DE19632423A1 - Thienopyrimidine - Google Patents

Info

Publication number

DE19632423A1

DE19632423A1 DE19632423A DE19632423A DE19632423A1 DE 19632423 A1 DE19632423 A1 DE 19632423A1 DE 19632423 A DE19632423 A DE 19632423A DE 19632423 A DE19632423 A DE 19632423A DE 19632423 A1 DE19632423 A1 DE 19632423A1

Authority

DE

Germany

Prior art keywords

pyrimidine

chloro

pyridin

thieno

methylthieno

Prior art date

1996-08-12

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.)

Withdrawn

Links

• Espacenet
• Global Dossier
• DPMA
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• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 201000001881 impotence Diseases 0.000 claims abstract description 4
• -1 Hal F Inorganic materials 0.000 claims description 433
• 150000001875 compounds Chemical class 0.000 claims description 53
• 239000002253 acid Substances 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 239000007788 liquid Substances 0.000 claims description 4
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 150000007514 bases Chemical class 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 239000002552 dosage form Substances 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• IWGJIRWGSGXDOG-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(C=1C=2CCCCC=2SC=1N=1)=NC=1N1C=NC=N1 IWGJIRWGSGXDOG-UHFFFAOYSA-N 0.000 claims description 2
• ZAXMDLTUPHLTQX-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-imidazol-1-yl-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(NCC=2C=C3OCOC3=CC=2)=C2C(C)=C(C)SC2=NC=1N1C=CN=C1 ZAXMDLTUPHLTQX-UHFFFAOYSA-N 0.000 claims description 2
• OXXZABNCYCFASI-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-pyrazol-1-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(C=1C=2CCCCC=2SC=1N=1)=NC=1N1C=CC=N1 OXXZABNCYCFASI-UHFFFAOYSA-N 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 2
• 238000006268 reductive amination reaction Methods 0.000 claims description 2
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 208000030499 combat disease Diseases 0.000 claims 1
• SANFLTPRLLETKD-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-imidazol-1-yl-6-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC(C)=CC2=C(NCC=2C=C3OCOC3=CC=2)N=C1N1C=CN=C1 SANFLTPRLLETKD-UHFFFAOYSA-N 0.000 claims 1
• YHXMDXMNJHOQDN-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-pyridin-3-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(C=1C=2CCCCC=2SC=1N=1)=NC=1C1=CC=CN=C1 YHXMDXMNJHOQDN-UHFFFAOYSA-N 0.000 claims 1
• QSPLYWHNVLKLNI-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-5-chloro-2-imidazol-1-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(NCC=2C=C3OCOC3=CC=2)=C2C(Cl)=CSC2=NC=1N1C=CN=C1 QSPLYWHNVLKLNI-UHFFFAOYSA-N 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 239000007787 solid Substances 0.000 claims 1
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 3
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 3
• 230000000694 effects Effects 0.000 abstract description 2
• 238000002560 therapeutic procedure Methods 0.000 abstract description 2
• 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 254
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 63
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 59
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 57
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 56
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 55
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 31
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 27
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 23
• 238000006243 chemical reaction Methods 0.000 description 20
• VCJCJLZVNOZZLS-UHFFFAOYSA-N [1]benzothiolo[2,3-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3SC2=N1 VCJCJLZVNOZZLS-UHFFFAOYSA-N 0.000 description 19
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 15
• 239000000243 solution Substances 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 150000003254 radicals Chemical class 0.000 description 11
• GEPPWBCPYIBEHQ-UHFFFAOYSA-N 4-chloro-2-pyrazin-2-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CN=CC=N1 GEPPWBCPYIBEHQ-UHFFFAOYSA-N 0.000 description 9
• GTVYNNDHOKJILR-UHFFFAOYSA-N 4-chloro-2-pyridin-2-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=CC=N1 GTVYNNDHOKJILR-UHFFFAOYSA-N 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• YYIQTSLTZZVFCK-UHFFFAOYSA-N 4-chloro-2-pyridin-4-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=NC=C1 YYIQTSLTZZVFCK-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• 229910019213 POCl3 Inorganic materials 0.000 description 6
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• 239000002585 base Substances 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 239000012442 inert solvent Substances 0.000 description 5
• 125000004076 pyridyl group Chemical group 0.000 description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
• VTTHDZKNPJZPEM-UHFFFAOYSA-N 2-chlorothieno[2,3-d]pyrimidine Chemical class ClC1=NC=C2C=CSC2=N1 VTTHDZKNPJZPEM-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• ISKGKMVCOYALTM-UHFFFAOYSA-N 4-chloro-2-pyridin-3-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=CN=C1 ISKGKMVCOYALTM-UHFFFAOYSA-N 0.000 description 3
• ZFJKZWDYHJLWOS-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=CN=C1 ZFJKZWDYHJLWOS-UHFFFAOYSA-N 0.000 description 3
• IWTSZXCXPHRPCW-UHFFFAOYSA-N 5-(4-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=NO1 IWTSZXCXPHRPCW-UHFFFAOYSA-N 0.000 description 3
• LDWOHYXTFVXIQS-UHFFFAOYSA-N 5-(4-chloro-6-nitrothieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=NO1 LDWOHYXTFVXIQS-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 239000012154 double-distilled water Substances 0.000 description 3
• 239000011521 glass Substances 0.000 description 3
• 230000005764 inhibitory process Effects 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
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• 239000000454 talc Substances 0.000 description 3
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• IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 2
• DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 2
• OCNMSDZALRAYEX-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1Cl OCNMSDZALRAYEX-UHFFFAOYSA-N 0.000 description 2
• CIUYJYRQKYGNQP-UHFFFAOYSA-N (3-nitrophenyl)methanamine Chemical compound NCC1=CC=CC([N+]([O-])=O)=C1 CIUYJYRQKYGNQP-UHFFFAOYSA-N 0.000 description 2
• IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• FUDYRLUSXBRPIA-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-ylmethanamine Chemical compound O1CCOC2=CC(CN)=CC=C21 FUDYRLUSXBRPIA-UHFFFAOYSA-N 0.000 description 2
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
• UQJWNAACMPKURL-UHFFFAOYSA-N 2-imidazol-1-yl-6-methyl-n-[(3-nitrophenyl)methyl]thieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C(N2C=NC=C2)N=C2SC(C)=CC2=C1NCC1=CC=CC([N+]([O-])=O)=C1 UQJWNAACMPKURL-UHFFFAOYSA-N 0.000 description 2
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
• MWCLMVSZYQJPRH-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CN=CC=N1 MWCLMVSZYQJPRH-UHFFFAOYSA-N 0.000 description 2
• ZYRYAZJTWFMYGE-UHFFFAOYSA-N 4,6-dichloro-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=CC=N1 ZYRYAZJTWFMYGE-UHFFFAOYSA-N 0.000 description 2
• CUURLLLXVGYGBR-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=CN=C1 CUURLLLXVGYGBR-UHFFFAOYSA-N 0.000 description 2
• CXZPHUKTMYBJLS-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CN=CC=N1 CXZPHUKTMYBJLS-UHFFFAOYSA-N 0.000 description 2
• QNMXKWMTQYUFIP-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=NC=C1 QNMXKWMTQYUFIP-UHFFFAOYSA-N 0.000 description 2
• JGSWNEJDONIMSQ-UHFFFAOYSA-N 5-(4,5-dichloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NO1 JGSWNEJDONIMSQ-UHFFFAOYSA-N 0.000 description 2
• LZEXIGQJTPZXOJ-UHFFFAOYSA-N 5-(4-chloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=NO1 LZEXIGQJTPZXOJ-UHFFFAOYSA-N 0.000 description 2
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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• 108090000790 Enzymes Proteins 0.000 description 2
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• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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• SUGUIMCHRCIMAY-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-2-ylthieno[2,3-d]pyrimidine;n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-nitro-2-pyridin-2-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=CC=N1.N1=C2SC([N+](=O)[O-])=CC2=C(NCC=2C=C3OCCOC3=CC=2)N=C1C1=CC=CC=N1 SUGUIMCHRCIMAY-UHFFFAOYSA-N 0.000 description 1
• KFKSNDWROXUDSB-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-3-ylthieno[2,3-d]pyrimidine;6-nitro-n-(2-phenylethyl)-2-pyridin-3-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=CN=C1.N1=C(C=2C=NC=CC=2)N=C2SC([N+](=O)[O-])=CC2=C1NCCC1=CC=CC=C1 KFKSNDWROXUDSB-UHFFFAOYSA-N 0.000 description 1
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• ZGQRCJSUHYGBFH-UHFFFAOYSA-N 5-(4-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole;n-[(3-chloro-4-methoxyphenyl)methyl]-5,6-dimethyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=NO1.C1=C(Cl)C(OC)=CC=C1CNC1=NC(C=2ON=CC=2)=NC2=C1C(C)=C(C)S2 ZGQRCJSUHYGBFH-UHFFFAOYSA-N 0.000 description 1
• IBTIZRDTFKGICX-UHFFFAOYSA-N 5-(4-chloro-5-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole;n-[(3,4-dimethoxyphenyl)methyl]-5-methyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=NO1.C1=C(OC)C(OC)=CC=C1CNC1=NC(C=2ON=CC=2)=NC2=C1C(C)=CS2 IBTIZRDTFKGICX-UHFFFAOYSA-N 0.000 description 1
• MWRFSEYWRUQNCH-UHFFFAOYSA-N 5-(4-chloro-6-ethylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=NO1 MWRFSEYWRUQNCH-UHFFFAOYSA-N 0.000 description 1
• VEXZFSOVRCAOFT-UHFFFAOYSA-N 5-(4-chloro-6-ethylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole;6-ethyl-2-(1,2-oxazol-5-yl)-n-(2-phenylethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=NO1.N1=C(C=2ON=CC=2)N=C2SC(CC)=CC2=C1NCCC1=CC=CC=C1 VEXZFSOVRCAOFT-UHFFFAOYSA-N 0.000 description 1
• YGGFPKFCBSTMQS-UHFFFAOYSA-N 5-(4-chloro-6-ethylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole;n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-ethyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=NO1.N1=C2SC(CC)=CC2=C(NCC=2C=C3OCCOC3=CC=2)N=C1C1=CC=NO1 YGGFPKFCBSTMQS-UHFFFAOYSA-N 0.000 description 1
• GULXKZDMNVVRDB-UHFFFAOYSA-N 5-(4-chloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=NO1 GULXKZDMNVVRDB-UHFFFAOYSA-N 0.000 description 1
• VOBNUAGPAHSCLD-UHFFFAOYSA-N 5-(4-chloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole;6-methyl-2-(1,2-oxazol-5-yl)-n-(2-phenylethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=NO1.N1=C(C=2ON=CC=2)N=C2SC(C)=CC2=C1NCCC1=CC=CC=C1 VOBNUAGPAHSCLD-UHFFFAOYSA-N 0.000 description 1
• XKHUOIGHFZCRKD-UHFFFAOYSA-N 5-(4-chloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole;n-[(3,4-dimethoxyphenyl)methyl]-6-methyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=NO1.C1=C(OC)C(OC)=CC=C1CNC1=NC(C=2ON=CC=2)=NC2=C1C=C(C)S2 XKHUOIGHFZCRKD-UHFFFAOYSA-N 0.000 description 1
• UVTWHXJYQNLXTH-UHFFFAOYSA-N 5-(4-chloro-6-nitrothieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole;6-nitro-2-(1,2-oxazol-5-yl)-n-(2-phenylethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=NO1.N1=C(C=2ON=CC=2)N=C2SC([N+](=O)[O-])=CC2=C1NCCC1=CC=CC=C1 UVTWHXJYQNLXTH-UHFFFAOYSA-N 0.000 description 1
• UQFCRYANVCBPIC-UHFFFAOYSA-N 5-[4-chloro-6-(trifluoromethyl)thieno[2,3-d]pyrimidin-2-yl]-1,2-oxazole N-[(4-fluorophenyl)methyl]-2-(1,2-oxazol-5-yl)-6-(trifluoromethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound O1N=CC=C1C=1N=C(C2=C(N1)SC(=C2)C(F)(F)F)NCC2=CC=C(C=C2)F.ClC=2C1=C(N=C(N2)C2=CC=NO2)SC(=C1)C(F)(F)F UQFCRYANVCBPIC-UHFFFAOYSA-N 0.000 description 1
• HLXPREREERFEMN-UHFFFAOYSA-N 5-chloro-N-[(3,4-dimethoxyphenyl)methyl]-6-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidin-4-amine 4,5-dichloro-6-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C(C=NC=C1)C=1N=C(C2=C(N1)SC(=C2Cl)C)NCC2=CC(=C(C=C2)OC)OC.ClC=2C1=C(N=C(N2)C2=NC=CN=C2)SC(=C1Cl)C HLXPREREERFEMN-UHFFFAOYSA-N 0.000 description 1
• DJAWNMIGRUOPEJ-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-2-imidazol-1-yl-6-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(NCC=2C=C3OCCOC3=CC=2)=C2C(Cl)=C(C)SC2=NC=1N1C=CN=C1 DJAWNMIGRUOPEJ-UHFFFAOYSA-N 0.000 description 1
• GCVXJDLUFADJQO-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-methyl-2-(1,2,4-triazol-1-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(NCC=2C=C3OCCOC3=CC=2)=C2C(Cl)=C(C)SC2=NC=1N1C=NC=N1 GCVXJDLUFADJQO-UHFFFAOYSA-N 0.000 description 1
• UHGAJVNRGJSDBH-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-methyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine;5-(4,5-dichloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NO1.N=1C(NCC=2C=C3OCCOC3=CC=2)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NO1 UHGAJVNRGJSDBH-UHFFFAOYSA-N 0.000 description 1
• GOQVQZXOTJKVCN-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-methyl-2-pyrazol-1-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(NCC=2C=C3OCCOC3=CC=2)=C2C(Cl)=C(C)SC2=NC=1N1C=CC=N1 GOQVQZXOTJKVCN-UHFFFAOYSA-N 0.000 description 1
• AMPYDXONNGCRNX-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidin-4-amine;4,5-dichloro-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=CN=C1.N=1C(NCC=2C=C3OCCOC3=CC=2)=C2C(Cl)=C(C)SC2=NC=1C1=CC=CN=C1 AMPYDXONNGCRNX-UHFFFAOYSA-N 0.000 description 1
• BVZVWKPUPNQNNI-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidin-4-amine;4,5-dichloro-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NC=C1.N=1C(NCC=2C=C3OCCOC3=CC=2)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NC=C1 BVZVWKPUPNQNNI-UHFFFAOYSA-N 0.000 description 1
• QDKCCRJSZPQDPF-UHFFFAOYSA-N 5-chloro-n-[(3,4-dichlorophenyl)methyl]-2-imidazol-1-yl-6-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(Cl)=C(C)SC2=NC(N2C=NC=C2)=NC=1NCC1=CC=C(Cl)C(Cl)=C1 QDKCCRJSZPQDPF-UHFFFAOYSA-N 0.000 description 1
• SRZYEHVPCAVVET-UHFFFAOYSA-N 5-chloro-n-[(3,4-dichlorophenyl)methyl]-6-methyl-2-(1,2,4-triazol-1-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(Cl)=C(C)SC2=NC(N2N=CN=C2)=NC=1NCC1=CC=C(Cl)C(Cl)=C1 SRZYEHVPCAVVET-UHFFFAOYSA-N 0.000 description 1
• RNLJLBMLYLYSTL-UHFFFAOYSA-N 5-chloro-n-[(3,4-dichlorophenyl)methyl]-6-methyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(Cl)=C(C)SC2=NC(C=2ON=CC=2)=NC=1NCC1=CC=C(Cl)C(Cl)=C1 RNLJLBMLYLYSTL-UHFFFAOYSA-N 0.000 description 1
• JTJRYEJEJVIKLE-UHFFFAOYSA-N 5-chloro-n-[(3,4-dichlorophenyl)methyl]-6-methyl-2-pyrazol-1-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(Cl)=C(C)SC2=NC(N2N=CC=C2)=NC=1NCC1=CC=C(Cl)C(Cl)=C1 JTJRYEJEJVIKLE-UHFFFAOYSA-N 0.000 description 1
• UVNKNHXBDASVGP-UHFFFAOYSA-N 5-chloro-n-[(3,4-dichlorophenyl)methyl]-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidin-4-amine;4,5-dichloro-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=CN=C1.C=12C(Cl)=C(C)SC2=NC(C=2C=NC=CC=2)=NC=1NCC1=CC=C(Cl)C(Cl)=C1 UVNKNHXBDASVGP-UHFFFAOYSA-N 0.000 description 1
• KAMTUROBKMIIIR-UHFFFAOYSA-N 5-chloro-n-[(3,4-dichlorophenyl)methyl]-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidin-4-amine;4,5-dichloro-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NC=C1.C=12C(Cl)=C(C)SC2=NC(C=2C=CN=CC=2)=NC=1NCC1=CC=C(Cl)C(Cl)=C1 KAMTUROBKMIIIR-UHFFFAOYSA-N 0.000 description 1
• GZCWTFAMYDGTJT-UHFFFAOYSA-N 5-chloro-n-[(3,4-dimethoxyphenyl)methyl]-2-imidazol-1-yl-6-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC(N2C=NC=C2)=NC2=C1C(Cl)=C(C)S2 GZCWTFAMYDGTJT-UHFFFAOYSA-N 0.000 description 1
• VLLUUEPFBTWYKD-UHFFFAOYSA-N 5-chloro-n-[(3,4-dimethoxyphenyl)methyl]-6-methyl-2-(1,2,4-triazol-1-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC(N2N=CN=C2)=NC2=C1C(Cl)=C(C)S2 VLLUUEPFBTWYKD-UHFFFAOYSA-N 0.000 description 1
• XEGJLNSIEBVZJW-UHFFFAOYSA-N 5-chloro-n-[(3,4-dimethoxyphenyl)methyl]-6-methyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine;5-(4,5-dichloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NO1.C1=C(OC)C(OC)=CC=C1CNC1=NC(C=2ON=CC=2)=NC2=C1C(Cl)=C(C)S2 XEGJLNSIEBVZJW-UHFFFAOYSA-N 0.000 description 1
• BSKSMRUYXINGKV-UHFFFAOYSA-N 5-chloro-n-[(3,4-dimethoxyphenyl)methyl]-6-methyl-2-pyrazol-1-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC(N2N=CC=C2)=NC2=C1C(Cl)=C(C)S2 BSKSMRUYXINGKV-UHFFFAOYSA-N 0.000 description 1
• NBOSMZAAPSWAPF-UHFFFAOYSA-N 5-chloro-n-[(3,4-dimethoxyphenyl)methyl]-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidin-4-amine;4,5-dichloro-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NC=C1.C1=C(OC)C(OC)=CC=C1CNC1=NC(C=2C=CN=CC=2)=NC2=C1C(Cl)=C(C)S2 NBOSMZAAPSWAPF-UHFFFAOYSA-N 0.000 description 1
• YCIVSUCVVOLOAE-UHFFFAOYSA-N 5-chloro-n-[(3-chloro-4-methoxyphenyl)methyl]-2-imidazol-1-yl-6-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(N2C=NC=C2)=NC2=C1C(Cl)=C(C)S2 YCIVSUCVVOLOAE-UHFFFAOYSA-N 0.000 description 1
• PZRACWDCESRDKR-UHFFFAOYSA-N 5-chloro-n-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-2-(1,2,4-triazol-1-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(N2N=CN=C2)=NC2=C1C(Cl)=C(C)S2 PZRACWDCESRDKR-UHFFFAOYSA-N 0.000 description 1
• HRJRUAKXFFWOCA-UHFFFAOYSA-N 5-chloro-n-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-2-(1,2-oxazol-5-yl)thieno[2,3-d]pyrimidin-4-amine;5-(4,5-dichloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NO1.C1=C(Cl)C(OC)=CC=C1CNC1=NC(C=2ON=CC=2)=NC2=C1C(Cl)=C(C)S2 HRJRUAKXFFWOCA-UHFFFAOYSA-N 0.000 description 1
• VABSVEOWWQMMAD-UHFFFAOYSA-N 5-chloro-n-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-2-pyrazol-1-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(N2N=CC=C2)=NC2=C1C(Cl)=C(C)S2 VABSVEOWWQMMAD-UHFFFAOYSA-N 0.000 description 1
• ITSVILFFWADLAG-UHFFFAOYSA-N 5-chloro-n-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidin-4-amine;4,5-dichloro-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=CN=C1.C1=C(Cl)C(OC)=CC=C1CNC1=NC(C=2C=NC=CC=2)=NC2=C1C(Cl)=C(C)S2 ITSVILFFWADLAG-UHFFFAOYSA-N 0.000 description 1
• CNRNEZOHYROEHS-UHFFFAOYSA-N 5-chloro-n-[(4-fluorophenyl)methyl]-6-methyl-2-(1,2,4-triazol-1-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(Cl)=C(C)SC2=NC(N2N=CN=C2)=NC=1NCC1=CC=C(F)C=C1 CNRNEZOHYROEHS-UHFFFAOYSA-N 0.000 description 1
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