JP2004506715A5 - - Google Patents

Info

Publication number

JP2004506715A5

JP2004506715A5 JP2002521197A JP2002521197A JP2004506715A5 JP 2004506715 A5 JP2004506715 A5 JP 2004506715A5 JP 2002521197 A JP2002521197 A JP 2002521197A JP 2002521197 A JP2002521197 A JP 2002521197A JP 2004506715 A5 JP2004506715 A5 JP 2004506715A5

Authority

JP

Japan

Prior art keywords

formula

compound

ethanesulfonyl

piperidin

benzyl

Prior art date

2001-08-20

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 23
• -1 cyclic tertiary amines Chemical class 0.000 claims 5
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
• 239000002253 acid Substances 0.000 claims 3
• 125000000217 alkyl group Chemical group 0.000 claims 3
• 201000010099 disease Diseases 0.000 claims 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
• 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 3
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
• 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims 2
• 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims 2
• 239000003814 drug Substances 0.000 claims 2
• 229910052739 hydrogen Inorganic materials 0.000 claims 2
• 239000001257 hydrogen Substances 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• 238000000034 method Methods 0.000 claims 2
• 150000003839 salts Chemical class 0.000 claims 2
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
• FWVHRCVITNUYFV-UHFFFAOYSA-N 4-[(methylazaniumyl)methyl]benzoate Chemical compound CNCC1=CC=C(C(O)=O)C=C1 FWVHRCVITNUYFV-UHFFFAOYSA-N 0.000 claims 1
• JILXIKJEKZOLOE-DENIHFKCSA-N 4-[4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenoxy]-4-oxobutanoic acid Chemical compound C([C@H]([C@H](CC1)CC=2C=CC=CC=2)O)N1CCS(=O)(=O)C1=CC=C(OC(=O)CCC(O)=O)C=C1 JILXIKJEKZOLOE-DENIHFKCSA-N 0.000 claims 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 claims 1
• STGMSHRKRKTLJE-MXBOTTGLSA-N [4-[2-[(3S,4S)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] 2-methyl-4-morpholin-4-ylbenzoate Chemical compound C([C@H]1CCN(C[C@H]1O)CCS(=O)(=O)C1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1C)N1CCOCC1)C1=CC=CC=C1 STGMSHRKRKTLJE-MXBOTTGLSA-N 0.000 claims 1
• DWIBODVLEBRCNQ-ZJSXRUAMSA-N [4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] 3-(3-aminopropanoylamino)propanoate Chemical compound C1=CC(OC(=O)CCNC(=O)CCN)=CC=C1S(=O)(=O)CCN1C[C@@H](O)[C@@H](CC=2C=CC=CC=2)CC1 DWIBODVLEBRCNQ-ZJSXRUAMSA-N 0.000 claims 1
• ICLDVMBBZKNLHW-UFHPHHKVSA-N [4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] 3-(methylaminomethyl)benzoate Chemical compound CNCC1=CC=CC(C(=O)OC=2C=CC(=CC=2)S(=O)(=O)CCN2C[C@@H](O)[C@@H](CC=3C=CC=CC=3)CC2)=C1 ICLDVMBBZKNLHW-UFHPHHKVSA-N 0.000 claims 1
• ZSGMQPYYAUJBTJ-DLFZDVPBSA-N [4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] 3-(morpholin-4-ylmethyl)benzoate Chemical compound C([C@H]([C@H](CC1)CC=2C=CC=CC=2)O)N1CCS(=O)(=O)C(C=C1)=CC=C1OC(=O)C(C=1)=CC=CC=1CN1CCOCC1 ZSGMQPYYAUJBTJ-DLFZDVPBSA-N 0.000 claims 1
• URPKAVROWQYPOZ-AKGWNBJDSA-N [4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] 3-[(4-methylpiperazin-1-yl)methyl]benzoate Chemical compound C1CN(C)CCN1CC1=CC=CC(C(=O)OC=2C=CC(=CC=2)S(=O)(=O)CCN2C[C@@H](O)[C@@H](CC=3C=CC=CC=3)CC2)=C1 URPKAVROWQYPOZ-AKGWNBJDSA-N 0.000 claims 1
• QMNKCPULZHXHJO-SHQCIBLASA-N [4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] 4-(aminomethyl)benzoate Chemical compound C1=CC(CN)=CC=C1C(=O)OC1=CC=C(S(=O)(=O)CCN2C[C@@H](O)[C@@H](CC=3C=CC=CC=3)CC2)C=C1 QMNKCPULZHXHJO-SHQCIBLASA-N 0.000 claims 1
• YMXOSPJJUJZVTR-QLWXXVCSSA-N [4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] 4-[(4-methylpiperazin-1-yl)methyl]benzoate Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)OC=2C=CC(=CC=2)S(=O)(=O)CCN2C[C@@H](O)[C@@H](CC=3C=CC=CC=3)CC2)C=C1 YMXOSPJJUJZVTR-QLWXXVCSSA-N 0.000 claims 1
• GJVDFRLJPJXWOC-YLJYHZDGSA-N [4-[2-[(3s,4s)-4-benzyl-3-hydroxypiperidin-1-yl]ethylsulfonyl]phenyl] dihydrogen phosphate Chemical compound C([C@H]([C@H](CC1)CC=2C=CC=CC=2)O)N1CCS(=O)(=O)C1=CC=C(OP(O)(O)=O)C=C1 GJVDFRLJPJXWOC-YLJYHZDGSA-N 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 claims 1
• 238000005984 hydrogenation reaction Methods 0.000 claims 1
• 125000002757 morpholinyl group Chemical group 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 239000000825 pharmaceutical preparation Substances 0.000 claims 1
• 229940127557 pharmaceutical product Drugs 0.000 claims 1
• 239000000651 prodrug Substances 0.000 claims 1
• 229940002612 prodrug Drugs 0.000 claims 1