MXPA99001387A - Tienopirimidinas - Google Patents
TienopirimidinasInfo
- Publication number
- MXPA99001387A MXPA99001387A MXPA/A/1999/001387A MX9901387A MXPA99001387A MX PA99001387 A MXPA99001387 A MX PA99001387A MX 9901387 A MX9901387 A MX 9901387A MX PA99001387 A MXPA99001387 A MX PA99001387A
- Authority
- MX
- Mexico
- Prior art keywords
- pyrimidine
- thieno
- chloro
- pyridin
- methyl
- Prior art date
Links
- 239000011780 sodium chloride Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
- -1 3,4-methylenedioxy-benzylamino Chemical group 0.000 claims description 154
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene 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
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000001131 transforming Effects 0.000 claims description 3
- 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 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
- KETNZGUFRRBILK-UHFFFAOYSA-N N-(1,3-benzodioxol-5-ylmethyl)-6-chloro-2-imidazol-1-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound N1=C2SC(Cl)=CC2=C(NCC=2C=C3OCOC3=CC=2)N=C1N1C=CN=C1 KETNZGUFRRBILK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 201000011082 combat disease Diseases 0.000 claims description 2
- 239000002552 dosage form 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
- 239000007787 solid Substances 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 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
- 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
- 210000000748 cardiovascular system Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 208000008787 Cardiovascular Disease Diseases 0.000 abstract 1
- 208000010228 Erectile Dysfunction Diseases 0.000 abstract 1
- 201000001881 impotence Diseases 0.000 abstract 1
- 101710031992 pRL90232 Proteins 0.000 abstract 1
- 101710035540 plaa2 Proteins 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 99
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 98
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 97
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 94
- 238000006243 chemical reaction Methods 0.000 description 41
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 35
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 25
- FUDYRLUSXBRPIA-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-ylmethanamine Chemical compound O1CCOC2=CC(CN)=CC=C21 FUDYRLUSXBRPIA-UHFFFAOYSA-N 0.000 description 25
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 25
- DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 23
- 239000000126 substance Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 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 11
- 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 11
- 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 11
- 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 11
- 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 11
- 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 11
- YKOYVPUMJJBMBP-UHFFFAOYSA-N 4,6-dichloro-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=CN=C1 YKOYVPUMJJBMBP-UHFFFAOYSA-N 0.000 description 11
- IFISBEYDEGFLMI-UHFFFAOYSA-N 4-chloro-2-pyridin-2-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=CC=N1 IFISBEYDEGFLMI-UHFFFAOYSA-N 0.000 description 11
- NUUDPHDEZJUWDZ-UHFFFAOYSA-N 4-chloro-2-pyridin-3-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=CN=C1 NUUDPHDEZJUWDZ-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 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 11
- 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 11
- 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 11
- 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 11
- 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 11
- YFTQPWJKANFRBY-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CN=CC=N1 YFTQPWJKANFRBY-UHFFFAOYSA-N 0.000 description 11
- 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 11
- OTIFYNRGBHJTIF-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=CN=C1 OTIFYNRGBHJTIF-UHFFFAOYSA-N 0.000 description 11
- NBVIHUXALANKGR-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=CC=N1 NBVIHUXALANKGR-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 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 11
- 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 11
- 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 11
- 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 11
- 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 11
- QHFRZUWIJCIJFY-UHFFFAOYSA-N 5-[4-chloro-6-(trifluoromethyl)thieno[2,3-d]pyrimidin-2-yl]-1,2-oxazole Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=NO1 QHFRZUWIJCIJFY-UHFFFAOYSA-N 0.000 description 11
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 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 10
- 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 10
- 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 10
- RITRSKXLEDGLQP-UHFFFAOYSA-N 4-chloro-2-pyridin-4-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=NC=C1 RITRSKXLEDGLQP-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 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 10
- 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 10
- 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 10
- 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 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- CIUYJYRQKYGNQP-UHFFFAOYSA-N (3-Nitrophenyl)methanamine Chemical compound NCC1=CC=CC([N+]([O-])=O)=C1 CIUYJYRQKYGNQP-UHFFFAOYSA-N 0.000 description 9
- 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
- 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 9
- 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 9
- KLXAGVAFARUQRY-UHFFFAOYSA-N 4-chloro-2-pyrazin-2-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CN=CC=N1 KLXAGVAFARUQRY-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
- VROKTDMUCLPWTE-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=NC=C1 VROKTDMUCLPWTE-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 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 9
- 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 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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 8
- 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 8
- 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 8
- 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 8
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- BCHQHHYTBVURCM-UHFFFAOYSA-N 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC([N+](=O)[O-])=CC2=C1Cl BCHQHHYTBVURCM-UHFFFAOYSA-N 0.000 description 8
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Abstract
Las tienopirimidinas de la fórmula I (Ver Fórmula) y sus sales aceptables desde el punto de vista fisiológico, en donde R1, R2, R3, R3, R4, X y n tienen los significados indicados en la reivindicación 1, actúan como inhibidores de la fosfodiesterasa V .y pueden ser empleados para el tratamiento de las enfermedades del sistema cardiocirculatorio y para la terapia de los trastornos de la potencia.
Description
- - TIENOPIRIMIDINAS
DESCRIPCIÓN DE LA INVENCIÓN
La invención se refiere a los compuestos de la fórmula
en donde R1, R2 representan independientemente H, A, OA, alquenilo, alquinilo, N02, CF3 o Hal, siendo uno de los restos R1 Ó R2 siempre ? H, R1 y R2, juntos, también representan alquileno de 3 a 5 átomos de C, R3, R4 representan independientemente H, A, OA, Hal,
N02, NH2, NHA o NAA' , R3 Y R4 juntos, también representan -0-CH2-CH2-, -0-CH2- 0- ó -0-CH2-CH2-0-, A, A' representan independientemente alquilo de 1 a 6
Ref. 29270 - - átomos de C, X representa un heterociclo insaturado de 5 a 7 miembros, que puede estar no sustituido o mono, di o trisubstituido con A, Hal o CF3, que contiene de 1 a 4 átomos de N, 0 y/o S y en el que otros grupos de CH2 también pueden estar reemplazados por NH, NA, S u 0, y que se encuentra unido a través del N o C, Hal representa F, Cl, Br o I y n es 0, 1, 2 ó 3, y a sus sales aceptables desde el punto de vista fisiológico . Los derivados de la pirimidina se conocen, por ejemplo, de la patente europea n° 201.188 o de la patente mundial n° 93/06104. El objetivo de la invención era el de desarrollar nuevos compuestos con propiedades valiosas, en particular compuestos que puedan ser empleados en la elaboración de medicamentos. Se descubrió que los compuestos de la fórmula I y sus sales se toleran bien y poseen propiedades farmacológicas muy valiosas. En particular, estos compuestos muestran una inhibición especifica de la GMPc-fosfodiesterasa (FDE V) .
Las quinazolinas con una actividad inhibidora de la
GMPc-fosfodiesterasa se describen, por ejemplo, en J.
Med. Chem. 36, pág. 3765 (1993) y en ibid. 37' Pá9- 2106
(1994) . La actividad biológica de los compuestos de la fórmula I puede ser determinada, por ejemplo, de acuerdo a los métodos descriptos en la patente mundial n° 93/06104. La afinidad de los compuestos de la invención por la GMPC- y AMPc-fosfodiesterasa se determina por medio de los valores IC50 (concentración del inhibidor necesaria para alcanzar un 50% de inhibición de la actividad enzimática) . Las determinaciones se pueden llevar a cabo de acuerdo a métodos conocidos y empleando enzimas aisladas
(p. ej . W. J. Thompson y col., Biochem 1971, H), pág.
311) . Para llevar a cabo los ensayos se puede emplear un método "batch" modificado de . J. Thompson y M. M.
Appleman (Biochem. 1979, 18, pág. 5228) . Por lo tanto, los compuestos se adecúan para el tratamiento de enfermedades del sistema cardiocirculatorio, en particular de la insuficiencia cardiaca, y para la terapia de los trastornos de la potencia. Los compuestos de la fórmula I pueden ser empleados en la medicina y veterinaria en calidad de sustancias activas de los medicamentos. También pueden ser empleados en calidad de productos intermedios en la preparación de otras sustancias activas de medicamentos. En consecuencia, son objeto de la invención los compuestos de la fórmula I y también un procedimiento para preparar a) compuestos de la fórmula I, según la reivindicación
1, y sus sales, en donde X se encuentra unido a través del N, caracterizado porque se hace reaccionar un compuesto la fórmula II
en donde R1, R2, R3, R4 y n tienen los significados indicados, y L representa Cl, Br, OH, SCH3 o un grupo OH esterificado y reactivo, con un heterociclo insaturado de 5 a 7 miembros que puede estar no sustituido o mono, di o trisubstituido con A, Hal o CF3, que tiene al menos un grupo de NH y en el que otros grupos de CH2 también pueden estar reemplazados por NH, NA, S u 0, b) compuestos de la fórmula I, según la reivindicación 1 y sus sales, en donde X se encuentra unido a través del C, caracterizado porque se hace reaccionar un compuesto de la fórmula III,
en donde R1, R2 y X tienen los significados indicados y L representa Cl, Br, OH, SCH3 o un grupo OH esterificado y reactivo, con un compuesto de la fórmula IV
en donde - -R3, R4 y n tienen los significados indicados, o c) porque en un compuesto de la fórmula I se transforma un resto R1, R2, R3 y/o R4 en otro resto R1, R2, R3 y/o R4, ya sea reduciendo un grupo nitro, acilando un grupo de amino primario o secundario o transformándolo por aminación reductiva en una amina alquilada, y/o porque se transforma un compuesto básico de la fórmula I en una de sus sales por tratamiento con un ácido . Los restos R1, R2, R3, R4, X, L y n que aparecen en este texto tienen los significados indicados para las fórmulas I, II, III, IV y V, salvo indicación contraria. A y A' representan, independientemente uno del otro, preferentemente alquilo de 1 a 6 átomos de C. En las fórmulas indicadas, el resto de alquilo tiene preferentemente una cadena recta de 1, 2, 3, 4, 5 ó 6 átomos de C, preferentemente de 1, 2, 3, 4 ó 5 átomos de C, y representa preferentemente metilo, etilo o propilo, luego preferentemente isopropilo, butilo, isobutilo, sec-butilo o terbutilo, pero también n-pentilo, neopentilo o isopentilo. El alquileno es preferentemente de cadena recta y representa preferentemente propileno, butileno o - -pentileno. Uno de los restos R1 o R2 representa preferentemente
H, mientras que el otro representa preferentemente propilo o butilo, pero, en particular, preferentemente etilo o metilo. R1 y R2, juntos, también representan preferentemente propileno, butileno o pentileno. Hal representa preferentemente F, Cl o Br, pero también I. Alquenilo representa preferentemente vinilo, 1- ó 2-propenilo, 1-butenilo, isobutenilo, sec-butenilo, luego preferentemente 1-pentenilo, isopentenilo ó 1-hexenilo. Alquinilo representa preferentemente etinilo, propin-1-ilo, luego butin-1-ilo, butin-2-ilo, pentin-1-ilo, pentin-2-ilo o pentin-3-ilo. Los restos R3 y R4 pueden ser iguales o diferentes y se encuentran preferentemente en la posición 3 ó 4 del anillo de fenilo. Por ejemplo, representan independientemente H, alquilo, alcoxi, nitro, amino, alquilamino tal como, por ejemplo, metilamino, dialquilamino tal como, por ejemplo, dimetilamino, F, Cl,
Br o I, o bien representan juntos etilenoxi, metilendioxi o etilendioxi. Cada cual también puede representar independientemente alcoxi tal como, por ejemplo, metoxi, etoxi o propoxi. El resto X representa preferentemente 2- ó 3-furilo, 2- ó 3-tienilo, 1-, 2- ó 3-pirrolilo, 1-, 2-, 4-ó 5-imidazolilo, 2-metil-l-imidazol-l-ilo, 1-, 3-, 4- ó
-pirazolilo, 2-, 4- ó 5-oxazolilo, 3-, 4- ó 5-isoxazolilo, 2-, 4- ó 5-tiazolilo, 3-, 4- ó 5-isotiazolilo, 2-, 3- ó 4-piridilo, 2-, 4-, 5-alquilo, Hal o CF3, luego preferentemente 1,2, 3-triazol-l-, 4- ó -5-ilo, 1, 2, 4-triazol-l-, -3- ó -5-ilo, 1- ó 5-tetrazolilo,
1, 2, 3-oxadiazol-4- ó -5-ilo, 1, 2, -oxadiazol-3- ó -5-ilo,
1, 3, 4-tiadiazol-2- ó -5-ilo, 1, 2, 4-tiadiazol-3- ó -5-ilo, 1, 2, 3-tiadiazol-4- ó -5-ilo, '3- ó 4-piridazinilo o pirazinilo. Todos los restos que aparecen reiteradas veces en la presenta invención pueden ser iguales o diferentes, es decir, son independientes entre si. En consecuencia, constituyen un objeto particular de la invención aquellos compuestos de la fórmula I en los cuales al menos uno de los restos mencionados tiene uno de los significados preferidos que se han indicado anteriormente. Se pueden representar algunos grupos preferidos de compuestos mediante las fórmulas parciales la a le que se indican a continuación, que responden" a la fórmula I y en las cuales los restos que no se detallan explícitamente tienen el significado indicado para la fórmula I, a saber: en la X representa imidazolilo o piridinilo;
en Ib R1, R2 representan independientemente H, A, OA, N02, CF3 o Hal, siendo al menos uno de los restos R1 o R2 siempre ? de H, R3 y R4, juntos, representan -0-CH2-CH2-, -0-CH2-0- ó -0-CH2-CH2-0, describen en la literatura (por ejemplo, en ciertos trabajos como el de Houben-Weyl, "Methoden der organischen Chemie, (Métodos de la Química Orgánica) , Georg-Thie e-Verlag, Stuttgart) y en condiciones de reacción que son conocidas y adecuadas para las reacciones mencionadas. También se puede hacer uso de variantes conocidas de estos métodos que no se detallan en este texto. En los compuestos de las fórmulas II, III y IV, los restos R1, R2, R3, R4, X y n tienen los significados indicados, en particular, tienen los significados preferidos que se han indicado anteriormente. Cuando L representa un grupo de OH esterificado y reactivo, dicho grupo es preferentemente alquilsulfoniloxi de 1 a 6 átomos de C (preferentemente metilsulfoniloxi) o arilsulfoniloxi de 6 a 10 átomos de C
(preferentemente fenilsulfoniloxi o p-tolilsulfoniloxi, luego también 2-naftalenosulfoniloxi) .
- - Si se desea, los materiales de partida se pueden preparar in situ, pero de manera tal que en lugar de aislarlos de la mezcla de reacción se los hace reaccionar directamente para formar los compuestos de la fórmula I . De lo contrario, también es posible llevar a cabo la reacción en etapas. Los compuestos de la fórmula I, en los cuales X se encuentra unido a través del N al sistema del anillo de tienopirimidina, se pueden preparar preferentemente por reacción de compuestos de la fórmula II con un heterociclo insaturado de 5 a 7 miembros que puede estar no sustituido o mono, di o trisubstituido con A, Hal o CF3, que tiene al menos un grupo de NH y en el que otros grupos de CH2 también pueden estar reemplazados por NH, NA, S u 0. Los compuestos de partida de la fórmula II son conocidos en parte. En caso de no ser conocidos se pueden preparar de acuerdo a métodos en si conocidos. Los compuestos previos de los compuestos de la fórmula - II pueden ser obtenidos, por ejemplo, por ciclación y halogenación según se describe en J." Med. Chem. 24, pág. 374 (1981) . Los compuestos de la fórmula II se obtienen por reacción subsiguiente con arilalquilaminas . En particular, la reacción de los compuestos de la fórmula II con el heterociclo que contiene un grupo de NH se lleva a cabo en presencia o en ausencia de un disolvente inerte y a temperaturas comprendidas entre aprox. -20 y aprox. 150°, preferentemente entre 20 y 100°. Conviene agregar un agente capturador del ácido, por ejemplo, un hidróxido, carbonato o bicarbonato de metal alcalino o alcalinotérreo u otra sal de un ácido débil y un metal alcalino o alcalinotérreo, preferentemente de una sal de potasio, sodio, calcio o cesio. También puede ser conveniente el agregado de una base orgánica tal como la trietilamina, dimetilanilina, piridina o quinoleina, o bien de un exceso del componente de amina. En calidad de disolvente inerte se adecúan, por ej . , los hidrocarburos tales como el hexano, éter de petróleo, benceno, tolueno o xileno; los hidrocarburos clorados tales como el tricloroetileno, 1, 2-dicloroetano, tetracloruro de carbono, cloroformo o diclorometano; los alcoholes tales como el metanol, etanol, isopropanol, n-propanol, n-butanol o terbutanol; los éteres tales como el éter dietilico, diisopropilico, tetrahidrofurano (THF) o dioxano; los glicoléteres tales como el etilenglicolmonometiléter ¡.metilglicol) , el etilen-glicolmonoetiléter (etilglicol) o el etilen- - -glicoldimetiléter (diglime) ; las cetonas tales como la acetona o la butanona; las amidas tales como la acetamida, dimetilacetamida o la dimetilformamida (DMF) ; los nitrilos tales como el acetonitrilo; los sulfóxidos tales como el dimetilsulfóxido (DMSO) ; los nitrocompuestos tales como el nitrometano o nitrobenceno; los esteres tales como él acetato de etilo o las mezclas de los disolventes mencionados. Los compuestos de la fórmula I, en los cuales X se encuentra unido a través del C "al sistema del anillo de tienopirimidina, se pueden obtener por reacción de compuestos de la fórmula III con compuestos de la fórmula IV. Por lo general, los compuestos de partida de la fórmula IV y V son conocidos. En caso de no ser conocidos se pueden preparar de acuerdo a métodos en si conocidos.
Los compuestos de la fórmula III se pueden preparar, por ejemplo, por reacción de POCL3 con compuestos obtenidos a partir de derivados del tiofeno y heterociclos sustituidos con CN (Eur. J. Med. Chem., 23, pág. 453 (1988) . La reacción de los compuestos de la fórmula III con los compuestos dé fórmula IV se lleva a cabo en condiciones similares, en lo que respecta al tiempo de reacción, temperatura y disolvente, a las empleadas para - 1 -la reacción de los compuestos de la fórmula II con los heterociclos que contienen NH. También es posible transformar en un compuesto de la fórmula I un resto R3 y/o R4 en otro resto R3 y/o R4 ya sea, por ejemplo, reduciendo grupos nitro (por ejemplo, por hidrogenación con niquel-Raney o Pd sobre carbón en un disolvente inerte como el metanol o el etanol) a grupos de amino o hidrolizando grupos ciano a grupos de
COOH. También se pueden acilar de manera usual los grupos de amino libres con un cloruro o anhídrido de ácido, o bien alquilar con un halogenuro de alquilo sustituido o no sustituido. Estas reacciones se llevan a cabo convenientemente en un disolvente inerte tal como el diclorometano o THF y/o en presencia de una base como la trietilamina o la piridina y a temperaturas comprendidas entre -60 y +30. Una base de la fórmula I se puede convertir en su sal por adición de un ácido, por ejemplo, haciendo reaccionar cantidades equivalentes de la base y del ácido en un disolvente inerte como el etanol y ' luego concentrando por evaporación. Para esta reacción hay que tener particularmente en cuenta los ácidos que forman sales aceptables desde el punto de vista fisiológico. Por lo tanto, se pueden emplear los ácidos inorgánicos - -como, por ejemplo, el ácido sulfúrico, el ácido nítrico, los hidrácidos tales como el ácido clorhídrico o bromhídrico, los ácidos fosfóricos tales como el ácido ortofosfórico, el ácido sulfámico, y también los ácidos orgánicos, en particular, los ácidos carboxílicos, sulfónicos o sulfúricos mono o polibásicos alifáticos, alicíclicos, aralifáticos, aromáticos o heterocíclicos como, por ejemplo, el ácido fórmico, acético, propiónico, piválico, dietilacético, malónico, succínico, pimélico, fumárico, maleico, láctico, tartárico, málico, cítrico, glucónico, ascórbico, nicotínico, isonicotínico, metanosulfónico o etanosulfónico, etanodisulfónico, 2-hidroxietanosulfónico, bencenosulfónico, p-toluenosulfónico, naftalendisulfónico y naftalenmonosulfónico, laurilsulfúrico. Las sales de ácidos no aceptables desde el punto de vista fisiológico, por ejemplo los picratos, pueden ser empleadas para aislar y/o purificar los compuestos de la fórmula I. Si se desea, también se pueden liberar las bases de la fórmula I de sus sales, empleando para ello bases como, por ejemplo, hidróxido o carbonato de sodio o potasio. Otro objeto de la presente invención es el empleo de los compuestos de la fórmula I y/o de sus sales aceptables desde el punto de vista fisiológico en la - -elaboración de preparaciones farmacéuticas, en particular por métodos no químicos. De esta manera se pueden llevar estos compuestos a una forma de dosificación adecuada junto con al menos un excipiente o producto auxiliar sólido, líquido y/o semilíquido y eventualmente en combinación con una o . varias sustancias activas diferentes . Otro objeto de la invención son los medicamentos de la fórmula I y sus sales aceptables desde el punto de vista fisiológico que actúan " como inhibidores de la fosfodiesterasa V. También son objeto de la invención las preparaciones farmacéuticas que contienen al menos un compuesto de la fórmula I y/o una de sus sales aceptables desde el punto de vista fisiológico. Estas preparaciones pueden ser empleadas en la medicina y la veterinaria en calidad de medicamentos. Entre los excipientes se pueden nombrar las sustancias orgánicas o inorgánicas que se adecúan para la administración enterar (p. ej . oral), parenteral o para la aplicación tópica y que no reaccionan con los nuevos compuestos, por ejemplo, el agua, los aceites vegetales, los alcoholes bencílicos, los alquilenglicoles, los polietilenglicoles, el triacetato de glicerina, la gelatina, los hidratos de carbono tales como la lactosa y - -el almidón, el estearato de magnesio, el talco, la vaselina. Para la administración por vía oral se emplean principalmente las tabletas, pildoras, grageas, cápsulas, polvos, granulados, jarabes, jugos o gotas, para la administración por vía rectal los supositorios, para la administración parenteral las soluciones, preferentemente las soluciones aceitosas o acuosas, también las suspensiones, emulsiones o implantes, y para la aplicación tópica los ungüentos, cremas o polvos. Los nuevos compuestos también se pueden liofilizar y los productos liofilizados, así obtenidos, pueden ser empleados, por ejemplo, para la elaboración de preparados inyectables. Las preparaciones mencionadas pueden estar esterilizadas y/o contener sustancias auxiliares tales como lubricantes, conservantes, estabilizantes y/o agentes humectantes, agentes emulsionantes, sales para influenciar la presión osmótica, sustancias reguladoras del pH, colorantes, sabores y/o una o varias sustancias activas diferentes como, por ejemplo, una o varias vitaminas. Los compuestos de la fórmula I y sus sales aceptables desde el punto de vista fisiológico pueden ser empleados para combatir enfermedades en las cuales un aumento del nivel de GMPC (monofosfato de guanosina cíclico) detiene o evita la inflamación y relaja los - -músculos. En particular, estos compuestos pueden ser empleados para el tratamiento de enfermedades del sistema cardiocirculatorio y para la terapia de los trastornos de la potencia. Todas las temperaturas que se indican en este texto están dadas en °C. En los ejemplos que siguen, la expresión "se trabaja o trata de manera usual" significa lo siguiente: en caso necesario, se agrega agua, se ajusta eventualmente el pH a valores comprendidos entre 2 y 10 según la constitución del producto final, se extrae con acetato de etilo o diclorometano, se separan las fases, se seca la fase orgánica sobre sulfato de sodio, se concentra por evaporación y se purifica por cromatografía sobre gel de sílice y/o por recristalización. Espectrometría de masa (EM) : El (ionización por impacto electrónico) : M+ FAB (bombardeo rápido de átomos; "Fast Atom Bombardment") : (M+H)+
Ejemplo 1 - - A una solución de 3.29 g de 2, 4-dicloro-6-metil-tieno- [2, 3-d]-piriinidina en 80 ml de diclorometano se agregan 3.02 g de 3, 4-metilendioxibencilamina ("A"), y después de agregar 1.52 g de trietilamina se agita - -durante 12 horas a temperatura ambiente. Se separa el disolvente y se trabaja la mezcla de manera usual. Se obtienen 3.38 g de 2-cloro-6-metil4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina, p.f. 162°. De manera análoga se obtiene, por reacción de "A" con 2, 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (3, 4-metilendioxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4- (3, 4-metilendioxi- bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina, p.f. 222°; con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (3, 4-metilendioxi- bencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclohepteno-4- (3, 4-metilendioxi- bencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [ 2 , 3-d] -pirimidina, la 2-cloro-6-etil-4- (3, 4-metilendioxibencilamino) - tieno- [2, 3-d] -pirimidina, p.f. 148°; con 2, 4, 6-tricloro-tieno- [2, 3-d] -pirimidina, - - la 2, 6-dicloro-4- (3, 4-metilendioxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2,4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2, 5-dicloro-6-metil-4- (3, 4-metilendioxibencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-nitro-4- (3, 4-metilendioxibencilamino) tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4- ("3, 4-metilendioxibencil- amino) -tieno- [2, 3-d] -pirimidina; con -2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-trifluorometil-4- (3, 4-metilendioxi- bencilamino) -tieno- [2 , 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 3-cloro-4-metoxi-bencilamina con 2, 4-dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4- (3-cloro-4-metoxibencilamino) tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (3-cloro-4-metoxibencilamino) tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, - - la 2-cloro-5, 6, 7, 8-tetrahidro-4- (3-cloro-4-metoxi- bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (3-cloro-4- metoxibencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclohepteno-4- (3-cloro-4- metoxibencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-etil-4- (3-cloro-4-metoxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2,4, 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4- (3-cloro-4-metoxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2, 5-dicloro-6-metil-4- (3-cloro-4-metoxibencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-nitro-4- (3-cloro-4-metoxibencilamit?o) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4- (3-cloro-4-metoxibencil- amino) -tieno- [2, 3-d] -pirimidina;
- -con 2, 4-dicloro-6-trifluorometil-tieno- [2 , 3-d] -pirimidina, la 2-cloro-6-trifluorometil-4- (3-cloro-4- metoxibencilamino) -tieno- [2 , 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 3,4-dimetoxi-bencilamina con 2, 4-dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4- (3, 4-dimetoxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (3, 4-dimetoxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4- (3, 4-dimetoxi- bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (3, 4-dimetoxibencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclohepteno-4- (3, 4-dimetoxibencil- amino) -tieno- [2 , 3-d] -pirimidina; con 2, -dicloro-6-etil-tieno- [ 2 , 3-d] -pirimidina, - - la 2-cloro-6-etil-4- (3, 4-dimetoxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2,4, 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4- (3, 4-dimetoxibencilamino) -tieno- [2 , 3-d] -pirimidina; con 2,4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2 , 5-dicloro-6-metil-4- (3, 4-dimetoxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-nitro-4- (3, 4-dimetoxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil -tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-trifluorometil-4- (3, 4-dimetoxibencil- amino) -tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de la bencilamina con 2, 4-dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4-bencilamino-tieno- [ 2 , 3-d] - pirimidina; con 2, 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, - 2 - la 2-cloro-5-metil-4-bencilamino-tieno- [2, 3-d] - pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4-bencilamino- [1]- benzotieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4-bencilamino-tieno- [2, 3-d] -pirimidina; con 2, -dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclohepteno-4-bencilamino-tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-etil-4-bencilamino-tieno- [2, 3-d] - pirimidina; con 2,4, 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4-bencilamino-tieno- [2, 3-d] - pirimidina; con 2, 4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina,' ~ la 2, 5-dicloro-6-metil-4-bencilamino-tieno- [2, 3-d] - pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, - - la 2-cloro-6-nitro-4-bencilamino-tieno- [ 2 , 3-d] - pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4-bencilamino-tieno- [2, 3-d] pirimidina; con 2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-trifluorometi1-4-bencilamino-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 4-fluorobencilamina con 2, -dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina, con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4- (4-fluorobencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; con 2, -dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (4-fluorobencil- amino) -tieno- [2, 3-d] -pirimidina;
- -con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] • pitimidina, la 2-cloro-5, 6-ciclohepteno-4- (4-fluorobencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-etil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; con 2,4, 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4- (4-fluorobencilamino) -tieno- [2, 3- d] -pirimidina; con 2,4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2, 5-dicloro-6-metil-4- (4-fluorobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, -dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-nitro-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4- (4-fluorobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-trifluorometil-4- (4-fluorobencil- amino) -tieno- [2, 3-d] -pirimidina . De manera análoga se obtiene, por reacción de 3,4-diclorobencilamina - -con 2, 4-dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4- (3, 4-diclorobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, -dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (3, 4-diclorobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4- (3, 4-diclorobencil- amino) - [1] -benzotieno-'[2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (3, 4-diclorobencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclohepteno-4- (3, 4-diclorobencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-etil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; con 2,4, 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, - - la 2, 5-dicloro-6-metil-4- (3, 4-diclorobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-nitro-4- (3, -diclorobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4- (3, 4-diclorobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-trifluorometil-4- (3, 4-diclorobencil- amino) -tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de la 3-nitrobencilamina con 2, 4-dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4- (3-nitrobencil- amino) - [1] -benzotieno- [2, 3-d] -pirimidina;
con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (3-nitrobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclohepteno-4- (3-nitrobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-etil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4, 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4- (3-nitrobencilamino) -tieno- [2,3- d] -pirimidina; con 2, 4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2, 5-dicloro-6-metil-4- (3-nitrobencilamino) - tieno- [ 2 , 3-d] -pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-nitro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidiná, la 2-cloro-5, 6-dimetil-4- (3-nitrobencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, - - la 2-cloro-6-trifluorometil-4- (3-nitrobencilamino) - tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 3,4-metilendioxifenetilamina con 2, 4-dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4- (3, 4-metilendioxifenetil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (3, 4-metilendioxifenetil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4- (3, 4- metilendioxifenetil-amino) - [1] -benzotieno- [2, 3- d] -pirimidina; con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (3, 4-metilendioxi- fenetilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, • - la 2-cloro-5, 6-ciclohepteno-4- (3, 4-metilendioxi- fenetila ino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [2 , 3-d] -pirimidina, - - la 2-cloro-6-etil-4- (3, 4-metilendioxifenetilamino) - tieno- [2, 3-d] -pirimidina; con 2,4, 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4- (3, 4-metilendioxifenetilamino) - tieno- [2, 3-d] -pirimidina; con 2,4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2, 5-dicloro-6-metil-4- (3, 4-metilendioxifenetil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-nitro-4- (3, -metilendioxifenetil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4- (3, 4-metilendioxifenetil- amino) -tieno- [2, 3-d] -pírimidina; con 2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-trifluorometil-4- (3, 4-metilendioxi- fenetilamino) -tieno- [2, 3-d] -pirimidina . De manera análoga se obtiene, por reacción de 3,4-etilendioxibencilamina con 2, 4-dicloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-metil-4- (3, 4-etilendioxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2 , 4-dicloro-5-metil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5-metil-4- (3, 4-etilendioxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2 , 3-d] -pirimidina, la 2-cloro-5, 6, 7, 8-tetrahidro-4- (3, 4-etilendioxi- bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclopenteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclopenteno-4- (3, 4-etilendioxi- bencilamino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-ciclohepteno- [1] -benzotieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-ciclohepteno-4- (3, 4-etilendioxi- bencila ino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-etil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-etil-4- (3, 4-etilendioxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2, , 6-tricloro-tieno- [2, 3-d] -pirimidina, la 2, 6-dicloro-4- (3, 4-etilendioxibencilamino) - tieno- [2, 3-d] -pirimidina; con 2,4, 5-tricloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2, 5-dicloro-6-metil-4- (3, 4-etilendioxibencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-nitro-tieno- [2, 3-d] -pirimidina, - - la 2-cloro-6-nitro-4- (3, 4-etilendioxibencil- amino) tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2-cloro-5, 6-dimetil-4- (3, 4-etilendioxibencil- amino) -tieno- [2, 3-d] -pirimidina; con 2, 4-dicloro-6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2-cloro-6-trifluorometil-4- (3, 4-etilendioxi- bencilamino) tieno- [2, 3-d] -pirimidina.
Ejemplo 2 Durante 5 horas se calientan a 150° 1.67 g de 2-cloro-6-metil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina, 1.02 g de imidazol y 2 g de fenol. Después de enfriar se disuelve el residuo en diclorometano y se trabaja la solución de manera usual. Se obtiene 1.0 g de 2- (imidazoll-il) -6-metil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] pirimidina, p.f. 248-250°. Los compuestos que se indican a continuación se obtienen por reacción análoga del imidazol con- los derivados de la 2-cloro-tieno- [2, 3-d] -pirimidina que se han obtenido en el ejemplo 1 y que se encuentran sustituidos en posición 4 con un grupo de arilalquilamino.
- -2- (imidazol-1-il) -5-metil-4- (3, 4-metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina, p. f .238° ; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-metilendioxi-bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina, p. f .218°; 2- (imidazol-1-il) -5, 6-ciclopenteno-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina, p. f .260°; 2- (imidazol-1-il) -5, 6-ciclohepteno-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina, p. f .210° ; 2- (imidazol-1-il) -6-etil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina, metanosulfonato, p.f.201°; 2- (imidazol-1-il) -6-cloro-4- (3, 4-metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-nitro-4- (3, 4-metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4- (3, 4-metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina, p.f. 245°; 2- (imidazol-1-il) -6-trifluorometil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-metil-4- (3-cloro-4-metoxibencil- " amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-metil-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2-(imidazol-l-il)-5, 6,7, 8-tetrahidro-4-(3-cloro-4- - -metoxibencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina;
2- (imidazol-1-il) -5, 6-ciclopenteno-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclohepteno-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-etil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-cloro-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-nitro-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-trifluorometil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-metil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-metil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, -dimetoxi-bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclopenteno-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina;
- -2- (imidazol-1-il) -5, 6-ciclohepteno-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-etil-4- (3, 4-dimetoxibencilamino) -tieno [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-cloro-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4- (3, 4-dimetoxibencil-amino) tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-nitro-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-trifluorometil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina, p.f. 207°; 2- (imidazol-1-il) -5-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4-bencilamino- [1]-benzotieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclopenteno-4-bencilamino-tiéno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclohepteno-4-bencilamino-tieno- [2, 3-d] -pirimidina, p.f. 197°;
2- (imidazol-1-il) -6-etil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-cloro-4-bencilamino-tieno- [2, 3-d] pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4-bencilamino-tieno- [2, 3-d] -piriminina 2- (imidazol-1-il) -6-nitro-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-trifluorometil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (4-fluorobencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclopenteno-4- (4-fluorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclohepteno-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-etil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina, p.f. 199°;
- -2- (imidazol-1-il) -6-cloro-4- (4-flucrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4- (4-fluorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-nitro-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-trifluorometil-4- (4-fluorobencil-amino) -tieno- [2, 3-d] -pirimidina;' 2- (imidazol-1-il) -6-metil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-metil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-dicloro-bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclopenteno-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclohepteno-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-etil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-cloro-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (imidazol-1-il) -5-cloro-6-metil-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-nitro-4- (3, -diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4- (3, 4-diclorobencilamino) tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-trifluorometil-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-metil-4- (3-nitrobencilamino) -tieno-[2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-metil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3-nitrobencil-amino) - [ 1 ] -benzotieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclopenteno-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclohepteno-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-etil-4- (3-nitrobencilamino) -tieno-[2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-cloro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4- (3-nitrobencilamino) tieno- [2, 3-d] -pirimidina;
- -2- (imidazol-1-il) -6-nitro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-trifluorometil-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-metil-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-metil-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina;' 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-metilendioxi-fenetilamino) - [ 1 ] -benzotieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclopenteno-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclohepteno-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-etil-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-cloro-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4- (3, -metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-nitro-4- (3, 4-metilendioxifenetil-a ino) -tieno- [2, 3-d] -pirimidina;
- -2- (imidazol-1-il) -5, 6-dimetil-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-trifluorometil-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-metil-4- (3, -etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-metil-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-etilendioxi-bencilmino) - [ 1 ] -benzotieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclopenteno-4- (3, 4-etilendioxi-bencilmino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-ciclohepteno-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (ímidazol-1-il) -6-etil-4- (3, 4-etilendioxibencil«amino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-cloro-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5-cloro-6-metil-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -6-nitro-4- (3, 4-etilendioxibencilamíno) -tieno- [2, 3-d] -pirimidina; 2- (imidazol-1-il) -5, 6-dimetil-4- (3, 4-etilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina;
2- (imidazol-1-il) -6-trifluorometil-4- (3, 4-etilendioxi-bencili ino) -tieno- [2, 3-d] -pirimidina. Los compuestos que se indican a continuación se obtienen por reacción análoga del pirazol con los derivados de la 2-cloro-tieno- [2, 3-d] -pirimidina que se han obtenido en el ejemplo 1 y que se encuentran sustituidos en la posición 4 con un grupo de arilalquilamino . 2- (pirazol-1-il) -5-metil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-metilendioxi-bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina, p.f .210°;
2- (pirazol-1-il) -5, 6-ciclopenteno-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclohepteno-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina;
2- (pirazol-1-il) -5, 6-dimetil-4- (3, 4-metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-trifluorometil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6,7, 8-tetrahidro-4- (3-cloro-4-metoxibencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina;
2- (pirazol-1-il) -5, 6-ciclopenteno-4- (3-cloro-4-metoxi-bencilamino) -tieno- [ 2 , 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclohepteno-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (3-cloro-4-metoxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-dimetil-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimidina;
2- (pirazol-1-il) -6-trifluorometil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-metil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-metil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-dimetoxi-bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclopenteno-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina;' 2- (pirazol-1-il) -5, 6-ciclohepteno-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (3, 4-dimetoxibencilamino) -tieno [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirímidina; 2- (pirazol-1-il) -5, 6-dimetil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-trifluorometil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina;
2- (pirazol-1-il) -6-metil-4-bencilamino-tieno- [2 , 3-d] -pirimidina; 2- (pirazol-1-il) -5-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4-bencilamino- [1] -benzotieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclopenteno-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclohepteno-4-bencilamino-tieno-[2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4-bencilamino-tieno- [2, 3-d] -piriminina; 2- (pirazol-1-il) -6-nitro-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-dimetil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-trifluorometil-4-bencilamino-tienó- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina;
2- (pirazol-1-il) -5-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4- (4-fluorobencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclopenteno-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclohepteno-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4- (4-fluorobencilamino) -tieno-[2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-dimetil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-trifluorometil-4- (4-fluorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-metil-4- (3, 4-diclorobencilamino) - " tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-metil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-diclorobencil-amino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclopenteno-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclohepteno-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-dimetil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-trifluorometil-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-metil-4- (3-nitrobencilamino) -tieno-[2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-metil-4- (3-nitrobencilamino) -tieño- [2, 3-d] -piriminina 2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3-nitrobencil-a ino) - [ 1 ] -benzotieno- [2, 3-d] -pirimidina;
- -2- (pirazol-1-il) -5, 6-ciclopenteno-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclohepteno-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-dimetil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-trifluorometil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-metil-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-metil-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, -metilendioxi-fenetilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclopenteno-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (pirazol-1-il) -5, 6-ciclohepteno-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-etil-4- (3, 4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (3, -metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (3, -metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina;' 2- (pirazol-1-il) -5, 6-dimetil-4- (3, 4-metilendioxifenetil-amino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-trifluorometil-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-metil-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-metil-4- (3, 4-etilendioxibencilamino) -tieno [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-etilendioxi-bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclopenteno-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-ciclohepteno-4- (3, 4-etilendioxi-bencila ino) -tieno- [2, 3-d] -pirimidina;
- - 2- (pirazol-1-il) -6-etil-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-cloro-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5-cloro-6-metil-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -6-nitro-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (pirazol-1-il) -5, 6-dimetil-4- (3, 4-etilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina;' 2- (pirazol-1-il) -6-trifluorometil-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina. Los compuestos que se indican a continuación se obtienen por reacción análoga del 1, 2, 4-triazol con los derivados de la 2-cloro-tieno- [2, 3-d] -pirimidina que se han obtenido en el ejemplo 1 y que se encuentran sustituidos en la posición 4 con un grupo de arilalquilamino . 2- (1, 2, 4-triazol-l-il) -5-metil-4- (3, 4-metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (l,2,4-triazol-l-il)-5, 6,7, 8-tetrahidro-4- (3, 4-metilen-dioxibencilamino) - [ 1 ] -benzotieno- [2, 3-d] -pirimidina; 2- (l,2,4-triazol-l-il)-5, 6-ciclopenteno-4- (3,4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (1,2, 4-triazol-l-il) -5, 6-ciclohepteno-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-etil-4- (3, -metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-cloro-4- (3, 4-metilendioxibencil-a ino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -5-cloro-6-metil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-nitro-4- (3, 4-metilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina;" 2- (1, 2, 4-triazol-l-il) -5, 6-dimetil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -6-trifluorometil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2-(l,2,4-triazol-l-il) -6-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2-(l,2,4-triazol-l-il) -5-meti1-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6,7, 8-tetrahidro-4- (3-cloro-4-metoxibencilamino) - [ 1 ] -benzotieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6-ciclopenteno-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6-ciclohepteno-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (1,2, 4-triazol-l-il) -6-etil-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-cloro-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -5-cloro-6-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-nitro-4- (3-cloro-4-metoxibencil-amino) -tieno- [2, 3-d] -pirimídina; 2- (1, 2, -triazol-l-il) -5, 6-dimetil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d]'-pirimidina; 2- (1, 2, 4-triazol-l-il) -6-trifluorometil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -6-metil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-metil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il)-5, 6,7, 8-tetrahidro-4- (3, 4-dimetoxibencilamino) - [ 1 ] -benzotieno- [2, 3-d] -pirimidina;
2- (1,2, -triazol-1-il) -5, 6-ciclopenteno-4- (3,4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -5, 6-ciclohepteno-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-etil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina;
- -2- (1, 2, 4-triazol-l-il) -6-cloro-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-cloro-6-metil-4- (3, -dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-nitro-4- (3, -dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6-dimetil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -6-trifluorometil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-'d] -pirimidina; 2- (1, 2, -triazol-l-il) -6-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6, 7, 8-tetrahidro-4-bencilamino- [1] -benzotieno- [2, 3-d] -pirimidina; 2-(l,2,4-triazol-l-il)-5, 6-ciclopenteno-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6-ciclohepteno-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -6-etil-4-bencilamino-tieno- [2,3-d] -pirimidina; 2- (1, 2, 4-tríazol-l-il) -6-cloro-4-bencilamino-tieno- [2, 3-d] -pirimidina;
- -2- (1, 2, 4-triazol-l-il) -5-cloro-6-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-nitro-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6-dimetil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -6-trifluorometil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -5-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6, 7, 8-tetrahidro-4- (4-fluoro-bencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (triazol-1-il) -5, 6-ciclopenteno-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -5, 6-ciclohepteno-4- (4-fluoro-bencilamino) -tieno- [2, 3-d] -pirimidina; 2-(l,2,4-triazol-l-il)-6-etil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-cloro-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-cloro-6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (1, 2, 4-triazol-l-il) -6-nitro-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -5, 6-dimetil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-trifluorometil-4- (4-fluoro-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-metil-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-metil-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina;" 2- (1, 2, -triazol-l-il) -5, 6,7, 8-tetrahidro-4- (3, 4-diclorobencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina;
2- (1, 2, -triazol-l-il) -5, 6-ciclopenteno-4- (3,4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il)-5, 6-ciclohepteno-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2-(l,2,4-triazol-l-il)-6-etil-4-(3, 4-diclorobencilamino) tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-cloro-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -5-cloro-6-metil-4- (3, 4-dicloro-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -6-nitro-4- (3, 4-diclorobencil-a ino) -tieno- [2, 3-d] -pirimidina;
- 5 -2- (1, 2, 4-triazol-l-il) -5, 6-dimetil-4- (3, -diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -6-trifluorometil-4- (3, -diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-metil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-metil-4- (3-nitrobencil<amino) -tieno- [2, 3-d] -pirimidina; 2- (l,2,4-triazol-l-il)-5,6,7,8-tetrahidro-4-(3-nitrobencilamino) - [1] -benzotienó- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -5, 6-ciclopenteno-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6-ciclohepteno-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -6-etil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-cloro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -5-cloro-6-metil-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-nitro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6-dimetil-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina;
- -2- (1, 2, 4-triazol-l-il) -6-trifluorometil-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -6-metil-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 1- (1,2, 4-triazol-l-il) -5-metil-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-metilen-dioxifenetilamino) - [1] -benzotieno- [2, 3-d] -pirimidina;
2- (1, 2, 4-triazol-l-il) -5, 6-ciclopenteno-4- (3, 4-metilendioxifenetilamino) -tieno-'[2, 3-d] -pirimidina; 2- (1, 2, -triazol-l-il) -5, 6-ciclohepteno-4- (3,4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2-(l,2,4-triazol-l-il) -6-etil-4- (3, 4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2-(l,2,4-triazol-l-il) -6-cloro-4- (3, 4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-cloro-6-metil-4- (3, 4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-nitro-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -5, 6-dimetil-4- (3, 4-metilendisxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (l,2,4-triazol-l-il)-6-trifluorometil-4- (3,4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (1,2, 4-triazol-l-il) -6-metil-4- (3, 4-etilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5-metil-4- (3, 4-etilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-etilen-dioxibencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -5, 6-ciclopenteno-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1,2, 4-triazol-l-il) -5, 6-ciclohepteno-4- (3, 4-etilendioxibencilamino) -tieno- [2", 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-etil-4- (3, 4-etilendioxibencil-amipo) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-cloro-4- (3, 4-etilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, -triazol-1-il) -5-cloro-6-metil-4- (3, 4-etilen-dioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-nitro-4- (3, 4-etilendioxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (l,2,4-triazol-l-il)-5, 6-dimetil-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (1, 2, 4-triazol-l-il) -6-trifluorometil-4- (3,4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina. Los compuestos que se indican a continuación se obtienen por reacción análoga del 2-metilimidazol con los derivados de la 2-cloro-tieno- [2, 3-d] -pirimidina que se - -han obtenido en el ejemplo 1 y que se encuentran sustituidos en la posición 4 con un grupo de arilalquilamino . 2- (2-metilimidazol-l-il) -5-metil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6,7, 8-tetrahidro-4- (3, 4-metilendioxibencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina, amorfa; 2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (3, 4-metilendioxibencilamino) -tieno- ['2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-cloro-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (3, 4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (3,4-metilendioxibencilamino) -tieno- [2, 3-d] -pirimidina;
- - 2- (2-metilimidazol-l-il) -6-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6,7, 8-tetrahidro-4- (3-cloro-4-metoxibencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina;
2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d]"-pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4- (3-cloro-4-metoxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-cloro-4- (3-cloro-4-metoxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (3-cloro-4-metoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-metil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina;
2- (2-metilimidazol-l-il) -5-metil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-dimetoxibencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina;' 2- (2-metilimidazol-l-il) -6-cloro-4- (3, 4-dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (3,4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (3, 4-dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (3, -dimetoxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-metil-4-bencilamino-tienó- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina;
- -2- (2-metilimidazol-l-il) -5, 6, 7, 8-tetrahidro-4-bencilamino- [1] -benzotieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-cloro-4-bencilamino-tieno-[2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4-bencilamino-tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6, 7, 8-tetrahidro-4- (4-fluorobencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina;
2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (4-fluoro-bencila ino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (4-fluoro-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-cloro-4- (4-fluorobencilamino) tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (4-fluorobencilamino) -tieno- [2, 3-d]'-pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (4-fluorobencilamino) tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (4-fluorobencilamino) -tieno- [2, 3-d] -pirimidina, 2- (2-metilimidazol-l-il) -6-metil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-metil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6, 7, 8-tetrahidro-4- (3, 4- " diclorobencilamino) - [1] -benzotieno- [2, 3-d] -pirimídina;
2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-cloro-4- (3, 4-diclorobencil-amino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (3, 4-diclorobencil-amino) tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (3,4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (3, 4-diclorobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-metil-4- (3-nitrobencilamino) tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-metil-4- (3-nitrobencilamino) tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il)-5, 6,7, 8-tetrahidro-4- (3-nitrobencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina;
2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (2-metilimidazol-l-il) -6-etil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-cloro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (3-nitrobencil-amino) -tieno- [2, 3-d] -pirimidina;" 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-metil-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 1- (2-metilimidazol-l-il) -5-metil-4- (3, -metilendioxi-fenetilanino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6,7, 8-tetrahidro-4- (3, 4-metilendioxifenetilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (3, 4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (3,4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4- (3, 4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (2-metilimidazol-l-il) -6-cloro-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (3, 4-metilendioxifenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (3, 4-metilendioxi-fenetilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (3, -metilendioxifenetila ino) -tieno-'[2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-metil-4- (3,4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5-metil-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6,7, 8-tetrahidro-4- (3, 4-etilendioxibencilamino) - [1] -benzotieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclopenteno-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-ciclohepteno-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-etil-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-cloro-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina;
- -2- (2-metilimidazol-l-il) -5-cloro-6-metil-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-nitro-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -5, 6-dimetil-4- (3, 4-etilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina; 2- (2-metilimidazol-l-il) -6-trifluorometil-4- (3, 4-etilendioxibencilamino) -tieno- [2, 3-d] -pirimidina.
Ejemplo 3 Se disuelven 5 g de 2-amino-5-metil-3-etoxicarboniltiofeno con 2.7 g de 3-cianopiridina en 40 ml de dioxano. Luego se hace circular HCl gaseoso a través de la solución durante 5 horas. Después de trabajar el producto de manera usual se obtienen 6 g de 3, -dihidro-4-oxo-2- (piridin-3-il) -6-metil-tieno- [2, 3-d]-pirimidina. El reemplazo del grupo ceto por Cl con formación del anillo aromático de pirimidina se lleva a cabo en condiciones estándar. Durante 4 horas se calienta a ebullición una mezcla de 18 ml de P1C13 y 6 g de 3, 4-dihidro-4-oxo-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, con el agregado de 1.8 ml de N,N-dimetilanilina. Después de trabajar la mezcla de manera usual se obtienen 5 g de 4-cloro-2- - -(piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 3-cianopiridina, reacción subsiguiente con POCI3 y a partir de 2-amino-4-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4, 5, 6, 7-tetrahidro-3-etoxicarbonil-benzotiofeno, la 4-cloro-2- (piridin-3-il) -5,6,7, 8-tetrahidro- [1]- benzotieno- [2, 3-d] -pir midina, p.f. 143°; a partir de 2-amino-4, 5-ciclopenteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclohepteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; 3 partir de 2-amino-5-etil-3-etoxicarbonil-tiofeno, la 4-cloro-2-(piridin-3-il)-6-etil-tieno-[2,3-d]- pirimidina; a partir de 2-amino-5-cloro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d]- pirimidina;
a partir de 2-amino-4-cloro-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-nitro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4, 5-dimetil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3- d] -pirimidina; a partir de 2-amino-5-trifluorometil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 5-cianoisoxazol, reacción subsiguiente con P0C13 y a partir de 2-amino-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3- d] -pirimidina; a partir de 2-amino-4-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2,'3-d] - pirimidina; a partir de 2-amino-4, 5, 6, 7-tetrahidro-3-etoxicarbonil-benzotiofeno, la 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclopenteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno- tieno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclohepteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -5, 6-diclohepteno- tieno- [2, 3-d] -pirimidiha; a partir de 2-amino-5-etil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-5-cloro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3- d] -pirimidina; a partir de 2-amino-4-cloro-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-nitro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4, 5-dimetil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-trifluorometil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (isoxazol-5-il) -6-trifluorometil- tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 2-cianopirazina, reacción subsiguiente con POCI3 y a partir de 2-amino-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4, 5, 6, 7-tetrahidro-3-etoxicarbonil-benzotiofeno, la 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] - benzo-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclopenteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tleno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclohepteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-etil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-5-clorot3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4-cloro-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-nitro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4, 5-dimetil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3- d] -pirimidina; a partir de 2-amino-5-trifluorometil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (pirazin-2-il) -6-triflucrometil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 2-cianopiridina, reacción subsiguiente con POCI3 y a partir de 2-amino-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4, 5, 6, 7-tetrahidro-3-etoxicarbonil-benzotiofeno, la 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] - benzotieno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclopehteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclohepteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-etil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d]- pirimidina; a partir de 2-amino-5-cloro-3-etoxicarbonil-tiofeno,' la 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4-cloro-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-nitro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [ 2 , 3-d] - pirimidina; a partir de 2-amino-4, 5-dimetil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3- d] -pirimidina; a partir de 2-amino-5-trifluorometil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 4-cianopiridina, reacción subsiguiente con POCI3 y a partir de 2-amino-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4, 5, 6, 7-tetrahidro-3-etoxicarboníl-benzotiofeno, la 4-cloro-2-(piridin-4-il)-5, 6,7, 8-tetrahidro- [1 ] - benzo-tieno- [2, 3-d] -pirimidina;
a partir de 2-amino-4, 5-ciclopenteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-4, 5-ciclohepteno-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-etil-3-etoxicarbonil-tiofeno, la 4-cloro-2-(piridin-4-il')-6-etil-tieno-[2,3-d]- pirimidina; a partir de 2-amino-5-cloro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] - pirimidina; a partir de 2-amino-4-cloro-5-metil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; a partir de 2-amino-5-nitro-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d]- pirimidina; a partir de 2-amino-4, 5-dimetil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [ 2 , 3- d] -pirimidina;
a partir de 2-amino-5-trifluorometil-3-etoxicarbonil-tiofeno, la 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina.
Ejemplo 4 De manera análoga a la del ejemplo 1 se obtiene, por reacción de 3, 4-metilendioxibencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina, p.f. 215°; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-ciclopenteno-tieno- [ 2 , 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina;
- Íl eon 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, -metilendioxibencil- amino) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- a ino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno-[2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, -metilendioxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- a ino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- a ino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d]-pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, -metilendioxibencil- amino) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -ó-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2 , 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, -metilendioxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil-amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- (2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendiaxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-mietil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il)-4- (3, 4-metilendioxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimídina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-métil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) 5,6,7, 8-tetrahidro- [1] -benzotieno- [2,3- d] -pirimidina, p.f. 185°; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d]-pirimidina, la 2- (piridin-4-il) -4- (3, -metilendioxibencil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxibencil- amino) -6-trifluorometil-tieno- [2, 3-d]- pirimidina. De manera análoga se obtiene, por reacción de 3-cloro-4-metoxi-bencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina;
con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2 , 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amíno) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- «amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-cloro-4-metoxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con '4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina;
con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] • pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-cloro-4-metoxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina;
con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [ 2 , 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-nitro-tieno- [2 , 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d]-pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- a ino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) 5, , 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina;
con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-cloro-4-metoxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con '4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) 5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina;
con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -5, 6-di-meti.l-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-cloro-4-metoxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina. De manera análoga se obtiene, por reacción de 3,4-dimetoxi-bencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-dimetoxibencilamino) -6- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-djpirimidina, la 2- (piridin-3-il) -4- (3, 4-dimetoxibencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, -dimetoxibencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-dimetoxibencilamino) -6- etiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina la 2- (piridin-3-il) -4- (3, 4-dimetoxibencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, -dimetoxibencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, -dimetoxibencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, -dimetoxibencilamino) - 5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-dimetoxibencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diptetoxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-cíclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) -6- etil-tieno- [2, 3-d] -pir'imidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamirió) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pírimidina, la 2- (isoxazol-5-il) -4- (3, 4-dimetoxibencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d]-pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) -6- nitrotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, - - la 2- (pirazin-2-il) -4- (3, -dimetoxibencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) -6- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) -5- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) -6- nitrotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-dimetoxibencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1]-benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) - 5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d]-pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -?-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) - 5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-dimetoxibencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de bencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d]-pirimidina, la 2- (piridin-3-il) -4-bencilamino-6-metil-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-5, 6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, p.f. 189°; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-5, 6-ciclopenteno- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-5, 6-ciclohepteno- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-6-cloro-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d]-pirimidina, la 2- (piridin-3-il) -4-bencilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-bencilamino-6-trifluorometil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-5-metil-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxatol-5-il) -4-bencilamino-5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-5, 6- ciclopentenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno-[2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-5, 6- cicloheptenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] • pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-bencilamino-6-trifluoro- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-5, 6-ciclopenteno- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-5, 6-ciclohepteno- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencílamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] - ' pirimidina, la 2- (pirazin-2-il) -4-bencilamino-6-nitro-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d]-pirimidina, la 2- (pirazin-2-il) -4-bencilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-bencilamino-6-trifluorometil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5,6,7, 8-tetrahidro- [1] -benzo-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-5, 6, 7, 8- tetrahidro- [ 1 ] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-5, 6-ciclopenteno- tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2,3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-5, 6-ciclohepteno- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d]-pirimidina, la 2- (piridín-2-il) -4-bencilamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-bencilamino-6-trifluorometil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d]-pirimídina, la 2- (piridin-4-il) -4-bencilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-5, 6, 7, 8- tetrahidro- [1 ] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-5, 6-ciclopenteno- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; la 2- (piridin-4-il) -4-bencilamino-5, 6-ciclohepteno- tieno-[2,3- d] -pirimidina, con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2 , 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-6-etil-tieno- [2, 3-d] -piridina, con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencil.amino-5-cloro-6-m.etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2 , 3-d] -pirimidina, la 2- (piridin-4-il) -4-bencilamino-6-trifluorometil- tieno- [2, 3-d] -pirimidina.
De manera análoga se obtiene, por reacción de 4-fluorobencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -5- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) - 5,6,7, 8-tetra-hidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclo-oenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fuorobencilamino) -6-etil) - tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (4-fluorobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (4-fluorobencilamino) -6- trifuorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il ) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -5- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) - 5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -6-etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (4-fluorobenciamino) -6- trifluoro-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -6- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -5- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) - 5, 6, 7, 8-tetra-hidro- [1] -benzotieno- [2, 3-d]- pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -6-etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-2-il) -4- (4-fluorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (4-fluorobencilamino) -6- trifluoromeil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -6- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -5- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) - 5,6,7,8- tetra-hidro-[l]- tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-4-il) -4- (4-fluorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -6-etil- tieno- [2, 3-d] -pirimidína; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -6- " nitrotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-4-il) -4- (4-fluorobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (4-fluorobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 3,4-diclorobencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il ) -5-meti1-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) - 5, 6, 7, 8-tetrahidro- [ 1 ] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il ) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -5, 6- di-metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-diclorobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con -cloro-2- (isoxazol-5-il) -5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, -diclorobencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d]-pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2 , 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4 (3, 4-diclorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) - 5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-diclorobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2 - (pirazin-2-il) -4- (3, 4-diclorobencilamino) -6- etiltieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -5, 6- di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-diclorobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] -' pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -5- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) - 5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-dJ - pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, -diclorobencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d]-pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-diclorobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -' -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -5- metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il).-5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, -diclorobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-til-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -6- etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -6- cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobenciamino-5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-diclorobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de 3-nitrobencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -5-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, - - la 2- (piridin-3-il) -4- (3-nitrobencilamino) -5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -5, 6- ciclohepteno-tieno- [2,'3-d] -pirimidina, con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -6-etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -6-cloro- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -5-cloro- 6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-3-il) -4- (3-nitrobencilamino) -6-nitro- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3-nitrobencilamino) -6- trifluorometil-tieno- ['2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -6- metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -5- metil-tíeno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) - 5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, - - la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -6-etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -6- clorotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -5- cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- ( isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -6- nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, - - la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3-nitrobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -6-metil- tieno- [2, 3-d] -pirimidiha; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -5-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -5, 6^ ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, - - la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -6-etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -6-cloro- tieno- [2, 3-d] -pirimidiha; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -5-cloro- 6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -6-nitro- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3-nitrobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il ) -4- (3-nitrobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -5-metil- tieno- [2, 3-d] -pirimidrna; con 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -5, 6, 7, 8- tetrahidro- [ 1 ] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-2-il) -4- (3-nitrobencilamino) -6-etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -6-cloro- tieno- [2, 3-d] -p,irimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -5-cloro- 6-metil-tieno- [2, 3-d] -"pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -6-nitro- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3-nitrobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-4-il) -4- (3-nitrobencilamino) -6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2 , 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -5-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -5, 6- ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -5, 6- ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -6-etil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-4-il) -4- (3-nitrobencilamino) -6-cloro- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -5-cloro- 6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -6-nitro- tieno- [2, 3-d] -pirimidÍTia; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -5, 6- dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3-nitrobencilamino) -6- trifluorometil-tieno- [2, 3-d] -pirimidína. De manera análoga se obtiene, por reacción de 3,4-metilendioxifenetilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -6-metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2 , 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidinal la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-metilendioxifenetil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -6-metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5,'6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- a ino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -6 etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, - - la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3,'4-metilendioxifenetil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con- 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-metilendioxifenetil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- a ino) -6-metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6, 7, 8-etrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d]-pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, - 14 - la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, -metilendioxifenetil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil-5, 6- di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -trifluorommetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-metilendioxifenetil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] - ~ pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- amino) -6-metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- a ino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil-a ino) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, -metilendioxifenetil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4'-metilendioxifenetil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-metilendioxifenetil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] - ~ pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -6-metil-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1]-benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, - 1 - la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4"-metilendioxifenetil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con '4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-metilendioxifenetil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina. De manera análoga se obtiene, por reacción de 3,4-etilendioxibencilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 5,6,7, 8-tetrahidro- [l]'-benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, - - la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 6-cloro-tieno- [2, 3-dJ -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d]-pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4- (3, 4-etilendioxibencilamino) - 6-trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, - - la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3,'4-etilendioxibencil- amino) -5, 6-ciclopenteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- a ino) -5, 6-ciclohepteno-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -6-cloro-tieno- [2, 3-d] -pirimidina;
- -con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -5-cloro-6-metil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5,'6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno-[2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4- (3, 4-etilendioxibencil- amino) -6-trifluorometil-tieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-etilendioxibencilamino) - 6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, - - la 2- (pirazin-2-il) -4- (3, -etilendioxibencilamino) - 5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1]-benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, -etilendioxibencilamino) - 6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-etilendioxibencilamino) - 6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [ 2, 3-d] -pirimidina, - - la 2- (pirazin-2-il) -4- (3, 4-etilendioxibencilamino) - 5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, -etilendioxibencilamino) - 6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-di-metil-tieno- [2,'3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4- (3, -etilendioxibencilamino) - 6-trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, - - la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirídin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4- (3, 4-etilendioxibencilamino) - 6-trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, -etilendioxibencilamino) - 6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-etilendioxibencilamino) - 5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-etilendioxibencil- amino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3- d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, -etilendioxibencilamino) - 5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-etilendioxibencilamino) - 6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-etilendioxibencilamino) - 6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, -etilendioxibencilamino) - 5-cloro-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, -etilendioxibencilamiho) - 6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] - pirimidina, la 2- (piridin-4-il) -4- (3, 4-etilendioxibencilamino) - 5, 6-di-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4- (3, 4-etilendioxibencilamino) - 6-trifluorometil-tieno- [2, 3-d] -pirimidina. De manera análoga se obtiene, por reacción de fenetilamina con 4-cloro-2- (piridin-3-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-metil-tieno- [2, 3-d] -pirímidina, la 2- (piridin-3-il) -4-fenetilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-5, 6, 7, 8- tetrahidro- [1 ] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-ciclopenteno-tieno- [2 , 3-d] -pirímidina, la 2- (piridin-3-il) -4-fenetilamino-5, 6- ciclopentenotieno- [2 , 3-d] -pirimidina;
con 4-cloro-2- (piridin-3-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-5, 6- cicloheptenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-3-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-3-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-3-il) -4-fenetilamino-6-trifluoro- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-5, 6- ciclopentenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-5, 6- cicloheptenotieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (isoxazol-5-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-5-cloro-6- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (isoxazol-5-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (isoxazol-5-il) -4-fenetilamino-6-trifluoro- metil-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (pirazin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-tenetilamino-5, 6- ciclopentenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-5, 6- cicloheptenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-etil-tieno- [2, 3-d]-pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-6-etil-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (pirazin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (pirazin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (pirazin-2-il) -4-fenetilamino-6-trifluoro- metiltieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-6-metil-tieno- [2, 3-d] -pirimidina;
- 16 -con 4-cloro-2- (piridin-2-il) -5-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-5-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6, 1 , 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-5, 6- ciclopentenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-5, 6- cicloheptenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-6-cloro-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-2-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -5, 6-dimetil-tieno- [2 , 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-2-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-2-il) -4-fenetilamino-6-trifluorometil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-metil-tieno- [2, 3-d]-pirimidina, la 2- (piridin-4-il) -4-fenetilamino-6-metil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-metil-tieno- [2, 3-d]-pirimidina, la 2- (piridin-4-il) -4-fenetilamino-5-metil-tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-4-il) -5, 6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-5, 6, 7, 8- tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclopenteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-5, 6- ciclopentenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-ciclohepteno-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-5, 6- cicloheptenotieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-etil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-6-etil-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-cloro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-6-cloro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5-cloro-6-metil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-5-cloro-6-metil- tieno- [2, 3-d] -pirimidina;
con 4-cloro-2- (piridin-4-il) -6-nitro-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-6-nitro-tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -5, 6-dimetil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-5, 6-dimetil- tieno- [2, 3-d] -pirimidina; con 4-cloro-2- (piridin-4-il) -6-trifluorometil-tieno- [2, 3-d] -pirimidina, la 2- (piridin-4-il) -4-fenetilamino-6-trifluoro- metil-tieno- [2, 3-d] -pirimidina.
Ejemplo 5 Se hidrogena una solución de 2- (imidazol-1-il) -6-metil-4- (3-nitrobencilamino) -tieno- [2, 3-d] -pirimidina en metanol en presencia de niquel-Raney. Se separa el catalizador por filtración y se concentra la solución. Después de recristalizar se obtiene la 2- (imidazol-1-il) -6-metil-4- (3-aminobecilamino) -tieno- [2, 3-d] -pirimidina.
Ejemplo 6 Se agrega 1 ml de acetaldehído recién destilado a una solución de 6 g de 2- (imidazol-1-il) -6-metil-4- (3-aminobencilamino) -tieno- [2, 3-d] -pirimidina y 0.5 g de tetracloruro de titanio en 100 ml de metanol. Luego se agregan 4 g de cianoborohidruro de sodio y se agita durante 30 minutos. Se agrega ácido clorhídrico semiconcentrado, se trabaja la mezcla de manera usual y se obtiene la 2- (imidazol-1-il) -6-metil-4- (3-N-etilamino-bencilamino) -tieno- [2, 3-d] -pirimidina .
Ejemplo 7 Los compuestos que se indican a continuación se obtienen de manera análoga 'a la descripta en el ejemplo 2: 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4- (3, 4-difluorobencil-amino) - [1] -benzotieno- [2, 3-d] -pirimidina, p.f. 212°; 2- (imidazol-1-il) -5, 6-ciclopenteno-4-bencilamino-tieno- [2, 3-d] -pirimidina, p.f. 221°; 2- (imidazol-1-il) -6-metil-4-bencilamino-tieno- [2, 3-d] -pirimidina, p.f. 241°; 2- (imidazol-1-il) -6-metil-4- (3, -dimetoxibencil-amino) -tieno- [2, 3-d] -pirimidina, p.f. 217°; 2- (imidazol-1-il) -6-cloro-5-metil-4- (3, 4-metilen-dioxibencilamino) -tieno- [2, 3-d] -pirimidina, p.f. 250°; 2- (imidazol-1-il) -5, 6, 7, 8-tetrahidro-4-bencilamino-[1] -benzotieno- [2, 3-d] -pirimidina, p.f. 190°;
2- (1, 2, 4-triazol-l-il) -6-metil-4- (3, -metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina, p.f. 231°; 2- (imidazol-1-il) -6-isopropil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina, p.f. 192°; 2- (imidazol-1-il) -6-propil-4- (3, 4-metilendioxi-bencilamino) -tieno- [2, 3-d] -pirimidina, p.f. 183°. Los ejemplos que siguen se refieren a las preparaciones farmacéuticas:
Ejemplo A: Frascos para inyecciones El pH de una solución de 100 g de una sustancia activa de la fórmula I y 5 g de fosfato ácido disódico en 3 1 de agua bidestilada se ajusta a 6.5 con ácido clorhídrico 2N, luego se filtra en condiciones estériles, se llenan los frascos con la solución, se liofiliza y se cierran los frascos en condiciones estériles. Cada frasco para inyección contiene 5 mg de la sustancia activa.
Ejemplo B: Supositorios Se funde una mezcla compuesta por 20 g de una sustancia activa de la fórmula I, 100 g de lecitina de soja y 1400 g de manteca de cacao, luego se vierte la masa fundida dentro de los moldes y se deja enfriar. Cada supositorio contiene 20 mg de sustancia activa.
Ejemplo C: Solución Se prepara una solución con 1 g de una sustancia activa de la fórmula I, 9.38 g de NaH2P04 x 2H20, 28.48 g de Na2HP0 x 12 H2O, 0.1 g de cloruro de benzalconio y 940 ml de agua bidestilada. Se ajusta el pH a 6.8, se lleva a volumen de 1 1 y se esteriliza por irradiación.
Esta solución puede ser empleada en forma de gotas para los ojos.
Ejemplo D: Ungüento En condiciones asépticas se mezclan 500 mg de una sustancia activa de la fórmula I con 99.5 g de vaselina.
Ejemplo E: Tabletas Una mezcla compuesta por 1 kg de una sustancia activa de la fórmula I, 4 kg de lactosa, 1.2 kg de almidón de papa, 0.2 kg de talco y 0.1 kg de estearato de magnesio se comprime en forma de tabletas, de manera tal que cada tableta contenga 10 mg de la sustancia activa.
Ejemplo F: Grageas Se forman las tabletas de manera análoga a la descripta en el ejemplo E y luego se recubren de manera usual con un baño de sacarosa, almidón de papa, talco, tragacanto y colorante.
Ejemplo G: Cápsulas Con 2 kg de una sustancia activa de la fórmula I se llenan cápsulas de gelatina dura, de manera tal que cada cápsula contenga 20 mg de la sustancia activa.
Ejemplo H: Ampollas Una solución de 1 kg de una sustancia activa de la fórmula I en 60 1 de agua bidestilada se filtra en condiciones estériles. Se llenan las ampollas con esta solución y luego se liofilizan y se cierran en condiciones estériles. Cada ampolla contiene 10 mg de la sustancia activa.
Ejemplo I: Solución inhalante en aerosol Se disuelven 14 g de una sustancia activa de la fórmula I en 10 1 de solución isotónica de NaCl. Con esta solución se llenan recipientes comerciales que poseen un mecanismo vaporizador. La solución puede ser inhalada por la boca o la nariz. Cada rociada (aprox. 0.1 ml) corresponde a una dosis de aprox. 0.14 mg.
Se hace constar que con relación a esta fecha, el mejor método conocido por la solicitante para llevar a la práctica la citada invención, es el que resulta claro de - -la presente descripción de la invención. Habiéndose descrito la invención como antecede, se reclama como propiedad lo contenido en las siguientes:
Claims (9)
1.- Los compuestos de la fórmula I en donde R1, R2 representan independientemente H, A, OA, alquenilo, alquinilo, NO2, CF3 o Hal, siendo uno de los restos R1 Ó R2 siempre ? H, R1 y R2, juntos, también representan alquileno de 3 a 5 átomos de C, R3, R4 representan independientemente H, A, OA, Hal, N02, NH2, NHA o NAA*, R3 y R4, juntos, también representan -0-CH2-CH2-, -0-CH2- 0- ó -O-CH2-CH2-O-, A, A' representan independientemente alquilo de 1 a 6 átomos de C, X representa un heterociclo insaturado de 5 a 7 miembros, que puede estar no sustituido o mono, di o trisustituido con A, Hal o CF3, que contiene de 1 a 4 átomos de N, 0 y/o S y en el que otros grupos de CH2 también pueden estar reemplazados por NH, NA, S u 0, y que se encuentra unido a través del N o C, Hal representa F, Cl, Br o I y n es 0, 1, 2 ó 3, y a sus sales aceptables desde el punto de vista fisiológico.
2.- Los compuestos de la fórmula I, según la reivindicación 1, (a) 2- (1-imidazolil) -6-metil-4- (3, 4-metilendioxi- bencilamino) -tieno- [2, 3-d] -pirimidina; (b) 2- (1-imidazolil) -5, 6-dimetil-4- (3, 4-metilendioxi- bencilamino) -tieno- [2, 3-d] -pirimidina; (c) 2- (1-imidazolil) -4- (3, 4-metilendioxi-bencilamino) - 5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; (d) 2- (1-imidazolil) -5-cloro-4- (3, 4-metilendioxi- bencilamino) -tieno- [2, 3-d] -pirimidina; (e) 2- (1-imidazolil) -6-cloro-4- (3, 4-metilendioxi- bencilamino) -tieno- [2, 3-d] -pirimidina; (f) 2- (l,2,4-triazol-l-il)-4-(3,4-metilendioxi- bencilamino) -5, 6, 7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] -pirimidina; (g) 2- (pirazol-1-il) -4- (3, 4-metilendioxi-bencilamino) - 5,6,7, 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina; (h) 2- (piridin-3-il) -4- (3, 4-metilendioxi-bencilamino) - 5, 6, 1 , 8-tetrahidro- [1] -benzotieno- [2, 3-d] - pirimidina.
3.- Procedimiento para preparar a) compuestos de la fórmula I,' según la reivindicación 1, y sus sales, en donde X se encuentra unido a través del N, caracterizado porque se hace reaccionar un compuesto de la fórmula II en donde R , R , R , R y n tienen los significados indicados, y L representa Cl, Br, OH, SCH3 o un grupo OH esterificado y reactivo, con un heterociclo insaturado de 5 a 7 miembros que puede estar no sustituido o mono, di o trisustituido con A, Hal o CF3, que tiene al menos un grupo de NH y en el que otros grupos de CH2 también pueden estar reemplazados por NH, NA, S ó 0, o b) compuestos de la fórmula I, según la reivindicación 1, y sus sales, en donde X se encuentra unido a través del C, caracterizado porque se hace reaccionar un compuesto de la fórmula III, en donde R1, R2 y X tienen los significados indicados y L representa Cl, Br, OH, SCH3 un grupo OH esterificado y reactivo, con un compuesto de la fórmula IV en donde R3, R4 y n tienen los significados indicados, o c) porque en un compuesto de la fórmula I se transforma un resto R1, R2, R3 y/o R4 en otro resto R1, R2, R3 y/o R4, ya sea reduciendo un grupo nitro, acilando un grupo de amino primario o secundario o transformándolo por aminación reductiva en una amina alquilada, y/o porque se transforma un compuesto básico de la fórmula I en una de sus sales por tratamiento con un ácido.
4.- Procedimiento para obtener preparaciones farmacéuticas, caracterizado porque se lleva un compuesto de la fórmula I, según la reivindicación 1, y/o una de sus sales aceptables desde el punto de vista fisiológico a una forma de dosificación adecuada, junto con al menos un excipiente o producto auxiliar sólido, líquido o semilíquido .
5.- Preparación farmacéutica, caracterizada porgue contiene al menos un compuesto de la fórmula I, según la reivindicación 1, y/o una de sus sales aceptables desde el punto de vista fisiológico.
6.- Los compuestos de la fórmula I, según la reivindicación 1, y sus sales aceptables desde el punto de vista fisiológico para combatir las enfermedades del sistema cardiocirculatorio y para la terapia de los trastornos de la potencia.
7.- Medicamento de la fórmula I, según la reivindicación 1, y sus sales aceptables desde el punto de vista fisiológico como inhibidores de la fosfodiesterasa V.
8.- Empleo de los compuestos de la fórmula I, según la reivindicación 1, y/o de sus sales aceptables desde el punto de vista fisiológico para preparar un medicamento.
9.- Empleo de los compuestos de la fórmula I, según la reivindicación 1, y/o de sus sales aceptables desde el punto de vista fisiológico para combatir enfermedades.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE19632423.8 | 1996-08-12 |
Publications (1)
Publication Number | Publication Date |
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MXPA99001387A true MXPA99001387A (es) | 1999-09-20 |
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