Patents Represented by Attorney R. Hain Swope
  • Patent number: 5240939
    Abstract: Muscle relaxant nitrogen bridge tetrahydroisoquinolines are disclosed. The novel compounds are represented by the formula ##STR1## wherein A is ##STR2## M represents --(CH.sub.2).sub.n --Z--(CH.sub.2).sub.n or ##STR3## R is a C.sub.1-3 alkoxy group, or adjacent Rs are a methylenedioxy group, R.sub.1 is lower alkyl; n is 1-6;m is 2 or 3; p is 1-3; Z is --N.sup.+ (R.sub.2 R.sub.3)--, --N(R.sub.4)--, ##STR4## and --N[(CH.sub.2).sub.n --A--R.sub.5 ]--; R.sub.2 and R.sub.3 are independently lower alkyl groups wherein a carbon atom within the chain may be replaced by a heteroatom, lower cycloalkyl, lower cycloalkyl lower alkyl, aryl, aryl lower alkyl, a 4- to 6-member heteroring or may be combined with the nitrogen to form a heteroring; R.sub.4 is a straight- or branched- chain C.sub.1-10 alkyl wherein a carbon atom within the chain may be replaced by a heteroatom, lower cycloalkyl, lower cycloalkyl lower alkyl, aryl, or a heteroring, which groups may be substituted or unsubstituted; or ##STR5## R.sub.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: August 31, 1993
    Assignee: Anaquest, Inc.
    Inventor: Donald M. Demko
  • Patent number: 5229511
    Abstract: This invention pertains to novel 3-substituted-aminomethyl-3-substituted-oxy-17a-methyl-17a-lower-alkyl-17a -aza-D-homo-5-alpha-androstane compounds useful as muscle relaxants, methods for preparing such compounds, and method for administering muscle relaxation, wherein the novel compounds are represented the general formula: ##STR1## including optical active isomeric forms, and pharmaceutically acceptable acid addition salts thereof, wherein:R is a selected from the group consisting of hydrogen, lower-alkyl, lower-alkyl carbonyl, and di(lower-alkyl)amino carbonyl:R.sup.1 is selected from the group consisting of: di(lower-alkyl)substituted amino; lower-cycloalkyl lower-alkyl, lower-alkyl substituted amino;, -piperidinyl; 1-pyrrolidinyl; 1-hexamethyleneimino; 4-morpholinyl; 1-piperazinyl, 1-(4-methylpiperazinyl), tri(lower-alkyl)substituted amino, 1-(1-methylpiperidinyl); 1-(1-methylpyrrolidinyl); and 1-(4,4-dimethylpiperazinyl), each lower-alkyl group having from 1 to 6 carbon atoms;R.sub.
    Type: Grant
    Filed: June 8, 1992
    Date of Patent: July 20, 1993
    Assignee: Anaquest, Inc.
    Inventor: Roger S. Chen
  • Patent number: 5205914
    Abstract: An improved preparation of desflurane, 1,2,2,2-tetrafluoroethyl difluoromethyl ether utilizing hexafluoropropene epoxide as a starting material. Hexafluoropropene epoxide is advantageous in that it is relatively inexpensive and is environmentally acceptable.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: April 27, 1993
    Assignee: Anaquest, Inc.
    Inventors: Leonid A. Rozov, Chialang Huang, Gerald G. Vernice
  • Patent number: 5190924
    Abstract: Peptide amide and amide dimer muscle relaxants represented by the formulae: ##STR1## wherein: R is lower alkyl; R.sub.1 and R.sub.2 independently selected from the group consisting of hydrogen, lower alkyl, allyl, propargyl, aryl lower alkyl and cyclo-lower alkyl lower alkyl, or R plus one or both of R.sub.1 and R.sub.2, together with the nitrogen to which they are attached, form a heterocyclic ring having 5 to 7 member atoms; AA are independently selected from certain amino acids moieties; n is 2 to 4; x is independently 0 or 1; y is independently 1 or 2; z is 2 to 12; and An.sup.- is a pharmaceutically acceptable anion.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: March 2, 1993
    Assignee: BOC Health Care, Inc.
    Inventors: Zenon D. Konteatis, David C. Palmer
  • Patent number: 5155149
    Abstract: The present invention is directed to silicone polyurethane copolymers containing phosphorescent dye compounds wherein the copolymers are represented by the formula: ##STR1## wherein n is an integer ranging from 1 to about 30, and y, z, and w are integers ranging from 0 to about 40, wherein one of y, z, and w is at least one; and A is a diamide, B is a silicone block copolymer, D is a chain extender, and E is a phosphorescent porphyrin-type compound.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: October 13, 1992
    Assignee: BOC Health Care, Inc.
    Inventors: Beauford W. Atwater, Suzanne Klima
  • Patent number: 5145967
    Abstract: The present invention is directed to a method for preparing a 4-alkoxyalkyl-4-phenylaminopiperidine compound which comprises the steps of (a) reacting an N-substituted-4-piperidone compound with an aniline compound to form a Schiff base compound, (b) reacting the Schiff base compound with an anionic reagent having an anion stabilizing group to form an amine compound, and (c) reducing the amine compound in step (b) with a reducing agent to displace the anion stabilizing group.The anionic reagent in step (b) above has the general formula:X--CYM--Zwherein X is an anion stabilizing group, Y is hydrogen or lower-alkyl, Z is lower-alkoxy or phenylmethoxy, M is an alkali or alkaline earth metal, and C is a carbon atom.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: September 8, 1992
    Assignee: Anaquest, Inc.
    Inventors: Bor-Sheng Lin, H. Kenneth Spencer, Joseph W. Scheblein
  • Patent number: 5140022
    Abstract: This invention pertains to novel 3-substituted-aminomethyl-3-substituted-oxy-17a-methyl-17a-lower-alkyl-17a -aza-D-homo-5-alpha-androstane compounds useful as muscle relaxants, methods for preparing such compounds, and methods for administering muscle relaxation, wherein the novel compounds are represented the general Formula: ##STR1## including optically active isomeric forms, and pharmaceutically acceptable acid addition salts thereof, wherein:R is selected from the group consisting of hydrogen, lower-alkyl, lower-alkyl carbonyl, and di(lower-alkyl)amino carbonyl;R.sub.1 is selected from the group consisting of: di(lower-alkyl)substituted amino; lower-cycloalkyl lower-alkyl, lower-alkyl substituted amino;, 1-piperidinyl; 1-pyrrolidinyl; 1-hexamethyleneimino; 4-morpholinyl; 1-piperazinyl, 1-(4-methylpiperazinyl), tri(lower-alkyl)substituted amino, 1-(1-methylpiperidinyl); 1-(1-methylpyrrolidinyl); and 1-(4,4-dimethylpiperazinyl), each lower-alkyl group having from 1 to 6 carbon atoms;R.sub.
    Type: Grant
    Filed: March 21, 1991
    Date of Patent: August 18, 1992
    Assignee: Anaquest, Inc.
    Inventor: Roger S. Chen
  • Patent number: 5100903
    Abstract: This invention pertains to novel N-aryl-N-[N-substituted 3-alkoxy-4-piperidinyl]amides useful as analgesics, and methods of administering analgesia, which comprises the systemic administration to mammals of such compounds, and pharmaceutical compositions containing such compounds, wherein the novel compounds have the general formula: ##STR1## including optically active isomeric forms, cis/trans isomeric forms and the pharmaceutically acceptable acid addition salts thereof, wherein:R is an aryl group selected from the group consisting of phenyl and substituted phenyl, wherein the substituents on the phenyl group are independently selected from the group consisting of halogen, lower-alkyl, lower-alkoxy, and combinations thereof;R.sub.1 is an alkyl group selected from the group consisting of lower-alkyl, lower-alkenyl, and lower-alkoxy lower-alkyl, each alkyl group having from 1 to 6 carbon atoms;R.sub.
    Type: Grant
    Filed: November 21, 1990
    Date of Patent: March 31, 1992
    Assignee: Anaquest, Inc.
    Inventors: Nhora L. Lalinde, John Moliterni, H. Kenneth Spencer
  • Patent number: 5053411
    Abstract: This invention pertains to novel substituted N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides useful as analgesics, and methods of administering analgesia, which comprises the systemic administration to mammals of such compounds, and pharmaceutical compositions containing such compounds, wherein the novel compounds have the general formula: ##STR1## including optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in the disclosure.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: October 1, 1991
    Assignee: Anaquest, Inc.
    Inventors: Jerome R. Bagley, Nhora L. Lalinde, Bao-Shan Huang, H. Kenneth Spencer
  • Patent number: 5026924
    Abstract: A process is provided for the low temperature preparation of CF.sub.3 CHFOCHF.sub.2 which comprises reacting CF.sub.3 CHClOCHF.sub.2 with hydrogen fluoride in the presence of an antimony pentachloride catalyst or mixture of antimony pentachloride and antimony trichloride.
    Type: Grant
    Filed: January 4, 1990
    Date of Patent: June 25, 1991
    Assignee: Anaquest, Inc.
    Inventor: Charles F. Cicco
  • Patent number: 5015781
    Abstract: The present invention is directed to a method of preparing a compound 2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane by reacting 2-(difluoromethoxy)-1,1,1-trifluoro-2-chloroethane with bromine trifluoride. This reaction product is useful for inducing and maintaining anesthesia in warm blooded animals.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: May 14, 1991
    Assignee: BOC, Inc.
    Inventors: Mark L. Robin, Donald F. Halpern
  • Patent number: 5013742
    Abstract: Compounds are disclosed of the formula ##STR1## where R.sup.2 is unsubstituted or substituted phenyl, R.sup.3 is lower alkyl, lower cycloalkyl or lower alkoxy lower alkyl, and L is selected from a wide variety of groups. This new class of compounds exhibit improved analgesic and anesthetic properties.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: May 7, 1991
    Assignee: BOC, Inc.
    Inventors: Linas V. Kudzma, H. Kenneth Spencer, Sherry A. Severnak
  • Patent number: 4996371
    Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine group in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and alkoxy-substituted halogenated aliphatic groups, wherein the method comprises the steps of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: February 26, 1991
    Assignee: BOC, Inc.
    Inventors: Donald F. Halpern, Mark L. Robin
  • Patent number: 4994471
    Abstract: This invention pertains to novel N-aryl-N-[N-substituted 3-alkoxy-4-piperidinyl]amides useful as analgesics, and methods of administering analgesia, which comprises the systemic administration to mammals of such compounds, and pharmaceutical compositions containing such compounds, wherein the novel compounds have the general formula: ##STR1## including optically active isomeric forms, cis/trans isomeric forms and the pharmaceutically acceptable acid addition salts therof, wherein:R is an aryl group selected from the group consisting of phenyl and substituted phenyl, wherein the substituents on the phenyl group are independently selected from the group consisting of halogen, lower-alkyl, lower-alkoxy, and combinations thereof;R.sub.1 is an alkyl group selected from the group consisting of lower-alkyl, lower-alkenyl, and lower-alkoxy lower-alkyl, each alkyl group having from 1 to 6 carbon atoms;R.sub.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: February 19, 1991
    Assignee: BOC, Inc.
    Inventors: Nhora L. Lalinde, John Moliterni, H. Kenneth Spencer
  • Patent number: 4972677
    Abstract: Liquid carbon dioxide substantially free of particles is prepared by evaporating liquid carbon dioxide, passing the resulting gaseous carbon dioxide through a suitable filter to remove particles therefrom and cooling the particle-free gas to reliquefy it.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: November 27, 1990
    Assignee: The BOC Group, Inc.
    Inventors: Kozo Moriya, Tadashi Ookatsu
  • Patent number: 4972040
    Abstract: A process for the preparation of a compound having the formula CF.sub.3 CHFOCH.sub.3 comprising reacting a fluorinating agent with the reaction product of CF.sub.3 CH(OH)OCH.sub.3 and p-toluene sulfonyl chloride and an improved method for the preparation of CHF.sub.2 OCHFCF.sub.3 through the use of such compounds.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: November 20, 1990
    Assignee: BOC, Inc.
    Inventors: Mark L. Robin, Donald F. Halpern
  • Patent number: 4957929
    Abstract: Compounds are disclosed of the formula ##STR1## where R.sup.2 is unsubstituted or substituted phenyl, R.sup.3 is lower alkyl, lower cycloalkyl or lower alkoxy lower alkyl, and L is selected from a wide variety of groups. This new class of compounds exhibit improved analgesic and anesthetic properties.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: September 18, 1990
    Assignee: BOC, Inc.
    Inventors: Linas V. Kudzma, H. Kenneth Spencer, Sherry A. Severnak
  • Patent number: 4954506
    Abstract: This invention pertains to novel substituted N-heterocyclic-N-(4-piperidinyl)amides useful as analgesics and antagonists of opioids, wherein the compounds have the general formula: ##STR1## including optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein:R is a substituted or unsubstituted unsaturated heterocyclic ring system having 5 to 6 cyclic member atoms containing at least one nitrogen atom, and is preferably selected from the group consisting of pyridinyl, pyrimidinyl, and pyrazinyl;R.sub.1 is selected from the group consisting of unsubstituted or substituted heterocyclic ring systems having 5 cyclic member atoms, lower cyclic alkyl ring systems, lower-alkyl and lower-alkoxy lower-alkyl, and is preferably selected from the group consisting of furanyl lower-alkyl, thienyl lower-alkyl, pyrrolyl lower-alkyl, lower-alkyl, lower-cycloalkyl, and lower-alkoxy lower-alkyl of 2 to 6 carbons;R.sub.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: September 4, 1990
    Assignee: BOC, Inc.
    Inventors: Jerome R. Bagley, H. Kenneth Spencer
  • Patent number: RE33495
    Abstract: The present invention is directed to an improved stereoselective tandem substitution and reduction of an imine precursor to the cis form of .[.3-substituted-4-(phenylamino)piperidine.]. .Iadd.3-substituted-4-anilino piperidine .Iaddend.compounds or their substituted derivatives.
    Type: Grant
    Filed: September 27, 1989
    Date of Patent: December 18, 1990
    Assignee: BOC, Inc.
    Inventors: Linas V. Kudzma, H. Kenneth Spencer, Sherry A. Savernak
  • Patent number: RE34201
    Abstract: This invention pertains to novel substituted N/aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides useful as analgesics, and methods of administering analgesia, which comprises the systemic administration to mammals of such compounds, and pharmaceutical compositions containing such compounds, wherein the novel compounds have the general formula: ##STR1## including optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in the disclosure.
    Type: Grant
    Filed: April 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Anaquest, Inc.
    Inventors: Jerome R. Bagley, Nhora L. Lalinde, Bao-Shan Huang, H. Kenneth Spencer