PL83278B1 - - Google Patents
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- Publication number
- PL83278B1 PL83278B1 PL1972154083A PL15408372A PL83278B1 PL 83278 B1 PL83278 B1 PL 83278B1 PL 1972154083 A PL1972154083 A PL 1972154083A PL 15408372 A PL15408372 A PL 15408372A PL 83278 B1 PL83278 B1 PL 83278B1
- Authority
- PL
- Poland
- Prior art keywords
- pyrimidine
- furyl
- ethoxy
- product
- nitro
- Prior art date
Links
- -1 amine compound Chemical class 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 238000006396 nitration reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- LAIZBXNIUKWPOC-UHFFFAOYSA-N 2-(furan-2-yl)-4-nitropyrimidine Chemical class [N+](=O)([O-])C1=NC(=NC=C1)C=1OC=CC1 LAIZBXNIUKWPOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- 239000000047 product Substances 0.000 description 63
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 22
- 238000001953 recrystallisation Methods 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 11
- 229910017604 nitric acid Inorganic materials 0.000 description 11
- XQQIGLPLFSRAJT-UHFFFAOYSA-N 2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl 4-methylbenzenesulfonate Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCOS(=O)(=O)C1=CC=C(C=C1)C XQQIGLPLFSRAJT-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- AMUVIGZHRASSQV-UHFFFAOYSA-N 2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl 4-methylbenzenesulfonate Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCOS(=O)(=O)C1=CC=C(C=C1)C AMUVIGZHRASSQV-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 229960000564 nitrofurantoin Drugs 0.000 description 5
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- NEDIWVSOTZMHEV-UHFFFAOYSA-N 2-[acetyl-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]amino]ethyl acetate Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)CCOC(C)=O NEDIWVSOTZMHEV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DXJWVKJFZYGBHQ-UHFFFAOYSA-N N-[2-(dimethylamino)ethyl]-N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)CCN(C)C DXJWVKJFZYGBHQ-UHFFFAOYSA-N 0.000 description 3
- QTXXMLNRTJSXHD-UHFFFAOYSA-N N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]propan-1-amine Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCNCCC QTXXMLNRTJSXHD-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- NNFAONNFUZQJNX-UHFFFAOYSA-N 1-[acetyl-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]amino]propan-2-yl acetate Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)CC(C)OC(C)=O NNFAONNFUZQJNX-UHFFFAOYSA-N 0.000 description 2
- MWBLQQNQHOTLGM-UHFFFAOYSA-N 2-[2-(furan-2-yl)pyrimidin-5-yl]oxy-N-methylethanamine Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCNC MWBLQQNQHOTLGM-UHFFFAOYSA-N 0.000 description 2
- NFFWWFNBTZGOKR-UHFFFAOYSA-N 2-[acetyl-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]amino]ethyl acetate Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)CCOC(C)=O NFFWWFNBTZGOKR-UHFFFAOYSA-N 0.000 description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- GHNUNQGNRVTNEP-UHFFFAOYSA-N Cl.Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCN(C)C Chemical compound Cl.Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCN(C)C GHNUNQGNRVTNEP-UHFFFAOYSA-N 0.000 description 2
- BXZNQYPZFDCTEF-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCO Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCO BXZNQYPZFDCTEF-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ANLMMHDZDZXULQ-UHFFFAOYSA-N N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]-N-propan-2-ylacetamide Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)C(C)C ANLMMHDZDZXULQ-UHFFFAOYSA-N 0.000 description 2
- UIRJRQSEJGGSLT-UHFFFAOYSA-N N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]-N-propylacetamide Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)CCC UIRJRQSEJGGSLT-UHFFFAOYSA-N 0.000 description 2
- DHNVGJJJDGHEHW-UHFFFAOYSA-N N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]-N-propylformamide Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C=O)CCC DHNVGJJJDGHEHW-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000224527 Trichomonas vaginalis Species 0.000 description 2
- HXAQOHNAVZNYBI-UHFFFAOYSA-N [3-[acetyl-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]amino]-2-acetyloxypropyl] acetate Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)CC(COC(C)=O)OC(C)=O HXAQOHNAVZNYBI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
- JAFQDGMSDBAEPM-UHFFFAOYSA-N oxolane;2-propan-2-yloxypropane Chemical compound C1CCOC1.CC(C)OC(C)C JAFQDGMSDBAEPM-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- ZKSLTNVRJAMYRG-UHFFFAOYSA-N 1-[acetyl-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]amino]propan-2-yl acetate Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)CC(C)OC(C)=O ZKSLTNVRJAMYRG-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- KKKFDOUPVIXPDD-UHFFFAOYSA-N 2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxy-N-(oxolan-2-ylmethyl)ethanamine hydrochloride Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCC1OCCC1 KKKFDOUPVIXPDD-UHFFFAOYSA-N 0.000 description 1
- CPRNZFRBSOXRJR-UHFFFAOYSA-N 2-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethylamino]butan-1-ol Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC(CO)CC CPRNZFRBSOXRJR-UHFFFAOYSA-N 0.000 description 1
- YMCHOBMHQYUKST-UHFFFAOYSA-N 2-[acetyl-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]amino]butyl acetate Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)C(COC(C)=O)CC YMCHOBMHQYUKST-UHFFFAOYSA-N 0.000 description 1
- VACJHIUSZPBOOF-UHFFFAOYSA-N 3-aminopropane-1,1-diol Chemical compound NCCC(O)O VACJHIUSZPBOOF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000222122 Candida albicans Species 0.000 description 1
- SSQKNWWTYXKCDP-UHFFFAOYSA-N Cl.Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCN(CC)CC Chemical compound Cl.Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCN(CC)CC SSQKNWWTYXKCDP-UHFFFAOYSA-N 0.000 description 1
- SWBPBKJXEPIRGN-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC SWBPBKJXEPIRGN-UHFFFAOYSA-N 0.000 description 1
- PTYPPQOXAWWWAS-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC1CCCCC1 Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC1CCCCC1 PTYPPQOXAWWWAS-UHFFFAOYSA-N 0.000 description 1
- MLUINZMYZMFPRA-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCC(C)O Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCC(C)O MLUINZMYZMFPRA-UHFFFAOYSA-N 0.000 description 1
- CRGRAVZQTXCNPF-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCOC Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCOC CRGRAVZQTXCNPF-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 108010010803 Gelatin Proteins 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
- YFACAJGUCIYLAP-UHFFFAOYSA-N N-(2-hydroxyethyl)-N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)CCO YFACAJGUCIYLAP-UHFFFAOYSA-N 0.000 description 1
- BEPGGQDOAOFWGM-UHFFFAOYSA-N N-(2-methoxyethyl)-N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)CCOC BEPGGQDOAOFWGM-UHFFFAOYSA-N 0.000 description 1
- NSJJTPKNFIRDNV-UHFFFAOYSA-N N-[2-(diethylamino)ethyl]-N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)CCN(CC)CC NSJJTPKNFIRDNV-UHFFFAOYSA-N 0.000 description 1
- JWZAEKVXCQAOTB-UHFFFAOYSA-N N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]-N-propan-2-ylacetamide Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)C(C)C JWZAEKVXCQAOTB-UHFFFAOYSA-N 0.000 description 1
- JPBPNUFKTRJHBD-UHFFFAOYSA-N N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]-N-propylformamide Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C=O)CCC JPBPNUFKTRJHBD-UHFFFAOYSA-N 0.000 description 1
- LULKZTJUCBWRSB-UHFFFAOYSA-N N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]cyclopentanamine hydrochloride Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNC1CCCC1 LULKZTJUCBWRSB-UHFFFAOYSA-N 0.000 description 1
- LLXZZDUPFGSPHR-UHFFFAOYSA-N N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]propan-1-amine hydrochloride Chemical compound Cl.[N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCNCCC LLXZZDUPFGSPHR-UHFFFAOYSA-N 0.000 description 1
- LNSRFLYFMXJQOF-UHFFFAOYSA-N N-benzyl-N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)CC1=CC=CC=C1 LNSRFLYFMXJQOF-UHFFFAOYSA-N 0.000 description 1
- KDLFBOZOINQSHE-UHFFFAOYSA-N N-butan-2-yl-N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)C(C)CC KDLFBOZOINQSHE-UHFFFAOYSA-N 0.000 description 1
- WULHPKSMWSQHAO-UHFFFAOYSA-N N-cyclohexyl-N-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=C(C=N1)OCCN(C(C)=O)C1CCCCC1 WULHPKSMWSQHAO-UHFFFAOYSA-N 0.000 description 1
- GTWZSBSQAOGSMG-UHFFFAOYSA-N N-ethyl-N-[2-[2-(furan-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)CC GTWZSBSQAOGSMG-UHFFFAOYSA-N 0.000 description 1
- LTOMMOKWGRNSOH-UHFFFAOYSA-N O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)CCCC Chemical compound O1C(=CC=C1)C1=NC=C(C=N1)OCCN(C(C)=O)CCCC LTOMMOKWGRNSOH-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 206010041925 Staphylococcal infections Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 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
- 150000004820 halides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- MWSFUDBQVPYDHJ-UHFFFAOYSA-N n-butyl-n-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound N1=CC(OCCN(CCCC)C(C)=O)=CN=C1C1=CC=C([N+]([O-])=O)O1 MWSFUDBQVPYDHJ-UHFFFAOYSA-N 0.000 description 1
- MOQUMOQRDADQHO-UHFFFAOYSA-N n-ethyl-n-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound N1=CC(OCCN(CC)C(C)=O)=CN=C1C1=CC=C([N+]([O-])=O)O1 MOQUMOQRDADQHO-UHFFFAOYSA-N 0.000 description 1
- FOWWOGMDSHLJPW-UHFFFAOYSA-N n-methyl-n-[2-[2-(5-nitrofuran-2-yl)pyrimidin-5-yl]oxyethyl]acetamide Chemical compound N1=CC(OCCN(C)C(C)=O)=CN=C1C1=CC=C([N+]([O-])=O)O1 FOWWOGMDSHLJPW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2113529A DE2113529C3 (de) | 1971-03-17 | 1971-03-17 | 2-(5-Nitro-2-furyl)-5-(2-alkylaminoäthoxy)-pyrimidin-Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83278B1 true PL83278B1 (en:Method) | 1975-12-31 |
Family
ID=5802207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972154083A PL83278B1 (en:Method) | 1971-03-17 | 1972-03-15 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3846428A (en:Method) |
| AT (1) | AT312589B (en:Method) |
| AU (1) | AU463550B2 (en:Method) |
| BE (1) | BE780879A (en:Method) |
| CA (1) | CA945557A (en:Method) |
| CH (1) | CH575943A5 (en:Method) |
| DD (1) | DD96950A5 (en:Method) |
| DE (1) | DE2113529C3 (en:Method) |
| DK (1) | DK126999B (en:Method) |
| ES (1) | ES400560A1 (en:Method) |
| FR (1) | FR2130327B1 (en:Method) |
| GB (1) | GB1391933A (en:Method) |
| HU (1) | HU163178B (en:Method) |
| IL (1) | IL38962A (en:Method) |
| NL (1) | NL7203650A (en:Method) |
| PL (1) | PL83278B1 (en:Method) |
| SU (1) | SU458130A3 (en:Method) |
| ZA (1) | ZA721689B (en:Method) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1937629C3 (de) * | 1969-07-19 | 1979-07-26 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Nitrofuryl-aminoalkoxy-pyriinidine |
-
1971
- 1971-03-17 DE DE2113529A patent/DE2113529C3/de not_active Expired
-
1972
- 1972-02-29 DK DK93172AA patent/DK126999B/da unknown
- 1972-03-02 SU SU1754975A patent/SU458130A3/ru active
- 1972-03-08 ES ES400560A patent/ES400560A1/es not_active Expired
- 1972-03-08 AU AU39769/72A patent/AU463550B2/en not_active Expired
- 1972-03-12 IL IL38962A patent/IL38962A/xx unknown
- 1972-03-13 ZA ZA721689A patent/ZA721689B/xx unknown
- 1972-03-13 GB GB1152872A patent/GB1391933A/en not_active Expired
- 1972-03-15 DD DD161547A patent/DD96950A5/xx unknown
- 1972-03-15 PL PL1972154083A patent/PL83278B1/pl unknown
- 1972-03-16 FR FR7209187A patent/FR2130327B1/fr not_active Expired
- 1972-03-16 US US00235426A patent/US3846428A/en not_active Expired - Lifetime
- 1972-03-16 HU HUSC379A patent/HU163178B/hu unknown
- 1972-03-16 CH CH385372A patent/CH575943A5/xx not_active IP Right Cessation
- 1972-03-17 AT AT230072A patent/AT312589B/de not_active IP Right Cessation
- 1972-03-17 CA CA137,369A patent/CA945557A/en not_active Expired
- 1972-03-17 BE BE780879A patent/BE780879A/xx unknown
- 1972-03-17 NL NL7203650A patent/NL7203650A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7203650A (en:Method) | 1972-09-19 |
| AU463550B2 (en) | 1975-07-14 |
| ZA721689B (en) | 1972-12-27 |
| CA945557A (en) | 1974-04-16 |
| BE780879A (fr) | 1972-09-18 |
| FR2130327A1 (en:Method) | 1972-11-03 |
| DE2113529A1 (de) | 1972-12-14 |
| HU163178B (en:Method) | 1973-06-28 |
| AT312589B (de) | 1974-01-10 |
| DD96950A5 (en:Method) | 1973-04-12 |
| IL38962A (en) | 1975-10-15 |
| AU3976972A (en) | 1973-09-13 |
| DE2113529B2 (de) | 1979-08-02 |
| SU458130A3 (ru) | 1975-01-25 |
| IL38962A0 (en) | 1972-05-30 |
| DK126999B (da) | 1973-09-10 |
| ES400560A1 (es) | 1975-02-01 |
| CH575943A5 (en:Method) | 1976-05-31 |
| GB1391933A (en) | 1975-04-23 |
| DE2113529C3 (de) | 1980-04-30 |
| US3846428A (en) | 1974-11-05 |
| FR2130327B1 (en:Method) | 1975-04-25 |
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