Patents Assigned to Ono Pharmaceutical Company
  • Patent number: 5622984
    Abstract: Amidinophenol derivatives of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are (i) H, (ii) C1-4 alkoxy, (iv) C2-5 acyl, (v) halogen, (vi) NO.sub.2, (vii) benzoyl, (viii) COOR.sup.4 (in which R.sup.4 is C1-3 alkyl); A is bond, C1-4 alkylene, --C(R.sup.5).dbd.C(R.sup.6)--(in which R.sup.5 and R.sup.6 are H or C1-4 alkyl; R.sup.3 is (i) CON(R.sup.7)(R.sup.8), (ii) CON(R.sup.9)--CH(R.sup.7)(R.sup.8) or (iii) ##STR2## in which R.sup.7 and R.sup.8 are (1) H,(2) phenyl, (3) C7-10 phenylalkyl, (4) phenyl or C7-10 phenylalkyl substituted by 1 or 2 C1-4 alkyl, halogen or R.sup.11 --COOR.sup.12 (in which R.sup.11 is bond, C1-8 alkylene, C2-8 alkenylene, C2-8 alkynylene; R.sup.12 is H, C1-4 alkyl, C7-10 phenylalkyl, phenyl, allyl, propargyl), (5) C1-10 alkyl, (6) C2-10 alkenyl having 1 to 3 double bonds, (7) C2-10 alkynyl having 1 or 2 triple bonds, (8) R.sup.11a --COXR.sup.12 (in which R.sup.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: April 22, 1997
    Assignee: Ono Pharmaceutical Company, Limited
    Inventors: Hisao Nakai, Masanori Kawamura, Tsumoru Miyamoto
  • Patent number: 4479966
    Abstract: Prostaglandin I.sub.2 analogues of the formula: ##STR1## [wherein the symbol between the carbon atoms in positions 5 and 6 represents a single or double bond, Y represents ethylene or trans-vinylene, R.sup.1 represents hydrogen, alkyl of 1 to 12 carbon atoms, aralkyl of 7 to 12 carbon atoms, cycloalkyl of 4 to 7 carbon atoms optionally substituted by alkyl of 1 to 4 carbon atoms, phenyl optionally substituted by chlorine, trifluoromethyl, alkyl of 1 to 4 carbon atoms or phenyl, a --C.sub.m H.sub.2m COOR.sup.7 group (wherein m represents an integer of from 1 to 12 and R.sup.7 represents alkyl of 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.8 group (wherein n represents an integer of from 2 to 12 and R.sup.8 represents hydrogen or alkyl of 1 to 4 carbon atoms) or a ##STR2## group (wherein R.sup.9 and R.sup.10 each represent alkyl of 1 to 4 carbon atoms and n is as hereinbefore defined), R.sup.2 represents hydrogen or a hydroxy-protecting group, R.sup.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: October 30, 1984
    Assignee: Ono Pharmaceutical Company, Ltd.
    Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai
  • Patent number: 4165437
    Abstract: The present invention relates to prostaglandin analogues of the general formula: ##STR1## [wherein X represents cis or trans-vinylene or ethylene, R represents ##STR2## R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.2 represents a hydrogen atom or a methyl group, R.sup.3 represents a straight- or branched-chain alkylene group containing from 1 to 7 carbon atoms and R.sup.4 represents a cycloalkyl group containing from 5 to 7 carbon atoms, a grouping of the formula: ##STR3## (wherein R.sup.5 and R.sup.6, which may be the same or different, each represent a hydrogen atom or halogen atom, a trifluoromethyl group or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms), or a grouping of the formula: ##STR4## (wherein R.sup.5 and R.sup.6 are as hereinbefore defined), or R.sup.3 and R.sup.
    Type: Grant
    Filed: August 17, 1978
    Date of Patent: August 21, 1979
    Assignee: Ono Pharmaceutical Company, Ltd.
    Inventors: Masaki Hayashi, Seiji Kori, Yoshinobu Arai, Takanori Okada, Yoshitaka Konishi
  • Patent number: 4145555
    Abstract: The present invention relates to prostaglandin analogues of the general formula: ##STR1## ?wherein X represents cis or trans-vinylene or ethylene, Z represents ##STR2## R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.2 represents a hydrogen atom or a methyl group, R.sup.3 represents a straight- or branched-chain alkylene group containing from 1 to 7 carbon atoms and R.sup.4 represents a cycloalkyl group containing from 5 to 7 carbon atoms, a grouping of the formula: ##STR3## (wherein R.sup.5 and R.sup.6, which may be the same or different, each represent a hydrogen atom or halogen atom, a trifluoromethyl group or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms), or a grouping of the formula: ##STR4## (wherein R.sup.5 and R.sup.6 are as hereinbefore defined), or R.sup.3 and R.sup.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: March 20, 1979
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Yoshinobu Arai, Takanori Okada, Yoshitaka Konishi
  • Patent number: 4140712
    Abstract: The present invention relates to 20-hydroxy prostaglandins of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## and X represents ethylene or cis-vinylene and Y represents trans-vinylene, or X and Y each represent ethylene, R represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.1 , R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, each represent a hydrogen atom or a methyl or ethyl group, and n represents zero or an integer from 1 to 3 inclusive, and cyclodextrin clathrates of such acids and esters and, when R represents a hydrogen atom, the non-toxic salts thereof.These compounds exhibit characteristic prostaglandin activity.
    Type: Grant
    Filed: February 5, 1975
    Date of Patent: February 20, 1979
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hajimu Miyake
  • Patent number: 4128720
    Abstract: Prostaglandins of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 10 carbon atoms, R.sup.2 represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, R.sup.3 represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms, or a grouping of the formula: ##STR3## wherein R.sup.4 and R.sup.5 each represents a hydrogen or halogen atom, a trifluoromethyl group or an alkyl group containing from 1 to 3 carbon atoms, or R.sup.2 and R.sup.
    Type: Grant
    Filed: February 11, 1976
    Date of Patent: December 5, 1978
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hajimu Miyake
  • Patent number: 4117119
    Abstract: Prostaglandin analogues of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents trans-vinylene or ethylene and Y represents cis-vinylene or ethylene, R represents hydrogen or alkyl of 1 through 12 carbon atoms, R.sup.1, R.sup.2 and R.sup.3 represent hydrogen, or alkyl of 1 through 12 carbon atoms or an aryl group, with the proviso that at least one of the symbols R.sup.1, R.sup.2 and R.sup.3 represents an alkyl or aryl group, are new compounds possessing useful pharmacological properties; they are especially useful for the treatment of gastric ulceration.
    Type: Grant
    Filed: May 6, 1977
    Date of Patent: September 26, 1978
    Assignee: Ono Pharmaceutical Company
    Inventors: Masayasu Kurono, Hisao Nakai, Takashi Muryobayashi
  • Patent number: 4110341
    Abstract: Prostaglandin analogues of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R.sup.1 represents a straight- or branched-chain alkyl group containing from 4 to 10 carbon atoms, and R.sup.2 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms and cyclodextrin clathrates of such acids and esters and, when R.sup.2 represents a hydrogen atom, non-toxic salts thereof, the bonds attaching the epidithio radical to the carbon atoms in the 9- and 11-positions in the grouping of formula VA being either botn in .alpha.-configuration or both in .beta.-configuration are disclosed.These compounds exhibit characteristic prostaglandin properties.
    Type: Grant
    Filed: February 4, 1977
    Date of Patent: August 29, 1978
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hajimu Miyake
  • Patent number: 4087620
    Abstract: The present invention relates to 15-cycloalkyl-prostaglandins of the formula: ##STR1## WHEREIN A represents a grouping of the formula: ##STR2## W represents ethylene or trans-vinylene, X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.1 represents a hydrogen atom or a methyl or ethyl group, R.sup.2 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms or a phenyl group unsubstituted or substituted by an alkyl group containing from 1 to 3 carbon atoms, R.sup.3 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 3 carbon atoms, and n represents 4 or 5) and cyclodextrin clathrates of such acids and esters and, when R represents a hydrogen atom, non-toxic salts thereof.These new compounds exhibit characteristic prostaglandin-like activities.
    Type: Grant
    Filed: July 7, 1976
    Date of Patent: May 2, 1978
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Isao Ohyama, Sadahiko Iguchi, Takanori Okada
  • Patent number: 4070537
    Abstract: The present invention relates to 17-oxo-17-phenyl-prostaglandins having the following structural formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom or a methyl or ethyl group, R.sup.2 and R.sup.3, which may be the same or different, each represent a hydrogen or halogen atom, a trifluoromethyl group or a straight- or branched-chain alkyl group containing from 1 to 3 carbon atoms, and R.sup.4 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms and cyclodextrin clathrates of such acids and esters, and when R.sup.4 represents a hydrogen atom, non-toxic salts thereof.These compounds exhibit characteristic prostaglandin activity, e.g., abortifacient activity, stimulation activity on uterine contraction, and so on.
    Type: Grant
    Filed: April 22, 1976
    Date of Patent: January 24, 1978
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hajimu Miyake, Kimiichiro Matsumoto
  • Patent number: 4069387
    Abstract: The present invention relates to compounds of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## B represents a single bond or a straight- or branched-chain alkylene group containing from 1 to 9 carbon atoms, W represents ethylene or trans-vinylene, X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R represents a hydroxymethyl group or a grouping of the formula --COOR.sup.4, in which R.sup.4 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.1 represents a hydrogen atom or a methyl or ethyl group, R.sup.2 represents a hydrogen atom or a methyl or ethyl group and R.sup.3 represents a hydrogen or chlorine atom or a hydroxy group and cyclodextrin clathrates of such alcohols, acids and esters and, when R.sup.4 in the formula --COOR.sup.4 represents a hydrogen atom, non-toxic salts thereof, and intermediates therefor. These compounds exhibit characteristic prostaglandin-like activity.
    Type: Grant
    Filed: July 29, 1976
    Date of Patent: January 17, 1978
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Katsuichi Shimoji
  • Patent number: 4066751
    Abstract: Prostaglandin analogues of the formula: ##STR1## wherein X represents oxygen or sulphur, R.sup.1 and R.sup.2 each represent hydrogen or alkyl of from 1 to 3 carbon atoms, alkenyl of from 2 to 4 carbon atoms or trifluoromethyl, and the double bonds depicted in positions C.sub.5 -C.sub.6 and C.sub.13 -C.sub.14 are cis and trans respectively. These compounds are indicated in the treatment of impaired fertility, induction of labor or termination of pregnancy in females.
    Type: Grant
    Filed: October 23, 1975
    Date of Patent: January 3, 1978
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Tadao Tanouchi
  • Patent number: 4065632
    Abstract: The present invention relates to compounds of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## B represents an oxygen or sulphur atom, R.sup.1 and R.sup.2, which may be the same or different, each represent a hydrogen or halogen atom, a trifluoromethyl group, or a straight- or branched-chain alkyl or alkoxy group containing from 1 to 4 carbon atoms, R represents a group of the formula --COOR.sup.3, in which R.sup.3 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, or a group of the formula --CH.sub.2 OR.sup.4, in which R.sup.4 represents a hydrogen atom or an alkylcarbonyl group containing from 2 to 5 carbon atoms and the double bonds depicted in positions C.sub.2 -C.sub.3, C.sub.5 -C.sub.6 and C.sub.13 -C.sub.14 are trans, cis and trans respectively, the cyclodextrin clathrates thereof and, when R.sup.3 in the group --COOR.sup.3 represents a hydrogen atom, non-toxic salts thereof.
    Type: Grant
    Filed: August 12, 1976
    Date of Patent: December 27, 1977
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hajimu Miyake, Takanori Okada
  • Patent number: 4061865
    Abstract: Prostaglandin compounds of the formula: ##STR1## wherein A represents a grouping of formula II, III or IV indicated below and (i)R.sub.1 represents an unsubstituted n-butyl, n-pentyl, n-hexyl or n-heptyl radical, or such a radical carrying one, two or three alkyl substituents of 1 to 4 carbon atoms, or R.sub.1 represents a methyl, ethyl, propyl or butyl radical carrying a phenyl, cyclohexyl or cyclopentyl substituent, R.sub.2 represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, and R.sub.3 represents a hydrogen atom, or (ii) R.sub.1 represents n-butyl, or n-butyl or n-pentyl carrying one, two or three alkyl substituents of 1 to 4 carbon atoms, or R.sub.1 represents a methyl, ethyl, propyl or butyl radical carrying a phenyl, cyclohexyl or cyclopentyl substituent, R.sub.2 represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, and R.sub.3 represents an alkyl radical of 1 to 4 carbon atoms are disclosed. These compounds exhibit characteristic prostaglandin-like activity.
    Type: Grant
    Filed: August 11, 1975
    Date of Patent: December 6, 1977
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Tadao Tanouchi, Hiroyuki Ito, Isao Ohyama
  • Patent number: 4045468
    Abstract: Prostaglandin analogues of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents trans-vinylene or ethylene and Y represents cis-vinylene or ethylene, R represents hydrogen or alkyl of 1 through 12 carbon atoms, R.sup.1, R.sup.2 and R.sup.3 represent hydrogen, or alkyl of 1 through 12 carbon atoms or an aryl group, with the proviso that at least one of the symbols R.sup.1, R.sup.2 and R.sup.3 represents an alkyl or aryl group, are new compounds possessing useful pharmacological properties; they are especially useful for the treatment of gastric ulceration.
    Type: Grant
    Filed: March 11, 1975
    Date of Patent: August 30, 1977
    Assignee: Ono Pharmaceutical Company
    Inventors: Masayasu Kurono, Hisao Nakai, Takashi Muryobayashi
  • Patent number: 4024174
    Abstract: Trans-.DELTA..sup.2 -prostaglandin compounds are disclosed of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## R.sup.1 represents an alkyl group containing from 1 to 10 carbon atoms, or an alkyl group containing from 1 to 6 carbon atoms carrying a phenyl substituent or a cycloalkyl substituent of 5 to 7 carbon atoms, R.sup.2 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, and R.sup.3.sup.' represents a hydrogen atom or an alkyl group containing from 1 to 12 carbon atoms, the double bonds in the 2- and 5-positions being in the trans- and cis-configurations respectively. These compounds are indicated in the management of conditions such as autoimmune conditions, e.g. rheumatoid arthritis.
    Type: Grant
    Filed: December 19, 1964
    Date of Patent: May 17, 1977
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hirohisa Wakatsuka, Yoshitaka Konishi
  • Patent number: 3962312
    Abstract: Prostaglandin compounds of the formula: ##SPC1##Wherein A represents a grouping of formula II, III or IV indicated below and (i)R.sub.1 represents an unsubstituted n-butyl, n-pentyl, n-hexyl or n-heptyl radical, or such a radical carrying one, two or three alkyl substituents of 1 to 4 carbon atoms, or R.sub.1 represents a methyl, ethyl, propyl or butyl radical carrying a phenyl, cyclohexyl or cyclopentyl substituent, R.sub.2 represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, and R.sub.3 represents a hydrogen atom, or (ii) R.sub.1 represents n-butyl, or n-butyl or n-pentyl carrying one, two or three alkyl substituents of 1 to 4 carbon atoms, or R.sub.1 represents a methyl, ethyl, propyl or butyl radical carrying a phenyl, cyclohexyl or cyclopentyl substituent, R.sub.2 represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, and R.sub.3 represents an alkyl radical of 1 to 4 carbon atoms are disclosed. These compounds exhibit characteristic prostaglandin-like activity.
    Type: Grant
    Filed: September 19, 1973
    Date of Patent: June 8, 1976
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Tadao Tanouchi, Hiroyuki Ito, Isao Ohyama
  • Patent number: 3953435
    Abstract: Prostaglandin analogues of the formula:- ##SPC1##Wherein A represents a PGF or PGE grouping, X represents ethylene or cis-vinylene, Y represents ethylene or transvinylene, R.sup.1 represents hydrogen or alkyl of 1 to 4 carbon atoms, R.sup.2 represents alkyl of 1 to 10 carbon atoms, or alkyl of 1 to 4 carbon atoms substituted by phenyl or cycloalkyl containing from 5 to 7 carbon atoms, or R.sup.2 represents a grouping of the formula:- ##SPC2##Wherein R.sup.3 represents alkylene of 1 to 4 carbon atoms, R.sup.4 represents oxygen or sulphur or sulphinyl, and R.sup.5 and R.sup.6 represent hydrogen, halogen, trifluoromethyl, alkyl of 1 to 3 carbon atoms are new compounds possessing pharmacological properties.
    Type: Grant
    Filed: December 30, 1974
    Date of Patent: April 27, 1976
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hirofumi Endo
  • Patent number: 3953495
    Abstract: The present invention relates to 16-methylene prostaglandins. These compounds are useful as anti-ulcer agents, bronchodilators and so on.
    Type: Grant
    Filed: August 29, 1974
    Date of Patent: April 27, 1976
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Hajimu Miyake