JP5476307B2 - トロパン化合物 - Google Patents
トロパン化合物 Download PDFInfo
- Publication number
- JP5476307B2 JP5476307B2 JP2010531069A JP2010531069A JP5476307B2 JP 5476307 B2 JP5476307 B2 JP 5476307B2 JP 2010531069 A JP2010531069 A JP 2010531069A JP 2010531069 A JP2010531069 A JP 2010531069A JP 5476307 B2 JP5476307 B2 JP 5476307B2
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- heterocycloalkyl
- amino
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- -1 Tropane compound Chemical class 0.000 title claims description 748
- 229930004006 tropane Natural products 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 285
- 125000000217 alkyl group Chemical group 0.000 claims description 310
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 221
- 229910052736 halogen Inorganic materials 0.000 claims description 206
- 150000002367 halogens Chemical group 0.000 claims description 198
- 150000003839 salts Chemical class 0.000 claims description 150
- 125000003545 alkoxy group Chemical group 0.000 claims description 125
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 117
- 125000003118 aryl group Chemical group 0.000 claims description 109
- 229910052739 hydrogen Inorganic materials 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 99
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
- 125000001072 heteroaryl group Chemical group 0.000 claims description 78
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 54
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 51
- 125000005843 halogen group Chemical group 0.000 claims description 48
- 125000000304 alkynyl group Chemical group 0.000 claims description 46
- 125000003282 alkyl amino group Chemical group 0.000 claims description 42
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000003386 piperidinyl group Chemical group 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 34
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 33
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 28
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 24
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 24
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 24
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 24
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 24
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 16
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical group N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000002393 azetidinyl group Chemical group 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 6
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000006187 pill Substances 0.000 claims description 6
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 5
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 5
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005059 halophenyl group Chemical group 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 5
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- HJFONKSERLWIGE-DEOSSOPVSA-N (2s)-2-[[4-[4-(1-benzofuran-2-carbonylamino)phenyl]phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC2=CC=CC=C2O1 HJFONKSERLWIGE-DEOSSOPVSA-N 0.000 claims description 2
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-SFIIULIVSA-N 1H-benzimidazole Chemical group C1=CC=C2N[11CH]=NC2=C1 HYZJCKYKOHLVJF-SFIIULIVSA-N 0.000 claims description 2
- 235000010357 aspartame Nutrition 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 251
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 16
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 232
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- 239000011570 nicotinamide Substances 0.000 description 123
- 238000005481 NMR spectroscopy Methods 0.000 description 106
- 101710113864 Heat shock protein 90 Proteins 0.000 description 101
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 54
- 238000002360 preparation method Methods 0.000 description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
- 201000010099 disease Diseases 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 210000004027 cell Anatomy 0.000 description 30
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 30
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 30
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- 102000013498 tau Proteins Human genes 0.000 description 20
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- 229940079593 drug Drugs 0.000 description 17
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
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- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 14
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Landscapes
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| EP2231666B1 (en) * | 2007-12-12 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
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