ZA200406681B - Indolamid derivatives which possess glycogen phosphory-lase inhibitory activity. - Google Patents
Indolamid derivatives which possess glycogen phosphory-lase inhibitory activity. Download PDFInfo
- Publication number
- ZA200406681B ZA200406681B ZA200406681A ZA200406681A ZA200406681B ZA 200406681 B ZA200406681 B ZA 200406681B ZA 200406681 A ZA200406681 A ZA 200406681A ZA 200406681 A ZA200406681 A ZA 200406681A ZA 200406681 B ZA200406681 B ZA 200406681B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- amino
- inden
- dihydro
- carboxamide
- Prior art date
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- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title claims description 3
- 108010046163 Glycogen Phosphorylase Proteins 0.000 title description 13
- 102000007390 Glycogen Phosphorylase Human genes 0.000 title description 13
- 230000002401 inhibitory effect Effects 0.000 title description 4
- -1 nitro, cyano, hydroxy, carboxy, carbamoyl Chemical group 0.000 claims description 200
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
- 238000001727 in vivo Methods 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 241001465754 Metazoa Species 0.000 claims description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 11
- 239000000651 prodrug Substances 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 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
- 239000002253 acid Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- 230000035879 hyperinsulinaemia Effects 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- 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
- 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 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
- 125000004433 nitrogen atom Chemical group N* 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 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
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 13
- 239000000126 substance Substances 0.000 claims 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- LXUAJVRETINVKU-AUSIDOKSSA-N 2-[(2-acetyloxyacetyl)-[(1r,2r)-2-[(5-chloro-1h-indole-2-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]amino]acetic acid Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)N(CC(O)=O)C(=O)COC(=O)C)=CC2=C1 LXUAJVRETINVKU-AUSIDOKSSA-N 0.000 claims 1
- MKQSLJDUMLAZBI-WIYYLYMNSA-N 2-[acetyl-[(1r,2r)-2-[(5-chloro-1h-indole-2-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]amino]acetic acid Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)N(CC(O)=O)C(=O)C)=CC2=C1 MKQSLJDUMLAZBI-WIYYLYMNSA-N 0.000 claims 1
- NVDONUFKLGPCPY-OXQOHEQNSA-N 3-[[(1r,2r)-2-[(5-chloro-1h-indole-2-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]amino]-3-oxopropanoic acid Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NC(=O)CC(=O)O)=CC2=C1 NVDONUFKLGPCPY-OXQOHEQNSA-N 0.000 claims 1
- YNMZCHKIBOSEJT-UHFFFAOYSA-N 5-chloro-n-(1-hydroxy-2,3-dihydro-1h-inden-2-yl)-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)NC3C(C4=CC=CC=C4C3)O)=CC2=C1 YNMZCHKIBOSEJT-UHFFFAOYSA-N 0.000 claims 1
- HBKOPLCNMIDRLT-SJLPKXTDSA-N 5-chloro-n-[(1r,2r)-1-(chloromethylsulfonylamino)-2,3-dihydro-1h-inden-2-yl]-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NS(=O)(=O)CCl)=CC2=C1 HBKOPLCNMIDRLT-SJLPKXTDSA-N 0.000 claims 1
- BIPSCXDZXGEOSO-VQIMIIECSA-N 5-chloro-n-[(1r,2r)-1-[(2-hydroxyacetyl)amino]-2,3-dihydro-1h-inden-2-yl]-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NC(=O)CO)=CC2=C1 BIPSCXDZXGEOSO-VQIMIIECSA-N 0.000 claims 1
- WGFSURNLWRIMHP-XFQXTVEOSA-N 5-chloro-n-[(1r,2r)-1-[[(2r)-2,3-dihydroxypropyl]amino]-2,3-dihydro-1h-inden-2-yl]-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NC[C@@H](O)CO)=CC2=C1 WGFSURNLWRIMHP-XFQXTVEOSA-N 0.000 claims 1
- MLIDMWHBNBSZNH-WMZOPIPTSA-N 5-chloro-n-[(1s,2s)-1-(methanesulfonamido)-2,3-dihydro-1h-inden-2-yl]-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@@H]3[C@H](C4=CC=CC=C4C3)NS(=O)(=O)C)=CC2=C1 MLIDMWHBNBSZNH-WMZOPIPTSA-N 0.000 claims 1
- BIPSCXDZXGEOSO-UHFFFAOYSA-N 5-chloro-n-[1-[(2-hydroxyacetyl)amino]-2,3-dihydro-1h-inden-2-yl]-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)NC3C(C4=CC=CC=C4C3)NC(=O)CO)=CC2=C1 BIPSCXDZXGEOSO-UHFFFAOYSA-N 0.000 claims 1
- 101100271014 Bacillus subtilis (strain 168) asnO gene Proteins 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000001441 L-beta-aspartyl group Chemical group N[C@@H](CC(=O)*)C(=O)O 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- NRPWGGSTSPLLSR-OXQOHEQNSA-N n'-[(1r,2r)-2-[(5-chloro-1h-indole-2-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]propanediamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NC(=O)CC(=O)N)=CC2=C1 NRPWGGSTSPLLSR-OXQOHEQNSA-N 0.000 claims 1
- KRGWKLDENZAJQV-VQIMIIECSA-N n-[(1r,2r)-1-[(2-amino-2-oxoethyl)amino]-2,3-dihydro-1h-inden-2-yl]-5-chloro-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NCC(=O)N)=CC2=C1 KRGWKLDENZAJQV-VQIMIIECSA-N 0.000 claims 1
- JDOKJNYMSOZCCU-VQIMIIECSA-N n-[(1r,2r)-1-[(2-aminoacetyl)amino]-2,3-dihydro-1h-inden-2-yl]-5-chloro-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NC(=O)CN)=CC2=C1 JDOKJNYMSOZCCU-VQIMIIECSA-N 0.000 claims 1
- NDQIKJHJDPHJOK-LEAFIULHSA-N n-[(1r,2r)-1-[[2-[benzyl(2-hydroxyethyl)amino]acetyl]amino]-2,3-dihydro-1h-inden-2-yl]-5-chloro-1h-indole-2-carboxamide Chemical compound N([C@@H]1C2=CC=CC=C2C[C@H]1NC(=O)C=1NC2=CC=C(Cl)C=C2C=1)C(=O)CN(CCO)CC1=CC=CC=C1 NDQIKJHJDPHJOK-LEAFIULHSA-N 0.000 claims 1
- IOCKQBSKBZZXNT-WIYYLYMNSA-N n-[(1r,2r)-1-[acetyl-(2-amino-2-oxoethyl)amino]-2,3-dihydro-1h-inden-2-yl]-5-chloro-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)N(CC(N)=O)C(=O)C)=CC2=C1 IOCKQBSKBZZXNT-WIYYLYMNSA-N 0.000 claims 1
- FZGVLIXOSYASKL-IEBWSBKVSA-N n-[(1r,2r)-1-acetamido-2,3-dihydro-1h-inden-2-yl]-5-chloro-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NC(=O)C)=CC2=C1 FZGVLIXOSYASKL-IEBWSBKVSA-N 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- ZYLSROLEEIUXMB-HIAQKOENSA-N tert-butyl n-[1-[[(1r,2r)-2-[(5-chloro-1h-indole-2-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]amino]-1,4-dioxopentan-3-yl]carbamate Chemical compound ClC1=CC=C2NC(C(=O)N[C@H]3[C@@H](C4=CC=CC=C4C3)NC(=O)CC(C(=O)C)NC(=O)OC(C)(C)C)=CC2=C1 ZYLSROLEEIUXMB-HIAQKOENSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000005958 tetrahydrothienyl 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
- 230000000694 effects Effects 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 210000004185 liver Anatomy 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 230000004116 glycogenolysis Effects 0.000 description 3
- 230000002440 hepatic effect Effects 0.000 description 3
- 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011575 calcium Substances 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- HBZHNVUMFPGVHW-UHFFFAOYSA-N 2-chloro-1h-indole Chemical compound C1=CC=C2NC(Cl)=CC2=C1 HBZHNVUMFPGVHW-UHFFFAOYSA-N 0.000 description 1
- ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
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|---|---|---|---|
| GBGB0205176.1A GB0205176D0 (en) | 2002-03-06 | 2002-03-06 | Chemical compounds |
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| ZA200406681B true ZA200406681B (en) | 2005-09-22 |
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| EP (1) | EP1483240A1 (is) |
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| AU (1) | AU2003216988A1 (is) |
| BR (1) | BR0308144A (is) |
| CA (1) | CA2477717A1 (is) |
| GB (1) | GB0205176D0 (is) |
| IL (1) | IL163823A0 (is) |
| IS (1) | IS7435A (is) |
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| TW (1) | TW200304817A (is) |
| WO (1) | WO2003074484A1 (is) |
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| GB0205162D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
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| GB0205166D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0222912D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0222909D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| JP2006507294A (ja) | 2002-11-07 | 2006-03-02 | ファイザー・プロダクツ・インク | 抗糖尿病剤 |
| GB0318464D0 (en) * | 2003-08-07 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
| GB0319690D0 (en) * | 2003-08-22 | 2003-09-24 | Astrazeneca Ab | Chemical compounds |
| WO2005020985A1 (en) * | 2003-08-29 | 2005-03-10 | Astrazeneca Ab | Indolamide derivatives which possess glycogen phosphorylase inhibitory activity |
| US7365061B2 (en) | 2004-11-15 | 2008-04-29 | Bristol-Myers Squibb Company | 2-Amino-3-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| US7214704B2 (en) | 2004-11-15 | 2007-05-08 | Bristol-Myers Squibb Company | 2-Amino-1-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| WO2006055462A1 (en) * | 2004-11-15 | 2006-05-26 | Bristol-Myers Squibb Company | 2-amino-4-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 |
| US20090124682A1 (en) * | 2005-02-05 | 2009-05-14 | Alan Martin Birch | Indan-Amide Derivatives with Glycogen Phosphorylase Inhibitory Activity |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| SG10201901192TA (en) * | 2014-09-10 | 2019-03-28 | Epizyme Inc | Smyd inhibitors |
| 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 |
| CN114403150B (zh) * | 2022-02-09 | 2022-11-04 | 中国农业大学 | 一种吲哚酰胺类化合物作为海藻糖-6-磷酸合成酶抑制剂的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3706810A (en) * | 1970-09-15 | 1972-12-19 | American Cyanamid Co | N-morpholinoalkyl-thieno(3,2-b)pyrrole-5-carboxamides |
| DE3304019A1 (de) | 1983-02-07 | 1984-08-09 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 3-acyloxy-1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4668769A (en) * | 1985-08-02 | 1987-05-26 | Hoover Dennis J | Oxa- and azahomocyclostatine polypeptides |
| 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 |
| GB8522574D0 (en) * | 1985-09-12 | 1985-10-16 | Lepetit Spa | Amides of teicoplanin compounds |
| 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 |
| US4791112A (en) * | 1987-02-02 | 1988-12-13 | The Boc Group, Inc. | N-heterocyclic-N-(4-piperidyl)amides and pharmaceutical compositions and methods employing such compounds |
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-
2002
- 2002-03-06 GB GBGB0205176.1A patent/GB0205176D0/en not_active Ceased
-
2003
- 2003-03-04 AU AU2003216988A patent/AU2003216988A1/en not_active Abandoned
- 2003-03-04 US US10/506,554 patent/US7138415B2/en not_active Expired - Fee Related
- 2003-03-04 PL PL03373872A patent/PL373872A1/xx not_active Application Discontinuation
- 2003-03-04 JP JP2003572954A patent/JP2005524667A/ja not_active Withdrawn
- 2003-03-04 KR KR10-2004-7013859A patent/KR20040097145A/ko not_active Application Discontinuation
- 2003-03-04 EP EP03712310A patent/EP1483240A1/en not_active Withdrawn
- 2003-03-04 NZ NZ534683A patent/NZ534683A/en unknown
- 2003-03-04 CA CA002477717A patent/CA2477717A1/en not_active Abandoned
- 2003-03-04 WO PCT/GB2003/000883 patent/WO2003074484A1/en active Application Filing
- 2003-03-04 RU RU2004125182/04A patent/RU2004125182A/ru not_active Application Discontinuation
- 2003-03-04 IL IL16382303A patent/IL163823A0/xx unknown
- 2003-03-04 MX MXPA04008612A patent/MXPA04008612A/es active IP Right Grant
- 2003-03-04 BR BR0308144-3A patent/BR0308144A/pt not_active IP Right Cessation
- 2003-03-04 CN CNB038053098A patent/CN100374420C/zh not_active Expired - Fee Related
- 2003-03-05 TW TW092104668A patent/TW200304817A/zh unknown
- 2003-03-06 AR ARP030100769A patent/AR038889A1/es unknown
-
2004
- 2004-08-23 ZA ZA200406681A patent/ZA200406681B/en unknown
- 2004-09-02 IS IS7435A patent/IS7435A/is unknown
- 2004-09-24 NO NO20044032A patent/NO20044032L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB0205176D0 (en) | 2002-04-17 |
| JP2005524667A (ja) | 2005-08-18 |
| IL163823A0 (en) | 2005-12-18 |
| US7138415B2 (en) | 2006-11-21 |
| EP1483240A1 (en) | 2004-12-08 |
| PL373872A1 (en) | 2005-09-19 |
| AU2003216988A1 (en) | 2003-09-16 |
| US20050107362A1 (en) | 2005-05-19 |
| RU2004125182A (ru) | 2005-06-10 |
| CN100374420C (zh) | 2008-03-12 |
| CA2477717A1 (en) | 2003-09-12 |
| NO20044032L (no) | 2004-10-05 |
| CN1639120A (zh) | 2005-07-13 |
| NZ534683A (en) | 2006-02-24 |
| KR20040097145A (ko) | 2004-11-17 |
| TW200304817A (en) | 2003-10-16 |
| IS7435A (is) | 2004-09-02 |
| WO2003074484A1 (en) | 2003-09-12 |
| BR0308144A (pt) | 2004-12-07 |
| MXPA04008612A (es) | 2004-12-06 |
| AR038889A1 (es) | 2005-02-02 |
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