .alpha.-Phenoxyacetic acids, in which the .alpha.-position is substituted by an alkyl residue with 5 to 12 carbon atoms and the phenyl residue is substituted by a cycloaliphatic hydrocarbon residue which is unsaturated in the 1-position and is only singly unsaturated, and their esters and amides are useful as hypolipidaemic agents.
    Type: Grant
    Filed: September 9, 1976
    Date of Patent: September 19, 1978
    Assignee: Ciba-Geigy AG
    Inventors: Alberto Rossi, Christian Egli
  • Patent number: 4113709
    Abstract: This invention relates to polymers of quaternary thiazines having the recurrent structure ##STR1## WHERE Z is S, SO, SO.sub.2, x is 2 or more, R.sub.1 is a hydrocarbon or substituted hydrocarbon, R.sub.2 is alkylene, alkenylene, aralkylene, alkylene ether, X is an anion, n is a number from 3-500. These polymers are useful as flocculants and/or water clarifiers, corrosion inhibitors, antistatic agents, demulsifiers, microbiocides, algicides and the like.
    Type: Grant
    Filed: August 12, 1976
    Date of Patent: September 12, 1978
    Assignee: Petrolite Corporation
    Inventor: Patrick M. Quinlan
  • Patent number: 4111937
    Abstract: 3-Amino-2,4,6-triiodobenzoic acids optionally substituted in the 5-position by amino or carboxy or a derivative thereof react with dibasic acid anhydrides to give the corresponding cyclic imides (A), which can be hydrolyzed to the corresponding anilic acids (B). The latter can be further alkylated on the anilide nitrogen atom. Compounds A and B are useful as cholecystographic and urographic agents.
    Type: Grant
    Filed: October 18, 1976
    Date of Patent: September 5, 1978
    Assignee: Sterling Drug Inc.
    Inventor: James H. Ackerman
  • Patent number: 4107434
    Abstract: Novel process for the production of antibacterially active pleuromutilin derivatives.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: August 15, 1978
    Assignee: Sandoz Ltd.
    Inventor: Erwin Waldvogel
  • Patent number: 4104383
    Abstract: Compounds having psychostimulant, antispasmodic, hypotensive and analgesic properties are disclosed. The compounds have the formula: ##STR1## in which R.sup.2 is selected from the group consisting of a hydrogen atom and a halogen atom;R.sup.1 is selected from the group consisting of a cyclohexyl group and a phenyl group, and is a cyclohexyl group when R.sup.2 is a halogen atom;A is selected from the group consisting of CH.sub.2 CH.sub.2 and CH.dbd.CH groups; andNr.sup.3 r.sup.4 is selected from the group consisting of an alkylamino group, a dialkylamino group and a heterocyclic ring containing from 5 to 7 atoms in the ring, said ring optionally having one or more sbustituents and optionally containing a second hetero-atom; and acid addition salts of said compounds.
    Type: Grant
    Filed: June 4, 1976
    Date of Patent: August 1, 1978
    Assignee: C M Industries
    Inventor: Francois Krausz
  • Patent number: 4101659
    Abstract: Benzhydryl derivatives of guanidine (Formula I) having blood sugar lowering activity; pharmaceutical hypoglycemic compositions thereof and methods of administering same to hyperglycemic individuals.
    Type: Grant
    Filed: August 29, 1977
    Date of Patent: July 18, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris Royce Rasmussen
  • Patent number: 4098791
    Abstract: An improved multistep process for the production of intermediates for hypotensive compounds, which intermediates are of the formula V: ##STR1## wherein R.sub.1 and R.sub.2 are lower alkyl of 1 to 4 carbon atoms, inclusive, alkenyl of 3 or 4 carbon atoms, cycloalkyl from 3 to 7 carbon atoms, phenylalkyl in which the alkyl group is defined as above, or the group ##STR2## is a heterocyclic moiety of 4 to 8 ring members, e.g., azetidinyl, piperidino, pyrrolidinyl, hexahydroazepinyl, or heptamethyleneimino, each of which can be substituted by one or two methyl groups, N-alkylpiperazino, wherein alkyl is defined as above, morpholino, or thiomorpholino, and wherein R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive, starts with the corresponding secondary amine I ##STR3## wherein R.sub.1 and R.sub.2 have the significance of above.
    Type: Grant
    Filed: July 29, 1977
    Date of Patent: July 4, 1978
    Assignee: The Upjohn Company
    Inventors: Thomas A. Hylton, Muniraj D. Pillai
  • Patent number: 4082773
    Abstract: Compounds are provided of the structure ##STR1## WHEREIN X--Z--Y together with two carbons of the cycloalkyl ring form a 5- or 6-membered ring, wherein R.sup.1 is hydrogen, aralkyl or acyl, n is 0, 1 or 2, and n' is 0, 1, 2 or 3, R.sup.2 is hydrogen, lower alkyl or aralkyl, R.sup.3 is hydrogen, acyl, lower alkyl, aralkyl, lower alkoxy, carboxy, halo, alkenyl, nitro, cycloalkyl, amino, acylamino, R.sup.2 O(CH.sub.2).sub.n 2 where n.sup.2 is 0, 1 or 2 or dihydroxyalkyl, X and Y may be the same or different and can be --CH.sub.2 --, .dbd.N--, --O--, --S--, --NR.sup.4 --, --O--CH.sub.2 --, --S--CH.sub.2 --, or --NR.sup.4 --CH.sub.2 -- where R.sup.4 is hydrogen, lower alkyl or aryl, Z can be ##STR2## where R.sup.5 and R.sup.6 can be hydrogen, lower alkyl, cycloalkyl, aryl, haloalkyl, amino or substituted or unsubstituted aminoalkyl; ##STR3## and --X--Z--Y-- can be taken together to form ##STR4## and ##STR5## These compounds are useful as anti-fibrillatory agents, disinfectants and water-softeners.
    Type: Grant
    Filed: July 3, 1972
    Date of Patent: April 4, 1978
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Frederic Peter Hauck
  • Patent number: 4072675
    Abstract: N-Phenyl amidines which have diuretic, antithrombogenic, smooth muscle relaxant, anti-inflammatory and antiarrhythmic properties have been discovered. They are prepared by reacting a substituted aniline with a carboxamide selected from the group consisting of amides and lactams in the presence of phosphorus oxychloride. Typical examples of substituted N-phenyl amidines thus obtained are 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-(N-phenylbenzylamino)-1-pyrroline, 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole and 4,5,6,7,8,9-hexahydro-2-(N-phenylphenethylamino)-3H-azonine. Indole substituted N-phenyl amidines can be rearranged to provide iminopyrrolidinylindoles which are useful as diuretic, antithrombogenic and smooth muscle relaxant agents. In the case of 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole, the rearranged product is 3-[[2-(p-methoxyphenylimino)-1-pyrrolidinyl]methyl]indole.
    Type: Grant
    Filed: October 24, 1975
    Date of Patent: February 7, 1978
    Assignee: Mead Johnson & Company
    Inventors: Yao Hua Wu, Walter G. Lobeck, Jr.
  • Patent number: 4070387
    Abstract: Tetrafluoro derivatives of 10,11-dihydrodibenzo[a,d]cyclohepten-5-aminomethyl compounds and the corresponding N-substituted derivatives thereof, useful as antiarrhythmic agents, are prepared from tetrafluoro derivatives of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one by reduction to the corresponding 5-ol compound and subsequently converting said 5-ol compound to the corresponding 5-halo and the 5-aminomethyl derivatives by reactions known in the prior art.
    Type: Grant
    Filed: October 4, 1976
    Date of Patent: January 24, 1978
    Assignee: Merck & Co., Inc.
    Inventor: Marcia Elizabeth Christy
  • Patent number: 4064239
    Abstract: Novel substituted benzenedisulfonamides are disclosed which compounds are active anthelmintic agents being particularly useful against fascioliasis in sheep and cattle. Specifically the active compounds are 4-amino-1,3-benzenedisulfonamide with an unsaturated substituted alkyl group. Compositions and methods containing the novel substituted benzenedisulfonamides for use in anthelmintic therapy particularly against liver fluke are also disclosed.
    Type: Grant
    Filed: September 26, 1975
    Date of Patent: December 20, 1977
    Assignee: Merck & Co., Inc.
    Inventor: Helmut H. Mrozik
  • Patent number: 4058532
    Abstract: The invention relates to novel 1-(4-R.sub.1 O-phenyl)-2-(4-R.sub.2 -phenyl)-6-R.sub.3 -1,2,3,4-tetrahydroquinolines having antifertility and hypocholesterolemic activities, to their preparation, and to novel intermediates therefor.
    Type: Grant
    Filed: May 13, 1976
    Date of Patent: November 15, 1977
    Assignee: Sterling Drug Inc.
    Inventor: Malcolm R. Bell
  • Patent number: 4054652
    Abstract: Dihydro- and tetrahydro-iminothiazines are inhibitors of indoleamine-N-methyl transferase in vivo.
    Type: Grant
    Filed: June 15, 1976
    Date of Patent: October 18, 1977
    Assignee: Merck & Co., Inc.
    Inventors: Clarence S. Rooney, Joshua Rokach, Edward J. Cragoe, Jr.
  • Patent number: 4053596
    Abstract: Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: January 14, 1976
    Date of Patent: October 11, 1977
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic Peter Hauck, Joyce Reid, Venkatachala L. Narayanan, Christopher M. Cimarusti, Rudiger D. Haugwitz, Joseph E. Sundeen
  • Patent number: 4047923
    Abstract: Plant-growth regulating compositions and methods having strong effects on plant growth, containing a heterocyclic sulfonium salt of the formula ##STR1## in which R is alkyl; substituted alkyl; alkenyl; alkynyl; cycloalkyl; or aralkyl which is optionally substituted in the aryl moiety;A.sup.- is one equivalent of an anion; and X is oxygen or the group N.sup.+ R'R" A.sup.- or S.sup.+ -R'" A.sup.- in whichA.sup.- is identified as above;R' and R", which may be identical or different, are each alkyl of up to 6 carbon atoms; andR'" is defined as R or can be, together with R, an ethylene linkage.
    Type: Grant
    Filed: June 18, 1975
    Date of Patent: September 13, 1977
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Naumann, Klaus Lurssen, Klaus Sasse
  • Patent number: 4042584
    Abstract: This application discloses arylethynylphenylcyclopropylamines and processes for their preparation. These amines exhibit monoamine oxidase (MAO) inhibiting activity.
    Type: Grant
    Filed: April 8, 1975
    Date of Patent: August 16, 1977
    Assignee: Merck & Co., Inc.
    Inventor: David C. Remy