CH433265A - Procédé de préparation de 1,5-dioxo-4-(2'-carboxy- ou carbalcoxy-éthyl)-7aB-méthyl-5,6,7,7a-tétrahydroindanes - Google Patents
Procédé de préparation de 1,5-dioxo-4-(2'-carboxy- ou carbalcoxy-éthyl)-7aB-méthyl-5,6,7,7a-tétrahydroindanesInfo
- Publication number
- CH433265A CH433265A CH275063A CH275063A CH433265A CH 433265 A CH433265 A CH 433265A CH 275063 A CH275063 A CH 275063A CH 275063 A CH275063 A CH 275063A CH 433265 A CH433265 A CH 433265A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- dioxo
- acid
- carboxy
- indane
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- HXZILEQYFQYQCE-UHFFFAOYSA-N 2-methylcyclopentane-1,3-dione Chemical compound CC1C(=O)CCC1=O HXZILEQYFQYQCE-UHFFFAOYSA-N 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- ISDUIDRCFYENQN-UHFFFAOYSA-N 5-oxohept-6-enoic acid Chemical compound OC(=O)CCCC(=O)C=C ISDUIDRCFYENQN-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 5
- MQIGRVMBIPYVRE-UHFFFAOYSA-N 3-(7a-methyl-1,5-dioxo-2,3,6,7-tetrahydroinden-4-yl)propanoic acid Chemical compound C1CC(=O)C(CCC(O)=O)=C2CCC(=O)C21C MQIGRVMBIPYVRE-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229960002179 ephedrine Drugs 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- YNQKVBKTYUFFPJ-UHFFFAOYSA-N methyl 3-(7a-methyl-1,5-dioxo-2,3,6,7-tetrahydroinden-4-yl)propanoate Chemical compound COC(=O)CCC1=C2CCC(=O)C2(C)CCC1=O YNQKVBKTYUFFPJ-UHFFFAOYSA-N 0.000 description 2
- ONGNQDROOOWKJT-UHFFFAOYSA-N methyl 5-oxohept-6-enoate Chemical compound COC(=O)CCCC(=O)C=C ONGNQDROOOWKJT-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- AOIYTIDHFMNVOO-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indene Chemical compound C1CCC=C2CCCC21 AOIYTIDHFMNVOO-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- KMPWYEUPVWOPIM-QAMTZSDWSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-QAMTZSDWSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- -1 ethyl ether-isopropyl ether Chemical compound 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N methyl propyl carbinol Natural products CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MZKUGCOENXBMFR-UHFFFAOYSA-N pyridin-1-ium;phosphate Chemical compound [O-]P([O-])([O-])=O.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 MZKUGCOENXBMFR-UHFFFAOYSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/215—Saturated compounds having only one carboxyl group and containing keto groups containing singly bound oxygen containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
- C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/38—Unsaturated compounds containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- 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
- C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR890184A FR1364556A (fr) | 1962-03-06 | 1962-03-06 | Nouveau procédé de synthèse de stéroïdes et de composés apparentés et produits utilisés dans ce procédé |
| FR957460A FR1476509A (fr) | 1962-03-06 | 1963-12-17 | Nouveau procédé de syntbèse de stéroïdes et de composés apparentés et produits utilisés dans ce procédé |
| FR960254A FR1512318A (fr) | 1962-03-06 | 1964-01-14 | Dérivés optiquement actifs de la 19-nor testostérone et procédé de préparation |
| FR964517A FR91612E (fr) | 1962-03-06 | 1964-02-20 | Dérivés optiquement actifs de la 19-nor testostérone et procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH433265A true CH433265A (fr) | 1967-04-15 |
Family
ID=27445406
Family Applications (10)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH275063A CH433265A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation de 1,5-dioxo-4-(2'-carboxy- ou carbalcoxy-éthyl)-7aB-méthyl-5,6,7,7a-tétrahydroindanes |
| CH275163A CH410934A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation d'un nouveau composé intermédiaire pour la synthèse de stéroïdes |
| CH384566A CH450406A (fr) | 1962-03-06 | 1963-03-05 | Procédé de synthèse d'un séco-stéroïde |
| CH275363A CH411858A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation de nouveaux composés intermédiaires pour la synthèse des stéroïdes |
| CH275263A CH424768A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation de nouveaux composés intermédiaires pour la synthèse de stéroïdes et des composés apparentés |
| CH275463A CH427782A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation d'un composé stéroïde |
| CH1630364A CH436274A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
| CH1630264A CH436273A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
| CH1630564A CH437272A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
| CH1630464A CH436275A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
Family Applications After (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH275163A CH410934A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation d'un nouveau composé intermédiaire pour la synthèse de stéroïdes |
| CH384566A CH450406A (fr) | 1962-03-06 | 1963-03-05 | Procédé de synthèse d'un séco-stéroïde |
| CH275363A CH411858A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation de nouveaux composés intermédiaires pour la synthèse des stéroïdes |
| CH275263A CH424768A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation de nouveaux composés intermédiaires pour la synthèse de stéroïdes et des composés apparentés |
| CH275463A CH427782A (fr) | 1962-03-06 | 1963-03-05 | Procédé de préparation d'un composé stéroïde |
| CH1630364A CH436274A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
| CH1630264A CH436273A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
| CH1630564A CH437272A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
| CH1630464A CH436275A (fr) | 1962-03-06 | 1964-12-17 | Procédé de préparation de 13-alcoyl-stéroïdes |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3413314A (enExample) |
| BE (4) | BE657263A (enExample) |
| BR (5) | BR6347416D0 (enExample) |
| CH (10) | CH433265A (enExample) |
| DE (7) | DE1468529C3 (enExample) |
| DK (7) | DK114131B (enExample) |
| FR (3) | FR1476509A (enExample) |
| GB (11) | GB1042632A (enExample) |
| IL (6) | IL22638A (enExample) |
| NL (8) | NL6414756A (enExample) |
| SE (5) | SE310364B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1526961A (fr) * | 1967-01-06 | 1968-05-31 | Roussel Uclaf | Nouveaux 4-oxa stéroïdes et procédé de préparation |
| US3979458A (en) * | 1967-12-04 | 1976-09-07 | Syntex Corporation | Production of unsaturated carbocyclic ketones |
| US3855247A (en) * | 1967-12-04 | 1974-12-17 | Syntex Corp | Production of unsaturated carbocyclic ketones |
| US3541210A (en) * | 1968-04-10 | 1970-11-17 | Sandoz Ag | 17-alpha-(2-butyn-1-yl)-substituted steroids |
| US3929876A (en) * | 1968-10-04 | 1975-12-30 | Hoffmann La Roche | Stereospecific total steroidal synthesis via substituted C/D-trans indanones |
| US3927031A (en) * | 1968-10-04 | 1975-12-16 | Hoffmann La Roche | Stereospecific total steroidal synthesis via substituted C/D-trans indanones |
| US3897460A (en) * | 1968-10-04 | 1975-07-29 | Hoffmann La Roche | 3{62 -Tertiarybutoxy-decahydro-benz{8 E{9 indenes |
| FR2183555B1 (enExample) * | 1972-05-10 | 1975-06-20 | Roussel Uclaf | |
| US4234491A (en) | 1978-06-19 | 1980-11-18 | Syntex (U.S.A.) Inc. | Steroid synthesis process using mixed anhydride |
| US4158012A (en) * | 1978-06-19 | 1979-06-12 | Syntex (U.S.A.) Inc. | Steroid synthesis process using mixed anhydride |
| US4400524A (en) * | 1981-07-28 | 1983-08-23 | The Upjohn Company | Grignard reagents prepared from 5-halopentan-2-one propylene ketals |
| US4900837A (en) * | 1982-05-18 | 1990-02-13 | University Of Florida | Brain-specific drug delivery of steroid sex hormones cleaved from pyridinium carboxylates and dihydro-pyridine carboxylate precursors |
| US5567830A (en) * | 1994-02-14 | 1996-10-22 | Cocensys, Inc. | Process for synthesis of acetylenic carbinols |
| DE19503327A1 (de) * | 1995-02-02 | 1996-08-08 | Basf Ag | Verfahren zur Herstellung von 5-Oxo-6-heptensäurealkylestern sowie neue Zwischenprodukte zu ihrer Herstellung |
| IL119649A (en) * | 1995-11-30 | 2002-03-10 | Akzo Nobel Nv | Preparation of Cyclic Kills of History - 3 keto- (5) 10, (-9) 11 steroidadians |
| ITUB20155260A1 (it) | 2015-10-30 | 2017-04-30 | Ind Chimica Srl | PROCESSO PER LA PREPARAZIONE DI 17?-idrossi-des-A-androst-9,10-en-5-one |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE632347A (enExample) * | ||||
| US2839537A (en) * | 1952-05-12 | 1958-06-17 | Ciba Pharm Prod Inc | Tricyclic diketone and process of manufacture |
| US3019252A (en) * | 1959-06-18 | 1962-01-30 | Lab Francais Chimiotherapie | Process for the preparation of novel derivatives of cyclopentanonaphthalene and products obtained thereby |
| US3115507A (en) * | 1960-01-22 | 1963-12-24 | Roussel Uclaf | New analogs of 19-nor-testosterone, their esters and process of preparation |
| GB965577A (en) * | 1960-07-29 | 1964-07-29 | Roussel Uclaf | New steroid compounds and processes for their preparation |
| FR1283951A (fr) * | 1960-12-28 | 1962-02-09 | Chimiotherapie Lab Franc | Nouveau dérivé propylé du phénanthrène et procédé de préparation |
-
0
- BE BE657262D patent/BE657262A/xx unknown
- NL NL122142D patent/NL122142C/xx active
- BE BE657260D patent/BE657260A/xx unknown
- NL NL126395D patent/NL126395C/xx active
- BE BE657261D patent/BE657261A/xx unknown
- NL NL123143D patent/NL123143C/xx active
- NL NL122309D patent/NL122309C/xx active
- BE BE657263D patent/BE657263A/xx unknown
-
1963
- 1963-03-05 DE DE1468529A patent/DE1468529C3/de not_active Expired
- 1963-03-05 DE DE1518111A patent/DE1518111C3/de not_active Expired
- 1963-03-05 SE SE2412/63A patent/SE310364B/xx unknown
- 1963-03-05 CH CH275063A patent/CH433265A/fr unknown
- 1963-03-05 DE DE1963R0034608 patent/DE1468530A1/de active Granted
- 1963-03-05 CH CH275163A patent/CH410934A/fr unknown
- 1963-03-05 CH CH384566A patent/CH450406A/fr unknown
- 1963-03-05 CH CH275363A patent/CH411858A/fr unknown
- 1963-03-05 CH CH275263A patent/CH424768A/fr unknown
- 1963-03-05 DE DE1963R0034609 patent/DE1468531B1/de active Pending
- 1963-03-05 CH CH275463A patent/CH427782A/fr unknown
- 1963-03-06 BR BR147416/63A patent/BR6347416D0/pt unknown
- 1963-03-06 GB GB27081/65A patent/GB1042632A/en not_active Expired
- 1963-03-06 DK DK102863AA patent/DK114131B/da unknown
- 1963-03-06 DK DK102963AA patent/DK121224B/da unknown
- 1963-03-06 GB GB9030/63A patent/GB1042631A/en not_active Expired
- 1963-03-06 DK DK102663AA patent/DK114687B/da unknown
- 1963-03-06 DK DK103063AA patent/DK111956B/da unknown
- 1963-03-06 GB GB27082/65A patent/GB1042633A/en not_active Expired
- 1963-12-17 FR FR957460A patent/FR1476509A/fr not_active Expired
-
1964
- 1964-01-14 FR FR960254A patent/FR1512318A/fr not_active Expired
- 1964-02-20 FR FR964517A patent/FR91612E/fr not_active Expired
- 1964-04-22 US US361872A patent/US3413314A/en not_active Expired - Lifetime
- 1964-06-12 DK DK295764AA patent/DK112032B/da unknown
- 1964-10-12 SE SE1225764A patent/SE319174B/xx unknown
- 1964-12-16 BR BR165403/64A patent/BR6465403D0/pt unknown
- 1964-12-16 BR BR165401/64A patent/BR6465401D0/pt unknown
- 1964-12-16 BR BR165402/64A patent/BR6465402D0/pt unknown
- 1964-12-17 IL IL22638A patent/IL22638A/xx unknown
- 1964-12-17 SE SE15298/64A patent/SE309038B/xx unknown
- 1964-12-17 IL IL22635A patent/IL22635A/xx unknown
- 1964-12-17 SE SE15301/64D patent/SE313306B/xx unknown
- 1964-12-17 GB GB36333/67A patent/GB1096771A/en not_active Expired
- 1964-12-17 GB GB51478/64A patent/GB1096761A/en not_active Expired
- 1964-12-17 IL IL30736A patent/IL30736A/xx unknown
- 1964-12-17 CH CH1630364A patent/CH436274A/fr unknown
- 1964-12-17 DE DE19641468895 patent/DE1468895A1/de not_active Withdrawn
- 1964-12-17 GB GB36203/66A patent/GB1096768A/en not_active Expired
- 1964-12-17 GB GB51481/64A patent/GB1057117A/en not_active Expired
- 1964-12-17 IL IL22637A patent/IL22637A/xx unknown
- 1964-12-17 CH CH1630264A patent/CH436273A/fr unknown
- 1964-12-17 DK DK618764A patent/DK144794C/da not_active IP Right Cessation
- 1964-12-17 CH CH1630564A patent/CH437272A/fr unknown
- 1964-12-17 NL NL6414756A patent/NL6414756A/xx unknown
- 1964-12-17 NL NL6414755A patent/NL6414755A/xx unknown
- 1964-12-17 GB GB36204/66A patent/GB1096769A/en not_active Expired
- 1964-12-17 CH CH1630464A patent/CH436275A/fr unknown
- 1964-12-17 IL IL22636A patent/IL22636A/xx unknown
- 1964-12-17 IL IL30735A patent/IL30735A/en unknown
- 1964-12-17 GB GB36202/66A patent/GB1096767A/en not_active Expired
- 1964-12-17 DK DK618564AA patent/DK127062B/da unknown
- 1964-12-17 SE SE15299/64A patent/SE302301B/xx unknown
- 1964-12-17 DE DE1468897A patent/DE1468897C3/de not_active Expired
- 1964-12-17 GB GB51479/64A patent/GB1096762A/en not_active Expired
- 1964-12-17 DE DE19641468896 patent/DE1468896A1/de active Pending
- 1964-12-17 NL NL6414702A patent/NL6414702A/xx unknown
- 1964-12-17 NL NL6414764A patent/NL6414764A/xx unknown
- 1964-12-17 GB GB51480/64A patent/GB1096763A/en not_active Expired
-
1965
- 1965-12-16 BR BR165404/65A patent/BR6565404D0/pt unknown
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