NO134214B - - Google Patents
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- Publication number
- NO134214B NO134214B NO6839A NO3968A NO134214B NO 134214 B NO134214 B NO 134214B NO 6839 A NO6839 A NO 6839A NO 3968 A NO3968 A NO 3968A NO 134214 B NO134214 B NO 134214B
- Authority
- NO
- Norway
- Prior art keywords
- diene
- oxa
- estra
- gona
- seco
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000007269 dehydrobromination reaction Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 5
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 5
- 239000000391 magnesium silicate Substances 0.000 description 5
- 229910052919 magnesium silicate Inorganic materials 0.000 description 5
- 235000019792 magnesium silicate Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- -1 3,5-dione steroid Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 230000000962 progestomimetic effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MXQNHNJSQKBNDC-UHFFFAOYSA-N 2-methoxy-2h-pyran Chemical class COC1OC=CC=C1 MXQNHNJSQKBNDC-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical class C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002914 oxasteroids Chemical class 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 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)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR90264A FR1526961A (fr) | 1967-01-06 | 1967-01-06 | Nouveaux 4-oxa stéroïdes et procédé de préparation |
| FR90265A FR1526962A (fr) | 1967-01-06 | 1967-01-06 | Nouveau procédé de préparation d'un composé gonatriénique et produits en résultant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134214B true NO134214B (en, 2012) | 1976-05-24 |
| NO134214C NO134214C (en, 2012) | 1976-09-01 |
Family
ID=26174488
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO6839A NO134214C (en, 2012) | 1967-01-06 | 1968-01-05 | |
| NO69154A NO134159C (en, 2012) | 1967-01-06 | 1969-01-15 | |
| NO69153A NO134213C (en, 2012) | 1967-01-06 | 1969-01-15 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO69154A NO134159C (en, 2012) | 1967-01-06 | 1969-01-15 | |
| NO69153A NO134213C (en, 2012) | 1967-01-06 | 1969-01-15 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3499913A (en, 2012) |
| AT (4) | AT281318B (en, 2012) |
| BE (1) | BE708997A (en, 2012) |
| CH (1) | CH483452A (en, 2012) |
| DE (1) | DE1668641C3 (en, 2012) |
| DK (3) | DK135630B (en, 2012) |
| ES (2) | ES348970A1 (en, 2012) |
| FR (2) | FR1526961A (en, 2012) |
| GB (3) | GB1206818A (en, 2012) |
| IL (3) | IL38446A (en, 2012) |
| NL (1) | NL6800211A (en, 2012) |
| NO (3) | NO134214C (en, 2012) |
| SE (1) | SE328882B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU201091B (en) | 1985-12-26 | 1990-09-28 | Mitsubishi Chem Ind | Process for producing gonatriene derivatives and pharmaceutical compositions comprising same |
| US5206415A (en) * | 1991-12-20 | 1993-04-27 | Washington University | Tricyclic steroid analogs |
| US5434274A (en) * | 1991-12-20 | 1995-07-18 | Washington University | Benz(epsilon)indene compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138617A (en) * | 1959-08-27 | 1964-06-23 | Roussel Uclaf | Processes for the production of 19-nor-delta4-[9beta], [10alpha]-androstenes and intermediates |
| FR1366725A (fr) * | 1961-01-31 | 1964-07-17 | Roussel Uclaf | Nouveaux oxa-stéroïdes, leur préparation et leur utilisation en synthèse stéroïdienne |
| US3085098A (en) * | 1960-07-29 | 1963-04-09 | Roussel Uclaf | Process for the preparation of 17beta-oxy-genated-delta4, 9(10)-estradiene-3-one |
| US3102145A (en) * | 1961-06-28 | 1963-08-27 | Roussel Uclaf | Intermediate in the preparation of 19-nor-progesterone |
| FR1305992A (fr) * | 1961-07-21 | 1962-10-13 | Roussel Uclaf | Procédé de préparation de certains 19-nor stéroïdes et produits utilisés dans ce procédé |
| NL126395C (en, 2012) * | 1962-03-06 | |||
| US3422121A (en) * | 1965-08-13 | 1969-01-14 | Merck & Co Inc | Process for the preparation of 13-lower alkyl-gona-4,8(14),9-triene-3,17-dione |
-
1967
- 1967-01-06 FR FR90264A patent/FR1526961A/fr not_active Expired
- 1967-01-06 FR FR90265A patent/FR1526962A/fr not_active Expired
- 1967-12-18 IL IL38446A patent/IL38446A/en unknown
- 1967-12-18 IL IL29150A patent/IL29150A/en unknown
- 1967-12-18 IL IL38246A patent/IL38246A/xx unknown
- 1967-12-22 CH CH1810067A patent/CH483452A/fr not_active IP Right Cessation
-
1968
- 1968-01-03 US US695364A patent/US3499913A/en not_active Expired - Lifetime
- 1968-01-05 NO NO6839A patent/NO134214C/no unknown
- 1968-01-05 SE SE00149/68A patent/SE328882B/xx unknown
- 1968-01-05 NL NL6800211A patent/NL6800211A/xx unknown
- 1968-01-05 AT AT1123868A patent/AT281318B/de not_active IP Right Cessation
- 1968-01-05 DE DE1668641A patent/DE1668641C3/de not_active Expired
- 1968-01-05 AT AT1123668A patent/AT287933B/de not_active IP Right Cessation
- 1968-01-05 ES ES348970A patent/ES348970A1/es not_active Expired
- 1968-01-05 DK DK3568AA patent/DK135630B/da not_active IP Right Cessation
- 1968-01-05 AT AT15168A patent/AT283610B/de not_active IP Right Cessation
- 1968-01-05 BE BE708997D patent/BE708997A/xx not_active IP Right Cessation
- 1968-01-05 ES ES348969A patent/ES348969A1/es not_active Expired
- 1968-01-05 AT AT1123768A patent/AT284353B/de not_active IP Right Cessation
- 1968-01-08 GB GB6774/70A patent/GB1206818A/en not_active Expired
- 1968-01-08 GB GB995/68A patent/GB1206816A/en not_active Expired
- 1968-01-08 GB GB6773/70A patent/GB1206817A/en not_active Expired
-
1969
- 1969-01-15 NO NO69154A patent/NO134159C/no unknown
- 1969-01-15 NO NO69153A patent/NO134213C/no unknown
-
1970
- 1970-12-14 DK DK632870AA patent/DK126936B/da not_active IP Right Cessation
- 1970-12-14 DK DK632970AA patent/DK130307B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO134213C (en, 2012) | 1976-09-01 |
| NO134159C (en, 2012) | 1976-08-25 |
| FR1526962A (fr) | 1968-05-31 |
| DE1793691B2 (de) | 1976-05-13 |
| BE708997A (en, 2012) | 1968-07-05 |
| DE1668641C3 (de) | 1975-03-20 |
| DE1668641A1 (de) | 1972-03-02 |
| NO134214C (en, 2012) | 1976-09-01 |
| NL6800211A (en, 2012) | 1968-07-08 |
| SE328882B (en, 2012) | 1970-09-28 |
| DK130307C (en, 2012) | 1975-06-30 |
| AT287933B (de) | 1971-02-10 |
| CH483452A (fr) | 1969-12-31 |
| GB1206818A (en) | 1970-09-30 |
| AT283610B (de) | 1970-08-10 |
| DE1793691A1 (de) | 1972-07-27 |
| NO134159B (en, 2012) | 1976-05-18 |
| ES348970A1 (es) | 1969-08-16 |
| ES348969A1 (es) | 1969-03-16 |
| IL38446A (en) | 1972-12-29 |
| AT284353B (de) | 1970-09-10 |
| DK126936B (da) | 1973-09-03 |
| AT281318B (de) | 1970-05-11 |
| DE1668641B2 (de) | 1974-08-08 |
| GB1206817A (en) | 1970-09-30 |
| US3499913A (en) | 1970-03-10 |
| IL38246A (en) | 1972-10-29 |
| NO134213B (en, 2012) | 1976-05-24 |
| FR1526961A (fr) | 1968-05-31 |
| GB1206816A (en) | 1970-09-30 |
| DK130307B (da) | 1975-02-03 |
| IL29150A (en) | 1972-09-28 |
| DK135630B (da) | 1977-05-31 |
| DK135630C (en, 2012) | 1977-10-31 |
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