NO760113L - - Google Patents

Info

Publication number: NO760113L
Authority: NO; Norway
Prior art keywords: methyl; compound; approx; formula; nitroimidazole
Prior art date: 1975-01-15

Application number

NO760113A

Other languages

English (en)

Norwegian (no)

Inventor

A Assandri

G Lancini

G Volpe

B Cavalleri

Original Assignee

Lepetit Spa

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.)

1975-01-15

Filing date

1976-01-14

Publication date

1976-07-16

1976-01-14 Application filed by Lepetit Spa filed Critical Lepetit Spa

1976-07-16 Publication of NO760113L publication Critical patent/NO760113L/no

Links

150000001875 compounds Chemical class 0.000 claims description 73
239000000203 mixture Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
241000224527 Trichomonas vaginalis Species 0.000 claims description 9
-1 alkali metal cyanide Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
208000015181 infectious disease Diseases 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
HSCUZOQCNBPBST-UHFFFAOYSA-N 2-methoxy-2-methylpropanal Chemical compound COC(C)(C)C=O HSCUZOQCNBPBST-UHFFFAOYSA-N 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
231100001274 therapeutic index Toxicity 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
229940126062 Compound A Drugs 0.000 description 11
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 11
239000000243 solution Substances 0.000 description 10
150000004959 2-nitroimidazoles Chemical class 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000001727 in vivo Methods 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 8
238000003756 stirring Methods 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000003716 antitrichomonal agent Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000007787 solid Substances 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
NOXMCEHYBLYCTK-UHFFFAOYSA-N 1-methyl-2-nitro-5-propan-2-ylimidazole Chemical compound CC(C)C1=CN=C([N+]([O-])=O)N1C NOXMCEHYBLYCTK-UHFFFAOYSA-N 0.000 description 2
DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 2
PCSDFERLFRFTOA-UHFFFAOYSA-N 3-methoxy-3-methyl-2-(methylamino)butanenitrile Chemical compound CNC(C#N)C(C)(C)OC PCSDFERLFRFTOA-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
150000002460 imidazoles Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
WXSSUDRHAJTESR-UHFFFAOYSA-N (3-methyl-2-nitroimidazol-4-yl)methanol Chemical compound CN1C(CO)=CN=C1[N+]([O-])=O WXSSUDRHAJTESR-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
KAQBNBSMMVTKRN-UHFFFAOYSA-N 2,4,6-trinitrobenzoic acid Chemical compound OC(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KAQBNBSMMVTKRN-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
239000005995 Aluminium silicate Substances 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
238000012404 In vitro experiment Methods 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
241000699670 Mus sp. Species 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
241000224526 Trichomonas Species 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 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
239000013543 active substance Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000005422 blasting Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000003906 humectant Substances 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000007803 itching Effects 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
IXHMHWIBCIYOAZ-UHFFFAOYSA-N styphnic acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1[N+]([O-])=O IXHMHWIBCIYOAZ-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 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 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
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 1
210000001215 vagina Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
- 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

Landscapes

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

NO760113A 1975-01-15 1976-01-14 NO760113L (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1684/75A GB1480192A (en)	1975-01-15	1975-01-15	1-methyl-2-nitro-imidazole-5-methanol derivatives

Publications (1)

Publication Number	Publication Date
NO760113L true NO760113L (xx)	1976-07-16

Family

ID=9726232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO760113A NO760113L (xx)	1975-01-15	1976-01-14

Country Status (29)

Country	Link
US (1)	US4041168A (xx)
JP (1)	JPS5195069A (xx)
AR (1)	AR207804A1 (xx)
AT (1)	ATA13576A (xx)
AU (1)	AU8787575A (xx)
BE (1)	BE837595A (xx)
CA (1)	CA1062716A (xx)
CH (1)	CH609050A5 (xx)
DD (1)	DD123744A5 (xx)
DE (1)	DE2600538C3 (xx)
DK (1)	DK153839C (xx)
ES (1)	ES444324A1 (xx)
FI (1)	FI753726A (xx)
FR (1)	FR2297623A1 (xx)
GB (1)	GB1480192A (xx)
GR (1)	GR59991B (xx)
IE (1)	IE42462B1 (xx)
IL (1)	IL48751A0 (xx)
IN (1)	IN141389B (xx)
LU (1)	LU74172A1 (xx)
NL (1)	NL175413C (xx)
NO (1)	NO760113L (xx)
NZ (1)	NZ179762A (xx)
PL (1)	PL98602B1 (xx)
PT (1)	PT64695B (xx)
RO (1)	RO69138A (xx)
SE (1)	SE422204B (xx)
SU (1)	SU576043A3 (xx)
ZA (1)	ZA758017B (xx)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4395341A (en) *	1977-07-21	1983-07-26	G. D. Searle & Co.	Use of metronidazole in oil recovery
DE3070778D1 (en) *	1979-08-11	1985-07-25	Bayer Ag	Antimycotic agents with enhanced release of the active ingredients
US4957918A (en) *	1988-06-09	1990-09-18	Leonard Bloom	Topical treatment of blepharitis

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3065133A (en) *	1956-09-28	1962-11-20	Rhone Poulenc Sa	Imidazoles for the control of histomoniasis
DE1470102A1 (de) *	1963-11-27	1969-05-29	Merck & Co Inc	2-Hydroxymethyl-5-nitroimidazole und Verfahren zu deren Herstellung
US3472864A (en) *	1964-03-18	1969-10-14	Merck & Co Inc	2-carbonyl-5-nitroimidazoles
NL124627C (xx) *	1964-08-12
GB1051388A (xx) *	1964-11-17
US3584007A (en) *	1968-09-16	1971-06-08	Merck & Co Inc	Preparation of 1-substituted-2-hydroxymethyl - 5-nitroimidazoles employing chilorinated benzenes as the reaction medium
NL143227B (nl) *	1968-11-15	1974-09-16	Lepetit Spa	Werkwijze ter bereiding van imidazoolderivaten met bactericide werking.
US3652579A (en) *	1969-06-26	1972-03-28	Hoffmann La Roche	1-methyl-2-substituted 5-nitroimidazoles
US3634446A (en) *	1969-10-06	1972-01-11	Hoffmann La Roche	1-methyl-2-isopropyl-5-nitroimidazole and water soluble salts thereof
DE2229223C3 (de) *	1971-07-30	1975-12-18	Gruppo Lepetit S.P.A., Mailand (Italien)	2-Nitro-S-imidazol-Derivate und Verfahren zu deren Herstellung
US3828064A (en) *	1972-10-25	1974-08-06	Dow Chemical Co	Method of preparing 1,5-disubstituted-2-nitroimidazoles

1975
- 1975-01-15 GB GB1684/75A patent/GB1480192A/en not_active Expired
- 1975-12-20 GR GR49653A patent/GR59991B/el unknown
- 1975-12-24 AU AU87875/75A patent/AU8787575A/en not_active Expired
- 1975-12-29 ZA ZA00758017A patent/ZA758017B/xx unknown
- 1975-12-29 IL IL48751A patent/IL48751A0/xx unknown
- 1975-12-29 US US05/644,382 patent/US4041168A/en not_active Expired - Lifetime
- 1975-12-31 FI FI753726A patent/FI753726A/fi not_active Application Discontinuation
- 1975-12-31 IN IN2428/CAL/75A patent/IN141389B/en unknown
1976
- 1976-01-01 AR AR261930A patent/AR207804A1/es active
- 1976-01-08 IE IE30/76A patent/IE42462B1/en unknown
- 1976-01-08 DE DE2600538A patent/DE2600538C3/de not_active Expired
- 1976-01-12 AT AT13576A patent/ATA13576A/de not_active IP Right Cessation
- 1976-01-13 LU LU74172A patent/LU74172A1/xx unknown
- 1976-01-13 RO RO7684482A patent/RO69138A/ro unknown
- 1976-01-13 NL NLAANVRAGE7600284,A patent/NL175413C/xx not_active IP Right Cessation
- 1976-01-14 DK DK012976A patent/DK153839C/da not_active IP Right Cessation
- 1976-01-14 SE SE7600341A patent/SE422204B/xx not_active IP Right Cessation
- 1976-01-14 PT PT64695A patent/PT64695B/pt unknown
- 1976-01-14 NZ NZ179762A patent/NZ179762A/xx unknown
- 1976-01-14 SU SU7602306604A patent/SU576043A3/ru active
- 1976-01-14 NO NO760113A patent/NO760113L/no unknown
- 1976-01-14 DD DD190802A patent/DD123744A5/xx unknown
- 1976-01-14 CA CA243,508A patent/CA1062716A/en not_active Expired
- 1976-01-14 CH CH42376A patent/CH609050A5/xx not_active IP Right Cessation
- 1976-01-15 ES ES444324A patent/ES444324A1/es not_active Expired
- 1976-01-15 FR FR7600995A patent/FR2297623A1/fr active Granted
- 1976-01-15 PL PL1976186558A patent/PL98602B1/pl unknown
- 1976-01-15 BE BE163537A patent/BE837595A/xx not_active IP Right Cessation
- 1976-01-16 JP JP51003956A patent/JPS5195069A/ja active Granted

Also Published As

Publication number	Publication date
SE7600341L (sv)	1976-07-16
NL175413B (nl)	1984-06-01
SU576043A3 (ru)	1977-10-05
PL98602B1 (pl)	1978-05-31
DK153839B (da)	1988-09-12
BE837595A (fr)	1976-07-15
RO69138A (ro)	1982-03-24
AU8787575A (en)	1977-06-30
PT64695A (fr)	1976-02-01
IE42462B1 (en)	1980-08-13
SE422204B (sv)	1982-02-22
IE42462L (en)	1976-07-15
CA1062716A (en)	1979-09-18
DK153839C (da)	1989-04-10
NZ179762A (en)	1978-06-02
AR207804A1 (es)	1976-10-29
NL7600284A (nl)	1976-07-19
LU74172A1 (xx)	1976-07-20
CH609050A5 (xx)	1979-02-15
ES444324A1 (es)	1977-05-01
JPS5195069A (en)	1976-08-20
ZA758017B (en)	1976-12-29
NL175413C (nl)	1984-11-01
FI753726A (xx)	1976-07-16
PT64695B (fr)	1977-08-10
IN141389B (xx)	1977-02-19
FR2297623A1 (fr)	1976-08-13
JPS5729033B2 (xx)	1982-06-19
DK12976A (da)	1976-07-16
ATA13576A (de)	1978-07-15
US4041168A (en)	1977-08-09
GR59991B (en)	1978-03-28
DE2600538A1 (de)	1976-07-22
GB1480192A (en)	1977-07-20
DE2600538C3 (de)	1979-01-18
DE2600538B2 (de)	1978-05-24
IL48751A0 (en)	1976-02-29
FR2297623B1 (xx)	1979-06-22
DD123744A5 (xx)	1977-01-12

Publication	Publication Date	Title
EP0138464B1 (en)	1989-11-15	2-amino-5-hydroxy-4-methylpyrimidine derivatives
US4207324A (en)	1980-06-10	1,2-Di-Substituted-4-haloimidazole-5-acetic acid derivatives and their use
CA1178584A (en)	1984-11-27	3,4-dihydro-5h-2,3-benzodiazepine derivatives and a process for the preparation thereof
NO164476B (no)	1990-07-02	Analogifremgangsmaate ved fremstilling av terapeutisk virksomme 1,2,3,5-tetrahydroimidazo-(2,1-b)-kinazoliner.
JPH0216315B2 (xx)	1990-04-16
EP0104522A2 (en)	1984-04-04	New pyrazolo(3,4-b)pyridine derivatives and process for producing them
WO1996020936A1 (en)	1996-07-11	Novel thiazolidin-4-one derivatives
US4366166A (en)	1982-12-28	Filaricidal 2-nitroimidazole compounds
NO151893B (no)	1985-03-18	Analogifremgangsmaate for fremstilling av terapeutisk virksomme 3h-nafto(1,2-d)imidazolderivater
US4327101A (en)	1982-04-27	Quinoline compound useful as antibacterial agents in warm-blooded animals
GB2092144A (en)	1982-08-11	Novel indanyl derivaitves
KR0152299B1 (ko)	1998-10-15	시클로헵트이미다졸 유도체, 그의 제조방법 및 이 화합물을 함유하는 치료제
DK166584B1 (da)	1993-06-14	Substituerede 4-benzyl-1h-imidazoler, fremgangsmaade til deres fremstilling samt farmaceutiske praeparater indeholdende dem
NO760113L (xx)	1976-07-16
EP0250264A1 (en)	1987-12-23	Irreversible dopamine-Beta-hydroxylase inhibitors
US4673677A (en)	1987-06-16	Method for treatment of gastrointestinal disorders
NO179513B (no)	1996-07-15	2-substituerte kinolylmetoksy-fenyleddiksyrederivater, legemidler inneholdende dem samt deres anvendelse for fremstilling av legemidler
DE2424671A1 (de)	1974-12-12	Triazoloisochinolinderivate und verfahren zu deren herstellung
IE41563B1 (en)	1980-01-30	Sulfonamides
US4293695A (en)	1981-10-06	Furonaphthyridine compounds
EP0168181B1 (en)	1990-08-29	Cyclic amides
US3153050A (en)	1964-10-13	Spiro
NO313413B1 (no)	2002-09-30	Hydrokinonderivat, anvendelse derav og farmasöytisk preparat
US4123537A (en)	1978-10-31	2-Halo-4-aminomethyl-6-alkyl-3-pyridinols useful as diuretics in treating hypertension and edema
US3812135A (en)	1974-05-21	Pyrroloindole and pyridoindole derivatives