CH429719A - Procédé de préparation de nouveaux diamino stéroïdes - Google Patents

Procédé de préparation de nouveaux diamino stéroïdes

Info

Publication number: CH429719A
Authority: CH; Switzerland
Prior art keywords: formula; compound; sep; cholane; 24bis
Prior art date: 1963-03-04

Application number

CH195964A

Other languages

English (en)

French (fr)

Inventor

Bertin Daniel

Nedelec Lucien

Original Assignee

Roussel Uclaf

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.)

1963-03-04

Filing date

1964-02-18

Publication date

1967-02-15

1963-03-04 Priority claimed from FR926732A external-priority patent/FR1453206A/fr

1964-02-18 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1965-02-18 Priority to BR16730465A priority Critical patent/BR6567304D0/pt

1967-02-15 Publication of CH429719A publication Critical patent/CH429719A/fr

Links

238000000034 method Methods 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 16
150000003431 steroids Chemical class 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 29
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 25
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
-1 lithium aluminum hydride Chemical compound 0.000 claims description 15
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
230000032050 esterification Effects 0.000 claims description 6
238000005886 esterification reaction Methods 0.000 claims description 6
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 claims description 6
239000003513 alkali Substances 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
239000012280 lithium aluminium hydride Substances 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
239000012320 chlorinating reagent Substances 0.000 claims description 2
238000005660 chlorination reaction Methods 0.000 claims description 2
150000001805 chlorine compounds Chemical class 0.000 claims description 2
150000004985 diamines Chemical class 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
125000005905 mesyloxy group Chemical group 0.000 claims description 2
150000003128 pregnanes Chemical class 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
239000000243 solution Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
239000000047 product Substances 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
229960001701 chloroform Drugs 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000012267 brine Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
230000002048 spasmolytic effect Effects 0.000 description 5
QSHQKIURKJITMZ-OBUPQJQESA-N 5β-cholane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC)[C@@]2(C)CC1 QSHQKIURKJITMZ-OBUPQJQESA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229960001407 sodium bicarbonate Drugs 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000012265 solid product Substances 0.000 description 3
229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
229960004373 acetylcholine Drugs 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
210000001367 artery Anatomy 0.000 description 2
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
229910001626 barium chloride 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
230000015572 biosynthetic process Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000812 cholinergic antagonist Substances 0.000 description 2
230000008602 contraction Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229940093476 ethylene glycol Drugs 0.000 description 2
239000000284 extract Substances 0.000 description 2
210000001105 femoral artery Anatomy 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
239000005457 ice water Substances 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
229960001789 papaverine Drugs 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
229940124549 vasodilator Drugs 0.000 description 2
239000003071 vasodilator agent Substances 0.000 description 2
230000002861 ventricular Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
BDCLDNALSPBWPQ-UHFFFAOYSA-N 3-oxohexanoic acid Chemical class CCCC(=O)CC(O)=O BDCLDNALSPBWPQ-UHFFFAOYSA-N 0.000 description 1
JWZMCIVGRRFEEX-UHFFFAOYSA-N 5-tert-butylfuran-2-carboxylic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)O1 JWZMCIVGRRFEEX-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
208000005392 Spasm Diseases 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
206010047139 Vasoconstriction Diseases 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
229940045511 barium chloride Drugs 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000001595 contractor effect Effects 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
PTAQBBGLTIODMY-UHFFFAOYSA-N cyclopropylmethyl hydrogen carbonate Chemical compound OC(=O)OCC1CC1 PTAQBBGLTIODMY-UHFFFAOYSA-N 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000004674 formic acids Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
238000005360 mashing Methods 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
150000002814 niacins Chemical class 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000003836 peripheral circulation Effects 0.000 description 1
239000000810 peripheral vasodilating agent Substances 0.000 description 1
229960002116 peripheral vasodilator Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
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
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000003033 spasmogenic effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
230000009278 visceral effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to 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
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
- 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
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
- C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
- 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
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals

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

CH195964A 1963-03-04 1964-02-18 Procédé de préparation de nouveaux diamino stéroïdes CH429719A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
BR16730465A BR6567304D0 (pt)	1964-02-18	1965-02-18	Processo para a fabricacao de um hidrolisado de levedura

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR926732A FR1453206A (fr)	1963-03-04	1963-03-04	Diamino stéroïdes et procédé de préparation
FR933956A FR2810M (fr)	1963-03-04	1963-05-07	Nouveau médicament notamment pour le traitement des spasmes d'origine coronarienne ou viscérale.

Publications (1)

Publication Number	Publication Date
CH429719A true CH429719A (fr)	1967-02-15

Family

ID=26200070

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH195964A CH429719A (fr)	1963-03-04	1964-02-18	Procédé de préparation de nouveaux diamino stéroïdes

Country Status (3)

Country	Link
CH (1)	CH429719A (da)
DK (1)	DK115471B (da)
GB (2)	GB1055927A (da)

1964
- 1964-02-18 CH CH195964A patent/CH429719A/fr unknown
- 1964-03-02 DK DK103364A patent/DK115471B/da unknown
- 1964-03-04 GB GB3723866A patent/GB1055927A/en not_active Expired
- 1964-03-04 GB GB921064A patent/GB1055926A/en not_active Expired

Also Published As

Publication number	Publication date
GB1055927A (en)	1967-01-18
GB1055926A (en)	1967-01-18
DK115471B (da)	1969-10-13

Publication	Publication Date	Title
LU82387A1 (fr)	1980-07-31	Esters d'acyl-carnitines,leur procede de preparation et compositions pharmaceutiques contenant ces esters
CH628344A5 (fr)	1982-02-26	Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels.
EP0073161B1 (fr)	1986-10-22	Nouveaux dérivés de la pyrazine actifs sur le système nerveux central
BE898024A (fr)	1984-04-19	Derives de 1,4-dihydropyridine et compositions pharmaceutiques a action vasodilatatrice les contenant.
BE658748A (da)	1965-07-26
FR2460287A1 (fr)	1981-01-23	9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique
JPH0219822B2 (da)	1990-05-07
EP0021940B1 (fr)	1983-01-19	Nouveaux dérivés aminés du benzothiazole, leur procédé de préparation et leur application en thérapeutique
EP0239436B1 (fr)	1990-06-20	Nouveau dérivé tricyclique dénommé acide (chloro-3 méthyl-6 dioxo-5,5 dihydro-6, 11 dibenzo (c,f) thiazépine (1,2) yl-11 amino) -5 pentanoique, son procédé de préparation et les compositions pharmaceutiques qui le contiennent
EP0089894B1 (fr)	1986-06-11	(Benzimidazolyl-1)-1,N-((hydroxy-4 méthoxy-3 phényl)-2 hydroxy-2 éthyl) amino-3 butane et ses sels et hydrates à activité bêta-adrénergique, leurs applications thérapeutiques, et procédé pour les préparer
FR2634766A1 (fr)	1990-02-02	Acides (rs)-2-(2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofurannyl)-acetiques, et acides 2-(2,3-dihydro-5-acyloxy-4,6,7-trimethylbenzofurannyl)-acetiques et leurs esters, utiles comme medicaments mucoregulateurs et anti-ischemiques, procede pour leur preparation et compositions pharmaceutiques les contenant
EP0004494A1 (fr)	1979-10-03	Nouveaux dérivés de 1,3-dihydro 3-(1-(2-(2,3-dihydro 1,4-benzo-dioxin-2-yl)2-hydroxy éthyl)pipéridin-4-yl)2H-indol 2-one, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant
FR2458534A1 (fr)	1981-01-02	2-propyl-pentanoate de pivaloyloxymethyle, son procede de preparation et son application en therapeutique
CH429719A (fr)	1967-02-15	Procédé de préparation de nouveaux diamino stéroïdes
BE890948A (fr)	1982-02-15	Derives de l'acide anthranilique
EP0130882B1 (fr)	1987-01-07	Dérivés de l'acide bicyclo (3.2.1.) octane carboxylique, leur procédé de préparation et leur application thérapeutique
CH637650A5 (fr)	1983-08-15	Procede de preparation d'un acide chromone carboxylique.
WO1996027593A1 (fr)	1996-09-12	Analogues de l'arginine ayant une activite en tant qu'inhibiteurs de la no synthase
CH387058A (fr)	1965-01-31	Procédé de préparation d'esters de thréo-1-p-nitrophényl-2-dichloracétamidopropane-1,3-diols et d'amino-acides
EP0005422B1 (fr)	1982-10-27	Dérivés d'acides oméga-dialkylalkanoiques, leurs procédés de préparation ainsi que leur utilisation en thérapeutique
EP0275221B1 (fr)	1991-04-17	Nouveaux dérivés du N-(1H-indol 4-yl) benzamide ainsi que leurs sels, leur application à titre de médicaments et les compositions les renfermant
CH658786A5 (fr)	1986-12-15	Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters.
FR2726268A1 (fr)	1996-05-03	Nouvelles o-arylmethyl n-(thio)acyl hydroxylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent
CH411820A (fr)	1966-04-30	Procédé de préparation de nouveaux composés hépariniques utilisables, notamment, pour le traitement des troubles de la coagulabilité sanguine
CH407161A (fr)	1966-02-15	Procédé de préparation de nouveaux dérivés de l'acétanilide