JP2016523246A5 - - Google Patents

Info

Publication number

JP2016523246A5

JP2016523246A5 JP2016520793A JP2016520793A JP2016523246A5 JP 2016523246 A5 JP2016523246 A5 JP 2016523246A5 JP 2016520793 A JP2016520793 A JP 2016520793A JP 2016520793 A JP2016520793 A JP 2016520793A JP 2016523246 A5 JP2016523246 A5 JP 2016523246A5

Authority

JP

Japan

Prior art keywords

compound

base

alkyl

preparing

formula

Prior art date

2014-06-18

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
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• 125000000217 alkyl group Chemical group 0.000 claims 11
• 150000001875 compounds Chemical class 0.000 claims 11
• 125000003709 fluoroalkyl group Chemical group 0.000 claims 6
• 238000000034 method Methods 0.000 claims 6
• 125000006239 protecting group Chemical group 0.000 claims 6
• -1 alkyl fluoroalkyl sulfonates Chemical class 0.000 claims 5
• 238000004519 manufacturing process Methods 0.000 claims 5
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 4
• HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 claims 3
• 229960005167 everolimus Drugs 0.000 claims 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims 3
• 229960002930 sirolimus Drugs 0.000 claims 3
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims 3
• 150000008064 anhydrides Chemical class 0.000 claims 2
• 125000000524 functional group Chemical group 0.000 claims 2
• XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 claims 1
• PGAQYUJUOZNEOE-UHFFFAOYSA-N 2,4-dimethyl-n,n-bis(2-methylpropyl)pentan-3-amine Chemical compound CC(C)CN(CC(C)C)C(C(C)C)C(C)C PGAQYUJUOZNEOE-UHFFFAOYSA-N 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
• 239000000654 additive Substances 0.000 claims 1
• 230000000996 additive effect Effects 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 claims 1
• CERVJSHVWRJDCV-UHFFFAOYSA-N n,n-di(propan-2-yl)nonan-5-amine Chemical compound CCCCC(N(C(C)C)C(C)C)CCCC CERVJSHVWRJDCV-UHFFFAOYSA-N 0.000 claims 1
• BDKMTSFYPWEJRE-UHFFFAOYSA-N n,n-di(propan-2-yl)pentan-3-amine Chemical group CCC(CC)N(C(C)C)C(C)C BDKMTSFYPWEJRE-UHFFFAOYSA-N 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 claims 1
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1