DE1129481B - Verfahren zur Herstellung von 17ª-Oxy-6ª-methyl-16-methylenpregn-4-en-3, 20-dion bzw. von dessen Acylderivaten - Google Patents
Verfahren zur Herstellung von 17ª-Oxy-6ª-methyl-16-methylenpregn-4-en-3, 20-dion bzw. von dessen AcylderivatenInfo
- Publication number
- DE1129481B DE1129481B DEB54167A DEB0054167A DE1129481B DE 1129481 B DE1129481 B DE 1129481B DE B54167 A DEB54167 A DE B54167A DE B0054167 A DEB0054167 A DE B0054167A DE 1129481 B DE1129481 B DE 1129481B
- Authority
- DE
- Germany
- Prior art keywords
- dione
- oxy
- methyl
- methylenepregn
- ene
- 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
- 125000002252 acyl group Chemical group 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 239000007868 Raney catalyst Substances 0.000 claims description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- -1 hydrogen halides Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XHDOQPPIHXTHNM-HQZKGGBDSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-16-methylidene-2,6,7,8,9,11,12,14,15,17-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@H](C(=O)C)[C@@]1(C)CC2 XHDOQPPIHXTHNM-HQZKGGBDSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BKWJSCFKITXBBM-NTNOATJHSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-6-methylidene-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1C(=C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 BKWJSCFKITXBBM-NTNOATJHSA-N 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 101100521345 Mus musculus Prop1 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108700017836 Prophet of Pit-1 Proteins 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960000445 ethisterone Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24077/58A GB858033A (en) | 1958-07-25 | 1958-07-25 | Improvements in or relating to 16-substituted-6-methyl steroid compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1129481B true DE1129481B (de) | 1962-05-17 |
Family
ID=10206005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB54167A Pending DE1129481B (de) | 1958-07-25 | 1959-07-24 | Verfahren zur Herstellung von 17ª-Oxy-6ª-methyl-16-methylenpregn-4-en-3, 20-dion bzw. von dessen Acylderivaten |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3296256A (en, 2012) |
| BE (1) | BE581054A (en, 2012) |
| CH (1) | CH375348A (en, 2012) |
| DE (1) | DE1129481B (en, 2012) |
| FR (1) | FR569M (en, 2012) |
| GB (1) | GB858033A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114075259B (zh) * | 2020-08-14 | 2024-04-12 | 保定九孚生化有限公司 | 一种醋酸可的松母液的回收方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787623A (en) * | 1954-09-30 | 1957-04-02 | William H Gebert | Reduction of 16-iodopregnane compounds |
| US2878247A (en) * | 1957-09-27 | 1959-03-17 | Searle & Co | Preparation of 6-methyl steroids of the pregnane series |
| US2871246A (en) * | 1958-05-28 | 1959-01-27 | Searle & Co | Process for 3-hydroxy-6-alkyl-5,16-pregnadien-20-ones and esters thereof |
-
1958
- 1958-07-25 GB GB24077/58A patent/GB858033A/en not_active Expired
-
1959
- 1959-07-24 DE DEB54167A patent/DE1129481B/de active Pending
- 1959-07-24 US US829234A patent/US3296256A/en not_active Expired - Lifetime
- 1959-07-25 BE BE581054A patent/BE581054A/fr unknown
- 1959-07-25 CH CH7623459A patent/CH375348A/de unknown
-
1960
- 1960-08-31 FR FR837317A patent/FR569M/fr active Active
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB858033A (en) | 1961-01-04 |
| BE581054A (fr) | 1959-11-16 |
| FR569M (en, 2012) | 1961-06-05 |
| CH375348A (de) | 1964-02-29 |
| US3296256A (en) | 1967-01-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2013032C3 (de) | 3-Amino-cardenolide, Verfahren zu ihrer Herstellung sowie deren Verwendung bei der Bekämpfung von Herz- und Kreislauf-Krankheiten | |
| DE1129481B (de) | Verfahren zur Herstellung von 17ª-Oxy-6ª-methyl-16-methylenpregn-4-en-3, 20-dion bzw. von dessen Acylderivaten | |
| DE1120447B (de) | Verfahren zur Herstellung von 17ª-Oxy-16-methylenpregn-4-en-3, 20-dion bzw. von dessen Acylderivaten | |
| DE1131665B (de) | Verfahren zur Herstellung von Aminosteroidverbindungen | |
| DE1793633C3 (de) | Verfahren zur Herstellung von Gona 4(5),9(10)dien3 onen Ausscheidung aus 1468642 | |
| DE1618871C3 (de) | Verfahren zur Herstellung eines Steroidketonderivates. Ausscheidung aus: 1468988 | |
| DE1966921C3 (de) | 17 alpha-propadienylsubstituierte 3-Ketosteroide und Verfahren zu deren Herstellung | |
| AT233177B (de) | Verfahren zur Herstellung des neuen 6α-Methyl-17 α-hydroxyprogesterons und seiner Ester | |
| DE1593058C3 (de) | Salpha, 16alpha-Dimethyl-4-pregnen-3beta-ol-20-on, Verfahren zu dessen Herstellung sowie dieses enthaltende pharmazeutische Zubereitung | |
| DE1001985C2 (de) | Verfahren zur Herstellung von in 8- und 9 (11)-Stellung ungesaettigten 7-Ketosteroiden der Ergostan- und Cholansaeurereihe | |
| DE1907804C3 (de) | 4-Chlor-1alpha,2alpha;6alpha,7alphadimethylen-3-keto-4-pregnene, Verfahren zu deren Herstellung sowie diese enthaltendes Mittel | |
| AT233180B (de) | Verfahren zur Herstellung von 17α-Hydroxy-16-methylenpregn-4-en-3, 20-dion und dessen Acylierungsprodukten | |
| DE1618662C3 (de) | 6-substituierte 16alpha-Methyl-4-pregnen- bzw. 4,6-pregnadien-3betaol-20-on-Verbindungen, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE1668688C3 (de) | 16alpha, 17-Alkylidendioxy-18methyl-19-nor-progesterone, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel | |
| DE1134987B (de) | Verfahren zur Herstellung von 17ª‡-Acyloxy-6-methyl-16-methylen-pregna-4, 6-dien-3, 20-dionen | |
| DE1252679B (de) | Verfahren zur Herstellung von zlM.5(10)-A-Homo-östratrien-3-on-derivaten | |
| DE1297604B (de) | Verfahren zur Herstellung delta 4, 16-Pregnadien-20-ol-3-on | |
| DE2256912A1 (de) | Digoxigenin-3- eckige klammer auf 2',3'-didesoxy-glykoside eckige klammer zu und verfahren zu ihrer herstellung | |
| DE1161265B (de) | Verfahren zur Herstellung von 3-Oxo-í¸-steroiden | |
| DE1041042B (de) | Verfahren zur Herstellung von in 4-Stellung substituierten Steroiden | |
| DE1966921B2 (de) | 17 alpha-propadienylsubstituierte 3-ketosteroide und verfahren zu deren herstellung | |
| DE1241825B (de) | Ver fahren zur Herstellung von 6 Chlor 4 6diLirverbindungen der Pregnan-, Androstan oder Cholestanreihe | |
| DE1177147B (de) | Verfahren zur Herstellung von 3-Enolaethern von 6-Formyl-3-oxo-?-steroiden | |
| DE1668685B2 (de) | 17-Hydroxy-und 17-Acyloxy-6beta, 7 beta-epoxy-1 alpha, 2 alpha-methylen-4-pregnen-3,20-dione, Verfahren zu deren Herstellung sowie diese enthaltende Mittel | |
| DE2161767A1 (de) | Verfahren zur Herstellung von Steroidverbindungen |