DK167220B1 - 24r-scymnol, fremgangsmaade til fremstilling heraf samt farmaceutisk praeparat indeholdende samme - Google Patents

24r-scymnol, fremgangsmaade til fremstilling heraf samt farmaceutisk praeparat indeholdende samme Download PDF

Info

Publication number: DK167220B1
Authority: DK; Denmark
Prior art keywords: scymnol; preparing; process according; liver; pharmaceutical preparation
Prior art date: 1988-02-19

Application number

DK192890A

Other languages

Danish (da)

English (en)

Other versions

DK192890D0 (da

DK192890A (da

Inventor

Yoshiki Kosuge

Takuo Kosuge

Kuniro Tsuji

Hitoshi Ishida

Original Assignee

Broadbent J W Nominees Pty Ltd

Priority date (The priority date 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 date listed.)

1988-02-19

Filing date

1990-08-14

Publication date

1993-09-20

1990-08-14 Application filed by Broadbent J W Nominees Pty Ltd filed Critical Broadbent J W Nominees Pty Ltd

1990-08-14 Publication of DK192890D0 publication Critical patent/DK192890D0/da

1990-08-14 Publication of DK192890A publication Critical patent/DK192890A/da

1993-09-20 Application granted granted Critical

1993-09-20 Publication of DK167220B1 publication Critical patent/DK167220B1/da

Links

238000004519 manufacturing process Methods 0.000 title description 2
239000000825 pharmaceutical preparation Substances 0.000 title 1
238000000034 method Methods 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
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 3
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 3
229910001626 barium chloride Inorganic materials 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
BYPAPZOIGAURCH-XFEBKPBNSA-M sodium;[(2s,3r,6r)-3-hydroxy-2-(hydroxymethyl)-6-[(3r,5s,7r,8r,9s,10s,12s,13r,14s,17r)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]heptyl] sulfate Chemical compound [Na+].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](CC[C@@H](O)[C@@H](CO)COS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 BYPAPZOIGAURCH-XFEBKPBNSA-M 0.000 claims description 2
229910021653 sulphate ion Inorganic materials 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 15
DIPHJTHZUWDJIK-JPLAUYQNSA-N 5beta-scymnol 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](CC[C@@H](O)C(CO)CO)C)[C@@]2(C)[C@@H](O)C1 DIPHJTHZUWDJIK-JPLAUYQNSA-N 0.000 description 12
DIPHJTHZUWDJIK-UHFFFAOYSA-N Scymnol Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)C(CO)CO)C)C1(C)C(O)C2 DIPHJTHZUWDJIK-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000002474 experimental method Methods 0.000 description 7
241000251730 Chondrichthyes Species 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
210000000941 bile Anatomy 0.000 description 5
210000004185 liver Anatomy 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
102000016540 Tyrosine aminotransferases Human genes 0.000 description 4
108010042606 Tyrosine transaminase Proteins 0.000 description 4
KKADPXVIOXHVKN-UHFFFAOYSA-N 4-hydroxyphenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=C(O)C=C1 KKADPXVIOXHVKN-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
208000019423 liver disease Diseases 0.000 description 3
239000000203 mixture Substances 0.000 description 3
GQYBCIHRWMPOOF-UHFFFAOYSA-N p-hydroxyphenylpyruvic acid Natural products OC(=O)C(O)=CC1=CC=C(O)C=C1 GQYBCIHRWMPOOF-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910002483 Cu Ka Inorganic materials 0.000 description 2
230000005976 liver dysfunction Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
206010067125 Liver injury Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000012926 crystallographic analysis Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
210000000232 gallbladder Anatomy 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
230000003908 liver function Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
230000036387 respiratory rate Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
230000009182 swimming Effects 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1

Classifications

- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Gastroenterology & Hepatology (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Saccharide Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Glass Compositions (AREA)
Polymerisation Methods In General (AREA)
Compounds Of Unknown Constitution (AREA)
Luminescent Compositions (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

DK192890A 1988-02-19 1990-08-14 24r-scymnol, fremgangsmaade til fremstilling heraf samt farmaceutisk praeparat indeholdende samme DK167220B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
AUPI685088		1988-02-19
AUPI685088		1988-02-19
PCT/AU1989/000064 WO1989007607A1 (en)	1988-02-19	1989-02-16	24r-scymnol, and preparation and use thereof
AU8900064		1989-02-16

Publications (3)

Publication Number	Publication Date
DK192890D0 DK192890D0 (da)	1990-08-14
DK192890A DK192890A (da)	1990-08-14
DK167220B1 true DK167220B1 (da)	1993-09-20

Family

ID=3772839

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK192890A DK167220B1 (da)	1988-02-19	1990-08-14	24r-scymnol, fremgangsmaade til fremstilling heraf samt farmaceutisk praeparat indeholdende samme

Country Status (14)

Country	Link
EP (1)	EP0401262B1 (es)
JP (1)	JP2716827B2 (es)
AT (1)	ATE132500T1 (es)
AU (1)	AU609959B2 (es)
CA (1)	CA1328104C (es)
DE (1)	DE68925355T2 (es)
DK (1)	DK167220B1 (es)
ES (1)	ES2013025A6 (es)
GR (1)	GR1001203B (es)
HK (1)	HK88396A (es)
NZ (1)	NZ228023A (es)
PT (1)	PT89742B (es)
WO (1)	WO1989007607A1 (es)
ZA (1)	ZA891242B (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6884796B2 (en)	1998-05-13	2005-04-26	Novonordisk A/S	Meiosis regulating compounds

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU597723B2 (en) *	1986-08-21	1990-06-07	J.W. Broadbent Nominees Pty. Ltd.	Sodium scymnol sulphate isolated form shark tissues
WO1992000316A1 (fr) *	1990-06-30	1992-01-09	Tsumura & Co., Ltd.	Alcool biliaire et medicament contenant cet alcool comme ingredient actif
ZA947912B (en) *	1993-10-12	1995-05-24	Broadbent J W Nominees Pty Ltd	Treatment of medical disorders associated with free radical formation
CN100383157C (zh) *	2006-06-01	2008-04-23	中国科学院南海海洋研究所	3β，5α，6β，11β-四羟基胆甾烷醇及其制备方法和用途
EP2171455A4 (en)	2007-07-06	2010-11-24	Vaxdesign Corp	FAST GENERATION OF T-CELL INDEPENDENT ANTIBODY REACTIONS TO T-CELL DEPENDENT ANTIGENES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3931403A (en)	1973-05-25	1976-01-06	Intellectual Property Development Corporation	Antimicrobial compositions

1989
- 1989-02-16 DE DE68925355T patent/DE68925355T2/de not_active Expired - Fee Related
- 1989-02-16 AT AT89902728T patent/ATE132500T1/de not_active IP Right Cessation
- 1989-02-16 WO PCT/AU1989/000064 patent/WO1989007607A1/en not_active Ceased
- 1989-02-16 JP JP1502524A patent/JP2716827B2/ja not_active Expired - Fee Related
- 1989-02-16 AU AU31861/89A patent/AU609959B2/en not_active Ceased
- 1989-02-16 EP EP89902728A patent/EP0401262B1/en not_active Expired - Lifetime
- 1989-02-17 NZ NZ228023A patent/NZ228023A/xx unknown
- 1989-02-17 ZA ZA891242A patent/ZA891242B/xx unknown
- 1989-02-17 CA CA000591695A patent/CA1328104C/en not_active Expired - Fee Related
- 1989-02-17 PT PT89742A patent/PT89742B/pt not_active IP Right Cessation
- 1989-02-17 ES ES898900585A patent/ES2013025A6/es not_active Expired - Fee Related
- 1989-02-20 GR GR890100102A patent/GR1001203B/el not_active IP Right Cessation
1990
- 1990-08-14 DK DK192890A patent/DK167220B1/da not_active IP Right Cessation
1996
- 1996-05-23 HK HK88396A patent/HK88396A/en not_active IP Right Cessation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6884796B2 (en)	1998-05-13	2005-04-26	Novonordisk A/S	Meiosis regulating compounds
USRE39678E1 (en) *	1998-05-13	2007-06-05	Novo Nordisk A/S	Meiosis regulating compounds

Also Published As

Publication number	Publication date
JPH03503407A (ja)	1991-08-01
DE68925355T2 (de)	1996-08-01
AU609959B2 (en)	1991-05-09
DK192890D0 (da)	1990-08-14
NZ228023A (en)	1991-10-25
DK192890A (da)	1990-08-14
CA1328104C (en)	1994-03-29
AU3186189A (en)	1989-09-06
EP0401262B1 (en)	1996-01-03
PT89742A (pt)	1989-10-04
HK88396A (en)	1996-05-31
PT89742B (pt)	1994-03-31
GR1001203B (el)	1993-06-21
DE68925355D1 (de)	1996-02-15
ES2013025A6 (es)	1990-04-16
EP0401262A1 (en)	1990-12-12
JP2716827B2 (ja)	1998-02-18
ATE132500T1 (de)	1996-01-15
WO1989007607A1 (en)	1989-08-24
ZA891242B (en)	1989-10-25
EP0401262A4 (en)	1993-05-05

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Legal Events

Date	Code	Title	Description
1990-09-10	AHS	Application shelved for other reasons than non-payment
1993-09-20	B1	Patent granted (law 1993)
2005-10-03	PBP	Patent lapsed	Country of ref document: DK