Patents Represented by Attorney Paul Thompson
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Patent number: 5660711Abstract: A process is described for preparing 3-exomethylene cephalosporanic acid derivatives for use in the synthesis of cephalosporin antibiotics such as ceftibuten. The process comprises electrochemical reduction of a compound of the formula (IV) ##STR1## wherein: R.sup.3 is CH.sub.3 C(O)--; ##STR2## is an optional sulfoxide group; n is 2 or 3; R.sup.1 is H and R is H or NHR.sup.2, where R.sup.2 is H or a protecting group selected from C.sub.6 H.sub.5 CH.sub.2 OC(O)--, C.sub.6 H.sub.5 C(O)-- or C.sub.1 -C.sub.6 alkoxy-C(O)--; or wherein R and R.sup.1 together with the carbon atom to which they are attached comprise --C(O)--, and produces the desired 3-exomethylene compounds with low levels of the corresponding 3-methyl tautomers.Type: GrantFiled: December 8, 1995Date of Patent: August 26, 1997Assignee: Schering CorporationInventors: Derek Walker, Junning Lee, Charles R. Martin, Haiyan Zhang, Loris Sogli, Ermanno Bernasconi, Vinod Parakkal Menon
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Patent number: 5607931Abstract: Amides of the formula ##STR1## wherein: R.sup.1 is A and R.sup.2 is B; R.sup.1 is B and R.sup.2 is A; or R.sup.1 and R.sup.2 are independently selected from the group B;A is phenyl, substituted phenyl, heteroaryl, or substituted heteroaryl;B is cycloalkyl, substituted cycloalkyl, heterocycloalkyl, or substituted heterocycloalkyl;R.sup.3 is an alkyl chain of 1 to 25 carbon atoms, branched or straight; an alkenyl chain of 2 to 25 carbon atoms, branched or straight; a substituted alkyl chain; a substituted alkenyl chain; an interrupted alkyl chain; an interrupted alkenyl chain; a substituted interrupted alkyl chain; or a substituted interrupted alkenyl chain;R.sup.4 is hydrogen, lower alkyl, phenyl, Q-substituted phenyl, heteroaryl or Q-substituted heteroaryl;R.sup.6 and R.sup.7 are both H, or R.sup.6 and R.sup.7 together represent .dbd.Type: GrantFiled: March 20, 1995Date of Patent: March 4, 1997Assignee: Schering CorporationInventor: Sundeep Dugar
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Patent number: 5599906Abstract: Hybrid regulatory proteins are provided which contain amino acid sequences that are susceptible to cleavage by specific proteolytic enzymes. When acted upon by such enzymes, the hybrid regulatory proteins are rendered substantially less active, thereby altering the rate of production of products of indicator genes that are controlled by the regulatory proteins. Also provided are DNAs encoding such regulatory proteins, recombinant vectors and transformed eukaryotic cells containing such DNAs, and methods for identifying inhibitors of the specific proteolytic enzymes.Type: GrantFiled: November 3, 1994Date of Patent: February 4, 1997Assignee: Schering CorporationInventor: Bimalendu Dasmahapatra
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Patent number: 5571910Abstract: A process is described for preparing 3-exomethylene cephalosporanic acid derivatives for use in the synthesis of cephalosporin antibiotics such as ceftibuten. The process comprises electrochemical reduction of a compound of the formula (IV) ##STR1## wherein: R.sup.3 is CH.sub.3 C(O)--; ##STR2## is an optional sulfoxide group; n is 2 or 3; R.sup.1 is H and R is H or NHR.sup.2, where R.sup.2 is H or a protecting group selected from C.sub.6 H.sub.5 CH.sub.2 OC(O)--, C.sub.6 H.sub.5 C(O)-- or C.sub.1 -C.sub.6 alkoxy--C(O)--; or wherein R and R.sup.1 together with the carbon atom to which they are attached comprise --C(O)--, and produces the desired 3-exomethylene compounds with low levels of the corresponding 3-methyl tautomers.Type: GrantFiled: May 26, 1995Date of Patent: November 5, 1996Assignee: Schering CorporationInventors: Derek Walker, Junning Lee, Charles R. Martin, Haiyan Zhang, Loris Sogli, Ermanno Bernasconi
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Patent number: 5545558Abstract: A process for the preparation of a chiral .alpha.-hydroxylketone, or ester thereof, comprising hydrolyzing an ester of said .alpha.-hydroxyketone with an enzyme that has a specificity for one enantiomer, or by esterifying said .alpha.-hydroxyketone with an esterifying agent in the presence of an enzyme that favors one enantiomer.Type: GrantFiled: March 29, 1994Date of Patent: August 13, 1996Assignee: Schering CorporationInventor: Dinesh Gala
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Patent number: 5502222Abstract: Described is a process for the regioselective dehydration of 11-hydroxy steroids using PCl.sub.5, PCl.sub.3, POCl.sub.3 or either SO.sub. Cl.sub.2 and imidazole, or PPh.sub.3 and CCl.sub.4. The disclosed process selectively forms .increment..sup.9,11 steroids from either 11-.alpha.- or 11-.beta.-hydroxy steroids, and can also be used for the one-step conversion of 11,21-dihydroxy steroids to 21-chloro-.increment..sup.9,11 steroids.Type: GrantFiled: June 1, 1994Date of Patent: March 26, 1996Assignee: Schering CorporationInventors: Xiaoyong Fu, Tiruvettipuram K. Thiruvengadam, Chou-Hong Tann, Junning Lee, Cesar Colon
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Patent number: 5502183Abstract: Novel steroids having a 9.alpha.-hydroxy or a 9.alpha.-carbonate substituent can be prepared from 9.alpha.-hydroxyandrostenedione and can be utilized in the synthesis of commercially valuable corticosteroids such as betamethasone. The 9.alpha.-carbonates are prepared by reaction of the corresponding 9.alpha.-hydroxy steroid with a sequence of excess base, trialkylsilyl chloride, alkyl haloformate and alkanol or by using excess base, alkyl haloformate and alkoxide. 9.alpha.-Carbonate-17-keto compounds can be treated with lithium acetylide and a lithium salt to afford the corresponding 17.alpha.-ethynyl-17.beta.-hydroxy-9.alpha.-carbonate. This compound is then esterified with a novel series of reagents to give the 17-ester which can be reduced the corresponding 17-allene. Oxidation of this allene to the bis-epoxide compound, followed by treatment with an alkali metal salt of a carboxylic acid under phase transfer conditions gives the 17.alpha.-hydroxy 21-ester 9.alpha.-carbonate. Elimination of the 9.alpha.Type: GrantFiled: July 25, 1994Date of Patent: March 26, 1996Assignee: Schering CorporationInventors: David R. Andrews, Anantha R. Sudhakar
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Patent number: 5502186Abstract: Disclosed are a process and intermediates of the formula ##STR1## wherein R is --CH.sub.3 or --C(O)--OR.sup.1, and R.sup.1 is C.sub.1 -C.sub.6 alkyl or --CH.sub.2 C.sub.6 H.sub.5 ; or the formula ##STR2## wherein: R.sup.2 is H or OH, R is --C(O)OR.sup.1 and R.sup.1 is C.sub.1 -C.sub.6 alkyl or --CH.sub.2 C.sub.6 H.sub.5, or where R.sup.2 is H, R can also be CH.sub.3 ; for preparing benzazepine intermediates of the formula ##STR3## The benzazepine intermediates are useful for preparing benzazepines having activity as selective D1 receptor antagonists.Type: GrantFiled: May 23, 1995Date of Patent: March 26, 1996Assignee: Schering CorporationInventors: Donald Hou, Richard W. Draper, Gary M. Lee, Janet L. Mas
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Patent number: 5486625Abstract: Described is a process for preparing chiral compounds of the formula ##STR1## wherein X.sup.1 and X.sup.2 are independently F or Cl, and Y is Cl, Br or I, comprising reacting a triol of the formula ##STR2## wherein X.sup.1 and X.sup.2 are as defined above, with acetone in the presence of a catalyst, then with a halogen selected from Cl.sub.2, Br.sub.2 or I.sub.2, or N-bromosuccinimide or N-iodosuccinimide.Type: GrantFiled: July 8, 1994Date of Patent: January 23, 1996Assignee: Schering CorporationInventors: William Leong, Lyman H. Smith
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Patent number: 5480640Abstract: Described is a method for treating carcinoma of the prostate using recombinant human alpha interferon via intraprostatic or intralesional injection.Type: GrantFiled: May 2, 1995Date of Patent: January 2, 1996Assignee: Schering CorporationInventors: Alvaro Morales, James W. L. Wilson
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Patent number: 5463051Abstract: Disclosed are a process and intermediates of the formulae ##STR1## wherein X.sup.- is halide, BF.sub.4.sup.-, R.sup.3 SO.sub.3.sup.-, wherein R.sup.3 is C.sub.1 -C.sub.6 alkyl, CF.sub.3, C.sub.1 -C.sub.6 alkylphenyl or phenyl, and Q is a group of the formula ##STR2## wherein R is C.sub.1 -C.sub.6 alkyl; useful for preparing benzazepine intermediates of the formula ##STR3## These benzazepine intermediates are useful for preparing benzazepines having activity as selective D1 receptor antagonists.Type: GrantFiled: September 27, 1993Date of Patent: October 31, 1995Assignee: Schering CorporationInventors: Donald Hou, Richard W. Draper, Gary M. Lee, Janet L. Mas, Ingrid Mergelsberg
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Patent number: 5461147Abstract: Disclosed are a process and intermediates of the formula ##STR1## wherein R is --CH.sub.3 or --C(O)--OR.sup.1, and R.sup.1 is C.sub.1 -C.sub.6 alkyl or --CH.sub.2 C.sub.6 H.sub.5 ; or the formula ##STR2## wherein: R.sup.2 is H or OH, R is --C(O)OR.sup.1 and R.sup.1 is C.sub.1 -C.sub.6 alkyl or --CH.sub.2 C.sub.6 H.sub.5, or where R.sup.2 is H, R can also be CH.sub.3 ; for preparing benzazepine intermediates of the formula ##STR3## The benzazepine intermediates are useful for preparing benzazepines having activity as selective D1 receptor antagonists.Type: GrantFiled: September 27, 1993Date of Patent: October 24, 1995Assignee: Schering CorporationInventors: Donald Hou, Richard W. Draper, Gary M. Lee, Janet L. Mas
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Patent number: 5461148Abstract: Disclosed are a process and intermediates of the formulae ##STR1## wherein R is --CH.sub.2 OH or --OH and R.sup.3 is H or C.sub.1 -C.sub.6 alkyl; useful for preparing benzazepines of the formula ##STR2## having activity as selective D1 antangonists.Type: GrantFiled: September 27, 1993Date of Patent: October 24, 1995Assignee: Schering CorporationInventors: Guang-Zhong Wu, Martin Steinman, Yee-Shing Wong
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Patent number: 5442093Abstract: Disclosed is a process for preparing compounds of the formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, comprising heating a mixture of a difluorobenzene derivative, allene, a dialkyl malonate of the formula CH.sub.2 (CO.sub.2 R).sub.2, wherein R is C.sub.1 -C.sub.6 alkyl, and a base, in a polar organic solvent in the presence of a catalyst.Type: GrantFiled: May 9, 1994Date of Patent: August 15, 1995Assignee: Schering CorporationInventor: Anantha Sudhakar
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Patent number: 5419885Abstract: A process for destructively scrubbing methyl chloride gas comprising contacting the gas with a scrubbing solution comprising ethanolamine is described.Type: GrantFiled: December 15, 1993Date of Patent: May 30, 1995Assignee: Schering CorporationInventors: Henry Doran, Brian Keaveny
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Patent number: 5403937Abstract: Disclosed is a process for preparing chiral compounds of the formula (I) ##STR1## wherein: X.sup.1 and X.sup.2 are independently F or Cl; and E is --SO.sub.2 R.sup.2, wherein R.sup.2 is C.sub.1 -C.sub.6 alkyl, --C.sub.6 H.sub.4 CH.sub.3 or --CF.sub.3 ; its enantiomer and racemates thereof, useful in the synthesis of tetrahydrofuran azole antifungals. Novel compounds of the formula ##STR2## wherein: X.sup.1 and X.sup.2 are independently F or Cl; B represents --C(O)Q* or --CH.sub.2 OR"; Q* represents a chiral auxiliary group; R" represents a hydroxy protecting group selected from --CH.sub.2 C.sub.6 H.sub.5, or --C(O)R.sup.1, wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; and A represents Cl, Br, I or triazolyl; are also disclosed.Type: GrantFiled: April 30, 1993Date of Patent: April 4, 1995Assignee: Schering CorporationInventors: Anil K. Saksena, Viyyoor M. Girijavallabhan, Russell E. Pike, Haiyan Wang, Raymond G. Lovey, Yi-Tsung Liu, Ashit K. Ganguly, William B. Morgan, Aleksey Zaks
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Patent number: 5395984Abstract: Described is a process for preparing 2-phenyl-1,3-propanediol by converting the 2-nitro-2-phenyl-1,3-propanediol to a nitro-dioxane of the formula ##STR1## wherein the groups R are both C.sub.1 -C.sub.6 alkyl or together comprise a C.sub.5 -C.sub.6 cycloalkyl group, or wherein one R group is H and the other is phenyl; hydrogenolysis of the nitro-dioxane to give a dioxane of the formula ##STR2## wherein R is as defined above; and hydrolyzing the dioxane to form 2-phenyl-1,3-propanediol.Type: GrantFiled: April 20, 1994Date of Patent: March 7, 1995Assignee: Schering CorporationInventors: Patrick O'Neill, Henry Doran
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Patent number: 5352832Abstract: The present invention comprises a process for the asymmetric synthesis of florfenicol, thiamphenicol or chloramphenicol, from a derivative of trans-cinnamic acid, comprising the steps:(a) converting the acid to an acid chloride using a chlorinating agent, and reducing the acid chloride to a trans allylic alcohol with a reducing agent;(b) asymmetrically epoxidizing the allylic alcohol of step (a), by reacting with t-butylhydroperoxide in the presence of a chiral epoxidation catalyst prepared from titanium (IV) isopropoxide and L-diisopropyltartaric acid, to form a chiral epoxide;(c) regioselectively opening the epoxide of step (b) by sequentially treating with sodium hydride, zinc chloride and dichloroacetonitrile to form an oxazoline;(d) stereoselective inversion/isomerization of the oxazoline of step (c) by sequentially treating with: (i) a lower alkylsulfonyl chloride and a tertiary amine base; (ii) sulfuric acid and water; (iii) an alkali metal hydroxide; to form an oxazoline;(e) optionally treating the oxType: GrantFiled: December 18, 1992Date of Patent: October 4, 1994Assignee: Schering CorporationInventors: Guang-Zhong Wu, Wanda I. Tormos
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Patent number: 5349099Abstract: Disclosed is a process for preparing allylic halides of the formula I ##STR1## wherein X is Cl, Br or I, for use as intermediates in the synthesis of substituted tetrahydrofuran azole anti-fungal agents.Type: GrantFiled: December 13, 1993Date of Patent: September 20, 1994Assignee: Schering CorporationInventors: Shen-Chun Kuo, Donald Hou, Zheng-Yun Zhan
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Patent number: 5326762Abstract: Amides of the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently heteroaryl, X-substituted heteroaryl, X-substituted phenyl, N-substituted triazinyl or N-substituted imidazolyl;and in addition, one of R.sub.1 and R.sub.2 can be as defined above and the other can be phenyl;R.sub.3 is an alkyl chain of 2 to 25 carbon atoms, saturated or unsaturated; an alkyl chain as defined substituted by one or more substituents selected from the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl; an alkyl chain as defined interrupted by one or more groups independently selected from the group consisting of --O--, --S--, --SO--, --SO.sub.2 --, --NH--, --N(lower alkyl)--, --C(O)--, phenylene, X-substituted phenylene, heteroarylene and X-substituted heteroarylene; or an interrupted alkyl chain as defined substituted by one or more substituents selected form the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl;R.sub.Type: GrantFiled: May 19, 1992Date of Patent: July 5, 1994Assignee: Schering CorporationInventors: John Clader, Sundeep Dugar, Timothy Kogan, Bradley Tait, Wayne Vaccaro