NO122374B - - Google Patents

Download PDF

Info

Publication number: NO122374B
Authority: NO; Norway
Prior art keywords: compounds; nitroimidazole; approx; compound; general formula
Prior art date: 1964-03-10

Application number

NO165769A

Other languages

English (en)

Norwegian (no)

Inventor

L Sarett

D Hoff

D Henry

Original Assignee

Merck & Co Inc

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.)

1964-03-10

Filing date

1969-04-22

Publication date

1971-06-21

1964-03-10 Priority claimed from US350639A external-priority patent/US3399211A/en

1969-04-22 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1969-04-22 Priority to NO165769A priority Critical patent/NO122374B/no

1971-06-21 Publication of NO122374B publication Critical patent/NO122374B/no

Links

150000001875 compounds Chemical class 0.000 claims description 25
238000000034 method Methods 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 9
239000000243 solution Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
201000010099 disease Diseases 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
241000271566 Aves Species 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000003814 drug Substances 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
244000144977 poultry Species 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
MFFPOGNCQPYWEX-UHFFFAOYSA-N 2-(5-nitro-1H-imidazol-2-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=NC=C([N+]([O-])=O)N1 MFFPOGNCQPYWEX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
241000286209 Phasianidae Species 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
238000001816 cooling Methods 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000003651 drinking water Substances 0.000 description 3
235000020188 drinking water Nutrition 0.000 description 3
229940079593 drug Drugs 0.000 description 3
-1 nitroimidazo-isoindoles Chemical class 0.000 description 3
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 2
YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 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
241000224526 Trichomonas Species 0.000 description 2
208000005448 Trichomonas Infections Diseases 0.000 description 2
241000224527 Trichomonas vaginalis Species 0.000 description 2
206010044620 Trichomoniasis Diseases 0.000 description 2
206010046914 Vaginal infection Diseases 0.000 description 2
SHAXJRGMYFOSSQ-UHFFFAOYSA-N [2-(5-nitro-1H-imidazol-2-yl)phenyl]methanol Chemical compound OCC1=C(C=CC=C1)C=1NC=C(N1)[N+](=O)[O-] SHAXJRGMYFOSSQ-UHFFFAOYSA-N 0.000 description 2
206010000496 acne Diseases 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000001572 anti-trichomonad Effects 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
VDFHYUDENNTZKS-UHFFFAOYSA-N ethyl 2-cyanobenzenecarboximidate;hydrochloride Chemical compound Cl.CCOC(=N)C1=CC=CC=C1C#N VDFHYUDENNTZKS-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 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
208000015181 infectious disease Diseases 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
235000012054 meals Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
VHBHOFCCXQFQCL-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1C1=NC=CN1 VHBHOFCCXQFQCL-UHFFFAOYSA-N 0.000 description 1
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
241000207199 Citrus Species 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
241000948220 Histomonas meleagridis Species 0.000 description 1
240000004658 Medicago sativa Species 0.000 description 1
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
208000027954 Poultry disease Diseases 0.000 description 1
208000010362 Protozoan Infections Diseases 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
201000008100 Vaginitis Diseases 0.000 description 1
239000005862 Whey Substances 0.000 description 1
102000007544 Whey Proteins Human genes 0.000 description 1
108010046377 Whey Proteins Proteins 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000842 anti-protozoal effect Effects 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
235000015155 buttermilk Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000009313 farming Methods 0.000 description 1
235000019688 fish Nutrition 0.000 description 1
244000144992 flock Species 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000004957 nitroimidazoles Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
238000010422 painting Methods 0.000 description 1
230000000590 parasiticidal effect Effects 0.000 description 1
239000002297 parasiticide Substances 0.000 description 1
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
229920006391 phthalonitrile polymer Polymers 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
244000000040 protozoan parasite Species 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000021055 solid food Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
239000005418 vegetable material Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000015099 wheat brans Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO165769A 1964-03-10 1969-04-22 NO122374B (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO165769A NO122374B (fr)	1964-03-10	1969-04-22

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US350639A US3399211A (en)	1964-03-10	1964-03-10	Production of 2-aryl-4(5)-nitroimidazoles
NO157118A NO121445B (fr)	1964-03-10	1965-03-09
US72464968A	1968-02-02	1968-02-02
NO165769A NO122374B (fr)	1964-03-10	1969-04-22
US84374969A	1969-07-22	1969-07-22

Publications (1)

Publication Number	Publication Date
NO122374B true NO122374B (fr)	1971-06-21

Family

ID=27532545

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO165769A NO122374B (fr)	1964-03-10	1969-04-22

Country Status (1)

Country	Link
NO (1)	NO122374B (fr)

1969
- 1969-04-22 NO NO165769A patent/NO122374B/no unknown

Publication	Publication Date	Title
US3461206A (en)	1969-08-12	Compositions containing a sulfanilamide and a 2,4-diamino-5-(2',4',5'-trisubstitutedbenzyl)pyrimidine
EP0015124B1 (fr)	1983-06-01	Dérivés d'éther hétérocyclique parasiticides, procédés pour leur préparation et compositions les contenant
US4010176A (en)	1977-03-01	Isoxazole substituted nitroimidazoles
US3487087A (en)	1969-12-30	Nitration of imidazoles
EP0116639A1 (fr)	1984-08-29	Acylguanidines
US3652579A (en)	1972-03-28	1-methyl-2-substituted 5-nitroimidazoles
FI86188B (fi)	1992-04-15	Foerfarande foer framstaellning av ett polycykliskt eterantibiotikum som kan anvaendas saosom laekemedel.
US4092424A (en)	1978-05-30	Antibiotic derivatives
US3020277A (en)	1962-02-06	1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts
US4173631A (en)	1979-11-06	7-Methyl-8-methylamino-10-(1'-D-ribityl)isoalloxazine
DE1670389A1 (de)	1970-11-05	Neue quaternaere 5-Ammonium-methyl-4-amino-pyrimidinsalzverbindungen
US3634446A (en)	1972-01-11	1-methyl-2-isopropyl-5-nitroimidazole and water soluble salts thereof
US4356264A (en)	1982-10-26	Zinc-containing antibiotic agents
US3088867A (en)	1963-05-07	Compositions for the control of coccidiosis
US3676439A (en)	1972-07-11	5,6-dihydro-8,8-dimethyl-3-nitro-8h imidazo(2-1-c) (1,4)oxazine
NO123461B (fr)	1971-11-22
DE1518045A1 (de)	1969-05-22	2-Alkoxy-4-subst.-Benzylverbindungen und Verfahren zu ihrer Herstellung
US4053602A (en)	1977-10-11	Compositions for treating coccidiosis containing 5-deazariboflavin and its derivatives
US4091094A (en)	1978-05-23	9-Azariboflavin and pharmaceutical composition containing same
US4154835A (en)	1979-05-15	Anthelmintic imidazo [1,2-a] pyridines
US4080340A (en)	1978-03-21	Nitroimidazoles
US3859443A (en)	1975-01-07	Composition and methods of treatment employing acrylanilides as anticoccidial agents
US3637702A (en)	1972-01-25	1-(hydroxyalkyl)-2-morpholinomethyl-5-nitroimidazoles
US3949079A (en)	1976-04-06	Antibiotic derivatives
US3654299A (en)	1972-04-04	Nitroimidazolyl antimicrobial agents