BE828979A - Nouveaux derives de 3-(5-nitroimidazol-2-yl)-pyrazolo (3,4-d)pyrimidine - Google Patents

Nouveaux derives de 3-(5-nitroimidazol-2-yl)-pyrazolo (3,4-d)pyrimidine

Info

Publication number: BE828979A
Authority: BE; Belgium
Prior art keywords: emi; product; mixture; identified; melting point
Prior art date: 1974-05-13

Application number

BE1006654A

Other languages

English (en)

French (fr)

Inventor

H Friedman

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.)

1974-05-13

Filing date

1975-05-13

Publication date

1975-11-13

1975-05-13 Application filed filed Critical

1975-11-13 Publication of BE828979A publication Critical patent/BE828979A/fr

Links

YDHZEKIXDCPSQO-UHFFFAOYSA-N 3-(5-nitro-1H-imidazol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine Chemical class N1C([N+](=O)[O-])=CN=C1C1=NNC2=NC=NC=C12 YDHZEKIXDCPSQO-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 93
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
239000000203 mixture Substances 0.000 description 84
239000000047 product Substances 0.000 description 82
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
238000002844 melting Methods 0.000 description 56
230000008018 melting Effects 0.000 description 56
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
239000007787 solid Substances 0.000 description 48
238000000921 elemental analysis Methods 0.000 description 39
239000007795 chemical reaction product Substances 0.000 description 35
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
238000012360 testing method Methods 0.000 description 26
239000002904 solvent Substances 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
238000010992 reflux Methods 0.000 description 22
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 21
238000002360 preparation method Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 20
-1 5-nitro-furyl group Chemical group 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
239000000725 suspension Substances 0.000 description 15
238000000034 method Methods 0.000 description 14
241000699670 Mus sp. Species 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000010790 dilution Methods 0.000 description 11
239000012895 dilution Substances 0.000 description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
238000001914 filtration Methods 0.000 description 10
239000012265 solid product Substances 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
NUGZBVBZIDWZAD-UHFFFAOYSA-N 1h-pyrazole-4-carbonitrile Chemical compound N#CC=1C=NNC=1 NUGZBVBZIDWZAD-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
238000005303 weighing Methods 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000000338 in vitro Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
241000606856 Pasteurella multocida Species 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000007857 hydrazones Chemical class 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
229940051027 pasteurella multocida Drugs 0.000 description 5
238000000746 purification Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
229920001817 Agar Polymers 0.000 description 4
241000287828 Gallus gallus Species 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
241000224527 Trichomonas vaginalis Species 0.000 description 4
239000008272 agar Substances 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
235000013330 chicken meat Nutrition 0.000 description 4
230000001747 exhibiting effect Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
150000002429 hydrazines Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
238000011534 incubation Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 3
HGBWQGJWYQJSEA-UHFFFAOYSA-N 1-methyl-5-nitro-2-(2-phenylethenyl)imidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=CC=2C=CC=CC=2)=N1 HGBWQGJWYQJSEA-UHFFFAOYSA-N 0.000 description 3
JLQLFVSTEDRFAD-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbaldehyde Chemical compound CN1C(C=O)=NC=C1[N+]([O-])=O JLQLFVSTEDRFAD-UHFFFAOYSA-N 0.000 description 3
FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
230000037396 body weight Effects 0.000 description 3
OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 3
229960001653 citalopram Drugs 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
OWPQUQSVZURPSP-UHFFFAOYSA-N n-[(1-methyl-5-nitroimidazol-2-yl)methylideneamino]methanamine Chemical compound CNN=CC1=NC=C([N+]([O-])=O)N1C OWPQUQSVZURPSP-UHFFFAOYSA-N 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
TZYQTWHRLVDYPL-UHFFFAOYSA-N 5h-pyrimidin-4-one Chemical compound O=C1CC=NC=N1 TZYQTWHRLVDYPL-UHFFFAOYSA-N 0.000 description 2
UCDBLYHPJMMFMY-UHFFFAOYSA-N 8-bromoquinoline-4-carbonitrile Chemical compound C1=CN=C2C(Br)=CC=CC2=C1C#N UCDBLYHPJMMFMY-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
241000251468 Actinopterygii Species 0.000 description 2
241000607528 Aeromonas hydrophila Species 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
244000037640 animal pathogen Species 0.000 description 2
230000000507 anthelmentic effect Effects 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000000078 anti-malarial effect Effects 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
230000002725 anti-mycoplasma Effects 0.000 description 2
230000000884 anti-protozoa Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229940041514 candida albicans extract Drugs 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 2
239000001177 diphosphate Substances 0.000 description 2
235000011180 diphosphates Nutrition 0.000 description 2
239000003651 drinking water Substances 0.000 description 2
235000020188 drinking water Nutrition 0.000 description 2
239000003814 drug Substances 0.000 description 2
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
230000008570 general process Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000010410 layer Substances 0.000 description 2
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
239000002609 medium Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
FGQSMXLNUMMHOR-UHFFFAOYSA-N methyl methanimidate Chemical compound COC=N FGQSMXLNUMMHOR-UHFFFAOYSA-N 0.000 description 2
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
238000005949 ozonolysis reaction Methods 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229930195734 saturated hydrocarbon Natural products 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 1
125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
RKVDCOCBGCOTJO-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)pyrazole Chemical group C1=CC=NN1C1=NC=CN1 RKVDCOCBGCOTJO-UHFFFAOYSA-N 0.000 description 1
SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 description 1
RKHRVKJTCSHZCR-UHFFFAOYSA-N 1-[bis(2-chloroethoxy)methoxy]-2-chloroethane Chemical compound ClCCOC(OCCCl)OCCCl RKHRVKJTCSHZCR-UHFFFAOYSA-N 0.000 description 1
IVXPLWROXBUJSE-UHFFFAOYSA-N 1-[bis(2-methylpropoxy)methoxy]-2-methylpropane Chemical compound CC(C)COC(OCC(C)C)OCC(C)C IVXPLWROXBUJSE-UHFFFAOYSA-N 0.000 description 1
JLZXSFPSJJMRIX-UHFFFAOYSA-N 1-methyl-5-nitroimidazole Chemical compound CN1C=NC=C1[N+]([O-])=O JLZXSFPSJJMRIX-UHFFFAOYSA-N 0.000 description 1
ZWKTYLHETWULIP-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbonyl bromide Chemical compound CN1C(C(Br)=O)=NC=C1[N+]([O-])=O ZWKTYLHETWULIP-UHFFFAOYSA-N 0.000 description 1
RGTMHUKTLKJHNW-UHFFFAOYSA-N 1H-pyrazole 1H-pyrimidin-2-one Chemical group N1C(N=CC=C1)=O.N1N=CC=C1 RGTMHUKTLKJHNW-UHFFFAOYSA-N 0.000 description 1
ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 1
QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 1
AVFCGLFLHBWEET-UHFFFAOYSA-N 1h-pyrazolo[4,3-d]pyrimidin-3-amine Chemical class N1=CN=C2C(N)=NNC2=C1 AVFCGLFLHBWEET-UHFFFAOYSA-N 0.000 description 1
UKAXKCXOBZGQAK-UHFFFAOYSA-N 2,5-dimethyl-4-nitro-1h-imidazole Chemical compound CC1=NC([N+]([O-])=O)=C(C)N1 UKAXKCXOBZGQAK-UHFFFAOYSA-N 0.000 description 1
HMBFFVBLMDIXOI-UHFFFAOYSA-N 2-[2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]hydrazinyl]ethanol Chemical compound CN1C(C=NNCCO)=NC=C1[N+]([O-])=O HMBFFVBLMDIXOI-UHFFFAOYSA-N 0.000 description 1
LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical compound NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 description 1
FJEBWUFRAQKJMU-UHFFFAOYSA-N 2-n,2-n-dimethylpropane-1,2,3-triamine Chemical compound CN(C)C(CN)CN FJEBWUFRAQKJMU-UHFFFAOYSA-N 0.000 description 1
WNLWBCIUNCAMPH-UHFFFAOYSA-N 2-n,2-n-dimethylpropane-1,2-diamine Chemical compound NCC(C)N(C)C WNLWBCIUNCAMPH-UHFFFAOYSA-N 0.000 description 1
WUWWRQBTTCHFBU-UHFFFAOYSA-N 3-[bis(2-ethylhexoxy)methoxymethyl]heptane Chemical compound CCCCC(CC)COC(OCC(CC)CCCC)OCC(CC)CCCC WUWWRQBTTCHFBU-UHFFFAOYSA-N 0.000 description 1
PKRKJRIVVOGXHM-UHFFFAOYSA-N 4-amino-1h-pyrazole-5-carbonitrile Chemical compound NC=1C=NNC=1C#N PKRKJRIVVOGXHM-UHFFFAOYSA-N 0.000 description 1
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
FKQVPUMXKPUGBH-UHFFFAOYSA-N 5-amino-1-methyl-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound N#CC1=C(N)N(C)N=C1C1=NC=C([N+]([O-])=O)N1C FKQVPUMXKPUGBH-UHFFFAOYSA-N 0.000 description 1
GEDGPTYHODZBEP-UHFFFAOYSA-N 6-(1h-imidazol-2-yl)-7-nitro-2h-triazolo[4,5-c]pyridazine Chemical class N1=NC=2N=NNC=2C([N+](=O)[O-])=C1C1=NC=CN1 GEDGPTYHODZBEP-UHFFFAOYSA-N 0.000 description 1
241000589893 Brachyspira hyodysenteriae Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
238000009631 Broth culture Methods 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001430197 Mollicutes Species 0.000 description 1
CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
241000606860 Pasteurella Species 0.000 description 1
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000589774 Pseudomonas sp. Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241001502500 Trichomonadida Species 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
150000008065 acid anhydrides Chemical class 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
230000000842 anti-protozoal effect Effects 0.000 description 1
230000001099 anti-trypanosomal effect Effects 0.000 description 1
239000003430 antimalarial agent Substances 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000002543 antimycotic Substances 0.000 description 1
239000003904 antiprotozoal agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
SWPPXVFKWWEYSV-UHFFFAOYSA-L chembl3186386 Chemical compound [Na+].[Na+].C1=C(C)C(C)=CC(C)=C1N=NC1=C(O)C(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=CC=C12 SWPPXVFKWWEYSV-UHFFFAOYSA-L 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003224 coccidiostatic agent Substances 0.000 description 1
230000002192 coccidiostatic effect Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012458 free base Substances 0.000 description 1
PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
229960001625 furazolidone Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
238000012812 general test Methods 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000013101 initial test Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
WQVHUKJEGJTYOW-UHFFFAOYSA-N n-[(1-methyl-5-nitroimidazol-2-yl)methylideneamino]ethanamine Chemical compound CCNN=CC1=NC=C([N+]([O-])=O)N1C WQVHUKJEGJTYOW-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
229960001907 nitrofurazone Drugs 0.000 description 1
150000004957 nitroimidazoles Chemical class 0.000 description 1
125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
229960003531 phenolsulfonphthalein Drugs 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 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
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003491 tear gas Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
239000001226 triphosphate Substances 0.000 description 1
235000011178 triphosphate Nutrition 0.000 description 1
230000000654 trypanocidal effect Effects 0.000 description 1
239000006150 trypticase soy agar Substances 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE1006654A 1974-05-13 1975-05-13 Nouveaux derives de 3-(5-nitroimidazol-2-yl)-pyrazolo (3,4-d)pyrimidine BE828979A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US46925674A	1974-05-13	1974-05-13

Publications (1)

Publication Number	Publication Date
BE828979A true BE828979A (fr)	1975-11-13

Family

ID=23863094

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE1006654A BE828979A (fr)	1974-05-13	1975-05-13	Nouveaux derives de 3-(5-nitroimidazol-2-yl)-pyrazolo (3,4-d)pyrimidine

Country Status (3)

Country	Link
AT (1)	ATA358375A (de)
BE (1)	BE828979A (de)
ZA (1)	ZA753024B (de)

1975
- 1975-05-12 ZA ZA00753024A patent/ZA753024B/xx unknown
- 1975-05-12 AT AT358375A patent/ATA358375A/de not_active IP Right Cessation
- 1975-05-13 BE BE1006654A patent/BE828979A/fr unknown

Also Published As

Publication number	Publication date
ATA358375A (de)	1977-10-15
ZA753024B (en)	1976-04-28

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