JP4598953B2 - 脂質代謝障害を治療するための胆汁酸と結合したプロパノールアミン誘導体 - Google Patents
脂質代謝障害を治療するための胆汁酸と結合したプロパノールアミン誘導体 Download PDFInfo
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- JP4598953B2 JP4598953B2 JP2000574548A JP2000574548A JP4598953B2 JP 4598953 B2 JP4598953 B2 JP 4598953B2 JP 2000574548 A JP2000574548 A JP 2000574548A JP 2000574548 A JP2000574548 A JP 2000574548A JP 4598953 B2 JP4598953 B2 JP 4598953B2
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- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940099563 lactobionic acid Drugs 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229950003595 mebezonium iodide Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical class [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- YSMODUONRAFBET-WHFBIAKZSA-N threo-5-hydroxy-L-lysine Chemical compound NC[C@@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-WHFBIAKZSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- BJBUEDPLEOHJGE-IMJSIDKUSA-N trans-3-hydroxy-L-proline Chemical compound O[C@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-IMJSIDKUSA-N 0.000 description 1
- CWPAAKNARYMZLM-UHFFFAOYSA-L trimethyl-[4-[[4-(trimethylazaniumyl)cyclohexyl]methyl]cyclohexyl]azanium;diiodide Chemical compound [I-].[I-].C1CC([N+](C)(C)C)CCC1CC1CCC([N+](C)(C)C)CC1 CWPAAKNARYMZLM-UHFFFAOYSA-L 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960001005 tuberculin Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- BHQCQFFYRZLCQQ-UTLSPDKDSA-N ursocholic 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)[C@@H](O)C1 BHQCQFFYRZLCQQ-UTLSPDKDSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Vascular Medicine (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19845403A DE19845403B4 (de) | 1998-10-02 | 1998-10-02 | Mit Gallensäuren verknüpfte Propanolaminderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| DE19845403.1 | 1998-10-02 | ||
| PCT/EP1999/006930 WO2000020437A1 (de) | 1998-10-02 | 1999-09-18 | Mit gallensäuren verknüpfte propanolaminderivate zur behandlung von lipidstoffwechselstörungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002526550A JP2002526550A (ja) | 2002-08-20 |
| JP2002526550A5 JP2002526550A5 (https=) | 2006-09-07 |
| JP4598953B2 true JP4598953B2 (ja) | 2010-12-15 |
Family
ID=7883185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000574548A Expired - Fee Related JP4598953B2 (ja) | 1998-10-02 | 1999-09-18 | 脂質代謝障害を治療するための胆汁酸と結合したプロパノールアミン誘導体 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6180618B1 (https=) |
| EP (1) | EP1117676B1 (https=) |
| JP (1) | JP4598953B2 (https=) |
| KR (1) | KR20010075511A (https=) |
| CN (1) | CN1227259C (https=) |
| AR (1) | AR035003A1 (https=) |
| AT (1) | ATE273991T1 (https=) |
| AU (1) | AU757366B2 (https=) |
| BR (1) | BR9915019A (https=) |
| CA (1) | CA2346085A1 (https=) |
| DE (2) | DE19845403B4 (https=) |
| DK (1) | DK1117676T3 (https=) |
| ES (1) | ES2226440T3 (https=) |
| HK (1) | HK1040717A1 (https=) |
| HU (1) | HUP0103570A3 (https=) |
| ID (1) | ID29353A (https=) |
| PL (1) | PL347106A1 (https=) |
| PT (1) | PT1117676E (https=) |
| RU (1) | RU2234512C2 (https=) |
| TR (1) | TR200100897T2 (https=) |
| WO (1) | WO2000020437A1 (https=) |
| ZA (1) | ZA200102586B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7053076B2 (en) | 2001-08-29 | 2006-05-30 | Xenoport, Inc. | Bile-acid derived compounds for enhancing oral absorption and systemic bioavailability of drugs |
| US7161008B2 (en) * | 2002-05-03 | 2007-01-09 | Sanofi - Aventis Deutschland GmbH | Optically active β-aminoketones, optically active 1,3-amino alcohols and processes for preparing them |
| GB0213669D0 (en) * | 2002-06-14 | 2002-07-24 | Astrazeneca Ab | Chemical compounds |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| GB0817969D0 (en) * | 2008-10-01 | 2008-11-05 | Axcess Ltd | Pharmaceutical composition |
| ES2552657T3 (es) | 2010-05-26 | 2015-12-01 | Satiogen Pharmaceuticals, Inc. | Inhibidores del reciclado de ácidos biliares y saciógenos para el tratamiento de diabetes, obesidad, y afecciones gastrointestinales inflamatorias |
| US20130108573A1 (en) | 2011-10-28 | 2013-05-02 | Lumena Pharmaceuticals, Inc. | Bile Acid Recycling Inhibitors for Treatment of Hypercholemia and Cholestatic Liver Disease |
| AU2012328526B2 (en) | 2011-10-28 | 2017-05-25 | Shire Human Genetic Therapies, Inc. | Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases |
| AU2014229050A1 (en) | 2013-03-15 | 2015-10-22 | Lumena Pharmaceuticals Llc | Bile acid recycling inhibitors for treatment of Barrett's esophagus and gastroesophageal reflux disease |
| CA2907230A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| EP3923943B1 (en) | 2019-02-12 | 2024-07-31 | Mirum Pharmaceuticals, Inc. | Genotype and dose-dependent response to an asbti in patients with bile salt export pump deficiency |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI892341L (fi) | 1988-06-10 | 1989-12-11 | Hoffmann La Roche | Propanolaminderivat. |
| GB2250634A (en) * | 1990-12-04 | 1992-06-10 | Marconi Gec Ltd | Point contact diodes |
| US5250524A (en) | 1990-12-06 | 1993-10-05 | Hoechst Aktiengesellschaft | Bile acid derivatives, process for their preparation and use of these compounds as pharmaceuticals |
| JP2616845B2 (ja) * | 1991-02-21 | 1997-06-04 | 清水化学株式会社 | システノール酸又はその胆汁酸抱合体を含有する血中コレステロール低下剤 |
| GB9203347D0 (en) * | 1992-02-17 | 1992-04-01 | Wellcome Found | Hypolipidaemic compounds |
| ATE147384T1 (de) * | 1992-02-22 | 1997-01-15 | Hoechst Ag | 4-amino-2-ureido-pyrimidin-5-carbonsäureamide, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| TW289021B (https=) * | 1993-05-08 | 1996-10-21 | Hoechst Ag | |
| EP0624593A3 (de) * | 1993-05-08 | 1995-06-07 | Hoechst Ag | Gallensäurederivate, Verfahren zu ihrer Herstellung und Verwendung dieser Verbindungen als Arzneimittel. |
| EP0869121B1 (de) * | 1997-04-04 | 2004-06-09 | Aventis Pharma Deutschland GmbH | Hypolipidämische Propanolaminderivate |
-
1998
- 1998-10-02 DE DE19845403A patent/DE19845403B4/de not_active Expired - Fee Related
-
1999
- 1999-09-18 DK DK99947385T patent/DK1117676T3/da active
- 1999-09-18 JP JP2000574548A patent/JP4598953B2/ja not_active Expired - Fee Related
- 1999-09-18 DE DE59910300T patent/DE59910300D1/de not_active Expired - Lifetime
- 1999-09-18 HK HK02102338.5A patent/HK1040717A1/zh unknown
- 1999-09-18 BR BR9915019-0A patent/BR9915019A/pt not_active IP Right Cessation
- 1999-09-18 ES ES99947385T patent/ES2226440T3/es not_active Expired - Lifetime
- 1999-09-18 AU AU60855/99A patent/AU757366B2/en not_active Ceased
- 1999-09-18 HU HU0103570A patent/HUP0103570A3/hu unknown
- 1999-09-18 ID IDW20010737A patent/ID29353A/id unknown
- 1999-09-18 AT AT99947385T patent/ATE273991T1/de not_active IP Right Cessation
- 1999-09-18 PL PL99347106A patent/PL347106A1/xx unknown
- 1999-09-18 PT PT99947385T patent/PT1117676E/pt unknown
- 1999-09-18 EP EP99947385A patent/EP1117676B1/de not_active Expired - Lifetime
- 1999-09-18 CN CNB998116343A patent/CN1227259C/zh not_active Expired - Fee Related
- 1999-09-18 KR KR1020017004131A patent/KR20010075511A/ko not_active Ceased
- 1999-09-18 WO PCT/EP1999/006930 patent/WO2000020437A1/de not_active Ceased
- 1999-09-18 RU RU2001111816/04A patent/RU2234512C2/ru not_active IP Right Cessation
- 1999-09-18 TR TR2001/00897T patent/TR200100897T2/xx unknown
- 1999-09-18 CA CA002346085A patent/CA2346085A1/en not_active Abandoned
- 1999-09-29 US US09/408,169 patent/US6180618B1/en not_active Expired - Lifetime
- 1999-09-30 AR ARP990104961A patent/AR035003A1/es unknown
-
2001
- 2001-03-29 ZA ZA200102586A patent/ZA200102586B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1040717A1 (zh) | 2002-06-21 |
| WO2000020437A1 (de) | 2000-04-13 |
| KR20010075511A (ko) | 2001-08-09 |
| RU2234512C2 (ru) | 2004-08-20 |
| BR9915019A (pt) | 2001-08-14 |
| CN1321166A (zh) | 2001-11-07 |
| PT1117676E (pt) | 2004-11-30 |
| DE19845403A1 (de) | 2000-04-13 |
| TR200100897T2 (tr) | 2001-10-22 |
| CN1227259C (zh) | 2005-11-16 |
| DK1117676T3 (da) | 2004-12-20 |
| DE19845403B4 (de) | 2005-02-10 |
| ATE273991T1 (de) | 2004-09-15 |
| ES2226440T3 (es) | 2005-03-16 |
| PL347106A1 (en) | 2002-03-25 |
| AR035003A1 (es) | 2004-04-14 |
| HUP0103570A3 (en) | 2003-01-28 |
| US6180618B1 (en) | 2001-01-30 |
| JP2002526550A (ja) | 2002-08-20 |
| ID29353A (id) | 2001-08-23 |
| DE59910300D1 (de) | 2004-09-23 |
| EP1117676B1 (de) | 2004-08-18 |
| CA2346085A1 (en) | 2000-04-13 |
| EP1117676A1 (de) | 2001-07-25 |
| AU757366B2 (en) | 2003-02-20 |
| HUP0103570A2 (hu) | 2002-02-28 |
| ZA200102586B (en) | 2001-10-03 |
| AU6085599A (en) | 2000-04-26 |
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