CA2585557C - Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors - Google Patents
Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors Download PDFInfo
- Publication number
- CA2585557C CA2585557C CA002585557A CA2585557A CA2585557C CA 2585557 C CA2585557 C CA 2585557C CA 002585557 A CA002585557 A CA 002585557A CA 2585557 A CA2585557 A CA 2585557A CA 2585557 C CA2585557 C CA 2585557C
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- pyrimidin
- pyrazolo
- amine
- ethoxyethyl
- 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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- 239000002590 phosphodiesterase V inhibitor Substances 0.000 title abstract description 7
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 title abstract description 5
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 415
- 150000001875 compounds Chemical class 0.000 claims abstract description 414
- -1 cyclic guanylate monophosphate Chemical class 0.000 claims abstract description 274
- 238000011282 treatment Methods 0.000 claims abstract description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 195
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 151
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000012453 solvate Substances 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 10
- 101100296726 Caenorhabditis elegans pde-5 gene Proteins 0.000 claims description 9
- 230000009286 beneficial effect Effects 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- FEIOTTPJYXBGOP-UHFFFAOYSA-N 1,3-bis(2-ethoxyethyl)-5-n,5-n-dimethyl-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C)N=C2C(CCOCC)=NN(CCOCC)C2=C1NC1=CC(C)=CC=N1 FEIOTTPJYXBGOP-UHFFFAOYSA-N 0.000 claims description 2
- BLKCIFPIUHPNDB-UHFFFAOYSA-N OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCN(CC1)C(=O)OC(C)(C)C Chemical compound OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCN(CC1)C(=O)OC(C)(C)C BLKCIFPIUHPNDB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- SOKKGTRTVOYRCX-UHFFFAOYSA-N tert-butyl 4-[7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(2,2,2-trifluoroethoxymethyl)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2COCC(F)(F)F)C2=N1 SOKKGTRTVOYRCX-UHFFFAOYSA-N 0.000 claims description 2
- NKVZUKMJXKMWCB-UHFFFAOYSA-N 1-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound N1=C(N2CC(CCC2)C(N)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 NKVZUKMJXKMWCB-UHFFFAOYSA-N 0.000 claims 2
- OQDATHXTNKTVAH-CALCHBBNSA-N 5-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC=CC(C)=N1 OQDATHXTNKTVAH-CALCHBBNSA-N 0.000 claims 2
- HHAULIGFDSRELR-QGZVFWFLSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 HHAULIGFDSRELR-QGZVFWFLSA-N 0.000 claims 1
- PPPYMEOPXVUWCO-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 PPPYMEOPXVUWCO-MRXNPFEDSA-N 0.000 claims 1
- TUCVEIDMALGDIA-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=NC=N1 TUCVEIDMALGDIA-OAHLLOKOSA-N 0.000 claims 1
- NEWAASLDNWLOOG-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-(4-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=C(F)C=C1 NEWAASLDNWLOOG-MRXNPFEDSA-N 0.000 claims 1
- GITXUDXPKFFWLH-QGZVFWFLSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-(6-ethylpyridin-2-yl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(CC)=N1 GITXUDXPKFFWLH-QGZVFWFLSA-N 0.000 claims 1
- CNYYVKXBXUYOEY-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 CNYYVKXBXUYOEY-MRXNPFEDSA-N 0.000 claims 1
- XXZHIDRMOCZAFT-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 XXZHIDRMOCZAFT-OAHLLOKOSA-N 0.000 claims 1
- HCNLOJQGOVQLQQ-CQSZACIVSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=NC=N1 HCNLOJQGOVQLQQ-CQSZACIVSA-N 0.000 claims 1
- NAKPDBFQPWAIHO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-piperazin-1-yl-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2CCNCC2)=NC=1NC1=CC=NC=N1 NAKPDBFQPWAIHO-UHFFFAOYSA-N 0.000 claims 1
- UOWQVSPGTUZNLW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-(3-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=NC=CC=C1C UOWQVSPGTUZNLW-UHFFFAOYSA-N 0.000 claims 1
- GAZBPJSYFHKHNT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC(C)=CC=N1 GAZBPJSYFHKHNT-UHFFFAOYSA-N 0.000 claims 1
- IQTINNXJGBHZFP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(C)=N1 IQTINNXJGBHZFP-UHFFFAOYSA-N 0.000 claims 1
- JXRFSMPVFGDABM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-phenylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC=C1 JXRFSMPVFGDABM-UHFFFAOYSA-N 0.000 claims 1
- DKMYDPXRIRBRHV-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(3-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=NC=CC=C1C DKMYDPXRIRBRHV-MRXNPFEDSA-N 0.000 claims 1
- DYPDWDBQCMHXIP-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 DYPDWDBQCMHXIP-MRXNPFEDSA-N 0.000 claims 1
- WUMNVPPPDAQCCH-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyrimidin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=NC=CC(C)=N1 WUMNVPPPDAQCCH-OAHLLOKOSA-N 0.000 claims 1
- CKLXBKCWYMHANC-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-phenylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=C1 CKLXBKCWYMHANC-MRXNPFEDSA-N 0.000 claims 1
- DYPDWDBQCMHXIP-INIZCTEOSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3s)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 DYPDWDBQCMHXIP-INIZCTEOSA-N 0.000 claims 1
- JZEJSKHODSENIT-INIZCTEOSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3s)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@H](C)NCC2)=NC=1NC1=CC=CC(C)=N1 JZEJSKHODSENIT-INIZCTEOSA-N 0.000 claims 1
- WYOKLIUTLXIBLC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-ethylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(CC)CC1 WYOKLIUTLXIBLC-UHFFFAOYSA-N 0.000 claims 1
- MUXVDKXXOUJOFI-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-ethylpiperidin-4-yl)-7-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(CC)CC1 MUXVDKXXOUJOFI-UHFFFAOYSA-N 0.000 claims 1
- QBWVTNLSVSCFEL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-ethylpiperidin-4-yl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(CC)CC1 QBWVTNLSVSCFEL-UHFFFAOYSA-N 0.000 claims 1
- MZMOWAKPUKLJGP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-methylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C)CC1 MZMOWAKPUKLJGP-UHFFFAOYSA-N 0.000 claims 1
- KEJIFILQJYVKPL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-propan-2-ylpiperidin-4-yl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C(C)C)CC1 KEJIFILQJYVKPL-UHFFFAOYSA-N 0.000 claims 1
- XOPCGQWCEOLCSB-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(piperidin-4-ylmethyl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 XOPCGQWCEOLCSB-UHFFFAOYSA-N 0.000 claims 1
- HRRIBNWFHPLPLR-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC(C)=CC=N1 HRRIBNWFHPLPLR-UHFFFAOYSA-N 0.000 claims 1
- OUBRVKYMSDPJMW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC=C(C)C=N1 OUBRVKYMSDPJMW-UHFFFAOYSA-N 0.000 claims 1
- BWHNNEMQHHTTJC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC=CC=N1 BWHNNEMQHHTTJC-UHFFFAOYSA-N 0.000 claims 1
- FHUOEUSJZABXPZ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-7-n-(3-methylphenyl)-5-n-(1-methylpyrrolidin-3-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CN(C)CC2)=NC=1NC1=CC=CC(C)=C1 FHUOEUSJZABXPZ-UHFFFAOYSA-N 0.000 claims 1
- PFYZHGVAVYUBFG-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-7-n-(4-methylpyridin-2-yl)-5-n-(1-methylpyrrolidin-3-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CN(C)CC2)=NC=1NC1=CC(C)=CC=N1 PFYZHGVAVYUBFG-UHFFFAOYSA-N 0.000 claims 1
- TZBPVZOVQXJOAK-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-piperidin-4-yl-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCNCC1 TZBPVZOVQXJOAK-UHFFFAOYSA-N 0.000 claims 1
- GRYMXFLCUPGRFW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-piperazin-1-yl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC=N1 GRYMXFLCUPGRFW-UHFFFAOYSA-N 0.000 claims 1
- LDLNMLJYTORHKF-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(3-fluorophenyl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=C(F)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 LDLNMLJYTORHKF-UHFFFAOYSA-N 0.000 claims 1
- WPFVQRDMPLDYQI-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(3-methoxyphenyl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=C(OC)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 WPFVQRDMPLDYQI-UHFFFAOYSA-N 0.000 claims 1
- GKUBWDIKHOSFGJ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-fluorophenyl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=CC(F)=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 GKUBWDIKHOSFGJ-UHFFFAOYSA-N 0.000 claims 1
- FSXHZTOSBFMJNT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-(1-propan-2-ylpiperidin-4-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C(C)C)CC1 FSXHZTOSBFMJNT-UHFFFAOYSA-N 0.000 claims 1
- FYRCMBJWMHKGSP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-(2-morpholin-4-ylethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCCN1CCOCC1 FYRCMBJWMHKGSP-UHFFFAOYSA-N 0.000 claims 1
- XDLYAHVCLXQTFX-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 XDLYAHVCLXQTFX-UHFFFAOYSA-N 0.000 claims 1
- SBVLBLDYDBXPBQ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-piperidin-4-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCNCC1 SBVLBLDYDBXPBQ-UHFFFAOYSA-N 0.000 claims 1
- PLOCGLSEEJOBFO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-ethylpyridin-2-yl)-5-n-methyl-5-n-(1-methylpiperidin-4-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC=CC(CC)=N1 PLOCGLSEEJOBFO-UHFFFAOYSA-N 0.000 claims 1
- AMSPIGUJBZIQHY-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-ethylpyridin-2-yl)-5-n-methyl-5-n-(1-methylpyrrolidin-3-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CN(C)CC2)=NC=1NC1=CC=CC(CC)=N1 AMSPIGUJBZIQHY-UHFFFAOYSA-N 0.000 claims 1
- QCUCDXSSDJFTNO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-(1-propan-2-ylpiperidin-4-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C(C)C)CC1 QCUCDXSSDJFTNO-UHFFFAOYSA-N 0.000 claims 1
- INXAFIHEAUEMHU-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-(2-morpholin-4-ylethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCCN1CCOCC1 INXAFIHEAUEMHU-UHFFFAOYSA-N 0.000 claims 1
- JLQIQBLFJBEJTD-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 JLQIQBLFJBEJTD-UHFFFAOYSA-N 0.000 claims 1
- FOEPKDSBOPDZEN-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-piperidin-4-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCNCC1 FOEPKDSBOPDZEN-UHFFFAOYSA-N 0.000 claims 1
- QQVDTGNVTWLTCF-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-phenyl-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 QQVDTGNVTWLTCF-UHFFFAOYSA-N 0.000 claims 1
- GWBZSJGDLCIQOO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)-5-(4-methylpiperazin-1-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(F)=C1 GWBZSJGDLCIQOO-UHFFFAOYSA-N 0.000 claims 1
- WZAYJMNVBWGTEC-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(F)=C1 WZAYJMNVBWGTEC-OAHLLOKOSA-N 0.000 claims 1
- RPEPTARZZYIHPE-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(F)=C1 RPEPTARZZYIHPE-UHFFFAOYSA-N 0.000 claims 1
- DIPTYEMVBCCERV-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methoxyphenyl)-5-(4-methylpiperazin-1-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(OC)=C1 DIPTYEMVBCCERV-UHFFFAOYSA-N 0.000 claims 1
- LXEIVZNLQWRYPZ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methoxyphenyl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(OC)=C1 LXEIVZNLQWRYPZ-UHFFFAOYSA-N 0.000 claims 1
- SEYNTVSJFXWNHU-QGZVFWFLSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methylphenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(C)=C1 SEYNTVSJFXWNHU-QGZVFWFLSA-N 0.000 claims 1
- FTFLQFFFCFEWQC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=NC=CC=C1C FTFLQFFFCFEWQC-UHFFFAOYSA-N 0.000 claims 1
- IOJTWWISEIGGBD-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(4-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=C(F)C=C1 IOJTWWISEIGGBD-OAHLLOKOSA-N 0.000 claims 1
- AFNXLLBJVMVVLQ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC(C)=CC=N1 AFNXLLBJVMVVLQ-UHFFFAOYSA-N 0.000 claims 1
- RVESLZBWSIINGV-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(5-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=C(C)C=N1 RVESLZBWSIINGV-UHFFFAOYSA-N 0.000 claims 1
- RHUURABEIWKMSG-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(C)=N1 RHUURABEIWKMSG-UHFFFAOYSA-N 0.000 claims 1
- XIEAYYVLHOZOEO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-phenyl-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC=C1 XIEAYYVLHOZOEO-UHFFFAOYSA-N 0.000 claims 1
- BQACRCDDFBIQAX-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-(4-methylpiperazin-1-yl)-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC(C)=CC=N1 BQACRCDDFBIQAX-UHFFFAOYSA-N 0.000 claims 1
- VMCOCLYBDRDLSE-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-(4-methylpiperazin-1-yl)-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(C)=N1 VMCOCLYBDRDLSE-UHFFFAOYSA-N 0.000 claims 1
- YVHDEWQLIMAKJD-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-(4-methylpiperazin-1-yl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC=N1 YVHDEWQLIMAKJD-UHFFFAOYSA-N 0.000 claims 1
- KGUYYHZGVBWCDQ-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-methyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 KGUYYHZGVBWCDQ-OAHLLOKOSA-N 0.000 claims 1
- QMCFQTQVCHAMDL-CQSZACIVSA-N 1-(2-ethoxyethyl)-3-methyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 QMCFQTQVCHAMDL-CQSZACIVSA-N 0.000 claims 1
- ZHZMWQQYGLFACT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-piperazin-1-yl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC=N1 ZHZMWQQYGLFACT-UHFFFAOYSA-N 0.000 claims 1
- XCUNWJSUUNZLPM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-n-(6-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(C)=N1 XCUNWJSUUNZLPM-UHFFFAOYSA-N 0.000 claims 1
- SFTMAEWYVZRVMG-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-(4-ethylpiperazin-1-yl)-3-(methoxymethyl)-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2CCN(CC)CC2)=NC=1NC1=CC=NC=N1 SFTMAEWYVZRVMG-UHFFFAOYSA-N 0.000 claims 1
- OCYIZENYTQXCPM-OAHLLOKOSA-N 1-(2-ethoxyethyl)-n-(4-fluorophenyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=C(F)C=C1 OCYIZENYTQXCPM-OAHLLOKOSA-N 0.000 claims 1
- DNCWLPCUHNCWHU-MRXNPFEDSA-N 1-(2-ethoxyethyl)-n-(6-ethylpyridin-2-yl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(CC)=N1 DNCWLPCUHNCWHU-MRXNPFEDSA-N 0.000 claims 1
- VGLBIYCAGGWOPA-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-(4-fluoroanilino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CC(CCC2)C(N)=O)=NC=1NC1=CC=C(F)C=C1 VGLBIYCAGGWOPA-UHFFFAOYSA-N 0.000 claims 1
- GXZQZXDEHAFIGK-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CC(CCC2)C(N)=O)=NC=1NC1=CC(C)=CC=N1 GXZQZXDEHAFIGK-UHFFFAOYSA-N 0.000 claims 1
- WCRZNYFZUQOBDV-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-4-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CC2)C(N)=O)=NC=1NC1=CC(C)=CC=N1 WCRZNYFZUQOBDV-UHFFFAOYSA-N 0.000 claims 1
- YYCDTEXHHPXFSD-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-[(6-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-4-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CC2)C(N)=O)=NC=1NC1=CC=CC(C)=N1 YYCDTEXHHPXFSD-UHFFFAOYSA-N 0.000 claims 1
- CBTKVKJWTOABRM-UHFFFAOYSA-N 1-[3-(ethoxymethyl)-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-ol 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C(C)OCC1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2CCC(CC2)O)CCOCC(F)(F)F CBTKVKJWTOABRM-UHFFFAOYSA-N 0.000 claims 1
- HOKQFCPKIIDGFM-UHFFFAOYSA-N 1-[3-ethyl-7-[(4-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound N1=C(N2CC(CCC2)C(N)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 HOKQFCPKIIDGFM-UHFFFAOYSA-N 0.000 claims 1
- REZOYUVWUDBAOR-UHFFFAOYSA-N 2-[4-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperazin-1-yl]ethanol Chemical compound N1=C(N2CCN(CCO)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 REZOYUVWUDBAOR-UHFFFAOYSA-N 0.000 claims 1
- RAOKRLJQSPBJHF-UHFFFAOYSA-N 3-(cyclopropylmethoxymethyl)-5-piperazin-1-yl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C12=NC(N3CCNCC3)=NC(NC=3N=CN=CC=3)=C2N(CCOCC(F)(F)F)N=C1COCC1CC1 RAOKRLJQSPBJHF-UHFFFAOYSA-N 0.000 claims 1
- YPJRURLHMDFAQL-UHFFFAOYSA-N 3-(ethoxymethyl)-5-(4-methylpiperazin-1-yl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCN(C)CC1 YPJRURLHMDFAQL-UHFFFAOYSA-N 0.000 claims 1
- ZOYXHCXQYKRMDZ-GOSISDBHSA-N 3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(C)=N1 ZOYXHCXQYKRMDZ-GOSISDBHSA-N 0.000 claims 1
- KRUQTMNEBMWLIU-PFEQFJNWSA-N 3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(N2C[C@@H](C)NCC2)N=C2C(COCC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KRUQTMNEBMWLIU-PFEQFJNWSA-N 0.000 claims 1
- KRUQTMNEBMWLIU-UQKRIMTDSA-N 3-(ethoxymethyl)-5-[(3s)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(N2C[C@H](C)NCC2)N=C2C(COCC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KRUQTMNEBMWLIU-UQKRIMTDSA-N 0.000 claims 1
- RTHLTPDYVGEYBH-UHFFFAOYSA-N 3-(ethoxymethyl)-5-piperazin-1-yl-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCNCC1 RTHLTPDYVGEYBH-UHFFFAOYSA-N 0.000 claims 1
- YOIADBZBIOMCDL-MRXNPFEDSA-N 3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-1-(2-propoxyethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 YOIADBZBIOMCDL-MRXNPFEDSA-N 0.000 claims 1
- AVVFUMYYGGYMMF-QGZVFWFLSA-N 3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(C)=N1 AVVFUMYYGGYMMF-QGZVFWFLSA-N 0.000 claims 1
- TUWXCZSSUQGSIV-UHFFFAOYSA-N 3-ethyl-5-(4-ethylpiperazin-1-yl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(CC)CCN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2CC)C2=N1 TUWXCZSSUQGSIV-UHFFFAOYSA-N 0.000 claims 1
- LPIMXICOGCYACY-UHFFFAOYSA-N 3-ethyl-5-(4-ethylsulfonylpiperazin-1-yl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCN(CC2)S(=O)(=O)CC)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 LPIMXICOGCYACY-UHFFFAOYSA-N 0.000 claims 1
- HMXWWEZJHIDDEP-UHFFFAOYSA-N 3-ethyl-5-(4-methyl-1,4-diazepan-1-yl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCN(C)CCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 HMXWWEZJHIDDEP-UHFFFAOYSA-N 0.000 claims 1
- IJUIVMPEWZKWIH-CQSZACIVSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyrimidin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=NC=CC(C)=N1 IJUIVMPEWZKWIH-CQSZACIVSA-N 0.000 claims 1
- WHGIWJDENAGZPX-OAHLLOKOSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC(C)=N1 WHGIWJDENAGZPX-OAHLLOKOSA-N 0.000 claims 1
- MPXCHGIQKTWWQT-CYBMUJFWSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrazin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CN=CC=N1 MPXCHGIQKTWWQT-CYBMUJFWSA-N 0.000 claims 1
- XBIPOXQOAFPLKE-CQSZACIVSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 XBIPOXQOAFPLKE-CQSZACIVSA-N 0.000 claims 1
- UCRSYBKADUKGLT-CYBMUJFWSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 UCRSYBKADUKGLT-CYBMUJFWSA-N 0.000 claims 1
- UCRSYBKADUKGLT-ZDUSSCGKSA-N 3-ethyl-5-[(3s)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 UCRSYBKADUKGLT-ZDUSSCGKSA-N 0.000 claims 1
- MSLJYTVWMHIMIV-UHFFFAOYSA-N 3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 MSLJYTVWMHIMIV-UHFFFAOYSA-N 0.000 claims 1
- DKJUADHNWXNJQF-UHFFFAOYSA-N 3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-pyrazin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CN=CC=N1 DKJUADHNWXNJQF-UHFFFAOYSA-N 0.000 claims 1
- RFUQTPAAFXXWIY-UHFFFAOYSA-N 3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 RFUQTPAAFXXWIY-UHFFFAOYSA-N 0.000 claims 1
- PAIBQHDKQCITSF-UHFFFAOYSA-N 3-ethyl-5-n-methyl-7-n-(4-methylphenyl)-5-n-(1-methylpiperidin-4-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=C1 PAIBQHDKQCITSF-UHFFFAOYSA-N 0.000 claims 1
- OTVPORBTBHZBBY-UHFFFAOYSA-N 3-ethyl-5-piperazin-1-yl-n-pyrazin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CN=CC=N1 OTVPORBTBHZBBY-UHFFFAOYSA-N 0.000 claims 1
- LTSKFIUQHVFYPX-UHFFFAOYSA-N 3-ethyl-7-n-(4-fluorophenyl)-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(F)C=C1 LTSKFIUQHVFYPX-UHFFFAOYSA-N 0.000 claims 1
- YGCVBPWMIHLBJH-CQSZACIVSA-N 3-ethyl-n-(4-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(F)C=C1 YGCVBPWMIHLBJH-CQSZACIVSA-N 0.000 claims 1
- YBBACVAVZQMBOM-UHFFFAOYSA-N 3-ethyl-n-(4-fluorophenyl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(F)C=C1 YBBACVAVZQMBOM-UHFFFAOYSA-N 0.000 claims 1
- GDERROXSQPLAQY-MRXNPFEDSA-N 3-ethyl-n-(4-methylphenyl)-5-[(3r)-3-methylpiperazin-1-yl]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=C1 GDERROXSQPLAQY-MRXNPFEDSA-N 0.000 claims 1
- QEPWMKCPTLKANP-UHFFFAOYSA-N 3-ethyl-n-(4-methylphenyl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=C1 QEPWMKCPTLKANP-UHFFFAOYSA-N 0.000 claims 1
- FGSINUUPXUCXID-UHFFFAOYSA-N 3-ethyl-n-(4-methylpyridin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 FGSINUUPXUCXID-UHFFFAOYSA-N 0.000 claims 1
- JXMQNAMZSSIGDD-UHFFFAOYSA-N 3-ethyl-n-(4-methylpyrimidin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=NC=CC(C)=N1 JXMQNAMZSSIGDD-UHFFFAOYSA-N 0.000 claims 1
- OVLZJPISKIFEAA-UHFFFAOYSA-N 3-ethyl-n-(6-methylpyridin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC(C)=N1 OVLZJPISKIFEAA-UHFFFAOYSA-N 0.000 claims 1
- KEVLUTBMYJZCCE-KRWDZBQOSA-N 3-ethyl-n-pyrimidin-4-yl-5-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2[C@@H](CCC2)CN2CCCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KEVLUTBMYJZCCE-KRWDZBQOSA-N 0.000 claims 1
- PACSWDNFOVMFNZ-UHFFFAOYSA-N 3-methyl-5-(4-methylpiperazin-1-yl)-n-(4-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C1=NC(NC=2N=CC=C(C)C=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 PACSWDNFOVMFNZ-UHFFFAOYSA-N 0.000 claims 1
- TXUISVPZWBYVAL-UHFFFAOYSA-N 3-methyl-5-(4-methylpiperazin-1-yl)-n-(6-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C1=NC(NC=2N=C(C)C=CC=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 TXUISVPZWBYVAL-UHFFFAOYSA-N 0.000 claims 1
- PXIFCRCOYQBRAK-UHFFFAOYSA-N 3-methyl-5-(4-methylpiperazin-1-yl)-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 PXIFCRCOYQBRAK-UHFFFAOYSA-N 0.000 claims 1
- KOBHUQKQHNXZSP-CYBMUJFWSA-N 3-methyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@H](C)CN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 KOBHUQKQHNXZSP-CYBMUJFWSA-N 0.000 claims 1
- OLSXWCSSRFQJRB-UHFFFAOYSA-N 3-methyl-5-piperazin-1-yl-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 OLSXWCSSRFQJRB-UHFFFAOYSA-N 0.000 claims 1
- JPPXWCPFACXJOK-UHFFFAOYSA-N 3-methyl-n-(4-methylpyridin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 JPPXWCPFACXJOK-UHFFFAOYSA-N 0.000 claims 1
- GLMQUPDEVTYSIW-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-fluorophenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCCC2)=NC=1NC1=CC=C(F)C=C1 GLMQUPDEVTYSIW-UHFFFAOYSA-N 0.000 claims 1
- QRQOUVMRMMPLKS-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCCC2)=NC=1NC1=CC(C)=CC=N1 QRQOUVMRMMPLKS-UHFFFAOYSA-N 0.000 claims 1
- KBQCZXKHJACKAD-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-3-ethyl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KBQCZXKHJACKAD-UHFFFAOYSA-N 0.000 claims 1
- JWQSKUQODCDYQU-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-3-methyl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 JWQSKUQODCDYQU-UHFFFAOYSA-N 0.000 claims 1
- DLVTXTOJYQCXOY-UHFFFAOYSA-N 5-(3,4-dimethylpiperazin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CC(C)N(C)CC2)=NC=1NC1=CC(C)=CC=N1 DLVTXTOJYQCXOY-UHFFFAOYSA-N 0.000 claims 1
- PAKNUWOSQFRPIH-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC(F)=C1 PAKNUWOSQFRPIH-UHFFFAOYSA-N 0.000 claims 1
- CIKJBAYSAWJFLF-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(3-methoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC(OC)=C1 CIKJBAYSAWJFLF-UHFFFAOYSA-N 0.000 claims 1
- UMDUIFDDMSVEOP-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-fluorophenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=C(F)C=C1 UMDUIFDDMSVEOP-UHFFFAOYSA-N 0.000 claims 1
- LASVKJLQJACNOV-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC(C)=CC=N1 LASVKJLQJACNOV-UHFFFAOYSA-N 0.000 claims 1
- OWFMCOSQZOAGJK-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-phenylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC=C1 OWFMCOSQZOAGJK-UHFFFAOYSA-N 0.000 claims 1
- IKBHJPDGHXDTTP-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC=N1 IKBHJPDGHXDTTP-UHFFFAOYSA-N 0.000 claims 1
- XNHOANPNYNAQJH-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-methyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC(C)=N1 XNHOANPNYNAQJH-UHFFFAOYSA-N 0.000 claims 1
- BXNGPIIKDFLEGG-ROUUACIJSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-(6-ethylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC(CC)=N1 BXNGPIIKDFLEGG-ROUUACIJSA-N 0.000 claims 1
- XECDTYMNNAVCDO-GJZGRUSLSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=NC=N1 XECDTYMNNAVCDO-GJZGRUSLSA-N 0.000 claims 1
- ISOTXRXRUDXRAI-GJZGRUSLSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-3-(methoxymethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC=N1 ISOTXRXRUDXRAI-GJZGRUSLSA-N 0.000 claims 1
- WLMADZDSQBDONK-IRXDYDNUSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-n-(6-ethylpyridin-2-yl)-3-(methoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC(CC)=N1 WLMADZDSQBDONK-IRXDYDNUSA-N 0.000 claims 1
- GORWAUPRSANCLH-IRXDYDNUSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(ethoxymethyl)-1-(2-propoxyethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC=N1 GORWAUPRSANCLH-IRXDYDNUSA-N 0.000 claims 1
- BQHYPTWIVDNXNY-ROUUACIJSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(ethoxymethyl)-n-(6-methylpyridin-2-yl)-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC(C)=N1 BQHYPTWIVDNXNY-ROUUACIJSA-N 0.000 claims 1
- SHVYXZBRAOEKLQ-ROUUACIJSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-n-(4,6-dimethylpyridin-2-yl)-1-(2-ethoxyethyl)-3-(ethoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC(C)=CC(C)=N1 SHVYXZBRAOEKLQ-ROUUACIJSA-N 0.000 claims 1
- OIHMKXZADULKIA-CQSZACIVSA-N 5-[(3r)-3,4-dimethylpiperazin-1-yl]-3-ethyl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)N(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 OIHMKXZADULKIA-CQSZACIVSA-N 0.000 claims 1
- IOZJYKBDTUBWSV-OAHLLOKOSA-N 5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-3-(4,4,4-trifluorobutoxymethyl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@H](C)CN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2COCCCC(F)(F)F)C2=N1 IOZJYKBDTUBWSV-OAHLLOKOSA-N 0.000 claims 1
- OSRZCRFHOPPVDR-CALCHBBNSA-N 5-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC(C)=CC=N1 OSRZCRFHOPPVDR-CALCHBBNSA-N 0.000 claims 1
- PDLOULNXIJXNIW-ZDUSSCGKSA-N 5-[(3s)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(2,2,2-trifluoroethoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@@H](C)CN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2COCC(F)(F)F)C2=N1 PDLOULNXIJXNIW-ZDUSSCGKSA-N 0.000 claims 1
- AMBSOYSAQQXYJT-IYBDPMFKSA-N 5-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC=CC=N1 AMBSOYSAQQXYJT-IYBDPMFKSA-N 0.000 claims 1
- MROMCAKLKXCOAN-UHFFFAOYSA-N 5-[4-(2-aminoethyl)piperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(CCN)CC2)=NC=1NC1=CC(C)=CC=N1 MROMCAKLKXCOAN-UHFFFAOYSA-N 0.000 claims 1
- DWBODCJIKNJWFW-UHFFFAOYSA-N 5-[4-(2-aminoethyl)piperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(CCN)CC2)=NC=1NC1=CC=CC(C)=N1 DWBODCJIKNJWFW-UHFFFAOYSA-N 0.000 claims 1
- YDMKQZLRKOHBFO-UHFFFAOYSA-N 5-[4-(2-aminoethyl)piperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(CCN)CC2)=NC=1NC1=CC=CC=N1 YDMKQZLRKOHBFO-UHFFFAOYSA-N 0.000 claims 1
- HYPYDFGYXJFEHS-UHFFFAOYSA-N 5-[4-(aminomethyl)piperidin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CN)CC2)=NC=1NC1=CC(C)=CC=N1 HYPYDFGYXJFEHS-UHFFFAOYSA-N 0.000 claims 1
- KDHAYSNKXNPQAU-UHFFFAOYSA-N 5-[4-(aminomethyl)piperidin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CN)CC2)=NC=1NC1=CC=CC(C)=N1 KDHAYSNKXNPQAU-UHFFFAOYSA-N 0.000 claims 1
- IXJRRKVUMKLONX-UHFFFAOYSA-N 5-[4-(aminomethyl)piperidin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CN)CC2)=NC=1NC1=CC=CC=N1 IXJRRKVUMKLONX-UHFFFAOYSA-N 0.000 claims 1
- VGXRBHNQQLSXDW-UHFFFAOYSA-N 5-[[1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)pyrazolo[4,3-d]pyrimidin-7-yl]amino]-1h-pyridin-2-one Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC=1C=CC(=O)NC=1 VGXRBHNQQLSXDW-UHFFFAOYSA-N 0.000 claims 1
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62294104P | 2004-10-28 | 2004-10-28 | |
| US60/622,941 | 2004-10-28 | ||
| PCT/IB2005/003326 WO2006046135A2 (en) | 2004-10-28 | 2005-10-17 | Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2585557A1 CA2585557A1 (en) | 2006-05-04 |
| CA2585557C true CA2585557C (en) | 2009-08-18 |
Family
ID=35530735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002585557A Expired - Fee Related CA2585557C (en) | 2004-10-28 | 2005-10-17 | Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1809632A2 (de) |
| JP (1) | JP2008517994A (de) |
| CA (1) | CA2585557C (de) |
| WO (1) | WO2006046135A2 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1881985B1 (de) | 2005-05-12 | 2010-12-29 | Pfizer, Inc. | Wasserfreie kristalline formen von n-[1,2-ethoxyethyl)-5-(n-ethyl-n-methylamino]-7-(4-methylpyridin-2-yl-amino]-1h-pyrazolo[4,3-d]pyrimidin-3-carbonyl]methansulfonsäureamid |
| NL2000291C2 (nl) * | 2005-11-10 | 2009-02-17 | Pfizer Prod Inc | 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H- pyrazool(4,3-d)pyrimidine-5-yl)piperidine-4-carbonzuur en zouten daarvan. |
| ES2310144B1 (es) | 2007-06-15 | 2010-01-12 | Galenicum Health, S.L. | Intermedios para la preparacion de un inhibidor de la fosfodiesterasa tipo 5. |
| EP2646443B1 (de) | 2010-12-01 | 2014-09-24 | Pfizer Inc | Kat-ii-hemmer |
| US9072301B2 (en) | 2012-02-03 | 2015-07-07 | Basf Se | Fungicidal pyrimidine compounds |
| EA201491667A1 (ru) | 2012-03-13 | 2015-03-31 | Басф Се | Фунгицидные соединения пиримидина |
| WO2014105958A2 (en) | 2012-12-26 | 2014-07-03 | Medivation Technologies, Inc. | Fused pyrimidine compounds and use thereof |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| US11554120B2 (en) * | 2018-08-03 | 2023-01-17 | Bristol-Myers Squibb Company | 1H-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (TLR7) agonists and methods and uses therefor |
| CN115322105A (zh) * | 2021-05-11 | 2022-11-11 | 江苏润安制药有限公司 | 一种合成艾拉莫德关键中间体的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10031584A1 (de) * | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine |
| EP1620437B1 (de) * | 2003-04-29 | 2009-06-17 | Pfizer Limited | 5,7-diaminopyrazolo¬4,3-d pyrimidine zur verwendung in der behandlung von bluthochdruck |
| GB0327319D0 (en) * | 2003-11-24 | 2003-12-24 | Pfizer Ltd | Novel pharmaceuticals |
-
2005
- 2005-10-17 WO PCT/IB2005/003326 patent/WO2006046135A2/en not_active Ceased
- 2005-10-17 EP EP05800579A patent/EP1809632A2/de not_active Withdrawn
- 2005-10-17 CA CA002585557A patent/CA2585557C/en not_active Expired - Fee Related
- 2005-10-17 JP JP2007538544A patent/JP2008517994A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008517994A (ja) | 2008-05-29 |
| WO2006046135A3 (en) | 2006-08-17 |
| CA2585557A1 (en) | 2006-05-04 |
| EP1809632A2 (de) | 2007-07-25 |
| WO2006046135A2 (en) | 2006-05-04 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |