Patents Assigned to Wakunaga Seiyaku Kabushiki Kaisha
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Patent number: 5254685Abstract: A tricyclic compound represented by the general formula (1) and salts thereof. ##STR1## A method for producing the tricyclic compound and salts thereof, and an antimicrobial agent containing the tricyclic compound and salts thereof as an active ingredient are also disclosed.Type: GrantFiled: August 7, 1991Date of Patent: October 19, 1993Assignees: Wakunaga Seiyaku Kabushiki Kaisha, Fujisawa Pharmaceutical Co., Ltd.Inventors: Masaharu Yokomoto, Akira Yazaki, Norihiro Hayashi, Shunso Hatono, Satoshi Inoue, Yasuhiro Kuramoto
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Patent number: 5245037Abstract: Antibacterial quinolone derivatives represented by the following formula [I] and salts thereof are disclosed. ##STR1## wherein R.sup.1 means a hydrogen atom or a carboxyl-protecting group; R.sup.2 denotes a hydrogen or halogen atom or a hydroxyl, lower alkoxyl, amino, aralkylamino, or mono- or di-(lower alkyl)amino group; A represents an oxygen or sulfur atom or N--R.sup.3 in which R.sup.3 is a hydrogen atom or an amino-protecting group; X is a hydrogen or halogen atom; Y means a nitrogen atom or C--R.sup.4 in which R.sup.4 is a hydrogen or halogen atom or a lower alkyl or lower alkoxyl group; and Z denotes a halogen atom or a substituted or unsubstituted heterocyclic group having at least one nitrogen atom as a hetero atom.Type: GrantFiled: March 23, 1990Date of Patent: September 14, 1993Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Yasuhiro Kuramoto, Masayasu Okuhira, Takashi Yatsunami
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Patent number: 5231114Abstract: A lipid peroxidation inhibitor contains a polysulfide compound represented by formula (I) as an active ingredient:R.sup.1 --(S).sub.m --R.sup.2 (I)wherein R.sup.1 and R.sup.2 are same or different hydrocarbon chains having 1 to 16 carbon atoms and m is an integer of 3 to 10. Among compounds (I) are found novel which are:R.sup.3 --(S).sub.n --R.sup.4 (II)wherein R.sup.3 and R.sup.4 are same or different lower alkenyl groups and n is an integer of 6 to 10. Pharmaceutical compositions which contain a polysulfide compound represented by formula (I) as an active ingredient, for preventing and curing diseases of thrombosis, arteiosclerosis, liver troubles, pulmonary edema, skin troubles, eye troubles and aging are also disclosed.Type: GrantFiled: April 13, 1992Date of Patent: July 27, 1993Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Shoji Awazu, Toshiharu Horie, Yukihiro Kodera, Shinji Nagae, Hiromichi Matsuura, Yoichi Itakura
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Patent number: 5208245Abstract: The present invention provides dihydropyridine derivatives represented by the following formula (I) ##STR1## and salts thereof. They have extremely strong, slow and long-acting vasodilating action and antihypertensive action with less adverse effects so that they are useful as therapeutic agents for cardiovascular diseases.Type: GrantFiled: May 7, 1991Date of Patent: May 4, 1993Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Terukage Hirata, Yasushi Yoshimura, Masanori Kakimoto, Koichi Tamura, Harunobu Amagase
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Patent number: 5206270Abstract: A method of inhibiting melanoma cell proliferation in a mammal by administering to the mammal S-allylcysteine or a pharmaceutically acceptable salt thereof.Type: GrantFiled: March 5, 1992Date of Patent: April 27, 1993Assignee: Wakunaga Seiyaku Kabushiki KaishaInventor: Reiko F. Irie
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Patent number: 5153203Abstract: Antibacterial quinolone derivatives represented by the following formula and salts thereof are disclosed. ##STR1## wherein R.sup.1 meawns a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted phenyl group, R.sup.2 denotes a hydrogen atom or a carboxyl-protecting group, R.sup.3 represents a hydrogen or halogen atom or an amino, mono- or di-(lower alkyl)amino, hydroxyl or lower alkoxyl group, X is a hydrogen or halogen atom, Y means a nitrogen atom or a group C-R.sup.4 in which R.sup.4 is a hydrogen or halogen atom or a lower alkyl or lower alkoxyl group or is a group ##STR2## which forms a ring together with R.sup.1 (i.e., the asterisked carbon atoms are linked to the N(1) atom of the quinolone skeleton), and A denotes a specific N-containing group. Preparation processes of the quinolone derivatives and antibacterial agents containing the same are also disclosed.Type: GrantFiled: March 30, 1990Date of Patent: October 6, 1992Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Takashi Yatsunami, Hitodshi Yamamoto, Yasuhiro Kuramoto, Norihiro Hayashi, Akira Yazaki, Satoshi Inoue, Shuichiro Noda, Hirotaka Amano
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Patent number: 5149879Abstract: A lipid peroxidation inhibitor contains a polysulfide compound represented by formula (I) as an active ingredient:R.sup.1 --(S).sub.m --R.sup.2 (I)wherein R.sup.1 and R.sup.2 are same or different hydrocarbon chains having 1 to 16 carbon atoms and m is an integer of 3 to 10. Among compounds (I) are found novel which are:R.sup.3 --(S).sub.n --R.sup.4 (II)wherein R.sup.3 and R.sup.4 are same or different lower alkenyl groups and n is an integer of 6 to 10. Pharmaceutical compositions which contain a polysulfide compound represented by formula (I) as an active ingredient, for preventing and curing diseases of thrombosis, arteiosclerosis, liver troubles, pulmonary edema, skin troubles, eye troubles and aging are also disclosed.Type: GrantFiled: June 21, 1991Date of Patent: September 22, 1992Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Shoji Awazu, Toshiharu Horie, Yukihiro Kodera, Shinji Nagae, Hiromichi Matsuura, Yoichi Itakura
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Patent number: 5093122Abstract: An Allium genus plant, typically garlic is extracted by adding water or alcohol to the garlic, subjecting a mixture of the solvent and the garlic to extraction, and collecting an extract liquid. A composition containing S-allylcysteine in the extract liquid from the garlic is obtained by adding cysteine to the solvent, the mixture of the solvent and the plant under extraction, or the extract liquid collected, and causing the cysteine to convert into S-allylcysteine which is effective controlling hepatopathy and oncogenesis.Type: GrantFiled: November 21, 1990Date of Patent: March 3, 1992Assignee: Wakunaga Seiyaku Kabushiki KaishaInventor: Yukihiro Kodera
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Patent number: 5093505Abstract: Heterocyclic compounds of the general formula: ##STR1## wherein R.sup.11 is a hydroxyl group or a lower alkoxy group, R.sup.12 is a lower alkoxy group, R.sup.13 is a saturated or unsaturated hydrocarbon group, X is an oxygen atom or a sulfur atom, and Y is an oxygen atom or --NH-- which may have a lower alkyl substituent, or salts thereof are novel and effective in controlling carcinoma.Type: GrantFiled: May 25, 1990Date of Patent: March 3, 1992Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Hoyoku Nishino, Yukihiro Kodera, Toshihiko Sumida, Susumu Yoshida, Hiromichi Matsuura, Yoichi Itakura
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Patent number: 5026856Abstract: Isoindoline derivatives represented by the formula (I) and their salts are disclosed. ##STR1## There are many varieties for the compound depending on the types of residues R.sup.1 -R.sup.9 and X. The compounds can be prepared from quinoline derivatives of the formula (II) and an isoindoline derivatives of the formula (III). The compounds of formula (I) and their salts have excellent antibacterial activities against both gram positive and gram negative microorganisms. They can be used as a medicine, an agrichemical, and a food preservative.Type: GrantFiled: May 23, 1989Date of Patent: June 25, 1991Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Takashi Yatsunami, Akira Yazaki, Satoshi Inoue, Hitoshi Yamamoto, Masaharu Yokomoto, Jun Nomiyama, Shuichiro Noda
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Patent number: 4879223Abstract: A protein having nonprotein amino acids can be produced by a method which comprises providing a protein-producing organism with a nutrient containing nonprotein amino acids, cells being cultured to produce the protein in a medium containing the nonprotein amino acids, in which method expression of a gene coding for the protein is induced under conditions in which normal cell growth is suppressed.Type: GrantFiled: April 25, 1988Date of Patent: November 7, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Tatsuo Miyazawa, Shigeyuki Yokoyama, Tetsuo Miyake
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Patent number: 4876335Abstract: A poly-labelled oligonucleotide having a plurality of labels, comprising labels carried on a polylysine and having the polylysine introduced on the extension from 5'- and/or 3'-end through phosphate group is useful as a probe for hybridization.Type: GrantFiled: June 30, 1987Date of Patent: October 24, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Akio Yamane, Tatsuro Kawasoe, Noriko Tsukumo, Kenichi Miyoshi
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Patent number: 4876281Abstract: An antifungal agent comprising as an effective component a polysulfide compound represented by formulaR.sub.1 --S(O).sub.p --R.sub.2 (A)whereinR.sub.1 is CH.sub.3 --, CH.sub.2 .dbd.CHCH.sub.2 -- or C.sub.2 H.sub.5 OCO(CH.sub.2).sub.3 --,p is an integer 1 or 2, andR.sub.2 is --S--CH.sub.2 CH.dbd.CH.sub.2 or --CH.sub.2 CH(H) CH(H)--S.sub.q --S(O).sub.r --R.sub.3in which--CH.sub.2 CH(H) CH(H)-- is --CH.sub.2 CH.sub.2 CH.sub.2 -- or--CH.sub.2 CH.dbd.CH--,q is an integer 0 or 1, r is integer from 0 to 2, and R.sub.3 is selected from the group consisting of alkyl having 1 to 6 carbon atoms, benzyl, --CH.sub.2 CH.dbd.CH.sub.2, --CH.sub.2 CH.dbd.CHCH.sub.3, --(CH.sub.2).sub.3 COOC.sub.2 H.sub.5, and --CH.dbd.CHCH.sub.2 --S--(CH.sub.2).sub.3 COOC.sub.2 H.sub.5,with the proviso that p is 2 when R.sub.1 is CH.sub.2 .dbd.CHCH.sub.2 --, R.sub.2 is --CH.sub.2 CH(H) CH(H)--S.sub.q --S(O).sub.r --R.sub.3, --CH.sub.2 CH(H) CH(H)-- is --CH.sub.2 CH.dbd.CH--, q is 1, r is 0 and R.sub.3 is --CH.sub.2 CH.dbd.CH.sub.2.Type: GrantFiled: September 4, 1987Date of Patent: October 24, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Susumu Yoshida, Shizutoshi Nakagawa, Tsuyoshi Ushiroguchi, Hiromichi Matsuura, Akira Yazaki
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Patent number: 4863902Abstract: Antitumor effect of antitumor agents or treatments is favorably controlled by a growth factor. The growth factor enhances antitumor actions of antitumor agents or treatments including those against which tumor or cancer has acquired resistant, or reduces side effects due to the antitumor agents or treatments. The most typical growth factors include human epidermal growth factor. A lot of tumors or cancers including human ones has been tested and a lot of growth factors has been tested, and the favorable control has been determined.Type: GrantFiled: November 28, 1986Date of Patent: September 5, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Harunobu Amagase, Masato Arakawa, Ken Hashimoto
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Patent number: 4849336Abstract: Biotin- or 2,4-dinitrophenyl-oligodeoxyribonucleotide derivative represented by the formula shown below and its preparation method is disclosed: ##STR1## wherein: R is ##STR2## m and n are each 0 or a natural number; R.sup.1 is a straight or branched hydrocarbon residue; and B is a base constituting the nucleotide (in which when a plural number of B exist, they may be either identical or different). This compound is useful for use as a nonradioactive affinity probe for nucleic acid or a primer.Type: GrantFiled: April 25, 1986Date of Patent: July 18, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Kenichi Miyoshi, Masanori Suzuki, Toru Fuwa
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Patent number: 4820812Abstract: An oligonucleotide derivative having an amino group protected with an eliminatable group bonded through a phosphate group and a spacer with an appropriate length to the 5'-end of an oligonucleotide protected suitably at the 3'-hydroxyl group and the base moiety of the nucleotide, and an immobilized oligonucleotide derivative having a Sepharose carrier bonded to the amino group in place of said protective group are disclosed. Methods for production of these derivatives are also disclosed.Type: GrantFiled: February 20, 1987Date of Patent: April 11, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Kenichi Miyoshi, Toru Fuwa
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Patent number: 4818623Abstract: A slide glass comprising a slide glass structure having a glass surface with silicic acid groups and a lipophilic functional group introduced into at least a part of said silicic acid groups. By the lipophilic group thus introduced, peel-off of the cell specimen does not readily occur.Type: GrantFiled: November 28, 1986Date of Patent: April 4, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Toyoharu Hozumi, Yoshihiro Ohshita
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Patent number: 4816569Abstract: A nucleotide of the formula [IV] shown below: ##STR1## wherein: X is hydrogen or --CO--(CH.sub.2).sub.n --CO--R.sup.3 ; each of m and n is an integer up to 20; R.sup.0 is a protective group of a phosphoric acid group, R.sup.1 is hydrogen or a protective group for a 5'-hydroxyl group, R.sup.2 is hydrogen or a protective group for an amino group, R.sup.3 is a carrier having an amino group as the functional group and bound at this functional group in this compound, Y is oxygen atom (--0--) or an imino group (--NH--). This nucleotide, when the X is --CO--(CH.sub.2).sub.n --CO--R.sup.3, has a carrier (R.sup.3) through a spacer (--CO--(CH.sub.2).sub.m --CO--) on extension from the amino group of deoxycytidine and therefore can be used as the starting material, namely the resin, for synthesizing a 3'-aminated oligonucleotide according to the solid phase method.Type: GrantFiled: October 30, 1985Date of Patent: March 28, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventor: Kenichi Miyoshi
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Patent number: 4816481Abstract: Disclosed herein is a cerebral-circulation-metabolism-function-improving agent which contains a 2,6-diphenyl-3,7-dioxabicyclo[3.3.0]octane derivative represented by the following formula as the effective ingredient: ##STR1## wherein, each of R.sub.1, R.sub.3, R.sub.4 and R.sub.6 represents a hydrogen atom or a lower alkoxyl group; each of R.sub.2 and R.sub.5 represents a hydrogen atom, a .beta.-D-glucosyl group or a hydroxyl group; and each of R.sub.7 and R.sub.8 represents an oxygen atom or two hydrogen atoms.Type: GrantFiled: July 21, 1987Date of Patent: March 28, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Naoyuki Takasugi, Mitsuyasu Ushijima, Satoshi Inoue, Terukage Hirata
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Patent number: 4810422Abstract: A bile acid derivative of the following formula (I): ##STR1## wherein: X is a halogen atom; R.sub.1 is a hydrogen atom or a lower alkyl group; Y is ##STR2## (wherein n is an integer of from 0 to 5); each of R.sub.2 and R.sub.3 is a hydrogen atom or a hydroxyl group; R.sub.4 is a hydroxyl group, lower alkoxyl group, ##STR3## (wherein R.sub.5 is a hydrogen atom or a lower alkoxy group, R.sub.6 is a carboxyl group, benzyloxycarbonyl group or sulfonyl group, or a salt thereof, and m is an integer of from 1 to 4); the intermittent line, . . . , is an .alpha.-bond; and the wavy line, , is an .alpha.- or .beta.-bond, and a salt thereof, and a process for production thereof.This bile acid derivative has carcinostatic activity and yet is of low toxicity. Accordingly, this compound can be used as a carcinostatic agent.Type: GrantFiled: September 1, 1987Date of Patent: March 7, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Shunsou Hatono, Akira Yazaki, Masaharu Yokomoto, Yuzo Hirao