BE890477A - Quinolones, leurs procedes de preparation et composition therapeutique les contenant - Google Patents
Quinolones, leurs procedes de preparation et composition therapeutique les contenant Download PDFInfo
- Publication number
- BE890477A BE890477A BE0/206048A BE206048A BE890477A BE 890477 A BE890477 A BE 890477A BE 0/206048 A BE0/206048 A BE 0/206048A BE 206048 A BE206048 A BE 206048A BE 890477 A BE890477 A BE 890477A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- compound
- quinolone
- general formula
- new
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 68
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 13
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 13
- 230000001225 therapeutic effect Effects 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 130
- 239000002775 capsule Substances 0.000 claims description 9
- -1 methane thiolate anion Chemical class 0.000 claims description 8
- 150000007660 quinolones Chemical class 0.000 claims description 6
- 239000000829 suppository Substances 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 238000002844 melting Methods 0.000 description 55
- 230000008018 melting Effects 0.000 description 53
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000011928 denatured alcohol Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 238000009835 boiling Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 12
- 230000036772 blood pressure Effects 0.000 description 11
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 11
- 239000012265 solid product Substances 0.000 description 11
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 150000003568 thioethers Chemical class 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000004927 fusion Effects 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000539 dimer Substances 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000001506 calcium phosphate Substances 0.000 description 4
- 229910000389 calcium phosphate Inorganic materials 0.000 description 4
- 235000011010 calcium phosphates Nutrition 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 239000002702 enteric coating Substances 0.000 description 4
- 238000009505 enteric coating Methods 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 150000004965 peroxy acids Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BLENHSITVMPXJB-UHFFFAOYSA-N 2-methyl-3h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CC(C)=NC2=C1 BLENHSITVMPXJB-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 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 3
- 241000124008 Mammalia Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 2
- GENAIPOCRXECKE-UHFFFAOYSA-N 1-methyl-3-(methylsulfonylmethyl)quinolin-4-one Chemical compound C1=CC=C2N(C)C=C(CS(C)(=O)=O)C(=O)C2=C1 GENAIPOCRXECKE-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- KAGQRUNOAPAMCZ-UHFFFAOYSA-N 4-chloro-3-(chloromethyl)quinoline Chemical compound C1=CC=CC2=C(Cl)C(CCl)=CN=C21 KAGQRUNOAPAMCZ-UHFFFAOYSA-N 0.000 description 2
- PAJPXBASGXTLSS-UHFFFAOYSA-N 7-ethyl-1h-quinolin-4-one Chemical compound OC1=CC=NC2=CC(CC)=CC=C21 PAJPXBASGXTLSS-UHFFFAOYSA-N 0.000 description 2
- DAVZFKTUWRBWKI-UHFFFAOYSA-N 7-tert-butyl-1h-quinolin-4-one Chemical compound OC1=CC=NC2=CC(C(C)(C)C)=CC=C21 DAVZFKTUWRBWKI-UHFFFAOYSA-N 0.000 description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical compound C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 241000212342 Sium Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- HXQLLNRTDQHYAT-UHFFFAOYSA-N 1-ethyl-3-(methylsulfonylmethyl)quinolin-4-one Chemical compound C1=CC=C2N(CC)C=C(CS(C)(=O)=O)C(=O)C2=C1 HXQLLNRTDQHYAT-UHFFFAOYSA-N 0.000 description 1
- HGYSLLDCNCCEHQ-UHFFFAOYSA-N 1-methyl-3-(methylsulfanylmethyl)quinolin-4-one Chemical compound C1=CC=C2C(=O)C(CSC)=CN(C)C2=C1 HGYSLLDCNCCEHQ-UHFFFAOYSA-N 0.000 description 1
- ULBQLDYBBSPRAO-UHFFFAOYSA-N 1-methyl-3-(methylsulfinylmethyl)quinolin-4-one Chemical compound C1=CC=C2N(C)C=C(CS(C)=O)C(=O)C2=C1 ULBQLDYBBSPRAO-UHFFFAOYSA-N 0.000 description 1
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- AGQGLPYSZGPVJD-UHFFFAOYSA-N 2-(methylsulfonylmethyl)-3H-quinolin-4-one Chemical compound CS(=O)(=O)CC1=NC2=CC=CC=C2C(C1)=O AGQGLPYSZGPVJD-UHFFFAOYSA-N 0.000 description 1
- AVGZBPIAVRBAMJ-UHFFFAOYSA-N 3-(chloromethyl)-1,6-dimethylquinolin-4-one;hydrochloride Chemical compound Cl.CN1C=C(CCl)C(=O)C2=CC(C)=CC=C21 AVGZBPIAVRBAMJ-UHFFFAOYSA-N 0.000 description 1
- GQVBDXKXBACRJS-UHFFFAOYSA-N 3-(chloromethyl)-1-methylquinolin-4-one;hydrochloride Chemical compound Cl.C1=CC=C2N(C)C=C(CCl)C(=O)C2=C1 GQVBDXKXBACRJS-UHFFFAOYSA-N 0.000 description 1
- ZHUWLJQLVPEJAX-UHFFFAOYSA-N 3-(chloromethyl)-7-methoxy-1-methylquinolin-4-one;hydrochloride Chemical compound Cl.CN1C=C(CCl)C(=O)C=2C1=CC(OC)=CC=2 ZHUWLJQLVPEJAX-UHFFFAOYSA-N 0.000 description 1
- ZDMCRIIVTKCDTL-UHFFFAOYSA-N 3-(chloromethyl)-8-methoxy-1-methylquinolin-4-one;hydrochloride Chemical compound Cl.CN1C=C(CCl)C(=O)C2=C1C(OC)=CC=C2 ZDMCRIIVTKCDTL-UHFFFAOYSA-N 0.000 description 1
- QSSCRSRXDYDUBW-UHFFFAOYSA-N 3-(hydroxymethyl)-1,6-dimethylquinolin-4-one Chemical compound CN1C=C(CO)C(=O)C2=CC(C)=CC=C21 QSSCRSRXDYDUBW-UHFFFAOYSA-N 0.000 description 1
- GWADLGFXKHXRAE-UHFFFAOYSA-N 3-(hydroxymethyl)-1-propylquinolin-4-one Chemical compound C1=CC=C2N(CCC)C=C(CO)C(=O)C2=C1 GWADLGFXKHXRAE-UHFFFAOYSA-N 0.000 description 1
- BRNXLMHMXUEFTG-UHFFFAOYSA-N 3-(hydroxymethyl)-6-methyl-1h-quinolin-4-one Chemical compound N1C=C(CO)C(=O)C2=CC(C)=CC=C21 BRNXLMHMXUEFTG-UHFFFAOYSA-N 0.000 description 1
- YOGIENHSLIMXBF-UHFFFAOYSA-N 3-(hydroxymethyl)-7-(trifluoromethyl)-1h-quinolin-4-one Chemical compound FC(F)(F)C1=CC=C2C(=O)C(CO)=CNC2=C1 YOGIENHSLIMXBF-UHFFFAOYSA-N 0.000 description 1
- JXQIJELDHBTKMY-UHFFFAOYSA-N 3-(hydroxymethyl)-7-methoxy-1h-quinolin-4-one Chemical compound OC1=C(CO)C=NC2=CC(OC)=CC=C21 JXQIJELDHBTKMY-UHFFFAOYSA-N 0.000 description 1
- RGOIYHZRKVXSRA-UHFFFAOYSA-N 3-(hydroxymethyl)-8-methoxy-1-methylquinolin-4-one Chemical compound CN1C=C(CO)C(=O)C2=C1C(OC)=CC=C2 RGOIYHZRKVXSRA-UHFFFAOYSA-N 0.000 description 1
- UONOLAIMBLRFOG-UHFFFAOYSA-N 3-(hydroxymethyl)-8-methoxy-1h-quinolin-4-one Chemical compound OCC1=CN=C2C(OC)=CC=CC2=C1O UONOLAIMBLRFOG-UHFFFAOYSA-N 0.000 description 1
- OUVWZMINQAWKSB-UHFFFAOYSA-N 3-(methylsulfanylmethyl)-1-propylquinolin-4-one Chemical compound C1=CC=C2N(CCC)C=C(CSC)C(=O)C2=C1 OUVWZMINQAWKSB-UHFFFAOYSA-N 0.000 description 1
- JTQOWYDPSFLWCP-UHFFFAOYSA-N 3-(methylsulfinylmethyl)-1h-quinolin-4-one Chemical compound C1=CC=CC2=C(O)C(CS(=O)C)=CN=C21 JTQOWYDPSFLWCP-UHFFFAOYSA-N 0.000 description 1
- IBPBVKWAGZDLML-UHFFFAOYSA-N 3-(methylsulfonylmethyl)-1-propylquinolin-4-one Chemical compound C1=CC=C2N(CCC)C=C(CS(C)(=O)=O)C(=O)C2=C1 IBPBVKWAGZDLML-UHFFFAOYSA-N 0.000 description 1
- AMKPQMFZCBTTAT-UHFFFAOYSA-N 3-ethylaniline Chemical compound CCC1=CC=CC(N)=C1 AMKPQMFZCBTTAT-UHFFFAOYSA-N 0.000 description 1
- DPKTVUKEPNBABS-UHFFFAOYSA-N 3-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC(N)=C1 DPKTVUKEPNBABS-UHFFFAOYSA-N 0.000 description 1
- UVBNWRMZMQJLKE-UHFFFAOYSA-N 4-chloro-3-(methylsulfonylmethyl)quinoline Chemical compound C1=CC=CC2=C(Cl)C(CS(=O)(=O)C)=CN=C21 UVBNWRMZMQJLKE-UHFFFAOYSA-N 0.000 description 1
- XXGUQCVVGPZTPF-UHFFFAOYSA-N 6-chloro-1h-quinolin-4-one Chemical compound N1C=CC(=O)C2=CC(Cl)=CC=C21 XXGUQCVVGPZTPF-UHFFFAOYSA-N 0.000 description 1
- BYZXOYSEYWCLOK-UHFFFAOYSA-N 6-fluoro-1h-quinolin-4-one Chemical compound C1=C(F)C=C2C(O)=CC=NC2=C1 BYZXOYSEYWCLOK-UHFFFAOYSA-N 0.000 description 1
- SWRUDEPXAHDPSB-UHFFFAOYSA-N 7-bromo-1-methyl-3-(methylsulfanylmethyl)quinolin-4-one Chemical compound BrC1=CC=C2C(=O)C(CSC)=CN(C)C2=C1 SWRUDEPXAHDPSB-UHFFFAOYSA-N 0.000 description 1
- HWBKEPPLGRKDEJ-UHFFFAOYSA-N 7-bromo-3-(chloromethyl)-1-methylquinolin-4-one;hydrochloride Chemical compound Cl.C1=C(Br)C=C2N(C)C=C(CCl)C(=O)C2=C1 HWBKEPPLGRKDEJ-UHFFFAOYSA-N 0.000 description 1
- AXZHIJAIXQIFBT-UHFFFAOYSA-N 7-chloro-3-(hydroxymethyl)-1-methylquinolin-4-one Chemical compound C1=C(Cl)C=C2N(C)C=C(CO)C(=O)C2=C1 AXZHIJAIXQIFBT-UHFFFAOYSA-N 0.000 description 1
- CKYFKKNREGWYNK-UHFFFAOYSA-N 7-chloro-3-(hydroxymethyl)-1h-quinolin-4-one Chemical compound ClC1=CC=C2C(=O)C(CO)=CNC2=C1 CKYFKKNREGWYNK-UHFFFAOYSA-N 0.000 description 1
- UEHFYZFYRVJPGC-UHFFFAOYSA-N 7-ethyl-1-methyl-3-(methylsulfinylmethyl)quinolin-4-one Chemical compound CN1C=C(CS(C)=O)C(=O)C=2C1=CC(CC)=CC=2 UEHFYZFYRVJPGC-UHFFFAOYSA-N 0.000 description 1
- ZLHGUGJJHJJVHV-UHFFFAOYSA-N 7-fluoro-1h-quinolin-4-one Chemical compound N1C=CC(=O)C=2C1=CC(F)=CC=2 ZLHGUGJJHJJVHV-UHFFFAOYSA-N 0.000 description 1
- JPVTWKDGBWUNBQ-UHFFFAOYSA-N 7-methyl-1h-quinolin-4-one Chemical compound OC1=CC=NC2=CC(C)=CC=C21 JPVTWKDGBWUNBQ-UHFFFAOYSA-N 0.000 description 1
- WVNSTZVKWMJVQP-UHFFFAOYSA-N 7-methyl-3-(methylsulfonylmethyl)-1h-quinolin-4-one Chemical compound OC1=C(CS(C)(=O)=O)C=NC2=CC(C)=CC=C21 WVNSTZVKWMJVQP-UHFFFAOYSA-N 0.000 description 1
- OZWYAZRZQKOSSC-UHFFFAOYSA-N 7-tert-butyl-1-methyl-3-(methylsulfinylmethyl)quinolin-4-one Chemical compound C1=C(C(C)(C)C)C=C2N(C)C=C(CS(C)=O)C(=O)C2=C1 OZWYAZRZQKOSSC-UHFFFAOYSA-N 0.000 description 1
- JLURTSQKQXRWHK-UHFFFAOYSA-N 8-chloro-1-methyl-3-(methylsulfonylmethyl)quinolin-4-one Chemical compound C1=CC(Cl)=C2N(C)C=C(CS(C)(=O)=O)C(=O)C2=C1 JLURTSQKQXRWHK-UHFFFAOYSA-N 0.000 description 1
- SUZPLFOSYVTCLE-UHFFFAOYSA-N 8-chloro-1h-quinolin-4-one Chemical compound N1C=CC(=O)C2=C1C(Cl)=CC=C2 SUZPLFOSYVTCLE-UHFFFAOYSA-N 0.000 description 1
- HTELWJVKZKSAQI-UHFFFAOYSA-N 8-fluoro-1h-quinolin-4-one Chemical compound N1C=CC(=O)C2=C1C(F)=CC=C2 HTELWJVKZKSAQI-UHFFFAOYSA-N 0.000 description 1
- PDEPFXZZWHVRDX-UHFFFAOYSA-N 8-fluoro-3-(hydroxymethyl)-1h-quinolin-4-one Chemical compound FC1=CC=CC2=C(O)C(CO)=CN=C21 PDEPFXZZWHVRDX-UHFFFAOYSA-N 0.000 description 1
- DJVLMLGPDKKYJW-UHFFFAOYSA-N 8-methoxy-1h-quinolin-4-one Chemical compound N1C=CC(=O)C2=C1C(OC)=CC=C2 DJVLMLGPDKKYJW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 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
- 244000309466 calf Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- YBEOYBKKSWUSBR-UHFFFAOYSA-N ethyl 4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1 YBEOYBKKSWUSBR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-M methanethiolate Chemical compound [S-]C LSDPWZHWYPCBBB-UHFFFAOYSA-M 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HREHOXSRYOZKNT-UHFFFAOYSA-N quinolin-2-ylmethanol Chemical compound C1=CC=CC2=NC(CO)=CC=C21 HREHOXSRYOZKNT-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8031106 | 1980-09-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
BE890477A true BE890477A (fr) | 1982-03-24 |
Family
ID=10516302
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BE0/206048A BE890477A (fr) | 1980-09-26 | 1981-09-24 | Quinolones, leurs procedes de preparation et composition therapeutique les contenant |
Country Status (4)
Country | Link |
---|---|
JP (1) | JPS5785369A (enrdf_load_stackoverflow) |
BE (1) | BE890477A (enrdf_load_stackoverflow) |
HU (1) | HU184968B (enrdf_load_stackoverflow) |
ZA (1) | ZA816352B (enrdf_load_stackoverflow) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03196382A (ja) * | 1989-12-26 | 1991-08-27 | Nec Home Electron Ltd | 携帯型情報処理装置 |
-
1981
- 1981-09-14 ZA ZA816352A patent/ZA816352B/xx unknown
- 1981-09-24 BE BE0/206048A patent/BE890477A/fr not_active IP Right Cessation
- 1981-09-25 HU HU812775A patent/HU184968B/hu unknown
- 1981-09-25 JP JP56151895A patent/JPS5785369A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6348268B2 (enrdf_load_stackoverflow) | 1988-09-28 |
JPS5785369A (en) | 1982-05-28 |
ZA816352B (en) | 1982-09-29 |
HU184968B (en) | 1984-11-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0283390B1 (fr) | Dérivés du thiazole actifs sur le système cholinergique, procédé d'obtention et compositions pharmaceutiques en contenant | |
EP0399856B1 (fr) | Pteridin-4 (3H)-ones, procédés de préparation et médicaments les contenant | |
LU86406A1 (fr) | Imidazoquinoleines antithrombogenes cardiotoniques | |
EP0535081A1 (en) | Substituted benzimidazoles, process for their preparation and their pharmaceutical use | |
EP0389370A1 (fr) | Nouveaux stéroides 19-Nor 3-céto comportant une chaîne en 17 aminosubstituée, leur procédé de préparation et les intermédiaires de ce procédé,leur application comme médicaments et les compositions pharmaceutiques les contenant | |
EP0611766A1 (fr) | Dérivés de 2-amido-thiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament | |
EP0217700A1 (fr) | Derives de benzimidazole, leur preparation et leur application en therapeutique | |
EP0624575A1 (fr) | Indoles substitués et les compositions pharmaceutiques qui les contiennent | |
EP0205362B1 (fr) | Dérivés quinolylglycinamides, leur procédé de préparation et leur application thérapeutique en tant que psychotropes | |
EP0162776B1 (fr) | Dérivés hétérocycliques, leurs procédés de préparation,médicaments les contenant, utiles notamment comme inhibiteurs de l'aldose réductase | |
EP0117771B1 (fr) | Imino-2 pyrrolidines, leur procédé de préparation et leurs applications en thérapeutique | |
EP0136198B1 (fr) | Dérivés de triazolo pyrimidine, leur procédé de préparation et leur application thérapeutique en tant que toni-cardiaques | |
CH650254A5 (fr) | Quinolones, leurs procedes de preparation et compositions therapeutiques les contenant. | |
EP0172058B1 (fr) | Nouvelles phényl-naphthyridines, leur procédé de préparation, médicaments les contenant, notamment anti-ulcères | |
EP0591027A1 (fr) | Dérivés de pipéridine, leur préparation et leur application en thérapeutique | |
EP0017578B1 (fr) | Acides 5-(2-hydroxy-3-thiopropoxy)chromone-2-carboxyliques, leurs sels et esters, procédé de préparation et médicaments | |
EP0062580B1 (fr) | Dérivés de l'imidazo(1,2-a)quinoléines | |
BE779775A (fr) | Derives de l'uree, procede pour les preparer et leurs applications | |
BE890477A (fr) | Quinolones, leurs procedes de preparation et composition therapeutique les contenant | |
EP0196943B1 (fr) | Nouveaux dérivés 8-thiotétrahydroquinoléines et leurs sels | |
JP2794640B2 (ja) | イミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤 | |
FR2514003A1 (fr) | Nouvelles xanthines a activite pharmacologique, leur procede d'obtention, les compositions pharmaceutiques qui les contiennent et leur utilisation en medecine humaine | |
EP0362006A1 (fr) | Dérivés de quinoléine, leurs procédés de préparation et les médicaments les contenant | |
JPH02275846A (ja) | カルボン酸誘導体 | |
EP0663903B1 (fr) | Derives de dihydro-1,2 oxo-2 amino-3 quinoxalines, leur preparation et leur application en therapeutique |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RE | Patent lapsed |
Owner name: THE BOOTS CY PLC Effective date: 19910930 |