Patents Represented by Attorney Charles M. Caruso

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  • Trifluoromethylbenzyl containing quaternary salts
    Patent number: 5093498
    Abstract: A process is disclosed for obtaining manipulated proportions of the (+) and (-) enantiomers of [(6,7-dichloro-2,3-dihydro-2-methyl-1-oxo-2-phenyl-1H-inden-5-yl)oxy]aceti c acid by asymmetric chiral phase transfer catalysis.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: March 3, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Ulf H. Dolling, Seemon H. Pines, Edward J. J. Grabowski
  • Trialkylsilyl trifluoromethanesulfonate mediated .alpha.-methylenic carbon functionalization of 4-AZA-5.alpha.-androstan-3-one steroids
    Patent number: 5091534
    Abstract: A novel single-pot trialkylsilyl trifluoromethanesulfonate (R.sub.3 Si--OTf) mediated process produces derivatives of 4-aza 3-keto steroids at the .alpha.-methylenic carbon through electrophilic substitution. These derivatives are useful in the preparation, through elimination of the substituent on the .alpha.-methylene carbon, of .DELTA.-1 olefin 4-aza 3-keto steroids which are potent inhibitors of 5-.alpha. reductase.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: February 25, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Anthony O. P. King, Sandor Karady, Kevin Anderson, Alan W. Douglas, Newton L. Abramson, Richard F. Shuman
  • N-monosubstituted adamantyl/norbornanyl 17.beta.-carbamides of 3-carboxy-androst-3,5-dienes as testosterone 5.alpha.-reductase inhibitors
    Patent number: 5091380
    Abstract: N-monosubstituted adamantyl/norbornanyl 17.beta.-carbamides of 3-carboxy-androst-3,5-dienes as testosterone 5.alpha.-reductase inhibitors of the formula: ##STR1## wherein R is a hydrocarbon radical selected from substituted or unsubstituted 1- or 2-adamantyl or 1-, 2- or 7-norbornanyl and pharmaceutically acceptable salts or esters thereof. Also described is a pharmaceutical formulation. The above compounds are active as testosterone 5.alpha.-reductase inhibitors and thus are useful topically for treatment of acne, seborrhea, female hirsutism, and systemically in treatment of benign prostatic hypertrophy.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: February 25, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Gary H. Rasmusson, Richard L. Tolman, Gool F. Patel
  • Spirocyclic oxytocin antagonists
    Patent number: 5091387
    Abstract: Disclosed are spirocyclic compounds of the formula: ##STR1## The compounds of formula I are oxytocin antagonists useful in the treatment of preterm labor and dysmenorrhea, and for the stoppage of labor preporatory to Caesarian delivery. Also disclosed are pharmaceutical compositions containing these compounds as well as methods for preparing the compounds.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: February 25, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Ben E. Evans, Douglas J. Pettibone, Roger M. Friedinger
  • Process for synthesis of FK-506 intermediates
    Patent number: 5087703
    Abstract: A process is described for the synthesis of diastereomeric 2-methyl-4-hydroxy-5-protected-hydroxy-hept-6-en-prolinolamides, which are useful as intermediates in the synthesis of the C.sub.10 -C.sub.18 chain of the macrolide structure for the immunosuppressant FK-506. These compounds are also useful as intermediates for preparing lactone ultraviolet radiation absorbers.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: February 11, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Ralph P. Volante, David Askin, Ichiro Shinkai, Kenneth M. Ryan
  • Humoral hypercalcemic factor antagonists modified at position 13 by biotin
    Patent number: 5087561
    Abstract: The present invention relates to the use of peptide analogues as inhibitors of their respective naturally occurring peptides. The structure of the peptide hormone analogues is exemplified by human humoral hypercalcemic factor (hHCF), wherein Lys.sup.13 or Lys.sup.11 is modified on the epsilon-amino group by biotin so as to produce HCF analogues which can inhibit the action of HCF.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: February 11, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Michael Rosenblatt, Michael Chorev, Eliahu Roubini, Ruth F. Nutt, Le T. Duong
  • Humoral hypercalcemic factor antagonists with modification at position 13 . . .
    Patent number: 5087562
    Abstract: The present invention relates to the use of peptide analogues as inhibitors of their respective naturally occurring peptides. The structure of the peptide hormone analogues is exemplified by human humoral hypercalcemic factor (hHCF), wherein Lys.sup.13 is modified so as to produce HCF analogues which can inhibit the action of HCF.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: February 11, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Michael Rosenblatt, Eliahu Roubini, Michael Chorev, Ruth F. Nutt
  • Dehydrogenation process
    Patent number: 5084574
    Abstract: A process for dehydrogenating a compound of the formula ##STR1## which comprises reacting the compound with a silylating agent in the presence of a quinone to introduce a .DELTA..sup.1 double bond.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: January 28, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Apurba Bhattacharya, Alan W. Douglas, Edward J. Grabowski, Ulf H. Dolling
  • Child resistant unit dose package
    Patent number: 5082114
    Abstract: A child resistant unit dose package for medications comprises a container member having concealed locking means, a plurality of cavities along its longitudinal axis for holding medication, each cavity closed with a peel-off seal, and a cover for the container member that requires two operations to open.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: January 21, 1992
    Assignee: Merck & Co., Inc.
    Inventor: Leonid Bunin
  • Film-forming size composition
    Patent number: 5079348
    Abstract: A film forming composition useful as a paper size is described which includes 1-20 parts, preferably 2-15 parts, by weight of a gum selected from the group consisting of xanthan gum, rhamsan gum, welan gum and mixtures thereof; 3-20 parts, preferably 5-17 parts, by weight of a water soluble alginate; and 60-100 parts, preferably 70-90 parts, by weight of starch, polyvinyl alcohol or carboxymethylcellulose, with the gum:alginate ratio being not greater than 1:1, preferably not greater than 1:2. The balance of the composition will primarily be water. Additives such as sodium hexametaphosphate may also be present.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: January 7, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Kenneth Clare, Philip E. Winston, Jr., Harold D. Dial, Theresa M. Ortega
  • Intermediates in the synthesis of 17.beta.-acyl-3-carboxy-androsta-3,5-dienes
    Patent number: 5075450
    Abstract: New intermediates in the synthesis of 17.beta.-acyl-3-carboxy-androsta-3,5-dienes, of the formula: ##STR1## wherein R.sup.2 is 2-thiopyridyl, andR.sup.3 is C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4, or trifluoromethylsulfonyloxy. The above compounds are useful intermediates in producing testosterone 5.alpha.-reductase inhibitors which are useful topically for treatment of acne, seborrhea, female hirsutism, and systemically in treatment of benign prostatic hypertrophy.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: December 24, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Gary H. Rasmusson, Richard L. Tolman, Gool F. Patel
  • Novel substituted pyrazine, formulations thereof and use in medicine
    Patent number: 5073557
    Abstract: The compound (R)-3-[2-(6-chloropyrazin)yl]-1-azabicyclo[2.2.2]octane and its salts behave as M.sub.1, M.sub.3 muscarinic agonists and are useful in the treatment of neurological and mental disorders, preferably in a pharmaceutical formulation comprising the active compound in association with a pharmaceutically acceptable carrier. The compound can be prepared by via methods analogous to those known in the art and a chiral acid resolution.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: December 17, 1991
    Assignee: Merck Sharp & Dohme Limited
    Inventors: Raymond Baker, Leslie J. Street, John Saunders
  • Thermally re-arranged FK-506 derivatives having immunosuppressant activity
    Patent number: 5068323
    Abstract: Ring-expanded macrolides related to FK-506 have immunosuppressive activity.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: November 26, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Matthew J. Wyvratt, Jr., Thomas R. Beattie, Hyun Ok, Byron H. Arison, Michael H. Fisher
  • Process for making 17-beta alkanoyl 3-oxo-4-aza-5-.alpha.-androst-1-enes
    Patent number: 5061803
    Abstract: Disclosed is a new process for making 17-beta branched alkanoyl-3-oxo-4-aza-5-.alpha.-androst-1-enes, agents for treating benign prostatic hypertrophy (BPH), by reacting methyl 3-oxo-4-aza-5-.alpha.-androst-1-ene-17-beta carboxylate with isobutylmagnesium bromide in the novel presence of the hexamethyldisilazane (HMDS). Use of the HMDS results in higher yield and less by-products as opposed to the standard Grignard reaction in the absence of HMDS.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: October 29, 1991
    Assignee: Merck & Co., Inc.
    Inventor: John M. Williams
  • Fibrinogen receptor antagonists
    Patent number: 5061693
    Abstract: A fibrinogen receptor antagonist compound of the structure:A--B--C--Gly--Asp--D--E (I)wherein A, B, C, D and E are preferably defined as follows:A is L-asparagine, D-asparagine or acylated asparagineB is an L-or D-isomer of proline, thioproline, .beta.,.beta.-dimethylthioproline, or N-methylalanine;C is arginine;D is phenylalanine, tryptophan .alpha.-naphthylalanine, .beta.-napthlalanine, arginine or lysine; andE is OH.
    Type: Grant
    Filed: July 28, 1989
    Date of Patent: October 29, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Ruth F. Nutt, Stephen F. Brady, Daniel F. Veber
  • Intermediate for making 3-oxo-4-aza-androst-1-ene 17.beta.-ketones
    Patent number: 5061801
    Abstract: Described is a new intermediate and new process for preparing 3-oxo-4-aza-androst-1-ene 17.beta.-ketones. The process involves converting the corresponding 17.beta.-alkyl carboxylate to the N-methoxy-N-methyl carboxamide and reacting this with an appropriate Grignard reagent to form the desired ketone. The reaction can be conducted in "one pot", thus eliminating isolation of intermediates and avoiding the use of less stable intermediates, e.g., acid chlorides, acyl imidazolides and the like. The intermediate has the formula: ##STR1## wherein R.sup.1 is hydrogen.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: October 29, 1991
    Assignee: Merck & Co., Inc.
    Inventors: John M. Williams, Ulf H. Dolling
  • 17.beta.-aminobenzoyl-4-aza-5.alpha.-androst-1-en-3-ones as benign prostatic hypertrophy agents
    Patent number: 5061802
    Abstract: New 17.beta.-aminobenzoyl-4-aza-5.alpha.-androst-1-en-3-ones as benign prostatic hypertrophy agents of the formula: ##STR1## wherein R is selected from hydrogen, methyl and ethyl andR.sup.2 is phenyl substituted with --N(R.sup.3).sub.2, which can be protected, where R.sub.3 is independently H or C.sub.1 -C.sub.4 alkyl, wherein the phenyl ring can also be further substituted by C.sub.1 -C.sub.4 alkyl, wherein the dotted line can represent a double bond, and pharmaceutically acceptable salts thereof, and a pharmaceutical formulation thereof. The above compounds are active as benign prostatic hypertrophy therapy agents and are useful topically for the treatment of acne, seborrhea, female hirsutism, and particularly effective systemically in the treatment of benign prostatic hypertrophy.
    Type: Grant
    Filed: June 20, 1990
    Date of Patent: October 29, 1991
    Assignee: Merck & Co. Inc.
    Inventors: Nathan G. Steinberg, Gary H. Rasmusson, Thomas N. Salzmann
  • Immunoregulants, immunosuppressants, process to make ring expanded macrolide related to FK-506/FK-520
    Patent number: 5057608
    Abstract: Ring-expanded, immunosuppressive macrolides, are produced by heating and rearranging FK-506 and related compounds.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: October 15, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Matthew J. Wyvratt, Jr., Thomas R. Beattie, Hyun O. Ok, Byron H. Arison, Michael H. Fisher
  • Synthesis of inositol phosphates
    Patent number: 5055597
    Abstract: This invention provides the 4-mono-anion of myo-inositol orthoformate, and describes a process for preparing this anion as well as the use of this anion in the preparation of a variety of mono- and poly-phosphate derivatives of myo-inositol.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: October 8, 1991
    Assignee: Merck Sharp & Dohme Ltd.
    Inventor: David C. Billington
  • 17.beta.-acyl-4-aza-5.alpha.-androst-1-ene-3-ones as 5.alpha.-reductase inhibitors
    Patent number: 5049562
    Abstract: 17.beta.-Acyl-4-aza-5.alpha.-androst-1-ene-3-ones of the formula ##STR1## wherein R is selected from hydrogen, methyl and ethyl andR.sup.2 is monocyclic aryl optionally containing 1 or more lower alkyl substituents of from 1-2 carbon atoms and/or 1 or more halo (Cl or Br) substituents;and R', R" and R'" are each selected from hydrogen and methyl and pharmaceutical formulation of the above compounds are active as testosterone 5.alpha.-reductase inhibitors and thus are useful for treatment of acne, seborrhea, female hirsutism, androgenic alopecia, prostatic carcinoma and benign prostatic hypertrophy.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: September 17, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Gary H. Rasmusson, Glenn F. Reynolds