NO129954B - - Google Patents

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Publication number: NO129954B
Authority: NO; Norway
Prior art keywords: furyl; pyrimidine; nitro; group; thieno
Prior art date: 1969-11-26

Application number

NO04524/70A

Other languages

English (en)

Norwegian (no)

Inventor

E Woitun

W Reuter

Original Assignee

Thomae Gmbh Dr K

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.)

1969-11-26

Filing date

1970-11-25

Publication date

1974-06-17

1969-11-26 Priority claimed from DE19691959403 external-priority patent/DE1959403A1/de

1970-10-16 Priority claimed from DE19702050816 external-priority patent/DE2050816A1/de

1970-10-16 Priority claimed from DE19702050815 external-priority patent/DE2050815A1/de

1970-10-16 Priority claimed from DE19702050814 external-priority patent/DE2050814A1/de

1970-11-25 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1974-06-17 Publication of NO129954B publication Critical patent/NO129954B/no

Links

150000001875 compounds Chemical class 0.000 claims description 44
-1 cyclohexylamino group Chemical group 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 12
229910017604 nitric acid Inorganic materials 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000002947 alkylene group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000004442 acylamino group Chemical group 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
235000005985 organic acids Nutrition 0.000 claims description 5
239000002798 polar solvent Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
150000003230 pyrimidines Chemical class 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
238000006396 nitration reaction Methods 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000005122 aminoalkylamino group Chemical group 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
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
230000000802 nitrating effect Effects 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 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
230000007306 turnover Effects 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 183
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 169
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 102
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 29
238000002844 melting Methods 0.000 description 28
230000008018 melting Effects 0.000 description 28
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 14
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
239000000203 mixture Substances 0.000 description 12
239000000126 substance Substances 0.000 description 12
229960001760 dimethyl sulfoxide Drugs 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
239000005457 ice water Substances 0.000 description 8
239000000047 product Substances 0.000 description 7
239000004317 sodium nitrate Substances 0.000 description 7
235000010344 sodium nitrate Nutrition 0.000 description 7
235000010288 sodium nitrite Nutrition 0.000 description 7
239000007858 starting material Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
229910002651 NO3 Inorganic materials 0.000 description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 3
KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 3
CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical compound NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
125000004494 ethyl ester group Chemical group 0.000 description 3
229940093915 gynecological organic acid Drugs 0.000 description 3
DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-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
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 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
MTEDAIZODVWXOZ-UHFFFAOYSA-N BrC1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 Chemical compound BrC1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 MTEDAIZODVWXOZ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-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
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000224527 Trichomonas vaginalis Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Chemical class 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 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
238000009835 boiling Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
TWEQNZZOOFKOER-UHFFFAOYSA-N methyl 3-aminothiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1N TWEQNZZOOFKOER-UHFFFAOYSA-N 0.000 description 2
229940032007 methylethyl ketone Drugs 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
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 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
239000008096 xylene Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-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
LEJMOTVCCRDZNE-UHFFFAOYSA-N 1-amino-3-(diethylamino)propan-2-ol Chemical compound CCN(CC)CC(O)CN LEJMOTVCCRDZNE-UHFFFAOYSA-N 0.000 description 1
VVLRHPRRBROYJC-UHFFFAOYSA-N 2-(5-bromofuran-2-yl)-N-methylthieno[3,2-d]pyrimidin-4-amine Chemical compound BrC1=CC=C(O1)C=1N=C(C2=C(N=1)C=CS2)NC VVLRHPRRBROYJC-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
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
PQMCFTMVQORYJC-UHFFFAOYSA-N 2-aminocyclohexan-1-ol Chemical compound NC1CCCCC1O PQMCFTMVQORYJC-UHFFFAOYSA-N 0.000 description 1
BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 1
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
IFPJFPROEPHIMI-UHFFFAOYSA-N 3-(2-hydroxyethylamino)propan-1-ol Chemical compound OCCCNCCO IFPJFPROEPHIMI-UHFFFAOYSA-N 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
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
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
ZERSFCPHVSFPCG-UHFFFAOYSA-N 4-[[2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-yl]amino]butan-1-ol Chemical compound OCCCCNC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=CS2 ZERSFCPHVSFPCG-UHFFFAOYSA-N 0.000 description 1
BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-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
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
YELBDMQEYQPIDK-UHFFFAOYSA-N 5-(5-hydroxypentylamino)pentan-1-ol Chemical compound OCCCCCNCCCCCO YELBDMQEYQPIDK-UHFFFAOYSA-N 0.000 description 1
LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
HHHCADSYQQJUGV-UHFFFAOYSA-N 5-cyanofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C#N)O1 HHHCADSYQQJUGV-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
SFETWDMUSWODEC-UHFFFAOYSA-N CC1=CC2=C(S1)C(=NC(=N2)C3=CC=C(O3)[N+](=O)[O-])NCCNC(=O)C Chemical compound CC1=CC2=C(S1)C(=NC(=N2)C3=CC=C(O3)[N+](=O)[O-])NCCNC(=O)C SFETWDMUSWODEC-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
VFYKJFDVFDYXFF-UHFFFAOYSA-N N-methyl-2-(5-nitrofuran-2-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N1)C=CS2)NC VFYKJFDVFDYXFF-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
JNXHFEDSNGVCID-UHFFFAOYSA-N OC(CNC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=CS2)CO Chemical compound OC(CNC=1C2=C(N=C(N1)C=1OC(=CC1)[N+](=O)[O-])C=CS2)CO JNXHFEDSNGVCID-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
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
241000224526 Trichomonas 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
150000008065 acid anhydrides Chemical class 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
239000003463 adsorbent Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000003716 antitrichomonal agent Substances 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000002140 halogenating effect Effects 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
239000012442 inert solvent Substances 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
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-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
FVKMOPIFLCMZMI-UHFFFAOYSA-N methyl 3-amino-5-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C)=CC=1N FVKMOPIFLCMZMI-UHFFFAOYSA-N 0.000 description 1
WNBJXNGNGVOCKO-UHFFFAOYSA-N methyl 5-cyanofuran-2-carboxylate Chemical compound COC(=O)C1=CC=C(C#N)O1 WNBJXNGNGVOCKO-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
235000010755 mineral Nutrition 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
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 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
YFZBPSXRYCOKCW-UHFFFAOYSA-N n-(3-aminopropyl)acetamide Chemical compound CC(=O)NCCCN YFZBPSXRYCOKCW-UHFFFAOYSA-N 0.000 description 1
ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 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
238000013207 serial dilution Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical group C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
239000000003 vaginal tablet Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO04524/70A 1969-11-26 1970-11-25 NO129954B (ja)

Applications Claiming Priority (4)

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
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
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
DE19702050814 DE2050814A1 (de)	1970-10-16	1970-10-16	Neue Verfahren zur Herstellung von 2-(5-Nitro-2-furyl)-thieno eckige Klammer auf 3,2-d eckige Klammer zu pyrimidinen

Publications (1)

Publication Number	Publication Date
NO129954B true NO129954B (ja)	1974-06-17

Family

ID=27430978

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO04524/70A NO129954B (ja)	1969-11-26	1970-11-25

Country Status (13)

Country	Link
US (1)	US3661908A (ja)
BE (1)	BE759493A (ja)
BG (2)	BG17800A3 (ja)
CA (1)	CA926865A (ja)
CH (3)	CH559210A5 (ja)
DK (1)	DK128781B (ja)
FR (1)	FR2073416B1 (ja)
GB (1)	GB1321316A (ja)
IE (1)	IE34765B1 (ja)
IL (1)	IL35729A (ja)
NL (1)	NL7017210A (ja)
NO (1)	NO129954B (ja)
SE (1)	SE377938B (ja)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
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US3932642A (en) *	1971-04-10	1976-01-13	Boehringer Ingelheim Gmbh	Biocidal compositions containing a 2- (5'-nitro-2'-furyl)-thieno(2,3-d) pyrimidine and methods of use
US6187777B1 (en)	1998-02-06	2001-02-13	Amgen Inc.	Compounds and methods which modulate feeding behavior and related diseases
US6608053B2 (en) *	2000-04-27	2003-08-19	Yamanouchi Pharmaceutical Co., Ltd.	Fused heteroaryl derivatives
US20040138238A1 (en) *	2002-08-08	2004-07-15	Dhanoa Dale S.	Substituted aminopyrimidine compounds as neurokinin antagonists
GB0423653D0 (en)	2004-10-25	2004-11-24	Piramed Ltd	Pharmaceutical compounds
TW200801012A (en)	2006-04-26	2008-01-01	Piramed Ltd	Phosphoinositide 3-kinase inhibitor compounds and methods of use
TWI498332B (zh) *	2006-04-26	2015-09-01	Hoffmann La Roche	作為pi3k抑制劑之嘧啶衍生物及相關製備方法、醫藥組合物、用途、套組及產物
WO2007129161A2 (en) *	2006-04-26	2007-11-15	F. Hoffmann-La Roche Ag	Thieno [3, 2-d] pyrimidine derivative useful as pi3k inhibitor
RU2470936C2 (ru) *	2006-12-07	2012-12-27	Дженентек, Инк.	Соединения-ингибиторы фосфоинозитид 3-киназы и способы применения
MX2009005950A (es)	2006-12-07	2009-10-12	Genentech Inc	Compuestos inhibidores de fosfoinositido 3-quinasas y metodos de uso.
US7893060B2 (en) *	2007-06-12	2011-02-22	F. Hoffmann-La Roche Ag	Thiazolopyrimidines and their use as inhibitors of phosphatidylinositol-3 kinase
CA2704711C (en) *	2007-09-24	2016-07-05	Genentech, Inc.	Thiazolopyrimidine p13k inhibitor compounds and methods of use
JP5348725B2 (ja) *	2007-10-25	2013-11-20	ジェネンテック，インコーポレイテッド	チエノピリミジン化合物の製造方法
GB0721095D0 (en) *	2007-10-26	2007-12-05	Piramed Ltd	Pharmaceutical compounds
JP5709766B2 (ja)	2009-03-12	2015-04-30	ジェネンテック，インコーポレイテッド	造血器腫瘍の治療のためのホスホイノシチド３キナーゼ阻害剤化合物と化学療法剤の併用
BRPI1009022A2 (pt) *	2009-05-27	2016-03-08	Hoffmann La Roche	"composto, composição farmacêutica, processo para produzir uma composição farmacêutica, uso de um composto, método para tratamento de uma doença ou transtorno e kit"
US8158625B2 (en) *	2009-05-27	2012-04-17	Genentech, Inc.	Bicyclic indole-pyrimidine PI3K inhibitor compounds selective for P110 delta, and methods of use
CA2776944A1 (en) *	2009-10-12	2011-05-12	F. Hoffmann-La Roche Ag	Combinations of a pi3k inhibitor and a mek inhibitor
WO2011130654A1 (en)	2010-04-16	2011-10-20	Genentech, Inc.	Fox03a as predictive biomarker for pi3k/akt kinase pathway inhibitor efficacy
US20140004209A1 (en)	2010-12-22	2014-01-02	Genentech, Inc.	Autophagy inducer and inhibitor combination therapy for the treatment of neoplasms
EP2959014B1 (en)	2013-02-25	2019-11-13	Genentech, Inc.	Methods and compositions for detecting and treating drug resistant akt mutant

0
- BE BE759493D patent/BE759493A/xx unknown
1970
- 1970-11-17 BG BG017732A patent/BG17800A3/xx unknown
- 1970-11-17 BG BG016080A patent/BG17799A3/xx unknown
- 1970-11-18 US US90841A patent/US3661908A/en not_active Expired - Lifetime
- 1970-11-23 CH CH1731270A patent/CH559210A5/xx not_active IP Right Cessation
- 1970-11-23 CH CH1514974A patent/CH568324A5/xx not_active IP Right Cessation
- 1970-11-23 CH CH1514674A patent/CH567029A5/xx not_active IP Right Cessation
- 1970-11-25 NO NO04524/70A patent/NO129954B/no unknown
- 1970-11-25 NL NL7017210A patent/NL7017210A/xx unknown
- 1970-11-25 DK DK601570AA patent/DK128781B/da unknown
- 1970-11-25 GB GB5614670A patent/GB1321316A/en not_active Expired
- 1970-11-26 IE IE1519/70A patent/IE34765B1/xx unknown
- 1970-11-26 CA CA099166A patent/CA926865A/en not_active Expired
- 1970-11-26 SE SE7016054A patent/SE377938B/xx unknown
- 1970-11-26 IL IL35729A patent/IL35729A/xx unknown
- 1970-11-26 FR FR7042531A patent/FR2073416B1/fr not_active Expired

Also Published As

Publication number	Publication date
CH559210A5 (ja)	1975-02-28
BE759493A (fr)	1971-05-25
CH568324A5 (ja)	1975-10-31
IE34765B1 (en)	1975-08-06
FR2073416A1 (ja)	1971-10-01
NL7017210A (ja)	1971-05-28
CA926865A (en)	1973-05-22
DK128781B (da)	1974-07-01
GB1321316A (en)	1973-06-27
BG17799A3 (bg)	1973-12-25
BG17800A3 (bg)	1973-12-25
FR2073416B1 (ja)	1975-04-18
US3661908A (en)	1972-05-09
IL35729A (en)	1974-01-14
IE34765L (en)	1971-05-26
IL35729A0 (en)	1971-01-28
CH567029A5 (ja)	1975-09-30
SE377938B (ja)	1975-08-04

Publication	Publication Date	Title
NO129954B (ja)	1974-06-17
RU2129549C1 (ru)	1999-04-27	Производные пиримидина и способы их получения
US20190194145A1 (en)	2019-06-27	Amino quinazolines as kinase inhibitors
DE69905264T2 (de)	2003-12-11	Chinolin- und chinazolin derivate und ihre verwendung als inhibitoren von krankheiten, bei denen cytokine beteiligt wird
CA2036618C (en)	2002-10-29	Fused thiophene derivatives, their production and use
CA2647036C (en)	2015-06-23	Tetrahydropyridothienopyrimidine compounds and methods of use thereof
US20080311076A1 (en)	2008-12-18	Morpholinylanilinoquinazoline Derivatives For Use As Antiviral Agents
HU188762B (en)	1986-05-28	Process for the preparation of 2,4-diamino-5-bracket-substituted-bracket closed-pyrimidines
ES2389907T9 (es)	2013-02-18	Compuesto de amida heterocíclica y uso del mismo como un inhibidor de MMP-13
CA2802641A1 (en)	2012-01-19	Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators
CZ300832B6 (cs)	2009-08-19	Bicyklické heteroaromatické slouceniny
JP2002527434A (ja)	2002-08-27	キノリン誘導体および抗菌剤としてその使用
HU192152B (en)	1987-05-28	Process for preparing new imidazole derivatives
AU748749B2 (en)	2002-06-13	Isoquinolones
UA54449C2 (uk)	2003-03-17	3-заміщені похідні піридо[4',3':4,5]тієно[2,3-d]піримідину
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