NO130376B - - Google Patents
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- Publication number
- NO130376B NO130376B NO34572A NO34572A NO130376B NO 130376 B NO130376 B NO 130376B NO 34572 A NO34572 A NO 34572A NO 34572 A NO34572 A NO 34572A NO 130376 B NO130376 B NO 130376B
- Authority
- NO
- Norway
- Prior art keywords
- pyrimidopyrimidine
- pyrimido
- pyrimidine
- dichloro
- aralkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 34
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical class N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical group CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical group CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- -1 di-substituted amino group Chemical group 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 14
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 12
- GOICHZCHZGBOTH-UHFFFAOYSA-N 2,6-dichloropyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound N1=C(Cl)N=C2C(N)=NC(Cl)=NC2=C1N GOICHZCHZGBOTH-UHFFFAOYSA-N 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 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 11
- 239000011541 reaction mixture Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-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
- 238000001816 cooling Methods 0.000 description 9
- 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 8
- 238000009835 boiling Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 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 7
- 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 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 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
- KYFPNDYCOOLGEP-UHFFFAOYSA-N 2-n,4-n,6-n,8-n-tetraphenylpyrimido[5,4-d]pyrimidine-2,4,6,8-tetramine Chemical compound N=1C(NC=2C=CC=CC=2)=C2N=C(NC=3C=CC=CC=3)N=C(NC=3C=CC=CC=3)C2=NC=1NC1=CC=CC=C1 KYFPNDYCOOLGEP-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- PCVJQTVUJJJSRQ-UHFFFAOYSA-N 2,6-dichloro-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine Chemical compound C=12N=C(Cl)N=C(N3CCCCC3)C2=NC(Cl)=NC=1N1CCCCC1 PCVJQTVUJJJSRQ-UHFFFAOYSA-N 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 4
- APPWIIPTZNUJBU-UHFFFAOYSA-N 2-chloropyrimido[5,4-d]pyrimidine-4,8-diamine Chemical class N1=C(Cl)N=C2C(N)=NC=NC2=C1N APPWIIPTZNUJBU-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- GSAUINCNYXKDSU-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine-4,8-diamine Chemical class N1=CN=C2C(N)=NC=NC2=C1N GSAUINCNYXKDSU-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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 3
- VEOXKAUOVJAALX-UHFFFAOYSA-N 2-n,4-n,8-n-triphenylpyrimido[5,4-d]pyrimidine-2,4,8-triamine Chemical compound N=1C(NC=2C=CC=CC=2)=C2N=CN=C(NC=3C=CC=CC=3)C2=NC=1NC1=CC=CC=C1 VEOXKAUOVJAALX-UHFFFAOYSA-N 0.000 description 3
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 3
- 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 3
- YFVBRCUNIZVJDX-UHFFFAOYSA-N 4-n,8-n-diphenylpyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound N=1C=NC2=C(NC=3C=CC=CC=3)N=CN=C2C=1NC1=CC=CC=C1 YFVBRCUNIZVJDX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001879 copper Chemical class 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
- 239000003085 diluting agent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005245 sintering Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- 125000004149 thio group Chemical group *S* 0.000 description 3
- 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 2
- VYUJIRSYASRUJK-UHFFFAOYSA-N 2,6-dichloro-4,8-diethoxypyrimido[5,4-d]pyrimidine Chemical compound ClC=1N=C(C2=C(C(=NC(=N2)Cl)OCC)N1)OCC VYUJIRSYASRUJK-UHFFFAOYSA-N 0.000 description 2
- BUIQHLZKVOZIFV-UHFFFAOYSA-N 2-n,4-n,6-n,8-n-tetramethylpyrimido[5,4-d]pyrimidine-2,4,6,8-tetramine Chemical compound N1=C(NC)N=C(NC)C2=NC(NC)=NC(NC)=C21 BUIQHLZKVOZIFV-UHFFFAOYSA-N 0.000 description 2
- PEXHOHAPBLUWNN-UHFFFAOYSA-N 2-n,4-n,8-n-tris(2-methoxyphenyl)pyrimido[5,4-d]pyrimidine-2,4,8-triamine Chemical compound COC1=CC=CC=C1NC1=NC(NC=2C(=CC=CC=2)OC)=C(N=CN=C2NC=3C(=CC=CC=3)OC)C2=N1 PEXHOHAPBLUWNN-UHFFFAOYSA-N 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
- VVTWTORETLAHIJ-UHFFFAOYSA-N 4-n,4-n,8-n,8-n-tetramethylpyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound N1=CN=C2C(N(C)C)=NC=NC2=C1N(C)C VVTWTORETLAHIJ-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
- JXPVNGYAUWESOK-UHFFFAOYSA-N CSC1=NC2=C(C=N1)N=C(N=C2N2CCOCC2)N2CCOCC2 Chemical compound CSC1=NC2=C(C=N1)N=C(N=C2N2CCOCC2)N2CCOCC2 JXPVNGYAUWESOK-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
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000005792 cardiovascular activity Effects 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OUIBBKLKVGOAFI-UHFFFAOYSA-N (8-hydrazinylpyrimido[5,4-d]pyrimidin-4-yl)hydrazine Chemical compound N1=CN=C2C(NN)=NC=NC2=C1NN OUIBBKLKVGOAFI-UHFFFAOYSA-N 0.000 description 1
- HBGALFVDRUBTCE-UHFFFAOYSA-N 1,2-dichloroethane;propan-2-one Chemical compound CC(C)=O.ClCCCl HBGALFVDRUBTCE-UHFFFAOYSA-N 0.000 description 1
- GHJWRAHLDAFABX-UHFFFAOYSA-N 1,2-diphenyl-1-[4-(N-(N'-phenylcarbamimidoyl)anilino)pyrimido[5,4-d]pyrimidin-8-yl]guanidine Chemical compound C1(=CC=CC=C1)N(C(=NC1=CC=CC=C1)N)C1=NC=NC=2C(=NC=NC=21)N(C(=NC1=CC=CC=C1)N)C1=CC=CC=C1 GHJWRAHLDAFABX-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
- WVKLUOJGEBKRGA-UHFFFAOYSA-N 2,6-bis(4-methylpiperazin-1-yl)-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine Chemical compound CN1CCN(CC1)C=1N=C(C2=C(C(=NC(=N2)N2CCN(CC2)C)N2CCCCC2)N=1)N1CCCCC1 WVKLUOJGEBKRGA-UHFFFAOYSA-N 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-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
- 230000009467 reduction Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01P—MEASURING LINEAR OR ANGULAR SPEED, ACCELERATION, DECELERATION, OR SHOCK; INDICATING PRESENCE, ABSENCE, OR DIRECTION, OF MOVEMENT
- G01P5/00—Measuring speed of fluids, e.g. of air stream; Measuring speed of bodies relative to fluids, e.g. of ship, of aircraft
- G01P5/14—Measuring speed of fluids, e.g. of air stream; Measuring speed of bodies relative to fluids, e.g. of ship, of aircraft by measuring differences of pressure in the fluid
Landscapes
- Engineering & Computer Science (AREA)
- Aviation & Aerospace Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Measuring Fluid Pressure (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE173371A SE346624B (cs) | 1971-02-11 | 1971-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130376B true NO130376B (cs) | 1974-08-19 |
Family
ID=20258733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO34572A NO130376B (cs) | 1971-02-11 | 1972-02-08 |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE2206613A1 (cs) |
| FR (1) | FR2125397B1 (cs) |
| GB (1) | GB1376374A (cs) |
| NO (1) | NO130376B (cs) |
| SE (1) | SE346624B (cs) |
-
1971
- 1971-02-11 SE SE173371A patent/SE346624B/xx unknown
-
1972
- 1972-02-08 NO NO34572A patent/NO130376B/no unknown
- 1972-02-10 GB GB625372A patent/GB1376374A/en not_active Expired
- 1972-02-11 FR FR7204679A patent/FR2125397B1/fr not_active Expired
- 1972-02-11 DE DE19722206613 patent/DE2206613A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE346624B (cs) | 1972-07-10 |
| FR2125397B1 (cs) | 1975-02-14 |
| FR2125397A1 (cs) | 1972-09-29 |
| DE2206613A1 (de) | 1972-08-24 |
| GB1376374A (en) | 1974-12-04 |
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