PL31318B1 - - Google Patents
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- Publication number
- PL31318B1 PL31318B1 PL31318A PL3131836A PL31318B1 PL 31318 B1 PL31318 B1 PL 31318B1 PL 31318 A PL31318 A PL 31318A PL 3131836 A PL3131836 A PL 3131836A PL 31318 B1 PL31318 B1 PL 31318B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compound
- treated
- solution
- androstenedione
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 3
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 claims description 2
- 229960005471 androstenedione Drugs 0.000 claims description 2
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- -1 hydrogen compound Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Description
Ulo ^/zz a Wykryto, ze mozna otrzymywac andros- je srodkami odszczepiajacymi chlorowco- tendion o wzorze III, jesli na zwiazek o wodór, np. aminami trzeciorzedowymi, jak wzorze I dziala sie chlorowcem i otrzyma- pirydyna, chinolina albo dwumetyloani- ny chlorowcodwuketon o wzorze II traktu- lina.CH* CHa CHS O CH. 0 = 0= 0 = H Hal I II Otrzymany zwiazek wykazuje silne dzia- Przyklad. 2,88 g zwiazku o wzorze I lanie na grzebien kaploni. Powinien znalezc (etiocholandionu) rozpuszcza sie w 40 cm3 zastosowanie lecznicze, lodowatego kwasu octowego i do tego roz-tworu wkrapla sie roztwór 1,6 g broihu w 10 cm3 lodowatego kwasu octowego. Bar¬ dzo szybko nastepuje odbarwienie roztworu.Produkt reakcji wytraca sie woda; oczysz¬ cza sie go przez przekrystalizowanie z al¬ koholu. W celu oilszczepienia bromowodo- ru otrzymany zwiazek o wzorze II, w któ¬ rym Hal = brom, ogrzewa sie do wfzenia w 50 cm3 suchej pirydyny w ciagu 15 go¬ dzin. Po rozcienczeniu woda zobojetnia sie pirydyne rozcienczonym kwasem siarko¬ wym i wytracony androstendion wyciaga sie eterem. Roztwór eterowy przemywa sie rozcienczonym roztworem sody i woda, su¬ szy nad siarczanem sodowym i odparowu¬ je. Przez przekrystalizowanie z heksanu otrzymuje sie czysty A 4,5-androstendion- (3,17) o punkcie topnienia 172—173°C. PL
Claims (1)
1. Zastrzezenie patentowe. Sposób wytwarzania androstendionu — (3,17), znamienny tym, ze na zwiazek o wzorze I (etiocholandion) dziala sie chlo¬ rowcem i otrzymany chlorowcodwuketon traktuje srodkami odszczepiajacymi chlo¬ rowcowodór. Gesel lschaf t fiirC hemische Industrie in Bascl Zastepca: M. Skrzypkowski rzecznik -patentowy 40248 PL
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL31318B1 true PL31318B1 (pl) | 1943-01-30 |
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