JP2006503013A5 - - Google Patents

Info

Publication number

JP2006503013A5

JP2006503013A5 JP2004530186A JP2004530186A JP2006503013A5 JP 2006503013 A5 JP2006503013 A5 JP 2006503013A5 JP 2004530186 A JP2004530186 A JP 2004530186A JP 2004530186 A JP2004530186 A JP 2004530186A JP 2006503013 A5 JP2006503013 A5 JP 2006503013A5

Authority

JP

Japan

Prior art keywords

methyl

xanthine

amino

compound

butyn

Prior art date

2003-08-18

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

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims 42
• 150000003839 salts Chemical class 0.000 claims 26
• -1 4-methoxy-1-naphthylmethyl group Chemical group 0.000 claims 18
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 8
• 238000000034 method Methods 0.000 claims 8
• 239000000203 mixture Substances 0.000 claims 7
• 238000004519 manufacturing process Methods 0.000 claims 6
• 239000008196 pharmacological composition Substances 0.000 claims 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
• 239000008194 pharmaceutical composition Substances 0.000 claims 4
• 238000002360 preparation method Methods 0.000 claims 4
• 125000006239 protecting group Chemical group 0.000 claims 4
• LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 claims 3
• 239000000969 carrier Substances 0.000 claims 3
• 206010012601 diabetes mellitus Diseases 0.000 claims 3
• 239000003085 diluting agent Substances 0.000 claims 3
• 208000008589 Obesity Diseases 0.000 claims 2
• 150000007522 mineralic acids Chemical class 0.000 claims 2
• 235000020824 obesity Nutrition 0.000 claims 2
• 150000007524 organic acids Chemical class 0.000 claims 2
• PEUGKEHLRUVPAN-RXMQYKEDSA-N (3r)-piperidin-3-amine Chemical compound N[C@@H]1CCCNC1 PEUGKEHLRUVPAN-RXMQYKEDSA-N 0.000 claims 1
• VLFSSWGBDCUQHN-ONEGZZNKSA-N 8-(3-aminopiperidin-1-yl)-7-[(e)-but-2-enyl]-1-(isoquinolin-1-ylmethyl)-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=CN=3)C(=O)C=2N(C/C=C/C)C=1N1CCCC(N)C1 VLFSSWGBDCUQHN-ONEGZZNKSA-N 0.000 claims 1
• UPFJNOBWVRMCRL-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-1-(isoquinolin-1-ylmethyl)-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=CN=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 UPFJNOBWVRMCRL-UHFFFAOYSA-N 0.000 claims 1
• HZLSPAMVOSFVEA-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-1-[(4-methoxynaphthalen-1-yl)methyl]-3-methylpurine-2,6-dione Chemical compound C12=CC=CC=C2C(OC)=CC=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(N)C1 HZLSPAMVOSFVEA-UHFFFAOYSA-N 0.000 claims 1
• ILTRPILDWNCOMQ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(quinazolin-2-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=CN=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 ILTRPILDWNCOMQ-UHFFFAOYSA-N 0.000 claims 1
• IVWUOVGPOSTUDO-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(quinolin-4-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4N=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 IVWUOVGPOSTUDO-UHFFFAOYSA-N 0.000 claims 1
• QXEHNRZVDHJFSB-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(quinolin-6-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C=C4C=CC=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 QXEHNRZVDHJFSB-UHFFFAOYSA-N 0.000 claims 1
• DFWUAFCLJJBUNR-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 DFWUAFCLJJBUNR-UHFFFAOYSA-N 0.000 claims 1
• MXOCXLWHNGNQEB-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-[(4-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(C)=CN=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 MXOCXLWHNGNQEB-UHFFFAOYSA-N 0.000 claims 1
• PMEPJDSKCVFSDO-REMYHPOOSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-[(e)-but-2-enyl]-3-methyl-1-(quinazolin-2-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=CN=3)C(=O)C=2N(C/C=C/C)C=1N1CCC[C@@H](N)C1 PMEPJDSKCVFSDO-REMYHPOOSA-N 0.000 claims 1
• UCTWCIQYPZZXKW-VZSQWMKGSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-[(e)-but-2-enyl]-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=C(C)N=3)C(=O)C=2N(C/C=C/C)C=1N1CCC[C@@H](N)C1 UCTWCIQYPZZXKW-VZSQWMKGSA-N 0.000 claims 1
• NNJKEVOXNDMLBL-SHCNBLLESA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-[(e)-but-2-enyl]-3-methyl-1-[(4-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(C)=CN=3)C(=O)C=2N(C/C=C/C)C=1N1CCC[C@@H](N)C1 NNJKEVOXNDMLBL-SHCNBLLESA-N 0.000 claims 1
• HZLSPAMVOSFVEA-LJQANCHMSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-1-[(4-methoxynaphthalen-1-yl)methyl]-3-methylpurine-2,6-dione Chemical compound C12=CC=CC=C2C(OC)=CC=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCC[C@@H](N)C1 HZLSPAMVOSFVEA-LJQANCHMSA-N 0.000 claims 1
• ILTRPILDWNCOMQ-QGZVFWFLSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-(quinazolin-2-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=CN=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 ILTRPILDWNCOMQ-QGZVFWFLSA-N 0.000 claims 1
• DFWUAFCLJJBUNR-LJQANCHMSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 DFWUAFCLJJBUNR-LJQANCHMSA-N 0.000 claims 1
• MXOCXLWHNGNQEB-GOSISDBHSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(4-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(C)=CN=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 MXOCXLWHNGNQEB-GOSISDBHSA-N 0.000 claims 1
• PMEPJDSKCVFSDO-IDOMTICXSA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-[(e)-but-2-enyl]-3-methyl-1-(quinazolin-2-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=CN=3)C(=O)C=2N(C/C=C/C)C=1N1CCC[C@H](N)C1 PMEPJDSKCVFSDO-IDOMTICXSA-N 0.000 claims 1
• UCTWCIQYPZZXKW-PXPVJAHISA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-[(e)-but-2-enyl]-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=C(C)N=3)C(=O)C=2N(C/C=C/C)C=1N1CCC[C@H](N)C1 UCTWCIQYPZZXKW-PXPVJAHISA-N 0.000 claims 1
• NNJKEVOXNDMLBL-WRFKIARRSA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-[(e)-but-2-enyl]-3-methyl-1-[(4-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(C)=CN=3)C(=O)C=2N(C/C=C/C)C=1N1CCC[C@H](N)C1 NNJKEVOXNDMLBL-WRFKIARRSA-N 0.000 claims 1
• HZLSPAMVOSFVEA-IBGZPJMESA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-but-2-ynyl-1-[(4-methoxynaphthalen-1-yl)methyl]-3-methylpurine-2,6-dione Chemical compound C12=CC=CC=C2C(OC)=CC=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCC[C@H](N)C1 HZLSPAMVOSFVEA-IBGZPJMESA-N 0.000 claims 1
• ILTRPILDWNCOMQ-KRWDZBQOSA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-(quinazolin-2-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=CN=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@H](N)C1 ILTRPILDWNCOMQ-KRWDZBQOSA-N 0.000 claims 1
• DFWUAFCLJJBUNR-IBGZPJMESA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@H](N)C1 DFWUAFCLJJBUNR-IBGZPJMESA-N 0.000 claims 1
• MXOCXLWHNGNQEB-SFHVURJKSA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(4-methylisoquinolin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(C)=CN=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@H](N)C1 MXOCXLWHNGNQEB-SFHVURJKSA-N 0.000 claims 1
• LTXREWYXXSTFRX-KRWDZBQOSA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@H](N)C1 LTXREWYXXSTFRX-KRWDZBQOSA-N 0.000 claims 1
• 102000055006 Calcitonin Human genes 0.000 claims 1
• 108060001064 Calcitonin Proteins 0.000 claims 1
• 208000001132 Osteoporosis Diseases 0.000 claims 1
• 206010003246 arthritis Diseases 0.000 claims 1
• BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims 1
• 229960004015 calcitonin Drugs 0.000 claims 1
• 238000007796 conventional method Methods 0.000 claims 1
• 238000002156 mixing Methods 0.000 claims 1
• PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical compound NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 claims 1
• 239000000126 substance Substances 0.000 claims 1
• 238000002054 transplantation Methods 0.000 claims 1