Hydroxy Or Ether Oxygen Bonded Directly To The Aryl Ring Or Ring System (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/365)
  • Patent number: 9029421
    Abstract: The present invention provides a process for preparing a compound of formula (VI) or a salt thereof, the process comprising: (i) reacting 4-methoxyphenyl acetone with an amine of formula (VIII) under conditions of reductive amination to produce a compound of formula (II) or a salt thereof, wherein there is no isolation of an imine intermediate formed during the reductive amination; (ii) condensing the compound (II) or the acid addition salt thereof with an ?-haloketone of formula (III) to produce the compound of formula (IV); (iii) reducing the compound (IV) to a compound of formula (V); and (iv) reducing the compound (V) to the compound of formula (VI), wherein the reduction is carried out in the presence of either (1) a hydrogen donating compound in the presence of a hydrogen transfer catalyst; or (2) ammonium formate using a hydrogenation catalyst, wherein R1 and R2 are independently optionally substituted arylalkyl, and Hal is selected from chloro or bromo.
    Type: Grant
    Filed: June 2, 2009
    Date of Patent: May 12, 2015
    Assignee: Cipla Limited
    Inventors: Vaishali Vaman Haldavanekar, Mangesh Prabhu, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan
  • Publication number: 20120232033
    Abstract: The invention relates to the use of compounds of formula I wherein the substituents are described in the description and claims for the treatment of psychoses, dysfunction in memory and learning, schizophrenia, dementia, attention deficit disorders or Alzheimer's disease. The invention also relates to some compounds of formula I and pharmaceutical compositions containing them.
    Type: Application
    Filed: May 25, 2012
    Publication date: September 13, 2012
    Inventors: Sabine Kolczewski, Hans-Peter Marty, Robert Narquizian, Emmanuel Pinnard, Henri Stalder
  • Patent number: 7977378
    Abstract: Compositions and methods are provided for the treatment of obesity in a human in need of such treatment which comprises administration to the human of a therapeutically effective amount of a compound of a weight loss enhancing beta-3-adrenergic compound of Cycle I, and a different weight loss enhancing adenylate cyclase receptor replenishing compound of Cycle II, in conjunction with a pharmaceutically acceptable diluent or carrier, wherein the Compound of Cycle I and the compound of Cycle II are administered sequentially. The composition may be present as a kit having each sequence in blister packs.
    Type: Grant
    Filed: December 19, 2007
    Date of Patent: July 12, 2011
    Inventor: Adel Villalobos
  • Publication number: 20110166237
    Abstract: The present invention provides a process for preparing a compound of formula (VI) or a salt thereof, the process comprising: (i) reacting 4-methoxyphenyl acetone with an amine of formula (VIII) under conditions of reductive amination to produce a compound of formula (II) or a salt thereof, wherein there is no isolation of an imine intermediate formed during the reductive amination; (ii) condensing the compound (II) or the acid addition salt thereof with an ?-haloketone of formula (III) to produce the compound of formula (IV); (iii) reducing the compound (IV) to a compound of formula (V); and (iv) reducing the compound (V) to the compound of formula (VI), wherein the reduction is carried out in the presence of either (1) a hydrogen donating compound in the presence of a hydrogen transfer catalyst; or (2) ammonium formate using a hydrogenation catalyst, wherein R1 and R2 are independently optionally substituted arylalkyl, and Hal is selected from chloro or bromo.
    Type: Application
    Filed: June 2, 2009
    Publication date: July 7, 2011
    Applicant: CIPLA LIMITED
    Inventors: Vaman Vaishali Haldavanekar, Mangesh Prabhu, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan
  • Publication number: 20110152332
    Abstract: The present invention relates to novel pesticidal azolidine derivatives as well as to oxazolidinone derivatives and their use as pesticides for combating animal parasites which occur in the agrochemical field and in the field of veterinary medicine, respectively. wherein X, m, R?, Q, G, U, l, A1 to A4 and R are as defined herein.
    Type: Application
    Filed: November 1, 2010
    Publication date: June 23, 2011
    Applicant: Bayer CropScience AG
    Inventors: Tetsuya Murata, Mamoru Hatazawa, Peter Brüchner, Eiichi Shimojo, Teruyuki Ichihara, Masashi Ataka, Katsuhiko Shibuya, Ulrich Görgens
  • Publication number: 20110009631
    Abstract: Compounds of the formula (II) and (IV) are provided, which may be employed as intermediates for making compounds useful in treating respiratory diseases.
    Type: Application
    Filed: July 14, 2010
    Publication date: January 13, 2011
    Applicant: Glaxo Group Limited
    Inventors: Philip Charles Box, Diane Mary Coe, Brian Edgar Looker, Inderjit Singh Mann, Panayiotis Alexandrou Procopiou
  • Publication number: 20100222257
    Abstract: Disclosed herein are substituted phenethylamine alpha adrenergic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
    Type: Application
    Filed: May 17, 2010
    Publication date: September 2, 2010
    Applicant: AUSPEX PHARMACEUTICALS, INC.
    Inventors: Thomas G. Gant, Sepehr Sarshar
  • Patent number: 7745665
    Abstract: Disclosed herein are substituted phenethylamine alpha adrenergic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
    Type: Grant
    Filed: June 3, 2008
    Date of Patent: June 29, 2010
    Assignee: Auspex Pharmaceuticals, Inc.
    Inventors: Thomas G. Gant, Sepehr Sarshar
  • Publication number: 20090325915
    Abstract: The invention provides three polymorphic forms of crystalline levosalbutamol sulphate designated herein as Forms I, II and III. Crystalline levosalbutamol sulphate Form I is characterised by a powder XRD pattern with peaks at 10.8, 11.9, 13.0, 18.3, 28.5±0.2 degrees 2 theta. Crystalline levosalbutamol sulphate Form II is characterised by a powder XRD pattern with peaks at 8.7, 9.6, 15.2, 15.7, 19.1, 27.2, 30.7±0.2 degrees 2 theta. Crystalline levosalbutamol sulphate Form III is characterised by a powder XRD pattern with peaks at 5.5, 6.9, 7.3, 18.7±0.2 degrees 2 theta. Processes for making the new polymorphic forms and pharmaceutical compositions comprising them are also provided.
    Type: Application
    Filed: July 14, 2009
    Publication date: December 31, 2009
    Inventors: Dharmaraj Ramchandra Rao, Rajendra Narayanrao Kankan, Alka Chaudhary
  • Publication number: 20090047343
    Abstract: The present invention relates to a process for stabilizing phenylephrine including drying an acidic solution of phenylephrine and pharmaceutical compositions including stabilized phenylephrine.
    Type: Application
    Filed: August 13, 2007
    Publication date: February 19, 2009
    Inventors: Hugh Huang, Jonathan Zeszotarski, Anthony Bean, William Michael Nichols
  • Patent number: 7465831
    Abstract: The invention is directed to processes for making levalbuterol HCl Polymorph A from by suspending or forming a first slurry of (R)-SLB(D)-DBTA in at least a first organic solvent, adding HCl to the suspension or slurry of the solid (R)-SLB.D-DBTA until the (R)-SLB.D-DBTA forms levalbuterol HCl Polymorph A, and isolating the levalbuterol HCl Polymorph A.
    Type: Grant
    Filed: July 11, 2007
    Date of Patent: December 16, 2008
    Assignee: Teva Pharmaceutical Fine Chemicals s.r.l.
    Inventors: Valeriano Merli, Silvia Mantovani, Stefano Bianchi, Paola Daverio, Angelo Spreafico, Judith Aronhime, Adrienne Kovacsne-Mezei
  • Patent number: 7452995
    Abstract: The invention provides novel ?2 adrenergic receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with ?2 adrenergic receptor activity, and processes and intermediates useful for preparing such compounds.
    Type: Grant
    Filed: April 7, 2005
    Date of Patent: November 18, 2008
    Assignee: Theravance, Inc.
    Inventors: Edmund J. Moran, John R. Jacobsen, James Aggen
  • Publication number: 20080132579
    Abstract: Provided are processes for the preparation of (R)-SLB.D-DBTA salt and levalbuterol hydrochloride. Also provided are levalbuterol hydrochloride degradation products and processes for preparing them. Pharmaceutical compositions comprising at least one levalbuterol hydrochloride of the invention and at least one pharmaceutically-acceptable excipient are also provided.
    Type: Application
    Filed: December 27, 2007
    Publication date: June 5, 2008
    Inventors: Valeriano Merli, Silvia Mantovani, Stefano Bianchi, Paola Daverio
  • Patent number: 7135500
    Abstract: A compound of formula 1 wherein the groups R1, R2, R3, and R4 may have the meanings given in the claims and in the specification, processes for preparing them, and their use as pharmaceutical compositions, particularly for the treatment of inflammatory and obstructive respiratory complaints.
    Type: Grant
    Filed: October 30, 2003
    Date of Patent: November 14, 2006
    Assignee: Boehringer Ingelheim Pharma GmbH & Co KG
    Inventors: Ingo Konetzki, Kurt Schromm, Hermann Schollenberger, Sabine Pestel, Andreas Schnapp, Thierry Bouyssou, Frank Buettner, Claudia Heine
  • Patent number: 7084165
    Abstract: The present invention relates to compounds that are useful exhibit activity as serotonin, norepinephrine and dopamine reuptake inhibitors, and their pharmaceutically acceptable salts, and their use in the treatment of central nervous system and other disorders.
    Type: Grant
    Filed: September 4, 2003
    Date of Patent: August 1, 2006
    Assignee: Pfizer Inc
    Inventors: Harry Ralph Howard, Jr., Christopher Joseph Schmidt, Thomas Francis Seeger, Mark Leonard Elliot
  • Patent number: 6995286
    Abstract: A process for making optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.
    Type: Grant
    Filed: December 10, 2001
    Date of Patent: February 7, 2006
    Assignee: Cipla Limited
    Inventors: Yusuf Khwaja Hamied, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao
  • Patent number: 6900203
    Abstract: (R)-6F-phenylephrine, essentially free of (S)-6F-phenylephrine, and an anesthetic formulation comprising (R)-6F-epinephrin or (R)-6F-phenylephrine and having improved stability compared to formulations containing their non-fluorinated analog, are disclosed. Further disclosed is a method of providing vasoconstriction in a mammal by administering the anesthetic formulation. The anesthetic composition can include an anesthetic, an (R)-chiral compound having the structure: wherein R1, R2, and R4 are independently selected from —H or —F, at least one of R1, R2, and R4 is —F, and R3 is selected from —OH, —H or —F, or a pharmaceutically acceptable salt or ester thereof, said vasoconstrictor being essentially free of the (S)-chiral form. Also, a method of chiral addition of cyanide to a ring-fluorinated phenaldehyde, employing an almond hydroxynitrile lyase enzyme, provided in the form of a reversibly soluble polymer conjugate ((R)-Finezyme™-H series biocatalysts) is disclosed.
    Type: Grant
    Filed: July 8, 2002
    Date of Patent: May 31, 2005
    Assignee: Polium Technologies, Inc.
    Inventors: Hamilton J. Lenox, Elena Terentieva, Mikhail Y. Gololobov
  • Patent number: 6825382
    Abstract: Disclosed herein are trifluoromethylepinephrine compounds having the following structural formula (I) wherein R1-R5 are each independently selected from the group consisting of H, alkyl, alkoxyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, acyl, thioacyl, sulfonyl mercapto, alkylthio, carboxy, amino, alkylamino dialkylamino, carbamoyl, arylthio, and heteroarylthio; wherein X, Y, and Z are each independently selected from the group consisting of H or trifluoromethyl with the proviso that at least one of which is trifluoromethyl. Also disclosed are pharmaceutical compositions comprising the trifluoromethylepinephrine compounds and methods of making and using thereof. Novel trifluoroepinephrine intermediates are also disclosed.
    Type: Grant
    Filed: March 3, 2003
    Date of Patent: November 30, 2004
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Jeffrey R. Ammann
  • Patent number: 6730792
    Abstract: The present invention relates to a &bgr;3 adrenergic receptor agonist of formula (I) or a pharmaceutical salt thereof, which is capable of increasing lipolysis and energy expenditure in cells and, therefore, is useful for treating Type II diabetes and/or obesity. The compound can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compound can be used to reduced neurogenic inflammation or as an antidepressant agent. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for decreasing gut motility are also disclosed.
    Type: Grant
    Filed: December 13, 2002
    Date of Patent: May 4, 2004
    Assignee: Eli Lilly and Company
    Inventors: Britta Evers, Cynthia Darshini Jesudason, Rushad Eruch Karanjawala, David Michael Remick, Daniel Jon Sall, Miles Goodman Siegel, Wolfgang Stenzel, Russell Dean Stucky, John Arnold Werner
  • Publication number: 20040048856
    Abstract: The present invention relates to compounds that are useful exhibit activity as serotonin, norepinephrine and dopamine reuptake inhibitors, and their pharmaceutically acceptable salts, and their use in the treatment of central nervous system and other disorders.
    Type: Application
    Filed: September 4, 2003
    Publication date: March 11, 2004
    Applicant: Pfizer Inc
    Inventors: Harry R. Howard, Christopher J. Schmidt, Thomas F. Seeger, Mark L. Elliott
  • Patent number: 6653323
    Abstract: The invention provides novel &bgr;2 adrenergic receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with &bgr;2 adrenergic receptor activity, and processes and intermediates useful for preparing such compounds.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: November 25, 2003
    Assignee: Theravance, Inc.
    Inventors: Edmund J. Moran, John R. Jacobsen, James B. Aggen
  • Patent number: 6576793
    Abstract: Disclosed are multibinding compounds which are &bgr;2 adrenergic receptor agonists and are useful in the treatment and prevention of respiratory diseases such as asthma and bronchitis. They are also useful in the treatment of nervous system injury and premature labor.
    Type: Grant
    Filed: August 14, 2000
    Date of Patent: June 10, 2003
    Assignee: Theravance, Inc.
    Inventors: Edmund J. Moran, John H. Griffin, Seok-Ki Choi
  • Patent number: 6521667
    Abstract: The present invention features calcilytic compounds. “Calcilytic compounds” refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.
    Type: Grant
    Filed: August 11, 1998
    Date of Patent: February 18, 2003
    Assignees: NPS Pharmaceuticals, Inc., SmithKline Beecham, PLC, SmithKline Beecham, Corp.
    Inventors: Eric G. Del Mar, Robert M. Barmore, Derek Sheehan, Bradford C. Van Wagenen, James F. Callahan, Richard M. Keenan, Nikesh R. Kotecha, Maria Amparo Lago, Linda Sue Southall, Mervyn Thompson
  • Patent number: 6362371
    Abstract: The present invention is directed to multibinding compounds which are &bgr;2 adrenergic receptor agonists and are therefore useful in the treatment and prevention of respiratory diseases such asthma, bronchitis, and the like. They are also useful in the treatment of nervous system injury and premature labor.
    Type: Grant
    Filed: June 2, 1999
    Date of Patent: March 26, 2002
    Assignee: Advanced Medicine, Inc.
    Inventors: Edmund J. Moran, John H. Griffin, Seok-Ki Choi
  • Patent number: 5654331
    Abstract: Diaromatic compounds, characterised in that they correspond to the following general formula: ##STR1## in which: R.sub.1 is --CH.sub.3, --CH.sub.2 OH, --COR.sub.8 or --CH.sub.2 OCOR.sub.9, R.sub.8 is H, OH, --OR.sub.10, --N(rr') or alkyl, R.sub.10 is alkyl, alkenyl, aryl or aralkyl, r and r' being H, alkyl, aryl, aralkyl, etc., r and r' together form a heterocycle, R.sub.9 is alkyl, alkenyl or a sugar residue, R.sub.2 and R.sub.3 are --OR.sub.11 or --OCOR.sub.11, R.sub.11 is H, alkyl, fluoroalkyl, aryl or aralkyl, R.sub.3 in addition being H, R.sub.4 is H, OH, alkyl, alkoxy, F, Cl or --CF.sub.3, R.sub.5 and R.sub.7 are H, OH, alkoxy, .alpha.-substituted alkyl or .alpha.,.alpha.'-disubstituted alkyl, etc., R.sub.6 is H, OH, alkyl, alkoxy, cycloalkyl, etc., R.sub.5 and R.sub.7 cannot simultaneously be OH or alkoxy and R.sub.4, R.sub.5, R.sub.6 and R.sub.7 cannot simultaneously be H, R.sub.5 and R.sub.6 or R.sub.6 and R.sub.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: August 5, 1997
    Assignee: Centre International De Recherches Dermatologiques Galderma (Cird Galderma)
    Inventor: Jean-Michel Bernardon
  • Patent number: 5545745
    Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(phenylmethoxy)benzoate or .alpha.-[[(1,1-dimethylethyl)amino]methyl]-4-(phenylmethoxy)-1,3-benzenedi methanol using a chiral acid such as (+/-) di-toluoyltartaric acid or (+/-) di-benzoyltartaric acid.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: August 13, 1996
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Charles M. Zepp
  • Patent number: 5538999
    Abstract: A compacted body of powdered medicament for use in a device for the administration by inhalation of a medicament in powdered form. The compacted body is made by compressing a loose powder containing the medicament in powdered form under pressure to create sufficient structural integrity in the body to permit metering of several unit doses of the medicament by abrasion of the body in the device.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: July 23, 1996
    Assignee: Fisons plc
    Inventors: Andrew R. Clark, John L. Hart
  • 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: 5449694
    Abstract: (-)-Ritodrine, that is (-)-erythro-1-(p-hydroxyphenyl)-2-[2-(p-hydroxyphenyl)ethylamino]-1-propan ol or a salt thereof substantially free from the (+)-isomer is disclosed. The compound has a strong suppressive effect on uterine contraction in comparison with (.+-.)-ritodrine and (+)-ritodrine and has the same level of toxicity as these compounds, so that it can be used as a therapeutic agent of threatened premature birth and threatened abortion as well as a therapeutic agent of dysmenorrhea having a high safety.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: September 12, 1995
    Assignee: Meiji Seika Kabushiki Kaisha
    Inventors: Naoki Yamazaki, Yoshimasa Fukuda, Yoshiaki Shibazaki, Tetsutarou Niizato, Isao Kosugi, Shin Yoshioka
  • Patent number: 5442118
    Abstract: A method for the enantioselective reduction of an .alpha.-iminoketone to an .alpha.-aminoalcohol is disclosed. The method utilizes a borane reducing agent as the reducing agent and a chiral 1,3,2-oxazaborole as the catalyst. The method is applied to the synthesis of R-albuterol from methyl 5-acetylsalicylate in high yield and high optical purity.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: August 15, 1995
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
  • Patent number: 5399765
    Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoate using ditoluoyltartaric acid.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: March 21, 1995
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Charles M. Zepp
  • Patent number: 5243076
    Abstract: Phenethanolamine derivatives are disclosed of formula ##STR1## wherein m is 2 to 8; n is 1 to 7 provided that m+n is 4 to 12;Ar is phenyl or phenyl substituted by one or two halogen atoms, alkyl or alkoxy groups or by an alkylenedioxy group;R.sup.1 and R.sup.2 are hydrogen or alkyl provided that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 4;and the physiologically acceptable salts and solvates thereof.The compounds have a selective stimulant action at .beta..sub.2 -adrenoreceptors and may be used inter alia in the treatment of diseases associated with reversible airways obstructions such as asthma and chronic bronchitis. The compounds may be formulated in conventional manner as pharmaceutical compositions with physiologically acceptable carriers or excipients.The compounds may be prepared, for example by alkylation of an amine: ##STR2## where R.sup.3, R.sup.5 and R.sup.6 is hydrogen or a protecting group, followed by removal of any protecting group.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: September 7, 1993
    Assignee: Glaxo Group Ltd.
    Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor
  • Patent number: 5235103
    Abstract: A process for the preparation of phenylethanolaminotetralins of formula ##STR1## wherein X is hydrogen, a halogen, a trifluoromethyl or a lower alkyl group and R.sup.o is hydrogen or a methyl group substituted by a carboxy or a lower carbalkoxy group, which comprises treating a mandelic acid with a 2-amino-7-hydroxytetralin, optionally alkylating with a lower alkyl haloacetate and reducing the amido group of the mandelamide into a methyleneamino group. The mandelamides intermediates are novel.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: August 10, 1993
    Assignee: Sanofi
    Inventors: Robert Boigegrain, Roberto Cecchi, Sergio Boveri
  • Patent number: 5204468
    Abstract: This invention provides the single species (-)-(S)-4-(3,4-dihydroxyphenyl)-7, 8-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride hydrate, which is useful as a nephrovascular dilator.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: April 20, 1993
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Akihiro Tanaka, Takashi Fujikura, Ryuji Tsuzuki, Masaki Yokota, Takeyuki Yatsu
  • Patent number: 5198586
    Abstract: A process for the preparation of phenylethanolaminotetralins of formula ##STR1## wherein X is hydrogen, a halogen, a trifluoromethyl or a lower alkyl group and R.degree. is hydrogen or a methyl group substituted by a carboxy or a lower carbalkoxy group, which comprises treating a mandelic acid with a 2-amino-7-hydroxytetralin, optionally alkylating with a lower alkyl haloacetate and reducing the amido group of the mandelamide into a methyleneamino group. The mandelamides intermediates are novel.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: March 30, 1993
    Assignee: Sanofi
    Inventors: Robert Boigegrain, Roberto Cecchi, Sergio Boveri
  • Patent number: 5198587
    Abstract: Phenethylamine derivatives shown by the general formula ##STR1## wherein Ro represents a lower alkyl group; R.sub.1 represents a lower alkyl group or a lower alkoxy group; R.sub.2 represents hydrogen atom or a hydroxyl group; R.sub.3 and R.sub.4 each represents hydrogen atom or a lower alkyl group; R.sub.5 represents hydrogen atom or a lower alkoxy group; X represents oxygen atom or a methylene group; m is an integer of 1-3; and n is an integer of 0-2 and the acid addition salts thereof.These compounds exhibit a strong .alpha.-adrenergic blocking action and are useful as an antihypertensive agent.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: March 30, 1993
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kazuo Imai, Kunihiro Niigata, Takashi Fujikura, Shinichi Hashimoto, Toichi Takenaka, Kazuo Honda
  • Patent number: 5171753
    Abstract: Derivatives of 2-amino-1-phenylethanol were prepared from substituted amines and benzoin, stilbene oxide or styrene oxide to give compounds of Formula: ##STR1## where R is H or (un)substituted phenyl and C is a linking group or terminal group. The compounds of this invention can inhibit ulceration in in-vivo studies in rats.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: December 15, 1992
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Harry R. Munson, Jr., Robert F. Boswell
  • Patent number: 5130339
    Abstract: New phenylethanolaminomethyltetralins of formula (I) ##STR1## wherein E represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, phenyl, nitro, halogen, or trifluoromethyl,L represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkyoxy, phenyl, nitro, or halogen, orE and L taken together represent a group --CH.dbd.CH--CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, andG represents hydrogen, chloro, hydroxy or an --OG' group wherein G' represents a (C.sub.1 -C.sub.4 (alkyl group either unsubstituted or substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, carboxy, or (C.sub.3 -C.sub.7)cycloalkyl; a (C.sub.3 -C.sub.7)cycloalkyl group; or a (C.sub.2 -C.sub.4)alkanoyl group; and salts thereof, are described which showed to be active as intestinal motility modulating agents and intraocular hypertension lowering agents.
    Type: Grant
    Filed: December 28, 1990
    Date of Patent: July 14, 1992
    Assignee: Sanofi
    Inventors: Roberto Cecchi, Umberto Guzzi
  • Patent number: 5126375
    Abstract: Phenethanolamine derivatives are disclosed of formula ##STR1## wherein m is 2 to 8; n is 1 to 7 provided that m+n is 4 to 12;Ar is phenyl or phenyl substituted by one or two halogen atoms, alkyl or alkoxy groups or by an alkylenedioxy group;R.sup.1 and R.sup.2 are hydrogen or alkyl provided that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 4; and the physiologically acceptable salts and solvates thereof.The compounds have a selective stimulant action at .beta..sub.2 -adrenoreceptors and may be used inter alia in the treatment of diseases associated with reversible airways obstructions such as asthma and chronic bronchitis. The compounds may be formulated in conventional manner as pharmaceutical compositions with physiologically acceptable carriers or excipients.The compounds may be prepared, for example by alkylation of an amine: ##STR2## where R.sup.3, R.sup.5 and R.sup.6 is hydrogen or a protecting group, followed by removal of any protecting group.
    Type: Grant
    Filed: November 29, 1990
    Date of Patent: June 30, 1992
    Assignee: Glaxo Group Ltd.
    Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor
  • Patent number: 5124334
    Abstract: The invention relates to benylalcohol phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylalcohol phospholipase A.sub.2 inhibitor.
    Type: Grant
    Filed: July 28, 1989
    Date of Patent: June 23, 1992
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventor: Wendell W. Wilkerson
  • Patent number: 5105017
    Abstract: This invention provides novel benzene derivatives which are leukotriene antagonists, formulations of those derivatives, intermediates for preparing the derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: April 14, 1992
    Assignee: Eli Lilly and Company
    Inventor: Robert D. Dillard
  • Patent number: 5066678
    Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts and solvates thereof; wherein;R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-3 -alkyl group with the proviso that the sum total of carbon atom in R.sup.1 and R.sup.2 is not more than 4;X represents a direct bond or a C.sub.1-7 alkylene, C.sub.2-7 alkenylene or C.sub.2-7 alkynylene group and Y represents a direct bond or a C.sub.1-6 alkylene C.sub.2-6 alkenylene or C.sub.2-6 alknylene group with the proviso that the sum total of carbon atoms in X and Y is not more than 10;W represents a group ##STR2## wherein Z represents a group R.sup.3 (CH.sub.2).sub.q where q is 0, 1 or 2 and R.sup.3 is a group R.sup.4 CONH--, R.sup.4 NHCONH--, R.sup.4 R.sup.5 NSO.sub.2 NH--, R.sup.6 SO.sub.2 NH-- or --OH;R.sup.4 and R.sup.5 each represent a hydrogen atom or a C.sub.1-3 alkyl group;R.sup.6 represents a C.sub.1-3 alkyl group;R.sup.7 represents a chlorine atom or the group --CF.sub.
    Type: Grant
    Filed: April 23, 1990
    Date of Patent: November 19, 1991
    Assignee: Glaxo Group Limited
    Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor, Ian B. Campbell, Charles Willbe, William L. Mitchell, Stephen Swanson, Brian D. Judkins
  • Patent number: 5047433
    Abstract: N-alkyl derivatives of 2-amino-6,7-dimethoxy tetraline having general formula (I) ##STR1## wherein R is selected from hydrogen, ethyl, n-propyl and methyl cyclopropyl;R.sub.1 is selected from hydrogen, hydroxy and --OR.sub.3 wherein R.sub.3 is selected from methyl, ethyl and n-propyl; andR.sub.2 is selected from hydrogen, methyl, hydroxy, trifluoromethyl, fluoro and methoxy,are endowed with potent antihypertensive activity.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: September 10, 1991
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Mauro Marzi, Maria O. Tinti, Romano Di Fabio, Domenico Misiti
  • Patent number: 4952729
    Abstract: There is disclosed an improved process for preparing albuterol which comprises reacting a 5-(haloacetyl)-2-hydroxybenzaldehyde with 1,1-dimethylethanamine in an organic solvent and in an inert atmosphere to form 5-[[(1,1-dimethylethyl)amino]acetyl]-2-hydroxybenzaldehyde and reducing the carbonyl functions to the corresponding hydroxy groups to form albuterol.
    Type: Grant
    Filed: November 3, 1989
    Date of Patent: August 28, 1990
    Assignee: Schering-Plough Corp.
    Inventors: Esther Babad, Nicholas Carruthers, Martin Steinman
  • Patent number: 4876261
    Abstract: A compound of the formula (I) or its salt and a process for producing the compounds; The compounds have the effect to dilate neophrovascular tracts; ##STR1## wherein ##STR2## represents the formula ##STR3## (wherein R.sup.4 is a hydrogen atom or lower alkylsulfonyl); R.sup.1 is hydrogen, lower alkyl, hydroxyl, halogen, amino, or lower acylamino;R.sup.2 is hydrogen, lower alkyl, hydroxyl, amino, or lower alkylsulfonylamino;R.sup.3 is hydrogen, lower, alkyl or hydroxyl;R is hydrogen or halogen;with the proviso that when R.sup.1 is hydroxyl, there is no case that all of R.sup.2, R.sup.3 and R are hydrogens, and further with the proviso that when R is hydrogen, A excludes ##STR4## or a salt thereof.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: October 24, 1989
    Inventors: Akihiro Tanaka, Takashi Fujikura, Ryuji Tsuzuki, Masaki Yokota, Takeyuki Yatsu
  • Patent number: 4754047
    Abstract: There is provided a method for enhancing the growth rate of meat-producing animals and/or improving the efficiency of feed utilization thereby, which involves, orally or parenterally, administering to said animals a growth-enhancing amount of a phenylethanolamine compound or the acid addition salt thereof.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: June 28, 1988
    Assignee: American Cyanamid Company
    Inventors: Jane A. Kiernan, Pamela K. Baker
  • Patent number: 4749792
    Abstract: Analgesic activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, alkyl, carboxyalkyl, halosubstituted alkyl, hydroxyalkyl, aminoalkyl, mercaptoalkyl, alkylthioalkyl, (cycloalkyl)alkyl, (heteroaryl)alkyl, arylalkyl, carbamoylalkyl, guanidinylalkyl, or heteroaryl, and R.sub.3 is hydroxymethylene or carbonyl.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: June 7, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Sesha I. Natarajan, Eric M. Gordon
  • Patent number: 4695589
    Abstract: Alpha-(aminoalkyl)-4-hydroxy-3-(alkylthio)benzenemethanols useful as intermediates and as antihypertensive agents are prepared by reduction of the corresponding aminoalkyl 4-hydroxy-3-(alkylthio)phenyl ketones.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: September 22, 1987
    Assignee: Sterling Drug Inc.
    Inventor: Richard E. Philion
  • Patent number: RE43844
    Abstract: A process for making optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.
    Type: Grant
    Filed: December 10, 2001
    Date of Patent: December 4, 2012
    Assignee: Cipla Limited
    Inventors: Yusuf Khwaja Hamied, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao
  • Patent number: RE43984
    Abstract: A process for making optically Optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form is obtained by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said a salbutamol precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R) or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.
    Type: Grant
    Filed: December 10, 2001
    Date of Patent: February 5, 2013
    Assignee: Cipla Limited
    Inventors: Yusuf Khwaja Hamied, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao