JPH0137398B2 - - Google Patents
Info
- Publication number
- JPH0137398B2 JPH0137398B2 JP59034125A JP3412584A JPH0137398B2 JP H0137398 B2 JPH0137398 B2 JP H0137398B2 JP 59034125 A JP59034125 A JP 59034125A JP 3412584 A JP3412584 A JP 3412584A JP H0137398 B2 JPH0137398 B2 JP H0137398B2
- Authority
- JP
- Japan
- Prior art keywords
- ursodesoxycholic acid
- acid
- disulfate
- molar
- ursodesoxycholic
- 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
Links
- 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 abstract description 23
- 229960001661 ursodiol Drugs 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 abstract 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 3
- 229940054870 urso Drugs 0.000 description 3
- 210000000941 bile Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 206010003591 Ataxia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009534 blood test Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 201000001352 cholecystitis Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000001000 lipidemic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19737A/83 | 1983-02-24 | ||
| IT19737/83A IT1221734B (it) | 1983-02-24 | 1983-02-24 | Ursodesossicolico solfato acido sale sodico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59163400A JPS59163400A (ja) | 1984-09-14 |
| JPH0137398B2 true JPH0137398B2 (en, 2012) | 1989-08-07 |
Family
ID=11160798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59034125A Granted JPS59163400A (ja) | 1983-02-24 | 1984-02-23 | ウルソデソキシコ−ル酸硫酸エステルのナトリウム塩 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4565811A (en, 2012) |
| EP (1) | EP0117570B1 (en, 2012) |
| JP (1) | JPS59163400A (en, 2012) |
| AT (1) | ATE21909T1 (en, 2012) |
| DE (1) | DE3460577D1 (en, 2012) |
| IT (1) | IT1221734B (en, 2012) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892868A (en) * | 1984-08-17 | 1990-01-09 | Gipharmex, S.P.A. | Derivatives of biliary acids, process for the production thereof and corresponding pharmaceutical compositions |
| EP0688333B1 (en) * | 1993-03-10 | 1998-08-19 | Magainin Pharmaceuticals Inc. | Steroid derivatives, pharmaceutical compositions containing them, and their use as antibiotics or disinfectants |
| DE4334823C2 (de) * | 1993-10-09 | 1998-09-17 | Schering Ag | Verfahren zur Herstellung von Schwefelsäurehalbestern von Estrogenen |
| US5840740A (en) * | 1995-06-07 | 1998-11-24 | Magainin Pharmaceuticals Inc. | Aminosterol compounds and a method of treating infection using the aminosterol compounds |
| US5856535A (en) * | 1994-08-18 | 1999-01-05 | Magainin Pharmaceuticals, Inc. | Aminosterol ester compounds |
| US6143738A (en) * | 1995-06-07 | 2000-11-07 | Magainin Pharmaceuticals, Inc. | Therapeutic uses for an aminosterol compound |
| US5763430A (en) * | 1995-06-07 | 1998-06-09 | Magainin Pharmaceuticals Inc. | Method of treating a viral infection by administering a steroid compound |
| US5795885A (en) * | 1995-06-07 | 1998-08-18 | Magainin Pharmaceuticals Inc. | Method of inhibiting profileration of cells by administering an aminosterol compound |
| US5994336A (en) * | 1995-06-07 | 1999-11-30 | Magainin Pharmaceuticals Inc. | Method of inhibiting proliferation of cells by administering an aminosterol compound |
| US5847172A (en) * | 1995-06-07 | 1998-12-08 | Magainin Pharmaceuticals Inc. | Certain aminosterol compounds and pharmaceutical compositions including these compounds |
| US5840936A (en) * | 1995-06-07 | 1998-11-24 | Magainin Pharmaceuticals Inc. | Aminosterol compounds useful as inhibitors of the sodium/proton exchanger (NHE) |
| US5874597A (en) * | 1995-06-07 | 1999-02-23 | Magainin Pharmaceuticals, Inc. | Certain aminosterol compounds and pharmaceutical compositions including these compounds |
| US5792635A (en) * | 1995-06-07 | 1998-08-11 | Magainin Pharmaceuticals, Inc. | Method of inhibiting the sodium/proton exchanger NHE3 and method of inhibiting growth by administering squalamine |
| US5763435A (en) | 1995-11-21 | 1998-06-09 | Children's Hospital Medical Center | Sulfate conjugates of ursodeoxycholic acid, and their beneficial use in inflammatory disorders |
| IT1283225B1 (it) * | 1996-03-11 | 1998-04-16 | Renata Maria Anna Ve Cavaliere | Ceppi di batteri, composizione farmaceutica contenente uno o piu' di tali ceppi e uso dei medesimi per la prevenzione e la terapia delle |
| US6596712B2 (en) | 1996-04-26 | 2003-07-22 | Genaera Corporation | Treatment of carcinomas using squalamine in combination with other anti-cancer agents or modalities |
| DE69722793T2 (de) * | 1996-04-26 | 2004-05-19 | Genaera Corp. | Squalamin in kombination mit anderen antikrebs-mittelen zur behandlung von tumoren |
| IN186119B (en, 2012) * | 1996-07-25 | 2001-06-23 | Lg Chemical Ltd | |
| US6262283B1 (en) | 1996-12-06 | 2001-07-17 | Magainin Pharmaceuticals Inc. | Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds |
| DE60123939T2 (de) * | 2000-04-12 | 2007-05-31 | Genaera Corp. | Ein verfahren zur herstellung von 7.alpha.-hydroxy 3-aminosubstituierten sterol-verbindungen, ohne schutz der 7.alpha.-hydroxy-gruppe |
| ITTO20020102A1 (it) * | 2002-02-06 | 2003-08-06 | Abc Ist Biolog Chem Spa | Procedimento per la preparazione dell'acido ursodesossicolico disolfato e suoi sali farmaceuticamente accettabili. |
| ITMI20030822A1 (it) * | 2003-04-18 | 2004-10-19 | Erregierre Spa | Processo per la preparazione dell'acido ursodesossicolico |
| IT1393095B1 (it) | 2009-02-19 | 2012-04-11 | Prodotti Chimici Alimentari | Processo per la sintesi del sale disodico dell'acido ursodesossicolico 3,7-disolfato. |
| ITTO20111069A1 (it) * | 2011-11-21 | 2013-05-22 | Abc Farmaceutici S P A | Formulazione farmaceutica liquida palatabile, per uso orale, comprendente acido ursodesossicolico estere solforico. |
| US12186329B2 (en) | 2018-08-23 | 2025-01-07 | President And Fellows Of Harvard College | Compositions and methods related to cholic acid 7-sulfate as a treatment for diabetes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2444048B1 (en, 2012) * | 1978-12-15 | 1981-08-14 | Roussel Uclaf | |
| JPS5772903A (en) * | 1980-10-27 | 1982-05-07 | Mitsubishi Petrochem Co Ltd | Pyrazole herbicide |
| IT1167479B (it) * | 1981-07-24 | 1987-05-13 | Carlo Scolastico | Derivati dell'acido chenodesossicolico |
| IT1150756B (it) * | 1982-04-02 | 1986-12-17 | Zambon Spa | Procedimento per preparare l'acido 3alfa, 7beta-diidrossi-5beta-colanico |
-
1983
- 1983-02-24 IT IT19737/83A patent/IT1221734B/it active
-
1984
- 1984-01-27 EP EP84200102A patent/EP0117570B1/en not_active Expired
- 1984-01-27 DE DE8484200102T patent/DE3460577D1/de not_active Expired
- 1984-01-27 AT AT84200102T patent/ATE21909T1/de not_active IP Right Cessation
- 1984-02-22 US US06/582,522 patent/US4565811A/en not_active Expired - Lifetime
- 1984-02-23 JP JP59034125A patent/JPS59163400A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3460577D1 (en) | 1986-10-09 |
| IT1221734B (it) | 1990-07-12 |
| EP0117570A1 (en) | 1984-09-05 |
| JPS59163400A (ja) | 1984-09-14 |
| ATE21909T1 (de) | 1986-09-15 |
| US4565811A (en) | 1986-01-21 |
| EP0117570B1 (en) | 1986-09-03 |
| IT8319737A0 (it) | 1983-02-24 |
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