JP5919597B2 - デオキシコール酸およびその塩類の製剤 - Google Patents
デオキシコール酸およびその塩類の製剤 Download PDFInfo
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- JP5919597B2 JP5919597B2 JP2014527128A JP2014527128A JP5919597B2 JP 5919597 B2 JP5919597 B2 JP 5919597B2 JP 2014527128 A JP2014527128 A JP 2014527128A JP 2014527128 A JP2014527128 A JP 2014527128A JP 5919597 B2 JP5919597 B2 JP 5919597B2
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- salt
- sodium
- deoxycholic acid
- formulation
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- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 title claims description 119
- 239000000203 mixture Substances 0.000 title claims description 115
- 229960003964 deoxycholic acid Drugs 0.000 title claims description 101
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 title claims description 71
- 150000003839 salts Chemical class 0.000 title claims description 39
- 238000009472 formulation Methods 0.000 title description 32
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 78
- 238000001556 precipitation Methods 0.000 claims description 35
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000007864 aqueous solution Substances 0.000 claims description 26
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 26
- 239000000872 buffer Substances 0.000 claims description 20
- 239000011780 sodium chloride Substances 0.000 claims description 16
- 210000001789 adipocyte Anatomy 0.000 claims description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 238000010254 subcutaneous injection Methods 0.000 claims description 10
- 239000007929 subcutaneous injection Substances 0.000 claims description 10
- -1 alkali metal salt Chemical class 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 230000002335 preservative effect Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 5
- 239000008223 sterile water Substances 0.000 claims description 4
- 230000002934 lysing effect Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000009089 cytolysis Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 238000000034 method Methods 0.000 description 32
- 239000002585 base Substances 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 23
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- 150000001875 compounds Chemical class 0.000 description 15
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 229940009976 deoxycholate Drugs 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 101710151321 Melanostatin Proteins 0.000 description 11
- 102400000064 Neuropeptide Y Human genes 0.000 description 11
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- 229910052751 metal Inorganic materials 0.000 description 10
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- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000002464 receptor antagonist Substances 0.000 description 8
- 229940044551 receptor antagonist Drugs 0.000 description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 239000005557 antagonist Substances 0.000 description 5
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- 125000006239 protecting group Chemical group 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 4
- 230000002421 anti-septic effect Effects 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 235000010216 calcium carbonate Nutrition 0.000 description 4
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 4
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 4
- 239000001095 magnesium carbonate Substances 0.000 description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 4
- 235000014380 magnesium carbonate Nutrition 0.000 description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011667 zinc carbonate Substances 0.000 description 4
- 229910000010 zinc carbonate Inorganic materials 0.000 description 4
- 235000004416 zinc carbonate Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 229910000397 disodium phosphate Inorganic materials 0.000 description 3
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- 150000002632 lipids Chemical class 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
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- 239000008215 water for injection Substances 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- GKKPXBHNFVDHAQ-USNYZCROSA-N (2r)-n-[(2r)-3-[4-[n'-[[4-[(dimethylamino)methyl]cyclohexyl]methyl]carbamimidoyl]phenyl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]-2-(naphthalen-2-ylsulfonylamino)-3-phenylpropanamide Chemical compound C1CC(CN(C)C)CCC1CN=C(N)C(C=C1)=CC=C1C[C@H](C(=O)N1CCCC1)NC(=O)[C@H](NS(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CC1=CC=CC=C1 GKKPXBHNFVDHAQ-USNYZCROSA-N 0.000 description 2
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- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
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| PCT/US2011/048806 WO2013028177A1 (en) | 2011-08-23 | 2011-08-23 | Formulations of deoxycholic acid and salts thereof |
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| JP2016055666A Division JP6219430B2 (ja) | 2016-03-18 | 2016-03-18 | デオキシコール酸およびその塩類の製剤 |
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| JP (1) | JP5919597B2 (ko) |
| KR (5) | KR20200013103A (ko) |
| CN (3) | CN108619089A (ko) |
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| BR (1) | BR112014000547B1 (ko) |
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| US8101593B2 (en) | 2009-03-03 | 2012-01-24 | Kythera Biopharmaceuticals, Inc. | Formulations of deoxycholic acid and salts thereof |
| KR20180100309A (ko) * | 2015-11-04 | 2018-09-10 | 키쎄라 바이오파마슈티컬즈 인코포레이티드 | 데옥시콜산 및 이의 염을 사용한 축적된 지방의 치료 방법 |
| US20180078621A1 (en) * | 2016-09-22 | 2018-03-22 | Kyoung Lack Lee | Composition for hypotonic lipolysis and manufacturing method thereof |
| KR101841193B1 (ko) * | 2016-09-22 | 2018-03-22 | 이경락 | 저장성 지방 분해 조성물 및 그의 제조 방법 |
| US20190314388A1 (en) * | 2018-04-16 | 2019-10-17 | Penmix Ltd. | Pharmaceutical composition containing deoxycholic acid |
| KR102172439B1 (ko) | 2018-12-05 | 2020-10-30 | 송미희 | 지방 분해용 조성물 및 이를 포함하는 주사제 조성물 |
| KR102064864B1 (ko) | 2019-02-08 | 2020-01-10 | (주)제테마 | 국소 주사용 조성물 |
| KR102111346B1 (ko) * | 2019-08-20 | 2020-05-22 | 아영창 | 침전으로부터 안정한 소듐디옥시콜레이트를 포함하는 수용액상 조성물 |
| KR20220026068A (ko) | 2020-08-25 | 2022-03-04 | 강명범 | 지방 분해용 주사제 조성물 |
| CN116617160A (zh) * | 2023-07-25 | 2023-08-22 | 山东则正医药技术有限公司 | 水性混悬液及制备方法、冻干粉及应用、脂肪消减注射剂 |
| CN118005707A (zh) * | 2024-01-18 | 2024-05-10 | 山东省食品药品检验研究院 | 一种脱氧胆酸钠晶型a及其制备方法和应用 |
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| FR2754709B1 (fr) | 1996-10-23 | 1999-03-05 | Sanofi Sa | Composition cosmetique contenant un antagoniste des recepteurs du neuropeptide gamma et alpha 2 antagonistes susceptibles d'etre incorpores dans une telle composition |
| EP1113785B1 (en) * | 1998-07-24 | 2005-04-13 | Seo Hong Yoo | Clear aqueous solutions of bile acids |
| US6417179B1 (en) * | 1998-10-13 | 2002-07-09 | Craig G. Burkhart | Ear wax solution |
| US20050048126A1 (en) * | 2000-12-22 | 2005-03-03 | Barrett Rabinow | Formulation to render an antimicrobial drug potent against organisms normally considered to be resistant to the drug |
| DE10361067A1 (de) * | 2003-12-22 | 2005-07-14 | Aventis Pharma Deutschland Gmbh | Medikamentöse Lipolyse von Fettansammlungen |
| US7754230B2 (en) * | 2004-05-19 | 2010-07-13 | The Regents Of The University Of California | Methods and related compositions for reduction of fat |
| US20060127468A1 (en) * | 2004-05-19 | 2006-06-15 | Kolodney Michael S | Methods and related compositions for reduction of fat and skin tightening |
| ATE521355T1 (de) * | 2004-05-19 | 2011-09-15 | Los Angeles Biomed Res Inst | Verwendung eines detergens zur nicht- chirurgischen entfernung von fett |
| US20090317376A1 (en) | 2005-06-06 | 2009-12-24 | Georgetown University Medical School | Compositions And Methods For Lipo Modeling |
| TW201011755A (en) | 2008-09-10 | 2010-03-16 | Skymedi Corp | Flash memory system and its data recovery method |
| JP5420946B2 (ja) * | 2009-03-23 | 2014-02-19 | 富士フイルム株式会社 | 胆汁酸を含むミノキシジル水性組成物 |
| EP2645099A1 (en) | 2012-03-30 | 2013-10-02 | Phares Pharmaceutical Research N.V. | Biorelevant compositions |
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- 2011-08-23 CA CA2842177A patent/CA2842177C/en active Active
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