The Chalcogen Is In A Substituent Attached To The Ring Nitrogen Of The Five Membered Hetero Ring Patents (Class 548/574)
  • Patent number: 6133455
    Abstract: 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: Grant
    Filed: February 9, 1999
    Date of Patent: October 17, 2000
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 6130242
    Abstract: 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: Grant
    Filed: December 29, 1998
    Date of Patent: October 10, 2000
    Assignee: Sepracor Inc.
    Inventors: Vincent L. Fabiano, John R. McCullough
  • Patent number: 6075146
    Abstract: The invention relates to intermediates and processes for producing benzothiophenes employing hydroxylamines.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: June 13, 2000
    Assignee: Eli Lilly and Company
    Inventor: Erik Christopher Chelius
  • Patent number: 5972939
    Abstract: 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: Grant
    Filed: October 26, 1998
    Date of Patent: October 26, 1999
    Assignee: Ortho-McNeil Pharmaceutical, Inc.
    Inventors: Robert H. Chen, Min Xiang, John B. Moore, Jr., Mary Pat Beavers
  • Patent number: 5856492
    Abstract: 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: Grant
    Filed: January 5, 1998
    Date of Patent: January 5, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Cheng Yi Chen, Feng Xu, Richard D. Tillyer, Dalian Zhao
  • Patent number: 5756762
    Abstract: 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: Grant
    Filed: January 9, 1997
    Date of Patent: May 26, 1998
    Assignee: Merrell Pharmaceuticals Inc.
    Inventor: H. Michael Kolb
  • Patent number: 5747523
    Abstract: 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: Grant
    Filed: January 24, 1996
    Date of Patent: May 5, 1998
    Assignee: Guilford Pharmaceuticals Inc.
    Inventor: Paul F. Jackson
  • Patent number: 5739157
    Abstract: 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: Grant
    Filed: July 25, 1996
    Date of Patent: April 14, 1998
    Assignee: Zeneca Limited
    Inventors: Stephen John Pegg, George Joseph Sependa, Elwyn Peter Davies, Chris Allan Veale
  • Patent number: 5686464
    Abstract: 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: Grant
    Filed: July 22, 1996
    Date of Patent: November 11, 1997
    Assignee: Pharmacia AB
    Inventors: Rolf Arne Johansson, Pinchas Moses, Lisbeth Nilvebrant, Bengt .ANG.ke Sparf
  • Patent number: 5543422
    Abstract: 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: Grant
    Filed: March 23, 1995
    Date of Patent: August 6, 1996
    Assignee: British Technology Group Limited
    Inventors: Ian G. C. Coutts, Pamela J. Cummins
  • Patent number: 5527821
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: June 18, 1996
    Assignee: Pharmacia AB
    Inventors: Nils-Erik Willman, Bengt C. H. Sjogren, Lennart G. Nordh, Gustav L. Persson
  • Patent number: 5500443
    Abstract: 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: Grant
    Filed: February 22, 1995
    Date of Patent: March 19, 1996
    Assignee: Adir et Compagnie
    Inventors: Gilbert Lavielle, Patrick Hautefaye, Olivier Muller, Mark Millan, Mauricette Brocco
  • Patent number: 5428056
    Abstract: 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: Grant
    Filed: November 12, 1993
    Date of Patent: June 27, 1995
    Assignee: Kuraray Co., Ltd.
    Inventors: Koichi Kanehira, Katsushi Eziri, Manzo Shiono, Yoshiji Fujita, Johji Yamahara
  • Patent number: 5416210
    Abstract: 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: Grant
    Filed: June 10, 1992
    Date of Patent: May 16, 1995
    Assignee: Rohm and Haas Company
    Inventors: Samuel E. Sherba, Raj J. Mehta, Margaret M. Bowers-Daines, Adam C. Hsu
  • Patent number: 5326873
    Abstract: 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: Grant
    Filed: June 5, 1992
    Date of Patent: July 5, 1994
    Assignee: Eastman Kodak Company
    Inventors: Stephen A. Godleski, Yann Hung
  • Patent number: 5286899
    Abstract: 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: Grant
    Filed: August 27, 1992
    Date of Patent: February 15, 1994
    Assignee: Sepracor, Inc.
    Inventor: Yun Gao
  • Patent number: 5250562
    Abstract: 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: Grant
    Filed: February 3, 1992
    Date of Patent: October 5, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 5155268
    Abstract: 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: Grant
    Filed: October 12, 1989
    Date of Patent: October 13, 1992
    Assignee: The Upjohn Company
    Inventor: Jackson B. Hester, Jr.
  • Patent number: 5129943
    Abstract: Disclosed herein are 2- or 6-fluoromethyl-3-pyridinecarboxylate derivatives with 5-[(heterocyclic)ylidene]amino substitution useful as herbicides and herbicide intermediates.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: July 14, 1992
    Assignee: Monsanto Company
    Inventors: Shridhar G. Hegde, Len F. Lee, Robert D. Bryant
  • Patent number: 5100911
    Abstract: 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: Grant
    Filed: May 15, 1990
    Date of Patent: March 31, 1992
    Assignee: Ebewe Arzneimittel Gesellschaft m.b.H.
    Inventors: Dieter Binder, Gerhard Greier, Franz Rovenszky, Friedrich Hillebrand
  • Patent number: 5071851
    Abstract: 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: Grant
    Filed: July 9, 1990
    Date of Patent: December 10, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Norbert Goetz, Bernhard Zipperer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 5019650
    Abstract: 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: Grant
    Filed: August 28, 1989
    Date of Patent: May 28, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Engelbert Ciganek, Leonard Cook
  • Patent number: 4999361
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: March 12, 1991
    Assignee: Boehringer Mannheim GmbH
    Inventors: Christos Tsaklakidis, Herbert Leinert, Peter Freund
  • Patent number: 4957927
    Abstract: 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: Grant
    Filed: September 22, 1989
    Date of Patent: September 18, 1990
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Gerard Ferrand, Jacques Barbanton, Jean-Claude Depin, Gilles Chavernac
  • Patent number: 4948805
    Abstract: 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: Grant
    Filed: November 9, 1987
    Date of Patent: August 14, 1990
    Assignee: Altergon S. A. & Ricerfarma Srl.
    Inventors: Antonio Ziggiotti, Michele Di Schiena
  • Patent number: 4910304
    Abstract: 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: Grant
    Filed: March 31, 1989
    Date of Patent: March 20, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Roman Fischer, Herbert Mueller, Dieter Voges
  • Patent number: 4910331
    Abstract: 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: Grant
    Filed: October 7, 1988
    Date of Patent: March 20, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kazuaki Kihara, Makoto Kuroda, Toshiyuki Nakamura
  • Patent number: 4902818
    Abstract: 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: Grant
    Filed: October 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4898941
    Abstract: 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: Grant
    Filed: August 11, 1987
    Date of Patent: February 6, 1990
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Nobuo Kanda, Haruo Omura, Yukihiro Abe, Mitsuru Kondo
  • Patent number: 4855423
    Abstract: Sulfatobetaines are prepared by reacting an addition compound of sulfur trioxide and a tertiary amine with an alkylene carbonate.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerold Braun, Chung-Ji Tschang, Christos Vamvakaris, Klaus Glaser
  • Patent number: 4845219
    Abstract: 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: Grant
    Filed: July 23, 1987
    Date of Patent: July 4, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Aono
  • Patent number: 4820820
    Abstract: 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: Grant
    Filed: September 23, 1987
    Date of Patent: April 11, 1989
    Assignee: L'Oreal
    Inventors: Henri Sebag, Guy Vanlerberghe
  • Patent number: 4820717
    Abstract: 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: Grant
    Filed: September 30, 1986
    Date of Patent: April 11, 1989
    Assignee: Sanofi
    Inventors: Madeleine Mosse, Henri Demarne, Vincenzo Proietto
  • Patent number: 4798894
    Abstract: 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: Grant
    Filed: May 11, 1987
    Date of Patent: January 17, 1989
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4758564
    Abstract: 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: Grant
    Filed: February 18, 1986
    Date of Patent: July 19, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Ernst Buschmann, Norbert Goetz, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4745190
    Abstract: 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: Grant
    Filed: March 31, 1986
    Date of Patent: May 17, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventor: John A. Marsella
  • Patent number: 4713456
    Abstract: 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: Grant
    Filed: August 26, 1985
    Date of Patent: December 15, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Graham Holmwood
  • Patent number: 4695631
    Abstract: 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: Grant
    Filed: June 30, 1982
    Date of Patent: September 22, 1987
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
  • Patent number: 4691007
    Abstract: 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: Grant
    Filed: December 6, 1985
    Date of Patent: September 1, 1987
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Anand S. Dutta, Ross L. Stein, Diane A. Trainor, Richard A. Wildonger
  • Patent number: 4680393
    Abstract: 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: Grant
    Filed: May 8, 1986
    Date of Patent: July 14, 1987
    Assignee: Air Products and Chamicals, Inc.
    Inventor: John A. Marsella
  • Patent number: 4650865
    Abstract: 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: Grant
    Filed: February 7, 1986
    Date of Patent: March 17, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Fritz Lange, Alfred Meffert
  • Patent number: 4632987
    Abstract: 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: Grant
    Filed: December 2, 1983
    Date of Patent: December 30, 1986
    Assignee: Mitsui Toatsu Chemicals Incorporated
    Inventors: Michihiro Tsujimoto, Hiroyuki Akahori, Kiyoharu Hasegawa, Makoto Asano
  • Patent number: 4602930
    Abstract: 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: Grant
    Filed: April 25, 1985
    Date of Patent: July 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Bernd Zeeh, Johann Jung, Hubert Sauter
  • Patent number: 4578462
    Abstract: 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: Grant
    Filed: August 22, 1983
    Date of Patent: March 25, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4482713
    Abstract: 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: Grant
    Filed: July 1, 1982
    Date of Patent: November 13, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Rainer Strickler
  • Patent number: 4430332
    Abstract: 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: Grant
    Filed: December 19, 1980
    Date of Patent: February 7, 1984
    Assignee: Centre Europeen de Recherches Mauvernay
    Inventors: Patrick Carlier, Andre J. C. Monteil, Jacques A. L. Simond
  • Patent number: 4420488
    Abstract: 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: Grant
    Filed: March 13, 1981
    Date of Patent: December 13, 1983
    Assignee: Ludwig Heumann & Co. GmbH
    Inventors: Walter Liebenow, Hans Liedtke
  • Patent number: 4417052
    Abstract: 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: Grant
    Filed: August 10, 1981
    Date of Patent: November 22, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4361573
    Abstract: .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: Grant
    Filed: March 11, 1981
    Date of Patent: November 30, 1982
    Assignee: Temmler AG
    Inventors: Wilhelm A. Behrendt, Bernhard Stieh