SK282823B6 - Derivát tienopyrimidínu, spôsob jeho prípravy a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

Info

Publication number

SK282823B6

SK282823B6 SK164-99A SK16499A SK282823B6 SK 282823 B6 SK282823 B6 SK 282823B6 SK 16499 A SK16499 A SK 16499A SK 282823 B6 SK282823 B6 SK 282823B6

Authority

SK

Slovakia

Prior art keywords

pyrimidine

chloro

pyridin

thieno

methyl

Prior art date

1996-08-12

Links

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• Global Dossier
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• 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title claims description 8
• 239000000825 pharmaceutical preparation Substances 0.000 title abstract 2
• -1 1-imidazolyl Chemical group 0.000 claims abstract description 197
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
• 150000001875 compounds Chemical class 0.000 claims description 64
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• 239000004480 active ingredient Substances 0.000 claims description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 238000010306 acid treatment Methods 0.000 claims description 2
• 150000007514 bases Chemical class 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 239000011630 iodine Substances 0.000 claims description 2
• XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-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
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• HDNPFZFZOMWGKL-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-imidazol-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=CN=C1 HDNPFZFZOMWGKL-UHFFFAOYSA-N 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 7
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
• 230000000694 effects Effects 0.000 abstract 1
• 201000001881 impotence Diseases 0.000 abstract 1
• 238000002560 therapeutic procedure Methods 0.000 abstract 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 203
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 45
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 44
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 44
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 22
• VCJCJLZVNOZZLS-UHFFFAOYSA-N [1]benzothiolo[2,3-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3SC2=N1 VCJCJLZVNOZZLS-UHFFFAOYSA-N 0.000 description 20
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• 238000000034 method Methods 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 12
• 239000000243 solution Substances 0.000 description 10
• 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
• 239000002253 acid Substances 0.000 description 9
• 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 7
• YXZIQOHVSRAWKC-UHFFFAOYSA-N 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 YXZIQOHVSRAWKC-UHFFFAOYSA-N 0.000 description 7
• 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 7
• 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 7
• 238000002360 preparation method Methods 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• SMDKSCIOCNGNMJ-UHFFFAOYSA-N 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2C(Cl)=C(C)SC2=N1 SMDKSCIOCNGNMJ-UHFFFAOYSA-N 0.000 description 6
• XNAZNWXVGHIFTK-UHFFFAOYSA-N 2,4,6-trichlorothieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(Cl)=CC2=C1Cl XNAZNWXVGHIFTK-UHFFFAOYSA-N 0.000 description 6
• CPWQCJFDDILDOU-UHFFFAOYSA-N 2,4-dichloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound C1CCCC2=C1C1=C(Cl)N=C(Cl)N=C1S2 CPWQCJFDDILDOU-UHFFFAOYSA-N 0.000 description 6
• BTGNDWIMNVJZJY-UHFFFAOYSA-N 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(C)=CC2=C1Cl BTGNDWIMNVJZJY-UHFFFAOYSA-N 0.000 description 6
• VSDJNTVDUJGCIG-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=CC=N1 VSDJNTVDUJGCIG-UHFFFAOYSA-N 0.000 description 6
• QGACYODQBCOZNU-UHFFFAOYSA-N 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 QGACYODQBCOZNU-UHFFFAOYSA-N 0.000 description 6
• FNXUGYJHBRERJW-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=CC=N1 FNXUGYJHBRERJW-UHFFFAOYSA-N 0.000 description 6
• PBYXYXCGKUOTBM-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CN=CC=N1 PBYXYXCGKUOTBM-UHFFFAOYSA-N 0.000 description 6
• 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 6
• USWGRWJYYZRROE-UHFFFAOYSA-N 5-(4-chloro-5-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=NO1 USWGRWJYYZRROE-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• HCVJZEMOIVEUFU-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=CC=N1 HCVJZEMOIVEUFU-UHFFFAOYSA-N 0.000 description 5
• OKMOUSJGXYXWHP-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=CN=C1 OKMOUSJGXYXWHP-UHFFFAOYSA-N 0.000 description 5
• LSFQLFVVDGXGTI-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CN=CC=N1 LSFQLFVVDGXGTI-UHFFFAOYSA-N 0.000 description 5
• ORKQHNXBQXVUTL-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=CC=N1 ORKQHNXBQXVUTL-UHFFFAOYSA-N 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 230000005764 inhibitory process Effects 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 4
• OIJVRHXVISHQPS-UHFFFAOYSA-N 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2C(C)=CSC2=N1 OIJVRHXVISHQPS-UHFFFAOYSA-N 0.000 description 4
• VTTHDZKNPJZPEM-UHFFFAOYSA-N 2-chlorothieno[2,3-d]pyrimidine Chemical class ClC1=NC=C2C=CSC2=N1 VTTHDZKNPJZPEM-UHFFFAOYSA-N 0.000 description 4
• ZAHZQWAXUPTDJE-UHFFFAOYSA-N 4,6-dichloro-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CN=CC=N1 ZAHZQWAXUPTDJE-UHFFFAOYSA-N 0.000 description 4
• 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 4
• CFPMOZDJGLHGEP-UHFFFAOYSA-N 4,6-dichloro-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=NC=C1 CFPMOZDJGLHGEP-UHFFFAOYSA-N 0.000 description 4
• UUTZWNAQEFVRGF-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CN=CC=N1 UUTZWNAQEFVRGF-UHFFFAOYSA-N 0.000 description 4
• KHIFGUKETTZHOC-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=NC=C1 KHIFGUKETTZHOC-UHFFFAOYSA-N 0.000 description 4
• YOGKDNQRONQSSZ-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=CN=C1 YOGKDNQRONQSSZ-UHFFFAOYSA-N 0.000 description 4
• WSHSXKLVAIQDHW-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=NC=C1 WSHSXKLVAIQDHW-UHFFFAOYSA-N 0.000 description 4
• FCIHEKTYBKVMGN-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=NC=C1 FCIHEKTYBKVMGN-UHFFFAOYSA-N 0.000 description 4
• LQPGWPKTMQTYEG-UHFFFAOYSA-N 5-(4,6-dichlorothieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=NO1 LQPGWPKTMQTYEG-UHFFFAOYSA-N 0.000 description 4
• 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 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
• 208000035475 disorder Diseases 0.000 description 4
• 239000012442 inert solvent Substances 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
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 4
• LDXCWOSUWRNYEW-UHFFFAOYSA-N 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2C(C)=C(C)SC2=N1 LDXCWOSUWRNYEW-UHFFFAOYSA-N 0.000 description 3
• WILLJMUZTUFCPD-UHFFFAOYSA-N 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(CC)=CC2=C1Cl WILLJMUZTUFCPD-UHFFFAOYSA-N 0.000 description 3
• MRYZQOMGKWXKKC-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=CC=N1 MRYZQOMGKWXKKC-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• 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
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000012154 double-distilled water Substances 0.000 description 3
• CDYVTVLXEWMCHU-UHFFFAOYSA-N ethyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate Chemical compound C1CCCC2=C1SC(N)=C2C(=O)OCC CDYVTVLXEWMCHU-UHFFFAOYSA-N 0.000 description 3
• ILYCZKOBLRJJSW-UHFFFAOYSA-N ethyl 2-amino-4-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C=1C(C)=CSC=1N ILYCZKOBLRJJSW-UHFFFAOYSA-N 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• KYOIYQZJSONJIQ-UHFFFAOYSA-N 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=C(C)S2 KYOIYQZJSONJIQ-UHFFFAOYSA-N 0.000 description 3
• 229910052757 nitrogen Inorganic materials 0.000 description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• 239000000454 talc Substances 0.000 description 3
• 235000012222 talc Nutrition 0.000 description 3
• 229910052623 talc Inorganic materials 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• 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
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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