DE1618808B1 - Verfahren zur Herstellung des 10,11-Lactons 5, der 3-Äthylen dioxy-11Beta, 17Alfa-dihydroxy-20-oxo-19-nor-Delta5-pregnen-10Beta-carbonsäure - Google Patents
Verfahren zur Herstellung des 10,11-Lactons 5, der 3-Äthylen dioxy-11Beta, 17Alfa-dihydroxy-20-oxo-19-nor-Delta5-pregnen-10Beta-carbonsäureInfo
- Publication number
- DE1618808B1 DE1618808B1 DE1964R0045222 DER0045222A DE1618808B1 DE 1618808 B1 DE1618808 B1 DE 1618808B1 DE 1964R0045222 DE1964R0045222 DE 1964R0045222 DE R0045222 A DER0045222 A DE R0045222A DE 1618808 B1 DE1618808 B1 DE 1618808B1
- Authority
- DE
- Germany
- Prior art keywords
- lactone
- carboxylic acid
- oxo
- dihydroxy
- pregnen
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000005977 Ethylene Substances 0.000 title 1
- CWDJTDJQVUXQEA-UHFFFAOYSA-N CC=[PH3] Chemical compound CC=[PH3] CWDJTDJQVUXQEA-UHFFFAOYSA-N 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SBNLPRGISFUZQE-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 SBNLPRGISFUZQE-VMXHOPILSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 description 2
- 235000019792 magnesium silicate Nutrition 0.000 description 2
- 239000000391 magnesium silicate Substances 0.000 description 2
- 239000012285 osmium tetroxide Substances 0.000 description 2
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- YROIHKKJDMNYRB-UHFFFAOYSA-N 2-acetyloxyethylphosphonic acid Chemical compound CC(=O)OCCP(O)(O)=O YROIHKKJDMNYRB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000006137 acetoxylation reaction Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- -1 keto steroids Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- LFMTUFVYMCDPGY-UHFFFAOYSA-N n,n-diethylethanamine oxide Chemical compound CC[N+]([O-])(CC)CC LFMTUFVYMCDPGY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
-
- 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
- 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
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR944033A FR1453221A (fr) | 1963-08-07 | 1963-08-07 | Nouveau procédé de préparation de dérivés stéroïdes |
| FR944032A FR1453220A (fr) | 1963-08-07 | 1963-08-07 | Lactones stéroïdes et procédé de préparation |
| FR960549A FR1468646A (fr) | 1963-08-07 | 1964-01-16 | Nouveau procédé de préparation de composés stéroïdes 10 alcoylés |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618808B1 true DE1618808B1 (de) | 1971-11-11 |
Family
ID=27247393
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641468880 Pending DE1468880B1 (de) | 1963-08-07 | 1964-08-04 | Verfahren zur Herstellung von 17,20-Dehydro-steroiden |
| DE1964R0045220 Pending DE1618806B1 (de) | 1963-08-07 | 1964-08-04 | Verfahren zur Herstellung von 3,20-Dioxo-17Alfa-hydroxy-19-nor-9Beta,10Alfa-Delta4-pregnen |
| DE1964R0045222 Withdrawn DE1618808B1 (de) | 1963-08-07 | 1964-08-04 | Verfahren zur Herstellung des 10,11-Lactons 5, der 3-Äthylen dioxy-11Beta, 17Alfa-dihydroxy-20-oxo-19-nor-Delta5-pregnen-10Beta-carbonsäure |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641468880 Pending DE1468880B1 (de) | 1963-08-07 | 1964-08-04 | Verfahren zur Herstellung von 17,20-Dehydro-steroiden |
| DE1964R0045220 Pending DE1618806B1 (de) | 1963-08-07 | 1964-08-04 | Verfahren zur Herstellung von 3,20-Dioxo-17Alfa-hydroxy-19-nor-9Beta,10Alfa-Delta4-pregnen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3383385A (enExample) |
| JP (2) | JPS4821104B1 (enExample) |
| CH (1) | CH453347A (enExample) |
| DE (3) | DE1468880B1 (enExample) |
| FR (3) | FR1453220A (enExample) |
| GB (2) | GB1073988A (enExample) |
| IL (2) | IL21864A (enExample) |
| NL (2) | NL6409130A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704130A1 (de) * | 1977-01-28 | 1978-08-10 | Schering Ag | Verfahren zur herstellung von 17 beta- hydroxy-20-alkoxy-pregnan-21-saeure-derivaten |
| FR2552766B1 (fr) * | 1983-10-04 | 1987-06-26 | Theramex | Nouveau procede de preparation de derives de la serie du 17 a-hydroxy 19-nor progesterone |
| JPH0772194B2 (ja) * | 1985-09-03 | 1995-08-02 | ラボラトア−ル、テラメツクス | １７α−ヒドロキシ−１９−ノルプロゲステロン誘導体の新規製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2781342A (en) * | 1952-05-17 | 1957-02-12 | Upjohn Co | Steroid enamines |
| US2752366A (en) * | 1952-11-06 | 1956-06-26 | Upjohn Co | Carbonyloxysteroids |
| US2793217A (en) * | 1953-06-27 | 1957-05-21 | Lab Francais Chimiotherapie | New derivatives of adrenosterone and a process of making same |
| US2990415A (en) * | 1955-03-29 | 1961-06-27 | American Cyanamid Co | 9-substituted delta4-androstenes |
| US2955075A (en) * | 1957-04-15 | 1960-10-04 | Olin Mathieson | Synthesis of steroids by cylindrocarpon radicicola |
| US3114757A (en) * | 1961-09-22 | 1963-12-17 | Upjohn Co | 6-fluoro-3, 11-diketo-delta4, 17(20)-pregnadien-21-oic acid esters |
-
0
- NL NL123298D patent/NL123298C/xx active
-
1963
- 1963-08-07 FR FR944032A patent/FR1453220A/fr not_active Expired
- 1963-08-07 FR FR944033A patent/FR1453221A/fr not_active Expired
-
1964
- 1964-01-16 FR FR960549A patent/FR1468646A/fr not_active Expired
- 1964-07-27 CH CH984264A patent/CH453347A/fr unknown
- 1964-07-30 US US386375A patent/US3383385A/en not_active Expired - Lifetime
- 1964-08-04 DE DE19641468880 patent/DE1468880B1/de active Pending
- 1964-08-04 DE DE1964R0045220 patent/DE1618806B1/de active Pending
- 1964-08-04 DE DE1964R0045222 patent/DE1618808B1/de not_active Withdrawn
- 1964-08-06 IL IL21864A patent/IL21864A/xx unknown
- 1964-08-06 IL IL32873A patent/IL32873A/xx unknown
- 1964-08-07 JP JP39044975A patent/JPS4821104B1/ja active Pending
- 1964-08-07 GB GB32261/64A patent/GB1073988A/en not_active Expired
- 1964-08-07 NL NL6409130A patent/NL6409130A/xx unknown
- 1964-08-07 GB GB54690/66A patent/GB1073989A/en not_active Expired
-
1973
- 1973-01-20 JP JP48008298A patent/JPS5034555B1/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1073988A (en) | 1967-06-28 |
| FR1453221A (fr) | 1966-06-03 |
| GB1073989A (en) | 1967-06-28 |
| JPS4821104B1 (enExample) | 1973-06-26 |
| NL123298C (enExample) | |
| JPS5034555B1 (enExample) | 1975-11-10 |
| US3383385A (en) | 1968-05-14 |
| FR1468646A (fr) | 1967-02-10 |
| NL6409130A (enExample) | 1965-02-08 |
| IL21864A (en) | 1970-01-29 |
| DE1468880B1 (de) | 1970-04-23 |
| DE1618806B1 (de) | 1971-11-18 |
| IL32873A (en) | 1970-11-30 |
| FR1453220A (fr) | 1966-06-03 |
| CH453347A (fr) | 1968-06-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |