DD209635A5 - Verfahren zur herstellung von 11beta-chlor-steroiden - Google Patents

Verfahren zur herstellung von 11beta-chlor-steroiden Download PDF

Info

Publication number: DD209635A5
Authority: DD; German Democratic Republic
Prior art keywords: chloro; acid; methyl; group; general formula
Prior art date: 1982-04-16

Application number

DD83249873A

Other languages

German (de)

English (en)

Inventor

Helmut Hofmeister

Karl Petzoldt

Klaus Annen

Henry Laurent

Rudolf Wiechert

Yukeshige Nishino

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.)

1982-04-16

Filing date

1983-04-14

Publication date

1984-05-16

1983-04-14 Application filed by Schering Ag filed Critical Schering Ag

1984-05-16 Publication of DD209635A5 publication Critical patent/DD209635A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 8
-1 CHLORO STEROIDS Chemical class 0.000 title claims abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000002252 acyl group Chemical group 0.000 claims abstract description 5
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
125000006239 protecting group Chemical group 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
238000010511 deprotection reaction Methods 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 abstract description 4
229910052739 hydrogen Inorganic materials 0.000 abstract 3
239000001257 hydrogen Substances 0.000 abstract 3
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
230000032050 esterification Effects 0.000 description 6
238000005886 esterification reaction Methods 0.000 description 6
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 5
239000012043 crude product Substances 0.000 description 5
230000003152 gestagenic effect Effects 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000003433 contraceptive agent Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
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239000000203 mixture Substances 0.000 description 3
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239000000583 progesterone congener Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound 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 2
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PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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235000011054 acetic acid Nutrition 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000002254 contraceptive effect Effects 0.000 description 2
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
229960002568 ethinylestradiol Drugs 0.000 description 2
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
WQEPLUUGTLDZJY-UHFFFAOYSA-N pentadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
HJAUZNUESCSDDI-GSNZFIHSSA-N (8r,9r,10s,13r,14s)-13-methyl-2,4,5,6,7,8,9,10,11,12,14,15-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@@H]2[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 HJAUZNUESCSDDI-GSNZFIHSSA-N 0.000 description 1
UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 description 1
MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
239000005639 Lauric acid Substances 0.000 description 1
SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
VIWZVFVJPXTXPA-UHFFFAOYSA-N N-(2-Carboxymethyl)-morpholine Chemical compound OC(=O)CN1CCOCC1 VIWZVFVJPXTXPA-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
239000005643 Pelargonic acid Substances 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
102000001307 androgen receptors Human genes 0.000 description 1
108010080146 androgen receptors Proteins 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
230000001380 anti-conceptive effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
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230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
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150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
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239000003085 diluting agent Substances 0.000 description 1
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239000008298 dragée Substances 0.000 description 1
FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
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235000013905 glycine and its sodium salt Nutrition 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
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229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005907 ketalization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
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IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
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239000000243 solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
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GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229960004319 trichloroacetic acid Drugs 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD83249873A 1982-04-16 1983-04-14 Verfahren zur herstellung von 11beta-chlor-steroiden DD209635A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823214689 DE3214689A1 (de)	1982-04-16	1982-04-16	11ss-chlor-steroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate

Publications (1)

Publication Number	Publication Date
DD209635A5 true DD209635A5 (de)	1984-05-16

Family

ID=6161447

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83249873A DD209635A5 (de)	1982-04-16	1983-04-14	Verfahren zur herstellung von 11beta-chlor-steroiden

Country Status (12)

Country	Link
EP (1)	EP0092173B1 (da)
JP (1)	JPS58188899A (da)
AT (1)	ATE18407T1 (da)
AU (1)	AU555284B2 (da)
CA (1)	CA1242697A (da)
DD (1)	DD209635A5 (da)
DE (2)	DE3214689A1 (da)
DK (1)	DK92283A (da)
ES (1)	ES8401096A1 (da)
GR (1)	GR78212B (da)
HU (1)	HU186687B (da)
ZA (1)	ZA832672B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4232521A1 (de) *	1992-09-22	1994-03-24	Schering Ag	Gestagen wirksame 4,5;11,12-Estradiene, Verfahren zu ihrer Herstellung, diese Estradiene enthaltende Arzneimittel sowie deren Verwendung zur Herstellung von Arzneimitteln

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE651797A (da) *	1962-10-17
US3665021A (en) *	1966-07-29	1972-05-23	Glaxo Lab Ltd	9alpha-unsubstituted-11beta-chloro-l9 nos-steroids
NL7209299A (en) *	1972-07-01	1974-01-03		Delta-4-3-oxo-11-beta-halo steroids - with hormonal activity

1982
- 1982-04-16 DE DE19823214689 patent/DE3214689A1/de not_active Withdrawn
1983
- 1983-02-25 DK DK92283A patent/DK92283A/da not_active Application Discontinuation
- 1983-03-01 ES ES520207A patent/ES8401096A1/es not_active Expired
- 1983-03-16 AU AU12487/83A patent/AU555284B2/en not_active Ceased
- 1983-04-13 JP JP58063807A patent/JPS58188899A/ja active Pending
- 1983-04-14 GR GR71089A patent/GR78212B/el unknown
- 1983-04-14 EP EP83103604A patent/EP0092173B1/de not_active Expired
- 1983-04-14 DE DE8383103604T patent/DE3362380D1/de not_active Expired
- 1983-04-14 DD DD83249873A patent/DD209635A5/de unknown
- 1983-04-14 AT AT83103604T patent/ATE18407T1/de not_active IP Right Cessation
- 1983-04-15 ZA ZA832672A patent/ZA832672B/xx unknown
- 1983-04-15 HU HU831327A patent/HU186687B/hu unknown
- 1983-04-15 CA CA000426012A patent/CA1242697A/en not_active Expired

Also Published As

Publication number	Publication date
DK92283D0 (da)	1983-02-25
GR78212B (da)	1984-09-26
EP0092173B1 (de)	1986-03-05
DE3214689A1 (de)	1983-10-27
HU186687B (en)	1985-09-30
CA1242697A (en)	1988-10-04
DE3362380D1 (en)	1986-04-10
ES520207A0 (es)	1983-12-01
AU1248783A (en)	1983-10-20
ES8401096A1 (es)	1983-12-01
JPS58188899A (ja)	1983-11-04
ZA832672B (en)	1983-12-28
ATE18407T1 (de)	1986-03-15
DK92283A (da)	1983-10-17
EP0092173A1 (de)	1983-10-26
AU555284B2 (en)	1986-09-18

Publication	Publication Date	Title
CH630392A5 (de)	1982-06-15	Verfahren zur herstellung neuer delta(15)-steroide.
CH561739A5 (en)	1975-05-15	4-Hydroxy-2-butenoic acid lactone steroid derivs - cardiotonic, anti-inflammatory, hypocholesterolaemic, mineralocorticoid agents
EP0051762B1 (de)	1984-12-19	11-Methylen-delta-15-Steroide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE3628189A1 (de)	1988-02-25	Oestrogen wirksame mittel und 14,17ss-ethano-14ss-estratriene
DE2546062C3 (da)	1980-12-18
EP0017094B1 (de)	1981-11-25	11-Methylensteroide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
EP0092173B1 (de)	1986-03-05	11Beta-Chlor-Steroide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
EP0019247B1 (de)	1981-11-25	16-Alpha-Alkylsteroide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE1793618C3 (de)	1975-10-23	07.03.63 USA 263441 Verfahren zur Herstellung von 3-Hydroxy-1,5-bisdehydrosteroiden der Androstanreihe
EP0034114B1 (de)	1983-02-09	3-Desoxy-delta-15-Steroide, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Präparate
EP0092174B1 (de)	1986-03-05	11Beta-Chlor-Delta15-Steroide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE2706860A1 (de)	1977-08-25	Neue d-homosteroide
DE2636405C2 (de)	1982-07-08	&Delta;&uarr;1&uarr;&uarr;5&uarr;-17&alpha;-Chloräthinyl- und -Propinylsteroide der Östranreihe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Präparate
DE2207421C3 (de)	1981-05-07	15&alpha;, 16&alpha; -Methylen-4-östren-17&beta; -ole bzw. -acylate, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
DE2056512C3 (da)	1980-12-04
DE1493114C3 (da)	1974-05-09
DE2755578A1 (de)	1979-06-13	C-homo-oestratriene
DE2158260C3 (de)	1976-07-01	11-Alkoxysteroide, Verfahren zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen
DE1643005B2 (de)	1974-09-26	15,16beta-Methy len-testosterone, Verfahren zu ihrer Herstellung sowie .diese Steroide enthaltende Mittel
DE2651364A1 (de)	1977-05-12	Neue d-homosteroide
DE1468604B1 (de)	1970-07-02	Verfahren zur Herstellung von 17alpha-Alkyl-,-Alkenyl- oder -Alkinyl-13beta-alkylgon-4-oder-5(10)-en-17beta-ol-3-onen
DE3842646A1 (de)	1990-06-28	9ss,10ss-methylensteroide
DE3939894A1 (de)	1991-06-06	14(alpha),17(alpha)-ethano-16(alpha)-hydroxy-estratriene
DE1144270B (de)	1963-02-28	Verfahren zur Herstellung neuer anabolisch und progestativ wirkender ?-3-Keto-6-methyl-19-norsteroide
DE1219933B (de)	1966-06-30	Verfahren zur Herstellung von 1-Methyl-1, 3, 5(10)-oestratrien-derivaten