Cyano Attached Indirectly To The Piperidine Ring By Nonionic Bonding Patents (Class 546/230)
-
Patent number: 4593039Abstract: 1-Aryloxy-3-(substituted aminoalkylamino)-2-propanols and pharmaceutically acceptable salts thereof have .beta.-adrenergic blocking activity with some cardioselectivity and hence are useful as antihypertensive, antianginal, antiarrhythmic and cardioprotective agents and in the treatment of elevated intraocular pressure such as glaucoma.Type: GrantFiled: April 2, 1984Date of Patent: June 3, 1986Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Sandor L. Varga, Gerald S. Ponticello
-
Patent number: 4585796Abstract: The tertiary amines of the formula ##STR1## wherein n represents a whole number of 1 to 5;X.sup.1 represents phenyl or phenyl mono-, di- or tri-substituted by R.sup.1, R.sup.2 and R.sup.3 ;X.sup.2 represents hydrogen, lower-alkyl, phenyl or phenyl mono-, di- or tri-substituted by R.sup.1, R.sup.2 and R.sup.3 ;Y represents hydrogen, lower-alkyl, hydroxymethyl, carboxy or lower-alkoxycarbonyl;Z represents a group of the formula ##STR2## R.sup.1, R.sup.2 and R.sup.3 represent hydrogen, halogen, hydroxy, benzyloxy, lower-alkyl, lower-alkoxy, hydroxymethyl, amino, acylamino, lower-alkoxybenzylamino, nitro, carbamoyl, trifluoromethyl or lower-alkylsulphonylmethyl;R.sup.4, R.sup.5 and R.sup.51 represent hydrogen, lower-alkyl, lower-alkoxy, lower alkanoyl, carboxy, cyano, hydroxy, hydroxy-lower-alkyl, acyloxy or a group --C(R.sup.6).dbd.C(R.sup.7)COOR.sup.8, --SO.sub.2 R.sup.9, --C(O)R.sup.9 or --CH.sub.2 R.sup.10, with the proviso that R.sup.4 does not represent hydrogen when R.sup.Type: GrantFiled: August 1, 1983Date of Patent: April 29, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
-
Patent number: 4584301Abstract: Novel chemical compounds which are diphenylmethylene piperidine compounds are provided, as well as methods for their production, pharmaceutical compositions comprising the compounds, and methods of treatment using the compounds in dosage form. The compounds have pharmacological properties especially anticholinergic properties, and are useful as antiemetic, antihistamine, pulmonary, antiallergy, and antispasmodic agents.Type: GrantFiled: May 16, 1985Date of Patent: April 22, 1986Assignee: Warner-Lambert CompanyInventors: David A. Downs, Haile Tecle
-
Patent number: 4576943Abstract: This disclosure describes certain pyrazolo[1,5-a]pyrimidines useful as hypotensive and/or anxiolytic agents, or as agents for the treatment of cognitive and related neural behavioral problems in mammals.Type: GrantFiled: October 9, 1984Date of Patent: March 18, 1986Assignee: American Cyanamid CompanyInventors: Andrew S. Tomcufcik, Walter E. Meyer, John P. Dusza, Shin S. Tseng
-
Patent number: 4564382Abstract: Compounds of the formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another denote hydrogen, F, Cl, Br or (C.sub.1 -C.sub.4)-alkyl, and R.sup.1 also denotes CF.sub.3, CN, NO.sub.2 or alkoxycarbonyl, A denotes a direct bond, --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, X denotes O, S or N--R.sup.8, R.sup.4 denotes H or alkyl, R.sup.5 and R.sup.6 denote alkyl, R.sup.7 denotes alkyl, (substituted) benzyl and/or (substituted) phenethyl and R.sup.8 denotes H or alkyl or, together with NR.sup.7, denotes a heterocyclic ring, are active herbicides and antidotes.Type: GrantFiled: November 8, 1984Date of Patent: January 14, 1986Assignee: Hoechst AktiengesellschaftInventors: Rainer Liebl, Reinhard Handte, Hilmar Mildenberger, Klaus Bauer, Hermann Bieringer
-
Patent number: 4558155Abstract: N-(Aryloxyalkyl)-N'-(aminoalkyl)ureas and thioureas having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, loweralkyl, cycloalkyl, phenyl or phenyllower alkyl, and R.sup.3 and R.sup.4 are hydrogen, loweralkyl, phenyl and phenylalkyl or R.sup.3 and R.sup.4 taken together with the adjacent nitrogen form a heterocyclic residue are disclosed in a method of suppressing cardiac arrhythmias.Type: GrantFiled: November 13, 1984Date of Patent: December 10, 1985Assignee: A. H. Robins Company, IncorporatedInventors: James R. Shanklin, Jr., Christopher P. Johnson, III
-
Patent number: 4543352Abstract: A class of naphthalene aminoalkylene ether and thioether compounds exhibiting pharmacological activity including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions are disclosed.Type: GrantFiled: April 29, 1983Date of Patent: September 24, 1985Assignee: William H. Rorer, Inc.Inventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt
-
Patent number: 4537621Abstract: Diphenyl ethers of the formula ##STR1## where Z.sup.1, Z.sup.2, and Z.sup.3 and R have the meanings given in the description, are used for controlling undesirable plant growth.Type: GrantFiled: March 31, 1983Date of Patent: August 27, 1985Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Hans Ziegler, Bruno Wuerzer
-
Patent number: 4537698Abstract: New piperidine derivatives ##STR1## in which R.sup.1 and R.sup.2 each independently is alkyl or alkoxy each of 1 to 10 C atoms, --Y--Z, F, Cl, Br or CN, and the radical R.sup.1 can also be H,Y is --CO--O--, --O--CO or a single bond,Z is --Q--R.sup.3 or alkyl having 1-10 C atoms,Q is 1,4-phenylene or 1,4-cyclohexylene,R.sup.3 is alkyl having 1-10 C atoms, F or CN, andA is 1,4-cyclohexylene or 1,3-dioxane-2,5-diyl, and their acid addition salts,can be used as components of dielectrics for electro-optical display elements.Type: GrantFiled: May 31, 1983Date of Patent: August 27, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Wolfgang Sucrow, Wolfgang Schatull, Peter Fuss
-
Patent number: 4504660Abstract: 2,6-Diaminobenzonitriles, useful in the production of N-(2-cyano-3-substituted or unsubstituted amino-phenyl)oxamate and N-(2-cyano-3-substituted or unsubstituted amino-phenyl)tetrazole-5-carboxamide antiallergy and antisecretory agents, are prepared by sequential displacement of the fluoro substituents from 2,6-difluorobenzonitrile with the appropriately substituted amine.Type: GrantFiled: July 6, 1982Date of Patent: March 12, 1985Assignee: American Home Products CorporationInventors: Dieter H. Klaubert, Stanley C. Bell
-
Patent number: 4500529Abstract: N-(Aryloxyalkyl)-N'-(aminoalkyl)ureas and thioureas having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, loweralkyl, cycloalkyl, phenyl or phenyllower alkyl, and R.sup.3 and R.sup.4 are hydrogen, loweralkyl, phenyl and phenylalkyl or R.sup.3 and R.sup.4 taken together with the adjacent nitrogen form a heterocyclic residue are disclosed in a method of suppressing cardiac arrhythmias.Type: GrantFiled: May 9, 1983Date of Patent: February 19, 1985Assignee: A. H. Robins Company, IncorporatedInventors: James R. Shanklin, Jr., Christopher P. Johnson, III
-
Patent number: 4491595Abstract: Trisubstituted cyanoguanidines of the formula ##STR1## in which R.sup.1 represents an optionally substituted phenyl or phenylalkyl radical, an alkyl radical with more than 1 carbon atom, a substituted alkyl radical, an alkenyl or alkinyl radical or an optionally substituted cycloalkyl radical,R.sup.2 represents an optionally substituted alkyl radical or an alkenyl or alkinyl radical andR.sup.3 represents an optionally substituted alkyl radical, an alkenyl or alkinyl radical, an optionally substituted cycloalkyl radical or an optionally substituted phenyl or phenylalkyl radical, orR.sup.2 and R.sup.3, together with the nitrogen atom to which they are bonded, represent an optionally substituted heterocyclic radical, which optionally contains an oxygen atom as a further hetero-atom,or a physiologically acceptable acid addition salt thereof, which possess fungicidal properties. Processes for their preparation are also taught.Type: GrantFiled: March 30, 1981Date of Patent: January 1, 1985Assignee: Bayer AktiengesellschaftInventors: Ekkehard Niemers, Winfried Lunkenheimer, Wilhelm Brandes
-
Patent number: 4487721Abstract: The present invention is directed to a process for producing 2-amino-2-arylacetonitriles of general formula I: ##STR1## wherein R and R.sup.1 independently represent hydrogen, hydroxy, hydroxy(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.6)alkyl, 2-furyl, 2-thienyl, 4-pyridinyl, 1-pyrrolydinyl, 1-piperidinyl, 4-morpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl, 4-phenylpiperazinyl, or phenyl which can optionally be substituted with from 1 to 3 substituents independently selected from (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy, or R and R.sup.1 independently represent a phenyl(C.sub.1 -C.sub.4)alkyl or a phenyl(C.sub.1 -C.sub.4)alkoxy group wherein the phenyl group can be either unsubstituted or substituted as above.An arylaldehyde derivative of formula II ##STR2## is reacted with chloroform in base and in the presence of ammonia to give the 2-amino-2-arylacetonitrile derivative.Type: GrantFiled: June 7, 1983Date of Patent: December 11, 1984Assignee: Gruppo Lepetit S.p.A.Inventor: Romeo Ciabatti
-
Patent number: 4482549Abstract: Compounds are described of the formula ##STR1## in which --COR.sup.1 is a complex ester or thioester group,W is alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,n is 1 or 2,Y is a saturated heterocyclic amino group having 5-8 ring members, andR.sup.2 is unsubstituted or substituted phenylalkyl, thienzlalkyl, naphthylalkyl or cinnamyl, and their salts and solvates.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and antiasthmatic agents.Type: GrantFiled: February 8, 1984Date of Patent: November 13, 1984Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes, John Bradshaw, Malcolm Carter, Alan Wadsworth
-
Patent number: 4447428Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.Type: GrantFiled: July 15, 1983Date of Patent: May 8, 1984Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Roger F. Newton
-
Patent number: 4444928Abstract: Polymers or oligometic compounds of the general formula ##STR1## in which X, X.sup.a and X.sup.b are an ester, amide or cyano group, Y, Y.sup.a and Y.sup.b are --O-- or --NR.sup.10 --, R.sup.1, R.sup.1a and R.sup.1b are a group which contains a polyalkylpiperidine radical, and R.sup.1a can also be alkyl, and R.sup.3, R.sup.3a and R.sup.3b are alkylene, alkenylene, arylene-dialkylene, cycloalkylene-dialkylene or monooxa-alkylene or polyoxa-alkylene, can be prepared by the polycondensation of malonic acid esters or amides or cyanoacetic acid esters or amides with difunctional compounds, preferably dihalogen compounds, in the presence of bases. The products obtained have a molecular weight of 800 to 20,000 and are outstanding light stabilizers for organic polymers.Type: GrantFiled: August 4, 1982Date of Patent: April 24, 1984Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
-
Patent number: 4427685Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: a is 1 to 3;b is 0 to 2;c is 2 to 4;d is 1 to 5;X is sulphur, oxygen or --CH.sub.2 --;Y is oxygen, sulphur, NR.sub.4 or CHR.sub.5 wherein R.sub.4 is hydrogen, C.sub.1-4 alkyl, NO.sub.2 or CN, C.sub.1-4 alkylsulphonyl or phenylsulphonyl optionally substituted in the phenyl moiety by one or two substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, fluorine, chlorine or bromine, and R.sub.5 is NO.sub.2, C.sub.1-4 alkylsulphonyl or optionally substituted phenylsulphonyl as defined for R.sub.4 ;R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1-4 alkyl, or C.sub.3-6 cycloalkyl; or R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached represent a pyrrolidino or piperidino ring;R.sub.6 and R.sub.7 are independently hydrogen or C.sub.Type: GrantFiled: February 3, 1982Date of Patent: January 24, 1984Assignee: Beecham Group P.L.C.Inventor: Geoffrey Stemp
-
Patent number: 4426521Abstract: Novel cyanoguanidine derivatives, and acid addition salts thereof useful as medicines which have pharmacological actions such as anti-secretory effect, local anesthesia action and the like; and process for the preparation thereof.Type: GrantFiled: January 28, 1982Date of Patent: January 17, 1984Assignee: Eisai Co., Ltd.Inventors: Satoru Tanaka, Katsutoshi Shimada, Kazunori Hashimoto, Kiichi Ema, Koichiro Ueda
-
Patent number: 4420614Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein A, B, D and E are chosen from hydrogen, halogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl and C.sub.1 to C.sub.6 alkoxy and Z is a tertiary or quaternary amino group.The compounds are useful intermediates for the preparation of pyrethroids. In further embodiments the invention provides processes for the preparation of the compounds of formula I and processes for the synthesis of pyrethroids utilizing the compounds of formula I.Type: GrantFiled: September 8, 1981Date of Patent: December 13, 1983Assignee: ICI Australia LimitedInventors: Colin Wilshire, Rene Jongen
-
Patent number: 4414220Abstract: 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: March 1, 1982Date of Patent: November 8, 1983Assignee: Pfizer Inc.Inventor: John L. Belletire
-
Patent number: 4410521Abstract: Compounds are described of the formula ##STR1## in which --COR.sup.1 is a complex ester or thioester group,W is alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,n is 1 or 2,Y is a saturated heterocyclic amino group having 5-8 ring members, andR.sup.2 is unsubstituted or substituted phenylalkyl, thienylalkyl, naphthylalkyl or cinnamyl,and their salts and solvates.These compounds inhibit blood platelet aggregation and bronchoconstruction and may be formulated for use as antithrombotic and antiasthmatic agents.Type: GrantFiled: September 16, 1982Date of Patent: October 18, 1983Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes, John Bradshaw, Malcolm Carter
-
Patent number: 4409213Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.Type: GrantFiled: November 10, 1982Date of Patent: October 11, 1983Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
-
Patent number: 4374779Abstract: The disclosed [[2-(substituted amino)-2-phenylethyl]nitrosoamino]acetonitrile derivatives and the ring closed oxadiazolium salts thereof as well as their pharmaceutically acceptable acid addition salts are antihypertensive agents useful in the treatment of hypertension.Type: GrantFiled: November 16, 1981Date of Patent: February 22, 1983Assignee: American Home Products CorporationInventor: Reinhardt P. Stein
-
Patent number: 4367239Abstract: The present invention relates to novel aminoalkyl substituted nitrosourea derivatives as well as their acid addition salts with pharmaceutically acceptable acids showing pronounced antineoplastic effectiveness in animal experiments.The novel compounds of the present invention may be represented by the following formula: ##STR1## wherein X and Y are the same or different, and are selected from the group consisting of a phenyl group and a cyclohexyl group, said phenyl and cyclohexyl groups being optionally substituted with one or two substituents selected from a halogen atom, a lower alkyl group having from one to four carbon atoms inclusive, a trifluore methyl group, a cyano group, a phenyl group, a cyclohexyl group and a lower alkyloxy group having from one to four carbon atoms inclusive."Alkylene" is an alkylene group, branched or unbranched, having from one to four carbon atoms inclusive, and R.sup.1 and R.sup.Type: GrantFiled: September 29, 1980Date of Patent: January 4, 1983Assignee: Kefalas A/SInventors: Peter Bregnedal, Jorn Buus
-
Patent number: 4360531Abstract: [2-Amino(substituted cycloaliphatic)]benzeneacetamide and benzamide compounds, e.g., trans-3,4-dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1,4-dioxaspiro[4.5]dec-8 -yl]benzeneacetamide, have useful analgesic activity and low abuse or physical dependence liability, or are useful as chemical intermediates for producing such analgesic compounds. Processes for their preparation are disclosed. Pharmaceutical compositions and methods of use are also disclosed.Type: GrantFiled: April 9, 1981Date of Patent: November 23, 1982Assignee: The Upjohn CompanyInventors: Moses W. McMillan, Jacob Szmuszkovicz
-
Patent number: 4359476Abstract: N-[2-Amino(oxy or thio group) substituted-cycloaliphatic]phenylacetamide and -benzamide compounds, having the oxy- or thio group substituents on a cycloaliphatic ring carbon adjacent to either of the nitrogen bearing carbons of the cycloaliphatic ring, e.g., cis- and trans-4-bromo-N-[3-methoxy-2-(1-pyrrolidinyl)cyclohexyl]-N-methylbenzamide , and trans-3,4-dichloro-N-methyl-N-[7-(1-pyrridolinyl)-1,4-dioxaspiro[4.5]dec-6 -yl]benzeneacetamide, and salts thereof, have useful analgesic activity and low abuse liability in humans and valuable warm blooded animals. Processes for their production and pharmaceutical compositions and method of use are also disclosed.Type: GrantFiled: April 9, 1981Date of Patent: November 16, 1982Assignee: The Upjohn CompanyInventors: Lester J. Kaplan, Moses W. McMillan, Jacob Szmuszkovicz
-
Patent number: 4350518Abstract: Substituted alkylammonium salts of the formula ##STR1## where Ar denotes substituted phenyl, X denotes oxygen or sulfur, n denotes one of the integers 0, 1 and 2, B denotes bicyclic quinuclidine, bicyclic pyrrolizidine or substituted ammonium, and Z denotes the anion of a nonphytotoxic acid, the manufacture of these compounds, and their use as plant growth regulators.Type: GrantFiled: February 23, 1981Date of Patent: September 21, 1982Assignee: BASF AktiengesellschaftInventors: Hubert Sauter, Bernd Zeeh, Ernst Buschmann, Johann Jung
-
Patent number: 4349452Abstract: Anisotropic compounds of the formula (1) ##STR1## wherein X and Y are each hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, N-monoalkaylamine having 1 to 12 carbon atoms in the alkyl group, halogen, cyano, nitro, or a cyclic radical of the formula ##STR2## wherein R is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.12 alkyl, or C.sub.1 -C.sub.12 alkoxy, Z.sup.1 is a --COO-- group or a --OOC-- group and Z.sup.2 may be the same as Z.sup.1 or a single convalent bond, with the proviso that:(a) only one of the groups X and Y is a cyclic radical, and(b) neither of the groups X or Y is hydrogen, bromine, or poperidino when the other is hydrogen, have low .DELTA.n-values without a greay tendency to form smectic phases and are useful in preparing liquid crystal devices.Type: GrantFiled: July 15, 1980Date of Patent: September 14, 1982Assignee: Merck Patent GmbHInventors: Maged A. Osman, Laszlo Revesz
-
Patent number: 4348401Abstract: An N-phenoxyalkylpiperidine derivative of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, an acyl radical or an optionally substituted aryl radical, R.sub.2 is a hydroxymethyl radical, a cyano group, an amidino group, an amidino group substituted by hydroxyl, a 1H tetrazol-5-yl radical or a --CO--R.sub.3 radical, R.sub.3 is a hydroxyl group, a lower alkoxy radical, an amino group, or an amino group substituted by a 1H-tetrazol-5-yl radical, X is an imino group or an oxymethyl radical, A is an alkylene radical containing 2 to 4 carbon atoms, and B is a valency bond or a 4-hydroxypyrimidin-2,5-diyl radical; or a pharmacologically acceptable salt thereof. The compounds exhibit anti-histaminic, anti-oedematous and anti-phlogistic activity.Type: GrantFiled: September 10, 1980Date of Patent: September 7, 1982Assignee: Boehringer Mannheim GmbHInventors: Walter-Gunar Friebe, Wolfgang Kampe, Max Thiel, Wolfgang Schaumann, Otto-Henning Wilhelms
-
Patent number: 4342756Abstract: Compounds are described of the formula ##STR1## (and their salts and solvates) in which: X is cis or trans --CH.dbd.CH--;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.3 where R.sup.3 is H, C.sub.1-6 alkyl or C.sub.7-10 aralkyl;Y is a saturated heterocyclic amino group having 5-8 ring members; andR.sup.2 is C.sub.2-4 alkanoyl, C.sub.3-6 alkenyl (optionally substituted), C.sub.1-12 alkyl, or substituted or unsubstituted phenylalkyl, biphenylalkyl or naphthylalkyl.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and anti-asthmatic agents.Type: GrantFiled: April 29, 1981Date of Patent: August 3, 1982Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw, Norman F. Hayes
-
Patent number: 4317819Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.Type: GrantFiled: December 5, 1980Date of Patent: March 2, 1982Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Barry J. Price, John Bradshaw, Michael Martin-Smith
-
Patent number: 4310346Abstract: This invention relates to N(Substituted Phenylsulfonyl) N'(Substituted Pyrimidinyl) urea compounds having the formulae I and IA ##STR1## to agricultural compositions containing them and to their methods of use as general as well as selective pre- and post-emergence herbicides and as plant growth regulants.Type: GrantFiled: May 30, 1980Date of Patent: January 12, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: George Levitt, Richard F. Sauers
-
Patent number: 4308400Abstract: Aromatic-aliphatic ketones of the formulae I, II, III or IV ##STR1## wherein n is 1 or 2, Ar is an aryl radical, R.sup.1 and R.sup.2 are monvalent aliphatic, cycloaliphatic or araliphatic radicals, R.sup.3 is a direct bond or a divalent organic radical, X is a hydroxyl or amino group or the monovalent etherification or silylation products thereof, and X' is a divalent amino, ether or silyloxy group, Y is a direct bond or CH.sub.2 and Z is O, S, SO.sub.2, CH.sub.2 or C(CH.sub.3).sub.2, are suitable sensitizers for the photopolymerization of unsaturated compounds and for the photochemical crosslinking of polyolefins. Some of these compounds are novel and can be obtained by methods analogous to those for obtaining the known compounds of this type.Type: GrantFiled: December 28, 1979Date of Patent: December 29, 1981Assignee: Ciba-Geigy A.G.Inventors: Louis Felder, Rudolf Kirchmayr, Rinaldo Husler
-
Patent number: 4283538Abstract: In one embodiment, the present invention is concerned with novel triarylmethane compounds possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group; R' is selected from ##STR2## wherein R" is methyl, unsubstituted or substituted with one or two halo groups or substituted with a phenyl, alkoxy or phenoxy group and ##STR3## wherein Y is an electron-withdrawing group; and R and R' taken with said ##STR4## represents ##STR5## In another embodiment the present invention is concerned with a method of synthesizing the aforementioned compounds by reacting, e.g., a 2-R'-3-(4'-hydroxy-1'-phenyl/naphthyl)-3-(phenyl/naphthyl)-2,3-dihydrobenz [d]isothiazole-1,1-dioxide with an alkylation reagent in the presence of base.Type: GrantFiled: December 26, 1979Date of Patent: August 11, 1981Assignee: Polaroid CorporationInventor: James W. Foley
-
Patent number: 4277471Abstract: Biphenylylalkylamines which have anti-arrhythmic activity have been prepared. Pharmaceutical formulations containing such compounds and a method of treating cardiac arrhythmias are provided.Type: GrantFiled: February 22, 1980Date of Patent: July 7, 1981Assignee: Eli Lilly and CompanyInventors: William B. Lacefield, Richard L. Simon
-
Patent number: 4264614Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, =CHNO.sub.2 or =NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.Type: GrantFiled: November 16, 1979Date of Patent: April 28, 1981Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Barry J. Price, John Bradshaw
-
Patent number: 4252814Abstract: There are provided novel cyanomethyl thioester compounds useful as ovicidal and larvicidal agents effective for the control of insects.Type: GrantFiled: July 5, 1979Date of Patent: February 24, 1981Assignee: American Cyanamid CompanyInventors: Peter J. Wepplo, Donald P. Wright, Jr.
-
Patent number: 4248779Abstract: A thiolcarbamate having the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and respectively represent an alkyl, alkoxy, alkenyl, cycloalkyl, hydroxyalkyl, phenyl or benzyl group and R.sub.1 and R.sub.2 can form a ring by binding each other with or without oxygen atom; and R.sub.3 represents a lower alkyl or benzyl group or a substituted benzyl group having one or two substituent of halogen atom, alkyl, alkoxy, alkylthio, nitro, or cyano group, which comprises reacting carbonyl sulfide with a sec-amine having the formula ##STR2## wherein R.sub.1 and R.sub.2 are defined above, in an aqueous medium and then reacting a halogenated hydrocarbon having the formulaX--R.sub.3 (IV)wherein R.sub.3 is defined above and X represents a halogen atom, in an aqueous medium.Type: GrantFiled: October 4, 1978Date of Patent: February 3, 1981Assignee: Ihara Chemical Industry Company, LimitedInventors: Zenichi Sato, Fumiya Tabuchi, Keiichiro Takagi, Yoji Imamiya
-
Patent number: 4242261Abstract: This invention provides an improved process for producing methylene-cycloamines as exemplified by 1-isopropyl-3-diphenylmethyleneacetidine: ##STR1## In accordance with the invention process, the above illustrated methyleneazetidine compound is synthesized by (1) reacting .alpha.,.alpha.-diphenyl-.alpha.-(1-isopropyl-3-azetidinyl) acetamide with bromine and alkali metal alkoxide under modified Hofmann Rearrangement conditions to form a carbamate intermediate, and (2) heating the carbamate intermediate in an acidic medium to yield the 1-isopropyl-3-diphenylmethyleneazetidine product.This illustrated 3-methyleneazetidine compound is characterized by a combination of pharmacological properties which are indicative of utility as a mood elevating therapeutic agent for relieving the symptoms of depression in humans.Type: GrantFiled: July 19, 1979Date of Patent: December 30, 1980Assignee: A. H. Robins Company, Inc.Inventor: Albert D. Cale, Jr.
-
Patent number: 4238613Abstract: Polyalkylpiperidinylesters and N-polyalkylpiperidinylamides of substituted malonic acids, methane tricarboxylic acids, .beta.-keto-, .alpha.-cyano-, .alpha.-phosphono- or .alpha.-sulfonocarboxylic acids are excellent stabilizers for polymers, especially against photochemical degradation. Polymers which can be stabilized in this way very effectively are polyolefins, styrene homo- and copolymers, polyamides and polyurethanes.Type: GrantFiled: October 13, 1978Date of Patent: December 9, 1980Assignee: Ciba-Geigy CorporationInventors: Michael Rasberger, Friedrich Karrer
-
Patent number: 4233302Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, N-oxides, hydrates and bioprecursors thereof, in whichY represents .dbd.O, .dbd.S, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 represents hydrogen, nitro, cyano, lower alkyl, aryl, lower alkylsulphonyl or arylsulphonyl;R.sub.1 and R.sub.2, which may be the same or different, each represent hydrogen lower alkyl, cycloalkyl, lower alkenyl, aralkyl, hydroxy, lower trifluoroalkyl, lower alkyl substituted by hydroxy, lower alkoxy, amine, lower alkylamino or dialkylamino, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a 5 to 7 membered heterocyclic ring which may contain other heteroatoms or the group ##STR2## where R.sub.Type: GrantFiled: December 18, 1978Date of Patent: November 11, 1980Assignee: Glaxo Group LimitedInventors: Michael Martin-Smith, Barry J. Price, John Bradshaw, John W. Clitherow
-
Patent number: 4232152Abstract: Amine salts of tertiary amino acids have been found to be effective as catalysts for polyurethane synthesis and they have been found to exhibit delayed action, in many instances, in the polymerization of urethanes. Typically, the amine salts of tertiary amino acids are formed by initially reacting a primary or secondary amine with an aldehyde and disubstituted acid to form a Mannich adduct and then reacting the resulting Mannich acid adduct with an amine.Type: GrantFiled: October 23, 1978Date of Patent: November 4, 1980Assignee: Air Products and Chemicals, Inc.Inventors: Ibrahim S. Bechara, Rocco L. Mascioli, Philip J. Zaluska
-
Patent number: 4226999Abstract: A compound of the formula I ##STR1## in which R.sub.2 is an optionally substituted 4-piperidinyl bonded via oxy or imino, or an optionally substituted 2-(piperidino)-ethoxy, n is 1 or 2, R.sub.7 and R.sub.8 are hydrocarbon radicals, R.sub.9 is hydrogen or methyl, R.sub.14 is cyano, --CH.sub.2 OH, a hydroxymethyl which is C-substituted by an optionally substituted 4-piperidinyl bonded via oxy or imino, or by an optionally substituted 2-(piperidino)-ethoxy, or R.sub.14 is also acyl or nitro, and, when n=1, R.sub.15 is hydrogen, a substituted hydroxybenzyl, an optionally substituted hydrocarbon radical, an optionally substituted 4-piperidinyl, or alkylene which is optionally linked to R.sub.14 and optionally substituted, or, when n=2, R.sub.15 is a direct bond or an optionally interrupted hydrocarbon radical, and its salts as stabilizers for organic material.Type: GrantFiled: January 5, 1979Date of Patent: October 7, 1980Assignee: Ciba-Geigy CorporationInventors: Roger Malherbe, Michael Rasberger
-
Patent number: 4225608Abstract: Phenoxyalkylamines of the formulaAr--O--Rwherein Ar is phenyl or phenyl which is monosubstituted or disubstituted by F, Cl, Br, alkyl or alkoxy each of 1-4 carbon atoms, cycloalkoxy of 3-6 carbon atoms, CF.sub.3, CN, alkylthio of 1-4 carbon atoms, SCF.sub.3, OH and/or alkanoyloxy with 1-10 carbon atoms; R is (1-R.sup.1 -2-pyrrolidyl)--CH.sub.2 --CHR.sup.2 --, (1-R.sup.1 -2-piperidyl)-CH.sub.2 --CHR.sup.2 -- or 1-R.sup.1 -3-Z-4-hexahydroazepinyl; R.sup.1 is H, alkyl or alkenyl each of up to 4 carbon atoms, cyclopropylmethyl or benzyl; R.sup.2 is H, alkyl of 1-4 carbon atoms or phenyl; and Z is alkyl of 1-4 carbon atoms with the proviso that Ar is p-fluorophenyl only if R is not 2-(1-methyl-2-piperidyl)-ethyl; and the physiologically acceptable acid addition salts thereof, possess valuable pharmacological properties, e.g., are antidepressants.Type: GrantFiled: March 16, 1979Date of Patent: September 30, 1980Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Jurgen Uhl, Dieter Marx, Hans-Heinrich Hausberg, Wighard Strehlow, Klaus-Otto Minck, Helmut Muller-Calgan, Christoph Seyfried
-
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
-
Patent number: 4198420Abstract: Novel spiro[dibenz(b,f)thiepin-piperidine]s and methods of preparing same are described. These compounds are useful as analgetics, tranquilizers and anticonvulsants.Type: GrantFiled: January 10, 1979Date of Patent: April 15, 1980Assignee: American Hoechst CorporationInventors: Helen H. Ong, James A. Profitt
-
Patent number: 4197312Abstract: This disclosure describes new compounds and compositions of matter useful as anti-inflammatory agents and as inhibitors of the progressive joint deterioration characteristic of arthritic disease and the methods of meliorating inflammation and of inhibiting joint deterioration in mammals therewith, the novel active ingredients of said compositions of matter being the pharmacologically acceptable cationic salts of benzoylacetonitrile, o-fluorobenzoylacetonitrile, m-fluorobenzoylacetonitrile, p-fluorobenzoylacetonitrile, or mixtures thereof.Type: GrantFiled: May 9, 1978Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventors: Adolph E. Sloboda, John W. Hanifin, Jr.
-
Patent number: 4194045Abstract: This invention encompasses novel 1-(3,3-diaryl-3-oxadiazolalkyl)-4-phenyl-4-piperidinomethanols and related compounds. These compounds are useful anti-diarrheal agents which possess little or no analgesic activity.Type: GrantFiled: December 27, 1977Date of Patent: March 18, 1980Assignee: G. D. Searle & Co.Inventor: Gilbert W. Adelstein
-
Patent number: 4191765Abstract: Compounds of formula I ##STR1## wherein R.sup.1 and R.sup.1' are identical or different and represent hydrogen, an alkyl radical or alkoxy radical having 1-4 carbon atoms, the allyl group, a halogen atom or the nitro group, R.sup.2 represents an acrylic acid radical or an acrylic acid nitrile radical of the formulae ##STR2## wherein R.sup.5 represents hydrogen, an alkyl radical having 1-5 carbon atoms, an aryl radical or aryl-lower alkyl radical either unsubstituted or substituted by lower alkyl or alkoxy, R.sup.6 represents hydrogen or an alkyl radical having 1-8 carbon atoms, R.sup.7 represents hydrogen, a lower alkyl radical or an aryl-lower alkyl radical, R.sup.3 and R.sup.4 represent together with the nitrogen atom a heterocyclic ring with 5-7 members being optionally substituted by C.sub.1 -C.sub.4 alkyl, in which ring one carbon atom may be replaced by one oxygen atom, sulfur atom or one further nitrogen atom, the latter may be substituted, or wherein R.sup.3 represents hydrogen and R.sup.Type: GrantFiled: August 10, 1978Date of Patent: March 4, 1980Assignee: Hoechst AktiengesellschaftInventors: Werner Fritsch, Ulrich Stache, Ernst Lindner
-
Patent number: 4189495Abstract: The invention provides novel 2-methoxy-benzamide derivatives of the formula: ##STR1## in which n is 1 or 2; R.sub.1 represents a cycloalkyl-alkyl radical of formula: ##STR2## a phenylalkyl radical of formula ##STR3## (in which m is an integer from 2 to 5, A is a linear or branched alkylene chain of 1 to 4 carbon atoms, and R.sub.4 is hydrogen, halogen, especially fluorine or chlorine, trifluoromethyl, or alkyl or alkoxy of 1 to 3 carbon atoms), CNCH.sub.2 --CH.sub.2 --, CH.tbd.C--CH.sub.2 --, ##STR4## R.sub.2 is either chlorine, SO.sub.2 R.sub.5 (in which R.sub.5 is alkyl of 1 to 4 carbon atoms), or SO.sub.2 NR.sub.6 R.sub.7 (in which, R.sub.6 and R.sub.7, which are identical or different, represent, independently of one another, hydrogen or alkyl of 1 to 4 carbon atoms); and R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms; in the form of racemates or optical isomers, and their pharmaceutically acceptable acid addition salts, which are useful in the treatment of psychosomatic and pyschotic disturbances.Type: GrantFiled: October 4, 1978Date of Patent: February 19, 1980Assignee: SynthelaboInventors: Jean-Pierre Kaplan, Bernard M. Raizon, Daniel C. L. Obitz, Philippe M. J. Manoury, Henry Najer, Maurice Jalfre, Don P. R. L. Giudicelli