IL38339A - 5,10-epoxy-19-nor steroids and process for their preparation - Google Patents
5,10-epoxy-19-nor steroids and process for their preparationInfo
- Publication number
- IL38339A IL38339A IL38339A IL3833968A IL38339A IL 38339 A IL38339 A IL 38339A IL 38339 A IL38339 A IL 38339A IL 3833968 A IL3833968 A IL 3833968A IL 38339 A IL38339 A IL 38339A
- Authority
- IL
- Israel
- Prior art keywords
- group
- carbon
- steroids
- chosen
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000003431 steroids Chemical class 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- -1 keto acetyl Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
-
- 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 |
|---|---|---|---|
| FR99496 | 1967-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL38339A true IL38339A (en) | 1973-04-30 |
Family
ID=8627214
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL29578A IL29578A (en) | 1967-03-20 | 1968-03-05 | Process for the introduction of hydrocarbon substituents at the 10-position of 19-nor steroid derivatives and novel compounds thus obtained |
| IL38339A IL38339A (en) | 1967-03-20 | 1968-03-05 | 5,10-epoxy-19-nor steroids and process for their preparation |
| IL38339A IL38339A0 (en) | 1967-03-20 | 1971-12-13 | Process for the introduction of hydrocarbon substituents at the 10-position of 19-nor steroid derivatives and novel compounds thus obtained |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL29578A IL29578A (en) | 1967-03-20 | 1968-03-05 | Process for the introduction of hydrocarbon substituents at the 10-position of 19-nor steroid derivatives and novel compounds thus obtained |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38339A IL38339A0 (en) | 1967-03-20 | 1971-12-13 | Process for the introduction of hydrocarbon substituents at the 10-position of 19-nor steroid derivatives and novel compounds thus obtained |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5021470B1 (cs) |
| CH (1) | CH492690A (cs) |
| DE (1) | DE1668652B2 (cs) |
| DK (1) | DK129197B (cs) |
| FR (1) | FR1550974A (cs) |
| GB (2) | GB1228211A (cs) |
| IL (3) | IL29578A (cs) |
| NL (1) | NL158505B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2213272B1 (cs) * | 1973-01-05 | 1977-07-22 | Roussel Uclaf | |
| DE3630030A1 (de) * | 1986-09-01 | 1988-03-03 | Schering Ag | 13(alpha)-alkylgonan-(delta)(pfeil hoch)9(pfeil hoch)(pfeil hoch)((pfeil hoch)(pfeil hoch)1(pfeil hoch)1(pfeil hoch))(pfeil hoch)-5,10-epoxide |
| FR2854402B1 (fr) | 2003-04-29 | 2008-07-04 | Aventis Pharma Sa | Nouveau procede et intermediaires de preparation de composes 19-nor-steroides |
-
1967
- 1967-03-20 FR FR99496A patent/FR1550974A/fr not_active Expired
-
1968
- 1968-03-05 IL IL29578A patent/IL29578A/en unknown
- 1968-03-05 IL IL38339A patent/IL38339A/en unknown
- 1968-03-15 CH CH386068A patent/CH492690A/fr not_active IP Right Cessation
- 1968-03-19 GB GB1228211D patent/GB1228211A/en not_active Expired
- 1968-03-19 JP JP43017561A patent/JPS5021470B1/ja active Pending
- 1968-03-19 DK DK115568AA patent/DK129197B/da not_active IP Right Cessation
- 1968-03-19 GB GB1228212D patent/GB1228212A/en not_active Expired
- 1968-03-19 DE DE1968R0048274 patent/DE1668652B2/de active Granted
- 1968-03-19 NL NL6803859.A patent/NL158505B/xx not_active IP Right Cessation
-
1971
- 1971-12-13 IL IL38339A patent/IL38339A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL158505B (nl) | 1978-11-15 |
| IL38339A0 (en) | 1972-02-29 |
| DK129197B (da) | 1974-09-09 |
| IL29578A (en) | 1973-04-30 |
| DK129197C (cs) | 1975-03-24 |
| DE1668652A1 (de) | 1971-06-03 |
| FR1550974A (cs) | 1968-12-27 |
| NL6803859A (cs) | 1968-09-23 |
| JPS5021470B1 (cs) | 1975-07-23 |
| GB1228211A (cs) | 1971-04-15 |
| DE1668652B2 (de) | 1976-07-01 |
| GB1228212A (cs) | 1971-04-15 |
| CH492690A (fr) | 1970-06-30 |
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