IE33567L - 4-oxa-3-oxo-androstanes - Google Patents
4-oxa-3-oxo-androstanesInfo
- Publication number
- IE33567L IE33567L IE681298A IE129868A IE33567L IE 33567 L IE33567 L IE 33567L IE 681298 A IE681298 A IE 681298A IE 129868 A IE129868 A IE 129868A IE 33567 L IE33567 L IE 33567L
- Authority
- IE
- Ireland
- Prior art keywords
- compounds
- alkyl
- oxo
- androstan
- seco
- Prior art date
Links
- DXJOQJNZUZXIQM-RIMFYDMWSA-N (3as,3bs,5ar,9ar,9bs,11as)-9a,11a-dimethyl-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]chromen-7-one Chemical class O([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 DXJOQJNZUZXIQM-RIMFYDMWSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 235000018734 Sambucus australis Nutrition 0.000 abstract 2
- 244000180577 Sambucus australis Species 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910001510 metal chloride Inorganic materials 0.000 abstract 1
- 229910001512 metal fluoride Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
-
- 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
- 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
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B33/00—Constructional parts, details or accessories not provided for in the other groups of this subclass
- G11B33/02—Cabinets; Cases; Stands; Disposition of apparatus therein or thereon
- G11B33/04—Cabinets; Cases; Stands; Disposition of apparatus therein or thereon modified to store record carriers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,247,022. 3,5-Seco-A-nor-androstan-3-oic acids. F. HOFFMANNLA ROCHE & CO. A.G. 1 Nov., 1968 [3 Nov., 1967], No. 29584/70. Divided out of 1,247,021. Heading C2C. The invention comprises compounds of Formulµ Ia and Ib wherein R<SP>1</SP> is H, C 1-7 alkyl or C 1-7 alkanyol, R<SP>2</SP> is H or C 1-7 alkyl, A is Cl 2 , Br 2 or (X, H) where X is Cl, Br or F and may be in the α- or #-configuration, A<SP>1</SP> is Cl or Br and D is CO or CHOH. Their preparation is as follows: la (D = CO, A is other than F, H): by mono- or di-halogenation of the corresponding dehalo compounds; Ia (D = CO, A = (Cl, H)): by reacting the corresponding compounds in which A = (Br, H) with a metal chloride; Ia (D = CO, A = (F, H)): by reacting the corresponding compounds in which A = (Cl, H) or (Br, H) or alkyl esters thereof with a metal fluoride, and saponification when the product is an alkyl ester; Ia (D = CHOH, A = (Cl, H) or (Br, H)): reduction of a compound Ib; la (D = CHOH, A = any value): reduction of the corresponding ketones (D = CO); Ib: dehydrohalogenation of compounds Ia wherein D = CO and A = Cl 2 or Br 2 . In addition, Ia (D = CO, A = (#-Br, H)) may be epimerized with NaOH to Ia (D = CO, A = (α-Br, H)). A mixture of 6α- and 6#-fluoro-17#-hydroxy- 17α - methyl - 5 - oxo - 3,5 - seco - A - nor - androstan-3-oic acid methyl ester is prepared from 6α- bromo - 17# - hydroxy - 17α - methyl - 5 - oxo - 3,5- seco - A - nor - androstan - 3 - oic acid methyl ester, the last-named compound being prepared by esterification of the corresponding 3-oic acid with diazomethane.
[GB1247022A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68030867A | 1967-11-03 | 1967-11-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33567L true IE33567L (en) | 1969-05-03 |
| IE33567B1 IE33567B1 (en) | 1974-08-21 |
Family
ID=24730576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1298/68A IE33567B1 (en) | 1967-11-03 | 1968-10-29 | 4-oxa-androstanes and process for the manufacture thereof |
Country Status (14)
| Country | Link |
|---|---|
| AT (2) | AT287932B (en) |
| BE (1) | BE723189A (en) |
| BR (1) | BR6803654D0 (en) |
| CH (1) | CH505855A (en) |
| DK (1) | DK131576C (en) |
| ES (1) | ES359842A1 (en) |
| FI (1) | FI48098C (en) |
| FR (2) | FR8435M (en) |
| GB (1) | GB1247022A (en) |
| IE (1) | IE33567B1 (en) |
| IL (1) | IL30879A (en) |
| NL (1) | NL6815623A (en) |
| NO (1) | NO132101C (en) |
| SE (1) | SE352360B (en) |
-
1968
- 1968-10-16 IL IL30879A patent/IL30879A/en unknown
- 1968-10-21 CH CH1567068A patent/CH505855A/en not_active IP Right Cessation
- 1968-10-29 IE IE1298/68A patent/IE33567B1/en unknown
- 1968-10-30 DK DK527668A patent/DK131576C/en active
- 1968-10-31 AT AT1062768A patent/AT287932B/en not_active IP Right Cessation
- 1968-10-31 FR FR172161A patent/FR8435M/fr not_active Expired
- 1968-10-31 AT AT416970A patent/AT297236B/en not_active IP Right Cessation
- 1968-10-31 SE SE14758/68A patent/SE352360B/xx unknown
- 1968-10-31 FR FR172162A patent/FR1605466A/fr not_active Expired
- 1968-10-31 BE BE723189D patent/BE723189A/xx unknown
- 1968-11-01 GB GB29584/70A patent/GB1247022A/en not_active Expired
- 1968-11-01 BR BR203654/68A patent/BR6803654D0/en unknown
- 1968-11-01 NL NL6815623A patent/NL6815623A/xx unknown
- 1968-11-01 NO NO4350/68A patent/NO132101C/no unknown
- 1968-11-02 ES ES359842A patent/ES359842A1/en not_active Expired
- 1968-11-04 FI FI683140A patent/FI48098C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NO132101C (en) | 1975-09-17 |
| FI48098B (en) | 1974-02-28 |
| AT297236B (en) | 1972-03-10 |
| BE723189A (en) | 1969-04-30 |
| FR1605466A (en) | 1976-05-14 |
| DK131576C (en) | 1976-01-05 |
| FI48098C (en) | 1974-06-10 |
| AT287932B (en) | 1971-02-10 |
| DK131576B (en) | 1975-08-04 |
| FR8435M (en) | 1971-07-15 |
| IL30879A (en) | 1972-11-28 |
| NL6815623A (en) | 1969-05-06 |
| ES359842A1 (en) | 1970-06-16 |
| CH505855A (en) | 1971-04-15 |
| NO132101B (en) | 1975-06-09 |
| GB1247022A (en) | 1971-09-22 |
| SE352360B (en) | 1972-12-27 |
| IL30879A0 (en) | 1968-12-26 |
| DE1805857A1 (en) | 1969-06-26 |
| DE1805857B2 (en) | 1977-06-23 |
| IE33567B1 (en) | 1974-08-21 |
| BR6803654D0 (en) | 1973-01-16 |
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