Thiomorpholines (i.e., Fully Hydrogenated 1,4-thiazines) Patents (Class 544/59)
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Patent number: 4224244Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: May 9, 1979Date of Patent: September 23, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: 4223138Abstract: 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: GrantFiled: March 29, 1978Date of Patent: September 16, 1980Assignee: Bayer AktiengesellschaftInventor: Rudiger Schubart
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Patent number: 4220650Abstract: 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: GrantFiled: October 18, 1978Date of Patent: September 2, 1980Assignee: Pfizer Inc.Inventor: John L. Belletire
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Patent number: 4216326Abstract: 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: GrantFiled: May 3, 1978Date of Patent: August 5, 1980Assignee: Sterling Drug Inc.Inventor: Bernard L. Zenitz
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Patent number: 4208423Abstract: 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: GrantFiled: November 24, 1978Date of Patent: June 17, 1980Assignee: Syntex Inc.Inventor: Jurg R. Pfister
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Patent number: 4192873Abstract: 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: GrantFiled: October 28, 1977Date of Patent: March 11, 1980Assignee: Ciba-Geigy CorporationInventors: Pier G. Ferrini, Richard Goschke, Alfred Sallmann, Alberto Rossi
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Patent number: 4172945Abstract: 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: GrantFiled: July 27, 1978Date of Patent: October 30, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic P. Hauck, Joseph E. Sundeen, Joyce Reid
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Patent number: 4156723Abstract: 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: GrantFiled: August 4, 1977Date of Patent: May 29, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic P. Hauck, Michael E. Condon, Joyce Reid
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Patent number: 4146711Abstract: 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: GrantFiled: March 13, 1978Date of Patent: March 27, 1979Assignee: Petrolite CorporationInventor: Patrick M. Quinlan
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Patent number: 4146709Abstract: 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: GrantFiled: March 13, 1978Date of Patent: March 27, 1979Assignee: Petrolite CorporationInventor: Patrick M. Quinlan
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Patent number: 4139626Abstract: 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: GrantFiled: January 10, 1977Date of Patent: February 13, 1979Assignee: Syntex (U.S.A.) Inc.Inventor: Colin Beard
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Patent number: 4129598Abstract: 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: GrantFiled: May 24, 1974Date of Patent: December 12, 1978Assignee: SynthelaboInventors: Don P. R. L. Giudicelli, Henry Najer
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Patent number: 4115416Abstract: .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: GrantFiled: September 9, 1976Date of Patent: September 19, 1978Assignee: Ciba-Geigy AGInventors: Alberto Rossi, Christian Egli
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Patent number: 4113709Abstract: 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: GrantFiled: August 12, 1976Date of Patent: September 12, 1978Assignee: Petrolite CorporationInventor: Patrick M. Quinlan
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Patent number: 4111937Abstract: 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: GrantFiled: October 18, 1976Date of Patent: September 5, 1978Assignee: Sterling Drug Inc.Inventor: James H. Ackerman
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Patent number: 4107434Abstract: Novel process for the production of antibacterially active pleuromutilin derivatives.Type: GrantFiled: January 10, 1977Date of Patent: August 15, 1978Assignee: Sandoz Ltd.Inventor: Erwin Waldvogel
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Patent number: 4104383Abstract: 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: GrantFiled: June 4, 1976Date of Patent: August 1, 1978Assignee: C M IndustriesInventor: Francois Krausz
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Patent number: 4101659Abstract: Benzhydryl derivatives of guanidine (Formula I) having blood sugar lowering activity; pharmaceutical hypoglycemic compositions thereof and methods of administering same to hyperglycemic individuals.Type: GrantFiled: August 29, 1977Date of Patent: July 18, 1978Assignee: McNeil Laboratories, IncorporatedInventor: Chris Royce Rasmussen
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Patent number: 4098791Abstract: 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: GrantFiled: July 29, 1977Date of Patent: July 4, 1978Assignee: The Upjohn CompanyInventors: Thomas A. Hylton, Muniraj D. Pillai
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Patent number: 4082773Abstract: 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: GrantFiled: July 3, 1972Date of Patent: April 4, 1978Assignee: E. R. Squibb & Sons, Inc.Inventor: Frederic Peter Hauck
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Patent number: 4072675Abstract: 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: GrantFiled: October 24, 1975Date of Patent: February 7, 1978Assignee: Mead Johnson & CompanyInventors: Yao Hua Wu, Walter G. Lobeck, Jr.
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Patent number: 4070387Abstract: 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: GrantFiled: October 4, 1976Date of Patent: January 24, 1978Assignee: Merck & Co., Inc.Inventor: Marcia Elizabeth Christy
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Patent number: 4064239Abstract: 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: GrantFiled: September 26, 1975Date of Patent: December 20, 1977Assignee: Merck & Co., Inc.Inventor: Helmut H. Mrozik
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Patent number: 4058532Abstract: 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: GrantFiled: May 13, 1976Date of Patent: November 15, 1977Assignee: Sterling Drug Inc.Inventor: Malcolm R. Bell
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Patent number: 4054652Abstract: Dihydro- and tetrahydro-iminothiazines are inhibitors of indoleamine-N-methyl transferase in vivo.Type: GrantFiled: June 15, 1976Date of Patent: October 18, 1977Assignee: Merck & Co., Inc.Inventors: Clarence S. Rooney, Joshua Rokach, Edward J. Cragoe, Jr.
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Patent number: 4053596Abstract: 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: GrantFiled: January 14, 1976Date of Patent: October 11, 1977Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic Peter Hauck, Joyce Reid, Venkatachala L. Narayanan, Christopher M. Cimarusti, Rudiger D. Haugwitz, Joseph E. Sundeen
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Patent number: 4047923Abstract: 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: GrantFiled: June 18, 1975Date of Patent: September 13, 1977Assignee: Bayer AktiengesellschaftInventors: Klaus Naumann, Klaus Lurssen, Klaus Sasse
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Patent number: 4042584Abstract: This application discloses arylethynylphenylcyclopropylamines and processes for their preparation. These amines exhibit monoamine oxidase (MAO) inhibiting activity.Type: GrantFiled: April 8, 1975Date of Patent: August 16, 1977Assignee: Merck & Co., Inc.Inventor: David C. Remy