DD221460A5 - Verfahren zur herstellung von 17-halogen-ethinyl-steroiden - Google Patents

Verfahren zur herstellung von 17-halogen-ethinyl-steroiden Download PDF

Info

Publication number: DD221460A5
Authority: DD; German Democratic Republic
Prior art keywords: group; water; ethynyl; radical; preparation
Prior art date: 1983-04-25

Application number

DD84262213A

Other languages

German (de)

English (en)

Inventor

Helmut Hofmeister

Henry Laurent

Klaus Annen

Rudolf Wiechert

Original Assignee

Schering Ag

Priority date (The priority date 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 date listed.)

1983-04-25

Filing date

1984-04-23

Publication date

1985-04-24

1984-04-23 Application filed by Schering Ag filed Critical Schering Ag

1985-04-24 Publication of DD221460A5 publication Critical patent/DD221460A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims abstract description 10
229910052736 halogen Inorganic materials 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims abstract description 3
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims abstract description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 3
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims abstract description 3
229910052740 iodine Chemical group 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
125000004980 cyclopropylene group Chemical group 0.000 claims 1
-1 ethynyl steroid Chemical class 0.000 abstract description 9
239000003795 chemical substances by application Substances 0.000 abstract description 6
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract description 6
239000012336 iodinating agent Substances 0.000 abstract description 4
239000012442 inert solvent Substances 0.000 abstract description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract description 2
YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 abstract description 2
125000002346 iodo group Chemical group I* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 36
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
229910001961 silver nitrate Inorganic materials 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
239000005457 ice water Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
150000003431 steroids Chemical class 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000000354 decomposition reaction Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 5
239000006260 foam Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 3
IBWNBQOTQRFHOF-OBQKJFGGSA-N (8r,9s,10r,13s,14s,17r)-17-(2-bromoacetyl)-17-hydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CBr)[C@@H]4[C@@H]3CCC2=C1 IBWNBQOTQRFHOF-OBQKJFGGSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
ZYHLPZVSTCBHPU-LHZXLZLDSA-N [(8r,9s,10r,13s,14s,17r)-17-(2-bromoacetyl)-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl] formate Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(OC=O)C(=O)CBr)[C@@H]4[C@@H]3CCC2=C1 ZYHLPZVSTCBHPU-LHZXLZLDSA-N 0.000 description 2
QOVZAHHZLFRAPE-ZGFYZEPBSA-N [(8s,10s,13s,14s,17r)-17-(2-bromoacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl] formate Chemical compound O=C1CC[C@]2(C)C3=CC[C@](C)([C@@](CC4)(OC=O)C(=O)CBr)[C@@H]4[C@@H]3CCC2=C1 QOVZAHHZLFRAPE-ZGFYZEPBSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
150000001885 cortisol derivatives Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003756 stirring Methods 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
XTGYEAXBNRVNQU-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-iodopropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)I XTGYEAXBNRVNQU-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GJNCXCPHNRATIQ-UHFFFAOYSA-N 1-bromoazepan-2-one Chemical compound BrN1CCCCCC1=O GJNCXCPHNRATIQ-UHFFFAOYSA-N 0.000 description 1
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
WVRZJAMAOJQSRN-JZTHCNPZSA-N 21-Acetyloxy-17-hydroxypregna-1,4-diene-3,20-dione Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2 WVRZJAMAOJQSRN-JZTHCNPZSA-N 0.000 description 1
QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
YUWPMEXLKGOSBF-GACAOOTBSA-N Anecortave acetate Chemical compound O=C1CC[C@]2(C)C3=CC[C@]4(C)[C@](C(=O)COC(=O)C)(O)CC[C@H]4[C@@H]3CCC2=C1 YUWPMEXLKGOSBF-GACAOOTBSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical class OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CCOCQBGNNNCQDS-LHZXLZLDSA-N [(8r,9s,10r,13s,14s,17r)-17-(2-bromoacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] formate Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(OC=O)C(=O)CBr)[C@@H]4[C@@H]3CCC2=C1 CCOCQBGNNNCQDS-LHZXLZLDSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
229930182833 estradiol Natural products 0.000 description 1
229960005309 estradiol Drugs 0.000 description 1
GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical class C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
150000004674 formic acids Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002730 mercury Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003126 pregnane derivatives Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
229940071536 silver acetate Drugs 0.000 description 1
229940096017 silver fluoride Drugs 0.000 description 1
REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
229910000367 silver sulfate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
239000008259 solid foam Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide 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
- C07J5/0046—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 substituted in position 17 alfa
- C07J5/0053—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 substituted in position 17 alfa not substituted in position 16
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Silicates, Zeolites, And Molecular Sieves (AREA)
Apparatus For Radiation Diagnosis (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD84262213A 1983-04-25 1984-04-23 Verfahren zur herstellung von 17-halogen-ethinyl-steroiden DD221460A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19833315324 DE3315324A1 (de)	1983-04-25	1983-04-25	Verfahren zur herstellung von 17(alpha)-(br oder j)-ethinyl-17ss-or-steroiden

Publications (1)

Publication Number	Publication Date
DD221460A5 true DD221460A5 (de)	1985-04-24

Family

ID=6197529

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84262213A DD221460A5 (de)	1983-04-25	1984-04-23	Verfahren zur herstellung von 17-halogen-ethinyl-steroiden

Country Status (15)

Country	Link
US (1)	US4567002A (es)
EP (1)	EP0123241B1 (es)
JP (1)	JPS6034990A (es)
AT (1)	ATE41160T1 (es)
CA (1)	CA1254883A (es)
CS (1)	CS252474B2 (es)
DD (1)	DD221460A5 (es)
DE (2)	DE3315324A1 (es)
DK (1)	DK206684A (es)
ES (1)	ES531900A0 (es)
FI (1)	FI841620A7 (es)
GR (1)	GR81486B (es)
HU (1)	HU193568B (es)
PL (1)	PL143460B1 (es)
SU (1)	SU1389681A3 (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3434448A1 (de) *	1984-09-17	1986-03-27	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur herstellung von pregnan-derivaten
US5972922A (en) *	1990-06-11	1999-10-26	Alcon Laboratories, Inc.	Steroids which inhibit angiogenesis
JPH05507912A (ja) *	1990-06-11	1993-11-11	アルコン・ラボラトリーズ，インコーポレイテッド	血管形成を阻害するステロイド
HU210076B (en) *	1992-11-02	1995-01-30	Tuba	Process for producing androstane derivatives substituted with quaternisaeted amino group in 16-position and for producing pharmaceutical compositions containing them

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3067214A (en) *	1960-04-20	1962-12-04	Merck & Co Inc	Haloethisterone compounds
US3211725A (en) *	1960-04-20	1965-10-12	Merck & Co Inc	6alpha-methyl-21 halo nor ethisterones and intermediates in the preparation thereof
US3347880A (en) *	1962-10-05	1967-10-17	Schering Corp	17alpha-halogenoethinylestranes
DE2625306C2 (de) *	1976-06-02	1978-06-15	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Verfahren zur Herstellung von Pregnan-Derivaten
DE3242892C1 (de) *	1982-11-16	1984-07-12	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur Herstellung von 17alpha-(Br oder J)-ethinyl-17ss-hydroxysteroiden

1983
- 1983-04-25 DE DE19833315324 patent/DE3315324A1/de not_active Withdrawn
1984
- 1984-04-14 AT AT84104258T patent/ATE41160T1/de not_active IP Right Cessation
- 1984-04-14 EP EP84104258A patent/EP0123241B1/de not_active Expired
- 1984-04-14 DE DE8484104258T patent/DE3477000D1/de not_active Expired
- 1984-04-23 DD DD84262213A patent/DD221460A5/de not_active IP Right Cessation
- 1984-04-23 SU SU843728751A patent/SU1389681A3/ru active
- 1984-04-24 HU HU841573A patent/HU193568B/hu not_active IP Right Cessation
- 1984-04-24 PL PL1984247376A patent/PL143460B1/pl unknown
- 1984-04-24 CA CA000452650A patent/CA1254883A/en not_active Expired
- 1984-04-25 US US06/603,855 patent/US4567002A/en not_active Expired - Fee Related
- 1984-04-25 ES ES531900A patent/ES531900A0/es active Granted
- 1984-04-25 CS CS843070A patent/CS252474B2/cs unknown
- 1984-04-25 FI FI841620A patent/FI841620A7/fi not_active Application Discontinuation
- 1984-04-25 DK DK206684A patent/DK206684A/da not_active Application Discontinuation
- 1984-04-25 GR GR74490A patent/GR81486B/el unknown
- 1984-04-25 JP JP59082111A patent/JPS6034990A/ja active Pending

Also Published As

Publication number	Publication date
JPS6034990A (ja)	1985-02-22
ATE41160T1 (de)	1989-03-15
EP0123241A1 (de)	1984-10-31
DE3315324A1 (de)	1984-10-31
ES8506045A1 (es)	1985-07-01
CA1254883A (en)	1989-05-30
FI841620A0 (fi)	1984-04-25
PL247376A1 (en)	1985-04-09
EP0123241B1 (de)	1989-03-08
HU193568B (en)	1987-10-28
DK206684D0 (da)	1984-04-25
PL143460B1 (en)	1988-02-29
SU1389681A3 (ru)	1988-04-15
DE3477000D1 (en)	1989-04-13
ES531900A0 (es)	1985-07-01
US4567002A (en)	1986-01-28
DK206684A (da)	1984-10-26
CS307084A2 (en)	1987-01-15
CS252474B2 (en)	1987-09-17
FI841620A7 (fi)	1984-10-26
HUT34215A (en)	1985-02-28
GR81486B (es)	1984-12-11

Publication	Publication Date	Title
DD145918A5 (de)	1981-01-14	Verfahren zur herstellung von este n von androstadien-17-carbonsaeuren
EP0072547B1 (de)	1986-03-26	Neue 6-alpha-Methylprednisolon-Derivate ihre Herstellung und Verwendung
EP0100874B1 (de)	1990-03-07	Neue 6,16-Dimethylkortikoide, ihre Herstellung und Verwendung
DE69709655T2 (de)	2002-09-12	Verfahren zur herstellung von 17-estern von 9alpha,21-dihalopregan-11beta,17alpha-diol-20-onen
HU216638B (hu)	1999-07-28	Új eljárás 11-oxo-szteroid-származékok előállítására
DE69227478T2 (de)	1999-06-02	Neue Steroidderivate vom Typ Pregna-1,4-diene-3,20-dion, ihre Herstellung und Verwendung zur Herstellung der substituierten 16,17-Methylendioxyderivate und neuen Zwischenprodukten
CH629825A5 (de)	1982-05-14	Verfahren zur herstellung von terpenoiden estern von steroiden der pregnanreihe.
EP0181442B1 (de)	1989-07-12	Verfahren zur Herstellung von Pregnan-Derivaten
DE2715863A1 (de)	1977-11-03	Verfahren zur herstellung von steroidcarbonsaeuren und ihren estern
DD221460A5 (de)	1985-04-24	Verfahren zur herstellung von 17-halogen-ethinyl-steroiden
EP0072546A1 (de)	1983-02-23	Neue Hydrocortison-Derivate, ihre Herstellung und Verwendung
EP0149464A2 (de)	1985-07-24	6-Alpha,16-beta-Dimethylkortikoide
CH634085A5 (de)	1983-01-14	Verfahren zur herstellung neuer kortikoide.
DE2365992C3 (de)	1982-05-19	6&alpha;-Fluor-17,21-dihydroxy-16&beta;-methylpregna-4,9(11)-dien-3,20-dion-17,21-diacetat und Verfahren zu dessen Herstellung
AT390794B (de)	1990-06-25	Verfahren zur herstellung von neuen steroidverbindungen
EP0149222A2 (de)	1985-07-24	Neue 6alpha, 16alpha-Dimethylkortikoide
DE2632678C2 (de)	1986-02-27	6&alpha;-Fluor-12&alpha;-Halogen-Kortikoide und Verfahren zu ihrer Herstellung
DE2801415A1 (de)	1978-07-20	Neue in 11beta-stellung substituierte steroid-derivate sowie deren herstellungsverfahren
EP0164298A2 (de)	1985-12-11	Neue 6alpha-Methyl-D-homo-kortikoide
DE2754759C2 (de)	1987-03-26	3&alpha;-Hydroxy-5&beta;-cholest-24-en
CH651819A5 (de)	1985-10-15	Basen-katalysierte acylierung mit enol-estern.
DE2204360C2 (de)	1982-11-04	Neue Pregnansäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
AT364098B (de)	1981-09-25	Verfahren zur herstellung von neuen estern von androstadien-17-carbonsaeuren
AT362889B (de)	1981-06-25	Verfahren zur herstellung von neuen estern von androstadien-17-carbonsaeuren
AT275059B (de)	1969-10-10	Vefahren zur Herstellung von neuen 17α-Cyanäthinylsteroiden

Legal Events

Date	Code	Title	Description
1994-01-27	PV	Patent disclaimer (addendum to changes before extension act)