Patents Assigned to Drug Delivery System Institute, Ltd.
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Patent number: 6838450Abstract: A drug complex characterized in that a residue of a drug compound such as antineoplastic agents and a carboxy(C1-4)alkyldextran polyalcohol obtained by treating a dextran under conditions that enable substantially complete polyalcoholization are bound to each other by means of a spacer comprising an amino acid or a spacer comprising peptide-bonded 2 to 8 amino acids. Said complex is characterized in that it has excellent selectivity to tumorous sites so as to exhibit high antineoplastic activity and also achieves reduced appearance of toxicity.Type: GrantFiled: May 28, 2002Date of Patent: January 4, 2005Assignees: Daiichi Pharmaceutical Co., LTD, Drug Delivery System Institute, Ltd.Inventors: Kazuhiro Inoue, Hiroshi Susaki, Masahiro Ikeda, Hiroshi Kuga, Eiji Kumazawa, Akiko Togo
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Patent number: 6436912Abstract: A drug complex characterized in that a residue of a drug compound such as antineoplastic agents and a carboxy(C1-4)alkyldextran polyalcohol obtained by treating a dextran under conditions that enable substantially complete polyalcoholization are bound to each other by means of a spacer comprising an amino acid or a spacer comprising peptide-bonded 2 to 8 amino acids. Said complex is characterized-in that it has excellent selectivity to tumorous sites so as to exhibit high antineoplastic activity and also achieves reduced appearance of toxicity.Type: GrantFiled: March 25, 1999Date of Patent: August 20, 2002Assignees: Daiichi Pharmaceutical Co., Ltd., Drug Delivery System Institute, Ltd.Inventors: Kazuhiro Inoue, Hiroshi Susaki, Masahiro Ikeda, Hiroshi Kuga, Eiji Kumazawa, Akiko Togo
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Patent number: 6322996Abstract: Transglutaminase is allowed to act upon both a physiologically active protein (inclusive of a fused protein thereof with a peptide through acid amide bonding) and an amino group donor containing the polyethylene glycol, polysaccharide, polyamino acid or branched type sugar derivative moiety, whereby the physiologically active protein is modified without spoiling its inherent physiological activities, and may be improved in its qualification as a drug.Type: GrantFiled: November 29, 1995Date of Patent: November 27, 2001Assignee: Drug Delivery System Institute, Ltd.Inventors: Haruya Sato, Keiji Yamamoto, Kokichi Suzuki, Masahiro Ikeda, Masahiro Sakagami, Makoto Taniguchi
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Patent number: 6057431Abstract: The present invention provides a compound of general formula (I): ##STR1## wherein X represents group (II) or (III): ##STR2## wherein Y represents a leaving group and Z represents an oligonucleotide. The compound can specifically transfer oligonucleotides to cells which specifically recognize a specified saccharide construction. Accordingly, the compound can be used as an antiviral agent or an antitumor agent.Type: GrantFiled: December 22, 1997Date of Patent: May 2, 2000Assignee: Drug Delivery System Institute, Ltd.Inventors: Hiroshi Ishihara, Takayuki Kawaguchi, Masahiro Ikeda, Kazutaka Nakamoto, Atsushi Sasaki
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Patent number: 6013526Abstract: The present invention relates to a process for producing a conjugate of a biologically active peptide or protein having at least one glutamine residue with a high-molecular weight substance containing an amino group. The present invention also relates to a composite of this conjugate with a nucleic acid adsorbed thereto for transferring nucleic acids to mammalian cells.Type: GrantFiled: September 10, 1997Date of Patent: January 11, 2000Assignees: Ajinomoto Co., Inc., Drug Delivery System Institute, Ltd.Inventors: Yoshiyuki Takahara, Naoyuki Yamada, Masao Motoki
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Patent number: 6010871Abstract: A process for modifying a physiologically active peptide or a physiologically active protein which comprises reacting a physiologically active peptide or a physiologically active protein having at least a glutamine residue with a substance having an amino donor in the presence of a transglutaminase originating in a microorganism to thereby form an acid amide bond at the .gamma.-position acid amide group of the glutamine residue with the amino group of the amino donor; and the product of modification obtained thereby.Type: GrantFiled: September 8, 1997Date of Patent: January 4, 2000Assignees: Ajinomoto Co., Inc., Drug Delivery System Institute, Ltd.Inventors: Yoshiyuki Takahara, Naoyuki Yamada, Masao Motoki
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Patent number: 5863907Abstract: A carboxymethylmannoglucan comprising tetrasaccharide units represented by the following general formula (I) and salt thereof. Further, the invention discloses a carboxymethylmannoglucan derivative and salt thereof produced by subjecting part or the whole of mannose of the tetrasaccharide units to ring opening and subjecting part or the whole of glucose which constitute the main chain but have no mannose as a branch ##STR1## wherein R.sup.1 to R.sup.12 each represent a hydrogen atom or a carboxymethyl group.The compounds are useful as carrier for delaying the disappearance of a drug in the blood and for enhancing the organotropism of the drug for a carcinoma.Type: GrantFiled: July 30, 1996Date of Patent: January 26, 1999Assignee: Drug Delivery System Institute, Ltd.Inventors: Kazuhiro Inoue, Teruomi Ito, Takayuki Kawaguchi, Katsutoshi Aono, Satoshi Okuno, Toshiro Yano
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Patent number: 5863908Abstract: A carboxymethylmannoglucan comprising tetrasaccharide units represented by the following general formula (I) and salt thereof. Further, the invention discloses a carboxymethylmannoglucan derivative and salt thereof produced by subjecting part or the whole of mannose of the tetrasaccharide units to ring opening and subjecting part or the whole of glucose which constitute the main chain but have no mannose as a branch ##STR1## wherein R.sup.1 to R.sup.12 each represent a hydrogen atom or a carboxymethyl group.The compounds are useful as carrier for delaying the disappearance of a drug in the blood and for enhancing the organotropism of the drug for a carcinoma.Type: GrantFiled: July 30, 1996Date of Patent: January 26, 1999Assignee: Drug Delivery System Institute, Ltd.Inventors: Kazuhiro Inoue, Teruomi Ito, Takayuki Kawaguchi, Katsutoshi Aono, Satoshi Okuno, Toshiro Yano
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Patent number: 5688931Abstract: A novel polysaccharide derivative, a drug carrier comprising a novel polysaccharide derivative, and a drug complex are disclosed. The polysaccharide derivative according to the present invention comprises a polysaccharide having a carboxyl group in which a peptide chain is introduced at a part or all of the carboxyl groups of the polysaccharide. The peptide chain comprises 1-8 amino acids which may be the same or different. A part or all of the amino groups in the peptide chain which are not involved in the linkages with the carboxyl groups of the polysaccharide or the carboxyl groups in the peptide chain may form an acid amide linkage or an ester linkage with a carboxyl group, an amino group or a hydroxyl group of a third compound such as drugs. The polysaccharide derivative has a property of accumulating in a high amount at a tumor, and thus can deliver efficiently a drug which has a side-effect or a limited sustainment of the drug efficacy to the tumor.Type: GrantFiled: December 28, 1994Date of Patent: November 18, 1997Assignee: Drug Delivery System Institute, Ltd.Inventors: Hideo Nogusa, Hiroshi Hamana, Toshiro Yano, Masahiro Kajiki, Keiji Yamamoto, Satoshi Okuno, Shuichi Sugawara, Nobukazu Kashima, Kazuhiro Inoue
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Patent number: 5580904Abstract: According to the present invention, a novel compound group which can pass through blood-brain barrier (BBB) with carrying a drug thereon and stay within brain to release the drug and a well-known compound group having the properties described above are provided.The compound represented by the general formula ##STR1## wherein, R.sup.1 represents C.sub.1-6 alkyl which may be substituted by a group selected from hydroxyl, carboxyl, amino group which may be substituted by C.sub.1-6 alkyl, and a five- to seven-membered saturated heterocyclic ring,R.sup.2 represents hydrogen or C.sub.1-6 alkyl,R.sup.3 represents hydrogen or C.sub.1-6 alkyl which may be substituted by hydroxyl,R.sup.4 represents hydrogen or C.sub.1-6 alkyl,R.sup.5 represents an amino acid residue, or --S--R.sup.6 or --CO--R.sup.6 wherein R.sup.6 represents C.sub.1-14 alkyl which may be substituted by a five- to seven-membered saturated ring; C.sub.Type: GrantFiled: June 24, 1994Date of Patent: December 3, 1996Assignee: Drug Delivery System Institute, Ltd.Inventors: Toyoaki Ishikura, Teruomi Ito, Takashi Kato, Kazutoshi Horie, Hiroshi Ishihara, Takashi Senou
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Patent number: 5567690Abstract: A carboxymethylmannoglucan comprising tetrasaccharide units represented by the following general formula (I) and salt thereof. Further, the invention discloses a carboxymethylmannoglucan derivative and salt thereof produced by subjecting part or the whole of mannose of the tetrasaccharide units to ring opening and subjecting part or the whole of glucose which constitute the main chain but have no mannose as a branch ##STR1## wherein R.sup.1 to R.sup.12 each represent a hydrogen atom or a carboxymethyl group.The compounds are useful as carrier for delaying the disappearance of a drug in the blood and for enhancing the organotropism of the drug for a carcinoma.Type: GrantFiled: March 2, 1995Date of Patent: October 22, 1996Assignee: Drug Delivery System Institute, Ltd.Inventors: Kazuhiro Inoue, Teruomi Ito, Takayuki Kawaguchi, Katsutoshi Aono, Satoshi Okuno, Toshiro Yano
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Patent number: 5463022Abstract: N-acetylcarboxymethylchitosan derivatives are provided by the present invention. They are represented by the following formula (I): ##STR1## wherein R.sub.1 and R.sub.2 individually mean H or carboxymethyl group; P denotes a group R.sub.3 CO--, a group R.sub.4 NH-- or a group R.sub.5 O-- with assuming that R.sub.3 COOH denotes a compound having carboxyl group, R.sub.4 NH.sub.2 denotes a compound having amino group and R.sub.5 OH denotes an alcohol compound; Q stands for H or a group --OH; X represents a peptide chain containing same or different, one to ten amino acids; a.sub.1 and a.sub.2 individually represent zero or a positive integer, provided that both of a.sub.1 and a.sub.2 are not zero at the same time, and b stands for a positive integer; and having the following characteristic values (1)-(4):______________________________________ (1) carboxymethylation degree: 0.5-1.2 (2) molecular weight (as measured 3,000-300,000 by gel filtration method): (3) a/(a + b): 0.01-1 [provided that a = a.sub.1 + a.sub.Type: GrantFiled: February 16, 1993Date of Patent: October 31, 1995Assignee: Drug Delivery System Institute, Ltd.Inventors: Kazuhiro Inoue, Teruomi Ito, Satoshi Okuno, Katsutoshi Aono
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Patent number: 5243035Abstract: Sialic acid- containing glycolipid derivatives represented by the following general formula, their production method, and the particulate carriers that contain as a constituent the sialic acid-containing glycolipid derivative(s). ##STR1## wherein represents the .alpha.- or the .beta.- linkage, R.sup.1, a hydrogen atom or an acetyl group,R.sup.2, a hydrogen atom, a lower alkyl group with 1-4 carbon atoms, an alkaline metal ion, or such,X, an oxygen or sulfur atom or a residue represented by the following formula (II) or (III),--O(CH.sub.2).sub.m NHCO-- (II)where m represents an integer from 1 to 10.--O(CH.sub.2).sub.m CONH-- (III)Y, the formula (IV). ##STR2## where A represents a linear or branched chain acylamino group with 10-40 carbon atoms, or such B, a hydrogen atom, a carboxyl group or such, or the formula (V), and ##STR3## n, an integer of 0 to 3.Type: GrantFiled: August 15, 1991Date of Patent: September 7, 1993Assignee: Drug Delivery System Institute, Ltd.Inventors: Satoru Nakabayashi, Kunio Higashi, Shiro Miyoshi, Hitoshi Yamauchi