Patents by Inventor Charles W. Ryan

Charles W. Ryan has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Synthesis of nizatidine intermediate
    Patent number: 4777260
    Abstract: The present invention provides a process for preparing a novel intermediate for nizatidine.
    Type: Grant
    Filed: December 18, 1985
    Date of Patent: October 11, 1988
    Assignee: Eli Lilly and Company
    Inventors: Charles W. Ryan, Bruce A. Slomski
  • 3-sulfonylamino-4-amino phenyl acyl derivatives
    Patent number: 4645861
    Abstract: A 4-acyl-o-phenylenediamine is selectively sulfonated on the amino group meta to the acyl group to provide an important intermediate for benzimidazole pharmaceuticals. Some of the intermediates are new to organic chemistry.
    Type: Grant
    Filed: April 25, 1986
    Date of Patent: February 24, 1987
    Assignee: Eli Lilly and Company
    Inventors: Charles W. Ryan, Bruce A. Slomski
  • Isothiourea synthesis process
    Patent number: 4587344
    Abstract: N-methyl-S-methyl-N'-[2-(2-dimethylaminomethylthiazol-4-ylmethylthio)ethyl] isothiourea is prepared by the reaction of 2-dimethylaminomethyl-4-(2-aminoethyl)thiomethylthiazole with methylcarbonimidodithioic acid, dimethyl ester, and is a useful intermediate for the preparation of nizatidine, a pharmaceutically valuable H.sub.2 -receptor inhibitor.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: May 6, 1986
    Assignee: Eli Lilly and Company
    Inventor: Charles W. Ryan
  • Synthesis of alkylidene intermediates
    Patent number: 4501921
    Abstract: A stereo-selective preparation of novel sulfonated o-phenylenediamines carrying a trans-.alpha.-alkylidenebenzyl group at the 5-position, which are intermediates in the synthesis of antiviral benzimidazoles.
    Type: Grant
    Filed: November 18, 1982
    Date of Patent: February 26, 1985
    Assignee: Eli Lilly and Company
    Inventors: Charles W. Ryan, Bruce A. Slomski
  • Preparation of 6a,10a-trans-hexahydrodibenzopyranones
    Patent number: 4395560
    Abstract: Reaction of an O-methyl or O-ethyl resorcinol with a cyclohexene carbinol derivative in the presence of a catalyst affords a 6a,10a-trans-1-methoxy or 1-ethoxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one derivative.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: July 26, 1983
    Assignee: Eli Lilly and Company
    Inventor: Charles W. Ryan
  • Preparation of cis-hexahydrodibenzopyranones
    Patent number: 4171315
    Abstract: Reaction of 4-(1-hydroxy-1-methylethyl)-3-cyclohexen-1-one with a 5-substituted resorcinol in the presence of boron tribromide, boron trifluoride or stannic chloride provides, depending upon the duration of reaction, either a 2,7-dihydroxy-5-isopropylidene-9-substituted-2,6-methano-3,4,5,6-tetrahydr o-2H-1-benzoxocin or a 6a,10a-cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro- 9H-dibenzo[b,d]pyran-9-one.
    Type: Grant
    Filed: March 31, 1978
    Date of Patent: October 16, 1979
    Assignee: Eli Lilly and Company
    Inventor: Charles W. Ryan
  • 2,6-Methano-2H-1-benzoxocins
    Patent number: 4140701
    Abstract: Novel 2-oxy-5-isopropylidene-7-hydroxy-9-substituted-2,6-methano-3,4,5,6-tetrahy dro-2H-1-benzoxocins are prepared by condensing a 5-(substituted)resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a suitable catalyst. The new benzoxocin derivatives are useful in the synthesis of certain dibenzo[b,d]pyran-9-ones, valuable as anti-anxiety, analgesic, and anti-depressant drugs.
    Type: Grant
    Filed: September 8, 1977
    Date of Patent: February 20, 1979
    Assignee: Eli Lilly and Company
    Inventor: Charles W. Ryan
  • Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-ones and intermediates therefor
    Patent number: 4133816
    Abstract: Reaction of a 5-substituted resorcinol with a ketal of 4-(1-hydroxy)-1-methylethyl)-3-cyclohexen-1-one in the presence of a suitable catalyst effects condensation to provide substantially exclusively a cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibe nzo[b,d]pyran-9-one.
    Type: Grant
    Filed: May 10, 1978
    Date of Patent: January 9, 1979
    Assignee: Eli Lilly and Company
    Inventors: William B. Blanchard, Charles W. Ryan
  • Process for preparing cis-hexahydrodibenzopyranones
    Patent number: 4131614
    Abstract: Reaction of a 5-substituted resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a catalyst such as boron tribromide, boron trifluoride or stannic chloride, and in the presence of about an equimolar quantity of water, affords predominantly a cis-hexahydrodibenzopyranone in high yields.
    Type: Grant
    Filed: September 8, 1977
    Date of Patent: December 26, 1978
    Assignee: Eli Lilly and Company
    Inventor: Charles W. Ryan
  • Intermediates for 5-(tertiary alkyl) resorcinol preparation
    Patent number: 4131656
    Abstract: 2,6-Dimethoxyphenol reacts with a tertiary carbinol in the presence of an acid to provide exclusively a 1-hydroxy-2,6-dimethoxy-4-(tertiary alkyl)benzene, which when reacted with a halogenated disubstituted phosphite affords a 2,6-dimethoxy-4-(tertiary alkyl)phenyl disubstituted phosphate. Reduction of the phenyl phosphate derivative by reaction with an alkali metal affords a 1-(tertiary alkyl)-3,5-dimethoxybenzene, which upon reaction with a demethylating agent provides a 5-(tertiary alkyl)resorcinol.
    Type: Grant
    Filed: February 1, 1978
    Date of Patent: December 26, 1978
    Assignee: Eli Lilly and Company
    Inventors: Samuel J. Dominianni, Charles W. Ryan
  • Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo [b,d]pyran-9-ones and intermediates therefor
    Patent number: 4115403
    Abstract: Reaction of a 5-substituted resorcinol with a ketal of 4-(1-hydroxy-1-methylethyl)-3-cyclohexen-1-one in the presence of a suitable catalyst effects condensation to provide substantially exclusively a cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibe nzo-[b,d]pyran-9-one.
    Type: Grant
    Filed: July 12, 1977
    Date of Patent: September 19, 1978
    Assignee: Eli Lilly and Company
    Inventors: William B. Blanchard, Charles W. Ryan
  • 5-(Tertiary alkyl) resorcinol preparation and intermediates therefor
    Patent number: 4087410
    Abstract: 2,6-Dimethoxyphenol reacts with a tertiary carbinol in the presence of an acid to provide exclusively a 1-hydroxy-2,6-dimethoxy-4-tertiary alkyl)benzene, which when reacted with a halogenated disubstituted phosphite affords a 2,6-dimethoxy-4-tertiary alkyl)phenyl disubstituted phosphate. Reduction of the phenyl phosphate derivative by reaction with an alkali metal affords a 1-(tertiary alkyl)-3,5-dimethoxybenzene, which upon reaction with a demethylating agent provides a 5-(tertiary alkyl)resorcinol.
    Type: Grant
    Filed: June 14, 1976
    Date of Patent: May 2, 1978
    Assignee: Eli Lilly and Company
    Inventors: Samuel J. Dominianni, Charles W. Ryan
  • Process for converting 2,7-dihydroxy-5-isopropylidene-9-substituted-2,6-methano-3,4,5,6-tetrahy dro-2H-1-benzoxocin to trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H- dibenzo(b,d)pyran-9-one
    Patent number: 4054583
    Abstract: Reaction of an aluminum halide with a 2,7-dihydroxy-5-isopropylidene-9-substituted-2,6-methano-3,4,5,6-tetrahydr o-2H-1-benzoxocin in an organic solvent effects cleavage of the pyran ring system with concomitant recyclization to provide exclusively a trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-one.
    Type: Grant
    Filed: July 6, 1976
    Date of Patent: October 18, 1977
    Assignee: Eli Lilly and Company
    Inventors: William B. Blanchard, Charles W. Ryan
  • Process for converting cis-hexahydrodibenzo[b,d]pyran-9-ones to trans-hexahydrodibenzo[b,d]-pyran-9-ones
    Patent number: 4054582
    Abstract: Reaction of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibe nzo[b,d]pyran-9-ones with an aluminum halide in an unreactive organic solvent effects complete epimerization to provide the corresponding trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-one.
    Type: Grant
    Filed: July 6, 1976
    Date of Patent: October 18, 1977
    Assignee: Eli Lilly and Company
    Inventors: William B. Blanchard, Charles W. Ryan
  • Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-ones and intermediates therefor
    Patent number: 4054581
    Abstract: Reaction of a 5-substituted resorcinol with a ketal of 4-(1-hydroxy-1-methylethyl)-3-cyclohexen-1-one in the presence of a suitable catalyst effects condensation to provide substantially exclusively a cis-1-hydroxy-3-substituted-6-6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibe nzo[b,d]pyran-9-one.
    Type: Grant
    Filed: July 6, 1976
    Date of Patent: October 18, 1977
    Assignee: Eli Lilly and Company
    Inventors: William B. Blanchard, Charles W. Ryan
  • Process for preparing cefazolin
    Patent number: 3954745
    Abstract: Cefazolin is prepared by treating a solvate of N,N-dimethylformamide and the hydrochloride salt of 7-amino-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid with 1H-tetrazole-1-acetyl chloride in the presence of N,N-dimethylacetamide as solvent.
    Type: Grant
    Filed: September 12, 1974
    Date of Patent: May 4, 1976
    Assignee: Eli Lilly and Company
    Inventors: Billy G. Jackson, Charles W. Ryan
  • Process for acylating a 7-aminocephalosporin
    Patent number: 3943126
    Abstract: A 7-aminocephalosporin is acylated to a 7-acylamidocephalosporin by reaction with the pentachlorophenyl ester of sydnone-3-acetic acid or 1-tetrazoleacetic acid.
    Type: Grant
    Filed: November 15, 1973
    Date of Patent: March 9, 1976
    Assignee: Eli Lilly and Company
    Inventors: Charles W. Ryan, William B. Blanchard