DE60010234T2 - 2-amino-6-anilino-purine und deren verwendung als arzneimittel - Google Patents

Info

Publication number

DE60010234T2

DE60010234T2 DE60010234T DE60010234T DE60010234T2 DE 60010234 T2 DE60010234 T2 DE 60010234T2 DE 60010234 T DE60010234 T DE 60010234T DE 60010234 T DE60010234 T DE 60010234T DE 60010234 T2 DE60010234 T2 DE 60010234T2

Authority

DE

Germany

Prior art keywords

ethyl

phenyl

purin

ylamino

radical

Prior art date

1999-02-18

Legal status (The legal status 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 status listed.)

Expired - Fee Related

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• AWRCGEJILTVONY-UHFFFAOYSA-N 6-n-phenyl-7h-purine-2,6-diamine Chemical compound C=12NC=NC2=NC(N)=NC=1NC1=CC=CC=C1 AWRCGEJILTVONY-UHFFFAOYSA-N 0.000 title claims abstract description 6
• 239000003814 drug Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 124
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 3
• -1 alkenylene radical Chemical class 0.000 claims description 729
• 125000000217 alkyl group Chemical group 0.000 claims description 163
• 125000004432 carbon atom Chemical group C* 0.000 claims description 137
• 150000003254 radicals Chemical class 0.000 claims description 127
• 125000003282 alkyl amino group Chemical group 0.000 claims description 124
• 239000001257 hydrogen Substances 0.000 claims description 107
• 229910052739 hydrogen Inorganic materials 0.000 claims description 107
• 229910052736 halogen Inorganic materials 0.000 claims description 90
• 125000003545 alkoxy group Chemical group 0.000 claims description 85
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 70
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 69
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 64
• 150000003839 salts Chemical class 0.000 claims description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
• 150000002431 hydrogen Chemical class 0.000 claims description 55
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 150000002367 halogens Chemical group 0.000 claims description 53
• 125000005843 halogen group Chemical group 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 45
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
• 125000002837 carbocyclic group Chemical group 0.000 claims description 41
• 229910052760 oxygen Inorganic materials 0.000 claims description 41
• 239000001301 oxygen Substances 0.000 claims description 41
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
• 229910052717 sulfur Inorganic materials 0.000 claims description 36
• 125000006239 protecting group Chemical group 0.000 claims description 35
• 125000001931 aliphatic group Chemical group 0.000 claims description 32
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 31
• 239000011593 sulfur Substances 0.000 claims description 31
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 30
• 125000000524 functional group Chemical group 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 125000000304 alkynyl group Chemical group 0.000 claims description 24
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
• 125000002947 alkylene group Chemical group 0.000 claims description 23
• 150000005840 aryl radicals Chemical class 0.000 claims description 23
• 238000006243 chemical reaction Methods 0.000 claims description 22
• 125000002252 acyl group Chemical group 0.000 claims description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000003277 amino group Chemical group 0.000 claims description 18
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
• 125000002757 morpholinyl group Chemical group 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 125000004193 piperazinyl group Chemical group 0.000 claims description 12
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 10
• 241001465754 Metazoa Species 0.000 claims description 9
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 9
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 238000003776 cleavage reaction Methods 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
• 230000007017 scission Effects 0.000 claims description 8
• 125000001544 thienyl 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
• 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 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• ANCBHJKEYPZCTE-UHFFFAOYSA-N ethyl 5-carbamoyl-4-methyl-2-[(2,3,4,5,6-pentafluorobenzoyl)amino]thiophene-3-carboxylate Chemical compound CC1=C(C(N)=O)SC(NC(=O)C=2C(=C(F)C(F)=C(F)C=2F)F)=C1C(=O)OCC ANCBHJKEYPZCTE-UHFFFAOYSA-N 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 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 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
• KDDZQNZNSORQST-UHFFFAOYSA-N 4-[[6-(3-aminoanilino)-9-ethylpurin-2-yl]amino]cyclohexan-1-ol Chemical compound N1=C(NC2CCC(O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC(N)=C1 KDDZQNZNSORQST-UHFFFAOYSA-N 0.000 claims description 4
• 150000003973 alkyl amines Chemical class 0.000 claims description 4
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
• 125000000033 alkoxyamino 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
• 150000001408 amides Chemical class 0.000 claims description 3
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• CBGRKQBWRIOZRW-IRJFHVNHSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=C(Cl)C=CC=C1Cl Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=C(Cl)C=CC=C1Cl CBGRKQBWRIOZRW-IRJFHVNHSA-N 0.000 claims description 2
• PTCPHEGADYDRBA-KOMQPUFPSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=C(NS(C)(=O)=O)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=C(NS(C)(=O)=O)C=C1 PTCPHEGADYDRBA-KOMQPUFPSA-N 0.000 claims description 2
• 125000004450 alkenylene group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000005059 halophenyl group Chemical group 0.000 claims description 2
• 230000036961 partial effect Effects 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 8
• 229940124530 sulfonamide Drugs 0.000 claims 6
• 150000003456 sulfonamides Chemical class 0.000 claims 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• QHDHNVFIKWGRJR-UHFFFAOYSA-N 1-cyclohexenol Chemical compound OC1=CCCCC1 QHDHNVFIKWGRJR-UHFFFAOYSA-N 0.000 claims 1
• 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
• GXLIFJYFGMHYDY-UHFFFAOYSA-N 3-(4-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(Cl)C=C1 GXLIFJYFGMHYDY-UHFFFAOYSA-N 0.000 claims 1
• PWFPMYPZAVNQQK-UHFFFAOYSA-N 3-amino-n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CCN PWFPMYPZAVNQQK-UHFFFAOYSA-N 0.000 claims 1
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
• HMARNKZPHXXDJL-UHFFFAOYSA-N 4-phenylbutane-2-sulfonamide Chemical compound NS(=O)(=O)C(C)CCC1=CC=CC=C1 HMARNKZPHXXDJL-UHFFFAOYSA-N 0.000 claims 1
• YDTYFWUKTSURMT-XGAFWQRZSA-N C(C)N1C2=NC(=NC(=C2N=C1)NC=1C=C(C=CC=1)NS(=O)(=O)C1=CC=C(C=C1)C)N[C@@H]1CC[C@H](CC1)O Chemical compound C(C)N1C2=NC(=NC(=C2N=C1)NC=1C=C(C=CC=1)NS(=O)(=O)C1=CC=C(C=C1)C)N[C@@H]1CC[C@H](CC1)O YDTYFWUKTSURMT-XGAFWQRZSA-N 0.000 claims 1
• IWUAVZILMFRURF-WGSAOQKQSA-N C1=CC(S(=O)(=O)N(C)CCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(S(=O)(=O)N(C)CCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC IWUAVZILMFRURF-WGSAOQKQSA-N 0.000 claims 1
• YNWWDOPNYNXVDI-HZCBDIJESA-N C1=CC(S(=O)(=O)N(C)CCCCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(S(=O)(=O)N(C)CCCCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC YNWWDOPNYNXVDI-HZCBDIJESA-N 0.000 claims 1
• LRGOIKNSKACXPP-QAQDUYKDSA-N C1=CC(S(=O)(=O)NCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC LRGOIKNSKACXPP-QAQDUYKDSA-N 0.000 claims 1
• GUXRBXGQFVOGQK-IYARVYRRSA-N C1=CC(S(=O)(=O)NCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(S(=O)(=O)NCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC GUXRBXGQFVOGQK-IYARVYRRSA-N 0.000 claims 1
• DTNKCWHYCNRGIE-HZCBDIJESA-N C1=CC(S(=O)(=O)NCCCCCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(S(=O)(=O)NCCCCCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC DTNKCWHYCNRGIE-HZCBDIJESA-N 0.000 claims 1
• 241001024304 Mino Species 0.000 claims 1
• PBLVDLGGCAHIKN-AQYVVDRMSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1 PBLVDLGGCAHIKN-AQYVVDRMSA-N 0.000 claims 1
• XDQRMPMOBUFTCK-RZFKFIIISA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC(C)=CC=C1C Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC(C)=CC=C1C XDQRMPMOBUFTCK-RZFKFIIISA-N 0.000 claims 1
• PEDXQBYACBOVTP-RZFKFIIISA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=C(C)C(C)=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=C(C)C(C)=C1 PEDXQBYACBOVTP-RZFKFIIISA-N 0.000 claims 1
• ZVOSURLQTNMRIW-JKIUYZKVSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=C(Cl)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=C(Cl)C=C1 ZVOSURLQTNMRIW-JKIUYZKVSA-N 0.000 claims 1
• BZZRVBHHQAMDOX-JKIUYZKVSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=CC=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=CC=C1 BZZRVBHHQAMDOX-JKIUYZKVSA-N 0.000 claims 1
• MBVDUWATFVRENP-IRJFHVNHSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=CS1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=CS1 MBVDUWATFVRENP-IRJFHVNHSA-N 0.000 claims 1
• APDRGDZDRHFXTI-IRJFHVNHSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)OC1=CC=CC=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)OC1=CC=CC=C1 APDRGDZDRHFXTI-IRJFHVNHSA-N 0.000 claims 1
• IJCDDLUUGSYBKN-IRJFHVNHSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NS(=O)(=O)C1=CC=C(OC)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NS(=O)(=O)C1=CC=C(OC)C=C1 IJCDDLUUGSYBKN-IRJFHVNHSA-N 0.000 claims 1
• CLPHEWFYYZBTMK-XUTJKUGGSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 CLPHEWFYYZBTMK-XUTJKUGGSA-N 0.000 claims 1
• CYPJBGCXDNAGDK-KESTWPANSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(OC)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(OC)C=C1 CYPJBGCXDNAGDK-KESTWPANSA-N 0.000 claims 1
• OWLAEBDRXPOHSH-XUTJKUGGSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=C(OC)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=C(OC)C=C1 OWLAEBDRXPOHSH-XUTJKUGGSA-N 0.000 claims 1
• LQFPIZICXXJLJK-HCGLCNNCSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(CC1)CCN1C1=CC=C(F)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(CC1)CCN1C1=CC=C(F)C=C1 LQFPIZICXXJLJK-HCGLCNNCSA-N 0.000 claims 1
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