GB1461663A - Process for the preparation of 17-esters of 17alpha,21-dihydroxy steroids of the pregnane series and products obtained - Google Patents
Process for the preparation of 17-esters of 17alpha,21-dihydroxy steroids of the pregnane series and products obtainedInfo
- Publication number
- GB1461663A GB1461663A GB2754374A GB2754374A GB1461663A GB 1461663 A GB1461663 A GB 1461663A GB 2754374 A GB2754374 A GB 2754374A GB 2754374 A GB2754374 A GB 2754374A GB 1461663 A GB1461663 A GB 1461663A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- phosphate
- carboxylic acid
- dihydroxy
- acyloxy
- 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.)
- Expired
Links
- 150000003431 steroids Chemical class 0.000 title abstract 4
- 150000003128 pregnanes Chemical class 0.000 title 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 3
- 239000010452 phosphate Substances 0.000 abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 230000030609 dephosphorylation Effects 0.000 abstract 2
- 238000006209 dephosphorylation reaction Methods 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- GZCWLCBFPRFLKL-UHFFFAOYSA-N 1-prop-2-ynoxypropan-2-ol Chemical compound CC(O)COCC#C GZCWLCBFPRFLKL-UHFFFAOYSA-N 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 102000013563 Acid Phosphatase Human genes 0.000 abstract 1
- 108010051457 Acid Phosphatase Proteins 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- 235000007164 Oryza sativa Nutrition 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 230000007071 enzymatic hydrolysis Effects 0.000 abstract 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000012634 fragment Substances 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 abstract 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 235000009566 rice Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 229940070710 valerate Drugs 0.000 abstract 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1461663 Preparing 17-esters of 17α,21-dihydroxy steroids LARK SpA 12 Nov 1974 [4 Jan 1974 (2)] 27543/74 Heading C2U A 17 - monoester of a 17α,21 - dihydroxy steroid is prepared by esterifying the corresponding 17α,21-dihydroxy steroid 21-phosphate with a carboxylic acid, a carboxylic acid anhydride or a carboxylic acid chloride under mild conditions, then dephosphorylating the intermediate 17-acyloxy-21-phosphate by enzymatic hydrolysis using an acid phosphatase at a controlled pH. The acylating agent preferably contains up to 11 C atoms and may be mixed with a diluent. An aqueous suspension, dispersion or solution of cells or tissues or their fragments or constituents, particularly of rice bran, is preferably used for the dephosphorylation carried out in an acidic medium, particularly pH 4-5, and at 10-50 C. The enzymatic dephosphorylation may be carried out on the esterification reaction mixture without isolating the 17 - acyloxy - 21 - phosphate. The 17- monoesters obtained may be further esterified to 17,21-diacyl-esters with the acyl residues being the same or different. Forty-one compounds falling within the formula are novel, where R 1 is H, F, Cl, CH 3 or CF 3 ; R 2 is H, OH, CH 3 , methylene or halomethylene; R 3 is H, CF, F, OH, or keto; R 4 is H, F, Cl, Br, CH 3 or methylene; X is H, F, or Cl and R ester groups include formate, acetate, propionate, butyrate, isobutyrate, valerate, isovalerate, caproate, caprylate, palargonate, aenanthate, and benzoate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19058/74A IT1044791B (en) | 1974-01-04 | 1974-01-04 | METHOD FOR THE PREPARATION OF 17 ACIL ESTERS OF 17 ALPHA 21 OF HYDROXY STEROIDS OF THE PREGNANO SERIES |
| IT1905974A IT1064067B (en) | 1974-01-04 | 1974-01-04 | 17 Alpha, 21-dihydroxy-steroid 17-monoesters prepn. - by 17-esterifying 21-phosphates and enzymatically dephosphorylating |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1461663A true GB1461663A (en) | 1977-01-19 |
Family
ID=26327038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2754374A Expired GB1461663A (en) | 1974-01-04 | 1974-11-12 | Process for the preparation of 17-esters of 17alpha,21-dihydroxy steroids of the pregnane series and products obtained |
Country Status (12)
| Country | Link |
|---|---|
| JP (2) | JPS5096558A (en) |
| AU (1) | AU7050774A (en) |
| CA (1) | CA1034521A (en) |
| CH (1) | CH606096A5 (en) |
| DE (2) | DE2431377A1 (en) |
| DK (2) | DK132661C (en) |
| FI (1) | FI189274A7 (en) |
| FR (2) | FR2256926B1 (en) |
| GB (1) | GB1461663A (en) |
| IL (1) | IL45142A0 (en) |
| NL (2) | NL7408524A (en) |
| SE (1) | SE408898B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610414A (en) * | 2013-11-05 | 2015-05-13 | 河南利华制药有限公司 | Prednisolone sodium phosphate production technology |
| CN109988212A (en) * | 2019-04-22 | 2019-07-09 | 河南利华制药有限公司 | A kind of Inflamase production method |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154748A (en) * | 1978-01-20 | 1979-05-15 | The Upjohn Company | Phosphate catalyzed acylation of steroidal tertiary alcohols |
| IT202000006442A1 (en) * | 2020-03-27 | 2021-09-27 | Genetic S P A | BUDESONIDE 21-PHOSPHATE SALTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS421686Y1 (en) * | 1964-05-02 | 1967-02-02 | ||
| JPS4617693Y1 (en) * | 1966-09-23 | 1971-06-21 |
-
1974
- 1974-06-20 FI FI1892/74A patent/FI189274A7/fi unknown
- 1974-06-24 SE SE7407989A patent/SE408898B/en unknown
- 1974-06-25 NL NL7408524A patent/NL7408524A/en unknown
- 1974-06-26 AU AU70507/74A patent/AU7050774A/en not_active Expired
- 1974-06-26 DK DK342774A patent/DK132661C/en not_active IP Right Cessation
- 1974-06-28 IL IL45142A patent/IL45142A0/en unknown
- 1974-06-28 CA CA203,680A patent/CA1034521A/en not_active Expired
- 1974-06-28 JP JP49073462A patent/JPS5096558A/ja active Pending
- 1974-06-29 DE DE2431377A patent/DE2431377A1/en active Pending
- 1974-11-12 GB GB2754374A patent/GB1461663A/en not_active Expired
- 1974-12-16 CH CH1167474A patent/CH606096A5/xx not_active IP Right Cessation
- 1974-12-20 NL NL7416691A patent/NL7416691A/en unknown
- 1974-12-26 FR FR7442886A patent/FR2256926B1/fr not_active Expired
- 1974-12-27 JP JP49149059A patent/JPS5096559A/ja active Pending
- 1974-12-27 DE DE19742461512 patent/DE2461512A1/en active Pending
- 1974-12-27 FR FR7443060A patent/FR2256763A1/fr not_active Withdrawn
- 1974-12-30 DK DK689774A patent/DK689774A/da unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610414A (en) * | 2013-11-05 | 2015-05-13 | 河南利华制药有限公司 | Prednisolone sodium phosphate production technology |
| CN104610414B (en) * | 2013-11-05 | 2016-08-31 | 河南利华制药有限公司 | A kind of production technology of Inflamase |
| CN109988212A (en) * | 2019-04-22 | 2019-07-09 | 河南利华制药有限公司 | A kind of Inflamase production method |
| CN109988212B (en) * | 2019-04-22 | 2020-11-20 | 河南利华制药有限公司 | Prednisolone sodium phosphate production method |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7416691A (en) | 1975-07-08 |
| JPS5096558A (en) | 1975-07-31 |
| FI189274A7 (en) | 1975-07-05 |
| JPS5096559A (en) | 1975-07-31 |
| FR2256926B1 (en) | 1977-07-08 |
| SE408898B (en) | 1979-07-16 |
| SE7408296L (en) | 1975-07-07 |
| DE2461512A1 (en) | 1975-07-24 |
| FR2256926A1 (en) | 1975-08-01 |
| DK689774A (en) | 1975-09-01 |
| DE2431377A1 (en) | 1975-07-17 |
| CA1034521A (en) | 1978-07-11 |
| DK342774A (en) | 1975-09-01 |
| DK132661C (en) | 1976-06-28 |
| DK132661B (en) | 1976-01-19 |
| FR2256763A1 (en) | 1975-08-01 |
| CH606096A5 (en) | 1978-10-13 |
| NL7408524A (en) | 1975-07-08 |
| AU7050774A (en) | 1976-01-08 |
| IL45142A0 (en) | 1974-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |