DE2216495A1 - Trialkylsilyläther der 17 alpha-Alkinylöstra-l,3,5-(10)-trien-3,17 beta-diole und deren 11 beta-Alkylderivate, Verfahren zur Herstellung dieser Verbindungen und ihre Verwendung - Google Patents
Trialkylsilyläther der 17 alpha-Alkinylöstra-l,3,5-(10)-trien-3,17 beta-diole und deren 11 beta-Alkylderivate, Verfahren zur Herstellung dieser Verbindungen und ihre VerwendungInfo
- Publication number
- DE2216495A1 DE2216495A1 DE19722216495 DE2216495A DE2216495A1 DE 2216495 A1 DE2216495 A1 DE 2216495A1 DE 19722216495 DE19722216495 DE 19722216495 DE 2216495 A DE2216495 A DE 2216495A DE 2216495 A1 DE2216495 A1 DE 2216495A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butyl
- dimethylsilyloxy
- triene
- trien
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 46
- -1 Trialkylsilyl ethers Chemical class 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 6
- 241001465754 Metazoa Species 0.000 claims description 27
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 241000283984 Rodentia Species 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 5
- 150000003431 steroids Chemical class 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 229910021419 crystalline silicon Inorganic materials 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000002345 steroid group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
- 241000700159 Rattus Species 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
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- 239000000047 product Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
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- 241000699670 Mus sp. Species 0.000 description 5
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- 235000013339 cereals Nutrition 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
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- 230000001076 estrogenic effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
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- 230000016087 ovulation Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229960001124 trientine Drugs 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- 102000006771 Gonadotropins Human genes 0.000 description 1
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- 241000699709 Microtus Species 0.000 description 1
- 241000520221 Millardia Species 0.000 description 1
- 241000699729 Muridae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- 241000499390 Nesokia Species 0.000 description 1
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- 230000009471 action Effects 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- KEGKKCSRXHJCKP-UHFFFAOYSA-N chloro-ethyl-methyl-propylsilane Chemical compound CCC[Si](C)(Cl)CC KEGKKCSRXHJCKP-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
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- JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 235000013312 flour Nutrition 0.000 description 1
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- 230000035929 gnawing Effects 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
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- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
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- 230000006651 lactation Effects 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
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- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
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- 230000001817 pituitary effect Effects 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
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Classifications
-
- 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
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13215271A | 1971-04-07 | 1971-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2216495A1 true DE2216495A1 (de) | 1972-10-19 |
Family
ID=22452727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722216495 Pending DE2216495A1 (de) | 1971-04-07 | 1972-04-06 | Trialkylsilyläther der 17 alpha-Alkinylöstra-l,3,5-(10)-trien-3,17 beta-diole und deren 11 beta-Alkylderivate, Verfahren zur Herstellung dieser Verbindungen und ihre Verwendung |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3755384A (OSRAM) |
| JP (1) | JPS5516160B2 (OSRAM) |
| AU (1) | AU463573B2 (OSRAM) |
| BE (1) | BE781799A (OSRAM) |
| CA (1) | CA969538A (OSRAM) |
| CH (1) | CH583250A5 (OSRAM) |
| DE (1) | DE2216495A1 (OSRAM) |
| DK (1) | DK129584B (OSRAM) |
| ES (1) | ES401515A1 (OSRAM) |
| FI (1) | FI56846C (OSRAM) |
| FR (1) | FR2132721B1 (OSRAM) |
| GB (1) | GB1367735A (OSRAM) |
| IE (1) | IE36260B1 (OSRAM) |
| IL (1) | IL39145A (OSRAM) |
| IT (1) | IT960311B (OSRAM) |
| NL (1) | NL7204603A (OSRAM) |
| SE (2) | SE376767B (OSRAM) |
| ZA (1) | ZA722343B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9311686D0 (en) * | 1993-06-05 | 1993-07-21 | Monocon Int Ltd | Vessel repair |
| AU1855201A (en) * | 1999-11-02 | 2001-05-14 | Schering Aktiengesellschaft | 18-nor-steroids as selectively active estrogens |
| US6958327B1 (en) | 1999-11-02 | 2005-10-25 | Schering, Ag | 18 Norsteroids as selectively active estrogens |
| US20050282791A1 (en) * | 1999-11-02 | 2005-12-22 | Alexander Hillisch | 18-nor steroids as selectively active estrogens |
-
1971
- 1971-04-07 US US00132152A patent/US3755384A/en not_active Expired - Lifetime
-
1972
- 1972-04-04 IT IT89515/72A patent/IT960311B/it active
- 1972-04-06 GB GB1583872A patent/GB1367735A/en not_active Expired
- 1972-04-06 SE SE7204409A patent/SE376767B/xx unknown
- 1972-04-06 DE DE19722216495 patent/DE2216495A1/de active Pending
- 1972-04-06 ES ES401515A patent/ES401515A1/es not_active Expired
- 1972-04-06 FR FR7212127A patent/FR2132721B1/fr not_active Expired
- 1972-04-06 JP JP3395772A patent/JPS5516160B2/ja not_active Expired
- 1972-04-06 IE IE443/72A patent/IE36260B1/xx unknown
- 1972-04-06 CH CH503672A patent/CH583250A5/xx not_active IP Right Cessation
- 1972-04-06 NL NL7204603A patent/NL7204603A/xx not_active Application Discontinuation
- 1972-04-06 FI FI942/72A patent/FI56846C/fi active
- 1972-04-06 DK DK167272AA patent/DK129584B/da unknown
- 1972-04-06 CA CA139,063A patent/CA969538A/en not_active Expired
- 1972-04-06 IL IL39145A patent/IL39145A/xx unknown
- 1972-04-07 ZA ZA722343A patent/ZA722343B/xx unknown
- 1972-04-07 BE BE781799A patent/BE781799A/xx not_active IP Right Cessation
-
1974
- 1974-04-07 AU AU40888/72A patent/AU463573B2/en not_active Expired
- 1974-08-19 SE SE7410509A patent/SE396271B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL39145A (en) | 1975-05-22 |
| IE36260B1 (en) | 1976-09-29 |
| DK129584C (OSRAM) | 1975-04-07 |
| CA969538A (en) | 1975-06-17 |
| ZA722343B (en) | 1973-06-27 |
| DK129584B (da) | 1974-10-28 |
| AU4088872A (en) | 1973-10-11 |
| FR2132721B1 (OSRAM) | 1975-10-31 |
| ES401515A1 (es) | 1975-05-01 |
| IE36260L (en) | 1972-10-07 |
| JPS5516160B2 (OSRAM) | 1980-04-30 |
| JPS4856660A (OSRAM) | 1973-08-09 |
| FR2132721A1 (OSRAM) | 1972-11-24 |
| NL7204603A (OSRAM) | 1972-10-10 |
| SE7410509L (OSRAM) | 1974-08-19 |
| FI56846C (fi) | 1980-04-10 |
| IT960311B (it) | 1973-11-20 |
| US3755384A (en) | 1973-08-28 |
| BE781799A (fr) | 1972-10-09 |
| CH583250A5 (OSRAM) | 1976-12-31 |
| SE396271B (sv) | 1977-09-19 |
| IL39145A0 (en) | 1972-06-28 |
| AU463573B2 (en) | 1975-07-14 |
| SE376767B (OSRAM) | 1975-06-09 |
| FI56846B (fi) | 1979-12-31 |
| GB1367735A (en) | 1974-09-25 |
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