DE1668611B1 - 3-(ss-Diaethylaminoaethoxy)-16-oxo-delta?-OEstratrien,3-(ss-Diaethylaminoaethoxy)-17-oxo-delta?-lumi-oestratrien und deren Chlorhydrate und Verfahren zu deren Herstellung - Google Patents
3-(ss-Diaethylaminoaethoxy)-16-oxo-delta?-OEstratrien,3-(ss-Diaethylaminoaethoxy)-17-oxo-delta?-lumi-oestratrien und deren Chlorhydrate und Verfahren zu deren HerstellungInfo
- Publication number
- DE1668611B1 DE1668611B1 DE19621668611D DE1668611DA DE1668611B1 DE 1668611 B1 DE1668611 B1 DE 1668611B1 DE 19621668611 D DE19621668611 D DE 19621668611D DE 1668611D A DE1668611D A DE 1668611DA DE 1668611 B1 DE1668611 B1 DE 1668611B1
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- diethylaminoethoxy
- oestratriene
- diaethylaminoaethoxy
- delta
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 230000001076 estrogenic effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 2
- DNXHEGUUPJUMQT-XLMAVXFVSA-N (8r,9s,13r,14s)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-one Chemical compound OC1=CC=C2[C@H]3CC[C@@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-XLMAVXFVSA-N 0.000 description 2
- 206010067572 Oestrogenic effect Diseases 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000000260 hypercholesteremic effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002402 anti-lipaemic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0072—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the A ring of the steroid being aromatic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR870686A FR1338308A (fr) | 1961-08-11 | 1961-08-11 | Stéroïdes aromatiques substitués en position 3 et procédé de préparation |
| FR923333A FR90803E (fr) | 1961-08-11 | 1963-01-31 | Stéroïdes aromatiques substitués en position 3 et procédé de préparation |
| FR941608A FR90804E (fr) | 1961-08-11 | 1963-07-16 | Stéroïdes aromatiques substitués en position 3 et procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1668611B1 true DE1668611B1 (de) | 1971-10-28 |
Family
ID=27246137
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621468517D Pending DE1468517B1 (de) | 1961-08-11 | 1962-07-27 | Steroide der OEstranreihe und Verfahren zu deren Herstellung |
| DE19621668611D Pending DE1668611B1 (de) | 1961-08-11 | 1962-07-27 | 3-(ss-Diaethylaminoaethoxy)-16-oxo-delta?-OEstratrien,3-(ss-Diaethylaminoaethoxy)-17-oxo-delta?-lumi-oestratrien und deren Chlorhydrate und Verfahren zu deren Herstellung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621468517D Pending DE1468517B1 (de) | 1961-08-11 | 1962-07-27 | Steroide der OEstranreihe und Verfahren zu deren Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3212971A (OSRAM) |
| BE (1) | BE621301A (OSRAM) |
| CH (1) | CH411855A (OSRAM) |
| DE (2) | DE1468517B1 (OSRAM) |
| FR (2) | FR90803E (OSRAM) |
| GB (1) | GB974147A (OSRAM) |
| NL (2) | NL281624A (OSRAM) |
| SE (1) | SE306531B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1025576A (en) * | 1964-10-21 | 1966-04-14 | Parke Davis & Co | Estratriene amino-ethers |
| GB1025919A (en) * | 1965-01-25 | 1966-04-14 | Parke Davis & Co | Estra-1,3,5(10)-triene derivatives |
| US3496167A (en) * | 1968-04-03 | 1970-02-17 | Parke Davis & Co | Estratriene 3-(1-phenyl-1h-tetrazol-5-yl) ethers |
| FR2717690B1 (fr) * | 1994-03-24 | 1996-04-26 | Roussel Uclaf | Application de stéroïdes aromatiques 3 substitués par un aminoalcoxy substitué à l'obtention d'un médicament pour contrôler la stérilité, notamment masculine. |
| US7687486B2 (en) * | 2003-04-29 | 2010-03-30 | Florida Agricultural & Mechanical University | Selective estrogen receptor modulators |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060204A (en) * | 1961-12-01 | 1962-10-23 | American Cyanamid Co | Substituted androst-5-enes, salts and methods of preparing the same |
-
0
- NL NL120166D patent/NL120166C/xx active
- BE BE621301D patent/BE621301A/xx unknown
- NL NL281624D patent/NL281624A/xx unknown
-
1962
- 1962-07-25 CH CH893462A patent/CH411855A/fr unknown
- 1962-07-27 DE DE19621468517D patent/DE1468517B1/de active Pending
- 1962-07-27 DE DE19621668611D patent/DE1668611B1/de active Pending
- 1962-07-27 US US213036A patent/US3212971A/en not_active Expired - Lifetime
- 1962-07-27 SE SE8334/62A patent/SE306531B/xx unknown
- 1962-08-10 GB GB30826/62A patent/GB974147A/en not_active Expired
-
1963
- 1963-01-31 FR FR923333A patent/FR90803E/fr not_active Expired
- 1963-07-16 FR FR941608A patent/FR90804E/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1468517B1 (de) | 1972-05-31 |
| GB974147A (en) | 1964-11-04 |
| NL281624A (OSRAM) | |
| SE306531B (OSRAM) | 1968-12-02 |
| FR90803E (fr) | 1968-02-23 |
| CH411855A (fr) | 1966-04-30 |
| US3212971A (en) | 1965-10-19 |
| FR90804E (fr) | 1968-02-23 |
| NL120166C (OSRAM) | |
| BE621301A (OSRAM) |
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