The Chalcogen Is In A Substituent Attached To The Ring Nitrogen Of The Five Membered Hetero Ring Patents (Class 548/574)
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Patent number: 6133455Abstract: There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl)methylamine compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control of insect and acarid pests, and may also be used to prepare other pesticidal arylpyrrole compounds.In addition, the present invention provides N-(arylmethylene)-1-chloro-1-(perfluoroalkyl)methylamine compounds which are useful as intermediates in the preparation of arylpyrrole compounds.Type: GrantFiled: February 9, 1999Date of Patent: October 17, 2000Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
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Patent number: 6130242Abstract: A method for treating urinary incontinence, such as incontinence resulting from bladder detrusor muscle instability, using enantiomerically enriched (S)-procyclidine. The method comprises administering a therapeutically effective amount of enantiomerically enriched (S)-procyclidine, or a pharmaceutically acceptable salt thereof, substantially free of the (R)-procyclidine enantiomer. Pharmaceutical compositions for the treatment of urinary incontinence comprising enantiomerically enriched (S)-procyclidine, or a pharmaceutically acceptable salt thereof, and an acceptable carrier are also disclosed.Type: GrantFiled: December 29, 1998Date of Patent: October 10, 2000Assignee: Sepracor Inc.Inventors: Vincent L. Fabiano, John R. McCullough
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Patent number: 6075146Abstract: The invention relates to intermediates and processes for producing benzothiophenes employing hydroxylamines.Type: GrantFiled: July 28, 1998Date of Patent: June 13, 2000Assignee: Eli Lilly and CompanyInventor: Erik Christopher Chelius
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Patent number: 5972939Abstract: The compounds of formula I are useful in treating gastrointestinal disorders associated with antagonizing the motilin receptor disorders. The compounds compete with erythromycin and motilin for the motilin receptor. In addition the compounds are antagonists of the contractile smooth muscle response to those ligands.Type: GrantFiled: October 26, 1998Date of Patent: October 26, 1999Assignee: Ortho-McNeil Pharmaceutical, Inc.Inventors: Robert H. Chen, Min Xiang, John B. Moore, Jr., Mary Pat Beavers
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Patent number: 5856492Abstract: An efficient method for the quantitative preparation and isolation of a compound of formula I ##STR1## or its enantiomer, a chiral mediator used in enantioselective synthesis.Type: GrantFiled: January 5, 1998Date of Patent: January 5, 1999Assignee: Merck & Co., Inc.Inventors: Cheng Yi Chen, Feng Xu, Richard D. Tillyer, Dalian Zhao
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Patent number: 5756762Abstract: The present invention relates to a novel enantiospecific processes for preparing (S)-4-amino-hepta-5,6-dienoic acid and pharmaceutically acceptable salts thereof, which is useful as an irreversible inhibitor of GABA-T, to novel intermediates thereof, and a process for preparing an intermediate thereof.Type: GrantFiled: January 9, 1997Date of Patent: May 26, 1998Assignee: Merrell Pharmaceuticals Inc.Inventor: H. Michael Kolb
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Patent number: 5747523Abstract: The invention relates to substituted ethyl .alpha.,.alpha.-diarylmethyl ether derivatives and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising the same, and methods of treating cocaine addiction and overdose, and diseases and conditions characterized by abnormal dopaminergic neurotransmission, using the same.Type: GrantFiled: January 24, 1996Date of Patent: May 5, 1998Assignee: Guilford Pharmaceuticals Inc.Inventor: Paul F. Jackson
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Patent number: 5739157Abstract: The present invention relates to pyrrolidine derivatives, and more particularly to the compound (S)-1-?(S)-2-(4-methoxybenzamido)-3-methylbutyryl!-N-?(S)-2-methyl-1-(trif luoroacetyl)propyl!pyrrolidine-2-carboxamide, shown by formula I, and solvates thereof. The present invention also provides pharmaceutical compositions, intermediates and methods of preparation of the compound. The compound of formula I is an inhibitor of human neutrophil elastase and is useful in the treatment of diseases in which the enzyme is implicated, such as, for example, emphysema and acute respiratory distress syndrome (ARDS).Type: GrantFiled: July 25, 1996Date of Patent: April 14, 1998Assignee: Zeneca LimitedInventors: Stephen John Pegg, George Joseph Sependa, Elwyn Peter Davies, Chris Allan Veale
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Patent number: 5686464Abstract: A 3,3-diphenylpropylamine of the formula I, or its physiologically acceptable acid salt thereof: ##STR1## wherein R.sup.1 represents hydrogen or methyl, R.sup.2 and R.sup.3 independently represent hydrogen, methyl, methoxy, hydroxy, carbamoyl, sulphamoyl or halogen, and X represents a tertiary amino group of formula II ##STR2## wherein R.sup.4 and R.sup.5 independently represent a hydroxy substituted or unsubstituted non-aromatic hydrocarbyl group which can join together to form a ring and which together contain at least three carbon atoms, wherein at least one of R.sup.4 and R.sup.5 is hydroxy substituted, is useful in treating acetylcholine-mediated disorders such as urinary incontinence.Type: GrantFiled: July 22, 1996Date of Patent: November 11, 1997Assignee: Pharmacia ABInventors: Rolf Arne Johansson, Pinchas Moses, Lisbeth Nilvebrant, Bengt .ANG.ke Sparf
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Patent number: 5543422Abstract: Heterocyclic amines of the formulaAr-X-A-NR.sup.1 R.sup.2wherein Ar is a bicyclic or tricyclic aromatic group which is unsubstituted or which bears one or more substituents selected from halo, nitro and cyano groups and alkyl and alkoxy groups each of up to 4 carbon atoms;wherein X is a direct link or is --O--, --S--, --SO-- or --SO.sub.2 -- or has the formula --C(R.sup.3).dbd.CH-- wherein R.sup.3 is hydrogen or alkyl of up to 4 carbon atoms;wherein A is straight or branched alkylene or alkenylene of 3 to 8 carbon atoms which may be interrupted by --O--, --S-- or --NH--;and wherein NR.sup.1 R.sup.2 is a cyclic amino group;or a pharmaceutically acceptable acid addition salt thereof, are of value for therapeutic use, particularly in the treatment of myocardial ischaemia and hypertension and in the treatment of fungal infections.Type: GrantFiled: March 23, 1995Date of Patent: August 6, 1996Assignee: British Technology Group LimitedInventors: Ian G. C. Coutts, Pamela J. Cummins
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Patent number: 5527821Type: GrantFiled: January 18, 1995Date of Patent: June 18, 1996Assignee: Pharmacia ABInventors: Nils-Erik Willman, Bengt C. H. Sjogren, Lennart G. Nordh, Gustav L. Persson
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Patent number: 5500443Abstract: A compound of formula (I): ##STR1## in which: X represents oxygen or methylene,n represents 1, 2 or 3,R.sub.1 represents hydrogen, aminocarbonyl or hydroxymethyl,R.sub.2 represents: ##STR2## in which R.sub.3 and R.sub.4 are as defined in the description, the isomers thereof and the addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same are useful in the treatment of schizophrenia.Type: GrantFiled: February 22, 1995Date of Patent: March 19, 1996Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Patrick Hautefaye, Olivier Muller, Mark Millan, Mauricette Brocco
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Patent number: 5428056Abstract: Novel terpene amino alcohols having an antiallergic activity or an activity of improving cerebral function are provided. Also provided are medicinal uses of the alcohols.Type: GrantFiled: November 12, 1993Date of Patent: June 27, 1995Assignee: Kuraray Co., Ltd.Inventors: Koichi Kanehira, Katsushi Eziri, Manzo Shiono, Yoshiji Fujita, Johji Yamahara
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Patent number: 5416210Abstract: In one aspect, compounds, methods of using them, compositions comprising such compounds, and uses of such compositions.These objects, and others which will become apparent from the following disclosure, are achieved by the present invention which comprises in one aspect compounds of the formula ##STR1## wherein R is alkyl, cycloalkyl, aryl, substituted aryl, alkaryl optionally substituted on the aryl portion or aralkyl optionally substituted on the aryl portion, R having up to 20 carbon atoms and is optionally branched, andA is (CH.sub.2).sub.p, (CH.sub.2).sub.q --O--(CH.sub.2).sub.r, or (CH.sub.2).sub.q --S--(CH.sub.2).sub.r,wherein p=2 to 8, q=1 to 8, and r=1 to 8.R.sub.1 =--(CH.sub.2).sub.m --, --(CH.sub.2 CH.sub.2 --O).sub.n --CH.sub.2 CH.sub.2 --, or --(CH.sub.2 CH.sub.2 CH.sub.2 --O).sub.n --CH.sub.2 CH.sub.2 CH.sub.2 --.Type: GrantFiled: June 10, 1992Date of Patent: May 16, 1995Assignee: Rohm and Haas CompanyInventors: Samuel E. Sherba, Raj J. Mehta, Margaret M. Bowers-Daines, Adam C. Hsu
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Patent number: 5326873Abstract: A method of forming 4-amino-2-buten-1-ol using 3,4-epoxy-1-butene is disclosed. A nitrogen nucleophile (e.g., an amine) is reacted with 3,4-epoxy-1-butene in the presence of a polymer-bound complex of palladium having up to four phosphine ligands.Type: GrantFiled: June 5, 1992Date of Patent: July 5, 1994Assignee: Eastman Kodak CompanyInventors: Stephen A. Godleski, Yann Hung
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Patent number: 5286899Abstract: An efficient and commercially-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.Type: GrantFiled: August 27, 1992Date of Patent: February 15, 1994Assignee: Sepracor, Inc.Inventor: Yun Gao
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Patent number: 5250562Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are lower-alkyl; or together are alkylene with 3-5 C-atoms in a straight chain; one of the residues R.sup.3 and R.sup.4 is hydrogen and the other is hydrogen or lower-alkyl; R.sup.6 and R.sup.7 are hydrogen or lower-alkyl; R.sup.5 and R.sup.8 are hydrogen, lower-alkyl, lower-alkoxy or halogen; X signifies --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sup.9 ; R.sup.9 is hydrogen, lower-alkyl or acyl; Y is --S(O).sub.m R.sup.10 or --NHet and, where X is --NR.sup.9 --, --S--, --SO-- or --SO.sub.2 --, also --N(R.sup.11).sub.2 or --OR.sup.12 ; R.sup.10 is lower-alkyl; R.sup.11 and R.sup.12 are hydrogen, lower-alkyl or acyl; --NHet is a 5-8 membered, saturated or unsaturated, monocyclic heterocycle attached via a N-atom; n is 2, 3 or 4 and m is 0, 1 or 2, are described. The compounds of formula I are useful as agents for the treatment of disorders such as neoplasms, dermatoses or ageing of the skin.Type: GrantFiled: February 3, 1992Date of Patent: October 5, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
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Patent number: 5155268Abstract: The present invention provides novel sulfonanilide and benzene-alkylaminium compounds which are the products of processes utilizing novel intermediates. Both the novel compounds and the novel intermediates are useful for the therapeutic or prophylactic treatment of arrhythmic activity.Type: GrantFiled: October 12, 1989Date of Patent: October 13, 1992Assignee: The Upjohn CompanyInventor: Jackson B. Hester, Jr.
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Patent number: 5129943Abstract: Disclosed herein are 2- or 6-fluoromethyl-3-pyridinecarboxylate derivatives with 5-[(heterocyclic)ylidene]amino substitution useful as herbicides and herbicide intermediates.Type: GrantFiled: May 20, 1991Date of Patent: July 14, 1992Assignee: Monsanto CompanyInventors: Shridhar G. Hegde, Len F. Lee, Robert D. Bryant
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Patent number: 5100911Abstract: Thienyloxyalkylamine derivatives of the general formula: ##STR1## wherein --O--CH.sub.2 --CH.sub.2 --NR.sub.2 R.sub.3 is in position 4 or 5 of the thiophene ring;R.sub.1 is hydrogen, halogen, CF.sub.3, alkyl or alkoxy;R.sub.2 and R.sub.3 are the same or different and are each alkyl, cycloalkyl, alkenyl or alkynyl each having up to 8 C atoms, or NR.sub.2 R.sub.3 is a 5 to 7-membered saturated heterocyclic ring optionally containing a further hetero atom which is oxygen or nitrogen optionally substituted by an alkyl group having 1 to 3 C atoms; andn is an integer of 1 to 5; as well as their acid addition salts, are suitable for treatment of heart rhythm disturbances.Type: GrantFiled: May 15, 1990Date of Patent: March 31, 1992Assignee: Ebewe Arzneimittel Gesellschaft m.b.H.Inventors: Dieter Binder, Gerhard Greier, Franz Rovenszky, Friedrich Hillebrand
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Patent number: 5071851Abstract: 4-substituted cyclohexylamines of the formula ##STR1## where R is the group CR.sup.1 R.sup.2 R.sup.3, where R.sup.1, R.sup.2 and R.sup.3 are hydrogen, unsubstituted or substituted alkyl, alkoxy, alkylthio or cycloalkyl, with the proviso that at most one of the substituents R.sup.1, R.sup.2 and R.sup.3 is hydrogen, X is an alkylene group which, together with the N atom, forms a substituted or unsubstituted heterocyclic ring in which up to 2 carbon atoms may be replaced by O, N or S atoms, and salts thereof, and fungicides containing these compounds.Type: GrantFiled: July 9, 1990Date of Patent: December 10, 1991Assignee: BASF AktiengesellschaftInventors: Ernst Buschmann, Norbert Goetz, Bernhard Zipperer, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 5019650Abstract: Known and novel 4-aryl-4-piperidinecarbinols and heterocyclic analogs are useful as analgesics. Also provided are novel pyrrolidinecarbinols and hexhydroazepine carbinols which are useful as analgesics, antidepressants and, in some cases, as anorectic agents.Type: GrantFiled: August 28, 1989Date of Patent: May 28, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Engelbert Ciganek, Leonard Cook
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Patent number: 4999361Abstract: The present invention provides compounds of the general formula ##STR1## wherein R.sub.1 is a hydrogen atom, a straight-chained or branched C.sub.1 -C.sub.12 -alkyl radical, a C.sub.3 -C.sub.7 -cycloalkyl radical, a straight-chained or branched C.sub.2 -C.sub.12 -alkenyl radical or an unsubstituted or substituted C.sub.3 -C.sub.7 -mono- or bicycloalkenyl radical, an unsubstituted or singly or multiple substituted monocyclic aromatic or heteroaromatic radical, R.sub.2 and R.sub.3, which can be the same or different, are straight-chained, branched, saturated or unsaturated C.sub.1 -C.sub.6 -aliphatic radicals or, together with the nitrogen atom to which they are attached, form a saturated or unsaturated ring which can contain further heteroatoms and can optionally be substituted by a lower alkyl radical, a lower alkoxy radical or an oxygen atom, R.sub.4 is an unsubstituted or singly or multiple substituted monocyclic aromatic radical, an unsubstituted or substituted five- or six-membered heteroaromatic ring, R.Type: GrantFiled: February 27, 1989Date of Patent: March 12, 1991Assignee: Boehringer Mannheim GmbHInventors: Christos Tsaklakidis, Herbert Leinert, Peter Freund
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Patent number: 4957927Abstract: 1-[(diarylmethoxy)alkyl]pyrrolidines and piperidines represented by the following formula: ##STR1## wherein X is hydrogen or a fluorine atom, Alk is a linear-chain or branched alkyl group having two or three carbon atoms; R.sub.1 and R.sub.2 are hydrogen or a linear-chain or branched alkoxy radical having 1 to 4 carbon atoms; n is 4 or 5.The compounds can be used as cardiovascular medicines.Type: GrantFiled: September 22, 1989Date of Patent: September 18, 1990Assignee: Lipha, Lyonnaise Industrielle PharmaceutiqueInventors: Gerard Ferrand, Jacques Barbanton, Jean-Claude Depin, Gilles Chavernac
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Patent number: 4948805Abstract: The salt of diclofenac with a cyclic organic base is prepared by dissolving diclofenac in a suitable organic solvent, adding said cyclic organic base, reacting the two components together, removing the solvent and crystallizing the product obtained.Said salt is water soluble to an extent from 20% w/v to an extent exceeding 50% w/v, and is used to prepared pharmaceutical compositions preferably in granular form for use by dissolving in water for oral administration.Type: GrantFiled: November 9, 1987Date of Patent: August 14, 1990Assignee: Altergon S. A. & Ricerfarma Srl.Inventors: Antonio Ziggiotti, Michele Di Schiena
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Patent number: 4910304Abstract: N-substituted cyclic amines of the general formula I ##STR1## where A is an alkylene group or a --(CH.sub.2).sub.n --[--O--(CH.sub.2).sub.m ].sub.r group which may be monosubstituted or polysubstituted by radicals R without the radicals R in a defined compound having to be identical, R is alkyl, alkoxyalkyl, unsubstituted or alkyl-substituted or alkoxy-substituted cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, n and m independently of one another are each from 2 to 8 and r is from 1 to 3, the --(CH.sub.2).sub.n --[O--(CH.sub.2).sub.m ].sub.r group consisting of from 5 to 12 members, are prepared by reacting a primary amine of the general formula IIR--NH.sub.Type: GrantFiled: March 31, 1989Date of Patent: March 20, 1990Assignee: BASF AktiengesellschaftInventors: Roman Fischer, Herbert Mueller, Dieter Voges
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Patent number: 4910331Abstract: This invention relates to a process for producing a thiolsulfonic acid derivative of the general formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is independently a lower alkyl group or a 5- or 6-membered cycloalkyl group, or alternatively R.sub.1 and R.sub.2 together with the adjacent nitrogen atom form a 5- or 6-membered heterocyclic group which may further contain an oxygen, sulfur or nitrogen atom; and R.sub.3 is (1) an aryl group which may optionally be substituted by a lower alkyl group, a halogen, a lower alkoxy group or a lower alkylthio group, (2) a lower alkyl group which may optionally be substituted by a lower alkoxy group, (3) an aralkyl group or (4) a cycloalkyl group, or a salt thereof, which comprises reacting a compound of the general formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, or a salt thereof with a compound of the general formula:R.sub.3 SO.sub.2 H (II)wherein R.sub.3 is as defined above, or a salt thereof under an acid condition.Type: GrantFiled: October 7, 1988Date of Patent: March 20, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kazuaki Kihara, Makoto Kuroda, Toshiyuki Nakamura
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Patent number: 4902818Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## in which R.sup.2 and R.sup.3 represents lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring, by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen, is described.The compounds of formula I are potential intermediates in the manufacture of, interalia, natural vitamin E and natural vitamin K.sub.1.Type: GrantFiled: October 5, 1988Date of Patent: February 20, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
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Patent number: 4898941Abstract: A process for preparing a diphenylalkene derivative of the formula [II] ##STR1## which comprises oxidizing a diphenylalkanoic acid derivative of the formula [I] ##STR2## wherein R.sub.1 and R.sub.2 are each substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl or substituted or unsubstituted aryl, R.sub.1 and R.sub.2 may form a heteroring together theirwith or with an adjacent benzene ring, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are each hydrogen atom, halogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyl or substituted or unsubstituted amino, R.sub.12 and R.sub.13 are each hydrogen atom or substituted or unsubstituted alkyl, X is carboxyl, amide, ester or halide thereof.Type: GrantFiled: August 11, 1987Date of Patent: February 6, 1990Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Nobuo Kanda, Haruo Omura, Yukihiro Abe, Mitsuru Kondo
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Patent number: 4855423Abstract: Sulfatobetaines are prepared by reacting an addition compound of sulfur trioxide and a tertiary amine with an alkylene carbonate.Type: GrantFiled: October 13, 1987Date of Patent: August 8, 1989Assignee: BASF AktiengesellschaftInventors: Gerold Braun, Chung-Ji Tschang, Christos Vamvakaris, Klaus Glaser
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Patent number: 4845219Abstract: A compound of the general formula [I]: ##STR1## wherein R.sub.1 represents a higher alkyl group or an N-(higher alkyl)carbamoyl group, R.sub.2 represents a lower alkyl group, an acyl group having at least three carbon atoms, an N-(lower alkyl)carbamoyl group, an N-(lower alkyl)thiocarbamoyl group or a benzyl group, R represents a primary, secondary or tertiary amino group or a quaternary ammonium group, x is 1 or 2, y is a number of 0, 1 or 2, and z is an integer of 2-10, or a pharmaceutically acceptable salt thereof. The novel substances have both anti-tumor activity and platelet activating factor-inhibiting property, and they are effective as an anti-tumor agent without circulatory trouble.Type: GrantFiled: July 23, 1987Date of Patent: July 4, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Aono
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Patent number: 4820820Abstract: Cationic surface-active products of the formula:R.sub.1 --O[C.sub.2 H.sub.3 (R.sub.2)O--].sub.p [C.sub.2 H.sub.3 (CH.sub.2 OH)O].sub.(n-1) CH.sub.2 --CHOH--CH.sub.2 --Gin which R.sub.1 =C.sub.4 -C.sub.20 aliphatic radical, R.sub.2 =C.sub.4 -C.sub.20 alkyl, alkoxymethyl or alkenyloxy radical, p=1-2.5, n=2-20 and G denotes an amine or amine oxide group, and their salts are disclosed for use principally in cosmetics.Type: GrantFiled: September 23, 1987Date of Patent: April 11, 1989Assignee: L'OrealInventors: Henri Sebag, Guy Vanlerberghe
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Patent number: 4820717Abstract: The present invention relates to new aromatic derivatives of formula: ##STR1## wherein: Alk is an alkylene group with 1 to 10 carbon atoms,R.sub.1 is hydrogen or an alkyl with 1 to 6 carbon atoms,R.sub.2 and R.sub.3 are similar or different and represent a cycloalkyl with 3 to 6 carbon atoms or a striaght or branched alkyl with 1 to 6 carbon atoms, either substituted or non-substituted by a phenyl or methyl phenyl group, or R.sub.2 and R.sub.3 form, together with the atom of nitrogen to which they are bonded, a mono-nitrogenous heterocycle containing no other heteroatom, such as pyrrolidino, piperidino, azepino, hexamethylene-imino, 4-methyl-piperidino, 4-phenyl-piperidino, 1,2,3,4-tetrahydro-2-isoquinolyl, 4-benzyl-piperidino;R.sub.4 is hydrogen, halogen, methyl or phenyl,R.sub.5 is hydrogen, halogen or methyl,or R.sub.4 and R.sub.5 together with the benzene ring to which they are bonded, constitute a 1-naphthyl or 2-naphthyl group,and the pharmaceutically acceptable salts with mineral or organic acids.Type: GrantFiled: September 30, 1986Date of Patent: April 11, 1989Assignee: SanofiInventors: Madeleine Mosse, Henri Demarne, Vincenzo Proietto
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Patent number: 4798894Abstract: Compounds containing at least one N,N-dialkylatable amino or amido group (e.g., aniline, dodecylamine, acetamide) are converted in a highly efficient manner into gem cyclodialkylated compounds by reaction with an unstrained cyclic ether (e.g., tetrahydrofuran) or a polyol (e.g., 1,4-butane diol) cyclizable to an unstrained ether using titanium dioxide catalysts that have prior to use:(1) a surface area of at least 70 square meters per gram (as determined by the BET method), and(2) the capability of chemically adsorbing at 100.degree. C. at least 35.times.10.sup.4 millimoles of gaseous ammonia per square meter of surface area.Type: GrantFiled: May 11, 1987Date of Patent: January 17, 1989Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4758564Abstract: Amines of the general formula ##STR1## where A is alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenylalkyl or phenylalkenyl, X is oxygen or sulfur, B is an alkylene chain and R.sup.1 and R.sup.2 are each alkyl, alkenyl or cycloalkyl, or R.sup.1 and R.sup.2 form part of a heterocyclic structrure, and their salts, as well as fungicides containing these compounds.Type: GrantFiled: February 18, 1986Date of Patent: July 19, 1988Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Ernst Buschmann, Norbert Goetz, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 4745190Abstract: Selective mono- or di-amination of alkanediols is controllably obtained by catalytic reaction with secondary amines at moderate temperature and autogenous pressure, by selection of the catalyst employed. Ruthenium complexes compounded or admixed with selected organic phosphines, such as triphenylphosphine, favor high yields of alkanolamines, while ruthenium complexes in the absence of organic phosphines favor production of alkylenediamines. Iridium complexes with or without organic phosphines in admixture or chemical combination, also promote production of alkylenediamines.Type: GrantFiled: March 31, 1986Date of Patent: May 17, 1988Assignee: Air Products and Chemicals, Inc.Inventor: John A. Marsella
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Patent number: 4713456Abstract: A process for the preparation of a 5-acylpyrimidine of the formula ##STR1## in which R is an organic radical comprising reacting a methyl ketone of the formulaR--CO--CH.sub.3in a first stage with a formylating reagent in the presence of a base to form an enolketone of the formulaR--CO--CH.dbd.CH--OR.sup.10in which R.sup.10 represents hydrogen or a base radical, thereafter reacting the enolketone in 2nd and 3rd stages with formamidine or a formamidine salt, and with an amino-formylating agent, and, in a 4th stage heating to cyclize the compound formed.The end products, some of which are new, are intermediates for making herbicides.Type: GrantFiled: August 26, 1985Date of Patent: December 15, 1987Assignee: Bayer AktiengesellschaftInventors: Hans-Ludwig Elbe, Graham Holmwood
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Patent number: 4695631Abstract: A process for the preparation of enamines or imines by isomerization of allylamine derivatives is described. Allylamine derivatives represented by formula (I): ##STR1## are isomerized using as a catalyst a rhodium complex represented by formula (IV):[Rh(olefin)L].sup.+ X.sup.- (IV)to form enamines or imines represented by, respectively, formula (II) or formula (III): ##STR2## All of the symbols in the above formulae are as described. These enamines or imines are useful intermediates for the preparation of a number of organic compounds.Type: GrantFiled: June 30, 1982Date of Patent: September 22, 1987Assignee: Takasago Perfumery Co., Ltd.Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
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Patent number: 4691007Abstract: Proline derivatives of the formulae: ##STR1## wherein R.sup.1 through R.sup.11 have defined values, and acid- and base-addition salts thereof, and equilibrium addition compounds of the aldehyde group thereof; processes for their preparation; pharmaceutical compositions; and intermediates for preparing said proline derivatives. The proline derivatives are human leukocyte elastase inhibitors which are useful, for example, in treating pulmonary emphysema.Type: GrantFiled: December 6, 1985Date of Patent: September 1, 1987Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Anand S. Dutta, Ross L. Stein, Diane A. Trainor, Richard A. Wildonger
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Patent number: 4680393Abstract: The present invention is a process for the synthesis of tertiary alkanolamines by reacting a secondary amine with an alkanediol. High selectivity for the production of alkanolamines is achieved by carrying out the reaction in the presence of a compound or complex of ruthenium in chemical combination or in admixture with an organic phosphine ligand. The organic phosphine ligand is present in an amount such that the ratio of gram mole ligand/gram atom ruthenium is greater than 5.Type: GrantFiled: May 8, 1986Date of Patent: July 14, 1987Assignee: Air Products and Chamicals, Inc.Inventor: John A. Marsella
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Patent number: 4650865Abstract: The invention relates to a process for preparing tertiary ether amines corresponding to the following general formula: ##STR1## by reacting in the presence of a strong base a tertiary amine corresponding to the following formula: ##STR2## with a sulfuric acid semi-ester salt corresponding to the following formula:R.sup.1 --(OC.sub.n H.sub.2n).sub.x --OSO.sub.3 M. (III)Preferably, each mole of the tertiary amine corresponding to formula (II) is reacted under substantially anhydrous conditions at a temperature of 140.degree. to 230.degree. C. with from about 0.2 to 3.0 moles of the sulfuric acid semi-ester salt of formula (III) in the presence of from about 1 to 1.5 moles of a strong base preferably an alkali metal hydroxide or an alkali metal alcoholate.Type: GrantFiled: February 7, 1986Date of Patent: March 17, 1987Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Fritz Lange, Alfred Meffert
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Patent number: 4632987Abstract: A process for the preparation of triarylmethane compounds which comprises reacting a benzene or naphthalene compound with a formylating agent for such compounds in the presence of an acid catalyst to form an aromatic aldehyde compound; adding water to the reaction mixture and thereby hydrolyzing the acid catalyst without isolating the aromatic aldehyde compound from the reaction mixture; and uninterruptedly condensing the aromatic aldehyde compound with an aromatic compound in the resulting mixture.Type: GrantFiled: December 2, 1983Date of Patent: December 30, 1986Assignee: Mitsui Toatsu Chemicals IncorporatedInventors: Michihiro Tsujimoto, Hiroyuki Akahori, Kiyoharu Hasegawa, Makoto Asano
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Patent number: 4602930Abstract: Phenylpropylammonium salts of the formula ##STR1## where R.sup.1 denotes for instance alkyl or halogen, R.sup.2 denotes for instance alkyl or alkoxy, R.sup.3 denotes alkyl, alkenyl or alkynyl of up to 6 carbon atoms, R.sup.4 and R.sup.5 denote hydrogen or alkyl of up to 3 carbon atoms, m denotes one of the integers 0, 1, 2 and 3, n denotes one of the integers 0, 1 and 2, o denotes one of the integers 4, 5 and 6, X.sup..theta. denotes an anion, and the dashed bond may be hydrogenated when n is 0 or 1, and is hydrogenated when n is 2; the preparation of these compounds; and agents for regulating plant growth containing these compounds as active ingredients.Type: GrantFiled: April 25, 1985Date of Patent: July 29, 1986Assignee: BASF AktiengesellschaftInventors: Ernst Buschmann, Bernd Zeeh, Johann Jung, Hubert Sauter
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Patent number: 4578462Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## or --CH.sub.2 --CH.dbd.NR.sup.2 in which R.sup.2 and R.sup.3 represent lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring,by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen,is described.The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K.sub.1.Type: GrantFiled: August 22, 1983Date of Patent: March 25, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
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Patent number: 4482713Abstract: Novel quaternary ammonium salts of the general formula[R.sup.1 R.sup.2 R.sup.3 N(A--O).sub.n --R.sup.4 ].sup.+ Z.sup.-where R.sup.1 and R.sup.2 are identical or different and each is alkyl, aryl, aralkyl, alkylaryl, alkoxyalkyl, or a (poly)alkylene glycol radical, or R.sup.1 and R.sup.2, together with the nitrogen atom, are a heterocyclic ring, or one or more substituents R.sup.1 or R.sup.2 are polyfunctional so that the salt contains not less than 2 ammonium groups, R.sup.3 and R.sup.4 are identical or different monovalent radicals of one or more alkylating agents R.sup.3 X or R.sup.4 X, for example an (ar)alk(en)yl halide, sulfate or methosulfate or an (alkyl)aryl-sulfonate or -sulfonic acid ester, A is alkylene of 2 to 10 carbon atoms, n is an integer and Z is either X or another salt-forming anion or a hydroxyl ion, are prepared by N-alkylation and O-alkylation of an alkanolamine with the aid of a phase transfer catalyst and are useful as cationic surfactants, etc.Type: GrantFiled: July 1, 1982Date of Patent: November 13, 1984Assignee: BASF AktiengesellschaftInventor: Rainer Strickler
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Patent number: 4430332Abstract: The invention is dealing with compounds of the formula: ##STR1## and pharmaceutically acceptable salts thereof, in which R.sub.1 and R.sub.2 each represent a lower alkyl radical or a phenyl radical, or, together with the carbon atom to which they are bound, a cycloalkyl radical having at the most 7 carbon atoms; R.sub.3 represents hydrogen, a lower alkyl radical, or the phenyl radical; R.sub.4 and R.sub.5 each represent a lower alkyl radical, or, together with the nitrogen atom to which they are bound, a heterocyclic amino radical such as the pyrrolidinyl or morpholino radicals; and R.sub.6 represents a lower alkyl radical, a phenyl radical, a benzyl radical, or the 1-ethynyl-cyclohexyl radical, which compounds can be used in the treatment of angina pectoris.Type: GrantFiled: December 19, 1980Date of Patent: February 7, 1984Assignee: Centre Europeen de Recherches MauvernayInventors: Patrick Carlier, Andre J. C. Monteil, Jacques A. L. Simond
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Patent number: 4420488Abstract: Quaternary 1,1-diphenyl-4-pyrrolidinium-2-butyne salts corresponding to the following general formula ##STR1## in which R represents methyl or ethyl and X is a chlorine or bromine atom, are described. These compounds are distinguished by improved spasmolytic and broncholytic activity.Type: GrantFiled: March 13, 1981Date of Patent: December 13, 1983Assignee: Ludwig Heumann & Co. GmbHInventors: Walter Liebenow, Hans Liedtke
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Patent number: 4417052Abstract: N-{2, 3- and 4-[R.sub.1 -(phenyl)-C(.dbd.X)]-phenyl-loweralkyl} amines, useful as anti-inflammatory agents, are prepared either by reduction of 2-, 3- or 4-[R.sub.1 -(phenyl)CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-loweralkylamine; by reaction of a 2-, 3- or 4-lithiophenyl-loweralkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)-lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile; by reaction of a 2-, 3- or 4-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkyl tosylate with an appropriate amine; or by transformations involving manipulations of a carbonyl or carbinol group.Type: GrantFiled: August 10, 1981Date of Patent: November 22, 1983Assignee: Sterling Drug Inc.Inventor: Bernard L. Zenitz
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Patent number: 4361573Abstract: .alpha.,.alpha.-Diaryl-.beta.-(tert-amino)-propanols having the general formula: ##STR1## wherein R', R" and R.sup.1 to R.sup.10 represent certain specific substituent groups, exhibit a diuretic and saluretic activity.Pharmaceutical composition containing at least one compound of the general Formula II together with a pharmaceutically acceptable diluent or carrier. The pharmaceutical compositions may be in a form suitable for oral or parenteral administration.Type: GrantFiled: March 11, 1981Date of Patent: November 30, 1982Assignee: Temmler AGInventors: Wilhelm A. Behrendt, Bernhard Stieh