SK284979B6 - Derivát tienopyrimidínu, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

Info

Publication number

SK284979B6

SK284979B6 SK502-99A SK50299A SK284979B6 SK 284979 B6 SK284979 B6 SK 284979B6 SK 50299 A SK50299 A SK 50299A SK 284979 B6 SK284979 B6 SK 284979B6

Authority

SK

Slovakia

Prior art keywords

pyrimidin

chloro

benzoic acid

thieno

pyrimidine

Prior art date

1996-10-24

Links

• Espacenet
• Global Dossier
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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title claims abstract description 7
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
• 238000002360 preparation method Methods 0.000 claims abstract description 7
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 4
• -1 1,3- dioxolan-4-yl Chemical group 0.000 claims description 384
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 314
• 150000001875 compounds Chemical class 0.000 claims description 61
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 11
• 239000004480 active ingredient Substances 0.000 claims description 10
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
• 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 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 239000000460 chlorine Substances 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 150000007513 acids Chemical class 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 4
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 239000011630 iodine Substances 0.000 claims description 3
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
• OFAWUMINJWKLCV-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C2=C(CCCC2)S2)C2=N1 OFAWUMINJWKLCV-UHFFFAOYSA-N 0.000 claims description 2
• GSEIXLZVZVTEJS-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-methylthieno[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound N1=C2SC(C)=CC2=C(NCC=2C=C3OCOC3=CC=2)N=C1C1=CC=C(C(O)=O)C=C1 GSEIXLZVZVTEJS-UHFFFAOYSA-N 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 206010019280 Heart failures Diseases 0.000 claims description 2
• 239000002552 dosage form Substances 0.000 claims description 2
• 201000001881 impotence Diseases 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 2
• 239000007787 solid Substances 0.000 claims description 2
• PDEQPRBUBSUBSM-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethylamino)-6-methylthieno[2,3-d]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound N1=C2SC(C)=CC2=C(NCC=2C=C3OCOC3=CC=2)N=C1N1CCC(C(O)=O)CC1 PDEQPRBUBSUBSM-UHFFFAOYSA-N 0.000 claims 1
• JBUBDBSGKBJKBP-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C2=C(CCCC2)S2)C2=N1 JBUBDBSGKBJKBP-UHFFFAOYSA-N 0.000 claims 1
• XLPFHHGFLJMKCI-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound N=1C(NCC=2C=C3OCOC3=CC=2)=C2C(C)=C(C)SC2=NC=1C1=CC=C(C(O)=O)C=C1 XLPFHHGFLJMKCI-UHFFFAOYSA-N 0.000 claims 1
• NMCXWBUEDGJLDG-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-chlorothieno[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(Cl)S2)C2=N1 NMCXWBUEDGJLDG-UHFFFAOYSA-N 0.000 claims 1
• RIYVLKZOHQYWPV-UHFFFAOYSA-N 4-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(C=2C=CC(=CC=2)C(O)=O)=NC2=C1C(CCCC1)=C1S2 RIYVLKZOHQYWPV-UHFFFAOYSA-N 0.000 claims 1
• 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
• 230000005764 inhibitory process Effects 0.000 abstract description 4
• 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 abstract 1
• 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 abstract 1
• 239000005711 Benzoic acid Substances 0.000 description 163
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 147
• 235000010233 benzoic acid Nutrition 0.000 description 144
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 85
• FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 76
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 62
• 150000004702 methyl esters Chemical class 0.000 description 58
• 125000004494 ethyl ester group Chemical group 0.000 description 28
• RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 21
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• 239000000243 solution Substances 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• 150000002148 esters Chemical class 0.000 description 10
• 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 9
• 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 9
• 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 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• VCJCJLZVNOZZLS-UHFFFAOYSA-N [1]benzothiolo[2,3-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3SC2=N1 VCJCJLZVNOZZLS-UHFFFAOYSA-N 0.000 description 8
• ICIWZNWNCSJBCO-UHFFFAOYSA-N methyl 4-(4-chloro-6-methylthieno[2,3-d]pyrimidin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(Cl)=C(C=C(C)S2)C2=N1 ICIWZNWNCSJBCO-UHFFFAOYSA-N 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 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 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-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
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 239000003814 drug Substances 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 159000000000 sodium salts Chemical class 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• KLQGCWMIEYTEMY-UHFFFAOYSA-N methyl 4-(4,5-dichloro-6-methylthieno[2,3-d]pyrimidin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(Cl)=C(C(Cl)=C(C)S2)C2=N1 KLQGCWMIEYTEMY-UHFFFAOYSA-N 0.000 description 5
• 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 description 5
• 239000007858 starting material Substances 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
• 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 4
• FGZFWBZPHOEROB-UHFFFAOYSA-N 4-(4-chloro-6-ethylthieno[2,3-d]pyrimidin-2-yl)benzoic acid Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=C(C(O)=O)C=C1 FGZFWBZPHOEROB-UHFFFAOYSA-N 0.000 description 4
• RSFOCWDJBLNDFF-UHFFFAOYSA-N 4-(4-chloro-6-nitrothieno[2,3-d]pyrimidin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC(Cl)=C(C=C(S2)[N+]([O-])=O)C2=N1 RSFOCWDJBLNDFF-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 4
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 4
• 208000035475 disorder Diseases 0.000 description 4
• 229910052736 halogen Inorganic materials 0.000 description 4
• 150000002367 halogens 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
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• FUDYRLUSXBRPIA-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-ylmethanamine Chemical compound O1CCOC2=CC(CN)=CC=C21 FUDYRLUSXBRPIA-UHFFFAOYSA-N 0.000 description 3
• JIMQJLMPZVYOFI-UHFFFAOYSA-N 2,4-dichloro-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(C(F)(F)F)=CC2=C1Cl JIMQJLMPZVYOFI-UHFFFAOYSA-N 0.000 description 3
• DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-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
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
• 150000001340 alkali metals Chemical class 0.000 description 3
• 239000012154 double-distilled water Substances 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• FQRUIHYITBVGTJ-UHFFFAOYSA-N methyl 4-(4,6-dichlorothieno[2,3-d]pyrimidin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(Cl)=C(C=C(Cl)S2)C2=N1 FQRUIHYITBVGTJ-UHFFFAOYSA-N 0.000 description 3
• SDZIRLWQAYNJAI-UHFFFAOYSA-N methyl 4-(4-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(Cl)=C(C(C)=C(C)S2)C2=N1 SDZIRLWQAYNJAI-UHFFFAOYSA-N 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• 229910052708 sodium Inorganic materials 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
• 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
• ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• LKVYOLPBXKHGFY-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methylamino]-6-methylthieno[2,3-d]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound N1=C(N2CCC(CC2)C(O)=O)N=C2SC(C)=CC2=C1NCC1=CC=C(F)C=C1 LKVYOLPBXKHGFY-UHFFFAOYSA-N 0.000 description 2
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• TUSGCCPHUAIEMY-UHFFFAOYSA-N ethyl 1-[4-[(3,4-dimethoxyphenyl)methylamino]-5-methylthieno[2,3-d]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(NCC=2C=C(OC)C(OC)=CC=2)=C(C(C)=CS2)C2=N1 TUSGCCPHUAIEMY-UHFFFAOYSA-N 0.000 description 1
• VPDBVZUBHLFAGQ-UHFFFAOYSA-N ethyl 1-[6-nitro-4-[(3-nitrophenyl)methylamino]thieno[2,3-d]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(NCC=2C=C(C=CC=2)[N+]([O-])=O)=C(C=C(S2)[N+]([O-])=O)C2=N1 VPDBVZUBHLFAGQ-UHFFFAOYSA-N 0.000 description 1
• IBBDIRWOKRFCJB-UHFFFAOYSA-N ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate methyl 4-(4-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)benzoate Chemical compound ClC=1C2=C(N=C(N1)C1=CC=C(C(=O)OC)C=C1)SC(=C2C)C.NC=2SC(=C(C2C(=O)OCC)C)C IBBDIRWOKRFCJB-UHFFFAOYSA-N 0.000 description 1
• IERFTHZUUOYHHX-UHFFFAOYSA-N ethyl 2-amino-4-chloro-5-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C)=C1Cl IERFTHZUUOYHHX-UHFFFAOYSA-N 0.000 description 1
• DGEIHXNYBBKRMS-UHFFFAOYSA-N ethyl 2-amino-5-chlorothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=C(Cl)SC=1N DGEIHXNYBBKRMS-UHFFFAOYSA-N 0.000 description 1
• AYBUNZGJQVYGTM-UHFFFAOYSA-N ethyl 2-amino-5-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C)SC=1N AYBUNZGJQVYGTM-UHFFFAOYSA-N 0.000 description 1
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
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• 230000002349 favourable effect Effects 0.000 description 1
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• 239000007789 gas Substances 0.000 description 1
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• 235000013773 glyceryl triacetate Nutrition 0.000 description 1
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 239000007943 implant Substances 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
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• XPBHWSMZTSSEJE-UHFFFAOYSA-N methyl 3-cyanobenzoate Chemical compound COC(=O)C1=CC=CC(C#N)=C1 XPBHWSMZTSSEJE-UHFFFAOYSA-N 0.000 description 1
• BKOFSDOKUKNCFH-UHFFFAOYSA-N methyl 4-(4-chloro-5-methylthieno[2,3-d]pyrimidin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(Cl)=C(C(C)=CS2)C2=N1 BKOFSDOKUKNCFH-UHFFFAOYSA-N 0.000 description 1
• HFOGKFPVGKOVQI-UHFFFAOYSA-N methyl 4-(4-chloro-6-nitrothieno[2,3-d]pyrimidin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(Cl)=C(C=C(S2)[N+]([O-])=O)C2=N1 HFOGKFPVGKOVQI-UHFFFAOYSA-N 0.000 description 1
• VILQDUKEPCKQMW-UHFFFAOYSA-N methyl 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-methylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(C)S2)C2=N1 VILQDUKEPCKQMW-UHFFFAOYSA-N 0.000 description 1
• NYLYXYSPEQUNIP-UHFFFAOYSA-N methyl 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-nitrothieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(S2)[N+]([O-])=O)C2=N1 NYLYXYSPEQUNIP-UHFFFAOYSA-N 0.000 description 1
• HFQHCKNLRAHJMT-UHFFFAOYSA-N methyl 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-propylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound N1=C2SC(CCC)=CC2=C(NCC=2C=C3OCOC3=CC=2)N=C1C1=CC=C(C(=O)OC)C=C1 HFQHCKNLRAHJMT-UHFFFAOYSA-N 0.000 description 1
• JZEZFEXPNNYVBR-UHFFFAOYSA-N methyl 4-[4-[(3,4-dichlorophenyl)methylamino]-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCC=2C=C(Cl)C(Cl)=CC=2)=C(C(C)=C(C)S2)C2=N1 JZEZFEXPNNYVBR-UHFFFAOYSA-N 0.000 description 1
• BCUNKNBYTLBYHU-UHFFFAOYSA-N methyl 4-[4-[(3,4-dichlorophenyl)methylamino]-5-methylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCC=2C=C(Cl)C(Cl)=CC=2)=C(C(C)=CS2)C2=N1 BCUNKNBYTLBYHU-UHFFFAOYSA-N 0.000 description 1
• SOBVPOWKKLLACB-UHFFFAOYSA-N methyl 4-[4-[(3,4-dimethoxyphenyl)methylamino]-5-methylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCC=2C=C(OC)C(OC)=CC=2)=C(C(C)=CS2)C2=N1 SOBVPOWKKLLACB-UHFFFAOYSA-N 0.000 description 1
• XALMCRNVAQWUDJ-UHFFFAOYSA-N methyl 4-[4-[2-(1,3-benzodioxol-5-yl)ethylamino]-6-nitrothieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCCC=2C=C3OCOC3=CC=2)=C(C=C(S2)[N+]([O-])=O)C2=N1 XALMCRNVAQWUDJ-UHFFFAOYSA-N 0.000 description 1
• XKIUNULXYGVQPD-UHFFFAOYSA-N methyl 4-[4-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethylamino]-5-methylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCCC=2C=C3OCCOC3=CC=2)=C(C(C)=CS2)C2=N1 XKIUNULXYGVQPD-UHFFFAOYSA-N 0.000 description 1
• XQPICLBTFWZDBB-UHFFFAOYSA-N methyl 4-[4-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethylamino]-6-ethylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound N1=C2SC(CC)=CC2=C(NCCC=2C=C3OCCOC3=CC=2)N=C1C1=CC=C(C(=O)OC)C=C1 XQPICLBTFWZDBB-UHFFFAOYSA-N 0.000 description 1
• QFKIFLWFQJIYPR-UHFFFAOYSA-N methyl 4-[4-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethylamino]-6-nitrothieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCCC=2C=C3OCCOC3=CC=2)=C(C=C(S2)[N+]([O-])=O)C2=N1 QFKIFLWFQJIYPR-UHFFFAOYSA-N 0.000 description 1
• SLCCAHSXUVLGGV-UHFFFAOYSA-N methyl 4-[5-chloro-6-methyl-4-[(3-nitrophenyl)methylamino]thieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCC=2C=C(C=CC=2)[N+]([O-])=O)=C(C(Cl)=C(C)S2)C2=N1 SLCCAHSXUVLGGV-UHFFFAOYSA-N 0.000 description 1
• LCVAKVMQIQHHKZ-UHFFFAOYSA-N methyl 4-[6-chloro-4-[(3,4-dichlorophenyl)methylamino]thieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCC=2C=C(Cl)C(Cl)=CC=2)=C(C=C(Cl)S2)C2=N1 LCVAKVMQIQHHKZ-UHFFFAOYSA-N 0.000 description 1
• NSBIGCPGKJARHT-UHFFFAOYSA-N methyl 4-[6-ethyl-4-(2-phenylethylamino)thieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound N1=C(C=2C=CC(=CC=2)C(=O)OC)N=C2SC(CC)=CC2=C1NCCC1=CC=CC=C1 NSBIGCPGKJARHT-UHFFFAOYSA-N 0.000 description 1
• JOACXHSGPQXNQD-UHFFFAOYSA-N methyl 4-[6-nitro-4-(2-phenylethylamino)thieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(NCCC=2C=CC=CC=2)=C(C=C(S2)[N+]([O-])=O)C2=N1 JOACXHSGPQXNQD-UHFFFAOYSA-N 0.000 description 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
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• QDACCFRDPVSPEC-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2,5-dichloro-6-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C2OCOC2=CC(CNC=2N=C(Cl)N=C3SC(=C(C3=2)Cl)C)=C1 QDACCFRDPVSPEC-UHFFFAOYSA-N 0.000 description 1
• SFKXABRBTMDYBC-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C1CCCC2=C1C1=C(NCC=3C=C4OCOC4=CC=3)N=C(Cl)N=C1S2 SFKXABRBTMDYBC-UHFFFAOYSA-N 0.000 description 1
• GMOJSYQEVFUKKP-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine;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.C1CCCC2=C1C1=C(NCC=3C=C4OCOC4=CC=3)N=C(Cl)N=C1S2 GMOJSYQEVFUKKP-UHFFFAOYSA-N 0.000 description 1
• UNJUEEAMOUUCRY-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C2OCOC2=CC(CNC=2N=C(Cl)N=C3SC(=C(C3=2)C)C)=C1 UNJUEEAMOUUCRY-UHFFFAOYSA-N 0.000 description 1
• IWRLJHBMZUZYLL-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-chloro-6-(trifluoromethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C2OCOC2=CC(CNC2=C3C=C(SC3=NC(Cl)=N2)C(F)(F)F)=C1 IWRLJHBMZUZYLL-UHFFFAOYSA-N 0.000 description 1
• CHICRLRXAMHNRI-UHFFFAOYSA-N n-[2-(1,3-benzodioxol-5-yl)ethyl]-2,5-dichloro-6-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C2OCOC2=CC(CCNC=2N=C(Cl)N=C3SC(=C(C3=2)Cl)C)=C1 CHICRLRXAMHNRI-UHFFFAOYSA-N 0.000 description 1
• LQBJBUYNQLVPLN-UHFFFAOYSA-N n-[2-(1,3-benzodioxol-5-yl)ethyl]-2,6-dichlorothieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C2OCOC2=CC(CCNC2=C3C=C(SC3=NC(Cl)=N2)Cl)=C1 LQBJBUYNQLVPLN-UHFFFAOYSA-N 0.000 description 1
• FFKRMHLAQVBFNG-UHFFFAOYSA-N n-[2-(1,3-benzodioxol-5-yl)ethyl]-2-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=C2OCOC2=CC(CCNC=2N=C(Cl)N=C3SC(=C(C3=2)C)C)=C1 FFKRMHLAQVBFNG-UHFFFAOYSA-N 0.000 description 1
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• 230000018791 negative regulation of catalytic activity Effects 0.000 description 1
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