JP2010531311A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010531311A5 JP2010531311A5 JP2010513708A JP2010513708A JP2010531311A5 JP 2010531311 A5 JP2010531311 A5 JP 2010531311A5 JP 2010513708 A JP2010513708 A JP 2010513708A JP 2010513708 A JP2010513708 A JP 2010513708A JP 2010531311 A5 JP2010531311 A5 JP 2010531311A5
- Authority
- JP
- Japan
- Prior art keywords
- unsubstituted
- indazole
- independently
- phenyl
- benzyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 13
- -1 phenyloxy- Chemical class 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229910052760 oxygen Chemical group 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 229910052723 transition metal Inorganic materials 0.000 claims 3
- 150000003624 transition metals Chemical class 0.000 claims 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 claims 1
- RUEJSAPLXFHPMR-UHFFFAOYSA-N 2-phenyl-3-(pyridin-2-ylmethyl)indazole Chemical compound C=1C=CC=NC=1CC(=C1C=CC=CC1=N1)N1C1=CC=CC=C1 RUEJSAPLXFHPMR-UHFFFAOYSA-N 0.000 claims 1
- KEWFDPAZUODCMS-UHFFFAOYSA-N 2-phenyl-3-[[4-(trifluoromethyl)phenyl]methyl]indazole Chemical compound C1=CC(C(F)(F)F)=CC=C1CC1=C2C=CC=CC2=NN1C1=CC=CC=C1 KEWFDPAZUODCMS-UHFFFAOYSA-N 0.000 claims 1
- SRUKMACJNHJLKC-UHFFFAOYSA-N 3-(2,2-diethoxyethyl)-2-phenylindazole Chemical compound N1=C2C=CC=CC2=C(CC(OCC)OCC)N1C1=CC=CC=C1 SRUKMACJNHJLKC-UHFFFAOYSA-N 0.000 claims 1
- BIYBTPPJBAKTOZ-UHFFFAOYSA-N 3-(2,2-dimethylpropyl)-2-phenylindazole Chemical compound N1=C2C=CC=CC2=C(CC(C)(C)C)N1C1=CC=CC=C1 BIYBTPPJBAKTOZ-UHFFFAOYSA-N 0.000 claims 1
- QZQKPQNGVQFCAF-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-2-phenylindazole Chemical compound C1=CC(OC)=CC=C1CC1=C2C=CC=CC2=NN1C1=CC=CC=C1 QZQKPQNGVQFCAF-UHFFFAOYSA-N 0.000 claims 1
- DONUWWGXKUYKMA-UHFFFAOYSA-N 3-[(6-methoxynaphthalen-2-yl)methyl]-2-phenylindazole Chemical compound C1=CC2=CC(OC)=CC=C2C=C1CC(=C1C=CC=CC1=N1)N1C1=CC=CC=C1 DONUWWGXKUYKMA-UHFFFAOYSA-N 0.000 claims 1
- AJZJBELIJMRNOI-UHFFFAOYSA-N 3-[2-(oxan-2-yloxy)ethyl]-2-phenylindazole Chemical compound C1CCCOC1OCCC(=C1C=CC=CC1=N1)N1C1=CC=CC=C1 AJZJBELIJMRNOI-UHFFFAOYSA-N 0.000 claims 1
- VOCDCROOLRFHAU-UHFFFAOYSA-N 3-benzyl-2-(2-fluorophenyl)indazole Chemical compound FC1=CC=CC=C1N1C(CC=2C=CC=CC=2)=C2C=CC=CC2=N1 VOCDCROOLRFHAU-UHFFFAOYSA-N 0.000 claims 1
- HATMWEZYCKVIRP-UHFFFAOYSA-N 3-benzyl-2-(2-phenylethyl)indazole Chemical compound C=1C=CC=CC=1CCN1N=C2C=CC=CC2=C1CC1=CC=CC=C1 HATMWEZYCKVIRP-UHFFFAOYSA-N 0.000 claims 1
- GOWDMQFBIFYVED-UHFFFAOYSA-N 3-benzyl-2-(4-fluorophenyl)indazole Chemical compound C1=CC(F)=CC=C1N1C(CC=2C=CC=CC=2)=C2C=CC=CC2=N1 GOWDMQFBIFYVED-UHFFFAOYSA-N 0.000 claims 1
- CNMFCNHYXAJVIK-UHFFFAOYSA-N 3-benzyl-2-(4-methoxyphenyl)indazole Chemical compound C1=CC(OC)=CC=C1N1C(CC=2C=CC=CC=2)=C2C=CC=CC2=N1 CNMFCNHYXAJVIK-UHFFFAOYSA-N 0.000 claims 1
- VSHWGRAXNFMAJI-UHFFFAOYSA-N 3-benzyl-2-cyclohexylindazole Chemical compound C=1C=CC=CC=1CC(=C1C=CC=CC1=N1)N1C1CCCCC1 VSHWGRAXNFMAJI-UHFFFAOYSA-N 0.000 claims 1
- GDPKJGUFBGWJGH-UHFFFAOYSA-N 3-benzyl-2-naphthalen-1-ylindazole Chemical compound C=1C=CC2=CC=CC=C2C=1N1N=C2C=CC=CC2=C1CC1=CC=CC=C1 GDPKJGUFBGWJGH-UHFFFAOYSA-N 0.000 claims 1
- WTUKUQGTEPCJBH-UHFFFAOYSA-N 3-benzyl-2-phenylindazole Chemical compound C=1C=CC=CC=1CC(=C1C=CC=CC1=N1)N1C1=CC=CC=C1 WTUKUQGTEPCJBH-UHFFFAOYSA-N 0.000 claims 1
- NLKUYMBXAAWODG-UHFFFAOYSA-N 3-benzyl-2-phenylindazole-5-carboxylic acid Chemical compound C=12C=C(C(=O)O)C=CC2=NN(C=2C=CC=CC=2)C=1CC1=CC=CC=C1 NLKUYMBXAAWODG-UHFFFAOYSA-N 0.000 claims 1
- FCWBPBMKRMPTFP-UHFFFAOYSA-N 3-benzyl-2-phenylpyrazolo[4,3-c]pyridine Chemical compound C=1C=CC=CC=1CC(=C1C=NC=CC1=N1)N1C1=CC=CC=C1 FCWBPBMKRMPTFP-UHFFFAOYSA-N 0.000 claims 1
- DHDNLUNUBWYCRA-UHFFFAOYSA-N 3-benzyl-2-propan-2-ylindazole Chemical compound CC(C)N1N=C2C=CC=CC2=C1CC1=CC=CC=C1 DHDNLUNUBWYCRA-UHFFFAOYSA-N 0.000 claims 1
- SJLHSCORRXNKMS-UHFFFAOYSA-N 3-benzyl-2-pyridin-4-ylindazole Chemical compound C=1C=CC=CC=1CC(=C1C=CC=CC1=N1)N1C1=CC=NC=C1 SJLHSCORRXNKMS-UHFFFAOYSA-N 0.000 claims 1
- BUGIUVNPNPDGAN-UHFFFAOYSA-N 3-benzyl-4-methyl-2-phenylindazole Chemical compound C=12C(C)=CC=CC2=NN(C=2C=CC=CC=2)C=1CC1=CC=CC=C1 BUGIUVNPNPDGAN-UHFFFAOYSA-N 0.000 claims 1
- JXLLLMYGJZRAPI-UHFFFAOYSA-N 3-benzyl-5-methoxy-2-phenylindazole Chemical compound C=12C=C(OC)C=CC2=NN(C=2C=CC=CC=2)C=1CC1=CC=CC=C1 JXLLLMYGJZRAPI-UHFFFAOYSA-N 0.000 claims 1
- HVGOYRDSUIHZFE-UHFFFAOYSA-N 3-benzyl-6-methoxy-2-phenylindazole Chemical compound C=1C=CC=CC=1N1N=C2C=C(OC)C=CC2=C1CC1=CC=CC=C1 HVGOYRDSUIHZFE-UHFFFAOYSA-N 0.000 claims 1
- IQNMGGQDZVNELD-UHFFFAOYSA-N 3-hexyl-2-phenylindazole Chemical compound N1=C2C=CC=CC2=C(CCCCCC)N1C1=CC=CC=C1 IQNMGGQDZVNELD-UHFFFAOYSA-N 0.000 claims 1
- QGECJMZXNMBMAN-UHFFFAOYSA-N 4-(3-benzylindazol-2-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1N1C(CC=2C=CC=CC=2)=C2C=CC=CC2=N1 QGECJMZXNMBMAN-UHFFFAOYSA-N 0.000 claims 1
- LIIUEQZPRKTDBZ-UHFFFAOYSA-N 4-(3-benzylindazol-2-yl)quinoline Chemical compound C=1C=NC2=CC=CC=C2C=1N1N=C2C=CC=CC2=C1CC1=CC=CC=C1 LIIUEQZPRKTDBZ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 229910021605 Palladium(II) bromide Inorganic materials 0.000 claims 1
- 229910021606 Palladium(II) iodide Inorganic materials 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 125000005228 aryl sulfonate group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 claims 1
- VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 claims 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 claims 1
- LMAJREOZDVKQCZ-UHFFFAOYSA-N ditert-butyl-[2-(2-ditert-butylphosphanylphenyl)phenyl]phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1P(C(C)(C)C)C(C)(C)C LMAJREOZDVKQCZ-UHFFFAOYSA-N 0.000 claims 1
- 150000002222 fluorine compounds Chemical class 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- DWKRVYNMXVLPIB-UHFFFAOYSA-N n,n-diethyl-2-(2-phenylindazol-3-yl)ethanamine Chemical compound N1=C2C=CC=CC2=C(CCN(CC)CC)N1C1=CC=CC=C1 DWKRVYNMXVLPIB-UHFFFAOYSA-N 0.000 claims 1
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 claims 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 claims 1
- HNNUTDROYPGBMR-UHFFFAOYSA-L palladium(ii) iodide Chemical compound [Pd+2].[I-].[I-] HNNUTDROYPGBMR-UHFFFAOYSA-L 0.000 claims 1
- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical class P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 229910000160 potassium phosphate Inorganic materials 0.000 claims 1
- 235000011009 potassium phosphates Nutrition 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 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 1
- MWANEGNSAJJSCI-UHFFFAOYSA-N tert-butyl 2-(2-phenylindazol-3-yl)acetate Chemical compound N1=C2C=CC=CC2=C(CC(=O)OC(C)(C)C)N1C1=CC=CC=C1 MWANEGNSAJJSCI-UHFFFAOYSA-N 0.000 claims 1
- LBZIRLAIHWCMOG-UHFFFAOYSA-N tert-butyl 3-(cyclopentylmethyl)-2-phenylindazole-6-carboxylate Chemical compound C=1C=CC=CC=1N1N=C2C=C(C(=O)OC(C)(C)C)C=CC2=C1CC1CCCC1 LBZIRLAIHWCMOG-UHFFFAOYSA-N 0.000 claims 1
- TZKKBKQMPVWPAP-UHFFFAOYSA-N tert-butyl 3-(cyclopropylmethyl)-2-phenylindazole-6-carboxylate Chemical compound C=1C=CC=CC=1N1N=C2C=C(C(=O)OC(C)(C)C)C=CC2=C1CC1CC1 TZKKBKQMPVWPAP-UHFFFAOYSA-N 0.000 claims 1
- UQYKJFFNAXLZTI-UHFFFAOYSA-N tert-butyl 3-(cyclopropylmethyl)-2-pyridin-4-ylindazole-6-carboxylate Chemical compound C=1C=NC=CC=1N1N=C2C=C(C(=O)OC(C)(C)C)C=CC2=C1CC1CC1 UQYKJFFNAXLZTI-UHFFFAOYSA-N 0.000 claims 1
- NOMDOVGAJWYCLQ-UHFFFAOYSA-N tert-butyl 3-benzyl-2-(thiophen-2-ylmethyl)indazole-6-carboxylate Chemical compound C=1C=CSC=1CN1N=C2C=C(C(=O)OC(C)(C)C)C=CC2=C1CC1=CC=CC=C1 NOMDOVGAJWYCLQ-UHFFFAOYSA-N 0.000 claims 1
- YVFDQCFYFJSFQV-UHFFFAOYSA-N tert-butyl 3-benzyl-2-phenylindazole-6-carboxylate Chemical compound C=1C=CC=CC=1N1N=C2C=C(C(=O)OC(C)(C)C)C=CC2=C1CC1=CC=CC=C1 YVFDQCFYFJSFQV-UHFFFAOYSA-N 0.000 claims 1
- DSPCDHSYFGEVQV-UHFFFAOYSA-N tert-butyl 3-benzyl-2-pyridin-4-ylindazole-6-carboxylate Chemical compound C=1C=NC=CC=1N1N=C2C=C(C(=O)OC(C)(C)C)C=CC2=C1CC1=CC=CC=C1 DSPCDHSYFGEVQV-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 0 C[n](c(C*O*)c1*(*)**)nc1O Chemical compound C[n](c(C*O*)c1*(*)**)nc1O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07290799.1 | 2007-06-26 | ||
| EP07290799 | 2007-06-26 | ||
| PCT/EP2008/004637 WO2009000411A1 (en) | 2007-06-26 | 2008-06-11 | A transition metal catalyzed synthesis of 2h-indazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010531311A JP2010531311A (ja) | 2010-09-24 |
| JP2010531311A5 true JP2010531311A5 (enExample) | 2011-07-07 |
| JP5250029B2 JP5250029B2 (ja) | 2013-07-31 |
Family
ID=38577414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010513708A Expired - Fee Related JP5250029B2 (ja) | 2007-06-26 | 2008-06-11 | ２ｈ−インダゾールの遷移金属触媒合成 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8283476B2 (enExample) |
| EP (1) | EP2170833B1 (enExample) |
| JP (1) | JP5250029B2 (enExample) |
| KR (1) | KR20100024963A (enExample) |
| CN (1) | CN101687809A (enExample) |
| AT (1) | ATE511501T1 (enExample) |
| AU (1) | AU2008267442A1 (enExample) |
| BR (1) | BRPI0813870A2 (enExample) |
| CA (1) | CA2693024A1 (enExample) |
| IL (1) | IL202825A0 (enExample) |
| MX (1) | MX2009014203A (enExample) |
| WO (1) | WO2009000411A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2697203B1 (en) * | 2011-04-13 | 2017-05-24 | Merck Sharp & Dohme Corporation | Mineralocorticoid receptor antagonists |
| WO2014068988A1 (en) * | 2012-10-31 | 2014-05-08 | Raqualia Pharma Inc. | Pyrazolopyridine derivatives as ttx-s blockers |
| CN103232462B (zh) * | 2013-05-13 | 2016-03-02 | 湖北科技学院 | 香豆素-吡咯类化合物的合成方法 |
| MX2017011579A (es) * | 2015-03-12 | 2018-03-15 | Du Pont | Pesticidas de tipo azol bicíclicos sustituidos con un heterociclo. |
| KR102095007B1 (ko) * | 2016-02-12 | 2020-03-30 | 주식회사 엘지화학 | 신규한 리간드 화합물 및 전이금속 화합물의 제조방법 |
| KR101931234B1 (ko) | 2016-02-12 | 2018-12-21 | 주식회사 엘지화학 | 신규한 리간드 화합물 및 전이금속 화합물 |
| WO2017138783A1 (ko) * | 2016-02-12 | 2017-08-17 | 주식회사 엘지화학 | 신규한 리간드 화합물 및 전이금속 화합물 |
| KR102038977B1 (ko) * | 2016-12-30 | 2019-11-01 | 사빅 에스케이 넥슬렌 컴퍼니 피티이 엘티디 | 신규한 시클로펜타[ｂ]티오펜일 전이금속 화합물, 이를 포함하는 전이금속 촉매 조성물, 및 이를 이용한 에틸렌 단독중합체 또는 에틸렌과 α-올레핀의 공중합체의 제조방법 |
| CN112533923B (zh) | 2018-06-04 | 2024-07-09 | 爱克思科技有限公司 | 作为腺苷受体拮抗剂的吡唑并嘧啶化合物 |
| CN110317204B (zh) * | 2019-08-02 | 2022-02-08 | 安徽农业大学 | 吡唑并嘧啶酮类衍生物及其制备方法和应用 |
| CN113698349B (zh) * | 2021-09-02 | 2023-08-01 | 河南师范大学 | 一种2-(2-苯基-2h-吲唑-3-基)乙酸酯类化合物的水相光催化制备方法 |
| CN114920699B (zh) * | 2022-05-31 | 2024-03-19 | 甘肃皓天科技股份有限公司 | 一种制备6-氯-2-甲基-2h-吲唑-5-胺的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4647780B2 (ja) * | 1998-02-26 | 2011-03-09 | マサチューセッツ インスティテュート オブ テクノロジー | ヒドラジン、ヒドラゾン、ヒドロキシルアミンおよびオキシムの金属−触媒アリール化およびビニル化 |
-
2008
- 2008-06-11 AT AT08759156T patent/ATE511501T1/de not_active IP Right Cessation
- 2008-06-11 CA CA 2693024 patent/CA2693024A1/en not_active Abandoned
- 2008-06-11 EP EP08759156A patent/EP2170833B1/en not_active Not-in-force
- 2008-06-11 AU AU2008267442A patent/AU2008267442A1/en not_active Abandoned
- 2008-06-11 MX MX2009014203A patent/MX2009014203A/es not_active Application Discontinuation
- 2008-06-11 BR BRPI0813870-2A2A patent/BRPI0813870A2/pt not_active IP Right Cessation
- 2008-06-11 JP JP2010513708A patent/JP5250029B2/ja not_active Expired - Fee Related
- 2008-06-11 WO PCT/EP2008/004637 patent/WO2009000411A1/en not_active Ceased
- 2008-06-11 CN CN200880021936A patent/CN101687809A/zh active Pending
- 2008-06-11 KR KR1020097027096A patent/KR20100024963A/ko not_active Withdrawn
-
2009
- 2009-12-17 IL IL202825A patent/IL202825A0/en unknown
- 2009-12-22 US US12/644,371 patent/US8283476B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010531311A5 (enExample) | ||
| ES2625744T3 (es) | Imidazo[1,2-a]piridinas sustituidas con 3-arilo y su uso | |
| CN110088103B (zh) | 用于治疗和预防乙型肝炎病毒感染的新的四氢吡啶并嘧啶化合物 | |
| JP2006523193A5 (enExample) | ||
| JP2018515573A (ja) | 複素環化合物の合成 | |
| JP2011503096A5 (enExample) | ||
| JP2008535831A (ja) | 環閉鎖および関連する方法および中間体 | |
| CZ300945B6 (cs) | Zpusob prípravy 5-(6-chinazolinyl)-furan-2-karbaldehydu | |
| WO1992020674A1 (en) | 1h-imidazol-1-yl-methyl benzofuran derivatives, with the imidazolyl moiety being substituted by a cycloalkyl group | |
| JP2006502121A (ja) | １Ｈ−イミダゾ［４，５−ｃ］キノリン−４−フタルイミド中間体を介する１Ｈ−イミダゾ−［４，５−ｃ］キノリン−４−アミンの調製 | |
| CN107266428A (zh) | 抗病毒化合物的合成 | |
| JPWO2021069705A5 (enExample) | ||
| WO2022042711A1 (zh) | 新型Rho相关蛋白激酶抑制剂的制备方法和此制备方法中的中间体 | |
| AU2011236671A2 (en) | Process for preparing sulfonamido-benzofuran derivatives | |
| JP2019535813A5 (enExample) | ||
| CN105294699A (zh) | 巴瑞替尼的制备方法 | |
| TW201309692A (zh) | 製造ｈｉｖ吸附抑制劑前藥化合物之方法及其中間物 | |
| JP2019522628A5 (enExample) | ||
| AU2016273360A1 (en) | ROR gamma (RORy) modulators | |
| CS347091A3 (en) | Substituted azoles, process of their preparation and their use | |
| TW202502770A (zh) | 用於製備ｉｒａｋ４抑制劑之程序 | |
| JP2006528667A5 (enExample) | ||
| JP2019526593A5 (enExample) | ||
| RU2011102472A (ru) | Замещенные 7-сульфанилметил-, 7-сульфинилметил- и 7-сульфонилметил-индолы и их применение | |
| RU2007139008A (ru) | 1-ЗАМЕЩЕННЫЕ СОЕДИНЕНИЯ 1Н-ИМИДАЗО[4,5-c]ХИНОЛИН-4-АМИНА И СПОСОБ ИХ ПОЛУЧЕНИЯ |