CH536290A - Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids - Google Patents
Verfahren zur Herstellung eines neuen östrogen hochwirksamen SteroidsInfo
- Publication number
- CH536290A CH536290A CH1870272A CH1870272A CH536290A CH 536290 A CH536290 A CH 536290A CH 1870272 A CH1870272 A CH 1870272A CH 1870272 A CH1870272 A CH 1870272A CH 536290 A CH536290 A CH 536290A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- formula
- compound
- cyclopentyloxy
- estratriene
- Prior art date
Links
- 230000001076 estrogenic effect Effects 0.000 claims abstract description 6
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims abstract description 6
- 230000001836 utereotrophic effect Effects 0.000 claims abstract description 6
- 238000002513 implantation Methods 0.000 claims abstract description 5
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- 210000001109 blastomere Anatomy 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000035558 fertility Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 241000700159 Rattus Species 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- HLCRYAZDZCJZFG-BDXSIMOUSA-N (8s,9s,13s,14s)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CC=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HLCRYAZDZCJZFG-BDXSIMOUSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000012285 osmium tetroxide Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 230000027326 copulation Effects 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 230000003780 keratinization Effects 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 230000003204 osmotic effect Effects 0.000 claims description 2
- 230000000624 ovulatory effect Effects 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000006894 reductive elimination reaction Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/168—Steroids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/184—Hormones
-
- 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
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Endocrinology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1870272A CH536290A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH621970A CH551959A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur herstellung neuer oestrogen hochwirksamer steroide. |
| CH1870272A CH536290A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH536290A true CH536290A (de) | 1973-04-30 |
Family
ID=4306158
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1870272A CH536290A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids |
| CH1870372A CH536295A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids |
| CH621970A CH551959A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur herstellung neuer oestrogen hochwirksamer steroide. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1870372A CH536295A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids |
| CH621970A CH551959A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur herstellung neuer oestrogen hochwirksamer steroide. |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT312826B (cs) |
| CH (3) | CH536290A (cs) |
| CS (1) | CS157120B2 (cs) |
| SU (1) | SU434651A3 (cs) |
| ZA (1) | ZA712525B (cs) |
-
1970
- 1970-04-24 CH CH1870272A patent/CH536290A/de not_active IP Right Cessation
- 1970-04-24 CH CH1870372A patent/CH536295A/de not_active IP Right Cessation
- 1970-04-24 CH CH621970A patent/CH551959A/de not_active IP Right Cessation
-
1971
- 1971-04-20 ZA ZA712525A patent/ZA712525B/xx unknown
- 1971-04-23 SU SU1815023A patent/SU434651A3/ru active
- 1971-04-23 AT AT273172A patent/AT312826B/de not_active IP Right Cessation
- 1971-04-23 CS CS173973*1A patent/CS157120B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU434651A3 (ru) | 1974-06-30 |
| AT312826B (de) | 1974-01-25 |
| ZA712525B (en) | 1972-01-26 |
| CH536295A (de) | 1973-04-30 |
| CS157120B2 (cs) | 1974-08-23 |
| CH551959A (de) | 1974-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |