CS195689B2 - Method of producing novel derivatives of nitroimidazole - Google Patents

Method of producing novel derivatives of nitroimidazole Download PDF

Info

Publication number: CS195689B2
Authority: CS; Czechoslovakia
Prior art keywords: group; methyl; formula; treated; alkyl
Prior art date: 1973-09-24

Application number

CS746554A

Other languages

Czech (cs)

English (en)

Inventor

Kuppuswamy Nagarajan

Vishwa P Arya

Thomas George

Original Assignee

Ciba Geigy Ag

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.)

1973-09-24

Filing date

1974-09-24

Publication date

1980-02-29

1974-09-24 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1977-07-14 Priority to CS774703A priority Critical patent/CS195690B2/cs

1977-07-14 Priority to CS774704A priority patent/CS195691B2/cs

1980-02-29 Publication of CS195689B2 publication Critical patent/CS195689B2/cs

Links

238000000034 method Methods 0.000 title claims description 26
150000004957 nitroimidazoles Chemical class 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 25
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 74
150000001875 compounds Chemical class 0.000 claims description 50
-1 imidazole compound Chemical class 0.000 claims description 41
229910052757 nitrogen Inorganic materials 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 21
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
RSOPCRYPVDDVAX-UHFFFAOYSA-N 1-methyl-2-methylsulfonyl-5-nitroimidazole Chemical compound CN1C([N+]([O-])=O)=CN=C1S(C)(=O)=O RSOPCRYPVDDVAX-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001207 fluorophenyl group Chemical group 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
GBDVZLHCKQDABB-UHFFFAOYSA-N 1-methyl-4-methylsulfonyl-5-nitroimidazole Chemical compound CN1C=NC(S(C)(=O)=O)=C1[N+]([O-])=O GBDVZLHCKQDABB-UHFFFAOYSA-N 0.000 claims 1
UIQNTKKFJXHGIL-UHFFFAOYSA-N 2-methylsulfonyl-5-nitro-1h-imidazole Chemical compound CS(=O)(=O)C1=NC=C([N+]([O-])=O)N1 UIQNTKKFJXHGIL-UHFFFAOYSA-N 0.000 claims 1
150000003973 alkyl amines Chemical class 0.000 claims 1
150000001351 alkyl iodides Chemical class 0.000 claims 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
LRDXJLPHTXEZMI-UHFFFAOYSA-N n,n-dimethyl-2-oxoimidazolidine-1-carboxamide Chemical compound CN(C)C(=O)N1CCNC1=O LRDXJLPHTXEZMI-UHFFFAOYSA-N 0.000 claims 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
241000894006 Bacteria Species 0.000 abstract description 11
230000000845 anti-microbial effect Effects 0.000 abstract description 3
241000224483 Coccidia Species 0.000 abstract description 2
241000242678 Schistosoma Species 0.000 abstract description 2
239000004599 antimicrobial Substances 0.000 abstract description 2
230000015556 catabolic process Effects 0.000 abstract description 2
238000006731 degradation reaction Methods 0.000 abstract description 2
229910052717 sulfur Inorganic materials 0.000 abstract description 2
230000001225 therapeutic effect Effects 0.000 abstract description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
125000002947 alkylene group Chemical group 0.000 abstract 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
150000001204 N-oxides Chemical class 0.000 abstract 1
241001502500 Trichomonadida Species 0.000 abstract 1
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000004103 aminoalkyl group Chemical group 0.000 abstract 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
235000019730 animal feed additive Nutrition 0.000 abstract 1
239000000921 anthelmintic agent Substances 0.000 abstract 1
229940124339 anthelmintic agent Drugs 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
230000000813 microbial effect Effects 0.000 abstract 1
XMWZWFFVDSIGJD-UHFFFAOYSA-N n-methyl-3-(1-methyl-5-nitroimidazol-2-yl)-2-oxoimidazolidine-1-carbothioamide Chemical compound O=C1N(C(=S)NC)CCN1C1=NC=C([N+]([O-])=O)N1C XMWZWFFVDSIGJD-UHFFFAOYSA-N 0.000 abstract 1
239000011368 organic material Substances 0.000 abstract 1
125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 63
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
239000011541 reaction mixture Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
239000007858 starting material Substances 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000725 suspension Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
239000000155 melt Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 17
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 16
239000012312 sodium hydride Substances 0.000 description 16
229910000104 sodium hydride Inorganic materials 0.000 description 16
238000003756 stirring Methods 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 13
239000002480 mineral oil Substances 0.000 description 13
235000010446 mineral oil Nutrition 0.000 description 13
238000001953 recrystallisation Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000004480 active ingredient Substances 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
238000001816 cooling Methods 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
239000000284 extract Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000002585 base Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
229920000159 gelatin Polymers 0.000 description 6
235000019322 gelatine Nutrition 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
239000008298 dragée Substances 0.000 description 5
239000008273 gelatin Substances 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
235000011187 glycerol Nutrition 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
229920001592 potato starch Polymers 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000008707 rearrangement Effects 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003826 tablet Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000699800 Cricetinae Species 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
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 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
238000004659 sterilization and disinfection Methods 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
WTCUHYRXLIHSLY-UHFFFAOYSA-N 1-methylsulfonylimidazolidin-2-one Chemical compound CS(=O)(=O)N1CCNC1=O WTCUHYRXLIHSLY-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000008119 colloidal silica Substances 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000036074 healthy skin Effects 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
150000002460 imidazoles Chemical class 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
OWWASHBXVFOTDF-UHFFFAOYSA-N n-methyl-1h-imidazole-2-carboxamide Chemical compound CNC(=O)C1=NC=CN1 OWWASHBXVFOTDF-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000003883 ointment base Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
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239000010959 steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229960000654 sulfafurazole Drugs 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000012855 volatile organic compound Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CS746554A 1973-09-24 1974-09-24 Method of producing novel derivatives of nitroimidazole CS195689B2 (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CS774703A CS195690B2 (cs)	1973-09-24	1977-07-14	Způsob výroby nových derivátů nitroimidazolu
CS774704A CS195691B2 (en)	1973-09-24	1977-07-14	Method of producing novel derivatives of nitroimidazole

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1366773A CH592653A5 (fr)	1973-09-24	1973-09-24

Publications (1)

Publication Number	Publication Date
CS195689B2 true CS195689B2 (en)	1980-02-29

Family

ID=4394325

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS746554A CS195689B2 (en)	1973-09-24	1974-09-24	Method of producing novel derivatives of nitroimidazole

Country Status (26)

Country	Link
JP (1)	JPS5910347B2 (fr)
AR (2)	AR212578A1 (fr)
AT (1)	AT337692B (fr)
BE (1)	BE820206A (fr)
BG (2)	BG22813A3 (fr)
CH (1)	CH592653A5 (fr)
CS (1)	CS195689B2 (fr)
DD (1)	DD114814A5 (fr)
DE (1)	DE2444070A1 (fr)
DK (1)	DK447474A (fr)
DO (1)	DOP1981002973A (fr)
ES (1)	ES430352A1 (fr)
FI (1)	FI62293C (fr)
FR (1)	FR2244498A1 (fr)
HU (1)	HU171562B (fr)
IE (1)	IE40003B1 (fr)
IL (1)	IL45536A (fr)
NL (1)	NL7412482A (fr)
NO (1)	NO141895C (fr)
OA (1)	OA04828A (fr)
PH (1)	PH13743A (fr)
PL (3)	PL95691B1 (fr)
RO (1)	RO70190A (fr)
SE (1)	SE416300B (fr)
SU (3)	SU542473A3 (fr)
YU (3)	YU37337B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5956254U (ja) *	1982-10-05	1984-04-12	住友金属鉱山株式会社	擁壁ブロツク
DE4426757A1 (de) *	1994-07-28	1996-02-01	Bayer Ag	2-Imidazolidinon-Derivate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2944061A (en) *	1957-09-20	1960-07-05		Acyl derivatives and process
IL39283A (en) *	1971-05-03	1976-01-30	Ciba Geigy Ag	Substituted 2-oxo or thioxo-3-(5-nitro-imidazol-2-yl)-tetrahydroimidazoles and their manufacture
BE795068A (fr) *	1972-02-08	1973-08-07	Ciba Geigy	Nouveaux 4- ou 5-nitro-inmidazoles et procedes pour leur preparation

1973
- 1973-09-24 CH CH1366773A patent/CH592653A5/xx not_active IP Right Cessation
1974
- 1974-08-21 DK DK447474A patent/DK447474A/da not_active Application Discontinuation
- 1974-08-22 IE IE1746/74A patent/IE40003B1/xx unknown
- 1974-08-26 IL IL45536A patent/IL45536A/xx unknown
- 1974-09-06 SE SE7411296A patent/SE416300B/xx not_active IP Right Cessation
- 1974-09-12 FI FI2669/74A patent/FI62293C/fi active
- 1974-09-14 DE DE2444070A patent/DE2444070A1/de not_active Ceased
- 1974-09-18 FR FR7431471A patent/FR2244498A1/fr active Granted
- 1974-09-20 NO NO743395A patent/NO141895C/no unknown
- 1974-09-20 NL NL7412482A patent/NL7412482A/xx not_active Application Discontinuation
- 1974-09-21 OA OA55302A patent/OA04828A/fr unknown
- 1974-09-23 YU YU2559/74A patent/YU37337B/xx unknown
- 1974-09-23 PL PL1974185103A patent/PL95691B1/pl unknown
- 1974-09-23 PL PL1974174285A patent/PL96510B1/pl unknown
- 1974-09-23 BG BG029300A patent/BG22813A3/xx unknown
- 1974-09-23 SU SU2063056A patent/SU542473A3/ru active
- 1974-09-23 PL PL1974185100A patent/PL95689B1/pl unknown
- 1974-09-23 PH PH16324A patent/PH13743A/en unknown
- 1974-09-23 RO RO7487513A patent/RO70190A/fr unknown
- 1974-09-23 AR AR255685A patent/AR212578A1/es active
- 1974-09-23 BE BE148776A patent/BE820206A/fr not_active IP Right Cessation
- 1974-09-23 BG BG027754A patent/BG22823A3/xx unknown
- 1974-09-23 DD DD181273A patent/DD114814A5/xx unknown
- 1974-09-23 AT AT762174A patent/AT337692B/de not_active IP Right Cessation
- 1974-09-24 ES ES430352A patent/ES430352A1/es not_active Expired
- 1974-09-24 CS CS746554A patent/CS195689B2/cs unknown
- 1974-09-24 JP JP49110385A patent/JPS5910347B2/ja not_active Expired
- 1974-09-24 HU HU74CI00001509A patent/HU171562B/hu unknown
1975
- 1975-01-01 AR AR258970A patent/AR207980A1/es active
- 1975-07-02 SU SU7502149413A patent/SU564812A3/ru active
- 1975-07-02 SU SU7502149414A patent/SU571191A3/ru active
1980
- 1980-11-24 YU YU2982/80A patent/YU37338B/xx unknown
- 1980-11-24 YU YU2983/80A patent/YU37339B/xx unknown
1981
- 1981-02-09 DO DO1981002973A patent/DOP1981002973A/es unknown

Also Published As

Publication number	Publication date
SE416300B (sv)	1980-12-15
BE820206A (fr)	1975-03-24
YU37338B (en)	1984-08-31
FI62293C (fi)	1982-12-10
NL7412482A (nl)	1975-03-26
JPS5058071A (fr)	1975-05-20
BG22813A3 (bg)	1977-04-20
FI266974A7 (fr)	1975-03-25
BG22823A3 (bg)	1977-04-20
AR212578A1 (es)	1978-08-15
SE7411296L (fr)	1975-03-25
NO141895C (no)	1980-06-04
JPS5910347B2 (ja)	1984-03-08
ATA762174A (de)	1976-11-15
AR207980A1 (es)	1976-11-22
YU255974A (en)	1983-04-27
SU571191A3 (ru)	1977-08-30
YU298280A (en)	1983-04-27
RO70190A (fr)	1982-09-09
SU542473A3 (ru)	1977-01-05
FR2244498A1 (en)	1975-04-18
PL96510B1 (pl)	1977-12-31
PL95689B1 (pl)	1977-11-30
NO141895B (no)	1980-02-18
DD114814A5 (fr)	1975-08-20
SU564812A3 (ru)	1977-07-05
DK447474A (fr)	1975-05-20
PL95691B1 (pl)	1977-11-30
DE2444070A1 (de)	1975-03-27
IL45536A0 (en)	1974-11-29
CH592653A5 (fr)	1977-10-31
HU171562B (hu)	1978-02-28
IE40003B1 (en)	1979-02-14
YU37339B (en)	1984-08-31
OA04828A (fr)	1980-10-31
DOP1981002973A (es)	1986-06-02
FR2244498B1 (fr)	1978-07-21
NO743395L (fr)	1975-04-21
YU37337B (en)	1984-08-31
IE40003L (en)	1975-03-24
PH13743A (en)	1980-09-17
YU298380A (en)	1983-04-27
AT337692B (de)	1977-07-11
FI62293B (fi)	1982-08-31
ES430352A1 (es)	1976-09-16
IL45536A (en)	1978-10-31

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