BE651926A - - Google Patents

Info

Publication number: BE651926A
Authority: BE; Belgium
Prior art keywords: solution; group; methyl; compound; mixture
Prior art date: 1963-08-19

Application number

BE651926A

Other languages

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.)

1963-08-19

Filing date

1964-08-17

Publication date

1965-02-17

1963-08-19 Priority claimed from CH1020163A external-priority patent/CH424789A/de

1964-08-17 Application filed filed Critical

1965-02-17 Publication of BE651926A publication Critical patent/BE651926A/fr

Links

150000001875 compounds Chemical class 0.000 claims description 49
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
-1 aminopyrazole steroid compounds Chemical class 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 2
150000003855 acyl compounds Chemical class 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 2
150000002429 hydrazines Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
150000003431 steroids Chemical class 0.000 claims description 2
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 177
239000000243 solution Substances 0.000 description 104
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 102
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
239000000203 mixture Substances 0.000 description 71
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 61
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
235000011121 sodium hydroxide Nutrition 0.000 description 23
238000002211 ultraviolet spectrum Methods 0.000 description 22
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
239000012043 crude product Substances 0.000 description 20
229910052943 magnesium sulfate Inorganic materials 0.000 description 20
235000019341 magnesium sulphate Nutrition 0.000 description 20
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000155 melt Substances 0.000 description 17
239000000284 extract Substances 0.000 description 16
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
239000007864 aqueous solution Substances 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
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 12
238000001914 filtration Methods 0.000 description 12
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
229960001866 silicon dioxide Drugs 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000001816 cooling Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000012047 saturated solution Substances 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
239000000126 substance Substances 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
229910000403 monosodium phosphate Inorganic materials 0.000 description 5
235000019799 monosodium phosphate Nutrition 0.000 description 5
239000000047 product Substances 0.000 description 5
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 5
239000003814 drug Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
125000003047 N-acetyl group Chemical group 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
230000001195 anabolic effect Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007790 solid phase Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000003356 anti-rheumatic effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
235000015243 ice cream Nutrition 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
CSSKIQUMIWCMJR-UHFFFAOYSA-N n-(1h-pyrazol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=NN1 CSSKIQUMIWCMJR-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
BQTTYKVRRLHMQQ-ZBKBXNIDSA-N (8r,9s,10s,13r,14s,17r)-17-ethenyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C=C)[C@@H]4[C@@H]3CCC21 BQTTYKVRRLHMQQ-ZBKBXNIDSA-N 0.000 description 1
UQTWKHIKMJNREL-CBQIQWOPSA-N (8s,9s,10r,13r,14s,17r)-17-(2-hydroxyethyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CCO)[C@@H]4[C@@H]3CCC2=C1 UQTWKHIKMJNREL-CBQIQWOPSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101150103171 DARS1 gene Proteins 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
229940123907 Disease modifying antirheumatic drug Drugs 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
101100218337 Gibberella zeae (strain ATCC MYA-4620 / CBS 123657 / FGSC 9075 / NRRL 31084 / PH-1) aurL2 gene Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241001523432 Zale Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001741 anti-phlogistic effect Effects 0.000 description 1
239000003435 antirheumatic agent Substances 0.000 description 1
210000000436 anus Anatomy 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical class CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000005553 drilling Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 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
239000012467 final product Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000004927 fusion Effects 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
230000003236 psychic effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000009758 senescence Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Cephalosporin Compounds (AREA)

BE651926A 1963-08-19 1964-08-17 BE651926A (de)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
CH1020163A CH424789A (de)	1963-08-19	1963-08-19	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
CH106664		1964-01-30
CH291164		1964-03-06
CH436564		1964-04-07
CH657664		1964-05-20

Publications (1)

Publication Number	Publication Date
BE651926A true BE651926A (de)	1965-02-17

Family

ID=27508923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE651926A BE651926A (de)	1963-08-19	1964-08-17

Country Status (3)

Country	Link
BE (1)	BE651926A (de)
ES (1)	ES307699A1 (de)
NL (1)	NL6409415A (de)

1964
- 1964-08-14 NL NL6409415A patent/NL6409415A/xx unknown
- 1964-08-17 BE BE651926A patent/BE651926A/fr unknown
- 1964-12-30 ES ES0307699A patent/ES307699A1/es not_active Expired

Also Published As

Publication number	Publication date
ES307699A1 (es)	1965-07-01
NL6409415A (de)	1965-02-22

Publication	Publication Date	Title
EP0001534B1 (de)	1981-08-12	Pyrrolderivate, Verfahren zu ihrer Herstellung und ihre therapeutischen Verwendungen
EP0382634B1 (de)	1994-05-04	Pyridazin-Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammenstellungen
FR2665441A1 (fr)	1992-02-07	Derives de la n-sulfonyl indoline, leur preparation, les compositions pharmaceutiques en contenant.
EP0310519B1 (de)	1992-08-19	Androstan-17-carbonsäureester, Verfahren zu ihrer Herstellung und Arzneimittel, die sie enthalten
LU83576A1 (fr)	1982-04-14	Nouveaux derives du 4h-1,2,4-triazole,leur preparation,leur application comme medicament,les compositions les renfermant et les intermediaires obtenus
EP0835254B1 (de)	1999-09-01	Oxazolidinone derivate, ihre herstellung und ihre therapeutische verwendung
EP0004494B1 (de)	1982-02-17	1,3-Dihydro-3-(1-(2-(2,3-dihydro-1,4-benzodioxin-2-yl)2-hydroxy-äthyl)piperidin-4-yl)2H-indol-2-on Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zubereitungen
CH627648A5 (fr)	1982-01-29	Nouveaux derives de 20,21-dinoreburnamenine, procede de preparation et compositions pharmaceutiques.
MC511A1 (fr)	1965-08-27	Nouveaux composés hétérocycliques et leur préparation
EP0101383B1 (de)	1986-11-12	14-Aminosteroidderivate, ihre therapeutische Anwendung und Verfahren zu ihrer Herstellung
EP0101659A2 (de)	1984-02-29	14-Amino-Steroidderivate, Verfahren zu ihrer Herstellung und ihre therapeutische Anwendung
CH629821A5 (fr)	1982-05-14	Derives semi-synthetiques de l'oleandomycine et leur procede de preparation.
EP0176444B1 (de)	1989-02-22	Verfahren zur Herstellung von 4H-1,2,4-Triazol-Derivaten, so erhaltene neue Triazole, ihre Verwendung als Arzneimittel und sie enthaltende pharmazeutische Zusammensetzungen
FR2529891A1 (fr)	1984-01-13	Derives du pyridyl-3 alcoxy-5 pyrazole, procede de preparation et application en therapeutique
WO1992021665A1 (fr)	1992-12-10	Nouveaux derives de l'oxazole et leur preparation
BE897152A (fr)	1983-12-28	Derives d'eburnane, procede pour leur preparation et compositions pharmaceutiques qui les contiennent
CH628629A5 (en)	1982-03-15	Derivatives of piperidylindole and their salts
FR2580647A1 (fr)	1986-10-24	Procede de preparation de derives d'eburnamenine et compositions pharmaceutiques les contenant
FR2642757A1 (fr)	1990-08-10	Nouveaux derives de la pyridazine, procede de preparation et compositions pharmaceutiques en contenant
CH426858A (fr)	1966-12-31	Procédé de préparation de nouveaux dérivés colchiciques
BE643084A (de)	1964-07-28
BE568230A (de)
BE531615A (de)
EP0311467B1 (de)	1993-08-04	Verwendung von Pyrrol[3,2,1-hi]indol-Derivaten zur Herstellung eines Arzneimittels zur Behandlung von Diabetes
FR2534583A1 (fr)	1984-04-20	Procede pour la fabrication d'hexahydro-5-hydroxy-4-hydroxymethyl-2h-cyclopenta-(b)-furanne-2-one