BG62969B1 - Пиримидо/5,4-d/пиримидини, лекарствени средства,съдържащи тези съединения, тяхното приложение и метод за тяхното получаване - Google Patents

Info

Publication number

BG62969B1

BG62969B1 BG101289A BG10128997A BG62969B1 BG 62969 B1 BG62969 B1 BG 62969B1 BG 101289 A BG101289 A BG 101289A BG 10128997 A BG10128997 A BG 10128997A BG 62969 B1 BG62969 B1 BG 62969B1

Authority

BG

Bulgaria

Prior art keywords

group

amino

alkyl

substituted

atom

Prior art date

1994-09-07

Links

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• 238000002360 preparation method Methods 0.000 title claims abstract description 15
• 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 8
• 150000001875 compounds Chemical class 0.000 title claims description 97
• 238000000034 method Methods 0.000 title claims description 10
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 150000007524 organic acids Chemical class 0.000 claims abstract description 5
• 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
• 235000005985 organic acids Nutrition 0.000 claims abstract description 4
• -1 C 16 -alkyl Chemical group 0.000 claims description 726
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 303
• 125000000217 alkyl group Chemical group 0.000 claims description 283
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 189
• 125000004432 carbon atom Chemical group C* 0.000 claims description 159
• 125000003545 alkoxy group Chemical group 0.000 claims description 134
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 123
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 123
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 116
• 229910052757 nitrogen Inorganic materials 0.000 claims description 98
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 90
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
• 229910052760 oxygen Inorganic materials 0.000 claims description 72
• 125000003282 alkyl amino group Chemical group 0.000 claims description 70
• 239000001301 oxygen Substances 0.000 claims description 68
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 65
• 229910052717 sulfur Inorganic materials 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 125000004434 sulfur atom Chemical group 0.000 claims description 62
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 61
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 59
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 58
• 229910052801 chlorine Inorganic materials 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 55
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 239000001257 hydrogen Substances 0.000 claims description 52
• 239000000460 chlorine Substances 0.000 claims description 51
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 47
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 45
• 239000011737 fluorine Substances 0.000 claims description 45
• 229910052731 fluorine Inorganic materials 0.000 claims description 45
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 44
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 44
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 44
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 43
• 238000006243 chemical reaction Methods 0.000 claims description 42
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 125000004429 atom Chemical group 0.000 claims description 40
• 229910052799 carbon Inorganic materials 0.000 claims description 40
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 40
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 39
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 37
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 37
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 37
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 33
• 150000001721 carbon Chemical group 0.000 claims description 31
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 30
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 29
• 125000002947 alkylene group Chemical group 0.000 claims description 29
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 28
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 28
• 150000003254 radicals Chemical group 0.000 claims description 28
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 24
• 125000001153 fluoro group Chemical group F* 0.000 claims description 24
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 23
• 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 22
• 229910052740 iodine Inorganic materials 0.000 claims description 22
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 21
• 125000005277 alkyl imino group Chemical group 0.000 claims description 21
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 20
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 20
• 125000004104 aryloxy group Chemical group 0.000 claims description 19
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 18
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 17
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 16
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
• JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical class N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims description 16
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
• 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 14
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 14
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 13
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 13
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 10
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 9
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 230000003647 oxidation Effects 0.000 claims description 8
• 238000007254 oxidation reaction Methods 0.000 claims description 8
• 229920002554 vinyl polymer Polymers 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 7
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 7
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
• 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 6
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 6
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 230000035755 proliferation Effects 0.000 claims description 6
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 6
• 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 5
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 5
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 229920001774 Perfluoroether Polymers 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 4
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 125000005121 aminocarbonylalkoxy group Chemical group 0.000 claims description 4
• 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 4
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 125000000707 boryl group Chemical group B* 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 4
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 230000002159 abnormal effect Effects 0.000 claims description 3
• 230000010933 acylation Effects 0.000 claims description 3
• 238000005917 acylation reaction Methods 0.000 claims description 3
• 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims description 3
• 230000029936 alkylation Effects 0.000 claims description 3
• 238000005804 alkylation reaction Methods 0.000 claims description 3
• 230000009435 amidation Effects 0.000 claims description 3
• 238000007112 amidation reaction Methods 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 125000005122 aminoalkylamino group Chemical group 0.000 claims description 3
• 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 3
• 125000004467 aryl imino group Chemical group 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 3
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 238000005886 esterification reaction Methods 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 238000005932 reductive alkylation reaction Methods 0.000 claims description 3
• 238000006277 sulfonation reaction Methods 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• 206010027476 Metastases Diseases 0.000 claims description 2
• 206010029113 Neovascularisation Diseases 0.000 claims description 2
• 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 2
• 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 2
• 125000005237 alkyleneamino group Chemical group 0.000 claims description 2
• 125000005336 allyloxy group Chemical group 0.000 claims description 2
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 2
• 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 2
• 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
• 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
• 210000003556 vascular endothelial cell Anatomy 0.000 claims description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 3
• 239000003814 drug Substances 0.000 claims 3
• 239000001569 carbon dioxide Chemical group 0.000 claims 2
• 229910002092 carbon dioxide Inorganic materials 0.000 claims 2
• 241000907681 Morpho Species 0.000 claims 1
• HLOMTHGHDNSPAQ-UMSPYCQHSA-N O[C@H]1CC[C@@H](CC1)Nc1ncc2ncnc(Nc3ccc(Cl)c(Cl)c3)c2n1 Chemical compound O[C@H]1CC[C@@H](CC1)Nc1ncc2ncnc(Nc3ccc(Cl)c(Cl)c3)c2n1 HLOMTHGHDNSPAQ-UMSPYCQHSA-N 0.000 claims 1
• 241001377594 Rhene Species 0.000 claims 1
• 241000009298 Trigla lyra Species 0.000 claims 1
• 239000007983 Tris buffer Substances 0.000 claims 1
• HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 claims 1
• 229930013930 alkaloid Natural products 0.000 claims 1
• 150000003797 alkaloid derivatives Chemical class 0.000 claims 1
• 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
• 125000002843 carboxylic acid group Chemical group 0.000 claims 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
• VGQLNJWOULYVFV-QPIHLSAKSA-N dimethyl (1R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate Chemical group C1[C@@H]2C=C[C@H]1C(C(=O)OC)C2C(=O)OC VGQLNJWOULYVFV-QPIHLSAKSA-N 0.000 claims 1
• GMXHCXURJBRRDO-UHFFFAOYSA-N ethyl 4-[[4-(3-methylanilino)pyrimido[5,4-d]pyrimidin-6-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC=C(N=CN=C2NC=3C=C(C)C=CC=3)C2=N1 GMXHCXURJBRRDO-UHFFFAOYSA-N 0.000 claims 1
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