CH617940A5 - - Google Patents

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Info

Publication number: CH617940A5
Authority: CH; Switzerland
Prior art keywords: mercury; sulfite; ethynyl; bis; methyl
Prior art date: 1971-08-06

Application number

CH1102172A

Other languages

German (de)

English (en)

Inventor

Helmut Dr Haeuser

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.)

1971-08-06

Filing date

1972-07-24

Publication date

1980-06-30

1971-08-06 Priority claimed from DE19712140291 external-priority patent/DE2140291C3/de

1972-06-16 Priority claimed from DE2230286A external-priority patent/DE2230286C3/de

1972-07-24 Application filed by Schering Ag filed Critical Schering Ag

1980-06-30 Publication of CH617940A5 publication Critical patent/CH617940A5/de

Links

238000000034 method Methods 0.000 description 32
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
-1 acyl radical Chemical class 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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 14
235000019253 formic acid Nutrition 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 10
150000001735 carboxylic acids Chemical class 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
150000002730 mercury Chemical class 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 7
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 7
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000011230 binding agent Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
239000012071 phase Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
SFXKFFXIDKPNHF-UHFFFAOYSA-M mercury(1+);formate Chemical compound [Hg+].[O-]C=O SFXKFFXIDKPNHF-UHFFFAOYSA-M 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052979 sodium sulfide Inorganic materials 0.000 description 3
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
SHZVCTRRRIRFOC-UHFFFAOYSA-N mercury(1+) Chemical class [Hg+] SHZVCTRRRIRFOC-UHFFFAOYSA-N 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000006257 total synthesis reaction Methods 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
YJDYCULVYZDESB-HKQXQEGQSA-N (5r,8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 YJDYCULVYZDESB-HKQXQEGQSA-N 0.000 description 1
WYRCRDCGMYGWKP-YFRXESGTSA-N (8r,9r,10s,13s,14s)-13-methyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical class C1CCC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 WYRCRDCGMYGWKP-YFRXESGTSA-N 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
QMBJSIBWORFWQT-DFXBJWIESA-N Chlormadinone acetate Chemical compound C1=C(Cl)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 QMBJSIBWORFWQT-DFXBJWIESA-N 0.000 description 1
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
XWKUGBVPSRCDNQ-UHFFFAOYSA-N acetic acid;ethenone Chemical class C=C=O.CC(O)=O XWKUGBVPSRCDNQ-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000003152 gestagenic effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002561 ketenes Chemical class 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229960005294 triamcinolone Drugs 0.000 description 1
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 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
- 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
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

CH1102172A 1971-08-06 1972-07-24 CH617940A5 (cs)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19712140291 DE2140291C3 (de)	1971-08-06	1971-08-06	Verfahren zur Herstellung von Pregnan-Derivaten
DE2230286A DE2230286C3 (de)	1972-06-16	1972-06-16	Verfahren zur Herstellung von Pregnan-Derivaten

Publications (1)

Publication Number	Publication Date
CH617940A5 true CH617940A5 (cs)	1980-06-30

Family

ID=25761586

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1102172A CH617940A5 (cs)	1971-08-06	1972-07-24
CH290876A CH621130A5 (cs)	1971-08-06	1976-03-09

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH290876A CH621130A5 (cs)	1971-08-06	1976-03-09

Country Status (17)

Country	Link
US (1)	US3764615A (cs)
JP (1)	JPS5617360B2 (cs)
AT (1)	AT340068B (cs)
BE (1)	BE787242A (cs)
CH (2)	CH617940A5 (cs)
DD (1)	DD99163A5 (cs)
DK (1)	DK130957B (cs)
FR (1)	FR2149911A5 (cs)
GB (1)	GB1403567A (cs)
HU (1)	HU164849B (cs)
IE (1)	IE36592B1 (cs)
IL (1)	IL39898A (cs)
NL (1)	NL7210758A (cs)
PH (1)	PH9396A (cs)
PL (1)	PL82005B1 (cs)
SE (1)	SE377805B (cs)
SU (1)	SU514573A3 (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2246462C3 (de) *	1972-09-21	1981-07-23	Schering Ag Berlin Und Bergkamen, 1000 Berlin	15 α , 16 α -Methylen-4-pregnene, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
DE2625306C2 (de) *	1976-06-02	1978-06-15	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Verfahren zur Herstellung von Pregnan-Derivaten
EP0063368B1 (de) *	1981-04-16	1984-07-25	Richter Gedeon Vegyeszeti Gyar R.T.	Verfahren zur Herstellung von Pregn-4-en-3,20-dionderivaten sowie 17-alpha-Äthinyl-17-beta-trifluoracetoxygon-4-en-3-onderivate und die letzteren enthaltende Arzneimittel
US4588529A (en) *	1985-02-28	1986-05-13	The Upjohn Company	Mercury removal process
HU230788B1 (en)	2013-12-16	2018-05-02	Richter Gedeon Nyrt	Norsteroid intermediates and process for their preparation

0
- BE BE787242D patent/BE787242A/xx unknown
1972
- 1972-07-03 DD DD164134A patent/DD99163A5/xx unknown
- 1972-07-07 DK DK340272AA patent/DK130957B/da unknown
- 1972-07-12 SU SU1809607A patent/SU514573A3/ru active
- 1972-07-13 IL IL39898A patent/IL39898A/xx unknown
- 1972-07-18 GB GB3354772A patent/GB1403567A/en not_active Expired
- 1972-07-20 HU HUSCHE402*1A patent/HU164849B/hu unknown
- 1972-07-24 CH CH1102172A patent/CH617940A5/de not_active IP Right Cessation
- 1972-07-25 IE IE1039/72A patent/IE36592B1/xx unknown
- 1972-08-01 US US00277123A patent/US3764615A/en not_active Expired - Lifetime
- 1972-08-04 SE SE7210201A patent/SE377805B/xx unknown
- 1972-08-04 PL PL1972157122A patent/PL82005B1/pl unknown
- 1972-08-04 AT AT675972A patent/AT340068B/de not_active IP Right Cessation
- 1972-08-04 PH PH13772*UA patent/PH9396A/en unknown
- 1972-08-04 NL NL7210758A patent/NL7210758A/xx not_active Application Discontinuation
- 1972-08-04 FR FR7228238A patent/FR2149911A5/fr not_active Expired
- 1972-08-07 JP JP7902772A patent/JPS5617360B2/ja not_active Expired
1976
- 1976-03-09 CH CH290876A patent/CH621130A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE36592L (en)	1973-02-06
AT340068B (de)	1977-11-25
FR2149911A5 (cs)	1973-03-30
US3764615A (en)	1973-10-09
IL39898A0 (en)	1972-09-28
DK130957B (da)	1975-05-12
DK130957C (cs)	1975-10-06
HU164849B (cs)	1974-04-11
IL39898A (en)	1975-03-13
GB1403567A (en)	1975-08-28
SE377805B (cs)	1975-07-28
NL7210758A (cs)	1973-02-08
SU514573A3 (ru)	1976-05-15
JPS5617360B2 (cs)	1981-04-22
JPS4826751A (cs)	1973-04-09
PH9396A (en)	1975-10-28
PL82005B1 (cs)	1975-10-31
CH621130A5 (cs)	1981-01-15
ATA675972A (de)	1977-03-15
BE787242A (fr)	1973-02-05
IE36592B1 (en)	1976-12-08
DD99163A5 (cs)	1973-07-20

Legal Events

Date	Code	Title	Description
1983-03-31	PL	Patent ceased

Publication	Publication Date	Title
CH533094A (de)	1973-01-31	Verfahren zur Herstellung neuer Steroide
EP0100874B1 (de)	1990-03-07	Neue 6,16-Dimethylkortikoide, ihre Herstellung und Verwendung
DE3243482A1 (de)	1984-05-24	Neue 6(alpha)-methylkortikoide, ihre herstellung und verwendung
CH617940A5 (cs)	1980-06-30
CH639655A5 (de)	1983-11-30	3-acetoxy-9beta,11beta-oxido-pregna-1,3,5-triene und -3,5-diene.
DE2916889A1 (de)	1979-11-08	Verbessertes verfahren fuer die herstellung von 6-halogen-pregnanen
DE1468035A1 (de)	1968-12-12	Verfahren zur Herstellung von 19-Alkylsteroiden
DE3109459A1 (de)	1982-09-23	(delta)(pfeil hoch)9(pfeil hoch)(pfeil hoch)((pfeil hoch)(pfeil hoch)1(pfeil hoch)(pfeil hoch)1(pfeil hoch)(pfeil hoch))(pfeil hoch)- und (delta)(pfeil hoch)1(pfeil hoch)(pfeil hoch)6(pfeil hoch)-21-chlor-20-keto-steroide der pregnan- und d-homo-pregnan-reihe, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte fuer die synthese von hochwirksamen corticoiden
DE2625306C2 (de)	1978-06-15	Verfahren zur Herstellung von Pregnan-Derivaten
DE2140291C3 (de)	1981-08-27	Verfahren zur Herstellung von Pregnan-Derivaten
DE2230286C3 (de)	1981-09-24	Verfahren zur Herstellung von Pregnan-Derivaten
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
DE2023122B2 (de)	1979-03-29	Verfahren zur Herstellung von Pregnen-Derivaten
DE2603545C3 (de)	1980-04-24	Neue 16 a -Methyl-17 a - brom-prednisolon- und prednisonderivate und Verfahren zu deren Herstellung
CH494213A (de)	1970-07-31	Verfahren zur Herstellung von Gonadienonen
EP0164298A2 (de)	1985-12-11	Neue 6alpha-Methyl-D-homo-kortikoide
DE1241825C2 (de)	1975-10-16	Verfahren zur herstellung von 6-chlor-4,6-dienverbindungen der pregnan-, androstan- oder cholestanreihe
DE1568971C3 (de)	1974-03-14	Steroidoxazoline und Verfahren zu ihrer Herstellung
DE2064859B2 (de)	1979-09-13	3,20-dion Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
DE2055221A1 (en)	1972-05-18	17-acyloxy-3-keto-pregn-4-enes prepn - by acylating 17-hydroxy steroids in presence ofstannic chloride
DE1593209C3 (de)	1976-03-04	Verfahren zur 17 alpha-Alkylierung von 20-Ketosteroiden der Pregnanreihe und 17alpha-Alkylsteroide der Pregnanreihe
AT251774B (de)	1967-01-25	Verfahren zur Herstellung von neuen 6α9α-Difluor-16-methylpregnenen und -pregnadienen
DE1468423A1 (de)	1969-01-09	Verfahren zur Herstellung von 7-Alkyl-19-norsteroiden
CH625254A5 (cs)	1981-09-15
DE2211817C3 (de)	1976-12-02	Verfahren zur Herstellung von Dinorcholestan-Derivaten und dazu eingesetzte Verbindungen