DE69924740T2 - Klare wässrige lösungen enthaltend gallensäuren - Google Patents
Klare wässrige lösungen enthaltend gallensäuren Download PDFInfo
- Publication number
- DE69924740T2 DE69924740T2 DE69924740T DE69924740T DE69924740T2 DE 69924740 T2 DE69924740 T2 DE 69924740T2 DE 69924740 T DE69924740 T DE 69924740T DE 69924740 T DE69924740 T DE 69924740T DE 69924740 T2 DE69924740 T2 DE 69924740T2
- Authority
- DE
- Germany
- Prior art keywords
- aqueous solution
- solution according
- acid
- bile
- soluble
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000002253 acid Substances 0.000 title claims description 19
- 150000007513 acids Chemical class 0.000 title claims description 6
- 239000003613 bile acid Substances 0.000 claims abstract description 109
- 239000000243 solution Substances 0.000 claims abstract description 88
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims abstract description 70
- 239000007864 aqueous solution Substances 0.000 claims abstract description 57
- 229920002472 Starch Polymers 0.000 claims abstract description 34
- 235000019698 starch Nutrition 0.000 claims abstract description 34
- 239000008107 starch Substances 0.000 claims abstract description 34
- 239000012084 conversion product Substances 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 8
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- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[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)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 claims description 74
- 229960001661 ursodiol Drugs 0.000 claims description 70
- 229920002774 Maltodextrin Polymers 0.000 claims description 27
- 239000005913 Maltodextrin Substances 0.000 claims description 27
- 229940035034 maltodextrin Drugs 0.000 claims description 27
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[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)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 20
- 238000010521 absorption reaction Methods 0.000 claims description 17
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 16
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 13
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- 150000003839 salts Chemical class 0.000 claims description 12
- -1 cetrizine-2HCl Chemical compound 0.000 claims description 11
- 210000000936 intestine Anatomy 0.000 claims description 11
- 229920002307 Dextran Polymers 0.000 claims description 10
- 210000002784 stomach Anatomy 0.000 claims description 9
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 8
- 102000004877 Insulin Human genes 0.000 claims description 8
- 108090001061 Insulin Proteins 0.000 claims description 8
- 210000000941 bile Anatomy 0.000 claims description 8
- 229960002897 heparin Drugs 0.000 claims description 8
- 229920000669 heparin Polymers 0.000 claims description 8
- 229940125396 insulin Drugs 0.000 claims description 8
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic 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)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 claims description 7
- 229960003080 taurine Drugs 0.000 claims description 7
- 239000004375 Dextrin Substances 0.000 claims description 6
- 229920001353 Dextrin Polymers 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 235000019425 dextrin Nutrition 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 230000036961 partial effect Effects 0.000 claims description 6
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 claims description 4
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- 229960003805 amantadine Drugs 0.000 claims description 4
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 4
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- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 4
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- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 2
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Landscapes
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| US7303768B2 (en) * | 1998-07-24 | 2007-12-04 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
| US20050158408A1 (en) * | 1998-07-24 | 2005-07-21 | Yoo Seo H. | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof |
| US20070072828A1 (en) * | 1998-07-24 | 2007-03-29 | Yoo Seo H | Bile preparations for colorectal disorders |
| US7772220B2 (en) * | 2004-10-15 | 2010-08-10 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| DE19834814A1 (de) * | 1998-08-01 | 2000-02-03 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen mit einem wirksamen Gehalt an Gallensäuren, ihren Salzen und/oder ihren Derivaten |
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| GB2355009A (en) * | 1999-07-30 | 2001-04-11 | Univ Glasgow | Peptides conjugated to bile acids/salts |
| AU2006203315B2 (en) * | 2000-02-04 | 2008-08-28 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
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| DE60028339T2 (de) * | 2000-04-20 | 2007-05-10 | Bioprogress S.P.A. | Verfahren zur Herstellung ursodeoxycholsäure enthaltender pharmazeutischer Zusammensetzungen in flüssiger Form |
| FR2809310B1 (fr) * | 2000-05-26 | 2004-02-13 | Centre Nat Rech Scient | Utilisation de derives de biguanide pour fabriquer un medicament ayant un effet cicatrisant |
| KR100368936B1 (ko) * | 2000-10-04 | 2003-01-24 | 주식회사 대웅 | 우루소데옥시콜린산을 함유한 환경호르몬 독성의 예방 및치료제 |
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| US20080026077A1 (en) * | 2002-11-12 | 2008-01-31 | John Hilfinger | Methods and compositions of gene delivery agents for systemic and local therapy |
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| ES2660172T3 (es) * | 2004-05-19 | 2018-03-21 | Los Angeles Biomedical Research Institute At Harbor-Ucla Medical Center | Composición inyectable que comprende desoxicolato de sodio |
| 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 |
| US7906137B2 (en) * | 2004-05-21 | 2011-03-15 | Mediplex Corporation, Korea | Delivery agents for enhancing mucosal absorption of therapeutic agents |
| CN101035541B (zh) * | 2004-08-30 | 2012-05-30 | 柳署弘 | 溶解的udca在局灶缺血模型中的神经保护作用 |
| AU2005295541B2 (en) | 2004-10-15 | 2011-02-17 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| CN101048164B (zh) * | 2004-11-01 | 2012-05-09 | 柳署弘 | 降低肌萎缩性侧索硬化中神经变性的组合物 |
| DE602005025391D1 (de) * | 2004-11-01 | 2011-01-27 | Seo Hong Yoo | Verfahren und zusammensetzungen zur verringerung der neurodegeneration bei amyotrophischer lateralsklerose |
| SI2730277T1 (sl) | 2004-12-22 | 2020-07-31 | Nitto Denko Corporation | Nosilec zdravila in komplet za nosilec zdravila za zaviranje fibroze |
| US20120269886A1 (en) | 2004-12-22 | 2012-10-25 | Nitto Denko Corporation | Therapeutic agent for pulmonary fibrosis |
| US9572886B2 (en) | 2005-12-22 | 2017-02-21 | Nitto Denko Corporation | Agent for treating myelofibrosis |
| CN101023940A (zh) * | 2006-02-20 | 2007-08-29 | 郝守祝 | 一种紫杉烷类化合物的药用组合物、制备方法及用途 |
| CN101547699A (zh) * | 2006-09-15 | 2009-09-30 | 柳署弘 | 用于结肠直肠病症的胆汁制剂 |
| TWI407971B (zh) | 2007-03-30 | 2013-09-11 | Nitto Denko Corp | Cancer cells and tumor-related fibroblasts |
| ITMI20071573A1 (it) * | 2007-07-31 | 2009-02-01 | Acraf | Composizione farmaceutica liquida stabile a base di trazodone |
| WO2009036368A2 (en) | 2007-09-14 | 2009-03-19 | Nitto Denko Corporation | Drug carriers |
| US9295677B2 (en) | 2008-02-26 | 2016-03-29 | Qing Bile Therapeutics Inc. | Polyhydroxylated bile acids for treatment of biliary disorders |
| US20100021538A1 (en) * | 2008-02-29 | 2010-01-28 | Youngro Byun | Pharmaceutical compositions containing heparin derivatives |
| US8101593B2 (en) | 2009-03-03 | 2012-01-24 | Kythera Biopharmaceuticals, Inc. | Formulations of deoxycholic acid and salts thereof |
| 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 |
| SG178562A1 (en) * | 2009-08-25 | 2012-03-29 | Victor Ling | Polyhydroxylated bile acids for treatment of biliary disorders |
| WO2012112940A1 (en) | 2011-02-18 | 2012-08-23 | Kythera Biopharmaceuticals, Inc. | Treatment of submental fat |
| US8653058B2 (en) | 2011-04-05 | 2014-02-18 | Kythera Biopharmaceuticals, Inc. | Compositions comprising deoxycholic acid and salts thereof suitable for use in treating fat deposits |
| MY184277A (en) * | 2011-08-23 | 2021-03-30 | Kythera Biopharmaceuticals Inc | Formulations of deoxyccholic acid and salts thereof |
| CN104039327B (zh) | 2012-01-06 | 2017-02-15 | 大熊制药株式会社 | 含有牛磺熊去氧胆酸的组合物 |
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| KR20180036580A (ko) * | 2016-09-30 | 2018-04-09 | 주식회사 유스바이오팜 | 수가용화(水加溶化)된 우르소데옥시콜산을 함유하는 염증성 피부질환 또는 중증 소양증 예방 또는 치료용 조성물 |
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-
1999
- 1999-07-20 AU AU50819/99A patent/AU758679B2/en not_active Ceased
- 1999-07-20 JP JP2000560868A patent/JP4790123B2/ja not_active Expired - Fee Related
- 1999-07-20 RU RU2001105906/15A patent/RU2224523C2/ru not_active IP Right Cessation
- 1999-07-20 US US09/357,549 patent/US6251428B1/en not_active Expired - Fee Related
- 1999-07-20 EP EP99935313A patent/EP1113785B1/en not_active Expired - Lifetime
- 1999-07-20 KR KR10-2001-7001037A patent/KR100524358B1/ko not_active Expired - Lifetime
- 1999-07-20 ID IDW20010199D patent/ID29632A/id unknown
- 1999-07-20 WO PCT/US1999/012840 patent/WO2000004875A2/en not_active Ceased
- 1999-07-20 PT PT99935313T patent/PT1113785E/pt unknown
- 1999-07-20 AT AT99935313T patent/ATE292956T1/de active
- 1999-07-20 ES ES99935313T patent/ES2238843T3/es not_active Expired - Lifetime
- 1999-07-20 IL IL14098699A patent/IL140986A0/xx active IP Right Grant
- 1999-07-20 DE DE69924740T patent/DE69924740T2/de not_active Expired - Lifetime
- 1999-07-20 CN CNB998101478A patent/CN1205922C/zh not_active Expired - Fee Related
- 1999-07-20 BR BR9912395-9A patent/BR9912395A/pt not_active Application Discontinuation
- 1999-07-20 CA CA002338457A patent/CA2338457C/en not_active Expired - Fee Related
-
2001
- 2001-01-18 IL IL140986A patent/IL140986A/en not_active IP Right Cessation
-
2010
- 2010-10-18 JP JP2010233252A patent/JP2011021031A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000004875A2 (en) | 2000-02-03 |
| JP2002522357A (ja) | 2002-07-23 |
| AU758679B2 (en) | 2003-03-27 |
| KR100524358B1 (ko) | 2005-10-26 |
| RU2224523C2 (ru) | 2004-02-27 |
| CA2338457A1 (en) | 2000-02-03 |
| ATE292956T1 (de) | 2005-04-15 |
| CN1348360A (zh) | 2002-05-08 |
| AU5081999A (en) | 2000-02-14 |
| PT1113785E (pt) | 2005-08-31 |
| EP1113785B1 (en) | 2005-04-13 |
| JP4790123B2 (ja) | 2011-10-12 |
| ES2238843T3 (es) | 2005-09-01 |
| BR9912395A (pt) | 2001-10-16 |
| EP1113785A2 (en) | 2001-07-11 |
| US6251428B1 (en) | 2001-06-26 |
| CN1205922C (zh) | 2005-06-15 |
| WO2000004875A3 (en) | 2001-05-03 |
| CA2338457C (en) | 2009-11-17 |
| JP2011021031A (ja) | 2011-02-03 |
| IL140986A (en) | 2006-08-01 |
| IL140986A0 (en) | 2002-02-10 |
| ID29632A (id) | 2001-09-06 |
| DE69924740D1 (de) | 2005-05-19 |
| KR20010074748A (ko) | 2001-08-09 |
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