CH504474A - Verfahren zur Herstellung von Oxa-Steroidverbindungen - Google Patents
Verfahren zur Herstellung von Oxa-SteroidverbindungenInfo
- Publication number
- CH504474A CH504474A CH1119066A CH1119066A CH504474A CH 504474 A CH504474 A CH 504474A CH 1119066 A CH1119066 A CH 1119066A CH 1119066 A CH1119066 A CH 1119066A CH 504474 A CH504474 A CH 504474A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxa
- dien
- oestra
- hydroxy
- bromine
- Prior art date
Links
- -1 lactone steroid dienes Chemical class 0.000 title claims description 19
- 150000005671 trienes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- BMJKUPRTBJFNIP-IFIJOSMWSA-N C[C@@]12C(CC[C@H]1[C@@H]1CCC3=CC(OCC3=C1CC2)=O)=O Chemical compound C[C@@]12C(CC[C@H]1[C@@H]1CCC3=CC(OCC3=C1CC2)=O)=O BMJKUPRTBJFNIP-IFIJOSMWSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 2
- UOOBRGOOHWDAMP-IFOZYUSPSA-N (3as,3br,9bs,11as)-11a-methyl-3,3a,3b,4,5,6,9,9b,10,11-decahydro-2h-indeno[4,5-h]isochromene-1,7-dione Chemical compound C1OC(=O)CC2=C1[C@H]1CC[C@](C)(C(CC3)=O)[C@@H]3[C@@H]1CC2 UOOBRGOOHWDAMP-IFOZYUSPSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000001195 anabolic effect Effects 0.000 abstract description 3
- 230000001548 androgenic effect Effects 0.000 abstract description 3
- 241000223892 Tetrahymena Species 0.000 abstract description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract description 2
- 125000003435 aroyl group Chemical group 0.000 abstract description 2
- 239000000583 progesterone congener Substances 0.000 abstract description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003263 anabolic agent Substances 0.000 abstract 1
- 229940124325 anabolic agent Drugs 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- MYTMXVHNEWBFAL-UHFFFAOYSA-L dipotassium;carbonate;hydrate Chemical compound O.[K+].[K+].[O-]C([O-])=O MYTMXVHNEWBFAL-UHFFFAOYSA-L 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- LYQOBIBYSUTPIQ-KMFMINBZSA-N (3aS,3bS,11aS)-11a-methyl-1,2,3,3a,3b,4,5,9,10,11-decahydroindeno[4,5-h]isochromen-7-one Chemical class C[C@@]12CCC[C@H]1[C@@H]1CCC3=CC(OCC3=C1CC2)=O LYQOBIBYSUTPIQ-KMFMINBZSA-N 0.000 description 1
- HXUKLEOOKNOIJM-UHFFFAOYSA-N 2-cyclopentylpropanoic acid Chemical compound OC(=O)C(C)C1CCCC1 HXUKLEOOKNOIJM-UHFFFAOYSA-N 0.000 description 1
- PFSLCDNYNJTYDO-UHFFFAOYSA-N 2-cyclopentylpropanoyl chloride Chemical compound ClC(=O)C(C)C1CCCC1 PFSLCDNYNJTYDO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- AQMHNCQZLQUNJI-UHFFFAOYSA-N [CH2]CCCCCC Chemical compound [CH2]CCCCCC AQMHNCQZLQUNJI-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47760065A | 1965-08-05 | 1965-08-05 | |
| US47931865A | 1965-08-12 | 1965-08-12 | |
| US565707A US3405140A (en) | 1965-08-05 | 1966-07-18 | 17-(lower aliphatic mono-unsaturated hydrocarbon)-17beta-hydroxy-2-oxaestra-4, 9(10)-dien-3-ones, 11-dehydro compounds corresponding and esters thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH504474A true CH504474A (de) | 1971-03-15 |
Family
ID=27413423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1119066A CH504474A (de) | 1965-08-05 | 1966-08-03 | Verfahren zur Herstellung von Oxa-Steroidverbindungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3405140A (OSRAM) |
| BE (1) | BE685100A (OSRAM) |
| BR (1) | BR6681897D0 (OSRAM) |
| CH (1) | CH504474A (OSRAM) |
| DK (2) | DK116514B (OSRAM) |
| ES (1) | ES341754A1 (OSRAM) |
| GB (1) | GB1145323A (OSRAM) |
| IL (1) | IL26268A (OSRAM) |
| SE (1) | SE336579B (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3246014A (en) * | 1964-02-27 | 1966-04-12 | Searle & Co | Optionally 6-methylated 17alpha-alkynyl-17beta-oxygenated-2-oxa-5alpha-androstan-3-ones, 19-nor compounds corresponding, and delta4 and delta5(10) derivatives thereof |
-
1966
- 1966-07-18 US US565707A patent/US3405140A/en not_active Expired - Lifetime
- 1966-08-03 CH CH1119066A patent/CH504474A/de not_active IP Right Cessation
- 1966-08-04 DK DK405266AA patent/DK116514B/da unknown
- 1966-08-04 BR BR181897/66A patent/BR6681897D0/pt unknown
- 1966-08-04 IL IL26268A patent/IL26268A/xx unknown
- 1966-08-04 BE BE685100D patent/BE685100A/xx unknown
- 1966-08-05 GB GB35244/66A patent/GB1145323A/en not_active Expired
- 1966-08-05 SE SE10626/66A patent/SE336579B/xx unknown
-
1967
- 1967-06-14 ES ES341754A patent/ES341754A1/es not_active Expired
- 1967-07-28 DK DK391367AA patent/DK124266B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6681897D0 (pt) | 1973-10-25 |
| DK116514B (da) | 1970-01-19 |
| US3405140A (en) | 1968-10-08 |
| ES341754A1 (es) | 1968-09-16 |
| IL26268A (en) | 1970-04-20 |
| DE1593407A1 (de) | 1970-07-30 |
| BE685100A (OSRAM) | 1967-02-06 |
| SE336579B (OSRAM) | 1971-07-12 |
| DK124266B (da) | 1972-10-02 |
| DE1593407B2 (de) | 1976-01-15 |
| GB1145323A (en) | 1969-03-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |