DE2260303C2 - Verfahren zur Herstellung von Pregnansäurederivaten - Google Patents
Verfahren zur Herstellung von PregnansäurederivatenInfo
- Publication number
- DE2260303C2 DE2260303C2 DE2260303A DE2260303A DE2260303C2 DE 2260303 C2 DE2260303 C2 DE 2260303C2 DE 2260303 A DE2260303 A DE 2260303A DE 2260303 A DE2260303 A DE 2260303A DE 2260303 C2 DE2260303 C2 DE 2260303C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- methyl
- oxide
- pregnadiene
- reaction
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 15
- GWZUYOSMTQIJMY-DIKHCDEOSA-N 2-[(8s,9s,10s,13r,14s,17r)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]acetic acid Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CC(O)=O)[C@@H]4[C@@H]3CCC21 GWZUYOSMTQIJMY-DIKHCDEOSA-N 0.000 title claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 9
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- VFWRGKJLLYDFBY-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag].[Ag] VFWRGKJLLYDFBY-UHFFFAOYSA-N 0.000 claims description 3
- 150000002373 hemiacetals Chemical class 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- -1 alkyl radical Chemical group 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 6
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PUHAKHQMSBQAKT-UHFFFAOYSA-L copper;butanoate Chemical compound [Cu+2].CCCC([O-])=O.CCCC([O-])=O PUHAKHQMSBQAKT-UHFFFAOYSA-L 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography 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
- C07J5/0007—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 not substituted in position 17 alfa
- C07J5/0023—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 not substituted in position 17 alfa substituted in position 16
- C07J5/003—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 not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group including 16-alkylidene substitutes
- C07J5/0038—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 not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group including 16-alkylidene substitutes by an alkyl group
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (27)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2260303A DE2260303C2 (de) | 1972-12-06 | 1972-12-06 | Verfahren zur Herstellung von Pregnansäurederivaten |
DK631373A DK131864C (da) | 1972-12-06 | 1973-11-22 | Fremgangsmade til fremstilling af pregnan-21-syrederivater |
FI733621A FI52347C (fi) | 1972-12-06 | 1973-11-23 | Menetelmä 21-pregnaanihappojohdannaisten valmistamiseksi. |
YU3068/73A YU35451B (en) | 1972-12-06 | 1973-11-25 | Process for obtaining pregnanic acid derivatives |
SE7315979A SE399712B (sv) | 1972-12-06 | 1973-11-26 | Sett att framstella pregnansyraderivat |
DD174979A DD108529A5 (US08066781-20111129-C00013.png) | 1972-12-06 | 1973-11-29 | |
AU63113/73A AU6311373A (en) | 1972-12-06 | 1973-11-30 | Pregnane acids |
IL43745A IL43745A (en) | 1972-12-06 | 1973-12-03 | Process for the manufacture of 3,20-dioxo-pregn-4-en-21-oic acids |
RO7376884A RO71431A (ro) | 1972-12-06 | 1973-12-04 | Procedeu de preparare a derivatilor acidului pregnanic |
PL1973167042A PL89573B1 (US08066781-20111129-C00013.png) | 1972-12-06 | 1973-12-04 | |
IE2192/73A IE38608B1 (en) | 1972-12-06 | 1973-12-04 | Process for the manufacture of pregnane acids |
SU1976253A SU524523A3 (ru) | 1972-12-06 | 1973-12-04 | Способ получени производных прегнановой кислоты |
NO4634/73A NO142307C (no) | 1972-12-06 | 1973-12-05 | Fremgangsmaate ved fremstilling av pregnansyrederivater |
FR7343369A FR2209754B1 (US08066781-20111129-C00013.png) | 1972-12-06 | 1973-12-05 | |
AR251376A AR203738A1 (es) | 1972-12-06 | 1973-12-05 | Procedimiento para la produccion de derivados de acidos 3,20,-dioxo-1,4-pregnadienicos,respectivamente 3,20-dioxo-1,4-pregnenicos asi como 2-halogeno-3,20-dioxo-1,4-pregnadienicos |
US421820A US3875194A (en) | 1972-12-06 | 1973-12-05 | Process for the preparation of pregnanoic acid derivatives |
HUSCHE454*1A HU167384B (US08066781-20111129-C00013.png) | 1972-12-06 | 1973-12-05 | |
CS8382A CS165967B2 (US08066781-20111129-C00013.png) | 1972-12-06 | 1973-12-05 | |
GB5663673A GB1456675A (en) | 1972-12-06 | 1973-12-06 | Process for the manufacture of pregnane acids |
CA187,541A CA1007633A (en) | 1972-12-06 | 1973-12-06 | Process for producing pregnane acids |
ZA739298A ZA739298B (en) | 1972-12-06 | 1973-12-06 | Process for the manufacture of pregnane acids |
ES421238A ES421238A1 (es) | 1972-12-06 | 1973-12-06 | Procedimiento para la preparacion de derivados de acido pregnanico. |
BE138584A BE808301A (fr) | 1972-12-06 | 1973-12-06 | Procede de preparation de derives d'acide de pregnane |
JP13671473A JPS5710880B2 (US08066781-20111129-C00013.png) | 1972-12-06 | 1973-12-06 | |
CH1713073A CH606099A5 (US08066781-20111129-C00013.png) | 1972-12-06 | 1973-12-06 | |
NLAANVRAGE7316695,A NL184897C (nl) | 1972-12-06 | 1973-12-06 | Werkwijze voor het bereiden van pregnaanzuurderivaten. |
AT1021173A AT336810B (de) | 1972-12-06 | 1973-12-06 | Verfahren zur herstellung von pregnansaure-derivaten |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2260303A DE2260303C2 (de) | 1972-12-06 | 1972-12-06 | Verfahren zur Herstellung von Pregnansäurederivaten |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2260303A1 DE2260303A1 (de) | 1974-06-12 |
DE2260303C2 true DE2260303C2 (de) | 1983-12-15 |
Family
ID=5863960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2260303A Expired DE2260303C2 (de) | 1972-12-06 | 1972-12-06 | Verfahren zur Herstellung von Pregnansäurederivaten |
Country Status (27)
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919421A (en) * | 1972-12-22 | 1975-11-11 | Schering Ag | Pregnanoic acid derivatives and process for the preparation thereof |
DE2336438C2 (de) * | 1973-07-14 | 1983-07-07 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von 17 β- Oxalylsteroiden |
DD119586A5 (US08066781-20111129-C00013.png) * | 1973-12-21 | 1976-05-05 | ||
CH614960A5 (US08066781-20111129-C00013.png) * | 1976-04-15 | 1979-12-28 | Ciba Geigy Ag | |
CH633562A5 (de) * | 1976-12-10 | 1982-12-15 | Schering Ag | Verfahren zur herstellung neuer kortikoide. |
JPS614680U (ja) * | 1984-06-13 | 1986-01-11 | 株式会社 ソフイア | パチンコ機の入賞装置 |
US5215979A (en) * | 1985-12-19 | 1993-06-01 | Aktiebolaget Draco | 16,17-acetalsubstituted pregnane 21-oic acid derivatives |
-
1972
- 1972-12-06 DE DE2260303A patent/DE2260303C2/de not_active Expired
-
1973
- 1973-11-22 DK DK631373A patent/DK131864C/da not_active IP Right Cessation
- 1973-11-23 FI FI733621A patent/FI52347C/fi active
- 1973-11-25 YU YU3068/73A patent/YU35451B/xx unknown
- 1973-11-26 SE SE7315979A patent/SE399712B/xx unknown
- 1973-11-29 DD DD174979A patent/DD108529A5/xx unknown
- 1973-11-30 AU AU63113/73A patent/AU6311373A/en not_active Expired
- 1973-12-03 IL IL43745A patent/IL43745A/en unknown
- 1973-12-04 SU SU1976253A patent/SU524523A3/ru active
- 1973-12-04 PL PL1973167042A patent/PL89573B1/pl unknown
- 1973-12-04 RO RO7376884A patent/RO71431A/ro unknown
- 1973-12-04 IE IE2192/73A patent/IE38608B1/xx unknown
- 1973-12-05 FR FR7343369A patent/FR2209754B1/fr not_active Expired
- 1973-12-05 CS CS8382A patent/CS165967B2/cs unknown
- 1973-12-05 US US421820A patent/US3875194A/en not_active Expired - Lifetime
- 1973-12-05 HU HUSCHE454*1A patent/HU167384B/hu not_active IP Right Cessation
- 1973-12-05 AR AR251376A patent/AR203738A1/es active
- 1973-12-05 NO NO4634/73A patent/NO142307C/no unknown
- 1973-12-06 ZA ZA739298A patent/ZA739298B/xx unknown
- 1973-12-06 ES ES421238A patent/ES421238A1/es not_active Expired
- 1973-12-06 CH CH1713073A patent/CH606099A5/xx not_active IP Right Cessation
- 1973-12-06 NL NLAANVRAGE7316695,A patent/NL184897C/xx not_active IP Right Cessation
- 1973-12-06 JP JP13671473A patent/JPS5710880B2/ja not_active Expired
- 1973-12-06 BE BE138584A patent/BE808301A/xx not_active IP Right Cessation
- 1973-12-06 GB GB5663673A patent/GB1456675A/en not_active Expired
- 1973-12-06 AT AT1021173A patent/AT336810B/de not_active IP Right Cessation
- 1973-12-06 CA CA187,541A patent/CA1007633A/en not_active Expired
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