DE1249270B - Verfahien zur Herstellung von /114-16si-Methvlsteroiden - Google Patents
Verfahien zur Herstellung von /114-16si-MethvlsteroidenInfo
- Publication number
- DE1249270B DE1249270B DENDAT1249270D DE1249270DA DE1249270B DE 1249270 B DE1249270 B DE 1249270B DE NDAT1249270 D DENDAT1249270 D DE NDAT1249270D DE 1249270D A DE1249270D A DE 1249270DA DE 1249270 B DE1249270 B DE 1249270B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- dione
- diol
- fluoro
- chloro
- 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 19
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000005805 hydroxylation reaction Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 14
- 239000000155 melt Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Substances OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 229960001067 hydrocortisone acetate Drugs 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- BUTKIHRNYUEGKB-UHFFFAOYSA-N 3,3-dimethylbutanoyl chloride Chemical compound CC(C)(C)CC(Cl)=O BUTKIHRNYUEGKB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- WHZJZHDLXBPSQK-UHFFFAOYSA-N butanoyl butanoate pyridine Chemical compound N1=CC=CC=C1.C(CCC)(=O)OC(CCC)=O WHZJZHDLXBPSQK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
- -1 pregnatrien-21-ol-3,20-dione-butyrate Chemical compound 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC034140 | 1963-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1249270B true DE1249270B (de) | 1967-09-07 |
Family
ID=7433039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1249270D Pending DE1249270B (de) | 1963-11-09 | Verfahien zur Herstellung von /114-16si-Methvlsteroiden |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE655494A (enrdf_load_stackoverflow) |
| BR (1) | BR6464017D0 (enrdf_load_stackoverflow) |
| DE (1) | DE1249270B (enrdf_load_stackoverflow) |
| DK (1) | DK118556B (enrdf_load_stackoverflow) |
| FR (1) | FR4556M (enrdf_load_stackoverflow) |
| GB (1) | GB1068058A (enrdf_load_stackoverflow) |
| NL (1) | NL155266B (enrdf_load_stackoverflow) |
| NO (1) | NO125050B (enrdf_load_stackoverflow) |
| SE (1) | SE324765B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012011106A1 (en) * | 2010-07-20 | 2012-01-26 | Taro Pharmaceutical Industries Ltd. | Process for the preparation of 17-desoxy-corticosteroids |
-
0
- BE BE655494D patent/BE655494A/xx unknown
- DE DENDAT1249270D patent/DE1249270B/de active Pending
-
1964
- 1964-09-15 NO NO15475964A patent/NO125050B/no unknown
- 1964-10-13 GB GB41756/64A patent/GB1068058A/en not_active Expired
- 1964-10-27 DK DK529264A patent/DK118556B/da unknown
- 1964-11-02 NL NL646412708A patent/NL155266B/xx not_active IP Right Cessation
- 1964-11-06 BR BR16401764A patent/BR6464017D0/pt unknown
- 1964-11-09 SE SE1348664A patent/SE324765B/xx unknown
-
1965
- 1965-02-05 FR FR4502A patent/FR4556M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK118556B (da) | 1970-09-07 |
| NL6412708A (enrdf_load_stackoverflow) | 1965-05-10 |
| GB1068058A (en) | 1967-05-10 |
| FR4556M (enrdf_load_stackoverflow) | 1966-11-02 |
| BE655494A (enrdf_load_stackoverflow) | |
| NL155266B (nl) | 1977-12-15 |
| SE324765B (enrdf_load_stackoverflow) | 1970-06-15 |
| BR6464017D0 (pt) | 1973-07-26 |
| NO125050B (enrdf_load_stackoverflow) | 1972-07-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2035738A1 (de) | Neue Androstandenvate und Verfahren zu ihrer Herstellung | |
| DE1443683C3 (de) | 7alpha Methyl 17alpha athinyl östradiol und sein 3 Methylather, Ver fahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate | |
| DE1249270B (de) | Verfahien zur Herstellung von /114-16si-Methvlsteroiden | |
| DE1618871C3 (de) | Verfahren zur Herstellung eines Steroidketonderivates. Ausscheidung aus: 1468988 | |
| DE1793633C3 (de) | Verfahren zur Herstellung von Gona 4(5),9(10)dien3 onen Ausscheidung aus 1468642 | |
| DE1593516C3 (de) | 4-Halogen-1,2 alpha; 6,7 betabismethylen-delta hoch 4-3-ketosteroide, Verfahren zu ihrer Herstellung sowie diese Steroide enthaltende Mittel | |
| DE2109154A1 (de) | Neue Spiro- eckige Klammer auf steroid-17,2-furan-3-one eckige Klammer zu und ein Verfahren zu deren Herstellung | |
| DE1793046A1 (de) | 16alpha,17alpha-Methylensteroide der Pregnanreihe mit substituierter Methylengruppe | |
| AT233184B (de) | Verfahren zur Herstellung von 3-Oxo-Δ<1,4>-steroiden | |
| DE1568499C3 (de) | Verfahren zur Herstellung von ungesättigten Lactonen der Steroidreihe | |
| AT270884B (de) | Verfahren zur Herstellung von neuen 4,6-Pregnadienderivaten | |
| AT250578B (de) | Verfahren zur Herstellung von 3-Enoläthern | |
| AT253704B (de) | Verfahren zur Herstellung des neuen 7α-Methyl-16α-hydroxy-östrons und seines 3, 16-Diacetates | |
| AT267769B (de) | Verfahren zur Herstellung von neuen 9β,10α-Steroiden | |
| DE2217814A1 (de) | 16beta-Alkyl-17alpha,20,21 -trihydroxypregnene und Verfahren zu ihrer Herstellung | |
| AT266350B (de) | Verfahren zur Herstellung von neuen 9β,10α-Steroiden | |
| DE2018252A1 (de) | Neues Verfahren zur Herstellung von 18-Cyano-Pregnan-Verbindungen | |
| DE1907804C3 (de) | 4-Chlor-1alpha,2alpha;6alpha,7alphadimethylen-3-keto-4-pregnene, Verfahren zu deren Herstellung sowie diese enthaltendes Mittel | |
| DE2256866C3 (de) | Verfahren zur Herstellung von 17 alpha- oder 17beta-Hydroxy-Verbindungen der 20-Ketopregnan- oder -17alpha-pregnanreihe | |
| DE1237111B (de) | Verfahren zur Herstellung von 1, 2alpha-Methylen-19-nor-testosteronderivaten | |
| CH554851A (de) | Verfahren zur herstellung neuer (delta)1,4-9-chlor-11-hydroxy16(alpha)-methyl-steroide. | |
| DE1443638A1 (de) | Neue 7 alpha-Methyl-androstene und ein Verfahren zu deren Herstellung | |
| DE2003653B2 (de) | Verfahren zur Herstellung von Pregnan-20-on-3beta, 5beta, 14beta, 21-tetrol bzw. dessen 3,21-di-tetrahydropyranyläther sowie die entsprechenden Zwischenprodukte | |
| CH549001A (de) | Verfahren zur herstellung neuer halogensteroide. | |
| DD247682A1 (de) | Verfahren zur herstellung von 8 beta, 14 beta-epoxy-oestranen |