BE594515A - - Google Patents
Info
- Publication number
- BE594515A BE594515A BE594515DA BE594515A BE 594515 A BE594515 A BE 594515A BE 594515D A BE594515D A BE 594515DA BE 594515 A BE594515 A BE 594515A
- Authority
- BE
- Belgium
- Prior art keywords
- pyrimidopyrimidine
- bis
- pyrimido
- reaction
- substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 25
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical class N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims description 24
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 21
- -1 amino, thio, guanidino Chemical group 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000001879 copper Chemical class 0.000 claims description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 239000002516 radical scavenger Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
- 150000003230 pyrimidines Chemical group 0.000 claims description 3
- 125000004149 thio group Chemical group *S* 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- QESGMHIAKOFWIM-UHFFFAOYSA-N 4-(4-morpholin-4-ylpyrimido[5,4-d]pyrimidin-8-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C(N3CCOCC3)N=CN=C12 QESGMHIAKOFWIM-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 238000004458 analytical method Methods 0.000 description 44
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004364 calculation method Methods 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 15
- QNKFHUMDHRWWES-UHFFFAOYSA-N 2,4,6,8-tetrachloropyrimido[5,4-d]pyrimidine Chemical compound N1=C(Cl)N=C(Cl)C2=NC(Cl)=NC(Cl)=C21 QNKFHUMDHRWWES-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 238000001556 precipitation Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 10
- AQHKGPWUIOAPHJ-UHFFFAOYSA-N 2,4,8-trichloropyrimido[5,4-d]pyrimidine Chemical compound N1=CN=C(Cl)C2=NC(Cl)=NC(Cl)=C21 AQHKGPWUIOAPHJ-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000020477 pH reduction Effects 0.000 description 6
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000002526 effect on cardiovascular system Effects 0.000 description 4
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
- YHDMWGVBXYRWBZ-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine-2,4,6,8-tetramine Chemical class N1=C(N)N=C(N)C2=NC(N)=NC(N)=C21 YHDMWGVBXYRWBZ-UHFFFAOYSA-N 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- GXHYRYPQIXBOIU-UHFFFAOYSA-N 2,6-dichloro-4-n,8-n-diphenylpyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound C=12N=C(Cl)N=C(NC=3C=CC=CC=3)C2=NC(Cl)=NC=1NC1=CC=CC=C1 GXHYRYPQIXBOIU-UHFFFAOYSA-N 0.000 description 3
- NWCMUXXOBVJKPH-UHFFFAOYSA-N 4-(2-chloro-4-morpholin-4-ylpyrimido[5,4-d]pyrimidin-8-yl)morpholine Chemical compound C=12N=CN=C(N3CCOCC3)C2=NC(Cl)=NC=1N1CCOCC1 NWCMUXXOBVJKPH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- RLJCWYYOGHGGBV-UHFFFAOYSA-N 1h-pyrimido[5,4-d]pyrimidin-2-one Chemical compound C1=NC=C2NC(=O)N=CC2=N1 RLJCWYYOGHGGBV-UHFFFAOYSA-N 0.000 description 2
- YIQIENHQATXFFQ-UHFFFAOYSA-N 2,6-dichloro-1,5-dihydropyrimido[5,4-d]pyrimidine-4,8-dione Chemical compound N1C(Cl)=NC(=O)C2=C1C(=O)N=C(Cl)N2 YIQIENHQATXFFQ-UHFFFAOYSA-N 0.000 description 2
- KGZWXSSCVVGOSD-UHFFFAOYSA-N 2-chloro-4,8-diiodopyrimido[5,4-d]pyrimidine Chemical compound N1=CN=C(I)C2=NC(Cl)=NC(I)=C21 KGZWXSSCVVGOSD-UHFFFAOYSA-N 0.000 description 2
- APPWIIPTZNUJBU-UHFFFAOYSA-N 2-chloropyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound N1=C(Cl)N=C2C(N)=NC=NC2=C1N APPWIIPTZNUJBU-UHFFFAOYSA-N 0.000 description 2
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 2
- DQJRFVLACBXETO-UHFFFAOYSA-N 4,8-dichloropyrimido[5,4-d]pyrimidine Chemical compound N1=CN=C2C(Cl)=NC=NC2=C1Cl DQJRFVLACBXETO-UHFFFAOYSA-N 0.000 description 2
- FKXDINDRYHXKIH-UHFFFAOYSA-N 4-[4,8-bis(ethylsulfanyl)-2-morpholin-4-ylpyrimido[5,4-d]pyrimidin-6-yl]morpholine Chemical compound O1CCN(CC1)C1=NC2=C(C(=N1)SCC)N=C(N=C2SCC)N2CCOCC2 FKXDINDRYHXKIH-UHFFFAOYSA-N 0.000 description 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- MOHYTMXQKJHDJC-UHFFFAOYSA-N ClC1=NC2=C(C(=N1)SCC(=O)O)N=CN=C2SCC(=O)O Chemical compound ClC1=NC2=C(C(=N1)SCC(=O)O)N=CN=C2SCC(=O)O MOHYTMXQKJHDJC-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000010339 dilation Effects 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- IPVYZURURLFDKK-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine-2,4,8-triamine Chemical class N1=CN=C(N)C2=NC(N)=NC(N)=C21 IPVYZURURLFDKK-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ROZIEFCJIDEZFF-UHFFFAOYSA-N 1,5-dihydropyrimido[5,4-d]pyrimidine-4,6,8-trione Chemical compound N1C(=O)NC(=O)C2=C1C(=O)N=CN2 ROZIEFCJIDEZFF-UHFFFAOYSA-N 0.000 description 1
- QAGDGAGJUTYJRT-UHFFFAOYSA-N 1,5-dihydropyrimido[5,4-d]pyrimidine-4,8-dione Chemical compound N1=CN=C2C(O)=NC=NC2=C1O QAGDGAGJUTYJRT-UHFFFAOYSA-N 0.000 description 1
- HSXXGOONRBHEGY-UHFFFAOYSA-N 2,4,6,8-tetra(piperidin-1-yl)pyrimido[5,4-d]pyrimidine Chemical compound C1CCCCN1C1=NC(N2CCCCC2)=C(N=C(N=C2N3CCCCC3)N3CCCCC3)C2=N1 HSXXGOONRBHEGY-UHFFFAOYSA-N 0.000 description 1
- OYLDTFHRNFUECR-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethylsulfanyl)pyrimido[5,4-d]pyrimidine Chemical compound N1=C(SCC)N=C(SCC)C2=NC(SCC)=NC(SCC)=C21 OYLDTFHRNFUECR-UHFFFAOYSA-N 0.000 description 1
- RVXYPQSMPASFQA-UHFFFAOYSA-N 2,4,8-trimethoxypyrimido[5,4-d]pyrimidine Chemical compound N1=CN=C(OC)C2=NC(OC)=NC(OC)=C21 RVXYPQSMPASFQA-UHFFFAOYSA-N 0.000 description 1
- IBEUJZWNKFMKAG-UHFFFAOYSA-N 2,4-dichloropyrimido[5,4-d]pyrimidine Chemical compound ClC=1N=C(C2=C(C=NC=N2)N1)Cl IBEUJZWNKFMKAG-UHFFFAOYSA-N 0.000 description 1
- QWKAKGBCOHHLEK-UHFFFAOYSA-N 2,6-dichloro-4,8-bis(ethylsulfanyl)pyrimido[5,4-d]pyrimidine Chemical compound N1=C(Cl)N=C2C(SCC)=NC(Cl)=NC2=C1SCC QWKAKGBCOHHLEK-UHFFFAOYSA-N 0.000 description 1
- QOLRNNDNGCLHCI-UHFFFAOYSA-N 2,6-dichloro-4,8-bis(phenylsulfanyl)pyrimido[5,4-d]pyrimidine Chemical compound ClC=1N=C(C2=C(C(=NC(=N2)Cl)SC2=CC=CC=C2)N1)SC1=CC=CC=C1 QOLRNNDNGCLHCI-UHFFFAOYSA-N 0.000 description 1
- DSVZJKGRQXXOPV-UHFFFAOYSA-N 2,6-dichloro-4,8-diiodopyrimido[5,4-d]pyrimidine Chemical compound N1=C(Cl)N=C(I)C2=NC(Cl)=NC(I)=C21 DSVZJKGRQXXOPV-UHFFFAOYSA-N 0.000 description 1
- WAACIRULZQBPGV-UHFFFAOYSA-N 2,6-dichloro-4-n,4-n,8-n,8-n-tetraethylpyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound N1=C(Cl)N=C2C(N(CC)CC)=NC(Cl)=NC2=C1N(CC)CC WAACIRULZQBPGV-UHFFFAOYSA-N 0.000 description 1
- GOICHZCHZGBOTH-UHFFFAOYSA-N 2,6-dichloropyrimido[5,4-d]pyrimidine-4,8-diamine Chemical class N1=C(Cl)N=C2C(N)=NC(Cl)=NC2=C1N GOICHZCHZGBOTH-UHFFFAOYSA-N 0.000 description 1
- HJYGFQOCTKTDFL-UHFFFAOYSA-N 2-[8-(carboxymethylsulfanyl)-2-morpholin-4-ylpyrimido[5,4-d]pyrimidin-4-yl]sulfanylacetic acid Chemical compound O1CCN(CC1)C1=NC2=C(C(=N1)SCC(=O)O)N=CN=C2SCC(=O)O HJYGFQOCTKTDFL-UHFFFAOYSA-N 0.000 description 1
- PQLXJCRFZCRBNF-UHFFFAOYSA-N 2-anilinoethanol;hydrochloride Chemical compound Cl.OCCNC1=CC=CC=C1 PQLXJCRFZCRBNF-UHFFFAOYSA-N 0.000 description 1
- DWUDAQDTWOQOFL-UHFFFAOYSA-N 2-chloropyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC(Cl)=NC=C21 DWUDAQDTWOQOFL-UHFFFAOYSA-N 0.000 description 1
- ZNNRXVZVISQOMW-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,8-n,8-n-hexamethylpyrimido[5,4-d]pyrimidine-2,4,8-triamine Chemical compound N1=CN=C(N(C)C)C2=NC(N(C)C)=NC(N(C)C)=C21 ZNNRXVZVISQOMW-UHFFFAOYSA-N 0.000 description 1
- GNLHJUBMOPTPPZ-UHFFFAOYSA-N 2-n,4-n,8-n-trimethylpyrimido[5,4-d]pyrimidine-2,4,8-triamine Chemical compound N1=CN=C(NC)C2=NC(NC)=NC(NC)=C21 GNLHJUBMOPTPPZ-UHFFFAOYSA-N 0.000 description 1
- PPLDWBXWLMOULZ-UHFFFAOYSA-N 2-n,4-n,8-n-tris(4-chlorophenyl)pyrimido[5,4-d]pyrimidine-2,4,8-triamine Chemical compound C1=CC(Cl)=CC=C1NC1=NC(NC=2C=CC(Cl)=CC=2)=C(N=CN=C2NC=3C=CC(Cl)=CC=3)C2=N1 PPLDWBXWLMOULZ-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- NYLRLVUDYUCHPD-UHFFFAOYSA-N 4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine Chemical compound C1CCCCN1C1=NC=NC2=C(N3CCCCC3)N=CN=C12 NYLRLVUDYUCHPD-UHFFFAOYSA-N 0.000 description 1
- JWVYTWMDTCDKSU-UHFFFAOYSA-N 4-(2,4-dimorpholin-4-ylpyrimido[5,4-d]pyrimidin-8-yl)morpholine Chemical compound C1COCCN1C1=NC(N2CCOCC2)=C(N=CN=C2N3CCOCC3)C2=N1 JWVYTWMDTCDKSU-UHFFFAOYSA-N 0.000 description 1
- CKEDESQLMAKPDI-UHFFFAOYSA-N 4-(2,6-dichloro-4-morpholin-4-ylpyrimido[5,4-d]pyrimidin-8-yl)morpholine Chemical compound C=12N=C(Cl)N=C(N3CCOCC3)C2=NC(Cl)=NC=1N1CCOCC1 CKEDESQLMAKPDI-UHFFFAOYSA-N 0.000 description 1
- USNAZCONQRIFLH-UHFFFAOYSA-N 4-n,4-n,8-n,8-n-tetrabenzyl-2-chloropyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound C=12N=CN=C(N(CC=3C=CC=CC=3)CC=3C=CC=CC=3)C2=NC(Cl)=NC=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 USNAZCONQRIFLH-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- RXZROPFOOJMIMQ-UHFFFAOYSA-N 6-(imidazol-1-ylmethyl)-2-n,2-n-dimethyl-1,3,5-triazine-2,4-diamine Chemical compound CN(C)C1=NC(N)=NC(CN2C=NC=C2)=N1 RXZROPFOOJMIMQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- HHAKMKCJPHXCLI-UHFFFAOYSA-N CCCNC1=NC=NC(C(NCCC)=N2)=C1N=C2Cl Chemical compound CCCNC1=NC=NC(C(NCCC)=N2)=C1N=C2Cl HHAKMKCJPHXCLI-UHFFFAOYSA-N 0.000 description 1
- LBFABLHSUMYNRM-UHFFFAOYSA-N CSC1=NC2=C(C=N1)N=C(N=C2Cl)Cl Chemical compound CSC1=NC2=C(C=N1)N=C(N=C2Cl)Cl LBFABLHSUMYNRM-UHFFFAOYSA-N 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VSGZWJLLGFHYGJ-UHFFFAOYSA-N N,N-diethylpyrimido[5,4-d]pyrimidin-2-amine Chemical compound C(C)N(CC)C=1N=CC2=C(N1)C=NC=N2 VSGZWJLLGFHYGJ-UHFFFAOYSA-N 0.000 description 1
- IKDBMUOMPJCCSV-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1N=C(C2=C(C(=NC(=N2)OC2=CC=CC=C2)OC2=CC=CC=C2)N1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)C=1N=C(C2=C(C(=NC(=N2)OC2=CC=CC=C2)OC2=CC=CC=C2)N1)OC1=CC=CC=C1 IKDBMUOMPJCCSV-UHFFFAOYSA-N 0.000 description 1
- ZNASAPFKAOUIHW-UHFFFAOYSA-N OC(CSC(N=C1Cl)=NC(C(Cl)=N2)=C1N=C2Cl)=O Chemical compound OC(CSC(N=C1Cl)=NC(C(Cl)=N2)=C1N=C2Cl)=O ZNASAPFKAOUIHW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000287219 Serinus canaria Species 0.000 description 1
- OBEKNAJMUZXECI-UHFFFAOYSA-N [[4-(2-carbamoylhydrazinyl)-2-chloropyrimido[5,4-d]pyrimidin-8-yl]amino]urea Chemical compound N1=C(Cl)N=C2C(NNC(=O)N)=NC=NC2=C1NNC(N)=O OBEKNAJMUZXECI-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical class OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
- LQYCIOQCKLIHES-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidin-2-amine Chemical class N1=CN=CC2=NC(N)=NC=C21 LQYCIOQCKLIHES-UHFFFAOYSA-N 0.000 description 1
- NFHMDRANESJFQS-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine-2,4-diamine Chemical class N1=CN=CC2=NC(N)=NC(N)=C21 NFHMDRANESJFQS-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE594515A true BE594515A (enrdf_load_stackoverflow) |
Family
ID=192163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE594515D BE594515A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE594515A (enrdf_load_stackoverflow) |
-
0
- BE BE594515D patent/BE594515A/fr unknown
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