SK114498A3 - Imidazo triazolo pyrimidinone derivatives, method of preparing them and their use - Google Patents

Info

Publication number

SK114498A3

SK114498A3 SK1144-98A SK114498A SK114498A3 SK 114498 A3 SK114498 A3 SK 114498A3 SK 114498 A SK114498 A SK 114498A SK 114498 A3 SK114498 A3 SK 114498A3

Authority

SK

Slovakia

Prior art keywords

optionally substituted

alkyl

phenyl

benzyl

substituted

Prior art date

1996-07-20

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 45
• DDCYOMQDEGIFNS-UHFFFAOYSA-N triazolo[4,5-d]pyrimidin-5-one Chemical class O=C1N=CC2=NN=NC2=N1 DDCYOMQDEGIFNS-UHFFFAOYSA-N 0.000 title claims description 14
• -1 benzylsulphonyl Chemical group 0.000 claims abstract description 452
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 149
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 110
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 102
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 74
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 57
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 42
• 239000002253 acid Substances 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 30
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 28
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 28
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 25
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 7
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
• 125000005843 halogen group Chemical group 0.000 claims abstract 4
• 229910006069 SO3H Inorganic materials 0.000 claims abstract 2
• 125000004122 cyclic group Chemical group 0.000 claims abstract 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 154
• 239000001257 hydrogen Substances 0.000 claims description 134
• 150000002431 hydrogen Chemical class 0.000 claims description 120
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 111
• 150000001875 compounds Chemical class 0.000 claims description 110
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical class [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 102
• 229910052736 halogen Inorganic materials 0.000 claims description 89
• 150000002367 halogens Chemical class 0.000 claims description 89
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 75
• 125000004432 carbon atom Chemical group C* 0.000 claims description 72
• 239000000203 mixture Substances 0.000 claims description 59
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 50
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 49
• 239000001301 oxygen Substances 0.000 claims description 46
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 43
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
• 150000003254 radicals Chemical class 0.000 claims description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 32
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 239000011593 sulfur Chemical group 0.000 claims description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
• 239000011737 fluorine Substances 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 20
• 125000004076 pyridyl group Chemical group 0.000 claims description 20
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
• 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 19
• 150000002832 nitroso derivatives Chemical class 0.000 claims description 19
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 18
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 18
• 150000001721 carbon Chemical group 0.000 claims description 18
• 239000002904 solvent Substances 0.000 claims description 18
• VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 17
• 239000004480 active ingredient Substances 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 125000004434 sulfur atom Chemical group 0.000 claims description 16
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 15
• 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 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical group O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 12
• 150000004985 diamines Chemical class 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 125000002541 furyl group Chemical group 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 10
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 9
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
• 150000003852 triazoles Chemical class 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 8
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 8
• 239000002168 alkylating agent Substances 0.000 claims description 8
• 229940100198 alkylating agent Drugs 0.000 claims description 8
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
• XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 8
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 8
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000005485 noradamantyl group Chemical group 0.000 claims description 8
• 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 8
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 8
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 8
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 7
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 7
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 7
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 6
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
• 239000005977 Ethylene Substances 0.000 claims description 6
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 6
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 239000003960 organic solvent Substances 0.000 claims description 5
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 5
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
• PCFIPYFVXDCWBW-UHFFFAOYSA-N tricyclo[3.3.1.03,7]nonane Chemical group C1C(C2)C3CC2CC1C3 PCFIPYFVXDCWBW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 4
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 4
• 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 4
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 4
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
• 125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 4
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
• 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 4
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 4
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 3
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 3
• 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims description 3
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• 125000006091 1,3-dioxolane group Chemical group 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 2
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 2
• 230000007935 neutral effect Effects 0.000 claims description 2
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 2
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 2
• 239000003791 organic solvent mixture Substances 0.000 claims 4
• HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical group CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 claims 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
• 230000018044 dehydration Effects 0.000 claims 2
• 238000006297 dehydration reaction Methods 0.000 claims 2
• 238000010438 heat treatment Methods 0.000 claims 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 1
• 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims 1
• 125000003118 aryl group Chemical group 0.000 abstract description 6
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract description 3
• 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
• 125000004450 alkenylene group Chemical group 0.000 abstract 1
• 125000004419 alkynylene group Chemical group 0.000 abstract 1
• 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
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