FI87791B - Foerfarande foer framstaellning av 17 -(cyklopropyloxi)androst-5-en-3 -ol och naerstaoende foereningar, som aer anvaendbara som c17-20 lyas inhibitorer - Google Patents
Foerfarande foer framstaellning av 17 -(cyklopropyloxi)androst-5-en-3 -ol och naerstaoende foereningar, som aer anvaendbara som c17-20 lyas inhibitorer Download PDFInfo
- Publication number
- FI87791B FI87791B FI881878A FI881878A FI87791B FI 87791 B FI87791 B FI 87791B FI 881878 A FI881878 A FI 881878A FI 881878 A FI881878 A FI 881878A FI 87791 B FI87791 B FI 87791B
- Authority
- FI
- Finland
- Prior art keywords
- androst
- som
- reacted
- hydrogen
- protecting group
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0029—Ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (4)
1. Förfarande för framställning av en terapeutiskt användbar 17B-(cyklopropyloxi)androst-5-en-36-ol med for-5 meln X “ rrS’ — Q X— 15 väri R är väte eller metyl; X är 0 eller S; Y är väte el- ler C^-alkyl; och Q Sr 20. eller aAJ 0 (I) (II) 25 väri Z är väte eller en alkanoyl med 1-10 kolatomer eller en cyklopentan- och bensenalkanoly, vars alkanoyldel innehäller högst 4 kolatomer, kännetecknat därav, att vinyleter med formeln
30 CR»=CH2 0 rVl" jGu^ AO — is 37791 väri R och Y Mr ovan definierade och A är en skyddsgrupp, bringas att reagera med en Sinunons-Smith -reagens, varef-ter skyddsgruppen avlägsnas vid en 3-position och varefter eventuellt: 5 a) 3-hydroxiföreningen oxideras tili en motsvarande 3-keto-A4-förening med hjälp av aluminiumpropoxid; eller b) 3-hydroxigruppen estreras med en lämplig syra-klorid, varvid motsvarande ester erhälls.
2. Förfarande enligt patentkravet 1 för framställ-10 ning av en förening med formeln O 15 /sj/4-'-γ
20 H° väri R är väte eller metyl och Y är väte eller C^-alkyl, kännetecknat därav, att vinyleter med formeln CR=CH, O 25 ,-Y 30 /L /L /> AO väri R och Y är ovan definierade och A är en skyddsgrupp, bringas att reagera med en Simmons-Smith -reagens, varef-35 ter skyddsgruppen avlägsnas. ie 87791
3. Förfarande enligt patentkravet 1 för f rams fanning av 17B-(cyklopropyloxi )androst-5-en-3B-ol,. , k ä n -netecknat därav, att 3B-(t-butyldimetylsilyloxi)-17B-etenyloxiandrost-5-en bringas att reagera med dijodme- 5 tan och zink-koppar-par, varefter det behandlas med tetra-butylammoniumfluorid för att avlägsna silylskyddsgruppen.
4. Förfarande enligt patentkravet 1 för framställ-ning av 17B-(cyklopropyloxi)androst-4-en-3B-ol, k ä n -netecknat därav, att 3B-(t-butyldimetylsilyloxi)- 10 17B-etenyloxiandrost-5-en bringas att reagera med dijodme-tan och zink-koppar-par, varefter det behandlas med tetra-butylammoniumfluorid för att avlägsna silylskyddsgruppen och sedan oxideras med aluminiumisopropoxid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4117087 | 1987-04-22 | ||
| US07/041,170 US4891367A (en) | 1987-04-22 | 1987-04-22 | 17β-(cyclopropyloxy)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI881878A0 FI881878A0 (fi) | 1988-04-21 |
| FI881878A FI881878A (fi) | 1988-10-23 |
| FI87791B true FI87791B (fi) | 1992-11-13 |
| FI87791C FI87791C (sv) | 1993-02-25 |
Family
ID=21915121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI881878A FI87791C (sv) | 1987-04-22 | 1988-04-21 | Förfarande för framställning av 17 -(cyklopropyloxi)androst-5-en-3 -ol och närstående föreningar, som är användbara som C17-20 lyas inhibito rer |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4891367A (sv) |
| EP (1) | EP0291717B1 (sv) |
| JP (1) | JP2593685B2 (sv) |
| KR (1) | KR960015036B1 (sv) |
| CN (1) | CN1024279C (sv) |
| AT (1) | ATE78487T1 (sv) |
| AU (1) | AU605575B2 (sv) |
| CA (1) | CA1309088C (sv) |
| DE (1) | DE3872938T2 (sv) |
| DK (1) | DK167766B1 (sv) |
| ES (1) | ES2051787T3 (sv) |
| FI (1) | FI87791C (sv) |
| GR (1) | GR3005370T3 (sv) |
| HU (1) | HU198508B (sv) |
| IL (1) | IL86140A (sv) |
| NO (1) | NO168892C (sv) |
| NZ (1) | NZ224287A (sv) |
| PH (1) | PH23863A (sv) |
| PT (1) | PT87293B (sv) |
| ZA (1) | ZA882715B (sv) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ224288A (en) * | 1987-04-22 | 1989-12-21 | Merrell Dow Pharma | 17b-(cyclopropylamino)androst-5-en-3b-ol and related compounds and methods using these for treatment of non-humans |
| US4954488A (en) * | 1989-06-14 | 1990-09-04 | Merrell Dow Pharmaceuticals Inc. | Method of treating hyperaldosteronism using 17β-cyclopropylaminoandrostene derivatives |
| US4966897A (en) * | 1989-08-15 | 1990-10-30 | Merrell Dow Pharmaceuticals Inc. | 4-substituted 17β-(cyclopropyloxy)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors |
| US5102915A (en) * | 1990-03-22 | 1992-04-07 | Merrell Dow Pharmaceuticals Inc. | Cyclopropyl squalene derivatives and their use as inhibitors of cholesterol synthesis |
| US5051534A (en) * | 1990-03-22 | 1991-09-24 | Merrell Dow Pharmaceuticals Inc. | Novel cyclopropyl squalene derivatives and their use as inhibitors of cholesterol synthesis |
| US5486511A (en) * | 1993-05-25 | 1996-01-23 | Merrell Dow Pharmaceuticals Inc. | 4-amino-17β-(cyclopropyloxy)androst-4-en-3-one, 4-amino-17β-(cyclopropylamino)androst-4-en-3-one and related compounds as C17-20 lyase and 5α-reductase |
| US5661141A (en) * | 1995-03-27 | 1997-08-26 | Petrow; Vladimir | 19-oxygenated steroids as therapeutic agents |
| US6365597B1 (en) | 1996-02-14 | 2002-04-02 | Aventis Pharmaceuticals Inc. | 4-aza steroids |
| US6093389A (en) * | 1997-12-01 | 2000-07-25 | American Cyanamid Company | Methods and compositions for attracting and controlling termites |
| WO2003039250A2 (en) * | 2001-11-08 | 2003-05-15 | Colorado State University Research Foundation | Termite feeding stimulant and method for using same |
| EP2155204B1 (en) * | 2007-06-15 | 2016-08-17 | Research Triangle Institute | Androstane and pregnane steroids with potent allosteric gaba receptor chloride ionophore modulating properties |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135744A (en) * | 1961-04-12 | 1964-06-02 | Vismara Francesco Spa | Cycloalkenyl ethers of 17 beta-hydroxy androstanes |
| CH471103A (de) * | 1962-02-28 | 1969-04-15 | Warner Lambert Pharmaceutical | Verfahren zur Herstellung neuer (1'-Alkoxy)-alkyl- und cycloalkyläther von 17B-Hydroxysteroiden |
| US3475464A (en) * | 1966-11-07 | 1969-10-28 | Syntex Corp | Process for the preparation of steroids and novel intermediates thereof |
| US3732209A (en) * | 1971-03-15 | 1973-05-08 | Hoffmann La Roche | Novel 17beta-oxygenated cyclopropa(16alpha,17alpha)steroids |
| US3763146A (en) * | 1972-02-03 | 1973-10-02 | Syntex Corp | Novel 17beta(tetrahydropyran-4-yloxy)steroids |
| US4139617A (en) * | 1974-05-13 | 1979-02-13 | Richardson-Merrell Inc. | 19-Oxygenated-androst-5-enes for the enhancement of libido |
| US4361559A (en) * | 1981-08-20 | 1982-11-30 | E. R. Squibb & Sons, Inc. | Antiinflammatory 17,17-bis (substituted thio) androstenes |
| US4420428A (en) * | 1982-12-27 | 1983-12-13 | E. R. Squibb & Sons, Inc. | 16-Ketoandrostene-17-dithioketals |
| US4427592A (en) * | 1983-01-31 | 1984-01-24 | E. R. Squibb & Sons, Inc. | Androstene-17-dithioketals |
| US4529548A (en) * | 1984-05-07 | 1985-07-16 | E. R. Squibb & Sons, Inc. | 17β-(substituted thio)androstenes |
| NZ224288A (en) * | 1987-04-22 | 1989-12-21 | Merrell Dow Pharma | 17b-(cyclopropylamino)androst-5-en-3b-ol and related compounds and methods using these for treatment of non-humans |
-
1987
- 1987-04-22 US US07/041,170 patent/US4891367A/en not_active Expired - Fee Related
-
1988
- 1988-04-18 AU AU14720/88A patent/AU605575B2/en not_active Ceased
- 1988-04-18 ZA ZA882715A patent/ZA882715B/xx unknown
- 1988-04-18 CA CA000564363A patent/CA1309088C/en not_active Expired - Lifetime
- 1988-04-18 NZ NZ224287A patent/NZ224287A/xx unknown
- 1988-04-19 PH PH36816A patent/PH23863A/en unknown
- 1988-04-20 IL IL86140A patent/IL86140A/xx not_active IP Right Cessation
- 1988-04-21 CN CN88102175A patent/CN1024279C/zh not_active Expired - Fee Related
- 1988-04-21 HU HU882028A patent/HU198508B/hu not_active IP Right Cessation
- 1988-04-21 ES ES88106395T patent/ES2051787T3/es not_active Expired - Lifetime
- 1988-04-21 FI FI881878A patent/FI87791C/sv not_active IP Right Cessation
- 1988-04-21 AT AT88106395T patent/ATE78487T1/de active
- 1988-04-21 DE DE8888106395T patent/DE3872938T2/de not_active Expired - Fee Related
- 1988-04-21 KR KR1019880004519A patent/KR960015036B1/ko not_active IP Right Cessation
- 1988-04-21 NO NO881745A patent/NO168892C/no unknown
- 1988-04-21 EP EP88106395A patent/EP0291717B1/en not_active Expired - Lifetime
- 1988-04-21 DK DK217488A patent/DK167766B1/da not_active IP Right Cessation
- 1988-04-21 JP JP63096970A patent/JP2593685B2/ja not_active Expired - Fee Related
- 1988-04-21 PT PT87293A patent/PT87293B/pt not_active IP Right Cessation
-
1992
- 1992-08-06 GR GR920401704T patent/GR3005370T3/el unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: MERRELL DOW PHARMACEUTICALS INC. |