DE1643022B2 - Verfahren zur herstellung von 21- estern der 11 alpha, 21-dihydroxysteroide mit einem verzweigtkettigen esterrest in 21-stellung sowie entsprechende 6 alpha-fluor-11 alpha-hydroxy-21-acyloxy- 16 alpha-methyl-1,4-pregnadien-3,20-dion- zwischenprodukte - Google Patents
Verfahren zur herstellung von 21- estern der 11 alpha, 21-dihydroxysteroide mit einem verzweigtkettigen esterrest in 21-stellung sowie entsprechende 6 alpha-fluor-11 alpha-hydroxy-21-acyloxy- 16 alpha-methyl-1,4-pregnadien-3,20-dion- zwischenprodukteInfo
- Publication number
- DE1643022B2 DE1643022B2 DE1967SC040711 DESC040711A DE1643022B2 DE 1643022 B2 DE1643022 B2 DE 1643022B2 DE 1967SC040711 DE1967SC040711 DE 1967SC040711 DE SC040711 A DESC040711 A DE SC040711A DE 1643022 B2 DE1643022 B2 DE 1643022B2
- Authority
- DE
- Germany
- Prior art keywords
- alpha
- hydroxy
- acyloxy
- branched
- esterification
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 9
- 229920004518 DION® Polymers 0.000 title 1
- 150000002148 esters Chemical group 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- 230000032050 esterification Effects 0.000 claims description 16
- 238000005886 esterification reaction Methods 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- -1 steroid alcohols Chemical class 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- GUHFLRTWNHWJBS-VLTGGNAYSA-N (8r,9s,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1C1=CC=C(C(=O)C)[C@@]1(C)CC2 GUHFLRTWNHWJBS-VLTGGNAYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond 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)
- Gates (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967SC040711 DE1643022B2 (de) | 1967-05-13 | 1967-05-13 | Verfahren zur herstellung von 21- estern der 11 alpha, 21-dihydroxysteroide mit einem verzweigtkettigen esterrest in 21-stellung sowie entsprechende 6 alpha-fluor-11 alpha-hydroxy-21-acyloxy- 16 alpha-methyl-1,4-pregnadien-3,20-dion- zwischenprodukte |
| DE19681668691 DE1668691A1 (de) | 1967-05-13 | 1968-03-12 | Verfahren zur Herstellung von 21-Estern der 11alpha,21-Dihydroxysteroide |
| DK197568AA DK127384B (da) | 1967-05-13 | 1968-04-29 | Fremgangsmåde til fremstilling af 11α-hydroxy-21-acyloxy-steroider. |
| CH659868A CH517085A (de) | 1967-05-13 | 1968-05-03 | Verfahren zur Herstellung von 21-Estern der 11a,21-Dihydroxysteroide |
| AT454868A AT312819B (de) | 1967-05-13 | 1968-05-10 | Verfahren zur Herstellung von 11α-Hydroxy-21-acyloxysteroiden |
| SE06368/68A SE351631B (cs) | 1967-05-13 | 1968-05-10 | |
| NO01818/68A NO129678B (cs) | 1967-05-13 | 1968-05-10 | |
| ES353766A ES353766A1 (es) | 1967-05-13 | 1968-05-10 | Procedimiento de fabricacion de 11-alfahidroxi-21-aciloxi- esteroides. |
| FR1561884D FR1561884A (cs) | 1967-05-13 | 1968-05-10 | |
| IT16380/68A IT1047870B (it) | 1967-05-13 | 1968-05-11 | Procedimento per preparare degli esteri in posizione 21 degli 11 21 diidrossisteroidi |
| NL6806774.A NL159992C (nl) | 1967-05-13 | 1968-05-13 | Werkwijze ter bereiding van 21-acyloxy-11alpha-hydroxy- -pregnaanderivaten. |
| JP43031842A JPS5141634B1 (cs) | 1967-05-13 | 1968-05-13 | |
| BE715064D BE715064A (cs) | 1967-05-13 | 1968-05-13 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967SC040711 DE1643022B2 (de) | 1967-05-13 | 1967-05-13 | Verfahren zur herstellung von 21- estern der 11 alpha, 21-dihydroxysteroide mit einem verzweigtkettigen esterrest in 21-stellung sowie entsprechende 6 alpha-fluor-11 alpha-hydroxy-21-acyloxy- 16 alpha-methyl-1,4-pregnadien-3,20-dion- zwischenprodukte |
| DESC042090 | 1968-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1643022A1 DE1643022A1 (de) | 1971-01-21 |
| DE1643022B2 true DE1643022B2 (de) | 1976-12-30 |
Family
ID=25993465
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967SC040711 Granted DE1643022B2 (de) | 1967-05-13 | 1967-05-13 | Verfahren zur herstellung von 21- estern der 11 alpha, 21-dihydroxysteroide mit einem verzweigtkettigen esterrest in 21-stellung sowie entsprechende 6 alpha-fluor-11 alpha-hydroxy-21-acyloxy- 16 alpha-methyl-1,4-pregnadien-3,20-dion- zwischenprodukte |
| DE19681668691 Pending DE1668691A1 (de) | 1967-05-13 | 1968-03-12 | Verfahren zur Herstellung von 21-Estern der 11alpha,21-Dihydroxysteroide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681668691 Pending DE1668691A1 (de) | 1967-05-13 | 1968-03-12 | Verfahren zur Herstellung von 21-Estern der 11alpha,21-Dihydroxysteroide |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5141634B1 (cs) |
| AT (1) | AT312819B (cs) |
| BE (1) | BE715064A (cs) |
| CH (1) | CH517085A (cs) |
| DE (2) | DE1643022B2 (cs) |
| DK (1) | DK127384B (cs) |
| ES (1) | ES353766A1 (cs) |
| FR (1) | FR1561884A (cs) |
| IT (1) | IT1047870B (cs) |
| NL (1) | NL159992C (cs) |
| NO (1) | NO129678B (cs) |
| SE (1) | SE351631B (cs) |
-
1967
- 1967-05-13 DE DE1967SC040711 patent/DE1643022B2/de active Granted
-
1968
- 1968-03-12 DE DE19681668691 patent/DE1668691A1/de active Pending
- 1968-04-29 DK DK197568AA patent/DK127384B/da unknown
- 1968-05-03 CH CH659868A patent/CH517085A/de not_active IP Right Cessation
- 1968-05-10 ES ES353766A patent/ES353766A1/es not_active Expired
- 1968-05-10 SE SE06368/68A patent/SE351631B/xx unknown
- 1968-05-10 FR FR1561884D patent/FR1561884A/fr not_active Expired
- 1968-05-10 NO NO01818/68A patent/NO129678B/no unknown
- 1968-05-10 AT AT454868A patent/AT312819B/de not_active IP Right Cessation
- 1968-05-11 IT IT16380/68A patent/IT1047870B/it active
- 1968-05-13 BE BE715064D patent/BE715064A/xx unknown
- 1968-05-13 JP JP43031842A patent/JPS5141634B1/ja active Pending
- 1968-05-13 NL NL6806774.A patent/NL159992C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL159992C (nl) | 1979-09-17 |
| DE1643022A1 (de) | 1971-01-21 |
| AT312819B (de) | 1974-01-25 |
| DE1668691A1 (de) | 1971-06-03 |
| CH517085A (de) | 1971-12-31 |
| JPS5141634B1 (cs) | 1976-11-11 |
| NO129678B (cs) | 1974-05-13 |
| SE351631B (cs) | 1972-12-04 |
| FR1561884A (cs) | 1969-03-28 |
| BE715064A (cs) | 1968-11-13 |
| IT1047870B (it) | 1980-10-20 |
| ES353766A1 (es) | 1970-02-01 |
| NL6806774A (cs) | 1968-11-14 |
| DK127384B (da) | 1973-10-29 |
| NL159992B (nl) | 1979-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |