HRP20120822T1 - Supstituirani 4,5,6,7-tetrahidrotienopiridini kao kcnq2/3 modulatori za lijeäśenje boli, epilepsije i urinarne inkontinencije - Google Patents
Supstituirani 4,5,6,7-tetrahidrotienopiridini kao kcnq2/3 modulatori za lijeäśenje boli, epilepsije i urinarne inkontinencije Download PDFInfo
- Publication number
- HRP20120822T1 HRP20120822T1 HRP20120822AT HRP20120822T HRP20120822T1 HR P20120822 T1 HRP20120822 T1 HR P20120822T1 HR P20120822A T HRP20120822A T HR P20120822AT HR P20120822 T HRP20120822 T HR P20120822T HR P20120822 T1 HRP20120822 T1 HR P20120822T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyridin
- dihydrothieno
- phenyl
- oxo
- butanamide
- Prior art date
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- 208000002193 Pain Diseases 0.000 title claims 2
- 206010046543 Urinary incontinence Diseases 0.000 title claims 2
- 206010015037 epilepsy Diseases 0.000 title claims 2
- MSDZLUHQKBFCHC-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-b]pyridine Chemical class C1CCNC2=C1SC=C2 MSDZLUHQKBFCHC-UHFFFAOYSA-N 0.000 title 1
- 229920006395 saturated elastomer Polymers 0.000 claims 55
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 33
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000001072 heteroaryl group Chemical group 0.000 claims 30
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 15
- NOSOEJSZWOKISI-UHFFFAOYSA-N butane-1,4-dione Chemical compound O=[C]CC[C]=O NOSOEJSZWOKISI-UHFFFAOYSA-N 0.000 claims 15
- WJFYLCXWEXZNHU-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-b]pyridine Chemical class N1C=CC=C2SCCC21 WJFYLCXWEXZNHU-UHFFFAOYSA-N 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 7
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- QLAHJLWHUVUOFL-UHFFFAOYSA-N 4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 QLAHJLWHUVUOFL-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- ZCHDKNZOBWOKIQ-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=C(F)C(F)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 ZCHDKNZOBWOKIQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- JSVDJGTYCYGXSH-MFNHVEPQSA-N (1s)-2-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carbonyl)-n-[[3-(trifluoromethyl)phenyl]methyl]cyclohexane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)[C@@H]2C(CCCC2)C(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 JSVDJGTYCYGXSH-MFNHVEPQSA-N 0.000 claims 1
- JSVDJGTYCYGXSH-MXKXXCEUSA-N (1s,2r)-2-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carbonyl)-n-[[3-(trifluoromethyl)phenyl]methyl]cyclohexane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)[C@@H]2[C@@H](CCCC2)C(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 JSVDJGTYCYGXSH-MXKXXCEUSA-N 0.000 claims 1
- RDLVEGRXNJIRKK-FQTTXOOSSA-N (1s,2r)-2-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carbonyl)-n-[[3-(trifluoromethyl)phenyl]methyl]cyclopentane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)[C@@H]2[C@@H](CCC2)C(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 RDLVEGRXNJIRKK-FQTTXOOSSA-N 0.000 claims 1
- ZPDASYGCCGPXAX-ZOAFEQKISA-N (1s,2r)-2-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carbonyl)-n-[[3-(trifluoromethyl)phenyl]methyl]cyclopropane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)[C@@H]2[C@@H](C2)C(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 ZPDASYGCCGPXAX-ZOAFEQKISA-N 0.000 claims 1
- ZPDASYGCCGPXAX-MMBKUXRPSA-N (1s,2s)-2-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carbonyl)-n-[[3-(trifluoromethyl)phenyl]methyl]cyclopropane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)[C@@H]2[C@H](C2)C(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 ZPDASYGCCGPXAX-MMBKUXRPSA-N 0.000 claims 1
- NKXDEHWKKZTIFK-BPNWFJGMSA-N (2r)-2-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C([C@@H](C)C(=O)NCC=1C=C(C=CC=1)C(F)(F)F)C(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 NKXDEHWKKZTIFK-BPNWFJGMSA-N 0.000 claims 1
- MFIPNVIDKHUIHE-BPNWFJGMSA-N (3r)-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C([C@@H](C)C(=O)N1C(C=2C=CSC=2CC1)C=1C=CC=CC=1)C(=O)NCC1=CC=CC(C(F)(F)F)=C1 MFIPNVIDKHUIHE-BPNWFJGMSA-N 0.000 claims 1
- FECXUNIUPKYJKX-UHFFFAOYSA-N 1-(2-benzylpiperidin-1-yl)-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)N2C(CCCC2)CC=2C=CC=CC=2)=C1 FECXUNIUPKYJKX-UHFFFAOYSA-N 0.000 claims 1
- YNWIXDAGVDPVKA-UHFFFAOYSA-N 1-(2-ethylpiperidin-1-yl)-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound CCC1CCCCN1C(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 YNWIXDAGVDPVKA-UHFFFAOYSA-N 0.000 claims 1
- QUHJXXYPFPQASL-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-2-methyl-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CC2=CC=CC=C2CN1C(=O)C(C)CC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 QUHJXXYPFPQASL-UHFFFAOYSA-N 0.000 claims 1
- YXDCFSHBLRGDMN-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)-4-[4-(4-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound C1=CC(F)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)N1C2=CC=CC=C2CCC1 YXDCFSHBLRGDMN-UHFFFAOYSA-N 0.000 claims 1
- YZHHFWDIFSBIRN-UHFFFAOYSA-N 1-(3,5-dimethylpiperidin-1-yl)-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound C1C(C)CC(C)CN1C(=O)CCC(=O)N1C(C=2C=C(C)C=CC=2)C(C=CS2)=C2CC1 YZHHFWDIFSBIRN-UHFFFAOYSA-N 0.000 claims 1
- MHZJASHMNBQGSM-UHFFFAOYSA-N 1-(4-acetylpiperazin-1-yl)-4-(4-thiophen-2-yl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CN(C(=O)C)CCN1C(=O)CCC(=O)N1C(C=2SC=CC=2)C(C=CS2)=C2CC1 MHZJASHMNBQGSM-UHFFFAOYSA-N 0.000 claims 1
- LXKSOPFNNQXMBZ-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-4-[4-(4-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound C1=CC(C)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)N1CCN(CC=2C=CC=CC=2)CC1 LXKSOPFNNQXMBZ-UHFFFAOYSA-N 0.000 claims 1
- YZENHEAGWPXDGY-UHFFFAOYSA-N 1-(4-benzylpiperidin-1-yl)-4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)N1CCC(CC=2C=CC=CC=2)CC1 YZENHEAGWPXDGY-UHFFFAOYSA-N 0.000 claims 1
- ZFSOXEIZBPSFLE-UHFFFAOYSA-N 1-(4-ethylpiperazin-1-yl)-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CN(CC)CCN1C(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 ZFSOXEIZBPSFLE-UHFFFAOYSA-N 0.000 claims 1
- XOPLDQLCAMMQBU-UHFFFAOYSA-N 1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-(2-pyridin-3-ylpyrrolidin-1-yl)butane-1,4-dione Chemical compound C1CCC(C=2C=NC=CC=2)N1C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 XOPLDQLCAMMQBU-UHFFFAOYSA-N 0.000 claims 1
- FAXAKBQEZVEIJR-UHFFFAOYSA-N 1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-(4-pyridin-2-ylpiperazin-1-yl)butane-1,4-dione Chemical compound C1CN(C=2N=CC=CC=2)CCN1C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 FAXAKBQEZVEIJR-UHFFFAOYSA-N 0.000 claims 1
- SVRBNUPBZKPWEA-UHFFFAOYSA-N 1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-[5-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]butane-1,4-dione Chemical compound C1CC=2C(C(F)(F)F)=CC=CC=2CN1C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 SVRBNUPBZKPWEA-UHFFFAOYSA-N 0.000 claims 1
- MKHULQJTEANKDC-UHFFFAOYSA-N 1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-[7-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]butane-1,4-dione Chemical compound C1C2=CC(C(F)(F)F)=CC=C2CCN1C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 MKHULQJTEANKDC-UHFFFAOYSA-N 0.000 claims 1
- WNVVYHQHAMRQLB-UHFFFAOYSA-N 1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-thiomorpholin-4-ylbutane-1,4-dione Chemical compound C1CSCCN1C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 WNVVYHQHAMRQLB-UHFFFAOYSA-N 0.000 claims 1
- BDTGBLZBHURYNS-UHFFFAOYSA-N 1-(5-phenyl-3,4-dihydropyrazol-2-yl)-4-(4-thiophen-2-yl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CC(C=2C=CC=CC=2)=NN1C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CS1 BDTGBLZBHURYNS-UHFFFAOYSA-N 0.000 claims 1
- RKFLJGLQMRFQAC-UHFFFAOYSA-N 1-(azetidin-1-yl)-4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)N1CCC1 RKFLJGLQMRFQAC-UHFFFAOYSA-N 0.000 claims 1
- MXNUMNNVFGBJCT-FOSBBQIRSA-N 1-[(4ar,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C([C@H]1CCCC[C@@H]1CC1)N1C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 MXNUMNNVFGBJCT-FOSBBQIRSA-N 0.000 claims 1
- PXXDXUNMTUIHIZ-UHFFFAOYSA-N 1-[2-(5-bromopyridin-3-yl)pyrrolidin-1-yl]-4-[4-(4-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound C1=CC(F)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)N1C(C=2C=C(Br)C=NC=2)CCC1 PXXDXUNMTUIHIZ-UHFFFAOYSA-N 0.000 claims 1
- WFVCOQSNQOHDNP-UHFFFAOYSA-N 1-[2-[(4,6-dimethylpyridin-2-yl)methyl]piperidin-1-yl]-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound CC1=CC(C)=NC(CC2N(CCCC2)C(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 WFVCOQSNQOHDNP-UHFFFAOYSA-N 0.000 claims 1
- DMWPBPZHWZGINK-UHFFFAOYSA-N 1-[2-[(4,6-dimethylpyridin-2-yl)methyl]pyrrolidin-1-yl]-4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound CC1=CC(C)=NC(CC2N(CCC2)C(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=C(F)C=CC=2)=C1 DMWPBPZHWZGINK-UHFFFAOYSA-N 0.000 claims 1
- DGQWUDQGEJSGIX-UHFFFAOYSA-N 1-[2-[(5-ethylpyridin-2-yl)methyl]pyrrolidin-1-yl]-4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound N1=CC(CC)=CC=C1CC1N(C(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=C(F)C=CC=2)CCC1 DGQWUDQGEJSGIX-UHFFFAOYSA-N 0.000 claims 1
- PKPXBIQLDHHJJY-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-methyl-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)C(C)CC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 PKPXBIQLDHHJJY-UHFFFAOYSA-N 0.000 claims 1
- YHUSSEMLZLVXJD-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)piperazin-1-yl]-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]butane-1,4-dione Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)N2CCN(CC2)C=2C(=CC=CC=2)F)=C1 YHUSSEMLZLVXJD-UHFFFAOYSA-N 0.000 claims 1
- WKCVBWZOLARDPV-UHFFFAOYSA-N 1-[4-(3,5-dichloropyridin-4-yl)piperazin-1-yl]-2-methyl-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CN(C=2C(=CN=CC=2Cl)Cl)CCN1C(=O)C(C)CC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 WKCVBWZOLARDPV-UHFFFAOYSA-N 0.000 claims 1
- ZAHBRHCDVAXYTG-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-(3-methylpiperidin-1-yl)butane-1,4-dione Chemical compound C1C(C)CCCN1C(=O)CCC(=O)N1C(C=2C=C(F)C=CC=2)C(C=CS2)=C2CC1 ZAHBRHCDVAXYTG-UHFFFAOYSA-N 0.000 claims 1
- OXZYYDGFVNGBDU-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-(3-phenylpyrrolidin-1-yl)butane-1,4-dione Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)N2CC(CC2)C=2C=CC=CC=2)=C1 OXZYYDGFVNGBDU-UHFFFAOYSA-N 0.000 claims 1
- GJZBTMSGNIKIJU-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-[2-(6-methoxypyridin-3-yl)piperidin-1-yl]butane-1,4-dione Chemical compound C1=NC(OC)=CC=C1C1N(C(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=C(F)C=CC=2)CCCC1 GJZBTMSGNIKIJU-UHFFFAOYSA-N 0.000 claims 1
- HXPIGUSKEGHDSR-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-[4-[(2-fluorophenyl)methyl]piperazin-1-yl]butane-1,4-dione Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)N2CCN(CC=3C(=CC=CC=3)F)CC2)=C1 HXPIGUSKEGHDSR-UHFFFAOYSA-N 0.000 claims 1
- OZTRIRUOXRHMAU-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]butane-1,4-dione Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=C(F)C=CC=2)CC1 OZTRIRUOXRHMAU-UHFFFAOYSA-N 0.000 claims 1
- YXIFQNYFPNZTEQ-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-[4-[(4-methylphenyl)methyl]piperazin-1-yl]butane-1,4-dione Chemical compound C1=CC(C)=CC=C1CN1CCN(C(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=C(F)C=CC=2)CC1 YXIFQNYFPNZTEQ-UHFFFAOYSA-N 0.000 claims 1
- NTYNFOVXYHIMKC-UHFFFAOYSA-N 1-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-(2-pyridin-2-ylpyrrolidin-1-yl)butane-1,4-dione Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)N2C(CCC2)C=2N=CC=CC=2)=C1 NTYNFOVXYHIMKC-UHFFFAOYSA-N 0.000 claims 1
- WUVXEZMQHBTDLC-UHFFFAOYSA-N 1-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-(3-pyridin-3-ylpyrrolidin-1-yl)butane-1,4-dione Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)N2CC(CC2)C=2C=NC=CC=2)=C1 WUVXEZMQHBTDLC-UHFFFAOYSA-N 0.000 claims 1
- BPRATIYLMTWVDU-UHFFFAOYSA-N 1-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-(4-methyl-2-phenylpiperazin-1-yl)butane-1,4-dione Chemical compound C1N(C)CCN(C(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=C(C)C=CC=2)C1C1=CC=CC=C1 BPRATIYLMTWVDU-UHFFFAOYSA-N 0.000 claims 1
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- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
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- IWMSHCUIUFLBAH-UHFFFAOYSA-N 4-(1-methyl-4-phenyl-6,7-dihydro-4h-thieno[3,4-c]pyridin-5-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C1CC2=C(C)SC=C2C(C=2C=CC=CC=2)N1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 IWMSHCUIUFLBAH-UHFFFAOYSA-N 0.000 claims 1
- ODDMRXSKKYOSIV-UHFFFAOYSA-N 4-(2,5-dihydropyrrol-1-yl)-2-methyl-1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)N1CC=CC1 ODDMRXSKKYOSIV-UHFFFAOYSA-N 0.000 claims 1
- XXIIDOGBXFEVHJ-UHFFFAOYSA-N 4-(2-methyl-4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C1CC=2SC(C)=CC=2C(C=2C=CC=CC=2)N1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 XXIIDOGBXFEVHJ-UHFFFAOYSA-N 0.000 claims 1
- YDPXMCIPPBUYDZ-UHFFFAOYSA-N 4-(3-methyl-4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C1=2C(C)=CSC=2CCN(C(=O)CCC(=O)NCC=2C=C(C=CC=2)C(F)(F)F)C1C1=CC=CC=C1 YDPXMCIPPBUYDZ-UHFFFAOYSA-N 0.000 claims 1
- CPNMBCPTTIPTMW-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-2-methyl-1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)N1CCN(C(C)=O)CC1 CPNMBCPTTIPTMW-UHFFFAOYSA-N 0.000 claims 1
- HGDUSZINKIGWGZ-UHFFFAOYSA-N 4-(4-butyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C1CC=2SC=CC=2C(CCCC)N1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 HGDUSZINKIGWGZ-UHFFFAOYSA-N 0.000 claims 1
- SZNWWHYFVGTJDA-UHFFFAOYSA-N 4-(4-cyclohexyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C2CCCCC2)=C1 SZNWWHYFVGTJDA-UHFFFAOYSA-N 0.000 claims 1
- QNVFQYLOIYUCRV-UHFFFAOYSA-N 4-(4-cyclopentyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C2CCCC2)=C1 QNVFQYLOIYUCRV-UHFFFAOYSA-N 0.000 claims 1
- VUMQYZXLJXCFIV-UHFFFAOYSA-N 4-(4-cyclopropyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C2CC2)=C1 VUMQYZXLJXCFIV-UHFFFAOYSA-N 0.000 claims 1
- LWKFSQVTOCHTHQ-UHFFFAOYSA-N 4-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-2-phenyl-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)C(CC(=O)N2CC=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 LWKFSQVTOCHTHQ-UHFFFAOYSA-N 0.000 claims 1
- MZVIOJUOBUHGGO-UHFFFAOYSA-N 4-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-4-oxo-3-phenyl-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)CC(C(=O)N2CC=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 MZVIOJUOBUHGGO-UHFFFAOYSA-N 0.000 claims 1
- XMTNJWVEUPVDFQ-UHFFFAOYSA-N 4-(7-butyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C1CC=2C=CSC=2C(CCCC)N1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 XMTNJWVEUPVDFQ-UHFFFAOYSA-N 0.000 claims 1
- GCXXOSNPVRCQKU-UHFFFAOYSA-N 4-(7-cyclohexyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl)-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)CCC(=O)N2C(C=3SC=CC=3CC2)C2CCCCC2)=C1 GCXXOSNPVRCQKU-UHFFFAOYSA-N 0.000 claims 1
- UHYSHQQCAYATAT-YZOUICBYSA-N 4-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methyl-1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound COC[C@@H]1CCCN1C(=O)CC(C)C(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 UHYSHQQCAYATAT-YZOUICBYSA-N 0.000 claims 1
- WRLPPXSEXUITPK-UHFFFAOYSA-N 4-[4-(2,6-dimethylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound CC1=CC=CC(C)=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 WRLPPXSEXUITPK-UHFFFAOYSA-N 0.000 claims 1
- FEWWQNHCIJULQL-UHFFFAOYSA-N 4-[4-(2-ethylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound CCC1=CC=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 FEWWQNHCIJULQL-UHFFFAOYSA-N 0.000 claims 1
- HAOXOQBEJGOLAI-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC1=CC=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 HAOXOQBEJGOLAI-UHFFFAOYSA-N 0.000 claims 1
- JJBSTWBCYQWVPM-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]-2-methyl-1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound COC1=CC=CC=C1N1CCN(C(=O)CC(C)C(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)CC1 JJBSTWBCYQWVPM-UHFFFAOYSA-N 0.000 claims 1
- NIRWPVQHSKAJCQ-UHFFFAOYSA-N 4-[4-(2-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[2-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound CC1=CC=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CC=C1C(F)(F)F NIRWPVQHSKAJCQ-UHFFFAOYSA-N 0.000 claims 1
- JNJYARZPULGDCW-UHFFFAOYSA-N 4-[4-(2-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound CC1=CC=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 JNJYARZPULGDCW-UHFFFAOYSA-N 0.000 claims 1
- CNGQMRDWGTZVSU-UHFFFAOYSA-N 4-[4-(2-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[4-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound CC1=CC=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=C(C(F)(F)F)C=C1 CNGQMRDWGTZVSU-UHFFFAOYSA-N 0.000 claims 1
- JCOJLGMAWMMJOZ-UHFFFAOYSA-N 4-[4-(3,5-dichloropyridin-4-yl)piperazin-1-yl]-2-methyl-1-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butane-1,4-dione Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)N(CC1)CCN1C1=C(Cl)C=NC=C1Cl JCOJLGMAWMMJOZ-UHFFFAOYSA-N 0.000 claims 1
- MAQOIKPFHGUAIL-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-(pyridin-3-ylmethyl)butanamide Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2C=NC=CC=2)=C1 MAQOIKPFHGUAIL-UHFFFAOYSA-N 0.000 claims 1
- RHQRSDXQHOSKOD-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2C=C(C=CC=2)C(F)(F)F)=C1 RHQRSDXQHOSKOD-UHFFFAOYSA-N 0.000 claims 1
- QASJRXOOAYQAOB-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-phenylbutanamide Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NC=2C=CC=CC=2)=C1 QASJRXOOAYQAOB-UHFFFAOYSA-N 0.000 claims 1
- XRPJRAAXHBCSTD-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(1-methylindazol-6-yl)-4-oxobutanamide Chemical compound C1=C2N(C)N=CC2=CC=C1NC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC(F)=C1 XRPJRAAXHBCSTD-UHFFFAOYSA-N 0.000 claims 1
- ZSMUBWHJRRDRIE-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(3-imidazol-1-ylpropyl)-4-oxobutanamide Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCCCN2C=NC=C2)=C1 ZSMUBWHJRRDRIE-UHFFFAOYSA-N 0.000 claims 1
- GKCLMONLPCDFMC-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(3-morpholin-4-ylpropyl)-4-oxobutanamide Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCCCN2CCOCC2)=C1 GKCLMONLPCDFMC-UHFFFAOYSA-N 0.000 claims 1
- CKQYSTNPANZRTD-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(4-methylphenyl)-4-oxobutanamide Chemical compound C1=CC(C)=CC=C1NC(=O)CCC(=O)N1C(C=2C=C(F)C=CC=2)C(C=CS2)=C2CC1 CKQYSTNPANZRTD-UHFFFAOYSA-N 0.000 claims 1
- RCRZCPZCGNGUPE-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[(2-methoxyphenyl)methyl]-4-oxobutanamide Chemical compound COC1=CC=CC=C1CNC(=O)CCC(=O)N1C(C=2C=C(F)C=CC=2)C(C=CS2)=C2CC1 RCRZCPZCGNGUPE-UHFFFAOYSA-N 0.000 claims 1
- RZJCXZHPRBJEKK-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[(3-methylphenyl)methyl]-4-oxobutanamide Chemical compound CC1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=C(F)C=CC=2)=C1 RZJCXZHPRBJEKK-UHFFFAOYSA-N 0.000 claims 1
- IMKQMOPSVCHNRO-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[(4-fluorophenyl)methyl]-4-oxobutanamide Chemical compound C1=CC(F)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=C(F)C=CC=2)C(C=CS2)=C2CC1 IMKQMOPSVCHNRO-UHFFFAOYSA-N 0.000 claims 1
- IUNLIZQOBDXDIX-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-4-oxobutanamide Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1CNC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC(F)=C1 IUNLIZQOBDXDIX-UHFFFAOYSA-N 0.000 claims 1
- XVAAANFCKURWAC-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[2-(4-methylphenyl)ethyl]-4-oxobutanamide Chemical compound C1=CC(C)=CC=C1CCNC(=O)CCC(=O)N1C(C=2C=C(F)C=CC=2)C(C=CS2)=C2CC1 XVAAANFCKURWAC-UHFFFAOYSA-N 0.000 claims 1
- HRKOADDNSGVVHS-UHFFFAOYSA-N 4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-(pyridin-2-ylmethyl)butanamide Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2N=CC=CC=2)=C1 HRKOADDNSGVVHS-UHFFFAOYSA-N 0.000 claims 1
- SMCWKEBYMHRTLV-UHFFFAOYSA-N 4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[(4-phenylphenyl)methyl]butanamide Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 SMCWKEBYMHRTLV-UHFFFAOYSA-N 0.000 claims 1
- BQDMOFLIPFKMPH-UHFFFAOYSA-N 4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2C=C(C=CC=2)C(F)(F)F)=C1 BQDMOFLIPFKMPH-UHFFFAOYSA-N 0.000 claims 1
- ALUYMBIYQTVSTC-UHFFFAOYSA-N 4-[4-(3-methylthiophen-2-yl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C1=CSC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2C=C(C=CC=2)C(F)(F)F)=C1C ALUYMBIYQTVSTC-UHFFFAOYSA-N 0.000 claims 1
- VSEPYXUODIEBBN-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-(2-pyridin-2-ylethyl)butanamide Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCCC1=CC=CC=N1 VSEPYXUODIEBBN-UHFFFAOYSA-N 0.000 claims 1
- LLSHSYGYPAGPNN-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-pentylbutanamide Chemical compound CCCCCNC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=C(Cl)C=C1 LLSHSYGYPAGPNN-UHFFFAOYSA-N 0.000 claims 1
- KPWJOWNPIAJFKA-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-phenylbutanamide Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NC1=CC=CC=C1 KPWJOWNPIAJFKA-UHFFFAOYSA-N 0.000 claims 1
- QYNXHRLEVNFVRQ-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-propylbutanamide Chemical compound CCCNC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=C(Cl)C=C1 QYNXHRLEVNFVRQ-UHFFFAOYSA-N 0.000 claims 1
- BXSFRVUKKITEGW-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(1-methylindazol-6-yl)-4-oxobutanamide Chemical compound C1=C2N(C)N=CC2=CC=C1NC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=C(Cl)C=C1 BXSFRVUKKITEGW-UHFFFAOYSA-N 0.000 claims 1
- MBEYIDBHFXUCBL-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(2,4-dimethylphenyl)-4-oxobutanamide Chemical compound CC1=CC(C)=CC=C1NC(=O)CCC(=O)N1C(C=2C=CC(Cl)=CC=2)C(C=CS2)=C2CC1 MBEYIDBHFXUCBL-UHFFFAOYSA-N 0.000 claims 1
- UHDMNCRYEDAYPN-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(4-methoxyphenyl)-4-oxobutanamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CCC(=O)N1C(C=2C=CC(Cl)=CC=2)C(C=CS2)=C2CC1 UHDMNCRYEDAYPN-UHFFFAOYSA-N 0.000 claims 1
- WWRBYNOZUHHEJZ-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(4-methylphenyl)-4-oxobutanamide Chemical compound C1=CC(C)=CC=C1NC(=O)CCC(=O)N1C(C=2C=CC(Cl)=CC=2)C(C=CS2)=C2CC1 WWRBYNOZUHHEJZ-UHFFFAOYSA-N 0.000 claims 1
- FWSAREUYEQNCLF-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-(furan-2-ylmethyl)-4-oxobutanamide Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CO1 FWSAREUYEQNCLF-UHFFFAOYSA-N 0.000 claims 1
- FITFXAHWHPFWES-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[(3,5-dimethoxyphenyl)methyl]-4-oxobutanamide Chemical compound COC1=CC(OC)=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC(Cl)=CC=2)=C1 FITFXAHWHPFWES-UHFFFAOYSA-N 0.000 claims 1
- KSDRFXIIEYQVDK-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[(3-fluorophenyl)methyl]-4-oxobutanamide Chemical compound FC1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC(Cl)=CC=2)=C1 KSDRFXIIEYQVDK-UHFFFAOYSA-N 0.000 claims 1
- MJZZMKXPWHYSNA-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[(5-methylfuran-2-yl)methyl]-4-oxobutanamide Chemical compound O1C(C)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC(Cl)=CC=2)C(C=CS2)=C2CC1 MJZZMKXPWHYSNA-UHFFFAOYSA-N 0.000 claims 1
- IKONLIGWGDTJID-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[2-(3,4-dichlorophenyl)ethyl]-4-oxobutanamide Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCCC1=CC=C(Cl)C(Cl)=C1 IKONLIGWGDTJID-UHFFFAOYSA-N 0.000 claims 1
- ZHJBFPBZKIBDDH-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[2-(3-fluorophenyl)ethyl]-4-oxobutanamide Chemical compound FC1=CC=CC(CCNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC(Cl)=CC=2)=C1 ZHJBFPBZKIBDDH-UHFFFAOYSA-N 0.000 claims 1
- IDRFZXFSWDYTGX-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-[2-(cyclohexen-1-yl)ethyl]-4-oxobutanamide Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCCC1=CCCCC1 IDRFZXFSWDYTGX-UHFFFAOYSA-N 0.000 claims 1
- SEMPRRPYFTXYKQ-UHFFFAOYSA-N 4-[4-(4-fluoro-2-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound CC1=CC(F)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CC(C(F)(F)F)=C1 SEMPRRPYFTXYKQ-UHFFFAOYSA-N 0.000 claims 1
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- MBECWBIXKMLXEJ-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-[4-(4-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CCC(=O)N1C(C=2C=CC(C)=CC=2)C(C=CS2)=C2CC1 MBECWBIXKMLXEJ-UHFFFAOYSA-N 0.000 claims 1
- ANOPYKAMGUIRSZ-UHFFFAOYSA-N n-(4-methylphenyl)-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound C1=CC(C)=CC=C1NC(=O)CCC(=O)N1C(C=2C=C(C)C=CC=2)C(C=CS2)=C2CC1 ANOPYKAMGUIRSZ-UHFFFAOYSA-N 0.000 claims 1
- PTRKJQFDMMYJRX-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC2CCCCC2)=C1 PTRKJQFDMMYJRX-UHFFFAOYSA-N 0.000 claims 1
- IKVILAKBVQDSDK-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CCCCC1CNC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 IKVILAKBVQDSDK-UHFFFAOYSA-N 0.000 claims 1
- NMEKGBFWAOOOAL-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC1CNC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 NMEKGBFWAOOOAL-UHFFFAOYSA-N 0.000 claims 1
- ZRBZDNNUYKQLCM-UHFFFAOYSA-N n-(furan-2-ylmethyl)-n-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)CCC(=O)N(C)CC1=CC=CO1 ZRBZDNNUYKQLCM-UHFFFAOYSA-N 0.000 claims 1
- LKUDKYKIHPVHIR-UHFFFAOYSA-N n-(naphthalen-1-ylmethyl)-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C=1C=CC2=CC=CC=C2C=1CNC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 LKUDKYKIHPVHIR-UHFFFAOYSA-N 0.000 claims 1
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- HBTYYCVZACBGIP-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)methyl]-4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2C(=CC(Cl)=CC=2)Cl)=C1 HBTYYCVZACBGIP-UHFFFAOYSA-N 0.000 claims 1
- LBCVYTAPEBRBHU-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methyl]-4-[4-(4-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound COC1=CC(OC)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC(F)=CC=2)C(C=CS2)=C2CC1 LBCVYTAPEBRBHU-UHFFFAOYSA-N 0.000 claims 1
- PORZFTXVFYITLR-UHFFFAOYSA-N n-[(2,5-difluorophenyl)methyl]-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)NCC1=CC(F)=CC=C1F PORZFTXVFYITLR-UHFFFAOYSA-N 0.000 claims 1
- JJMMNCLYCOEALH-UHFFFAOYSA-N n-[(2,6-difluorophenyl)methyl]-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)NCC1=C(F)C=CC=C1F JJMMNCLYCOEALH-UHFFFAOYSA-N 0.000 claims 1
- RLLAUZHLDXBQAW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCC=2C(=CC=CC=2)Cl)=C1 RLLAUZHLDXBQAW-UHFFFAOYSA-N 0.000 claims 1
- RDTDPOKTXCMTEF-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-2-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C=1C=CC=C(F)C=1CNC(=O)C(C)CC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 RDTDPOKTXCMTEF-UHFFFAOYSA-N 0.000 claims 1
- UVKNYUBYUQNKSM-UHFFFAOYSA-N n-[(2-methoxyphenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound COC1=CC=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 UVKNYUBYUQNKSM-UHFFFAOYSA-N 0.000 claims 1
- BJDYYZMJLVERCE-UHFFFAOYSA-N n-[(2-methylphenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound CC1=CC=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 BJDYYZMJLVERCE-UHFFFAOYSA-N 0.000 claims 1
- DWZGMFKWAGWHQX-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)NCC1=CC=C(Cl)C(Cl)=C1 DWZGMFKWAGWHQX-UHFFFAOYSA-N 0.000 claims 1
- NSSJMXKSQQUUFM-UHFFFAOYSA-N n-[(3,5-difluorophenyl)methyl]-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)NCC1=CC(F)=CC(F)=C1 NSSJMXKSQQUUFM-UHFFFAOYSA-N 0.000 claims 1
- HKFALWQYRSBXJP-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)C(C)CC(=O)NCC1=CC=CC(Cl)=C1 HKFALWQYRSBXJP-UHFFFAOYSA-N 0.000 claims 1
- FPIAYQKSRKVDII-UHFFFAOYSA-N n-[(3-fluorophenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound FC1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 FPIAYQKSRKVDII-UHFFFAOYSA-N 0.000 claims 1
- LYUVLCMVULNTRT-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound COC1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 LYUVLCMVULNTRT-UHFFFAOYSA-N 0.000 claims 1
- JYIPLZUWCHPNSP-UHFFFAOYSA-N n-[(3-methylphenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound CC1=CC=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 JYIPLZUWCHPNSP-UHFFFAOYSA-N 0.000 claims 1
- RFROLFNXYWNPJP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-[4-(4-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound C1=CC(C)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=C(Cl)C=C1 RFROLFNXYWNPJP-UHFFFAOYSA-N 0.000 claims 1
- QBLNBCFKMGHGGT-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)CCC(=O)N(C)CC1=CC=C(F)C=C1 QBLNBCFKMGHGGT-UHFFFAOYSA-N 0.000 claims 1
- QZSDJGSKSKGNJI-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-2-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C(C)CC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 QZSDJGSKSKGNJI-UHFFFAOYSA-N 0.000 claims 1
- MQIALFUGXPXNCN-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 MQIALFUGXPXNCN-UHFFFAOYSA-N 0.000 claims 1
- PORIGQCYHJUUOD-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=CC(C)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 PORIGQCYHJUUOD-UHFFFAOYSA-N 0.000 claims 1
- KTMDRRXDTBTMMP-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]-2-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C=1NC2=CC=CC=C2C=1CCNC(=O)C(C)CC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 KTMDRRXDTBTMMP-UHFFFAOYSA-N 0.000 claims 1
- DBPDUPPBUYYRRS-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 DBPDUPPBUYYRRS-UHFFFAOYSA-N 0.000 claims 1
- PITIZUMAWBXMQJ-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-4-[4-(4-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound C1=CC(F)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCCC1=CC=CC=C1Cl PITIZUMAWBXMQJ-UHFFFAOYSA-N 0.000 claims 1
- IHPRQGULLZEOQG-UHFFFAOYSA-N n-[2-(2-methoxyphenyl)ethyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound COC1=CC=CC=C1CCNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 IHPRQGULLZEOQG-UHFFFAOYSA-N 0.000 claims 1
- PSYBHPKFWHFMNL-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-4-[4-(4-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-methyl-4-oxobutanamide Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)C(=O)CCC(=O)N1C(C=2C=CC(F)=CC=2)C(C=CS2)=C2CC1 PSYBHPKFWHFMNL-UHFFFAOYSA-N 0.000 claims 1
- KYPHYFQYLRASDD-UHFFFAOYSA-N n-[2-(3,5-dimethoxyphenyl)ethyl]-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound COC1=CC(OC)=CC(CCNC(=O)CC(C)C(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 KYPHYFQYLRASDD-UHFFFAOYSA-N 0.000 claims 1
- BRNILTDOMOYQFV-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound CC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCCC=2C=C(Cl)C=CC=2)=C1 BRNILTDOMOYQFV-UHFFFAOYSA-N 0.000 claims 1
- OSMDNMPOEAHFMW-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-4-[4-(3-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound FC1=CC=CC(C2C=3C=CSC=3CCN2C(=O)CCC(=O)NCCC=2C=CC(Cl)=CC=2)=C1 OSMDNMPOEAHFMW-UHFFFAOYSA-N 0.000 claims 1
- NEZYEGSOEQBWDO-UHFFFAOYSA-N n-[3-(3,4-dihydro-2h-quinolin-1-yl)propyl]-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CCC2=CC=CC=C2N1CCCNC(=O)CC(C)C(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 NEZYEGSOEQBWDO-UHFFFAOYSA-N 0.000 claims 1
- UVTBXDBXSHDTLE-UHFFFAOYSA-N n-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=CC=C(C(F)(F)F)C(F)=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 UVTBXDBXSHDTLE-UHFFFAOYSA-N 0.000 claims 1
- BMPHRNMMLVKTRG-UHFFFAOYSA-N n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound FC1=CC=C(C(F)(F)F)C=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 BMPHRNMMLVKTRG-UHFFFAOYSA-N 0.000 claims 1
- XRYPGGZIFGGYCQ-UHFFFAOYSA-N n-[[2-methyl-3-(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=CC=C(C(F)(F)F)C(C)=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 XRYPGGZIFGGYCQ-UHFFFAOYSA-N 0.000 claims 1
- YZWKRZJENABYMN-UHFFFAOYSA-N n-[[2-methyl-5-(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound CC1=CC=C(C(F)(F)F)C=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 YZWKRZJENABYMN-UHFFFAOYSA-N 0.000 claims 1
- BADFRIHEZVGDIB-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 BADFRIHEZVGDIB-UHFFFAOYSA-N 0.000 claims 1
- QKRYVNUUHNLNGQ-UHFFFAOYSA-N n-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound FC(F)(F)C1=CC(F)=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 QKRYVNUUHNLNGQ-UHFFFAOYSA-N 0.000 claims 1
- CHNSODVKUDMXKI-UHFFFAOYSA-N n-[[3-methyl-5-(trifluoromethoxy)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound FC(F)(F)OC1=CC(C)=CC(CNC(=O)CCC(=O)N2C(C=3C=CSC=3CC2)C=2C=CC=CC=2)=C1 CHNSODVKUDMXKI-UHFFFAOYSA-N 0.000 claims 1
- YZDXRGJXNAJJDW-UHFFFAOYSA-N n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 YZDXRGJXNAJJDW-UHFFFAOYSA-N 0.000 claims 1
- WRNXOGHYPRFUJR-UHFFFAOYSA-N n-[[4-methyl-3-(trifluoromethyl)phenyl]methyl]-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1CNC(=O)CCC(=O)N1C(C=2C=CC=CC=2)C(C=CS2)=C2CC1 WRNXOGHYPRFUJR-UHFFFAOYSA-N 0.000 claims 1
- RAZWIGDZQVANEW-UHFFFAOYSA-N n-benzyl-2-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-n-(2-phenylethyl)butanamide Chemical compound C=1C=CC=CC=1CCN(CC=1C=CC=CC=1)C(=O)C(C)CC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 RAZWIGDZQVANEW-UHFFFAOYSA-N 0.000 claims 1
- WIGSFLJMMPECJS-UHFFFAOYSA-N n-benzyl-4-[4-(4-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-propan-2-ylbutanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC(F)=CC=2)N1C(=O)CCC(=O)N(C(C)C)CC1=CC=CC=C1 WIGSFLJMMPECJS-UHFFFAOYSA-N 0.000 claims 1
- PLSXIKJJZXJGPB-UHFFFAOYSA-N n-benzyl-4-[4-(4-fluorophenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-n-methyl-4-oxobutanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC(F)=CC=2)N1C(=O)CCC(=O)N(C)CC1=CC=CC=C1 PLSXIKJJZXJGPB-UHFFFAOYSA-N 0.000 claims 1
- JQLPQPFRLUXVTI-UHFFFAOYSA-N n-benzyl-4-[4-(4-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound C1=CC(C)=CC=C1C1C(C=CS2)=C2CCN1C(=O)CCC(=O)NCC1=CC=CC=C1 JQLPQPFRLUXVTI-UHFFFAOYSA-N 0.000 claims 1
- AIQAEPLCZZDKNT-UHFFFAOYSA-N n-benzyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 AIQAEPLCZZDKNT-UHFFFAOYSA-N 0.000 claims 1
- BJAUXYNAPQEDSV-UHFFFAOYSA-N n-benzyl-n-ethyl-4-[4-(4-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC(C)=CC=2)N1C(=O)CCC(=O)N(CC)CC1=CC=CC=C1 BJAUXYNAPQEDSV-UHFFFAOYSA-N 0.000 claims 1
- NHQSDWMTEHWTAB-UHFFFAOYSA-N n-butyl-n-ethyl-3-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound CCCCN(CC)C(=O)CC(C)C(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 NHQSDWMTEHWTAB-UHFFFAOYSA-N 0.000 claims 1
- BDEZWRJHQHGWKW-UHFFFAOYSA-N n-cyclohexyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butanamide Chemical compound C1CCCCC1NC(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC=C1 BDEZWRJHQHGWKW-UHFFFAOYSA-N 0.000 claims 1
- GIQMPSONEAFUTJ-UHFFFAOYSA-N n-cyclohexyl-n-ethyl-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxobutanamide Chemical compound C1CC=2SC=CC=2C(C=2C=C(C)C=CC=2)N1C(=O)CCC(=O)N(CC)C1CCCCC1 GIQMPSONEAFUTJ-UHFFFAOYSA-N 0.000 claims 1
- INRTVKPUTOUSFQ-UHFFFAOYSA-N n-ethyl-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-propan-2-ylbutanamide Chemical compound CCN(C(C)C)C(=O)CCC(=O)N1CCC=2SC=CC=2C1C1=CC=CC(C)=C1 INRTVKPUTOUSFQ-UHFFFAOYSA-N 0.000 claims 1
- UEJXRUJSPCHRGZ-UHFFFAOYSA-N n-methyl-4-[4-(3-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-(2-pyridin-4-ylethyl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=C(C)C=CC=2)N1C(=O)CCC(=O)N(C)CCC1=CC=NC=C1 UEJXRUJSPCHRGZ-UHFFFAOYSA-N 0.000 claims 1
- VFHUWCURKCVYIX-UHFFFAOYSA-N n-methyl-4-[4-(4-methylphenyl)-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]-4-oxo-n-(2-phenylethyl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC(C)=CC=2)N1C(=O)CCC(=O)N(C)CCC1=CC=CC=C1 VFHUWCURKCVYIX-UHFFFAOYSA-N 0.000 claims 1
- VNBPKLQGJPOQHU-UHFFFAOYSA-N n-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-n-(2-pyridin-4-ylethyl)butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)CCC(=O)N(C)CCC1=CC=NC=C1 VNBPKLQGJPOQHU-UHFFFAOYSA-N 0.000 claims 1
- ARFGTSVCLIETBV-UHFFFAOYSA-N n-methyl-4-oxo-4-(4-phenyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-n-[[3-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound C1CC=2SC=CC=2C(C=2C=CC=CC=2)N1C(=O)CCC(=O)N(C)CC1=CC=CC(C(F)(F)F)=C1 ARFGTSVCLIETBV-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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Claims (13)
1. Supstituirani tetrahidrotienopiridini opće formule (1)
[image]
naznačeni time da
A1 predstavlja S, A2 predstavlja CR14 i A3 predstavlja CR15; ili
A1 predstavlja CR13, A2 predstavlja S i A3 predstavlja CR15; ili
A1 predstavlja CR13, A2 predstavlja CR14 i A3 predstavlja S;
R0 predstavlja C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran; aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran; C1-8-alkil premošten C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; ili C1-8-alkil premošten aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran;
R1 predstavlja H; F; Cl; Br; CN; ili R0;
R2 predstavlja H; F; Cl; Br; ili C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran;
ili R1 i R2, zajedno sa atomom ugljika koji im je dodan kao član prstena, tvore C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, u svakom slučaju proizvoljno kondenziran sa (hetero)arilom, nesupstituiranim ili mono- ili poli-supstituiranim;
R3, R4, R5, R6 neovisno jedan od drugoga predstavljaju H; F; Cl; Br; C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; ili fenil, nesupstituiran ili mono- ili poli-supstituiran;
R7 predstavlja H; F; Cl; Br; CN; R0; OR0; O-C(=O)-R0; O-C(=O)-O-R0; O-(C=O)-NH-R0; O-C(=O)-N(R0)2; NH-R0; N(R0)2; NH-C(=O)-R0; NH-C(=O)-OR0; NH-C(=O)-NH-R0; NH-C(=O)-N(R0)2; NR0-C(=O)-R0; NR0-C(=O)-O-R0; NR0-C(=O)-NH2; NR0-C(=O)-NH-R0; NR0-C(=O)-N(R0)2; NH-S(=O)2OH; NH-S(=O)2R0; NH-S(=O)2OR0; NH-S(=O)2NH2; NH-S(=O)2NHR0; NH-S(=O)2N(R0)2; NR0-S(=O)2OH; NR0-S(=O)2R0; NR0-S(=O)2OR0; NR0-S(=O)2NH2; NR0-S(=O)2NHR0; NR0-S(=O)2N(R0)2; C(=O)-OH; C(=O)-OR0; C(=O)-NH2; C(=O)-NH-R0; C(=O)-N(R0)2; S(=O)2-OH; S(=O)2OR0; S(=O)2-NH2; S(=O)2-NH-R0; S(=O)2-N(R0)2;
R8 predstavlja H; F; Cl; Br; CN; ili C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran;
R9 predstavlja H; F; Cl; Br; CN; C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran; aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran; C1-8-alkil premošten C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; ili C2-8-alkil premošten aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; O-C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; O-C3-7-cikloalkil ili O-heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran; O-C1-8-alkil premošten C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; ili O-C1-8-alkil premošten aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; O-C(=O)-R0; O-C(=O)-O-R0; O-(C=O)-NH-R0; O-C(=O)-N(R0)2; NH-R0; N(R0)2; NH-C(=O)-R0; NH-C(=O)-O-R0; NH-C(=O)-NH-R0; NH-C(=O)-N(R0)2; NR0-C(=O)-R0; NR0-C(=O)-O-R0; NR0-C(=O)-NH2; NR0-C(=O)-NH-R0; NR0-C(=O)-N(R0)2; NH-S(=O)2OH; NH-S(=O)2R0; NH-S(=O)2OR0; NH-S(=O)2NH2; NH-S(=O)2NHR0; NH-S(=O)2N(R0)2; NR0-S(=O)2OH; NR0-S(=O)2R0; NR0-S(=O)2OR0; NR0-S(=O)2NH2; NR0-S(=O)2NHR0; NR0-S(=O)2N(R0)2; C(=O)-OH; C(=O)-OR0; C(=O)-NH2; C(=O)-NH-R0; C(=O)-N(R0)2; S(=O)2-OH; S(=O)2OR0; S(=O)2-NH2; S(=O)2-NH-R0; S(=O)2-N(R0)2;
R10 predstavlja H; F; Cl; Br; CN; ili C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran;
ili R7 i R9, zajedno sa atomima ugljika koji su im dodani kao članovi prstena, tvore C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, proizvoljno kondenziran sa (hetero)arilom, nesupstituiranim ili mono- ili poli-supstituiranim;
ili R7 i R8; ili R9 i R10; zajedno sa atomima ugljika koji su im dodani kao članovi prstena, tvore C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, u svakom slučaju proizvoljno kondenziran sa (hetero)arilom, nesupstituiranim ili mono- ili poli-supstituiranim;
R11 predstavlja H; C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; ili C3-7-cikloalkil, zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran;
R12 predstavlja C2-16-alkil, zasićen ili nezasićen; razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran; aril ili heteroaril, nesupstituiran ili mono- ili poli-supstituiran; C1-8-alkil premošten C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; C1-8-alkil premošten aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran; pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran;
ili R11 i R12, zajedno sa atomom dušika koji im je dodan kao član prstena, tvore heterociklil, zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, proizvoljno kondenziran sa (hetero)arilom, nesupstituiranim ili mono- ili poli-supstituiranim;
R13, R14 i R15 svaki neovisno od drugih označava H; F; Cl; Br; I; NO; NO2; CF3; CN; R0; C(=O)H; C(=O)R0; CO2H; C(=O)OR0; CONH2; C(=O)NHR0; C(=O)N(R0)2; OH; OR0; 0-(C1-8-alkil)-O; O-C(=O)-R0; O-C(=O)-O-R0; O-(C=O)-NH-R0; O-C(=O)-N(R0)2; O-S(=O)2-R0; O-S(=O)2OH; O-S(=O)2OR0; O-S(=O)2NH2; O-S(=O)2NHR0; O-S(=O)2N(R0)2; NH2; NH-R0; N(R0)2; NH-C(=O)-R0; NH-C(=O)-O-R0; NH-C(=O)-NH-R0; NH-C(=O)-N(R0)2; NR0-C(=O)-R0; NR0-C(=O)-O-R0; NR0-C(=O)-NH2; NR0-C(=O)-NH-R0; NR0-C(=O)-N(R0)2; NH-S(=O)2OH; NH-S(=O)2R0; NH-S(=O)2OR0; NH-S(=O)2NH2; NH-S(=O)2NHR0; NH-S(=O)2N(R0)2; NR0-S(=O)2OH; NR0-S(=O)2R0; NR0-S(=O)2OR0; NR0-S(=O)2NH2; NR0-S(=O)2NHRO; NR0-S(=O)2N(R0)2; SH; SR0; S(=O)R0; S(=O)2R0; S(=O)2OH; S(=O)2OR0; S(=O)2NH2; S(=O)2NHR0; ili S(=O)2N(R0)2;
pri čemu "alkil supstituiran", "heterociklil supstituiran" i "cikloalkil supstituiran" označavaju supstituciju jednog ili više atoma vodika, u svakom slučaju neovisno jedan od drugoga, sa F; Cl; Br; I; CN; CF3; =O; =NH; =C(NH2)2; NO2; R0; C(=O)H; C(=O)R0; CO2H; C(=O)OR0; CONH2; C(=O)NHR0; C(=O)N(R0)2; OH; OR0; 0-(C1-8-alkil)-O; O-C(=O)-R0; O-C(=O)-O-R0; O-(C=O)-NH-R0; O-C(=O)-N(R0)2; O-S(=O)2-R0; O-S(=O)2OH; O-S(=O)2OR0; O-S(=O)2NH2; O-S(=O)2NHR0; O-S(=O)2N(R0)2; NH2; NH-R0; N(R0)2; NH-C(=O)-R0; NH-C(=O)-OR0; NH-C(=O)-NH-R0; NH-C(=O)-N(R0)2; NR0-C(=O)-R0; NR0-C(=O)-O-R0; NR0-C(=O)-NH2; NR0-C(=O)-NH-R0; NR0-C(=O)-N(R0)2; NH-S(=O)2OH; NH-S(=O)2R0; NH-S(=O)2OR0; NH-S(=O)2NH2; NH-S(=O)2NHR0; NH-S(=O)2N(R0)2; NR0-S(=O)2OH; NR0-S(=O)2R0; NR0-S(=O)2OR0; NR0-S(=O)2NH2; NR0-S(=O)2NHR0; NR0-S(=O)2N(R0)2; SH; SR0; S(=O)R0; S(=O)2R0; S(=O)2OH; S(=O)2OR0; S(=O)2NH2; S(=O)2NHR0; S(=O)2N(R0)2;
pri čemu "aril supstituiran " i "heteroaril supstituiran " označavaju supstituciju jednog ili više atoma vodika, u svakom slučaju neovisno jedan od drugoga, sa F; Cl; Br; I; NO; NO2; CF3; CN; R0; C(=O)H; C(=O)R0; CO2H; C(=O)OR0; CONH2; C(=O)NHR0; C(=O)N(R0)2; OH; OR0; O-(C1-8-alkil)-O; O-C(=O)-R0; O-C(=O)-OR0; O-(C=O)-NH-R0; O-C(=O)-N(R0)2; O-S(=O)2-R0; O-S(=O)2OH; O-S(=O)2OR0; O-S(=O)2NH2; O-S(=O)2NHR0; O-S(=O)2N(R0)2; NH2; NH-R0; N(R0)2; NH-C(=O)-R0; NH-C(=O)-O-R0; NH-C(=O)-NH-R0; NH-C(=O)-N(R0)2; NR0-C(=O)-R0; NR0-C(=O)-O-R0; NR0-C(=O)-NH2; NR0-C(=O)-NH-R0; NR0-C(=O)-N(R0)2; NH-S(=O)2OH; NH-S(=O)2R0; NH-S(=O)2OR0; NH-S(=O)2NH2; NH-S(=O)2NHR0; NH-S(=O)2N(R0)2; NR0-S(=O)2OH; NR0-S(=O)2R0; NR0-S(=O)2OR0; NR0-S(=O)2NH2; NR0-S(=O)2NHR0; NR0-S(=O)2N(R0)2; SH; SR0; S(=O)R0; S(=O)2R0; S(=O)2OH; S(=O)2OR0; S(=O)2NH2; S(=O)2NHR0; S(=O)2N(R0)2;
uz izuzetak slijedećih spojeva:
1-morfolino-4-(4-(tiofen-2-il)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-butan-1,4-diona,
1-(4-acetilpiperazin-1-il)-4-(4-(tiofen-2-il)-6, 7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-diona, te
1-(3-fenil-4,5-dihidropirazol-1-il)-4-(4-(tiofen-2-il)-6,7-dihidrotieno-[3,2-c]piridin-5(4H)-il)butan-1,4-diona;
u obliku slobodnih spojeva ili soli fiziološki prihvatljivih kiselina ili baza.
2. Tetrahidrotienopiridini prema zahtjevu 1, naznačeni time da R12 predstavlja C4-16-alkil, zasićen ili nezasićen; razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran; aril ili heteroaril, nesupstituiran ili mono- ili poli-supstituiran; C1-8-alkil premošten C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; C1-8-alkil premošten aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran.
3. Tetrahidrotienopiridini prema bilo kojem od prethodnih zahtjeva, naznačeni time da
R7 predstavlja H; F; Cl; Br; CN; OH; NH2; C1-8-alkil, O-C1-8-alkil, NH-C1-8-alkil, N(C1-8-alkil)2, u svakom slučaju zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; fenil ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran; C1-2-alkil premošten fenil ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran;
R9 predstavlja H; F; Cl; Br; CN; OH; NH2; C1-8-alkil, O-C1-8-alkil, NH-C1-8-alkil, N(C1-8-alkil)2, u svakom slučaju zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; fenil ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran; C2-alkil premošten fenil ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran.
4. Tetrahidrotienopiridini prema bilo kojem od prethodnih zahtjeva, naznačeni time da
R1 i R2 svaki označava H;
ili R2 označava H i R1 nije H.
5. Tetrahidrotienopiridini prema bilo kojem od prethodnih zahtjeva koji imaju jednu od općih formula (1a), (1b) ili (1c)
[image]
[image]
[image]
naznačeni time da R13, R14 i R15 svaki neovisno od drugih označava H; F; Cl; Br; I; NO; NO2; CN; NH2 ; NH-C1-8-alkil; N(C1-8-alkil)2; NH-C(=O)C1-8-alkil; NH-C(=O)-aril; NH-C(=O)-heteroaril; C1-8-alkil; CF3; CHO; C(=O)C1-8-alkil; C(=O)aril; C(=O)heteroaril; CO2H; C(=O)O-C1-8-alkil; C(=O)O-aril; C(=O)O-heteroaril; CONH2; C(=O)NH-C1-8-alkil; C(=O)N(C1-8-alkil)2; C(=O)NH-aril; C(=O)N(aril)2; C(=O)NH-heteroaril; C(=O)N(heteroaril)2; C(=O)N(C1-8-alkil)(aril); C(=O)N(C1-8-alkil)(heteroaril); C(=O)N(heteroaril)(aril); OH; O-C1-8-alkil; OCF3; O-(C1-8-alkil)-O; O-(C1-8-alkil)-O-C1-8-alkil; O-benzil; O-aril; O-heteroaril; O-C(=O)C1-8-alkil; O-C(=O)aril; O-C(=O)heteroaril; SH; S-C1-8-alkil; SCF3; S-benzil; S-aril; S-heteroaril; aril; heteroaril; C3-7-cikloalkil; heterociklil ili C1-8-alkil premošten aril, heteroaril, C3-7-cikloalkil ili heterociklil.
6. Tetrahidrotienopiridini prema bilo kojem od prethodnih zahtjeva, naznačeni time da
R3, R4, R5 i R6 neovisno jedan od drugoga predstavljaju H, C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; ili fenil, nesupstituiran ili mono- ili poli-supstituiran.
7. Tetrahidrotienopiridini prema bilo kojem od prethodnih zahtjeva, naznačeni time da R8 predstavlja H; ili C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran;
R10 predstavlja H; ili C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran.
8. Tetrahidrotienopiridini prema bilo kojem od prethodnih zahtjeva, naznačeni time da
R11 predstavlja H; C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, C3-7-cikloalkil, zasićen ili nezasićen; ili benzil, nesupstituiran ili mono- ili poli-supstituiran.
9. Tetrahidrotienopiridini prema bilo kojem od prethodnih zahtjeva, naznačeni time da R12 predstavlja C4-16-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; ili je odabran od slijedećih djelomičnih struktura A, B i C
[image]
pri čemu
n = 0, 1, 2, 3, 4, 5, 6, 7 ili 8;
m = 0, 1, 2 ili 3;
prsten X može sadržavati jedan ili dva atoma N kao član(ove) prstena;
prsten Y sadrži barem 1 heteroatom odabran od N, O i S i može sadržavati do 3 heteroatoma neovisno odabrana jedan od drugoga od N, O i S;
R18 i R19 neovisno jedan od drugoga označavaju H; F; Cl; Br; I; NO; NO2; CF3; CN; R0; C(=O)H; C(=O)R0; CO2H; C(=O)OR0; CONH2; C(=O)NHR0; C(=O)N(R0)2; OH; OR0; O-(C1-8-alkil)-O; O-C(=O)-R0; O-C(=O)-O-R0; O-(C=O)-NH-R0; O-C(=O)-N(R0)2; O-S(=O)2-R0; O-S(=O)2OH; O-S(=O)2OR0; O-S(=O)2NH2; O-S(=O)2NHR0; O-S(=O)2N(R0)2; NH2; NH-R0; N(R0)2; NH-C(=O)-R0; NH-C(=O)-O-R0; NH-C(=O)-NH-R0; NH-C(=O)-N(R0)2; NR0-C(=O)-R0; NR0-C(=O)-O-R0; NR0-C(=O)-NH2; NR0-C(=O)-NH-R0; NR0-C(=O)-N(R0)2; NH-S(=O)2OH; NH-S(=O)2R0; NH-S(=O)2OR0; NH-S(=O)2NH2; NH-S(=O)2NHR0; NH-S(=O)2N(R0)2; NR0-S(=O)2OH; NR0-S(=O)2R0; NR0-S(=O)2OR0; NR0-S(=O)2NH2; NR0-S(=O)2NHR0; NR0-S(=O)2N(R0)2; SH; SR0; S(=O)R0; S(=O)2R0, S(=O)2OH; S(=O)2OR0; S(=O)2NH2; S(=O)2NHR0; ili S(=O)2N(R0)2;
ili R18 i R19, zajedno sa atomima ugljika ili dušika koji su im dodani kao članovi prstena, tvore aril ili heteroaril kondenziran sa fenilnim prstenom i u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran; ili C3-7-cikloalkil ili heterociklil kondenziran sa fenilnim prstenom i u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran;
R20 i R21 neovisno jedan od drugoga označavaju H ili C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran.
10. Tetrahidrotienopiridini prema bilo kojem od zahtjeva 1 ili 3 do 7, naznačeni time da R11 i R12, zajedno sa atomom dušika koji im je dodan kao član prstena, tvore jedan od slijedećih prstenova
[image]
[image]
pri čemu
Z = O ili S;
o = 0, 1 ili 2;
p = 0 ili 1;
R22, R23, R24, R25 i R26 neovisno jedan od drugoga označavaju H; C1-8-alkil, zasićen ili nezasićen; razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran; C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran; aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran; C1-8-alkil premošten C3-7- cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, mono- ili poli-supstituiran; C1-8-alkil premošten aril ili heteroaril, u svakom slučaju nesupstituiran ili mono- ili poli-supstituiran, pri čemu alkilni lanac u svakom slučaju može biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran;
ili R22 i R23, sa atomom(ima) ugljika koji su im dodani kao član(ovi) prstena tvore C3-7-cikloalkil ili heterociklil, u svakom slučaju zasićen ili nezasićen, nesupstituiran ili mono- ili poli-supstituiran, proizvoljno kondenziran sa (hetero)arilom, nesupstituiranim ili mono- ili poli-supstituiranim; ili tvore kondenzirani aril ili heteroaril, nesupstituiran ili mono- ili poli-supstituiran;
R27 i R28 neovisno jedan od drugoga označavaju H; C1-8-alkil, zasićen ili nezasićen; razgranat ili nerazgranat, nesupstituiran ili mono- ili poli-supstituiran;
R34 i R35 neovisno jedan od drugoga označavaju H; F; Cl; Br; I; NO; NO2; CN; NH2; NH-C1-8-alkil; N(C1-8-alkil)2; NH-C(=O)C1-8-alkil; NH-C(=O)-aril; NH-C(=O)-heteroaril; C1-8-alkil; CF3; C(=O)H; C(=O)C1-8-alkil; C(=O)aril; C(=O)heteroaril; CO2H; C(=O)O-C1-8-alkil; C(=O)O-aril; C(=O)O-heteroaril; CONH2; C(=O)NH-C1-8-alkil; C(=O)N(C1-8-alkil)2; C(=O)NH-aril; C(=O)N(aril)2; C(=O)NH-heteroaril; C(=O)N(heteroaril)2; C(=O)N(C1-8-alkil)(aril); C(=O)N(C1-8-alkil)(heteroaril); C(=O)N(aril)(heteroaril); OH; O-C1-8-alkil; O-C1-8-alkil-OH; OCF3; O-(C1-8-alkil)-O-C1-8-alkil; O-benzil; O-aril; O-heteroaril; O-C(=O)C1-8-alkil; O-C(=O)aril; O-C(=O)heteroaril; SH; S-C1-8-alkil; SCF3; S-benzil; S-aril; S-heteroaril; aril; heteroaril; C3-7- cikloalkil; heterociklil; ili C1-8-alkil premošten aril, heteroaril, C3-7-cikloalkil ili heterociklil.
11. Tetrahidrotienopiridini prema zahtjevu 1 naznačeni tima da su odabrani iz slijedeće skupine:
1 4-okso-4-(4-(tiofen-2-il)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
2 4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
3 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
4 4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
5 4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
6 4-(4-(2-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
7 4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
8 4-okso-4-(4-o-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
9 4-okso-4-(7-fenil-4,5-dihidrotieno[2,3-c]piridin-6(7H)-il)-N-(3-(trifluorometil)benzil)butanamid;
10 4-(2-metil-4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
11 N-(4-metilbenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
12 N-benzil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
13 4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(4-(trifluorometil)benzil)butanamid;
14 N-(2-metoksibenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
15 N-(3-metoksibenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
16 N-(4-metoksibenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
17 4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(2-(trifluorometil)benzil)butanamid;
18 N-(3-fluorobenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
19 N-(3-metilbenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
20 4-(3-metil-4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
21 4-(4-cikloheksil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
22 4-(4-izopropil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
23 4-(4-butil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
24 N-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
25 4-okso-N-fenetil-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
26 N-(2-metilbenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
27 4-okso-2-fenil-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
28 (R)-2-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
29 4-okso-3-fenil-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
30 4-(6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-3-fenil-N-(3-(trifluorometil)benzil)butanamid;
31 rac. (1 S,2R)-2-(4-fenil-4,5,6,7-tetrahidrotieno[3,2-c]piridin-5-karbonil)-N-(3-(trifluorometil)benzil)cikloheksankarboksamid;
32 rac. (1 S)-2-(4-fenil-4,5,6,7-tetrahidrotieno[3,2-c]piridin-5-karbonil)-N-(3-(trifluorometil)benzil)cikloheksankarboksamid;
33 rac. (1 S,2R)-2-(4-fenil-4,5,6,7-tetrahidrotieno[3,2-c]piridin-5-karbonil)-N-(3-(trifluorometil)benzil)ciklopentanekarboksamid;
34 (R)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
35 (-)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
36 (+)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
37 4-(6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-2-fenil-N-(3-(trifluorometil)benzil)butanamid;
38 N-(3,5-bis(trifluorometil)benzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
39 N-(2-fluoro-5-(trifluorometil)benzil)-4-okso-4-(4-fenil-6,7-dihidrotieno-[3,2-c]piridin-5(4H)-il)butanamid;
40 N-(2-fluoro-3-(trifluorometil)benzil)-4-okso-4-(4-fenil-6,7-dihidrotieno-[3,2-c]piridin-5(4H)-il)butanamid;
41 N-(3-fluoro-5-(trifluorometil)benzil)-4-okso-4-(4-fenil-6,7-dihidrotieno-[3,2-c]piridin-5(4H)-il)butanamid;
42 rac. (1S,2R)-2-(4-fenil-4,5,6,7-tetrahidrotieno[3,2-c]piridin-5-karbonil)-N-(3-(trifluorometil)benzil)ciklopropankarboksamid;
43 N-(3,4-difluorobenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
44 4-okso-4-(5-fenil-4,5-dihidrotieno[2,3-c]piridin-6(7H)-il)-N-(3-(trifluorometil)benzil)butanamid;
45 4-(1-metil-4-fenil-6,7-dihidrotieno[3,4-c]piridin-5(4H)-il)-4-okso-N-(3-(trifluorometil)benzil)butanamid;
46 N-(4-metoksifenil)-4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
47 N-(1 -metil-1H-indazol-6-il)-4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
48 N-benzil-4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
49 4-okso-N-fenetil-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
50 4-okso-N-(piridin-4-ilmetil)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
51 4-okso-N-(3-fenilpropil)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
52 N-(benzo[c][1,2,5]tiadiazol-4-il)-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
53 N-(1 -metil-1H-indazol-6-il)-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butanamid;
54 4-okso-N-(piridin-2-ilmetil)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
55 1-(4-metilpiperazin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
56 3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(piridin-2-ilmetil)butanamid;
57 4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(tiofen-2-ilmetil)butanamid;
58 N-(2-klorofenil)-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
59 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(furan-2-ilmetil)-4-oksobutanamid;
60 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-propilbutanamid;
61 N-(2-klorobenzil)-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
62 N-(2,4-diklorobenzil)-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
63 N-(4-fluorobenzil)-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
64 N-(3,4-diklorobenzil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
65 N-(2,5-difluorobenzil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
66 3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-(trifluorometil)benzil)butanamid;
67 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-morfolinobutan-1,4-dion;
68 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(4-fluorofenil)piperazin-1-il)butan-1,4-dion;
69 2-metil-N-(2-(5-metil-1H-pirazol-1-il)etil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
70 N-(naftalen-1-ilmetil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
71 4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(4-metilbenzil)-4-oksobutanamid;
72 N-(benzo[d][1,3]dioksol-5-ilmetil)-4-(4-(4-fluorofenil)-6,7-dihidrotieno-[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
73 4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(2-(trifluorometil)benzil)butanamid;
74 4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(naftalen-1-ilmetil)-4-oksobutanamid;
75 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-fluorobenzil)-4-oksobutanamid;
76 2-metil-N-(1-metil-1H-indazol-6-il)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
77 N-(4-metoksibenzil)-2-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butanamid;
78 2-metil-1-(4-metilpiperazin-1-il)-4-(4-fenil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butan-1,4-dion;
79 N-(2-(1H-indol-3-il)etil)-2-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
80 N-(2-fluorobenzil)-2-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
81 2-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(2-(trifluorometil)benzil)butanamid;
82 4-okso-N-(2-(piperidin-1-il)etil)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
83 4-okso-N-((tetrahidrofuran-2-il)metil)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
84 N-(4-klorobenzil)-4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
85 N-(2,3-diklorobenzil)-4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
86 4-okso-N-(2-(tiofen-2-il)etil)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
87 N-(cikloheksilmetil)-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
88 N-(3-klorofenetil)-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
89 N-(3,3-difenilpropil)-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
90 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-morfolinopropil)-4-oksobutanamid;
91 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(piridin-3-ilmetil)butanamid;
92 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-metilbenzil)-4-oksobutanamid;
93 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(4-metilfenetil)-4-oksobutanamid;
94 3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(4-fenilbutil)butanamid;
95 N-(bifenil-4-ilmetil)-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
96 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(2-metoksibenzil)-4-oksobutanamid;
97 N-(4-klorofenetil)-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
98 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-((5-metil-3-fenilizoksazol-4-il)metil)-4-oksobutanamid;
99 N-(2,6-difluorobenzil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
100 N-(3,5-difluorobenzil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
101 N-(3-klorobenzil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
102 N-(3,5-dimetoksifenetil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
103 N-(3,4-difluorobenzil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
104 N-(2,4-diklorofenetil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
105 N-(2-(1H-1,2,4-triazol-1-il)etil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
106 4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(2-metilbenzil)-4-oksobutanamid;
107 N-(4-fluorofenetil)-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
108 4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-((5-metilizoksazol-3-il)metil)-4-oksobutanamid;
109 N-(2-klorofenetil)-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
110 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(2-ciklo-hexeniletil)-4-oksobutanamid;
111 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3,5-dimetoksibenzil)-4-oksobutanamid;
112 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3,4-diklorofenetil)-4-oksobutanamid;
113 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(3-fluorofenetil)-4-oksobutanamid;
114 1-(3-fenilpiperidin-1-il)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
115 1-(4-benzilpiperazin-1-il)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
116 1-(4-(4-metoksifenil)piperazin-1-il)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
117 1-(2-benzilpiperidin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
118 1-(4-(2-fluorofenil)piperazin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butan-1,4-dion;
119 1-(4-(cikloheksilmetil)piperazin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
120 N-(3-(1H-imidazol-1-il)propil)-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
121 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(3-fenil-pirolidin-1-il)butan-1,4-dion;
122 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(furan-2-karbonil)piperazin-1-il)butan-1,4-dion;
123 N-(3-(3,4-dihidrokinolin-1(2H)-il)propil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
124 2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(piperidin-1-il)butan-1,4-dion;
125 4-(4-(2-metoksifenil)piperazin-1-il)-2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
126 4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(2-(pirazin-2-il)etil)butanamid;
127 N,N-dietil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-butanamid;
128 1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(piridin-2-il)piperazin-1-il)butan-1,4-dion;
129 1-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(3-metoksifenil)piperazin-1-il)butan-1,4-dion;
130 1-(4-izopropilpiperazin-1-il)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
131 1-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(3-(trifluorometil)fenil)piperazin-1-il)butan-1,4-dion;
132 1-(4-fenilpiperazin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
133 1-(3,5-dimetilpiperidin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
134 1-(5,6-dihidropiridin-1-(2H)-il)-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
135 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(pirimidin-2-il)piperazin-1-il)butan-1,4-dion;
136 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(3-metil-piperidin-1-il)butan-1,4-dion;
137 N-etil-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(piridin-4-ilmetil)butanamid;
138 4-(4-acetilpiperazin-1-il)-2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
139 4-(2,6-dimetilmorfolino)-2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butan-1,4-dion;
140 4-(2,5-dihidro-1H-pirol-1-il)-2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
141 N-(2-metoksifenetil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
142 4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-izopentil-4-oksobutanamid;
143 N-(2,4-dimetoksibenzil)-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanamid;
144 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-((5-metilfuran-2-il)metil)-4-oksobutanamid;
145 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-pentilbutanamid;
146 1-(4-benzilpiperidin-1-il)-4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butan-1,4-dion;
147 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-metilpiperidin-1-il)butan-1,4-dion;
148 1-(azetidin-1-il)-4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
149 1-(3,4-dihidroizokinolin-2(1H)-il)-2-metil-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
150 1-(4-(benzo[d][1,3]dioksol-5-ilmetil)piperazin-1-il)-2-metil-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
151 N-benzil-N-etil-4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
152 N-metil-4-okso-N-fenetil-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
153 Etil1-(4-okso-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanoil)piperidine-4-karboksilat;
154 (E)-1-(4-(3-fenilprop-2-enil)-piperazin-1-il)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
155 1-(2-(tiazol-2-il)pirolidin-1-il)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
156 N-cikloheksil-N-etil-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
157 N-etil-N-izopropil-4-okso-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
158 1-(pirolidin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
159 1-(4-(piridin-4-il)piperazin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
160 1-(2-(piridin-2-ilmetil)pirolidin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
161 etil 1-(4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-oksobutanoil)piperidine-3-karboksilat;
162 1-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(4-(trifluorometil)fenil)piperazin-1-il)butan-1,4-dion;
163 1-(2-(5-bromopiridin-3-il)pirolidin-1-il)-4-(4-(4-fluorofenil)-6,7-dihidro-tieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
164 1-(4-etilpiperazin-1-il)-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
165 1-(2-etilpiperidin-1-il)-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
166 N,N-dibenzil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
167 N,N-diizobutil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
168 1-(3,4-dihidrokinolin-1 (2H)-il)-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
169 1-(4-(3,4-diklorobenzil)piperazin-1-il)-4-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
170 1-(4-p-tolil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(2,4,6-trimetil-benzil)piperazin-1-il)butan-1,4-dion;
171 1-(4-(4-bromobenzil)piperazin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butan-1,4-dion;
172 1-(4-(4-klorobenzil)piperazin-1-il)-4-(4-m-tolil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butan-1,4-dion;
173 1-(2-((4,6-dimetilpiridin-2-il)metil)pirolidin-1-il)-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
174 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-((6-metilpiridin-2-il)metil)pirolidin-1-il)butan-1,4-dion;
175 1-(2-((5-etilpiridin-2-il)metil)pirolidin-1-il)-4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
176 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-(6-metoksipiridin-3-il)piperidin-1-il)butan-1,4-dion;
177 4-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-metil-4-okso-N-(piridin-3-ilmetil)butanamid;
178 N-(2,2-difeniletil)-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butanamid;
179 N-(ciklopropilmetil)-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
180 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(4-metilbenzil)piperazin-1-il)butan-1,4-dion;
181 2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-(piridin-2-ilmetil)piperidin-1-il)butan-1,4-dion;
182 4-(4-(3,5-dikloropiridin-4-il)piperazin-1-il)-2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
183 1-(2-((4,6-dimetilpiridin-2-il)metil)piperidin-1-il)-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
184 N-(4-fluorobenzil)-N-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
185 1-(4-(3-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-(piridin-2-il)pirolidin-1-il)butan-1,4-dion;
186 4-(4-(4-metoksibenzil)piperazin-1-il)-2-metil-1-(4-fenil-6,7-dihidro-tieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
187 2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(3-(piridin-3-il)pirolidin-1-il)butan-1,4-dion;
188 1-(4-(2-fluorobenzil)piperazin-1-il)-4-(4-fenil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butan-1,4-dion;
189 N-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-(2-(piridin-4-il)etil)butanamid;
190 N-butil-N-etil-3-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
191 N,3-dimetil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-propilbutanamid;
192 4-((S)-2-(metoksimetil)pirolidin-1-il)-2-metil-1-(4-fenil-6,7-dihidro-tieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
193 4-(4-(5-kloro-2-metilfenil)piperazin-1-il)-2-metil-1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
194 N-(furan-2-ilmetil)-N-metil-4-okso-4-(4-fenil-6,7-dihidrotieno[3,2-c]-piridin-5(4H)-il)butanamid;
195 1-((4aR,8aS)-oktahidroizokinolin-2(1H)-il)-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
196 1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-tiomorfolinobutan-1,4-dion;
197 1-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-(piridin-3-il)-pirolidin-1-il)butan-1,4-dion;
198 N-benzil-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-izopropil-4-oksobutanamid;
199 N-benzil-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-metil-4-oksobutanamid;
200 N-(3,4-dimetoksifenetil)-4-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-N-metil-4-oksobutanamid;
201 1-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-metil-2-fenilpiperazin-1-il)butan-1,4-dion;
202 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-fenilpiperidin-1-il)butan-1,4-dion;
203 4-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-okso-N-(2-(piridin-2-il)etil)butanamid;
204 N-benzil-2-metil-4-okso-N-fenetil-4-(4-fenil-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butanamid;
205 1-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-((6-metilpiridin-2-il)metil)piperidin-1-il)butan-1,4-dion;
206 1-(4-(4-fluorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(3-metilbenzil)piperazin-1-il)butan-1,4-dion;
207 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-(piridin-4-ilmetil)piperidin-1-il)butan-1,4-dion;
208 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-((5-etilpiridin-2-il)metil)piperidin-1-il)butan-1,4-dion;
209 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(2-((3-metilpiridin-2-il)metil)piperidin-1-il)butan-1,4-dion;
210 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(3-klorofenil)piperazin-1-il)butan-1,4-dion;
211 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(2,3-dimetilfenil)piperazin-1-il)butan-1,4-dion;
212 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(3,4-dimetilfenil)piperazin-1-il)butan-1,4-dion;
213 1-(4-(4-klorofenil)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)-4-(4-(3,4-diklorofenil)piperazin-1-il)butan-1,4-dion;
214 1-(4-(4-tert-butilbenzil)piperazin-1-il)-4-(4-(4-klorofenil)-6,7-dihidro-tieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
215 1-[4-(3,5-dikloro-4-piridil)-1-piperazinil]-2-metil-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butan-1,4-dion;
216 1-[4-[(4-metoksifenil)metil]-1-piperazinil]-4-[4-(p-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]butan-1,4-dion;
217 1-[4-[(2-fluorofenil)metil]-1-piperazinil]-4-[4-(p-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]butan-1,4-dion;
218 1-(4-metil-2-fenil-1-piperazinil)-4-[4-(p-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]butan-1,4-dion;
219 1-(4-fenil-1-piperidinil)-4-[4-(p-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]butan-1,4-dion;
220 1-[4-(p-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-[2-(2-piridil)-1-pirolidinil]butan-1,4-dion;
221 1-[4-(p-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-[3-(3-piridil)-1-pirolidinil]butan-1,4-dion;
222 4-okso-4-[4-(p-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-N-[2-(2-piridil)etil]butanamid;
223 1-[4-[(4-metoksifenil)metil]-1-piperazinil]-4-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]butan-1,4-dion;
224 1-[4-[(2-fluorofenil)metil]-1-piperazinil]-4-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]butan-1,4-dion;
225 1-(4-metil-2-fenil-1-piperazinil)-4-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]butan-1,4-dion;
226 1-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-(4-fenil-1-piperidinil)butan-1,4-dion;
227 1-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-[2-(2-piridil)-1-pirolidinil]butan-1,4-dion;
228 1-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-[3-(3-piridil)-1-pirolidinil]butan-1,4-dion;
229 N-metil-4-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[2-(4-piridil)etil]butanamid;
230 1-[4-(3-fluorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-[4-[(4-metoksifenil)metil]-1-piperazinil]butan-1,4-dion;
231 1-[4-(3-fluorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-[4-[(2-fluorofenil)metil]-1-piperazinil]butan-1,4-dion;
232 4-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-(p-tolil)-butanamid;
233 N-(2,4-dimetilfenil)-4-[4-(m-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-oksobutanamid;
234 4-[4-(3-fluorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-N-(1-metil-6-indazolil)-4-oksobutanamid;
235 4-[4-(3-fluorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-(p-tolil)butanamid;
236 4-[4-(3-fluorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-fenilbutanamid;
237 N-(2-klorofenil)-4-[4-(3-fluorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-oksobutanamid;
238 N-(2,4-dimetilfenil)-4-[4-(3-fluorofenil)-6,7-dihidro-4H-tieno[3,2-c]-piridin-5-il]-4-oksobutanamid;
239 4-[4-(4-klorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-N-(1-metil-6-indazolil)-4-oksobutanamid;
240 4-[4-(4-klorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-(p-tolil)butanamid;
241 4-[4-(4-klorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-N-(4-metoksifenil)-4-oksobutanamid;
242 4-[4-(4-klorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-fenilbutanamid;
243 4-[4-(4-klorofenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-N-(2,4-dimetilfenil)-4-oksobutanamid;
244 4-[4-(2,6-dimetilfenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
245 N-(2-cikloheksiletil)-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
246 N-(3,3-dimetilbutil)-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
247 N-(cikloheksilmetil)-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
248 N-[[3-metil-5-(trifluorometoksi)fenil]metil]-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
249 N-[[4-metil-3-(trifluorometil)fenil]metil]-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
250 N-[[4-fluoro-3-(trifluorometil)fenil]metil]-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
251 4-[4-(2-etilfenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
252 4-[4-(2-izopropilfenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
253 N-(3-cikloheksilpropil)-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
254 4-[4-(3-metil-2-tienil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
255 (1 S,2S)-2-[okso-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)metil]-N-[[3-(trifluorometil)fenil]metil]-1-ciklopropankarboksamid;
256 4-[4-(o-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[2-(trifluorometil)fenil]metil]butanamid;
257 4-[4-(o-tolil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[4-(trifluorometil)fenil]metil]butanamid;
258 4-(7-butil-5,7-dihidro-4H-tieno[2,3-c]piridin-6-il)-4-okso-N-[[3-(trifluoro-metil)fenil]metil]butanamid;
259 4-[4-(cikloheksilmetil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
260 4-(4-ciklopropil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
261 4-okso-4-(4-fenetil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-N-[[3-(trifluorometil)fenil]metil]butanamid;
262 4-[4-(4-fluoro-2-metilfenil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
263 4-(4-ciklopentil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
264 N-[[2-metil-3-(trifluorometil)fenil]metil]-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
265 4-okso-4-[4-(3-fenilpropil)-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il]-N-[[3-(trifluorometil)fenil]metil]butanamid;
266 N-[[2-metil-5-(trifluorometil)fenil]metil]-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
267 N-cikloheksil-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-butanamid;
268 N-(2,2-dimetilpropil)-4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)butanamid;
269 1-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-4-[7-(trifluorometil)-3,4-dihidro-1H-izokinolin-2-il]butan-1,4-dion;
270 4-okso-N-pentil-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-butanamid;
271 1-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-4-[5-(trifluorometil)-3,4-dihidro-1H-izokinolin-2-il]butan-1,4-dion;
272 4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-N-[5-(trifluoro-metil)-1-tetralinil]butanamid;
273 4-okso-4-(4-fenil-6,7-dihidro-4H-tieno[3,2-c]piridin-5-il)-N-[7-(trifluoro-metil)-1-tetralinil]butanamid;
274 4-[7-(o-tolil)-5,7-dihidro-4H-tieno[2,3-c]piridin-6-il]-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
275 4-(7-cikloheksil-5,7-dihidro-4H-tieno[2,3-c]piridin-6-il)-4-okso-N-[[3-(trifluorometil)fenil]metil]butanamid;
ili njihove fiziološki prihvatljive soli.
12. Lijek naznačen time da sadrži barem jedan spoj prema bilo kojem od zahtjeva 1 do 11 ili spoj odabran iz skupine koja sadrži
- 1-morfolino-4-(4-(tiofen-2-il)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion,
- 1-(4-acetilpiperazin-1-il)-4-(4-(tiofen-2-il)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion, i
- 1-(3-fenil-4,5-dihidropirazol-1-il)-4-(4-(tiofen-2-il)-6,7-dihidrotieno-[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
u obliku pojedinačnog stereoizomera ili njihove smjese, slobodnog spoja i/ili njegovih fiziološki prihvatljivih soli, i pogodnih aditiva i/ili pomoćnih tvari i/ili proizvoljno dodatnih aktivnih sastojaka.
13. Uporaba spoja prema bilo kojem od zahtjeva 1 do 11 ili spoja odabranog iz skupine koja sadrži
- 1-morfolino-4-(4-(tiofen-2-il)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion,
- 1-(4-acetilpiperazin-1-il)-4-(4-(tiofen-2-il)-6,7-dihidrotieno[3,2-c]piridin-5(4H)-il)butan-1,4-dion, i
- 1-(3-fenil-4,5-dihidropirazol-1-il)-4-(4-(tiofen-2-il)-6,7-dihidrotieno-[3,2-c]piridin-5(4H)-il)butan-1,4-dion;
u obliku pojedinačnog stereoizomera ili njihove smjese, slobodnog spoja i/ili njegovih fiziološki prihvatljivih soli, naznačena time da je za dobivanje za liječenje boli, epilepsije, anksioznog poremećaja, ovisnosti, manije, bipolarnih poremećaja, migrene, kognitivnih bolesti, diskinezija povezanih sa distonijom i/ili urinarne inkontinencije.
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| EP08018617 | 2008-10-24 | ||
| PCT/EP2009/007567 WO2010046108A1 (de) | 2008-10-24 | 2009-10-22 | Substituierte 4,5,6,7-tetrahydrothienopyridine als kcnq2/3 modulatoren zur behandlung von schmerz, epilepsie und harninkontinenz |
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| US (1) | US20100105722A1 (hr) |
| EP (1) | EP2350093B1 (hr) |
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| AU (1) | AU2009306722A1 (hr) |
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| DK (1) | DK2350093T3 (hr) |
| ES (1) | ES2392758T3 (hr) |
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| TW201211007A (en) | 2010-08-27 | 2012-03-16 | Gruenenthal Gmbh | Substituted 2-amino-quinoline-3-carboxamides as KCNQ2/3 modulators |
| US8653102B2 (en) | 2010-08-27 | 2014-02-18 | Gruenenthal Gmbh | Substituted 2-oxo- and 2-thioxo-dihydroquinoline-3-carboxamides as KCNQ2/3 modulators |
| AR082734A1 (es) | 2010-08-27 | 2012-12-26 | Gruenenthal Gmbh | Quinolino-3-carboxamidas sustituidas como moduladores de kcnq2/3 |
| AU2011295405B2 (en) * | 2010-08-27 | 2015-01-22 | Grünenthal GmbH | Substituted 2-oxy-quinoline-3-carboxamides as KCNQ2/3 modulators |
| US8618129B2 (en) | 2010-09-01 | 2013-12-31 | Gruenenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators |
| US9168259B2 (en) | 2010-10-20 | 2015-10-27 | Grünenthal GmbH | Substituted 6-amino-nicotinamides as KCNQ2/3 modulators |
| MX367623B (es) | 2010-10-20 | 2019-08-29 | Gruenenthal Gmbh | 6-amino-nicotinamidas sustituidas como moduladores de kcnq2/3. |
| US9242994B2 (en) | 2012-03-23 | 2016-01-26 | Memorial Sloan-Kettering Cancer Center | Treatment of pancreatic and related cancers with 5-acyl-6,7-dihydrothieno[3,2-c]pyridines |
| JP6033403B2 (ja) | 2012-04-18 | 2016-11-30 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Ｋｃｎｑ２／３調節因子としてのｏｈ含有基を有する置換６−アミノ−ニコチンアミド類 |
| MX2014012491A (es) | 2012-04-18 | 2014-11-14 | Grünenthal GmbH | 4-aminobenzamidas sustituidas como moduladores de kcnq2/3. |
| WO2014082738A1 (en) | 2012-11-28 | 2014-06-05 | Grünenthal GmbH | Heteroquinoline-3-carboxamides as kcnq2/3 modulators |
| US9248122B2 (en) | 2012-11-28 | 2016-02-02 | Grünenthal GmbH | Heteroquinoline-3-carboxamides as KCNQ2/3 modulators |
| AU2013351550A1 (en) | 2012-11-28 | 2015-07-16 | Grünenthal GmbH | Specific carboxamides as KCNQ2/3 modulators |
| CA3180317A1 (en) | 2020-04-17 | 2021-10-21 | The Trustees Of Indiana University | Small molecule antiviral drug treatment for human papillomavirus infections |
| US11931356B1 (en) | 2022-11-30 | 2024-03-19 | The Trustees Of Indiana University | Compositions and methods for treating human papilloma virus infections |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2733750B1 (fr) * | 1995-05-03 | 1997-06-13 | Synthelabo | Derives de l'acide gamma-oxo-alpha-(phenylmethyl)-5,6- dihydro-4h-thieno(3,4-c)pyrrole-5-butanoique, leur preparation et leur application en therapeutique |
| US6855829B2 (en) * | 2001-02-20 | 2005-02-15 | Bristol-Myers Squibb Company | 3-fluoro-2-oxindole modulators of KCNQ potassium channels and use thereof in treating migraine and mechanistically related disease |
| ES2309765T3 (es) * | 2004-05-28 | 2008-12-16 | 4Sc Ag | Tetrahidropiridotiofenos. |
| US7714134B2 (en) * | 2004-06-11 | 2010-05-11 | 4Sc Ag | Compounds and use of tetrahydropyridothiophenes |
| DE102006049452A1 (de) * | 2006-10-17 | 2008-05-08 | Grünenthal GmbH | Substituierte Tetrahydropyrolopiperazin-Verbindungen und deren Verwendung in Arzneimitteln |
| WO2009001128A1 (en) * | 2007-06-26 | 2008-12-31 | Astrazeneca Ab | 1,2-cycl0hexane dicarboxamides as cathepsin inhibitors |
-
2009
- 2009-10-22 PL PL09747793T patent/PL2350093T3/pl unknown
- 2009-10-22 AU AU2009306722A patent/AU2009306722A1/en not_active Abandoned
- 2009-10-22 MX MX2011003849A patent/MX2011003849A/es active IP Right Grant
- 2009-10-22 SI SI200930353T patent/SI2350093T1/sl unknown
- 2009-10-22 EP EP09747793A patent/EP2350093B1/de not_active Not-in-force
- 2009-10-22 CA CA2739740A patent/CA2739740A1/en not_active Abandoned
- 2009-10-22 JP JP2011532538A patent/JP2012506395A/ja active Pending
- 2009-10-22 ES ES09747793T patent/ES2392758T3/es active Active
- 2009-10-22 DK DK09747793.9T patent/DK2350093T3/da active
- 2009-10-22 PT PT09747793T patent/PT2350093E/pt unknown
- 2009-10-22 WO PCT/EP2009/007567 patent/WO2010046108A1/de active Application Filing
- 2009-10-22 BR BRPI0919898A patent/BRPI0919898A2/pt not_active IP Right Cessation
- 2009-10-23 US US12/604,534 patent/US20100105722A1/en not_active Abandoned
-
2012
- 2012-10-12 HR HRP20120822AT patent/HRP20120822T1/hr unknown
- 2012-11-05 CY CY20121101053T patent/CY1113373T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2739740A1 (en) | 2010-04-29 |
| JP2012506395A (ja) | 2012-03-15 |
| BRPI0919898A2 (pt) | 2016-02-16 |
| PT2350093E (pt) | 2012-11-02 |
| ES2392758T3 (es) | 2012-12-13 |
| DK2350093T3 (da) | 2012-11-12 |
| CY1113373T1 (el) | 2016-06-22 |
| EP2350093A1 (de) | 2011-08-03 |
| WO2010046108A1 (de) | 2010-04-29 |
| PL2350093T3 (pl) | 2013-01-31 |
| US20100105722A1 (en) | 2010-04-29 |
| MX2011003849A (es) | 2011-05-23 |
| AU2009306722A1 (en) | 2010-04-29 |
| SI2350093T1 (sl) | 2012-11-30 |
| EP2350093B1 (de) | 2012-10-03 |
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