ZA200406679B - Heterocyclic amide derivatives as inhibitors of glycogen phosphorylase. - Google Patents
Heterocyclic amide derivatives as inhibitors of glycogen phosphorylase. Download PDFInfo
- Publication number
- ZA200406679B ZA200406679B ZA200406679A ZA200406679A ZA200406679B ZA 200406679 B ZA200406679 B ZA 200406679B ZA 200406679 A ZA200406679 A ZA 200406679A ZA 200406679 A ZA200406679 A ZA 200406679A ZA 200406679 B ZA200406679 B ZA 200406679B
- Authority
- ZA
- South Africa
- Prior art keywords
- thieno
- carboxamide
- chloro
- tetrahydroquinolin
- pyrrole
- Prior art date
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- -1 Heterocyclic amide Chemical class 0.000 title claims description 231
- 108010046163 Glycogen Phosphorylase Proteins 0.000 title description 13
- 102000007390 Glycogen Phosphorylase Human genes 0.000 title description 13
- 239000003112 inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 44
- 150000002148 esters Chemical class 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 238000001727 in vivo Methods 0.000 claims description 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 229940002612 prodrug Drugs 0.000 claims description 11
- 239000000651 prodrug Substances 0.000 claims description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 5
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 206010051161 Hyperglucagonaemia Diseases 0.000 claims description 4
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 230000035879 hyperinsulinaemia Effects 0.000 claims description 4
- 208000031225 myocardial ischemia Diseases 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 7
- 239000000126 substance Substances 0.000 claims 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims 2
- JCZPOYAMKJFOLA-UHFFFAOYSA-N pyrrolidine-3,4-diol Chemical compound OC1CNCC1O JCZPOYAMKJFOLA-UHFFFAOYSA-N 0.000 claims 2
- LQDLDRYJCVZYKX-UHFFFAOYSA-N 2,3-dichloro-n-[1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-3,4-dihydroquinolin-3-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2N(CC(CO)CO)C(=O)C(NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 LQDLDRYJCVZYKX-UHFFFAOYSA-N 0.000 claims 1
- IJTLZFBLUNVMEM-UHFFFAOYSA-N 2-chloro-n-[1-(2-methylsulfanylethyl)-2-oxo-3,4-dihydroquinolin-3-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2N(CCSC)C(=O)C(NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 IJTLZFBLUNVMEM-UHFFFAOYSA-N 0.000 claims 1
- MPSSPROHBINMSR-UHFFFAOYSA-N 2-chloro-n-[1-(3-hydroxypropyl)-2-oxo-3,4-dihydroquinolin-3-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2N(CCCO)C(=O)C(NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 MPSSPROHBINMSR-UHFFFAOYSA-N 0.000 claims 1
- FVZYCTNHRXFRJG-UHFFFAOYSA-N 2-chloro-n-[1-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-2-oxo-3,4-dihydroquinolin-3-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound CC1=NOC(CN2C3=CC=CC=C3CC(C2=O)NC(=O)C=2NC=3SC(Cl)=CC=3C=2)=N1 FVZYCTNHRXFRJG-UHFFFAOYSA-N 0.000 claims 1
- HEXMHSAEGLWGCJ-UHFFFAOYSA-N 2-chloro-n-[1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-2-oxo-3,4-dihydroquinolin-3-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1CC(O)CCN1C(=O)CN1C2=CC=CC=C2CC(NC(=O)C=2NC=3SC(Cl)=CC=3C=2)C1=O HEXMHSAEGLWGCJ-UHFFFAOYSA-N 0.000 claims 1
- OWYSKDBZVGPFCE-UHFFFAOYSA-N 2-chloro-n-[1-[3-(methylamino)-3-oxopropyl]-2-oxo-3,4-dihydroquinolin-3-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2N(CCC(=O)NC)C(=O)C(NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 OWYSKDBZVGPFCE-UHFFFAOYSA-N 0.000 claims 1
- YUYUULPQRYMAKE-UHFFFAOYSA-N 2-chloro-n-[1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-3,4-dihydroquinolin-3-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2N(CC(CO)CO)C(=O)C(NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 YUYUULPQRYMAKE-UHFFFAOYSA-N 0.000 claims 1
- WWPPXDOOKMWVDN-UHFFFAOYSA-N 3-amino-3,4-dihydro-1h-1,5-naphthyridin-2-one Chemical compound C1=CC=C2NC(=O)C(N)CC2=N1 WWPPXDOOKMWVDN-UHFFFAOYSA-N 0.000 claims 1
- PYYUJUCEYQOLPL-UHFFFAOYSA-N 3-amino-3,4-dihydro-1h-1,7-naphthyridin-2-one Chemical compound C1=NC=C2NC(=O)C(N)CC2=C1 PYYUJUCEYQOLPL-UHFFFAOYSA-N 0.000 claims 1
- UWCXAOBUHXRFEM-UHFFFAOYSA-N 4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound S1C=CC2=C1C=C(C(=O)N)N2 UWCXAOBUHXRFEM-UHFFFAOYSA-N 0.000 claims 1
- PMYBAQWPHWQXPT-UHFFFAOYSA-N 6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CSC2=C1C=C(C(=O)N)N2 PMYBAQWPHWQXPT-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- YKTUIVKCXQYREL-UHFFFAOYSA-N n-(6-fluoro-1,2,3,4-tetrahydroquinolin-3-yl)-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1C2=CC(F)=CC=C2NCC1NC(=O)C(N1)=CC2=C1SC=C2 YKTUIVKCXQYREL-UHFFFAOYSA-N 0.000 claims 1
- JQOQXHPPXAAARB-UHFFFAOYSA-N n-(6-methoxy-1,2,3,4-tetrahydroquinolin-3-yl)-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1C2=CC(OC)=CC=C2NCC1NC(=O)C(N1)=CC2=C1SC=C2 JQOQXHPPXAAARB-UHFFFAOYSA-N 0.000 claims 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- 102000051325 Glucagon Human genes 0.000 description 4
- 108060003199 Glucagon Proteins 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 4
- 229960004666 glucagon Drugs 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 230000004116 glycogenolysis Effects 0.000 description 3
- 230000002440 hepatic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 239000005864 Sulphur Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
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- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 210000003494 hepatocyte Anatomy 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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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- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
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- 125000005565 oxadiazolylene group Chemical group 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
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| GBGB0205165.4A GB0205165D0 (en) | 2002-03-06 | 2002-03-06 | Chemical compounds |
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| ZA200406679B true ZA200406679B (en) | 2005-01-18 |
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| AR (1) | AR038888A1 (ko) |
| AU (1) | AU2003214377A1 (ko) |
| BR (1) | BR0308146A (ko) |
| CA (1) | CA2477667A1 (ko) |
| GB (1) | GB0205165D0 (ko) |
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| MX (1) | MXPA04008614A (ko) |
| NO (1) | NO20043852L (ko) |
| NZ (1) | NZ534990A (ko) |
| PL (1) | PL372973A1 (ko) |
| TW (1) | TW200305412A (ko) |
| WO (1) | WO2003074532A1 (ko) |
| ZA (1) | ZA200406679B (ko) |
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| GB0205166D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| MXPA05002303A (es) * | 2002-08-29 | 2005-06-08 | Merck & Co Inc | Indoles con actividad antidiabetica. |
| GB0222909D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0222912D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0320422D0 (en) * | 2003-08-30 | 2003-10-01 | Astrazeneca Ab | Chemical compounds |
| CZ2006427A3 (cs) | 2003-12-29 | 2006-11-15 | Sepracor Inc. | Pyrrolové a pyrazolové inhibitory DAAO |
| US7498341B2 (en) * | 2004-01-31 | 2009-03-03 | Sanofi Aventis Deutschland Gmbh | Heterocyclically substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| EP1713803B1 (de) * | 2004-01-31 | 2009-08-05 | Sanofi-Aventis Deutschland GmbH | 7-phenylamino-4-chinolon-3-carbonsäure-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US7470706B2 (en) | 2004-01-31 | 2008-12-30 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl-substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| US7402674B2 (en) | 2004-01-31 | 2008-07-22 | Sanofi-Aventis Deutschland Gmbh, | 7-Phenylamino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| DE102004004971B3 (de) * | 2004-01-31 | 2005-09-15 | Aventis Pharma Deutschland Gmbh | Cycloalkyl substituierte 7-Amino-4-chinolon-3-carbonsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arnzeimittel |
| US7226942B2 (en) | 2004-11-15 | 2007-06-05 | Bristol-Myers Squibb Company | 2-amino-4-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| WO2006053274A2 (en) | 2004-11-15 | 2006-05-18 | Bristol-Myers Squibb Company | 2-amino-1-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| US7365061B2 (en) | 2004-11-15 | 2008-04-29 | Bristol-Myers Squibb Company | 2-Amino-3-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| WO2006055435A1 (en) | 2004-11-15 | 2006-05-26 | Bristol-Myers Squibb Company | 2-aminonaphthalene derivatives and related glycogen phosphorylase inhibitors |
| US7314882B2 (en) | 2005-01-12 | 2008-01-01 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid receptor modulators |
| DE102005063244A1 (de) * | 2005-12-21 | 2007-06-28 | Eberhard-Karls-Universität Tübingen | Modifiziertes 2-Nitroimidazol-Derivat |
| ES2566479T3 (es) | 2006-01-06 | 2016-04-13 | Sunovion Pharmaceuticals Inc. | Inhibidores de reabsorción de monoamina con base en tetralona |
| US20070203111A1 (en) | 2006-01-06 | 2007-08-30 | Sepracor Inc. | Cycloalkylamines as monoamine reuptake inhibitors |
| US20090312559A1 (en) * | 2006-01-10 | 2009-12-17 | Hoveyda Amir H | Catalytic enantioselective silylations of substrates |
| EP2816024B8 (en) | 2006-03-31 | 2018-04-04 | Sunovion Pharmaceuticals Inc. | Chiral amines |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7902252B2 (en) | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| JP5420534B2 (ja) | 2007-05-31 | 2014-02-19 | サノビオン ファーマシューティカルズ インク | モノアミン再取り込み阻害薬としてのフェニル置換シクロアルキルアミン |
| KR20180051676A (ko) | 2009-10-16 | 2018-05-16 | 멜린타 테라퓨틱스, 인크. | 항미생물성 화합물 및 이의 제조 방법 및 사용 방법 |
| CN108456211A (zh) * | 2009-10-16 | 2018-08-28 | 梅琳塔治疗公司 | 抗微生物化合物和其制备和使用方法 |
| EP3268370A4 (en) | 2015-03-11 | 2018-08-22 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| CN109553580B (zh) * | 2017-09-25 | 2023-08-11 | 南京长澳医药科技有限公司 | 硝基咪唑类化合物中间体及其盐的制备方法 |
| CN112442022B (zh) * | 2019-09-02 | 2022-05-20 | 承德医学院 | 苯并嗪-4-酮类化合物、其制备方法及医药用途 |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
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| DE200740C (ko) | ||||
| US3706810A (en) | 1970-09-15 | 1972-12-19 | American Cyanamid Co | N-morpholinoalkyl-thieno(3,2-b)pyrrole-5-carboxamides |
| US4692522A (en) | 1985-04-01 | 1987-09-08 | Merck & Co., Inc. | Benzofused lactams useful as cholecystokinin antagonists |
| US4720503A (en) | 1985-08-02 | 1988-01-19 | Merck & Co., Inc. | N-substituted fused-heterocyclic carboxamide derivatives as dual cyclooxygenase and lipoxygenase inhibitors |
| US4599198A (en) | 1985-08-02 | 1986-07-08 | Pfizer Inc. | Intermediates in polypeptide synthesis |
| US4668769A (en) | 1985-08-02 | 1987-05-26 | Hoover Dennis J | Oxa- and azahomocyclostatine polypeptides |
| FR2601368B1 (fr) | 1986-07-08 | 1989-04-07 | Synthelabo | Derives de nitrofuranne, leur preparation et leur application en therapeutique. |
| DE3629545A1 (de) | 1986-08-30 | 1988-03-10 | Bayer Ag | Dihydropyridinverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| US4751231A (en) | 1987-09-16 | 1988-06-14 | Merck & Co., Inc. | Substituted thieno[2,3-b]pyrrole-5-sulfonamides as antiglaucoma agents |
| JPH02124756A (ja) | 1988-07-27 | 1990-05-14 | Suzuki Sangyo Kk | セメンティング組成物 |
| JPH04179949A (ja) | 1990-11-15 | 1992-06-26 | Fuji Photo Film Co Ltd | 新規な色素形成カプラーおよび該カプラーを用いたハロゲン化銀カラー写真感光材料 |
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-
2002
- 2002-03-06 GB GBGB0205165.4A patent/GB0205165D0/en not_active Ceased
-
2003
- 2003-03-04 KR KR10-2004-7013863A patent/KR20040096661A/ko not_active Application Discontinuation
- 2003-03-04 WO PCT/GB2003/000877 patent/WO2003074532A1/en active Application Filing
- 2003-03-04 CA CA002477667A patent/CA2477667A1/en not_active Abandoned
- 2003-03-04 BR BR0308146-0A patent/BR0308146A/pt not_active IP Right Cessation
- 2003-03-04 PL PL03372973A patent/PL372973A1/xx not_active Application Discontinuation
- 2003-03-04 MX MXPA04008614A patent/MXPA04008614A/es active IP Right Grant
- 2003-03-04 US US10/506,741 patent/US7129249B2/en not_active Expired - Fee Related
- 2003-03-04 JP JP2003573000A patent/JP2005526058A/ja not_active Withdrawn
- 2003-03-04 NZ NZ534990A patent/NZ534990A/en unknown
- 2003-03-04 AU AU2003214377A patent/AU2003214377A1/en not_active Abandoned
- 2003-03-04 CN CNB038102145A patent/CN100384852C/zh not_active Expired - Fee Related
- 2003-03-04 IL IL16380303A patent/IL163803A0/xx unknown
- 2003-03-04 EP EP03709947A patent/EP1483270A1/en not_active Withdrawn
- 2003-03-05 TW TW092104650A patent/TW200305412A/zh unknown
- 2003-03-06 AR ARP030100768A patent/AR038888A1/es unknown
-
2004
- 2004-08-23 ZA ZA200406679A patent/ZA200406679B/en unknown
- 2004-09-14 NO NO20043852A patent/NO20043852L/no not_active Application Discontinuation
-
2006
- 2006-08-08 US US11/463,144 patent/US7276517B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL372973A1 (en) | 2005-08-08 |
| GB0205165D0 (en) | 2002-04-17 |
| CA2477667A1 (en) | 2003-09-12 |
| US7129249B2 (en) | 2006-10-31 |
| US7276517B2 (en) | 2007-10-02 |
| KR20040096661A (ko) | 2004-11-16 |
| CN1653070A (zh) | 2005-08-10 |
| IL163803A0 (en) | 2005-12-18 |
| MXPA04008614A (es) | 2004-12-06 |
| EP1483270A1 (en) | 2004-12-08 |
| JP2005526058A (ja) | 2005-09-02 |
| US20070043069A1 (en) | 2007-02-22 |
| BR0308146A (pt) | 2004-12-07 |
| TW200305412A (en) | 2003-11-01 |
| AU2003214377A1 (en) | 2003-09-16 |
| CN100384852C (zh) | 2008-04-30 |
| US20050131015A1 (en) | 2005-06-16 |
| WO2003074532A1 (en) | 2003-09-12 |
| NZ534990A (en) | 2006-02-24 |
| NO20043852L (no) | 2004-09-14 |
| AR038888A1 (es) | 2005-02-02 |
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