Patents Represented by Attorney Bruce Stein

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  • Processes for purification of 2,4-di(1-pyrrolidinyl)-6-chloropyrimidine
    Patent number: 5225555
    Abstract: The present invention involves two processes for the purification of a mixture of 2,4-di(1-pyrrolidinyl)-6-chloropyrimidine (III) ##STR1## and 4,6-di(1-pyrrolidinyl)-2-chloropyrimidine (IV) ##STR2## to where <1.0% of 4,6-di(1-pyrrolidinyl)-2-chloropyrimidine (IV) is present. In addition also disclosed is a process which not only purifies 2,4-di(1-pyrrolidinyl)-6-chloropyrimidine (III) but produces the commercially important 2,4-di(1-pyrrolidinyl)-6-(1-piperazinyl)pyrimidine (IX) directly.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: July 6, 1993
    Assignee: The Upjohn Company
    Inventors: Bruce A. Pearlman, Amphlett G. Padilla
  • Antibacterial 3-(fused-ring substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones
    Patent number: 5225565
    Abstract: The present invention relates to 3-(fused-ring substituted)phenyl-5.beta.-amidomethyloxazolidin-2-one (XXI) ##STR1## where either R.sub.2 and R.sub.4 is --H and the other of R.sub.2 and R.sub.4 taken together with R.sub.3 is --(CH.sub.2).sub.n5 --CH.dbd.CH--(CH.sub.2).sub.n6 --. Also claimed are various alkyl substituted fused ring substituted alkanones, preferred is 3-(1'-oxo-2'.alpha./.beta.-methyl-5'-indanyl)-5.beta.-(acetamidomethyl)oxa zolidin-2-one. These compounds are useful as antibacterial agents.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: July 6, 1993
    Assignee: The Upjohn Company
    Inventor: Steven J. Brickner
  • Geminal bisphosphonic acids and derivatives as anti-arthritic agents
    Patent number: 5220021
    Abstract: Unsaturated geminal phosphonates (III) ##STR1## either as the esters, free acids or salts are useful in the treatment of arthritis.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: June 15, 1993
    Assignee: The Upjohn Company
    Inventors: Colin J. Dunn, Richard A. Nugen
  • Substituted 3(5'indazolyl) oxazolidin-2-ones
    Patent number: 5182403
    Abstract: The present invention relates to 3 indazol substituted 5 Beta amidomethyloxazolidin-2ones, useful as antibacterial agents and to intermediates for their production.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: January 26, 1993
    Assignee: The Upjohn Company
    Inventor: Steven J. Brickner
  • Pharmaceutically active pyrimidinylpiperazinylsterioids
    Patent number: 5175281
    Abstract: Disclosed are .DELTA..sup.9(11) -steroids (VI) and amino substituted steroids (XI) which contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain, more particularly amino steroids (Ia and Ib), aromatic steroids (II), .DELTA..sup.16 -steroids (IIIa and IIIb), reduced A-ring steroids (IV), .DELTA..sup.17(20) -steroids (Va and Vb) and .DELTA..sup.9(11) -steroids (VI) which are useful as pharmaceutical agents for treating a number of conditions.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: December 29, 1992
    Assignee: The Upjohn Company
    Inventors: John M. McCall, Donald E. Ayer, E. Jonathan Jacobsen, Frederick J. VanDoornik, John R. Palmer, Harold A. Karnes
  • 5'Indolinyl-5.beta.-amidomethyloxazolidin-2-ones
    Patent number: 5164510
    Abstract: The present invention relates to 5'-indolinyloxazolidin-2-ones (XI) ##STR1## 3-(fused-ring) substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (XXI) ##STR2## and 3-(nitrogen substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (LV) which are useful as antibacterial agents and the intermediates (VI), (VII) and (VIII) useful for their production.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: November 17, 1992
    Assignee: The Upjohn Company
    Inventor: Steven J. Brickner
  • Pharmaceutically active amines
    Patent number: 5120843
    Abstract: The aromatic amines (I), alkyl amines (II), bicyclic amines (III). ##STR1## cycloalkyl amines (IV), aromatic bicyclic amines (V), hydroquinone amines (VI), quinone amines (VII), amino-ethers (VIII) and bicyclic amino ethers (IX) are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc. Also disclosed is a method of treatment using the 3,4-dihydrobenzopyrans (XI).
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: June 9, 1992
    Assignee: Upjohn
    Inventors: John M. McCall, Donald E. Ayer, E. Jon Jacobsen, Frederick J. VanDoornik, John R. Palmer
  • Amines useful in producing pharmaceutically active CNS compounds
    Patent number: 5099019
    Abstract: Disclosed are .DELTA..sup.9(11) -steroids (VI) and amino substituted steroids (XI) which contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain, more particularly amino steroids (Ia and Ib), aromatic steroids (II), .DELTA..sup.16 -steroids (IIIa and IIIb), reduced A-ring steroids (IV), .DELTA..sup.17(20) -steroids (Va and Vb) and .DELTA..sup.9(11) -steroids (VI) which are useful as pharmaceutical agents for treating a number of conditions.
    Type: Grant
    Filed: August 8, 1988
    Date of Patent: March 24, 1992
    Assignee: Upjohn Company
    Inventors: John M. McCall, Donald E. Ayer, E. Jonathan Jacobsen, Frederick J. VanDoornik, John R. Palmer, Harold A. Karnes
  • Process for production of prostaglandin intermediates
    Patent number: 5079371
    Abstract: The present invention is a process for the production of a ketolactone of formula III ##STR1## which comprises contacting an aldehyde lactone of formula I ##STR2## with a .beta.-ketophosphonate (X.sub.1 --O--).sub.2 --PO--CH.sub.2 --CO--X.sub.15 (II). The ketolactone (III) is a useful intermediate in the synthesis of prostaglandins.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: January 7, 1992
    Assignee: Upjohn Company
    Inventors: John C. Saddler, John H. Symonds
  • Conversion of steroidal 17-cyanohydrins to corticoids
    Patent number: 5003063
    Abstract: The invention involves a two step chemical transformation of a steroidal 17-cyanohydrin (II) ##STR1## to a 17.alpha.-hydroxy-21-halo-20-keto steroid (IV) ##STR2## intermediate which can readily be converted to pharmaceutically useful corticoids.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: March 26, 1991
    Assignee: The Upjohn Company
    Inventor: John G. Reid
  • Amino-9,10-secosteroids useful for treating head injury, spinal cord trauma or stroke
    Patent number: 4996318
    Abstract: The amino-9,10-secosteroids ##STR1## of the present invention contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain and are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: February 26, 1991
    Assignee: The Upjohn Company
    Inventors: Martin Gall, Robert I. Higuchi
  • Steroidal 17.alpha.-silyl ethers and process to corticoids and progesterones
    Patent number: 4977255
    Abstract: 17.beta.-Cyano-17.alpha.-hydroxy steroids (I) are transformed to 17.alpha.-halo silyl ethers (II) which are intermediates useful in the production of progesterones (V), 17-hydroxyprogesterones (VI), corticoids (VII) and 21-halo corticoids (III) which can readily be transformed to corticoids (VII).
    Type: Grant
    Filed: April 7, 1989
    Date of Patent: December 11, 1990
    Assignee: The Upjohn Company
    Inventors: Douglas A. Livingston, Bruce A. Pearlman, Scott Denmark
  • 11a-hydroxy steroid diester
    Patent number: 4948533
    Abstract: The present invention relates to 21-(3-carboxy-1-oxopropoxy) -17.alpha.-hydroxy-11.alpha.-(3,3-dimethyl-1-oxobutoxy)pregna-1,4-diene-3, 20 dione and pharmaceutically acceptable salts thereof which are useful steroid prodrugs.
    Type: Grant
    Filed: February 16, 1989
    Date of Patent: August 14, 1990
    Assignee: The Upjohn Company
    Inventors: John M. Braughler, Edward D. Hall, Wendell Wierenga, John M. McCall
  • 16.alpha.-methylation process
    Patent number: 4929395
    Abstract: C.sub.16 -unsaturated corticoids are readily transformed to the corresponding 16.alpha.-methyl-17.alpha.-hydroxy corticoids by use of a .DELTA..sup.17 (.sup.20)-20-silyl ether.
    Type: Grant
    Filed: November 14, 1986
    Date of Patent: May 29, 1990
    Assignee: The Upjohn Company
    Inventors: Verlan H. VanRheenen, Joel E. Huber
  • 17.beta.-cyano-9.alpha.,17.alpha.-dihydroxyandrost-4-en-3-one
    Patent number: 4921638
    Abstract: The invention is the compound 17.beta.-cyano-9.alpha., 17.alpha.-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17.alpha.-halo silyl ethers (II).
    Type: Grant
    Filed: October 3, 1988
    Date of Patent: May 1, 1990
    Assignee: The Upjohn Company
    Inventors: Douglas A. Livingston, Bruce A. Pearlman, Scott Denmark, Joel E. Huber
  • 16.alpha.-methyl-17.alpha. 20-epoxysteroid and process
    Patent number: 4891426
    Abstract: C.sub.16 -unsaturated corticoids are readily transformed to the corresponding 16.alpha.-methyl-17.alpha.-hydroxy corticoids by use of a .DELTA.17(20)-20-silyl ether.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: January 2, 1990
    Assignee: The Upjohn Company
    Inventors: Verlan H. VanRheenen, Joel E. Huber
  • Flurbiprofen intermediate
    Patent number: 4885404
    Abstract: Disclosed is a process for the production of acids of the formula ##STR1## wherein R is 2-fluoro-4-(1,1'-biphenyl), 4-(2-methylpropyl)phenyl, 6-methoxy-2-napthyl, 3-benzophenyl, 4-(2-thienylcarbonyl)-phenyl or 7-chlorocarbazole-3-yl which comprises contacting an organometallic compound of the formula R--M--R.sub.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: December 5, 1989
    Assignee: The Upjohn Company
    Inventor: Peter G. M. Wuts
  • 11.beta.,17.alpha.-Dihydroxy-17.beta.-cyano-androstanes
    Patent number: 4831131
    Abstract: Using cyanohydrin intermediates, 17-keto steroids are transformed to corticoids and 17.alpha.-acyl progesterones.
    Type: Grant
    Filed: March 5, 1986
    Date of Patent: May 16, 1989
    Assignee: The Upjohn Company
    Inventor: Verlan H. VanRheenen
  • Microbial .DELTA.1-dehydrogenation process using a scavenger of toxic oxygen
    Patent number: 4749649
    Abstract: A process for converting 1,2-saturated 3-keto steroids to 1,2-dehydro steroids which are useful steroid intermediates. The process involves exposing the substrate to steroid-1-dehydrogenase activity in the presence of an added electron carrier and one or more added scavengers of a toxic oxygen species.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: June 7, 1988
    Assignee: The Upjohn Company
    Inventors: Timothy W. Evans, Leo A. Kominek, Holly J. Wolf, Sheryl L. Henderson
  • Non-aromatic oxygenated strong acid dehydration of 9.alpha.-hydroxyandrostenediones
    Patent number: RE33364
    Abstract: The present invention discloses a process for the production of androsta-4,9(11)-diene-3,17-dione type compounds from 9.alpha.-hydroxyandrostenedione type compounds by non-aromatic oxygenated strong acid dehydration.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: October 2, 1990
    Assignee: The Upjohn Company
    Inventors: John M. Beaton, Joel E. Huber, Amphlett G. Padilla, Max E. Breuer