IL49763A - 16beta-methyl-9,11-epoxy-17alpha-hydroxy-1,4-pregnadiene-3,20-dione and its preparation - Google Patents
16beta-methyl-9,11-epoxy-17alpha-hydroxy-1,4-pregnadiene-3,20-dione and its preparationInfo
- Publication number
- IL49763A IL49763A IL49763A IL4976370A IL49763A IL 49763 A IL49763 A IL 49763A IL 49763 A IL49763 A IL 49763A IL 4976370 A IL4976370 A IL 4976370A IL 49763 A IL49763 A IL 49763A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- dione
- pregnadiene
- hydroxy
- epoxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000007269 dehydrobromination reaction Methods 0.000 claims 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 2
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 abstract 4
- 229960002537 betamethasone Drugs 0.000 abstract 4
- 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
- 150000002148 esters Chemical class 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 229940074404 sodium succinate Drugs 0.000 abstract 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07J5/0061—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 substituted in position 16
- C07J5/0069—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 substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—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 substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Table Devices Or Equipment (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT5292369 | 1969-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL49763A true IL49763A (en) | 1977-08-31 |
Family
ID=20081704
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL49763A IL49763A (en) | 1969-12-13 | 1970-12-10 | 16beta-methyl-9,11-epoxy-17alpha-hydroxy-1,4-pregnadiene-3,20-dione and its preparation |
| IL35823A IL35823A (en) | 1969-12-13 | 1970-12-10 | Process for the preparation of 16beta-methyl-9alpha-fluoro-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione and its 21-acylates |
| IL49763A IL49763A0 (en) | 1969-12-13 | 1976-06-10 | Novel 9,11-epoxy-pregnadienes and their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL35823A IL35823A (en) | 1969-12-13 | 1970-12-10 | Process for the preparation of 16beta-methyl-9alpha-fluoro-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione and its 21-acylates |
| IL49763A IL49763A0 (en) | 1969-12-13 | 1976-06-10 | Novel 9,11-epoxy-pregnadienes and their preparation |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3792046A (en, 2012) |
| JP (3) | JPS508080B1 (en, 2012) |
| AT (1) | AT304774B (en, 2012) |
| BE (1) | BE760236A (en, 2012) |
| CA (1) | CA932321A (en, 2012) |
| CH (1) | CH551395A (en, 2012) |
| DE (1) | DE2059050A1 (en, 2012) |
| DK (1) | DK130991B (en, 2012) |
| ES (1) | ES386385A1 (en, 2012) |
| FR (1) | FR2081356B1 (en, 2012) |
| GB (1) | GB1328998A (en, 2012) |
| IL (3) | IL49763A (en, 2012) |
| NL (1) | NL166694C (en, 2012) |
| NO (1) | NO136049C (en, 2012) |
| ZA (1) | ZA708393B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58212359A (ja) * | 1982-05-25 | 1983-12-10 | マグネツト・モ−トル・ゲゼルシヤフト・フユア・マグネツトモ−トリツシエ・テクニ−ク・ミツト・ベシユレンクテル・ハフツンク | 回転電気機械 |
| JPS6261175U (en, 2012) * | 1985-10-02 | 1987-04-16 | ||
| JPS62135570U (en, 2012) * | 1986-02-19 | 1987-08-26 | ||
| CA2448039A1 (en) * | 2001-06-18 | 2002-12-27 | Pharmacia & Upjohn Company | Process to prepare 11.beta., 17.alpha.,21-trihydroxy-6.alpha.-methylpregna-1,4-diene-3,20-dione 21-acetate |
| US20040006240A1 (en) * | 2001-06-18 | 2004-01-08 | Pearlman Bruce Allen | Process to prepare 11beta,17alpha ,21-trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione 21-acetate |
| CN101555268B (zh) * | 2009-05-21 | 2011-11-30 | 广西万德药业股份有限公司 | 一种糖皮质激素类9，11环氧物中间体制备方法 |
| CN102304163A (zh) * | 2011-07-11 | 2012-01-04 | 浙江仙居仙乐药业有限公司 | 一种倍他米松上氟合成方法 |
| CN104945464B (zh) * | 2015-04-17 | 2016-10-26 | 浙江仙居仙乐药业有限公司 | 一种倍他米松环氧水解物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1274397A (fr) * | 1958-12-16 | 1961-10-27 | Chimiotherapie Lab Franc | Procédé de préparation de dérivés 9alpha-fluoro 16alpha-méthyl delta1, 4-pregnadiènes |
| FR1243528A (fr) * | 1959-08-05 | 1960-10-14 | Chimiotherapie Lab Franc | Procédé d'acétoxylation de stéroïdes en 21 par l'intermédiaire de dérivés diiodés |
-
1970
- 1970-12-01 DE DE19702059050 patent/DE2059050A1/de not_active Ceased
- 1970-12-01 GB GB5696170A patent/GB1328998A/en not_active Expired
- 1970-12-02 DK DK613670AA patent/DK130991B/da unknown
- 1970-12-08 NL NL7017904.A patent/NL166694C/xx not_active IP Right Cessation
- 1970-12-08 CA CA100128A patent/CA932321A/en not_active Expired
- 1970-12-10 IL IL49763A patent/IL49763A/en unknown
- 1970-12-10 CH CH1828270A patent/CH551395A/xx not_active IP Right Cessation
- 1970-12-10 IL IL35823A patent/IL35823A/en unknown
- 1970-12-11 NO NO4780/70A patent/NO136049C/no unknown
- 1970-12-11 FR FR7044641A patent/FR2081356B1/fr not_active Expired
- 1970-12-11 JP JP45109617A patent/JPS508080B1/ja active Pending
- 1970-12-11 BE BE760236A patent/BE760236A/xx unknown
- 1970-12-11 ZA ZA708393A patent/ZA708393B/xx unknown
- 1970-12-11 AT AT1119470A patent/AT304774B/de active
- 1970-12-12 ES ES386385A patent/ES386385A1/es not_active Expired
-
1972
- 1972-08-07 US US00278394A patent/US3792046A/en not_active Expired - Lifetime
-
1976
- 1976-06-10 IL IL49763A patent/IL49763A0/xx unknown
-
1978
- 1978-11-08 JP JP13683778A patent/JPS5721279B1/ja active Pending
- 1978-11-08 JP JP13683678A patent/JPS5721280B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL49763A0 (en) | 1976-08-31 |
| NL166694B (nl) | 1981-04-15 |
| JPS508080B1 (en, 2012) | 1975-04-01 |
| IL35823A0 (en) | 1971-02-25 |
| CH551395A (de) | 1974-07-15 |
| NO136049B (en, 2012) | 1977-04-04 |
| ES386385A1 (es) | 1973-03-16 |
| JPS5721279B1 (en, 2012) | 1982-05-06 |
| BE760236A (fr) | 1971-05-17 |
| US3792046A (en) | 1974-02-12 |
| CA932321A (en) | 1973-08-21 |
| NL7017904A (en, 2012) | 1971-06-15 |
| NO136049C (no) | 1977-07-13 |
| IL35823A (en) | 1977-08-31 |
| FR2081356B1 (en, 2012) | 1976-09-17 |
| DK130991C (en, 2012) | 1975-12-08 |
| DE2059050A1 (de) | 1972-04-06 |
| NL166694C (nl) | 1981-09-15 |
| GB1328998A (en) | 1973-09-05 |
| JPS5721280B1 (en, 2012) | 1982-05-06 |
| AT304774B (de) | 1973-01-25 |
| DK130991B (da) | 1975-05-12 |
| FR2081356A1 (en, 2012) | 1971-12-03 |
| ZA708393B (en) | 1972-07-26 |
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