ES285708A1 - A procedure for the preparation of steroid and related compounds (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for the preparation of steroid and related compounds (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES285708A1 ES285708A1 ES285708A ES285708A ES285708A1 ES 285708 A1 ES285708 A1 ES 285708A1 ES 285708 A ES285708 A ES 285708A ES 285708 A ES285708 A ES 285708A ES 285708 A1 ES285708 A1 ES 285708A1
- Authority
- ES
- Spain
- Prior art keywords
- oxo
- carboxylic acid
- organic carboxylic
- acid
- indane
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 150000003431 steroids Chemical class 0.000 title abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 5
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- HXZILEQYFQYQCE-UHFFFAOYSA-N 2-methylcyclopentane-1,3-dione Chemical compound CC1C(=O)CCC1=O HXZILEQYFQYQCE-UHFFFAOYSA-N 0.000 abstract 1
- ISDUIDRCFYENQN-UHFFFAOYSA-N 5-oxohept-6-enoic acid Chemical compound OC(=O)CCCC(=O)C=C ISDUIDRCFYENQN-UHFFFAOYSA-N 0.000 abstract 1
- QFYWYCZNMLSZOA-UHFFFAOYSA-N CCCCC[Mg] Chemical compound CCCCC[Mg] QFYWYCZNMLSZOA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 125000000422 delta-lactone group Chemical group 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61K31/567—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 position 17 alpha, e.g. mestranol, norethandrolone
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
- C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/38—Unsaturated compounds containing keto groups
-
- 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
- C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method of preparing steroids and related compounds, characterized in that a lower alkyl ester of 5-oxo-6-heptenoic acid is condensed with 1,3-dioxo-2-methylcyclopentane, in the presence of an alkaline condensation agent, the condensation product is treated with an acid or an acid-base system, there is obtained 1,5-dioxo 4- (2'-carboxy-ethyl) 7a-methyl-5,6,7,7-tetrahydro-indane, which it is unfolded with the help of an optically active base in its optical antipodes, the synthesis is continued on the dextrorotatory isomer (in water), the ketone is reduced in position 1 of this last product, with the help of a mixed hydride, the product is subjected reduced 1beta-hidoxy 5-oxo 4- (2'-carboxyethyl) 7abeta-methyl-5,6,7,7a-tetrahydro-indane or an ester of organic carboxylic acid lower than this, to catalytic hydrogenation, is subjected in the case of the presence of ester function in 1, to a treatment with alkalis, and the 1beta-hydroxy 5-oxo 4- (2'- carboxyethyl) 7abeta-methyl 3aalpha, 4beta, 5,6,7,7a-hexahydro-indane, which is transformed with the aid of the anhydride of a lower organic carboxylic acid in delta-lactone of 1beta-OR "4- (2'- carboxyethyl) 5-hydroxy-7-beta-methyl-3-alpha, 4-beta, 7, 7-tetrahydro-indane, where R "is the remainder of the lower organic carboxylic acid employed in the anhydride form, the latter compound is reacted with a 4-oxo halide. pentyl magnesium whose ketone function is previously protected in the form of a ketal, the reaction product is treated with an alkaline agent, is then subjected to acid hydrolysis and 3.5-dioxo-17-hydroxy-4,5-dry is obtained delta9-premiere, which is processed according to the procedures into 3-oxo-17beta-hydroxy-delta-4,-estradiene, into an ester of organic carboxylic acid having from 1 to 18 carbon atoms thereof, or into 3-oxo-17-beta-acyloxy delta4-premiere, the radical acyl representing the rest of an organic carboxylic acid that has e from 1 to 18 carbon atoms. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR890184A FR1364556A (en) | 1962-03-06 | 1962-03-06 | New process for the synthesis of steroids and related compounds and products used in this process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES285708A1 true ES285708A1 (en) | 1963-06-01 |
Family
ID=8774160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES285708A Expired ES285708A1 (en) | 1962-03-06 | 1963-03-04 | A procedure for the preparation of steroid and related compounds (Machine-translation by Google Translate, not legally binding) |
Country Status (5)
| Country | Link |
|---|---|
| AT (6) | AT253691B (en) |
| DE (1) | DE1290937B (en) |
| DK (1) | DK107742C (en) |
| ES (1) | ES285708A1 (en) |
| FR (1) | FR1364556A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1446408A (en) * | 1965-06-09 | 1966-07-22 | Roussel Uclaf | New process for the preparation of certain indane derivatives |
| FR1506347A (en) * | 1966-07-27 | 1967-12-22 | Roussel Uclaf | New optically active compounds, of bicyclic structure, and method of preparation |
| CA977351A (en) * | 1968-10-04 | 1975-11-04 | Zoltan G. Hajos | Tricyclic compounds and their manufacture |
| US3897460A (en) * | 1968-10-04 | 1975-07-29 | Hoffmann La Roche | 3{62 -Tertiarybutoxy-decahydro-benz{8 E{9 indenes |
-
1962
- 1962-03-06 FR FR890184A patent/FR1364556A/en not_active Expired
-
1963
- 1963-03-04 ES ES285708A patent/ES285708A1/en not_active Expired
- 1963-03-05 DE DE1963R0034611 patent/DE1290937B/en active Pending
- 1963-03-06 AT AT176063A patent/AT253691B/en active
- 1963-03-06 DK DK102763A patent/DK107742C/en active
- 1963-03-06 AT AT175863A patent/AT258484B/en active
- 1963-03-06 AT AT176163A patent/AT253692B/en active
- 1963-03-06 AT AT901665A patent/AT266345B/en active
- 1963-03-06 AT AT175963A patent/AT253690B/en active
- 1963-03-06 AT AT176263A patent/AT253693B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT266345B (en) | 1968-11-11 |
| AT253693B (en) | 1967-04-25 |
| FR1364556A (en) | 1964-06-26 |
| AT253690B (en) | 1967-04-25 |
| AT253692B (en) | 1967-04-25 |
| AT253691B (en) | 1967-04-25 |
| AT258484B (en) | 1967-11-27 |
| DE1290937B (en) | 1969-03-20 |
| DK107742C (en) | 1967-07-03 |
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