AT307396B - Verfahren zur Herstellung von neuen 2-(5-Nitro-2-furyl)-thieno[3,2-d]pyrimidinen und ihren Säureadditionssalzen - Google Patents
Verfahren zur Herstellung von neuen 2-(5-Nitro-2-furyl)-thieno[3,2-d]pyrimidinen und ihren SäureadditionssalzenInfo
- Publication number
- AT307396B AT307396B AT1067770A AT1067770A AT307396B AT 307396 B AT307396 B AT 307396B AT 1067770 A AT1067770 A AT 1067770A AT 1067770 A AT1067770 A AT 1067770A AT 307396 B AT307396 B AT 307396B
- Authority
- AT
- Austria
- Prior art keywords
- group
- thieno
- carbon atoms
- furyl
- nitro
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 9
- KBPSPKWGHFXGIY-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidine Chemical class [N+](=O)([O-])C1=CC=C(O1)C=1N=CC2=C(N1)C=CS2 KBPSPKWGHFXGIY-UHFFFAOYSA-N 0.000 title claims description 7
- -1 cyclohexylamino group Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 235000005985 organic acids Nutrition 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000012433 hydrogen halide Substances 0.000 claims description 7
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical group C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 20
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- QXOSUPOIJVYTSR-UHFFFAOYSA-N 4-chloro-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidine Chemical compound ClC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=CS2 QXOSUPOIJVYTSR-UHFFFAOYSA-N 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RLEAOXPVSPRGQA-UHFFFAOYSA-N 4-chloro-6-methyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidine Chemical compound ClC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=C(S2)C RLEAOXPVSPRGQA-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CUQARRMMLNJPTN-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)-1H-thieno[3,2-d]pyrimidine-4-thione Chemical compound SC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=CS2 CUQARRMMLNJPTN-UHFFFAOYSA-N 0.000 description 2
- ZBBDUTXZIZKYDM-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound NC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=CS2 ZBBDUTXZIZKYDM-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- GBAXGHVGQJHFQL-UHFFFAOYSA-N 1-(2-hydroxyethylamino)propan-2-ol Chemical compound CC(O)CNCCO GBAXGHVGQJHFQL-UHFFFAOYSA-N 0.000 description 1
- KLQJBTIOGWXSSO-UHFFFAOYSA-N 1-(diethylamino)-3-[[2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]amino]propan-2-ol Chemical compound C(C)N(CC(CNC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2)O)CC KLQJBTIOGWXSSO-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- WFQDUPNKQALFCI-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)-4-piperidin-1-ylthieno[3,2-d]pyrimidine Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)N1CCCCC1 WFQDUPNKQALFCI-UHFFFAOYSA-N 0.000 description 1
- QAKNZBUWSSZCOE-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)-4-pyrrolidin-1-ylthieno[3,2-d]pyrimidine Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)N1CCCC1 QAKNZBUWSSZCOE-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KKWFVRLGOOQCST-UHFFFAOYSA-N 2-[4-[6-methyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CC1)C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=C(S2)C KKWFVRLGOOQCST-UHFFFAOYSA-N 0.000 description 1
- WARYFAQRFKSTBR-UHFFFAOYSA-N 2-[[2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]amino]-1-phenylethanol Chemical compound OC(CNC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2)C1=CC=CC=C1 WARYFAQRFKSTBR-UHFFFAOYSA-N 0.000 description 1
- OJGWDVGFPXZUME-UHFFFAOYSA-N 2-[[2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]amino]phenol Chemical compound OC1=C(NC=2C3=C(N=C(N=2)C=2OC(=CC=2)[N+](=O)[O-])C=CS3)C=CC=C1 OJGWDVGFPXZUME-UHFFFAOYSA-N 0.000 description 1
- CERUXSWZYMERLM-UHFFFAOYSA-N 2-[ethyl-[2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]amino]ethanol Chemical compound C(C)N(C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2)CCO CERUXSWZYMERLM-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- CXMYWOCYTPKBPP-UHFFFAOYSA-N 3-(3-hydroxypropylamino)propan-1-ol Chemical compound OCCCNCCCO CXMYWOCYTPKBPP-UHFFFAOYSA-N 0.000 description 1
- KRGXWTOLFOPIKV-UHFFFAOYSA-N 3-(methylamino)propan-1-ol Chemical compound CNCCCO KRGXWTOLFOPIKV-UHFFFAOYSA-N 0.000 description 1
- KTKSXMPFLQVGCS-UHFFFAOYSA-N 3-[[6-methyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]amino]propane-1,2-diol Chemical compound OC(CNC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=C(S2)C)CO KTKSXMPFLQVGCS-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical class NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- RDMVHCYBNQLOPP-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidine Chemical compound CN1CCN(CC1)C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 RDMVHCYBNQLOPP-UHFFFAOYSA-N 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- LFAJPUUJEMDRGK-UHFFFAOYSA-N 4-methyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidine-6-thiol Chemical compound CC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=C(S2)S LFAJPUUJEMDRGK-UHFFFAOYSA-N 0.000 description 1
- AQYFUOXDSMBZMB-UHFFFAOYSA-N 4-methylsulfanyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidine Chemical compound CSC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 AQYFUOXDSMBZMB-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- NDIZKKIFFZCYBM-UHFFFAOYSA-N C(C1=CC=CC=C1)NC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 Chemical compound C(C1=CC=CC=C1)NC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 NDIZKKIFFZCYBM-UHFFFAOYSA-N 0.000 description 1
- RLCWRLMYGRZPHN-UHFFFAOYSA-N CC(CN(CCO)C1=NC(C2=CC=C([N+]([O-])=O)O2)=NC2=C1SC=C2)O Chemical compound CC(CN(CCO)C1=NC(C2=CC=C([N+]([O-])=O)O2)=NC2=C1SC=C2)O RLCWRLMYGRZPHN-UHFFFAOYSA-N 0.000 description 1
- HCDVWQTYHOPUIR-UHFFFAOYSA-N CC1=CC(N=C(C2=CC=C([N+]([O-])=O)O2)N=C2N(CCO)CCO)=C2S1 Chemical compound CC1=CC(N=C(C2=CC=C([N+]([O-])=O)O2)N=C2N(CCO)CCO)=C2S1 HCDVWQTYHOPUIR-UHFFFAOYSA-N 0.000 description 1
- NYLXQVUFSVSTJR-UHFFFAOYSA-N CC1=CC=C(NC=2C3=C(N=C(N=2)C=2OC(=CC=2)[N+](=O)[O-])C=CS3)C=C1 Chemical compound CC1=CC=C(NC=2C3=C(N=C(N=2)C=2OC(=CC=2)[N+](=O)[O-])C=CS3)C=C1 NYLXQVUFSVSTJR-UHFFFAOYSA-N 0.000 description 1
- HUKIKPLWKLTUHD-UHFFFAOYSA-N CCCCN(CCO)C1=NC(C2=CC=C([N+]([O-])=O)O2)=NC2=C1SC=C2 Chemical compound CCCCN(CCO)C1=NC(C2=CC=C([N+]([O-])=O)O2)=NC2=C1SC=C2 HUKIKPLWKLTUHD-UHFFFAOYSA-N 0.000 description 1
- RFBHGJRZEJKJPA-UHFFFAOYSA-N CCOC(N(CC1)CCN1C1=NC(C2=CC=C([N+]([O-])=O)O2)=NC2=C1SC=C2)=O Chemical compound CCOC(N(CC1)CCN1C1=NC(C2=CC=C([N+]([O-])=O)O2)=NC2=C1SC=C2)=O RFBHGJRZEJKJPA-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- PECZXQDJZWBGKN-UHFFFAOYSA-N N',N'-dimethyl-N-[2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]propane-1,3-diamine Chemical compound CN(CCCNC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=CS2)C PECZXQDJZWBGKN-UHFFFAOYSA-N 0.000 description 1
- FABBOWUOLXCVJR-UHFFFAOYSA-N N(C1=CC=CC=C1)C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 Chemical compound N(C1=CC=CC=C1)C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 FABBOWUOLXCVJR-UHFFFAOYSA-N 0.000 description 1
- AFTPNAGRMFTBNT-UHFFFAOYSA-N N-(2-methoxyethyl)-6-methyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound COCCNC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=C(S2)C AFTPNAGRMFTBNT-UHFFFAOYSA-N 0.000 description 1
- ATVXMBWFLZSJQK-UHFFFAOYSA-N N-cyclohexyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1(CCCCC1)NC=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 ATVXMBWFLZSJQK-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- GFUUDWCOGYNNKX-UHFFFAOYSA-N OC(CN(C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2)CC(C)O)C Chemical compound OC(CN(C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2)CC(C)O)C GFUUDWCOGYNNKX-UHFFFAOYSA-N 0.000 description 1
- DQRWNUMKSUNBQQ-UHFFFAOYSA-N OCCCN(C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2)C Chemical compound OCCCN(C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2)C DQRWNUMKSUNBQQ-UHFFFAOYSA-N 0.000 description 1
- GQVMOSCLTMRCFV-UHFFFAOYSA-N OCCN1CCN(CC1)C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 Chemical compound OCCN1CCN(CC1)C=1C2=C(N=C(N=1)C=1OC(=CC=1)[N+](=O)[O-])C=CS2 GQVMOSCLTMRCFV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- JLUYFUNVMHPNNJ-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)N1CCSCC1 Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)N1CCSCC1 JLUYFUNVMHPNNJ-UHFFFAOYSA-N 0.000 description 1
- QQMLGPDFWSRKLU-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)NC(CC)=O Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)NC(CC)=O QQMLGPDFWSRKLU-UHFFFAOYSA-N 0.000 description 1
- GCYITGVLMHIFJL-UHFFFAOYSA-N [O-][N+](C1=CC=C(C(N=C2NC3=CC(Cl)=CC=C3)=NC3=C2SC=C3)O1)=O Chemical compound [O-][N+](C1=CC=C(C(N=C2NC3=CC(Cl)=CC=C3)=NC3=C2SC=C3)O1)=O GCYITGVLMHIFJL-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000000003 vaginal tablet Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691959403 DE1959403A1 (de) | 1969-11-26 | 1969-11-26 | Neue 2-(5-Nitro-2-furyl)-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
| DE19702050815 DE2050815A1 (de) | 1970-10-16 | 1970-10-16 | Neue 2-(5-Nitro-2-furyl)-thieno eckige Klammer auf 3,2-d eckige Klammer zu pyrimidine |
| DE19702050816 DE2050816A1 (de) | 1970-10-16 | 1970-10-16 | Neue 2-(Nitro-2-furyl>thieno eckige Klammer auf 3,2-d eckige Klammer zu pyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT307396B true AT307396B (de) | 1973-05-25 |
Family
ID=27182251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT1067770A AT307396B (de) | 1969-11-26 | 1970-11-26 | Verfahren zur Herstellung von neuen 2-(5-Nitro-2-furyl)-thieno[3,2-d]pyrimidinen und ihren Säureadditionssalzen |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT307396B (ro) |
| ES (2) | ES385770A1 (ro) |
| PL (1) | PL85052B1 (ro) |
| RO (1) | RO58535A (ro) |
-
1970
- 1970-11-21 ES ES385770A patent/ES385770A1/es not_active Expired
- 1970-11-21 ES ES385771A patent/ES385771A1/es not_active Expired
- 1970-11-24 RO RO67443A patent/RO58535A/ro unknown
- 1970-11-25 PL PL1970144640A patent/PL85052B1/pl unknown
- 1970-11-26 AT AT1067770A patent/AT307396B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES385771A1 (es) | 1973-11-16 |
| PL85052B1 (ro) | 1976-04-30 |
| ES385770A1 (es) | 1973-11-16 |
| RO58535A (ro) | 1975-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |