ES268249A1 - New steroid compounds and processes for the production thereof - Google Patents
New steroid compounds and processes for the production thereofInfo
- Publication number
- ES268249A1 ES268249A1 ES0268249A ES268249A ES268249A1 ES 268249 A1 ES268249 A1 ES 268249A1 ES 0268249 A ES0268249 A ES 0268249A ES 268249 A ES268249 A ES 268249A ES 268249 A1 ES268249 A1 ES 268249A1
- Authority
- ES
- Spain
- Prior art keywords
- pregnan
- dihydroxy
- hydrogen atom
- oxidation
- processes
- 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
- 238000000034 method Methods 0.000 title abstract 2
- -1 steroid compounds Chemical class 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 2
- WRDWQVFVGGZVOA-VAEALJQBSA-N (3R,5R,8S,9S,10S,13S,14S)-3-hydroxy-17-(2-hydroxyethylidene)-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one Chemical compound O[C@H]1C[C@H]2CC[C@H]3[C@@H]4CCC(=CCO)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C WRDWQVFVGGZVOA-VAEALJQBSA-N 0.000 abstract 1
- QLOWYEXJOFUPQR-JYUSHERBSA-N (3R,5R,8S,9S,10S,13S,14S,17S)-17-(1,3-dihydroxyprop-1-en-2-yl)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one Chemical compound O[C@H]1C[C@H]2CC[C@H]3[C@@H]4CC[C@H](C(CO)=CO)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C QLOWYEXJOFUPQR-JYUSHERBSA-N 0.000 abstract 1
- DIRFKRKDYVZWDV-CWZKNBAESA-N (5s,8s,9s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one Chemical class C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1=O DIRFKRKDYVZWDV-CWZKNBAESA-N 0.000 abstract 1
- VWPIZSZUNBMFBM-JTDCBSPISA-N 2-[(5S,8S,9S,10S,13R,14S,17R)-10,13-dimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]acetaldehyde Chemical class C(C[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O VWPIZSZUNBMFBM-JTDCBSPISA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises a 5b -pregnan -11- one derivative having the formula <FORM:0967078/C1/1> in which R and R1, which may be the same or different, each represent a hydrogen atom or an acyl radical derived from an organic or inorganic acid and R2 represents a hydrogen atom or one of the groups -OR1 or -CH2OR1 where R1 is the previously specified meaning, and processes for the preparation thereof by the oxidation of 3a , 21-dihydroxy -5b - pregn-17 (20)-en -11- one and the optional acylation of the oxidation product to obtain a 5b -pregn-17 (20)-ene-11, 20-dione derivative having the general formula <FORM:0967078/C1/2> (where R indicates a hydrogen atom or an acyl radical) which is reduced to yield the corresponding 5b -pregnane-11, 21-dione derivative which is then reacted in solution in a water-miscible solvent and in the presence of alkali with formaldehyde. Oxidation is preferably effected with manganese dioxide, reduction of the 17(20)-double bond is preferably effected by catalytic hydrogenation in the presence of palladinised charcoal and the treatment with formaldehyde in the presence of calcium hydroxide. From the reaction mixture so obtained there may be isolated by extraction 3a , 21-dihydroxy-20, 20-bis-(hydroxymethylene) -5b - pregnan -11- one and 3a , 21-dihydroxy -20- hydroxymethylene-5b -pregnan -11- one, which may be acylated to form the corresponding tetraacylates and traacylates respectively e.g. by nitration. Specifications 945,503 and 967,080 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR830184A FR1363865A (en) | 1960-06-16 | 1960-06-16 | New polyhydroxylated steroids and obtaining these compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES268249A1 true ES268249A1 (en) | 1961-09-16 |
Family
ID=8733554
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0268248A Expired ES268248A1 (en) | 1960-06-16 | 1961-06-15 | New steroid compounds and processes for the production thereof |
| ES0268247A Expired ES268247A1 (en) | 1960-06-16 | 1961-06-15 | New steroid compounds and processes for the production thereof |
| ES0268249A Expired ES268249A1 (en) | 1960-06-16 | 1961-06-15 | New steroid compounds and processes for the production thereof |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0268248A Expired ES268248A1 (en) | 1960-06-16 | 1961-06-15 | New steroid compounds and processes for the production thereof |
| ES0268247A Expired ES268247A1 (en) | 1960-06-16 | 1961-06-15 | New steroid compounds and processes for the production thereof |
Country Status (5)
| Country | Link |
|---|---|
| CH (3) | CH413831A (en) |
| ES (3) | ES268248A1 (en) |
| FR (4) | FR1363865A (en) |
| GB (2) | GB967078A (en) |
| SE (2) | SE302454B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE027463T2 (en) | 2008-05-28 | 2016-09-28 | Reveragen Biopharma Inc | NF-b non-hormonal steroid modulators for the treatment of disease |
| US10799514B2 (en) | 2015-06-29 | 2020-10-13 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kappa beta for treatment of disease |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
-
1960
- 1960-06-16 FR FR830184A patent/FR1363865A/en not_active Expired
- 1960-08-19 FR FR836270A patent/FR335M/en active Active
- 1960-08-26 FR FR836867A patent/FR342M/en active Active
- 1960-08-26 FR FR836866A patent/FR341M/en active Active
-
1961
- 1961-06-09 SE SE6086/61A patent/SE302454B/xx unknown
- 1961-06-09 SE SE6085/61A patent/SE301966B/xx unknown
- 1961-06-15 ES ES0268248A patent/ES268248A1/en not_active Expired
- 1961-06-15 CH CH699961A patent/CH413831A/en unknown
- 1961-06-15 ES ES0268247A patent/ES268247A1/en not_active Expired
- 1961-06-15 ES ES0268249A patent/ES268249A1/en not_active Expired
- 1961-06-15 CH CH700061A patent/CH411863A/en unknown
- 1961-06-15 CH CH699861A patent/CH418331A/en unknown
- 1961-06-16 GB GB21873/61A patent/GB967078A/en not_active Expired
- 1961-06-16 GB GB48946/63A patent/GB967080A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR342M (en) | 1961-03-27 |
| SE302454B (en) | 1968-07-22 |
| SE301966B (en) | 1968-07-01 |
| CH418331A (en) | 1966-08-15 |
| GB967080A (en) | 1964-08-19 |
| FR341M (en) | 1961-03-27 |
| CH411863A (en) | 1966-04-30 |
| ES268247A1 (en) | 1961-09-16 |
| ES268248A1 (en) | 1961-09-16 |
| FR335M (en) | 1961-03-27 |
| CH413831A (en) | 1966-05-31 |
| FR1363865A (en) | 1964-06-19 |
| GB967078A (en) | 1964-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Friess et al. | Further Observations on the Reaction of Cyclanones with Perbenzoic Acid | |
| ES268247A1 (en) | New steroid compounds and processes for the production thereof | |
| GB965576A (en) | New steroid compounds and processes for their preparation and conversion into isomers thereof | |
| US3038930A (en) | 1, 2, 3, 4, 4a, 9, 10, 10a-octahydro-7-hydroxy-6-methoxy-1, 4a-dimethyl-phenanthrene-1-(carboxylic acid/methanol)and corresponding esters | |
| SATO et al. | The Chemistry of the Spiroaminoketal Side Chain of Solasodine and Tomatidine. I. 1 Improved Preparation of 3β-Acetoxy-5, 16-pregnadien-20-one and 3β-Acetoxy-5α-pregn-16-en-20-one from Solasodine and Tomatidine. | |
| US3959313A (en) | Preparation of dithiolium compounds | |
| US2315817A (en) | Enolesters of the saturated and unsaturated pregnane-20-ones and process for the conversion of acetylene derivatives | |
| US2320847A (en) | delta 5-cholestenone-3 and a method for producing the same | |
| US2919285A (en) | Preparation of 5alpha-pregnane-3, 20-dione from funtumine | |
| GB935610A (en) | 3ªá-amino-pregnane compounds | |
| US2464004A (en) | Stable quinoline salt for electrolysis | |
| US3153090A (en) | Process for the production of oximes | |
| ES269698A1 (en) | New steroid compounds and processes for their preparation | |
| US2517760A (en) | 2-(p-isothiocyanobenzenesulfonamido)-pyrimidine | |
| US2982772A (en) | Octahydro-5ah, 10ah, 4a, 9a-epoxydibenzo-p-dioxin-5a, 10a-diol | |
| US2808415A (en) | Delta4, 8(9)-3, 20-diketo-11, 17-dihydroxy-21-oxygenated-pregnadienes and processes of preparing the same | |
| US2952676A (en) | 17alpha-carboxyalkyl-17beta-hydroxyandros-tan-3-one lactones and nor compounds corresponding | |
| GB943952A (en) | A new steroid compound and its formation | |
| IL38446A (en) | 3,5-dioxo-4,5-seco-gon-9-enes | |
| US3047593A (en) | Preparation of a 3-amino-androstane compound | |
| US2931806A (en) | dl-delta5-3-ethylenedioxy-11-keto-20-cyano pregnenes | |
| ES264322A1 (en) | A PROCEDURE FOR THE PREPARATION OF NEW NITROGEN STEROID COMPOUNDS | |
| GB916951A (en) | New process for the preparation of 6ª--fluoro-steroids | |
| US3002006A (en) | Process of preparing 17alpha-bromo-6alpha-fluoroprogesterone | |
| IL36947A (en) | 3-oxo-17beta-hydroxy-17alpha-ethynyl-estra-(gona)-4,9-dienes and process of preparing same |