ZA200608494B - Thienopyridine derivatives - Google Patents
Thienopyridine derivatives Download PDFInfo
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- ZA200608494B ZA200608494B ZA200608494A ZA200608494A ZA200608494B ZA 200608494 B ZA200608494 B ZA 200608494B ZA 200608494 A ZA200608494 A ZA 200608494A ZA 200608494 A ZA200608494 A ZA 200608494A ZA 200608494 B ZA200608494 B ZA 200608494B
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- South Africa
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- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title description 4
- 125000001424 substituent group Chemical group 0.000 claims description 449
- 229910052717 sulfur Inorganic materials 0.000 claims description 91
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 87
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 84
- 229910052760 oxygen Inorganic materials 0.000 claims description 84
- 239000001301 oxygen Substances 0.000 claims description 84
- 239000011593 sulfur Substances 0.000 claims description 84
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 83
- -1 hydroxyimino group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 47
- 229910052792 caesium Inorganic materials 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- 208000001132 Osteoporosis Diseases 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- RXGHULSMJIVVTA-UHFFFAOYSA-N thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(=O)N)=CC2=C1 RXGHULSMJIVVTA-UHFFFAOYSA-N 0.000 claims description 8
- 208000020084 Bone disease Diseases 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 210000000988 bone and bone Anatomy 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 208000010392 Bone Fractures Diseases 0.000 claims description 4
- 206010010582 Congenital osteodystrophy Diseases 0.000 claims description 4
- 206010013883 Dwarfism Diseases 0.000 claims description 4
- 208000007652 Dysostoses Diseases 0.000 claims description 4
- 201000001324 Dysostosis Diseases 0.000 claims description 4
- 208000029725 Metabolic bone disease Diseases 0.000 claims description 4
- 208000010191 Osteitis Deformans Diseases 0.000 claims description 4
- 206010049088 Osteopenia Diseases 0.000 claims description 4
- 208000027067 Paget disease of bone Diseases 0.000 claims description 4
- 206010039984 Senile osteoporosis Diseases 0.000 claims description 4
- 208000016738 bone Paget disease Diseases 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
- 239000003018 immunosuppressive agent Substances 0.000 claims description 4
- 208000001685 postmenopausal osteoporosis Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound 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 description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- JNKYMKRVFQFIGJ-JTQLQIEISA-N 3-amino-4-[(3s)-3-(methoxymethyl)piperidin-1-yl]-6-methylthieno[2,3-b]pyridine-2-carboxamide Chemical compound C1[C@@H](COC)CCCN1C1=CC(C)=NC2=C1C(N)=C(C(N)=O)S2 JNKYMKRVFQFIGJ-JTQLQIEISA-N 0.000 claims description 2
- OOSUQPOVVGCURT-UHFFFAOYSA-N 3-amino-4-[4-(1,3-benzoxazol-6-yl)-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=12C(N)=C(C(=O)N)SC2=NC=CC=1N(CC1)CCCN1C1=CC=C(N=CO2)C2=C1 OOSUQPOVVGCURT-UHFFFAOYSA-N 0.000 claims description 2
- IZFCVZOUIBCTTN-UHFFFAOYSA-N 3-amino-4-[4-[4-(2-methoxyethyl)phenyl]-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(CCOC)=CC=C1N1CCN(C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)CCC1 IZFCVZOUIBCTTN-UHFFFAOYSA-N 0.000 claims description 2
- HSUORKSVINWKFW-UHFFFAOYSA-N 3-amino-4-[4-[4-(dimethylamino)phenyl]-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1N1CCN(C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)CCC1 HSUORKSVINWKFW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- DNSJYEBNZGXVJX-VIFPVBQESA-N 3-amino-4-[(3s)-3-(methoxymethyl)piperidin-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1[C@@H](COC)CCCN1C1=CC=NC2=C1C(N)=C(C(N)=O)S2 DNSJYEBNZGXVJX-VIFPVBQESA-N 0.000 claims 1
- GRXWTSXZWGAIIM-UHFFFAOYSA-N 3-amino-4-[3-[3-(2-hydroxyethoxy)propyl]piperidin-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=12C(N)=C(C(=O)N)SC2=NC=CC=1N1CCCC(CCCOCCO)C1 GRXWTSXZWGAIIM-UHFFFAOYSA-N 0.000 claims 1
- OHQPTPAOZCZOTP-UHFFFAOYSA-N 3-amino-4-[4-[4-[(2-methyl-1,3-dioxolan-2-yl)methyl]phenyl]-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C(N2CCN(CCC2)C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)C=CC=1CC1(C)OCCO1 OHQPTPAOZCZOTP-UHFFFAOYSA-N 0.000 claims 1
- APCNFCXTKFLNKA-UHFFFAOYSA-N 3-amino-4-[4-[4-[2-(dimethylamino)ethyl]phenyl]-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(CCN(C)C)=CC=C1N1CCN(C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)CCC1 APCNFCXTKFLNKA-UHFFFAOYSA-N 0.000 claims 1
- IEHGHPBXEDARCU-UHFFFAOYSA-N 4-[4-(4-acetyl-1,3-thiazol-2-yl)-1,4-diazepan-1-yl]-3-aminothieno[2,3-b]pyridine-2-carboxamide Chemical compound CC(=O)C1=CSC(N2CCN(CCC2)C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)=N1 IEHGHPBXEDARCU-UHFFFAOYSA-N 0.000 claims 1
- WVEXVLJAGBREQO-UHFFFAOYSA-N 4-[4-(4-acetylphenyl)-1,4-diazepan-1-yl]-3-aminothieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)CCC1 WVEXVLJAGBREQO-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- 125000004193 piperazinyl group Chemical group 0.000 description 4
- 125000005936 piperidyl group Chemical group 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 3
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 230000011164 ossification Effects 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 229940009098 aspartate Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 2
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- 150000004677 hydrates Chemical class 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
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- 125000005963 oxadiazolidinyl group Chemical group 0.000 description 2
- 125000000160 oxazolidinyl group Chemical group 0.000 description 2
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 2
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- 125000004673 propylcarbonyl group Chemical group 0.000 description 2
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
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- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 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 description 1
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- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical class CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
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- BOLRUYAQAPTJMP-UHFFFAOYSA-N 3-amino-4-[3-[3-[2-(dimethylamino)-2-oxoethoxy]propyl]piperidin-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1C(CCCOCC(=O)N(C)C)CCCN1C1=CC=NC2=C1C(N)=C(C(N)=O)S2 BOLRUYAQAPTJMP-UHFFFAOYSA-N 0.000 description 1
- LSAJFWWMIQCKFE-UHFFFAOYSA-N 3-amino-4-[4-(4-hydroxyimino-2,3-dihydrochromen-7-yl)-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=12C(N)=C(C(=O)N)SC2=NC=CC=1N(CC1)CCCN1C1=CC=C(C(CCO2)=NO)C2=C1 LSAJFWWMIQCKFE-UHFFFAOYSA-N 0.000 description 1
- YYTRWGANRPFCDX-UHFFFAOYSA-N 3-amino-4-[4-(4-propanoylphenyl)-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)CC)=CC=C1N1CCN(C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)CCC1 YYTRWGANRPFCDX-UHFFFAOYSA-N 0.000 description 1
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- NRNDSVPIURSOBZ-UHFFFAOYSA-N 3-amino-4-[4-[4-(2-hydroxyethyl)phenyl]-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=12C(N)=C(C(=O)N)SC2=NC=CC=1N(CC1)CCCN1C1=CC=C(CCO)C=C1 NRNDSVPIURSOBZ-UHFFFAOYSA-N 0.000 description 1
- LFVUENZIJDQVCA-UHFFFAOYSA-N 3-amino-4-[4-[4-(2-oxopropyl)phenyl]-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(CC(=O)C)=CC=C1N1CCN(C=2C=3C(N)=C(C(N)=O)SC=3N=CC=2)CCC1 LFVUENZIJDQVCA-UHFFFAOYSA-N 0.000 description 1
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- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000002521 alkyl halide group Chemical group 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
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- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
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- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
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- 150000002301 glucosamine derivatives Chemical class 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical compound NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-M ornithinate Chemical compound NCCCC(N)C([O-])=O AHLPHDHHMVZTML-UHFFFAOYSA-M 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
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- 150000004885 piperazines Chemical class 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 239000002175 thienopyridine Substances 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
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- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Orthopedic Medicine & Surgery (AREA)
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- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
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| JP2004116366 | 2004-04-12 |
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| ZA200608494B true ZA200608494B (en) | 2007-11-28 |
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Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20070219234A1 (fr) |
| EP (1) | EP1764367A1 (fr) |
| CN (1) | CN1968954A (fr) |
| AU (1) | AU2005233437A1 (fr) |
| BR (1) | BRPI0509795A (fr) |
| CA (1) | CA2562827A1 (fr) |
| IL (1) | IL178294A0 (fr) |
| MX (1) | MXPA06011799A (fr) |
| NO (1) | NO20065178L (fr) |
| TW (1) | TW200609237A (fr) |
| WO (1) | WO2005100365A1 (fr) |
| ZA (1) | ZA200608494B (fr) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101078098B1 (ko) | 2003-01-14 | 2011-10-28 | 아레나 파마슈티칼스, 인크. | 대사 조절제로서의 １,２,３-삼치환된 아릴 및 헤테로아릴유도체, 및 당뇨병 및 고혈당증을 비롯한 이에 관련된장애의 예방 및 치료 |
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200927731A (en) | 2007-09-14 | 2009-07-01 | Ortho Mcneil Janssen Pharm | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| PT2200985E (pt) | 2007-09-14 | 2011-07-21 | Ortho Mcneil Janssen Pharm | 4-(aril-x-fenil)-1h-piridin-2-onas 1,3-dissubstituídas |
| KR101533440B1 (ko) | 2007-09-14 | 2015-07-03 | 얀센 파마슈티칼스 인코포레이티드 | １´,３´-이치환된-４-페닐-３,４,５,６-테트라히드로-２ｈ,１´ｈ-[１,４´]비피리디닐-２´-온 |
| CN101861316B (zh) | 2007-11-14 | 2013-08-21 | 奥梅-杨森制药有限公司 | 咪唑并[1,2-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| WO2010025890A1 (fr) | 2008-09-02 | 2010-03-11 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc | Dérivés de 3-azabicyclo[3.1.0]hexyle comme modulateurs des récepteurs métabotropiques du glutamate |
| AU2009304293B2 (en) | 2008-10-16 | 2012-04-26 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| AU2009319387B2 (en) | 2008-11-28 | 2012-05-10 | Addex Pharma S.A. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| EA020671B1 (ru) | 2009-05-12 | 2014-12-30 | Янссен Фармасьютикалз, Инк. | ПРОИЗВОДНЫЕ 1,2,4-ТРИАЗОЛО[4,3-a]ПИРИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПОЛОЖИТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR2 |
| SG176021A1 (en) | 2009-05-12 | 2011-12-29 | Janssen Pharmaceuticals Inc | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| EP2270002A1 (fr) * | 2009-06-18 | 2011-01-05 | Vereniging voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patiëntenzorg | Dérivés de quinazoline comme inhibiteurs du H4-recepteur de l'histamin dans le traitement de maladies inflammatoires |
| CA2812061A1 (fr) | 2010-09-22 | 2012-03-29 | Arena Pharmaceuticals, Inc. | Modulateurs du recepteur gpr119 et traitement des troubles qui lui sont lies |
| AU2011328203B2 (en) | 2010-11-08 | 2015-03-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| PT2649069E (pt) | 2010-11-08 | 2015-11-20 | Janssen Pharmaceuticals Inc | Derivados de 1,2,4-triazolo[4,3-a]piridina e sua utilização como moduladores alostéricos positivos de recetores mglur2 |
| US9012448B2 (en) | 2010-11-08 | 2015-04-21 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| RU2475490C1 (ru) * | 2011-08-17 | 2013-02-20 | Федеральное государственное образовательное учреждение высшего профессионального образования "Кубанский государственный аграрный университет" | N-АЦИЛИРОВАННЫЕ 3-АМИНО-4,6-ДИМЕТИЛТИЕНО[2,3-b]ПИРИДИН-2-КАРБОКСАМИДЫ В КАЧЕСТВЕ АНТИДОТОВ 2,4-Д НА ПОДСОЛНЕЧНИКЕ |
| AR090037A1 (es) * | 2011-11-15 | 2014-10-15 | Xention Ltd | Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio |
| US9566310B2 (en) * | 2012-09-10 | 2017-02-14 | Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Reno | Methods of treating muscular dystrophy |
| JP2016516051A (ja) | 2013-03-15 | 2016-06-02 | ボード オブ リージェンツ オブ ザ ネヴァダ システム オブ ハイヤー エデュケーション オン ビハーフ オブ ザ ユニヴァーシティー オブ ネヴァダ リノ | 筋ジストロフィーを治療する方法 |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| EA201690089A1 (ru) | 2013-06-11 | 2017-04-28 | Латвийский Институт Органического Синтеза | ТИЕНО[2,3-b]ПИРИДИНЫ КАК МОДУЛЯТОРЫ СОСТОЯНИЯ МНОЖЕСТВЕННОЙ ЛЕКАРСТВЕННОЙ УСТОЙЧИВОСТИ |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| JP6517197B2 (ja) | 2013-10-15 | 2019-05-22 | ケース ウエスタン リザーブ ユニバーシティ | 短鎖デヒドロゲナーゼ活性を調節する組成物および方法 |
| LT3096790T (lt) | 2014-01-21 | 2019-10-10 | Janssen Pharmaceutica, N.V. | Deriniai, apimantys 2 potipio metabotropinio glutamaterginio receptoriaus teigiamus alosterinius moduliatorius arba ortosterinius agonistus, ir jų panaudojimas |
| UA128346C2 (uk) | 2014-01-21 | 2024-06-19 | Янссен Фармацевтика Нв | Комбінації, які містять позитивні алостеричні модулятори або ортостеричні агоністи метаботропного глутаматергічного рецептора 2 підтипу, та їх застосування |
| EP3242666A1 (fr) | 2015-01-06 | 2017-11-15 | Arena Pharmaceuticals, Inc. | Procédés de traitement de maladies associées au récepteur s1p1 |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| CA3002495A1 (fr) | 2015-11-03 | 2017-05-11 | Lu License Ab | Composes destines au traitement de desordres hyperproliferatifs |
| CN105418635A (zh) * | 2015-12-25 | 2016-03-23 | 上海应用技术学院 | 一种噻吩并吡啶类医药中间体的合成方法 |
| WO2017158151A1 (fr) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Dérivés de pyrimidone et leur utilisation dans le traitement, le soulagement ou la prévention d'une maladie virale |
| US11690847B2 (en) | 2016-11-30 | 2023-07-04 | Case Western Reserve University | Combinations of 15-PGDH inhibitors with corticosteroids and/or TNF inhibitors and uses thereof |
| US11718589B2 (en) | 2017-02-06 | 2023-08-08 | Case Western Reserve University | Compositions and methods of modulating short-chain dehydrogenase |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| US11014906B2 (en) | 2018-08-21 | 2021-05-25 | University Of South Carolina | Quinoline-based compounds and methods of inhibiting CDK8/19 |
| JP2022523742A (ja) * | 2019-02-01 | 2022-04-26 | ユニヴァーシティー オブ サウスカロライナ | 二環式ピリジン組成物およびがんの治療にそれを使用する方法 |
| US20220226343A1 (en) * | 2019-05-21 | 2022-07-21 | University Of South Carolina | 3-amino-4-[4-[4 (dimethylcarbamoyl) phenyl]-1,4-diazepan-1-yl]thieno[2,3-b]pyridine-2-carboxamide for use in cancer therapy and formulations comprising the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0776586A (ja) * | 1993-07-16 | 1995-03-20 | Yoshitomi Pharmaceut Ind Ltd | ピリジン化合物 |
| GB0003154D0 (en) * | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| DE60229975D1 (de) * | 2001-10-04 | 2009-01-02 | Smithkline Beecham Corp | Nf-kb-inhibitoren |
| CN100386329C (zh) * | 2002-06-06 | 2008-05-07 | 贝林格尔.英格海姆药物公司 | 取代的3-氨基-噻吩并[2,3-b]吡啶-2-羧酸酰胺化合物及其制备方法和用途 |
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2005
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- 2005-04-11 WO PCT/JP2005/007025 patent/WO2005100365A1/fr active Application Filing
- 2005-04-11 AU AU2005233437A patent/AU2005233437A1/en not_active Abandoned
- 2005-04-11 EP EP05728563A patent/EP1764367A1/fr not_active Withdrawn
- 2005-04-11 CN CNA2005800192903A patent/CN1968954A/zh active Pending
- 2005-04-11 US US11/578,492 patent/US20070219234A1/en not_active Abandoned
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- 2006-10-11 ZA ZA200608494A patent/ZA200608494B/en unknown
- 2006-11-10 NO NO20065178A patent/NO20065178L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20070219234A1 (en) | 2007-09-20 |
| WO2005100365A1 (fr) | 2005-10-27 |
| CN1968954A (zh) | 2007-05-23 |
| MXPA06011799A (es) | 2006-12-15 |
| CA2562827A1 (fr) | 2005-10-27 |
| EP1764367A1 (fr) | 2007-03-21 |
| NO20065178L (no) | 2007-01-12 |
| IL178294A0 (en) | 2007-02-11 |
| AU2005233437A1 (en) | 2005-10-27 |
| TW200609237A (en) | 2006-03-16 |
| BRPI0509795A (pt) | 2007-10-23 |
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