Patents Assigned to LTT Bio-Pharma Co., Ltd.
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Publication number: 20210198199Abstract: To provide a novel therapeutic agent for fibrosis that induces selective cell death of lung fibroblasts and suppresses lung fibrosis without injuring alvocar epithelial cells. A pharmaceutical composition for treating fibrosis, the pharmaceutical composition comprising a compound of formula (I) or formula (II): wherein in formula (I), R1 represents a C1-4 alkyl group optionally substituted with a halogen atom, and l represents an integer of 3 to 6; and in formula (II), n represents an integer of 8 to 12, or a pharmaceutically acceptable salt thereof or a solvate of the compound or the salt thereof.Type: ApplicationFiled: September 26, 2019Publication date: July 1, 2021Applicants: LTT BIO-PHARMA CO., LTD., MUSASHINO UNIVERSITYInventors: Tohru MIZUSHIMA, Ken-ichiro TANAKA
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Patent number: 10155755Abstract: Provided are a quinuclidine derivative of formula (1) and a medicament comprising the quinuclidine derivative: wherein R1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, or a haloalkoxy group; Y represents —C(C?O)—O—, or —CH2O—; m represents an integer of 1 to 5; Z represents an oxygen atom or a sulfur atom; l represents a number of 0 or 1; n represents an integer of 0 to 4; X? represents an anion; and a substituent of a quinuclidine ring represents a 1,3-bond, or 1,4-bond, provided that when m is 3, l is 1, and n is 0, R1 represents a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, or a haloalkoxy group.Type: GrantFiled: February 25, 2016Date of Patent: December 18, 2018Assignee: LTT BIO-PHARMA CO., LTD.Inventors: Tohru Mizushima, Yasunobu Yamashita, Naoki Yamakawa
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Publication number: 20180051018Abstract: Provided is a novel therapeutic agent for chronic obstructive pulmonary disease. Provided are a quinuclidine derivative and a medicament comprising the quinuclidine derivative. wherein R1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, or a haloalkoxy group; Y represents —C(C?O)—O—, —CH2—, or —CH2O—; m represents an integer of 1 to 5; Z represents an oxygen atom or a sulfur atom; l represents a number of 0 or 1; n represents an integer of 0 to 4; X? represents an anion; and a substituent of a quinuclidine ring represents a 1,3-bond, or 1,4-bond, provided that when m is 3, l is 1, and n is 0, R1 represents a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, or a haloalkoxy group.Type: ApplicationFiled: February 25, 2016Publication date: February 22, 2018Applicant: LTT BIO-PHARMA CO., LTD.Inventors: Tohru MIZUSHIMA, Yasunobu YAMASHITA, Naoki YAMAKAWA
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Patent number: 9539248Abstract: This invention provides a safe and effective agent for ameliorating chronic obstructive pulmonary disease (COPD) that has both a bronchodilator effect and an anti-inflammatory effect. The agent for ameliorating chronic obstructive pulmonary disease contains mepenzolate bromide as an active ingredient. More preferably the mode of administration of the agent for ameliorating chronic obstructive pulmonary disease is airway administration or inhalation administration, and furthermore the mode of administration thereof is oral administration or rectal administration. This invention is a safe and effective agent for ameliorating chronic obstructive pulmonary disease (COPD) that has both a bronchodilator effect and an anti-inflammatory effect of mepenzolate bromide.Type: GrantFiled: May 22, 2015Date of Patent: January 10, 2017Assignee: LTT Bio-Pharma Co., Ltd.Inventors: Toru Mizushima, Hongxing Liu
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Patent number: 9221786Abstract: Provided are novel 2-fluorophenyl propionic acid derivatives which have excellent anti-inflammatory/analgesic effects while avoiding side effects such as gastrointestinal disorders, namely 2-fluorophenyl propionic acid derivatives represented by the formula (I) below or pharmaceutically acceptable salts thereof, [wherein, R1 represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group, X represents —CH2—, —NH—, —O—, or —S—, and Y specifically represents group (II) (wherein, Z1 represents —CO—, —CH(OH)—, or —CH2—, and n represents an integer of 1 or 2.Type: GrantFiled: December 6, 2012Date of Patent: December 29, 2015Assignee: LTT Bio-Pharma Co., Ltd.Inventors: Toru Mizushima, Masami Otsuka, Yoshinari Okamoto, Naoki Yamakawa
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Patent number: 9161986Abstract: There is provided a beraprost sodium-containing nanoparticle that contains beraprost sodium among other prostaglandin I2 (prostacyclin) derivatives, which are therapeutic agents for pulmonary hypertension. The beraprost sodium-containing nanoparticle is obtained by making beraprost sodium hydrophobic using a metal ion and allowing the hydrophobic beraprost sodium to react with poly-L-lactic acid or a poly(L-lactic acid/glycolic acid) copolymer, and a poly-DL- or L-lactic acid-polyethylene glycol block copolymer or a poly(DL- or L-lactic acid/glycolic acid)-polyethylene glycol block copolymer. The beraprost sodium-containing nanoparticle excels in sustained release of an active ingredient, reduces a side effect, and furthermore, has an excellent drug retention in the blood. Therefore, the beraprost sodium-containing nanoparticle is quite outstanding particularly regarding the sustainability of the medicinal effect.Type: GrantFiled: February 13, 2012Date of Patent: October 20, 2015Assignee: LTT BIO-PHARMA CO., LTD.Inventors: Toru Mizushima, Tsutomu Ishihara, Hongxing Liu
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Patent number: 8916206Abstract: Drug-containing nanoparticles are provided that enable effective targeting and sustained-release of a water-soluble, non-peptide, low-molecular weight drug and cause reduced accumulation of the drug in the liver. The nanoparticles containing a water-soluble, non-peptide, low-molecular weight drug are obtained by hydrophobicizing the water-soluble, non-peptide, low-molecular weight drug by a metal ion, and reacting the hydrophobicized drug with a poly(lactic acid)-polyethylene glycol block copolymer or a poly(lactic-co-glycolic acid)-polyethylene glycol block copolymer. The nanoparticles have favorable targeting and sustained-release properties and cause reduced accumulation of the drug in the liver.Type: GrantFiled: November 29, 2006Date of Patent: December 23, 2014Assignee: LTT Bio-Pharma Co., Ltd.Inventors: Tsutomu Ishihara, Ayako Mizushima
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Publication number: 20140050690Abstract: There is provided a beraprost sodium-containing nanoparticle that contains beraprost sodium among other prostaglandin I2 (prostacyclin) derivatives, which are therapeutic agents for pulmonary hypertension. The beraprost sodium-containing nanoparticle is obtained by making beraprost sodium hydrophobic using a metal ion and allowing the hydrophobic beraprost sodium to react with poly-L-lactic acid or a poly(L-lactic acid/glycolic acid) copolymer, and a poly-DL- or L-lactic acid-polyethylene glycol block copolymer or a poly(DL- or L-lactic acid/glycolic acid)-polyethylene glycol block copolymer. The beraprost sodium-containing nanoparticle excels in sustained release of an active ingredient, reduces a side effect, and furthermore, has an excellent drug retention in the blood. Therefore, the beraprost sodium-containing nanoparticle is quite outstanding particularly regarding the sustainability of the medicinal effect.Type: ApplicationFiled: February 13, 2012Publication date: February 20, 2014Applicant: LTT Bio-Pharma Co., Ltd.Inventors: Toru Mizushima, Tsutomu Ishihara, Hongxing Liu
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Publication number: 20140023629Abstract: An ameliorating agent for chronic obstructive pulmonary disease (COPD) containing as an active ingredient a lecithinized superoxide dismutase represented by the following general formula (I): SOD?(Q?B)m??(I) (in the formula SOD? represents a residue of the superoxide dismutase; Q represents a chemical crosslinking; B represents a residue without a hydrogen atom of a hydroxyl group of lysolecithin having the hydroxyl group at the 2-position of glycerol; m is the average number of bonds of lysolecithin to one molecule of superoxide dismutase and represents an integer of 1 or more). The ameliorating agent for COPD is intravenously administered or inhalation-administrated.Type: ApplicationFiled: September 20, 2013Publication date: January 23, 2014Applicant: LTT Bio-Pharma Co., Ltd.Inventor: Toru MIZUSHIMA
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Patent number: 8431614Abstract: There is provided a novel loxoprofen derivative that has no side effect such as a gastrointestinal disorder and also has excellent anti-inflammatory and analgesic effects and is represented by the following formula (I) or (II): (wherein R1 and R2 each represent a halogen atom or a substituted or unsubstituted phenyl group) or a pharmacologically acceptable salt thereof. In the derivative, the halogen atom is selected from a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom, and a substituent of the substituted phenyl group is a halogen atom, a hydroxyl group, a substituted or unsubstituted lower alkyl group, a lower alkylthio group, a lower alkoxy group, a nitro group, an amino group, or a carboxyl group.Type: GrantFiled: February 18, 2010Date of Patent: April 30, 2013Assignees: LTT Bio-Pharma Co., Ltd., National University Corporation Kumamoto UniversityInventors: Toru Mizushima, Masami Ohtsuka, Yoshinari Okamoto, Naoki Yamakawa
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Publication number: 20120034202Abstract: An ameliorating agent for chronic obstructive pulmonary disease (COPD) containing as an active ingredient a lecithinized superoxide dismutase represented by the following general formula (I): SOD?(Q-B)m??(I) (in the formula SOD? represents a residue of the superoxide dismutase; Q represents a chemical crosslinking; B represents a residue without a hydrogen atom of a hydroxyl group of lysolecithin having the hydroxyl group at the 2-position of glycerol; m is the average number of bonds of lysolecithin to one molecule of superoxide dismutase and represents an integer of 1 or more). The ameliorating agent for COPD is intravenously administered or inhalation-administrated.Type: ApplicationFiled: March 2, 2010Publication date: February 9, 2012Applicant: LTT Bio-Pharma Co., Ltd.Inventor: Toru Mizushima
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Publication number: 20120016158Abstract: There is provided a novel loxoprofen derivative that has no side effect such as a gastrointestinal disorder and also has excellent anti-inflammatory and analgesic effects and is represented by the following formula (I) or (II): (wherein R1 and R2 each represent a halogen atom or a substituted or unsubstituted phenyl group) or a pharmacologically acceptable salt thereof. In the derivative, the halogen atom is selected from a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom, and a substituent of the substituted phenyl group is a halogen atom, a hydroxyl group, a substituted or unsubstituted lower alkyl group, a lower alkylthio group, a lower alkoxy group, a nitro group, an amino group, or a carboxyl group.Type: ApplicationFiled: February 18, 2010Publication date: January 19, 2012Applicants: LTT BIO-PHARMA CO., LTD., National University Corporation, Kumamoto UniversityInventors: Toru Mizushima, Masami Ohtsuka, Yoshinari Okamoto, Naoki Yamakawa
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Publication number: 20110262548Abstract: A PGE1 derivative is provided which has an excellent sustained, slow-release PGE1 action. In addition, a PGE1-derivative-containing nanoparticle produced using this PGE1 derivative is provided, which effectively targets an affected site, has excellent drug slow-release properties, and has reduced side effects. This PGE1-derivative-containing nanoparticle is a nanoparticle containing a prostaglandin E1 derivative represented by the following formula (1) (wherein n denotes an integer of 1 to 12), obtained by hydrophobicizing the prostaglandin E1 derivative with a metal ion, and reacting the hydrophobicized prostaglandin E1 derivative with poly L-lactic acid or a poly(L-lactic acid/glycolic acid) copolymer and a poly DL- or L-lactic acid-polyethylene glycol block copolymer or a poly(DL- or L-lactic acid/glycolic acid)-polyethylene glycol block copolymer.Type: ApplicationFiled: October 16, 2009Publication date: October 27, 2011Applicant: LTT Bio-Pharma Co., Ltd.Inventors: Toru Mizushima, Masami Ohtsuka, Yoshinari Okamoto
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Publication number: 20110262420Abstract: An inhalant containing a lecithinized superoxide dismutase (hereinafter referred to as PC-SOD) which effectively exerts the effect of superoxide dismutase (SOD) as an active ingredient, particularly for treatment of idiopathic (acute) or chronic interstitial pneumonia, is provided. The inhalant includes a PC-SOD represented by the following general formula (I): SOD?(Q?B)m??(I) (wherein SOD? is a residue of the superoxide dismutase; Q is a chemical crosslinking; B is a residue without a hydrogen atom of a hydroxyl group of lysolecithin having the hydroxyl group at the 2-position of glycerol; and m is the average number of bonds of lysolecithin to one molecule of superoxide dismutase and is an integer of 1 or more).Type: ApplicationFiled: November 9, 2009Publication date: October 27, 2011Applicant: LTT Bio-Pharma Co., Ltd.Inventor: Toru Mizushima
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Publication number: 20100143321Abstract: A therapeutic agent for interstitial pneumonia is provided which effectively exploits the effect of superoxide dismutase (SOD). The therapeutic composition for interstitial pneumonia contains 10 to 100 mg of lecithinized superoxide dismutase represented by the following general formula (I): SOD?(Q-B)m ??(I) (wherein SOD? is a residue of superoxide dismutase; Q is a chemical crosslink; B is a residue of lysolecithin having the hydrogen atom of the hydroxyl group at position 2 of its glycerol moiety removed; and m is the average number of lysolecithin molecules bound to one molecule of the superoxide dismutase and is an integer of 1 or greater) and further contains sucrose to give it a stable form suitable for intravenous administration.Type: ApplicationFiled: December 19, 2007Publication date: June 10, 2010Applicant: LTT BIO PHARMA CO., LTD.Inventors: Kouji Shirai, Tatsuo Kawashima, Toshihisa Kuroda, Yutaka Mizushima, Ayako Mizushima, Masahiro Murakami, Tomoharu Fukuzaki
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Publication number: 20100129456Abstract: A nanoparticle containing a low-molecular-weight drug having a negatively charged group is provided that is effectively targeted to an affected site, is capable of sufficiently sustained release of the drug, and has a reduced tendency to accumulate in the liver to cause reduced side effects. The nanoparticle containing a low-molecular-weight drug having a negatively charged group is obtained by hydrophobicizing the low-molecular-weight drug having a negatively charged group with a metal ion, and reacting the hydrophobicized drug with poly L-lactic acid or poly(L-lactic acid/glycolic acid) copolymer and poly DL- or L-lactic acid-polyethylene glycol block copolymer or poly(DL- or L-lactic acid/glycolic acid)-polyethylene glycol block copolymer.Type: ApplicationFiled: April 11, 2008Publication date: May 27, 2010Applicant: LTT Bio-Pharma Co., Ltd.Inventors: Tsutomu Ishihara, Yutaka Mizushima, Ayako Mizushima, Toru Mizushima
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Patent number: 7700336Abstract: To provide a lecithinized superoxide dismutase (PC-SOD) composition useful as a drug material and a process for its production. The PC-SOD composition contains a PC-SOD obtained by substituting at least amino group in a specific SOD with a lecithin moiety represented by the following formula (I), wherein the PC-SOD contains a PC-SOD (A) having an m number of amino groups substituted with the lecithin moieties (wherein m is an integer of from 1 to 4 and averages from 1.5 to 2.4 as a main component and the PC-SOD (A) consists of a PC-SOD (a1) wherein m=1, a PC-SOD (a2) wherein m=2, a PC-SOD (a3) wherein m=3 and a PC-SOD (a4) wherein m=4.Type: GrantFiled: April 11, 2007Date of Patent: April 20, 2010Assignees: LTT Bio-Pharma Co., Ltd., Beijing Tide Pharmaceutical Co., Ltd.Inventors: Hideo Nomoto, Toshiaki Nakayama, Maki Murahashi, Yoshitomi Morizawa
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Patent number: 7642230Abstract: With a simple and high-yield production method, a zinc-containing sustained-release composition capable of stabilizing a physiologically active protein or peptide, typically G-CSF by precipitation and retaining drug efficacy for several days in a living body owing to its sustained releasability is provided. Concretely, a zinc-containing sustained-release composition produced by forming a precipitate by mixing a physiologically active protein or peptide, a water-soluble zinc salt, a water-soluble carbonate and/or a water soluble phosphate aqueous solution. The zinc-containing sustained-release composition may be administered as a zinc-containing sustained preparation by adding a pharmaceutically acceptable additive as is necessary.Type: GrantFiled: April 1, 2004Date of Patent: January 5, 2010Assignee: LTT Bio-Pharma Co., Ltd.Inventors: Michio Kimura, Tomoko Eto, Yutaka Mizushima
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Publication number: 20080113014Abstract: A method for screening for compounds or salts thereof, in particular nonsteroidal anti-inflammatory compounds or salts thereof, that are safe for gastric mucosa and cause little gastrointestinal side effects. The method uses a particular liposome to serve as a cell membrane model. The liposome encapsulates a fluorescent dye, in particular, calcein and is formed of phospholipids, such as phosphatidylcholine, phosphatidylglycerol, phosphatidylserine, and phosphatidylinositol. A test compound is allowed to react with the liposome and the leakage of the fluorescent dye from the liposome is evaluated. As a result, compounds safe for gastric mucosa, in particular, anti-inflammatory compounds can be screened.Type: ApplicationFiled: December 15, 2004Publication date: May 15, 2008Applicant: LTT BIO-PHARMA CO., LTD.Inventors: Toru Mizushima, Yutaka Mizushima
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Publication number: 20070258926Abstract: A composition contains nanoparticles of retinoic acid as an active ingredient. The nanoparticles have reduced irritancy of retinoic acid and are suitable for subcutaneous or intravenous administration, as well as for use in sustained-release preparation. The high skin permeability of the nanoparticles makes the composition suitable for use in pharmaceutical or non-pharmaceutical external preparations or cosmetics intended for skin application. The retinoic acid nanoparticles of the present invention are coated with an inorganic salt of polyvalent metal and can be dissolved in water to make a stable clear solution that can be formulated into injectable preparations for subcutaneous and intravenous administration. The polyvalent metal inorganic salt coating helps reduce the irritancy of retinoic acid, so that the nanoparticles do not cause inflammation or tumor formation at the site of application. The inorganic salt of polyvalent metal may be calcium carbonate, zinc carbonate or calcium phosphate.Type: ApplicationFiled: October 15, 2003Publication date: November 8, 2007Applicant: LTT BIO-PHARMA CO., LTD.Inventors: Yoko Yamaguchi, Rie Igarashi, Yutaka Mizushima, Mitsuko Takenaga, Natsumi Nakamura