DE69912618T2 - NEUE THIENO[2,3-d]PYRIMIDINDIONE, VERFAHREN FÜR IHRE HERSTELLUNG UND IHRE VERWENDUNG IN DER THERAPIE - Google Patents
NEUE THIENO[2,3-d]PYRIMIDINDIONE, VERFAHREN FÜR IHRE HERSTELLUNG UND IHRE VERWENDUNG IN DER THERAPIE Download PDFInfo
- Publication number
- DE69912618T2 DE69912618T2 DE69912618T DE69912618T DE69912618T2 DE 69912618 T2 DE69912618 T2 DE 69912618T2 DE 69912618 T DE69912618 T DE 69912618T DE 69912618 T DE69912618 T DE 69912618T DE 69912618 T2 DE69912618 T2 DE 69912618T2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- pyrimidine
- methylpropyl
- dione
- thieno
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000002560 therapeutic procedure Methods 0.000 title claims description 6
- JGOOQALRLGHKIY-UHFFFAOYSA-N 1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC2=C1C=CS2 JGOOQALRLGHKIY-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 243
- 230000002441 reversible effect Effects 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 98
- -1 1 to 3 Chemical group 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 24
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 230000001506 immunosuppresive effect Effects 0.000 claims description 6
- 230000000414 obstructive effect Effects 0.000 claims description 6
- 210000002345 respiratory system Anatomy 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- WBAKOAPFWILXJX-UHFFFAOYSA-N 3-methyl-6-(1-methylbenzimidazole-2-carbonyl)-1-(2-methylpropyl)-5-propan-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(C(=O)C=3SC=4N(C(N(C)C(=O)C=4C=3SC(C)C)=O)CC(C)C)=NC2=C1 WBAKOAPFWILXJX-UHFFFAOYSA-N 0.000 claims description 5
- KJDSEKFFXGDYOD-UHFFFAOYSA-N 5-(3-hydroxypropylsulfanyl)-3-methyl-1-(2-methylpropyl)-6-(pyridine-3-carbonyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound OCCCSC=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C(=O)C1=CC=CN=C1 KJDSEKFFXGDYOD-UHFFFAOYSA-N 0.000 claims description 5
- HIGFITSDKNNWTJ-UHFFFAOYSA-N 6-[hydroxy-(1-methylbenzimidazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(C(O)C=3SC=4N(C(N(C)C(=O)C=4C=3)=O)CC(C)C)=NC2=C1 HIGFITSDKNNWTJ-UHFFFAOYSA-N 0.000 claims description 5
- JCNVVNANFIZEMZ-UHFFFAOYSA-N 6-[hydroxy-(1-methylbenzimidazol-2-yl)methyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(C(O)C=3SC=4N(C(N(C)C(=O)C=4C=3)=O)C(C)C)=NC2=C1 JCNVVNANFIZEMZ-UHFFFAOYSA-N 0.000 claims description 5
- 206010062016 Immunosuppression Diseases 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- LLAAJKFSLZKYHE-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-[hydroxy-(1-methylbenzimidazol-2-yl)methyl]-3-methylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound N=1C2=CC=CC=C2N(C)C=1C(O)C(S1)=CC(C(N(C)C2=O)=O)=C1N2CC1CC1 LLAAJKFSLZKYHE-UHFFFAOYSA-N 0.000 claims description 4
- CRWMCZHHOIGMNV-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(pyridine-3-carbonyl)-5-thiophen-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=CSC=1SC=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C(=O)C1=CC=CN=C1 CRWMCZHHOIGMNV-UHFFFAOYSA-N 0.000 claims description 4
- DSQHABJZILXDLV-UHFFFAOYSA-N 3-methyl-6-[(1-methylbenzimidazol-2-yl)methyl]-1-(2-methylpropyl)-5-propan-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(CC=3SC=4N(C(N(C)C(=O)C=4C=3SC(C)C)=O)CC(C)C)=NC2=C1 DSQHABJZILXDLV-UHFFFAOYSA-N 0.000 claims description 4
- AMUJWWSZSRTUKN-UHFFFAOYSA-N 5-(3-hydroxypropoxy)-3-methyl-1-(2-methylpropyl)-6-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound OCCCOC=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=CC=CN=C1 AMUJWWSZSRTUKN-UHFFFAOYSA-N 0.000 claims description 4
- MQCHNBJYTPUQRP-UHFFFAOYSA-N 6-(benzimidazol-1-ylmethyl)-3-methyl-1-(2-methylpropyl)-5-thiophen-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C3=CC=CC=C3N=C2)=C1SC1=CC=CS1 MQCHNBJYTPUQRP-UHFFFAOYSA-N 0.000 claims description 4
- ARZUNQNWVZXAOQ-UHFFFAOYSA-N 6-(benzimidazol-1-ylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=NC2=CC=CC=C2N1CC(S1)=CC2=C1N(CC(C)C)C(=O)N(C)C2=O ARZUNQNWVZXAOQ-UHFFFAOYSA-N 0.000 claims description 4
- LKJZWOJOQXWWMP-UHFFFAOYSA-N 6-(benzimidazol-1-ylmethyl)-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=NC2=CC=CC=C2N1CC(S1)=CC2=C1N(C(C)C)C(=O)N(C)C2=O LKJZWOJOQXWWMP-UHFFFAOYSA-N 0.000 claims description 4
- UWRHFEKBXAEQTL-UHFFFAOYSA-N 6-[1h-benzimidazol-2-yl(hydroxy)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2NC(C(O)C=3SC=4N(C(N(C)C(=O)C=4C=3)=O)CC(C)C)=NC2=C1 UWRHFEKBXAEQTL-UHFFFAOYSA-N 0.000 claims description 4
- UMDLABDUJBFKRM-UHFFFAOYSA-N 6-[hydroxy-(1-methylbenzimidazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)-5-propan-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(C(O)C=3SC=4N(C(N(C)C(=O)C=4C=3SC(C)C)=O)CC(C)C)=NC2=C1 UMDLABDUJBFKRM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- NKAMAKVCUVIVTK-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-methyl-6-[(1-methylbenzimidazol-2-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound N=1C2=CC=CC=C2N(C)C=1CC(S1)=CC(C(N(C)C2=O)=O)=C1N2CC1CC1 NKAMAKVCUVIVTK-UHFFFAOYSA-N 0.000 claims description 3
- DGXSDNVECZHQAZ-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(pyridin-3-ylmethyl)-5-thiophen-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=CSC=1SC=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=CC=CN=C1 DGXSDNVECZHQAZ-UHFFFAOYSA-N 0.000 claims description 3
- LITLXRLYLVSWBD-UHFFFAOYSA-N 3-methyl-6-[(1-methylbenzimidazol-2-yl)methyl]-1-(2-methylpropyl)-5-propan-2-ylsulfonylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(CC=3SC=4N(C(N(C)C(=O)C=4C=3S(=O)(=O)C(C)C)=O)CC(C)C)=NC2=C1 LITLXRLYLVSWBD-UHFFFAOYSA-N 0.000 claims description 3
- BHJLMTLHXPSAQR-UHFFFAOYSA-N 3-methyl-6-[(1-methylbenzimidazol-2-yl)methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(CC=3SC=4N(C(N(C)C(=O)C=4C=3)=O)CC(C)C)=NC2=C1 BHJLMTLHXPSAQR-UHFFFAOYSA-N 0.000 claims description 3
- BBYYQONNCAAMKA-UHFFFAOYSA-N 3-methyl-6-[(1-methylbenzimidazol-2-yl)methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2N(C)C(CC=3SC=4N(C(N(C)C(=O)C=4C=3)=O)C(C)C)=NC2=C1 BBYYQONNCAAMKA-UHFFFAOYSA-N 0.000 claims description 3
- NSJKRGJIUCTXFM-UHFFFAOYSA-N 5-(3-hydroxypropylsulfanyl)-3-methyl-1-(2-methylpropyl)-6-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound OCCCSC=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=CC=CN=C1 NSJKRGJIUCTXFM-UHFFFAOYSA-N 0.000 claims description 3
- SCWAQHDJVTWJEC-UHFFFAOYSA-N 5-(azetidine-1-carbonyl)-1-(cyclopropylmethyl)-3-methyl-6-[(1-methylbenzimidazol-2-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound N=1C2=CC=CC=C2N(C)C=1CC(=C(C=1C(=O)N(C)C2=O)C(=O)N3CCC3)SC=1N2CC1CC1 SCWAQHDJVTWJEC-UHFFFAOYSA-N 0.000 claims description 3
- NWMHICYOEMTIFL-OAHLLOKOSA-N 5-[(3r)-3-hydroxypyrrolidin-1-yl]sulfonyl-3-methyl-1-(2-methylpropyl)-6-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@H](O)CC1)N1S(=O)(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=CC=CN=C1 NWMHICYOEMTIFL-OAHLLOKOSA-N 0.000 claims description 3
- FYODULSKIARMEB-UHFFFAOYSA-N 6-[1,3-benzothiazol-2-yl(hydroxy)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2SC(C(O)C=3SC=4N(C(N(C)C(=O)C=4C=3)=O)CC(C)C)=NC2=C1 FYODULSKIARMEB-UHFFFAOYSA-N 0.000 claims description 3
- LQTUQKQSHVWMDW-UHFFFAOYSA-N 6-[hydroxy(pyridin-3-yl)methyl]-3-methyl-1-(2-methylpropyl)-5-propan-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC(C)SC=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C(O)C1=CC=CN=C1 LQTUQKQSHVWMDW-UHFFFAOYSA-N 0.000 claims description 3
- ZJKGXLPYZUBLOI-UHFFFAOYSA-N C=1C=2C(=O)NC(=O)N(CC(C)C)C=2SC=1C(=O)C1=CC=CN=C1 Chemical compound C=1C=2C(=O)NC(=O)N(CC(C)C)C=2SC=1C(=O)C1=CC=CN=C1 ZJKGXLPYZUBLOI-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- UQVFEKVXIUKTIA-UHFFFAOYSA-N 6-(benzimidazol-1-ylmethyl)-1-(cyclopropylmethyl)-3-methylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2SC(CN3C4=CC=CC=C4N=C3)=CC=2C(=O)N(C)C(=O)N1CC1CC1 UQVFEKVXIUKTIA-UHFFFAOYSA-N 0.000 claims description 2
- QYOXPODCRHMTOK-UHFFFAOYSA-N 6-[(1,3-dioxoisoindol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)-5-thiophen-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C(C3=CC=CC=C3C2=O)=O)=C1SC1=CC=CS1 QYOXPODCRHMTOK-UHFFFAOYSA-N 0.000 claims description 2
- CARZRMQRFMKZSE-UHFFFAOYSA-N 6-[(1,4-dioxo-3h-phthalazin-2-yl)methyl]-3-methyl-1-(2-methylpropyl)-5-propan-2-ylsulfanylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound N1C(=O)C2=CC=CC=C2C(=O)N1CC(S1)=C(SC(C)C)C2=C1N(CC(C)C)C(=O)N(C)C2=O CARZRMQRFMKZSE-UHFFFAOYSA-N 0.000 claims description 2
- VCBYSTZNJAZSMW-UHFFFAOYSA-N 6-[hydroxy(pyridin-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C(O)C1=CC=CC=N1 VCBYSTZNJAZSMW-UHFFFAOYSA-N 0.000 claims description 2
- BCZHYOXHQNCJEP-UHFFFAOYSA-N 6-[hydroxy(pyridin-3-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C(O)C1=CC=CN=C1 BCZHYOXHQNCJEP-UHFFFAOYSA-N 0.000 claims description 2
- IMGVYVFMNBEGTO-UHFFFAOYSA-N 6-[hydroxy(pyridin-4-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C(O)C1=CC=NC=C1 IMGVYVFMNBEGTO-UHFFFAOYSA-N 0.000 claims description 2
- NTPNEWWRXUIHCB-UHFFFAOYSA-N 6-[hydroxy(thiophen-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C(O)C1=CC=CS1 NTPNEWWRXUIHCB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- GJQRXSNYCXFEJD-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(1,3-thiazol-2-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=NC=CS1 GJQRXSNYCXFEJD-UHFFFAOYSA-N 0.000 claims 1
- XQRUPBHBUFCSNE-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2C(CC=3SC=4N(C(N(C)C(=O)C=4C=3)=O)CC(C)C)=CNC2=N1 XQRUPBHBUFCSNE-UHFFFAOYSA-N 0.000 claims 1
- XQGBWCSNZSTOGH-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=CC=CC=N1 XQGBWCSNZSTOGH-UHFFFAOYSA-N 0.000 claims 1
- IMLLAPNOOLJMMH-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=CC=CN=C1 IMLLAPNOOLJMMH-UHFFFAOYSA-N 0.000 claims 1
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Landscapes
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9802895 | 1998-08-28 | ||
| SE9802895 | 1998-08-28 | ||
| PCT/SE1999/001400 WO2000012514A1 (en) | 1998-08-28 | 1999-08-18 | Novel compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69912618D1 DE69912618D1 (de) | 2003-12-11 |
| DE69912618T2 true DE69912618T2 (de) | 2004-10-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69912618T Expired - Fee Related DE69912618T2 (de) | 1998-08-28 | 1999-08-18 | NEUE THIENO[2,3-d]PYRIMIDINDIONE, VERFAHREN FÜR IHRE HERSTELLUNG UND IHRE VERWENDUNG IN DER THERAPIE |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6300334B1 (enExample) |
| EP (1) | EP1107973B1 (enExample) |
| JP (1) | JP2002523511A (enExample) |
| AT (1) | ATE253580T1 (enExample) |
| AU (1) | AU763758B2 (enExample) |
| CA (1) | CA2339664A1 (enExample) |
| DE (1) | DE69912618T2 (enExample) |
| DK (1) | DK1107973T3 (enExample) |
| ES (1) | ES2211161T3 (enExample) |
| NZ (1) | NZ509809A (enExample) |
| PT (1) | PT1107973E (enExample) |
| WO (1) | WO2000012514A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9801399D0 (sv) | 1998-04-21 | 1998-04-21 | Astra Pharma Prod | Method and apparatus for filling containers |
| ATE272642T1 (de) * | 2000-05-04 | 2004-08-15 | Astrazeneca Ab | Thieno(2,3-d)pyrimidindione und ihre verwendung als pharmazeutische mittel |
| GB2361917A (en) * | 2000-05-04 | 2001-11-07 | Astrazeneca Ab | Novel thieno[2,3-d]pyrimidinediones |
| GB2363377B (en) * | 2000-06-14 | 2004-06-09 | Astrazeneca Ab | Novel thieno[2,3-d]pyrimidinediones and therapeutic uses thereof |
| BR0207216A (pt) * | 2001-02-14 | 2004-03-09 | Warner Lambert Co | Derivados de tieno 2,3-d-pirimidindiona como inibidores de metaloproteinase matriz |
| GB0117583D0 (en) * | 2001-07-19 | 2001-09-12 | Astrazeneca Ab | Novel compounds |
| GB0118479D0 (en) * | 2001-07-28 | 2001-09-19 | Astrazeneca Ab | Novel compounds |
| SE0300119D0 (sv) * | 2003-01-17 | 2003-01-17 | Astrazeneca Ab | Novel compounds |
| SE0300120D0 (sv) * | 2003-01-17 | 2003-01-17 | Astrazeneca Ab | Novel compounds |
| WO2004065395A1 (en) * | 2003-01-17 | 2004-08-05 | Astrazeneca Ab | Thienopyridazinones and their use in modulation of autoimmune disease |
| CN1925855B (zh) | 2003-12-19 | 2010-06-16 | 普莱希科公司 | 开发Ret调节剂的化合物和方法 |
| US7498342B2 (en) | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| EP1768662A2 (en) | 2004-06-24 | 2007-04-04 | Novartis Vaccines and Diagnostics, Inc. | Small molecule immunopotentiators and assays for their detection |
| EP1989210A2 (en) * | 2006-03-02 | 2008-11-12 | Cv Therapeutics, Inc. | A2a adenosine receptor antagonists |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| EP2170830B1 (en) | 2007-07-17 | 2014-10-15 | Plexxikon, Inc. | 2-FLUORO-BENZENESULFONAMIDE COMPOUNDS AS Raf KINASE MODULATORS |
| AU2010227225A1 (en) * | 2009-03-23 | 2011-09-15 | Glenmark Pharmaceuticals, S.A. | Furopyrimidinedione derivatives as TRPA1 modulators |
| KR20170058465A (ko) | 2009-04-03 | 2017-05-26 | 에프. 호프만-라 로슈 아게 | 프로판-１-술폰산 ｛３-［５-（４-클로로-페닐）-１Ｈ-피롤로［２，３-ｂ］피리딘-３-카르보닐］-２，４-디플루오로-페닐｝-아미드 조성물 및 그의 용도 |
| AU2010315126B2 (en) | 2009-11-06 | 2015-06-25 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2012109075A1 (en) | 2011-02-07 | 2012-08-16 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| MX2016004250A (es) * | 2013-10-07 | 2016-07-12 | Bayer Pharma AG | Tienouracilcarboxamidas ciclicas y usos de las mismas. |
| UY36586A (es) | 2015-03-26 | 2016-10-31 | Bayer Pharma AG | Heterociclilmetiltienouracilos y uso de los mismos |
| WO2018041771A1 (de) | 2016-09-02 | 2018-03-08 | Bayer Pharma Aktiengesellschaft | (1-methylcyclopropyl)methyl-substituierte thienouracile und ihre verwendung |
| RU2019111357A (ru) | 2016-09-23 | 2020-10-23 | Байер Акциенгезельшафт | N3-циклически замещенные тиеноурацилы и их применение |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01213284A (ja) * | 1988-02-22 | 1989-08-28 | Sankyo Co Ltd | チエノピリミジン−２，４−ジオン誘導体 |
| DD293824A5 (de) | 1990-04-24 | 1991-09-12 | Karl-Marx-Universitaet Leipzig,De | Verfahren zur herstellung von 3-(mercaptoalkyl)=thieno/2,3-d/pyrimidin-2,4(1h,3h)-dionen |
| TW276256B (enExample) * | 1993-08-26 | 1996-05-21 | Takeda Pharm Industry Co Ltd |
-
1999
- 1999-08-18 WO PCT/SE1999/001400 patent/WO2000012514A1/en not_active Ceased
- 1999-08-18 CA CA002339664A patent/CA2339664A1/en not_active Abandoned
- 1999-08-18 PT PT99944964T patent/PT1107973E/pt unknown
- 1999-08-18 EP EP99944964A patent/EP1107973B1/en not_active Expired - Lifetime
- 1999-08-18 AT AT99944964T patent/ATE253580T1/de not_active IP Right Cessation
- 1999-08-18 DE DE69912618T patent/DE69912618T2/de not_active Expired - Fee Related
- 1999-08-18 NZ NZ509809A patent/NZ509809A/xx unknown
- 1999-08-18 JP JP2000567536A patent/JP2002523511A/ja active Pending
- 1999-08-18 DK DK99944964T patent/DK1107973T3/da active
- 1999-08-18 ES ES99944964T patent/ES2211161T3/es not_active Expired - Lifetime
- 1999-08-18 AU AU57677/99A patent/AU763758B2/en not_active Ceased
- 1999-08-18 US US09/402,837 patent/US6300334B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1107973B1 (en) | 2003-11-05 |
| ATE253580T1 (de) | 2003-11-15 |
| CA2339664A1 (en) | 2000-03-09 |
| AU763758B2 (en) | 2003-07-31 |
| AU5767799A (en) | 2000-03-21 |
| DE69912618D1 (de) | 2003-12-11 |
| JP2002523511A (ja) | 2002-07-30 |
| ES2211161T3 (es) | 2004-07-01 |
| PT1107973E (pt) | 2004-03-31 |
| WO2000012514A1 (en) | 2000-03-09 |
| US6300334B1 (en) | 2001-10-09 |
| DK1107973T3 (da) | 2004-02-23 |
| EP1107973A1 (en) | 2001-06-20 |
| NZ509809A (en) | 2002-11-26 |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |