CH536293A - Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids - Google Patents
Verfahren zur Herstellung eines neuen östrogen hochwirksamen SteroidsInfo
- Publication number
- CH536293A CH536293A CH1870172A CH1870172A CH536293A CH 536293 A CH536293 A CH 536293A CH 1870172 A CH1870172 A CH 1870172A CH 1870172 A CH1870172 A CH 1870172A CH 536293 A CH536293 A CH 536293A
- Authority
- CH
- Switzerland
- Prior art keywords
- alpha
- methyl
- oestrogenic
- ether
- cyclopentyl
- Prior art date
Links
- 230000001076 estrogenic effect Effects 0.000 title abstract description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- -1 3-cyclopentyloxy steroid Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims 1
- 230000001836 utereotrophic effect Effects 0.000 abstract description 4
- 229960002568 ethinylestradiol Drugs 0.000 abstract description 3
- 238000002513 implantation Methods 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 210000001109 blastomere Anatomy 0.000 abstract description 2
- 230000035558 fertility Effects 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 150000001247 metal acetylides Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010067572 Oestrogenic effect Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000027326 copulation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 1
- ORTYMGHCFWKXHO-UHFFFAOYSA-N diethadione Chemical compound CCC1(CC)COC(=O)NC1=O ORTYMGHCFWKXHO-UHFFFAOYSA-N 0.000 description 1
- 229960003675 diethadione Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000000624 ovulatory effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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
- 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)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- General Health & Medical Sciences (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 |
|---|---|---|---|
| CH1870172A CH536293A (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 |
|---|---|---|---|
| CH1870172A CH536293A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids |
| CH621870A CH536291A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen, östrogen hochwirksamen Steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH536293A true CH536293A (de) | 1973-04-30 |
Family
ID=4306140
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1870172A CH536293A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids |
| CH621870A CH536291A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen, östrogen hochwirksamen Steroids |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH621870A CH536291A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen, östrogen hochwirksamen Steroids |
Country Status (19)
| Country | Link |
|---|---|
| AT (2) | AT315394B (cs) |
| BE (1) | BE766183A (cs) |
| CA (1) | CA921022A (cs) |
| CH (2) | CH536293A (cs) |
| CS (2) | CS161776B2 (cs) |
| DE (1) | DE2118997A1 (cs) |
| DK (2) | DK129580B (cs) |
| ES (2) | ES390460A1 (cs) |
| FI (1) | FI48826C (cs) |
| FR (1) | FR2092081B1 (cs) |
| GB (1) | GB1330072A (cs) |
| HU (1) | HU162383B (cs) |
| IE (1) | IE35146B1 (cs) |
| IL (1) | IL36653A (cs) |
| NL (1) | NL7105577A (cs) |
| PL (2) | PL83828B1 (cs) |
| SE (1) | SE373576B (cs) |
| SU (2) | SU399116A3 (cs) |
| ZA (1) | ZA712524B (cs) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1434174A (fr) * | 1963-12-24 | 1966-04-08 | Ciba Geigy | Procédé de préparation de nouveaux stéroïdes de la série de l'oestrane |
| BE755689A (fr) * | 1969-09-03 | 1971-03-03 | Upjohn Co | Procede de fabrication de nouvelles 7 beta-alkyl-19- nortestosterones |
-
1970
- 1970-04-24 CH CH1870172A patent/CH536293A/de not_active IP Right Cessation
- 1970-04-24 CH CH621870A patent/CH536291A/de not_active IP Right Cessation
-
1971
- 1971-04-19 CA CA110655A patent/CA921022A/en not_active Expired
- 1971-04-19 IL IL36653A patent/IL36653A/xx unknown
- 1971-04-20 ZA ZA712524A patent/ZA712524B/xx unknown
- 1971-04-20 DE DE19712118997 patent/DE2118997A1/de active Pending
- 1971-04-20 IE IE490/71A patent/IE35146B1/xx unknown
- 1971-04-21 GB GB1042871*[A patent/GB1330072A/en not_active Expired
- 1971-04-22 ES ES390460A patent/ES390460A1/es not_active Expired
- 1971-04-22 PL PL1971178220A patent/PL83828B1/pl unknown
- 1971-04-22 HU HUCI1105A patent/HU162383B/hu unknown
- 1971-04-22 FR FR7114321A patent/FR2092081B1/fr not_active Expired
- 1971-04-22 PL PL1971147686A patent/PL71122B1/pl unknown
- 1971-04-23 SE SE7105302A patent/SE373576B/xx unknown
- 1971-04-23 CS CS1883A patent/CS161776B2/cs unknown
- 1971-04-23 DK DK197071AA patent/DK129580B/da unknown
- 1971-04-23 SU SU711649254D patent/SU399116A3/ru active
- 1971-04-23 CS CS2985A patent/CS161775B2/cs unknown
- 1971-04-23 BE BE766183A patent/BE766183A/xx unknown
- 1971-04-23 AT AT234272A patent/AT315394B/de not_active IP Right Cessation
- 1971-04-23 NL NL7105577A patent/NL7105577A/xx unknown
- 1971-04-23 FI FI711130A patent/FI48826C/fi active
- 1971-04-23 AT AT351071A patent/AT306261B/de not_active IP Right Cessation
- 1971-04-23 SU SU1649254A patent/SU383287A3/ru active
-
1972
- 1972-08-18 DK DK412072AA patent/DK128316B/da unknown
-
1973
- 1973-07-16 ES ES416953A patent/ES416953A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL36653A (en) | 1974-07-31 |
| FI48826B (cs) | 1974-09-30 |
| GB1330072A (en) | 1973-09-12 |
| DE2118997A1 (de) | 1971-11-11 |
| IL36653A0 (en) | 1971-06-23 |
| ZA712524B (en) | 1972-01-26 |
| DK128316B (da) | 1974-04-08 |
| AT315394B (de) | 1974-05-27 |
| FR2092081A1 (cs) | 1972-01-21 |
| CS161775B2 (cs) | 1975-06-10 |
| IE35146L (en) | 1971-10-24 |
| ES416953A1 (es) | 1976-03-16 |
| ES390460A1 (es) | 1974-07-01 |
| CH536291A (de) | 1973-04-30 |
| HU162383B (cs) | 1973-02-28 |
| SU399116A3 (cs) | 1973-09-27 |
| SU383287A3 (cs) | 1973-05-25 |
| IE35146B1 (en) | 1975-11-26 |
| CS161776B2 (cs) | 1975-06-10 |
| DK129580B (da) | 1974-10-28 |
| SE373576B (sv) | 1975-02-10 |
| PL71122B1 (cs) | 1974-04-30 |
| FR2092081B1 (cs) | 1974-10-18 |
| NL7105577A (cs) | 1971-10-26 |
| CA921022A (en) | 1973-02-13 |
| DK129580C (cs) | 1975-04-28 |
| BE766183A (fr) | 1971-10-25 |
| PL83828B1 (cs) | 1976-02-28 |
| AT306261B (de) | 1973-04-10 |
| FI48826C (fi) | 1975-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |