HRP950459A2 - Spirostanyl glycosidal crystals - Google Patents

Spirostanyl glycosidal crystals Download PDF

Info

Publication number: HRP950459A2
Authority: HR; Croatia
Prior art keywords: crystalline; oxy; cellobiosyl; spirostan; fluorophenylcarbamoyl
Prior art date: 1994-08-30

Application number

HR08/298,106A

Other languages

English (en)

Croatian (hr)

Inventor

Allen J Douglas

Richard A Buzon

Michael P Dennino

Harry A Watson

Jonathan B Zung

Original Assignee

Pfizer

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.)

1994-08-30

Filing date

1995-08-25

Publication date

1997-08-31

1995-08-25 Application filed by Pfizer filed Critical Pfizer

1997-08-31 Publication of HRP950459A2 publication Critical patent/HRP950459A2/hr

Links

-1 Spirostanyl Chemical group 0.000 title claims description 16
239000013078 crystal Substances 0.000 title claims description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
229930182470 glycoside Natural products 0.000 claims description 12
208000035150 Hypercholesterolemia Diseases 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
238000002441 X-ray diffraction Methods 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
229930002534 steroid glycoside Natural products 0.000 claims description 7
201000001320 Atherosclerosis Diseases 0.000 claims description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
239000002131 composite material Substances 0.000 claims description 5
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
150000001875 compounds Chemical class 0.000 description 34
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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 13
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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JAYFDQORNVHIKI-RBOFTKOOSA-N (1R,2S,4R,5'R,6R,7S,8R,9S,12S,13S)-3-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1O)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 JAYFDQORNVHIKI-RBOFTKOOSA-N 0.000 description 1
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239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000001397 quillaja saponaria molina bark Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 description 1
239000008299 semisolid dosage form Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
241000894007 species Species 0.000 description 1
INLFWQCRAJUDCR-LYLBMTSKSA-N spirostane Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 INLFWQCRAJUDCR-LYLBMTSKSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000037351 starvation Effects 0.000 description 1
150000008143 steroidal glycosides Chemical class 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
RMCMCFUBWGCJLE-UHFFFAOYSA-N sulfuric acid;4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound OS(O)(=O)=O.C1CC2(C)C(=O)CC1C2(C)C RMCMCFUBWGCJLE-UHFFFAOYSA-N 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
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000000115 thoracic cavity Anatomy 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Saccharide Compounds (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HR08/298,106A 1994-08-30 1995-08-25 Spirostanyl glycosidal crystals HRP950459A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US29810694A	1994-08-30	1994-08-30

Publications (1)

Publication Number	Publication Date
HRP950459A2 true HRP950459A2 (en)	1997-08-31

Family

ID=23149057

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR08/298,106A HRP950459A2 (en)	1994-08-30	1995-08-25	Spirostanyl glycosidal crystals

Country Status (20)

Country	Link
US (1)	US5804562A (sl)
EP (1)	EP0778846A1 (sl)
JP (1)	JPH09510735A (sl)
KR (1)	KR970705574A (sl)
AU (1)	AU2265395A (sl)
BR (1)	BR9503827A (sl)
CA (1)	CA2198097A1 (sl)
CO (1)	CO4480032A1 (sl)
FI (1)	FI970828A (sl)
HR (1)	HRP950459A2 (sl)
IL (1)	IL115062A0 (sl)
MA (1)	MA23651A1 (sl)
MX (1)	MX9701525A (sl)
NO (1)	NO970910L (sl)
OA (1)	OA10402A (sl)
PE (1)	PE47696A1 (sl)
PL (1)	PL318937A1 (sl)
SI (1)	SI9520092A (sl)
TR (1)	TR199501065A2 (sl)
WO (1)	WO1996006854A1 (sl)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69929177T2 (de) *	1998-03-26	2006-08-24	Phytopharm Plc, Godmanchester	Smilagenin und anzurogenin-d zur behandlung der alzheimerischen krankheit
GB9923076D0 (en) *	1999-09-29	1999-12-01	Phytopharm Plc	Sapogenin derivatives and their use
GB9923078D0 (en) *	1999-09-29	1999-12-01	Phytopharm Plc	Sapogenin derivatives and their use
GB9923077D0 (en) *	1999-09-29	1999-12-01	Phytopharm Plc	Sapogenin derivatives and their use
GB0000228D0 (en) *	2000-01-06	2000-03-01	Phytopharm Plc	Fluoro substituted sapogenins and their use
GB0107822D0 (en) *	2001-03-28	2001-05-23	Phytopharm Plc	Sapogenin derivatives their synthesis and use methods based upon their use
KR101130212B1 (ko) *	2002-03-27	2012-04-13	파이토팜 피엘씨	사포게닌 및 그 유도체의 치료 방법 및 사용법
US20050130948A1 (en) *	2002-03-27	2005-06-16	Daryl Rees	Therapeutic methods and uses of sapogenins and their derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR9306619A (pt) *	1992-06-26	1998-12-08	Pfizer	Glicosídeos esteroidais para o tratamento da hipercolesterolemia
AU7948494A (en) *	1993-12-28	1995-07-17	Pfizer Inc.	Steroidal glycosides

1995
- 1995-05-04 WO PCT/IB1995/000317 patent/WO1996006854A1/en not_active Application Discontinuation
- 1995-05-04 MX MX9701525A patent/MX9701525A/es unknown
- 1995-05-04 EP EP95915968A patent/EP0778846A1/en not_active Withdrawn
- 1995-05-04 CA CA002198097A patent/CA2198097A1/en not_active Abandoned
- 1995-05-04 AU AU22653/95A patent/AU2265395A/en not_active Abandoned
- 1995-05-04 PL PL95318937A patent/PL318937A1/xx unknown
- 1995-05-04 SI SI9520092A patent/SI9520092A/sl unknown
- 1995-05-04 KR KR1019970701280A patent/KR970705574A/ko not_active Application Discontinuation
- 1995-05-04 JP JP8508579A patent/JPH09510735A/ja not_active Ceased
- 1995-08-21 MA MA23993A patent/MA23651A1/fr unknown
- 1995-08-23 CO CO95037817A patent/CO4480032A1/es unknown
- 1995-08-24 IL IL11506295A patent/IL115062A0/xx unknown
- 1995-08-25 HR HR08/298,106A patent/HRP950459A2/hr not_active Application Discontinuation
- 1995-08-28 PE PE1995277474A patent/PE47696A1/es not_active Application Discontinuation
- 1995-08-29 BR BR9503827A patent/BR9503827A/pt not_active Application Discontinuation
- 1995-08-29 TR TR95/01065A patent/TR199501065A2/xx unknown
1997
- 1997-02-27 FI FI970828A patent/FI970828A/fi not_active Application Discontinuation
- 1997-02-27 NO NO970910A patent/NO970910L/no unknown
- 1997-02-28 OA OA60970A patent/OA10402A/en unknown
- 1997-05-01 US US08/809,160 patent/US5804562A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
SI9520092A (en)	1997-12-31
AU2265395A (en)	1996-03-22
PL318937A1 (en)	1997-07-21
FI970828A0 (fi)	1997-02-27
PE47696A1 (es)	1996-11-12
OA10402A (en)	2001-12-05
MX9701525A (es)	1997-05-31
CO4480032A1 (es)	1997-07-09
WO1996006854A1 (en)	1996-03-07
NO970910D0 (no)	1997-02-27
BR9503827A (pt)	1996-09-10
FI970828A (fi)	1997-02-27
IL115062A0 (en)	1995-12-08
MA23651A1 (fr)	1996-04-01
JPH09510735A (ja)	1997-10-28
EP0778846A1 (en)	1997-06-18
CA2198097A1 (en)	1996-03-07
US5804562A (en)	1998-09-08
KR970705574A (ko)	1997-10-09
NO970910L (no)	1997-02-27
TR199501065A2 (tr)	1996-06-21

Publication	Publication Date	Title
EP2892910B1 (en)	2016-09-07	Glycyrrhetinic acid derivatives with anti-inflammatory activity
US5583239A (en)	1996-12-10	Antimicrobial sterol conjugates
SK158394A3 (en)	1995-05-10	Steroidal glycosides
EP1117645A1 (de)	2001-07-25	Arylsubstituierte propanolaminderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung
SK14162001A3 (sk)	2002-03-05	Deriváty 1,4-benzotiazepín-1,1-dioxidu substituované cukrovnými zvyškami, spôsob ich prípravy, liečivá, ktoré ich obsahujú, a ich použitie
HU221584B (hu)	2002-11-28	Új vastagbél- (colon) vagy csípőbél- (ileum) specifikus, cukortartalmú szteroidszármazékok, ezeket tartalmazó gyógyszerkészítmények és előállításuk
HRP950459A2 (en)	1997-08-31	Spirostanyl glycosidal crystals
JPH01156995A (ja)	1989-06-20	新規なアンドロスタン１７−カルボン酸エステル、その製法及びそれを含む薬剤
JP4613366B2 (ja)	2011-01-19	抗炎症活性を有するマクロライドコンジュゲート
AP518A (en)	1996-08-23	Spirostanyl glycosidal crystalline monohydrate.
HUT76333A (en)	1997-08-28	Triterpene derivative and medicinal composition
CA1113006A (en)	1981-11-24	Medicine with activity as prostaglandin-synthetase inhibitor
HRP941012A2 (en)	1997-08-31	Steroidal glycosides
US6150336A (en)	2000-11-21	Steroidal glycosides
CA2171740C (en)	2005-07-26	0rally active derivatives of 1,3,5(10)-estratriene
US4265886A (en)	1981-05-05	Spiroketalins and their applications
JP2000191685A (ja)	2000-07-11	コレスタノール化合物及びこれを含有する医薬
JPH1160592A (ja)	1999-03-02	コレスタノール化合物及びこれを含有する医薬
CN102153613B (zh)	2013-08-14	夏枯草酸的制备方法和应用
GB2024624A (en)	1980-01-16	Anti inflammatory spiroketalins
JPS6363698A (ja)	1988-03-22	胆汁酸誘導体およびその塩ならびにその製造法
CN1156458A (zh)	1997-08-06	螺甾烷基糖苷晶体
JPH02138292A (ja)	1990-05-28	２’‐メチリデンピリミジンヌクレオシド化合物およびその医薬用途
JPH08104638A (ja)	1996-04-23	Ｉｌ−５産生抑制剤

Legal Events

Date	Code	Title
1997-08-31	A1OB	Publication of a patent application
1998-02-27	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2000-05-18	OBST	Application withdrawn