NL8302863A - Nieuwe tetrazinederivaten. - Google Patents

Nieuwe tetrazinederivaten. Download PDF

Info

Publication number: NL8302863A
Authority: NL; Netherlands
Prior art keywords: group; optionally substituted; solution; carbon atoms; substituted phenyl
Prior art date: 1982-08-17

Application number

NL8302863A

Other languages

English (en)

Dutch (nl)

Original Assignee

May & Baker Ltd

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.)

1982-08-17

Filing date

1983-08-15

Publication date

1984-03-16

1983-03-14 Priority claimed from GB838306904A external-priority patent/GB8306904D0/en

1983-08-15 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1984-03-16 Publication of NL8302863A publication Critical patent/NL8302863A/nl

Links

150000004905 tetrazines Chemical class 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims description 51
-1 hy droxy Chemical group 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 27
238000000034 method Methods 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 15
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
238000000576 coating method Methods 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
241001331845 Equus asinus x caballus Species 0.000 claims 1
125000005236 alkanoylamino group Chemical group 0.000 claims 1
125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
150000002823 nitrates Chemical class 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 237
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 149
239000000243 solution Substances 0.000 description 128
239000000203 mixture Substances 0.000 description 106
239000007787 solid Substances 0.000 description 93
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 52
238000000354 decomposition reaction Methods 0.000 description 44
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 42
238000000921 elemental analysis Methods 0.000 description 40
239000000460 chlorine Substances 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 21
235000010288 sodium nitrite Nutrition 0.000 description 21
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 20
239000003208 petroleum Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical class CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
239000000047 product Substances 0.000 description 14
239000013078 crystal Substances 0.000 description 13
239000000284 extract Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000000725 suspension Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000003054 catalyst Substances 0.000 description 6
239000007789 gas Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
229940124530 sulfonamide Drugs 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
230000037396 body weight Effects 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000007911 parenteral administration Methods 0.000 description 5
239000008247 solid mixture Substances 0.000 description 5
150000003456 sulfonamides Chemical class 0.000 description 5
FJKXXVLRHNIFOT-UHFFFAOYSA-N 1h-1,2,3,5-tetrazin-6-one Chemical compound O=C1N=CN=NN1 FJKXXVLRHNIFOT-UHFFFAOYSA-N 0.000 description 4
DXVWMLQMDGMWEQ-UHFFFAOYSA-N 1h-imidazo[5,1-d][1,2,3,5]tetrazin-4-one Chemical compound O=C1NN=NC2=CN=CN12 DXVWMLQMDGMWEQ-UHFFFAOYSA-N 0.000 description 4
VIRWKAJWTKAIMA-UHFFFAOYSA-N 2-chloroethyl acetate Chemical compound CC(=O)OCCCl VIRWKAJWTKAIMA-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
229940075930 picrate Drugs 0.000 description 4
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
KQHHAYJVMXDMHI-UHFFFAOYSA-N 2-methyl-4-nitro-1h-imidazole-5-sulfonyl chloride Chemical compound CC1=NC([N+]([O-])=O)=C(S(Cl)(=O)=O)N1 KQHHAYJVMXDMHI-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000006978 adaptation Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000007788 liquid Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 2
JRWAUKYINYWSTA-UHFFFAOYSA-N 2-amino-2-cyanoacetamide Chemical compound N#CC(N)C(N)=O JRWAUKYINYWSTA-UHFFFAOYSA-N 0.000 description 2
FPJOCIZOSGXPGL-UHFFFAOYSA-N 2-butyl-5-diazoimidazole-4-carboxamide Chemical compound C(CCC)C1=NC(C(=N1)C(=O)N)=[N+]=[N-] FPJOCIZOSGXPGL-UHFFFAOYSA-N 0.000 description 2
CINPESGJDJJVKV-UHFFFAOYSA-N 3-(2-chloroethyl)-6-methyl-8-propylsulfonylimidazo[5,1-d][1,2,3,5]tetrazin-4-one Chemical compound ClCCN1N=NC=2N(C1=O)C(=NC2S(=O)(=O)CCC)C CINPESGJDJJVKV-UHFFFAOYSA-N 0.000 description 2
WARGTDKANSDREC-UHFFFAOYSA-N 4-amino-N,N,2-trimethyl-1H-imidazole-5-sulfonamide Chemical compound NC1=C(N=C(N1)C)S(N(C)C)(=O)=O WARGTDKANSDREC-UHFFFAOYSA-N 0.000 description 2
HQQOOAOVOVCGGM-UHFFFAOYSA-N 4-diazo-2-methyl-5-methylsulfonylimidazole Chemical compound CC1=NC(=[N+]=[N-])C(S(C)(=O)=O)=N1 HQQOOAOVOVCGGM-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
RBYLRHFFJUGSNT-UHFFFAOYSA-N Cl.NC1=C(N=C(N1)C)S(=O)(=O)C Chemical compound Cl.NC1=C(N=C(N1)C)S(=O)(=O)C RBYLRHFFJUGSNT-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
206010025323 Lymphomas Diseases 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003708 ampul Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000002027 dichloromethane extract Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000011521 glass Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
201000001441 melanoma Diseases 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000006396 nitration reaction Methods 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000000312 peanut oil Substances 0.000 description 2
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000001665 trituration Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
CQRBGSZZSKJPCU-UHFFFAOYSA-N (4-amino-1h-imidazol-5-yl)-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.N1=CNC(C(=O)N2CCCCC2)=C1N CQRBGSZZSKJPCU-UHFFFAOYSA-N 0.000 description 1
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MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000008016 pharmaceutical coating Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
208000029922 reticulum cell sarcoma Diseases 0.000 description 1
238000012552 review Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- 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
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NL8302863A 1982-08-17 1983-08-15 Nieuwe tetrazinederivaten. NL8302863A (nl)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
GB8223583		1982-08-17
GB8223580		1982-08-17
GB8223580		1982-08-17
GB8223583		1982-08-17
GB8226169		1982-09-14
GB8226169		1982-09-14
GB8306904		1983-03-14
GB838306904A GB8306904D0 (en)	1983-03-14	1983-03-14	Compositions of matter

Publications (1)

Publication Number	Publication Date
NL8302863A true NL8302863A (nl)	1984-03-16

Family

ID=27449377

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8302863A NL8302863A (nl)	1982-08-17	1983-08-15	Nieuwe tetrazinederivaten.

Country Status (18)

Country	Link
AU (1)	AU575782B2 (sv)
BE (1)	BE897548A (sv)
CA (1)	CA1254563A (sv)
CH (1)	CH657855A5 (sv)
DE (1)	DE3329505A1 (sv)
DK (1)	DK374983A (sv)
ES (1)	ES524995A0 (sv)
FI (1)	FI80273C (sv)
FR (1)	FR2531958B1 (sv)
GR (1)	GR78688B (sv)
HU (1)	HU189321B (sv)
IE (1)	IE55849B1 (sv)
IL (1)	IL69500A (sv)
IT (1)	IT1194375B (sv)
LU (1)	LU84969A1 (sv)
NL (1)	NL8302863A (sv)
NZ (1)	NZ205272A (sv)
SE (1)	SE455198B (sv)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2932305A1 (de) *	1979-08-09	1981-02-26	Basf Ag	Azolo- eckige klammer auf 5,1-d eckige klammer zu - eckige klammer auf 1,2,3,5 eckige klammer zu -tetrazin-4-one und verfahren zur herstellung dieser verbindungen
OA07174A (fr) *	1981-08-24	1984-04-30	May & Baker Ltd	Nouvelles imidazotétrazionones, leur préparation et les médicaments qui les contiennent.

1983
- 1983-08-12 FR FR8313246A patent/FR2531958B1/fr not_active Expired
- 1983-08-12 GR GR72210A patent/GR78688B/el unknown
- 1983-08-15 NZ NZ205272A patent/NZ205272A/en unknown
- 1983-08-15 IL IL69500A patent/IL69500A/xx unknown
- 1983-08-15 HU HU832860A patent/HU189321B/hu unknown
- 1983-08-15 AU AU17968/83A patent/AU575782B2/en not_active Ceased
- 1983-08-15 CA CA000434582A patent/CA1254563A/en not_active Expired
- 1983-08-15 IE IE1913/83A patent/IE55849B1/xx unknown
- 1983-08-15 SE SE8304415A patent/SE455198B/sv not_active IP Right Cessation
- 1983-08-15 FI FI832927A patent/FI80273C/sv not_active IP Right Cessation
- 1983-08-15 NL NL8302863A patent/NL8302863A/nl not_active Application Discontinuation
- 1983-08-16 LU LU84969A patent/LU84969A1/fr unknown
- 1983-08-16 DK DK374983A patent/DK374983A/da not_active Application Discontinuation
- 1983-08-16 IT IT22566/83A patent/IT1194375B/it active
- 1983-08-16 DE DE3329505A patent/DE3329505A1/de not_active Withdrawn
- 1983-08-17 BE BE0/211366A patent/BE897548A/fr not_active IP Right Cessation
- 1983-08-17 ES ES83524995A patent/ES524995A0/es active Granted
- 1983-08-17 CH CH4490/83A patent/CH657855A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE897548A (fr)	1984-02-17
ES8502441A1 (es)	1985-01-01
IL69500A (en)	1989-01-31
LU84969A1 (fr)	1984-03-23
FR2531958B1 (fr)	1986-10-31
NZ205272A (en)	1986-12-05
FI832927A0 (fi)	1983-08-15
CA1254563A (en)	1989-05-23
FI80273B (fi)	1990-01-31
AU575782B2 (en)	1988-08-11
HU189321B (en)	1986-06-30
IT1194375B (it)	1988-09-22
IT8322566A0 (it)	1983-08-16
CH657855A5 (fr)	1986-09-30
AU1796883A (en)	1984-02-23
SE8304415L (sv)	1984-02-18
GR78688B (sv)	1984-09-27
FR2531958A1 (fr)	1984-02-24
DK374983A (da)	1984-02-18
FI80273C (sv)	1990-05-10
IE831913L (en)	1984-02-17
SE455198B (sv)	1988-06-27
SE8304415D0 (sv)	1983-08-15
DK374983D0 (da)	1983-08-16
ES524995A0 (es)	1985-01-01
DE3329505A1 (de)	1984-02-23
IE55849B1 (en)	1991-01-30
FI832927A (fi)	1984-02-18

Publication	Publication Date	Title
US5260291A (en)	1993-11-09	Tetrazine derivatives
US4438128A (en)	1984-03-20	Cardioactive aryloxypropanolamines
FI73434B (fi)	1987-06-30	Foerfarande foer framstaellning av /3h/-imidazo-/5,1-d/-1,2,3,5-tetrazin-4-onderivat med terapeutisk verkan.
DE4019892A1 (de)	1992-01-02	Neue xanthinderivate
KR20030013475A (ko)	2003-02-14	항암제로서의 치환된 트리아졸로피리미딘
EP0370236B1 (de)	1991-12-27	Indolocarbazol-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
EP0252682A2 (en)	1988-01-13	Tetrazines
GB2125402A (en)	1984-03-07	New tetrazine derivatives
NL8302863A (nl)	1984-03-16	Nieuwe tetrazinederivaten.
US3234217A (en)	1966-02-08	Pyrazole carboxylic acid hydrazides
Attanasi et al.	1999	Study of reactions between 1, 2-diaza-1, 3-butadienes and N, N′-diaryl-or N, N′-dialkylthioureas
Davis et al.	1969	Synthesis of substituted 2, 1-benzisothiazoles
EP2740727B1 (en)	2014-10-22	Quinazolinone analogues for use as anticonvulsant agents
EP1200439B1 (en)	2003-06-25	1,2-dihydro-1-oxo-parazino(1,2-a) indole derivatives
NO177749B (no)	1995-08-07	Analogifremgangsmåte ved fremstilling av 2,4,8-tri-substituerte 3H,6H-1,4,5a,8a-tetraazaace-naftylen-3,5-(4H)-dioner
NL8002120A (nl)	1980-10-14	Nieuwe benzo-as-triazinederivaten en werkwijze voor de bereiding van deze verbindingen.
Pilgram et al.	1983	Synthesis of 1‐aryl‐3‐trifluoromethyl‐5‐methylthio‐1, 2, 4‐triazoles from 2‐arylmethylisothiosemicarbazides and 1, 1, 1‐trichloro‐3, 3, 3‐trifluoroacetone
EP2592085B1 (en)	2016-07-27	Thiazolo[3,2-a][1,3]diazepine derivatives and pharmaceutical compositions containing the same as anticonvulsant agents and method for their preparation
AU8554098A (en)	1999-02-22	New 2,3-benzodiazepine derivatives
El-Ablack	2011	Synthesis of some new benzimidazole derivatives of pharmaceutical interest
CH622517A5 (en)	1981-04-15	Process for the preparation of 6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepine and 4,5-dihydro-7-phenyl-s-triazolo- [4,3-a][1,5]benzodiazocines
Nguyen et al.	2020	Synthesis and bioevaluation of some new N-substituted pyranophenothiazines
HU203554B (en)	1991-08-28	Process for producing 5-amino-8-(phenyl- or substituted phenyl)-3h, 6h-1,4,5a, 8a- - tetraaza-acenaphtylen-3-ones and pharmaceutical compositions containing them
US4550110A (en)	1985-10-29	6-(1,8-Naphthyridin-2-yl)-dithiino[1,4][2,3-c]-pyrroles useful as tranquillizers and anticonvulsants
Lee et al.	2019	Auckland Cancer Society Research Centre, School of Medical Sciences, Faculty of Medical and Health Sciences, The University of Auckland, Private Bag 92019, Auckland 1142, New Zealand

Legal Events

Date	Code	Title
1984-06-01	BT	A notification was added to the application dossier and made available to the public
1985-01-01	A85	Still pending on 85-01-01
1985-01-02	BT	A notification was added to the application dossier and made available to the public
1990-10-01	BV	The patent application has lapsed