DE1924222A1 - Spaltung von aromatischen Steroidalkylaethern - Google Patents
Spaltung von aromatischen SteroidalkylaethernInfo
- Publication number
- DE1924222A1 DE1924222A1 DE19691924222 DE1924222A DE1924222A1 DE 1924222 A1 DE1924222 A1 DE 1924222A1 DE 19691924222 DE19691924222 DE 19691924222 DE 1924222 A DE1924222 A DE 1924222A DE 1924222 A1 DE1924222 A1 DE 1924222A1
- Authority
- DE
- Germany
- Prior art keywords
- cleavage
- alkyl ethers
- aromatic
- acid
- steroidal
- 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
- 238000003776 cleavage reaction Methods 0.000 title claims description 7
- 230000007017 scission Effects 0.000 title claims description 7
- 150000005215 alkyl ethers Chemical class 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 title 1
- 230000003637 steroidlike Effects 0.000 title 1
- -1 aromatic steroid alkyl ethers Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960005309 estradiol Drugs 0.000 description 2
- 229930182833 estradiol Natural products 0.000 description 2
- 229960003399 estrone Drugs 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- XFSUFSQSUUMXLB-UHFFFAOYSA-N propanoic acid;hydrobromide Chemical compound Br.CCC(O)=O XFSUFSQSUUMXLB-UHFFFAOYSA-N 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
- RAGXUPKKYSEPRH-BBCBXFPWSA-N (8R,9S,13S,14S)-13-ethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](CC)(C(CC4)O)[C@@H]4[C@@H]3CCC2=C1 RAGXUPKKYSEPRH-BBCBXFPWSA-N 0.000 description 1
- ULAADVBNYHGIBP-GFEQUFNTSA-N (8r,9s,13s,14s,17s)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol Chemical compound C1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 ULAADVBNYHGIBP-GFEQUFNTSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- PDRGHUMCVRDZLQ-UHFFFAOYSA-N d-equilenin Natural products OC1=CC=C2C(CCC3(C4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-UHFFFAOYSA-N 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- PDRGHUMCVRDZLQ-WMZOPIPTSA-N equilenin Chemical compound OC1=CC=C2C(CC[C@]3([C@H]4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-WMZOPIPTSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691924222 DE1924222A1 (de) | 1969-05-08 | 1969-05-08 | Spaltung von aromatischen Steroidalkylaethern |
| CH611470A CH544079A (de) | 1969-05-08 | 1970-04-23 | Verfahren zur Herstellung von aromatischen Hydroxysteroiden der Östran- oder 19-nor-Pregnanreihe durch Spaltung der entsprechenden aromatischen Steroidalkyläther |
| DK214070A DK126777B (da) | 1969-05-08 | 1970-04-28 | Fremgangsmåde til spaltning af aromatiske steroidalkylætere af østranog pregnanrækken. |
| NL7006657A NL7006657A (enrdf_load_stackoverflow) | 1969-05-08 | 1970-05-06 | |
| JP7038987A JPS5037662B1 (enrdf_load_stackoverflow) | 1969-05-08 | 1970-05-07 | |
| FR7016741A FR2047463A5 (enrdf_load_stackoverflow) | 1969-05-08 | 1970-05-08 | |
| GB2240470A GB1312956A (en) | 1969-05-08 | 1970-05-08 | Process for liberating free hydroxyl groups in steroid ethers |
| BE750162D BE750162A (fr) | 1969-05-08 | 1970-05-08 | Procede de coupure d'alkylethers de steroides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691924222 DE1924222A1 (de) | 1969-05-08 | 1969-05-08 | Spaltung von aromatischen Steroidalkylaethern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1924222A1 true DE1924222A1 (de) | 1970-11-19 |
Family
ID=5733999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691924222 Pending DE1924222A1 (de) | 1969-05-08 | 1969-05-08 | Spaltung von aromatischen Steroidalkylaethern |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5037662B1 (enrdf_load_stackoverflow) |
| BE (1) | BE750162A (enrdf_load_stackoverflow) |
| CH (1) | CH544079A (enrdf_load_stackoverflow) |
| DE (1) | DE1924222A1 (enrdf_load_stackoverflow) |
| DK (1) | DK126777B (enrdf_load_stackoverflow) |
| FR (1) | FR2047463A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1312956A (enrdf_load_stackoverflow) |
| NL (1) | NL7006657A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52106359U (enrdf_load_stackoverflow) * | 1976-02-05 | 1977-08-12 | ||
| JPS5319477U (enrdf_load_stackoverflow) * | 1976-07-27 | 1978-02-18 | ||
| JPH06182007A (ja) * | 1992-12-15 | 1994-07-05 | Bridgestone Corp | ゴルフクラブシャフト |
-
1969
- 1969-05-08 DE DE19691924222 patent/DE1924222A1/de active Pending
-
1970
- 1970-04-23 CH CH611470A patent/CH544079A/de not_active IP Right Cessation
- 1970-04-28 DK DK214070A patent/DK126777B/da unknown
- 1970-05-06 NL NL7006657A patent/NL7006657A/xx unknown
- 1970-05-07 JP JP7038987A patent/JPS5037662B1/ja active Pending
- 1970-05-08 GB GB2240470A patent/GB1312956A/en not_active Expired
- 1970-05-08 FR FR7016741A patent/FR2047463A5/fr not_active Expired
- 1970-05-08 BE BE750162D patent/BE750162A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7006657A (enrdf_load_stackoverflow) | 1970-11-10 |
| DK126777B (da) | 1973-08-20 |
| CH544079A (de) | 1973-11-15 |
| BE750162A (fr) | 1970-11-09 |
| FR2047463A5 (enrdf_load_stackoverflow) | 1971-03-12 |
| JPS5037662B1 (enrdf_load_stackoverflow) | 1975-12-04 |
| GB1312956A (en) | 1973-04-11 |
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