SU1287745A3 - Способ получени производных хинолонов - Google Patents
Способ получени производных хинолонов Download PDFInfo
- Publication number
- SU1287745A3 SU1287745A3 SU813336186A SU3336186A SU1287745A3 SU 1287745 A3 SU1287745 A3 SU 1287745A3 SU 813336186 A SU813336186 A SU 813336186A SU 3336186 A SU3336186 A SU 3336186A SU 1287745 A3 SU1287745 A3 SU 1287745A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- methyl
- fluoro
- chloro
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 150000007660 quinolones Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- -1 alkali metal methanesulfinate Chemical class 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000005711 Benzoic acid Substances 0.000 claims abstract 2
- 235000010233 benzoic acid Nutrition 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 230000003647 oxidation Effects 0.000 claims abstract 2
- 238000007254 oxidation reaction Methods 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 238000007664 blowing Methods 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- OZNTVIXYGTUPJY-UHFFFAOYSA-N 1,2-dimethoxy-4-methyl-5-methylsulfinylbenzene Chemical compound COC1=CC(C)=C(S(C)=O)C=C1OC OZNTVIXYGTUPJY-UHFFFAOYSA-N 0.000 abstract description 7
- 229950004790 tolmesoxide Drugs 0.000 abstract description 7
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-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 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 230000036772 blood pressure Effects 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- HDPVRRZTNQXTJR-UHFFFAOYSA-N 7-chloro-1-methyl-3-(methylsulfanylmethyl)quinolin-4-one Chemical compound ClC1=CC=C2C(=O)C(CSC)=CN(C)C2=C1 HDPVRRZTNQXTJR-UHFFFAOYSA-N 0.000 description 2
- DBTIAXSTNJXFCH-UHFFFAOYSA-N 7-fluoro-3-(hydroxymethyl)-1h-quinolin-4-one Chemical compound C1=C(F)C=CC2=C(O)C(CO)=CN=C21 DBTIAXSTNJXFCH-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 231100000957 no side effect Toxicity 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000010349 pulsation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WVYJGVFNHPBIMT-UHFFFAOYSA-N (1-methyl-4-oxoquinolin-3-yl)methyl acetate Chemical compound C1=CC=C2C(=O)C(COC(=O)C)=CN(C)C2=C1 WVYJGVFNHPBIMT-UHFFFAOYSA-N 0.000 description 1
- AGEVWYPZSUUXCB-UHFFFAOYSA-N 1-methyl-3-(methylsulfinylmethyl)-7-(trifluoromethyl)quinolin-4-one Chemical compound C1=C(C(F)(F)F)C=C2N(C)C=C(CS(C)=O)C(=O)C2=C1 AGEVWYPZSUUXCB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N 1H-quinolin-4-one Natural products C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DJIDIYHFTRCMAZ-UHFFFAOYSA-N 3-(hydroxymethyl)-1-methylquinolin-4-one Chemical compound C1=CC=C2N(C)C=C(CO)C(=O)C2=C1 DJIDIYHFTRCMAZ-UHFFFAOYSA-N 0.000 description 1
- WZWHUBIVAMSGGX-UHFFFAOYSA-N 6-fluoro-3-(hydroxymethyl)-1h-quinolin-4-one Chemical compound C1=CC(F)=CC2=C(O)C(CO)=CN=C21 WZWHUBIVAMSGGX-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
- FYUBNMLTMYNLIH-UHFFFAOYSA-N 7-bromo-1-methyl-3-(methylsulfonylmethyl)quinolin-4-one Chemical compound C1=C(Br)C=C2N(C)C=C(CS(C)(=O)=O)C(=O)C2=C1 FYUBNMLTMYNLIH-UHFFFAOYSA-N 0.000 description 1
- GGCBEWNXEGDQAP-UHFFFAOYSA-N 7-bromo-1h-quinolin-4-one Chemical compound N1C=CC(=O)C=2C1=CC(Br)=CC=2 GGCBEWNXEGDQAP-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
- BDNCOUZITJURJK-UHFFFAOYSA-N 7-bromo-3-(hydroxymethyl)-1-methylquinolin-4-one Chemical compound C1=C(Br)C=C2N(C)C=C(CO)C(=O)C2=C1 BDNCOUZITJURJK-UHFFFAOYSA-N 0.000 description 1
- PTYDCDWEDCVWLI-UHFFFAOYSA-N 7-bromo-3-(hydroxymethyl)-1h-quinolin-4-one Chemical compound C1=C(Br)C=CC2=C(O)C(CO)=CN=C21 PTYDCDWEDCVWLI-UHFFFAOYSA-N 0.000 description 1
- IVQBWEUZCHIAJE-UHFFFAOYSA-N 7-chloro-3-(chloromethyl)-1-methylquinolin-4-one;hydrochloride Chemical compound Cl.C1=C(Cl)C=C2N(C)C=C(CCl)C(=O)C2=C1 IVQBWEUZCHIAJE-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
- KFODGYUZXRZUCQ-UHFFFAOYSA-N 7-fluoro-1-methyl-3-(methylsulfanylmethyl)quinolin-4-one Chemical compound FC1=CC=C2C(=O)C(CSC)=CN(C)C2=C1 KFODGYUZXRZUCQ-UHFFFAOYSA-N 0.000 description 1
- XDTQCQCYYCBTDO-UHFFFAOYSA-N 7-fluoro-1-methyl-3-(methylsulfonylmethyl)quinolin-4-one Chemical compound C1=C(F)C=C2N(C)C=C(CS(C)(=O)=O)C(=O)C2=C1 XDTQCQCYYCBTDO-UHFFFAOYSA-N 0.000 description 1
- FLVIGTDUEORREX-UHFFFAOYSA-N 7-fluoro-3-(hydroxymethyl)-1-methylquinolin-4-one Chemical compound C1=C(F)C=C2N(C)C=C(CO)C(=O)C2=C1 FLVIGTDUEORREX-UHFFFAOYSA-N 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KJAFZRCNIJFECP-UHFFFAOYSA-N benzoic acid chlorobenzene Chemical compound ClC1=CC=CC=C1.C(C1=CC=CC=C1)(=O)O KJAFZRCNIJFECP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 208000018299 prostration Diseases 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8031162 | 1980-09-26 | ||
| GB8031106 | 1980-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1287745A3 true SU1287745A3 (ru) | 1987-01-30 |
Family
ID=26276999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813336186A SU1287745A3 (ru) | 1980-09-26 | 1981-09-25 | Способ получени производных хинолонов |
Country Status (2)
| Country | Link |
|---|---|
| CS (1) | CS228519B2 (cs) |
| SU (1) | SU1287745A3 (cs) |
-
1981
- 1981-09-25 SU SU813336186A patent/SU1287745A3/ru active
- 1981-09-25 CS CS708981A patent/CS228519B2/cs unknown
Non-Patent Citations (1)
| Title |
|---|
| Doxey J.C. Tolmes oxide,А. Drug that lowers blood pressuve by a direct Relaxout effect on vascular sutootu. - Muscle Br J.Pharmac,1978, 63, 111-118. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CS228519B2 (cs) | 1984-05-14 |
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