JP2006028189A - α2δ−タンパク質へのアフィニティを有するアミノ酸 - Google Patents
α2δ−タンパク質へのアフィニティを有するアミノ酸 Download PDFInfo
- Publication number
- JP2006028189A JP2006028189A JP2005218738A JP2005218738A JP2006028189A JP 2006028189 A JP2006028189 A JP 2006028189A JP 2005218738 A JP2005218738 A JP 2005218738A JP 2005218738 A JP2005218738 A JP 2005218738A JP 2006028189 A JP2006028189 A JP 2006028189A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- aminomethyl
- acid
- phenyl
- heptanoic
- 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
- 150000001413 amino acids Chemical class 0.000 title description 4
- OAMLTMAKONMRPS-UHFFFAOYSA-N 2-(aminomethyl)-4-methyl-6-phenylhexanoic acid Chemical compound NCC(C(O)=O)CC(C)CCC1=CC=CC=C1 OAMLTMAKONMRPS-UHFFFAOYSA-N 0.000 claims abstract description 3
- BGDQKNHPMLDZDT-UHFFFAOYSA-N 2-(aminomethyl)-4-methyl-7-phenylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=CC=C1 BGDQKNHPMLDZDT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 158
- 150000003839 salts Chemical class 0.000 claims description 52
- 208000002193 Pain Diseases 0.000 claims description 39
- -1 chloro, fluoro, amino Chemical group 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 208000035475 disorder Diseases 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 208000004296 neuralgia Diseases 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 208000021722 neuropathic pain Diseases 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 208000019116 sleep disease Diseases 0.000 claims description 6
- IVYDEZGCXPEAHO-HTQZYQBOSA-N (2r,4r)-2-(aminomethyl)-4-methylheptanoic acid Chemical compound CCC[C@@H](C)C[C@H](CN)C(O)=O IVYDEZGCXPEAHO-HTQZYQBOSA-N 0.000 claims description 5
- VCOJPHSIBVJVDU-UHFFFAOYSA-N 2-(aminomethyl)-4,4,8-trimethylnonanoic acid Chemical compound CC(C)CCCC(C)(C)CC(CN)C(O)=O VCOJPHSIBVJVDU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 4
- JNPHHJLPRJPYLC-GHMZBOCLSA-N (2r,4r)-2-(aminomethyl)-4-methyldecanoic acid Chemical compound CCCCCC[C@@H](C)C[C@H](CN)C(O)=O JNPHHJLPRJPYLC-GHMZBOCLSA-N 0.000 claims description 3
- ZPNHCTKBIJFTRN-RNFRBKRXSA-N (2r,4r)-2-(aminomethyl)-4-methylhexanoic acid Chemical compound CC[C@@H](C)C[C@H](CN)C(O)=O ZPNHCTKBIJFTRN-RNFRBKRXSA-N 0.000 claims description 3
- GWEDLMOKJKIBBL-NXEZZACHSA-N (2r,4r)-2-(aminomethyl)-4-methylnonanoic acid Chemical compound CCCCC[C@@H](C)C[C@H](CN)C(O)=O GWEDLMOKJKIBBL-NXEZZACHSA-N 0.000 claims description 3
- AUVUSCICNWUROE-RKDXNWHRSA-N (2r,4r)-2-(aminomethyl)-4-methyloctanoic acid Chemical compound CCCC[C@@H](C)C[C@H](CN)C(O)=O AUVUSCICNWUROE-RKDXNWHRSA-N 0.000 claims description 3
- JNPHHJLPRJPYLC-WDEREUQCSA-N (2r,4s)-2-(aminomethyl)-4-methyldecanoic acid Chemical compound CCCCCC[C@H](C)C[C@H](CN)C(O)=O JNPHHJLPRJPYLC-WDEREUQCSA-N 0.000 claims description 3
- IVYDEZGCXPEAHO-JGVFFNPUSA-N (2r,4s)-2-(aminomethyl)-4-methylheptanoic acid Chemical compound CCC[C@H](C)C[C@H](CN)C(O)=O IVYDEZGCXPEAHO-JGVFFNPUSA-N 0.000 claims description 3
- ZPNHCTKBIJFTRN-NKWVEPMBSA-N (2r,4s)-2-(aminomethyl)-4-methylhexanoic acid Chemical compound CC[C@H](C)C[C@H](CN)C(O)=O ZPNHCTKBIJFTRN-NKWVEPMBSA-N 0.000 claims description 3
- GWEDLMOKJKIBBL-VHSXEESVSA-N (2r,4s)-2-(aminomethyl)-4-methylnonanoic acid Chemical compound CCCCC[C@H](C)C[C@H](CN)C(O)=O GWEDLMOKJKIBBL-VHSXEESVSA-N 0.000 claims description 3
- AUVUSCICNWUROE-DTWKUNHWSA-N (2r,4s)-2-(aminomethyl)-4-methyloctanoic acid Chemical compound CCCC[C@H](C)C[C@H](CN)C(O)=O AUVUSCICNWUROE-DTWKUNHWSA-N 0.000 claims description 3
- GRGUMWYQZHKEFA-GXSJLCMTSA-N (2r,4s)-2-(aminomethyl)-6-cyclobutyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCC1CCC1 GRGUMWYQZHKEFA-GXSJLCMTSA-N 0.000 claims description 3
- AODQXFLYIDSDCY-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-6-cyclohexyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCC1CCCCC1 AODQXFLYIDSDCY-WCQYABFASA-N 0.000 claims description 3
- DRXKCRRVHJGWRK-CMPLNLGQSA-N (2r,4s)-2-(aminomethyl)-6-cyclopentyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCC1CCCC1 DRXKCRRVHJGWRK-CMPLNLGQSA-N 0.000 claims description 3
- CYGGRFBYXBQBAL-WCBMZHEXSA-N (2r,4s)-2-(aminomethyl)-6-cyclopropyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCC1CC1 CYGGRFBYXBQBAL-WCBMZHEXSA-N 0.000 claims description 3
- DAFBQTCNNDVNDS-UHFFFAOYSA-N 2-(aminomethyl)-5-methylheptanoic acid Chemical compound CCC(C)CCC(CN)C(O)=O DAFBQTCNNDVNDS-UHFFFAOYSA-N 0.000 claims description 3
- ZIJSPJLGYVZLDP-UHFFFAOYSA-N 2-(aminomethyl)-8-methylnonanoic acid Chemical compound CC(C)CCCCCC(CN)C(O)=O ZIJSPJLGYVZLDP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000001052 transient effect Effects 0.000 claims description 3
- OAMLTMAKONMRPS-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-4-methyl-6-phenylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCC1=CC=CC=C1 OAMLTMAKONMRPS-DGCLKSJQSA-N 0.000 claims description 2
- MUXSDKRTQODDAW-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-4-methyl-7-[2-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=CC=C1C(F)(F)F MUXSDKRTQODDAW-DGCLKSJQSA-N 0.000 claims description 2
- QNZILSQCELRHSU-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-4-methyl-7-[3-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=CC(C(F)(F)F)=C1 QNZILSQCELRHSU-DGCLKSJQSA-N 0.000 claims description 2
- WOKLCTDEGNYHKT-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-4-methyl-7-[4-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=C(C(F)(F)F)C=C1 WOKLCTDEGNYHKT-DGCLKSJQSA-N 0.000 claims description 2
- BGDQKNHPMLDZDT-TZMCWYRMSA-N (2r,4r)-2-(aminomethyl)-4-methyl-7-phenylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=CC=C1 BGDQKNHPMLDZDT-TZMCWYRMSA-N 0.000 claims description 2
- CKOBGXLQQKROAR-PSASIEDQSA-N (2r,4r)-2-(aminomethyl)-5-cyclobutyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CC1CCC1 CKOBGXLQQKROAR-PSASIEDQSA-N 0.000 claims description 2
- FYZKEPNSXWFCQV-ZYHUDNBSSA-N (2r,4r)-2-(aminomethyl)-5-cyclohexyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CC1CCCCC1 FYZKEPNSXWFCQV-ZYHUDNBSSA-N 0.000 claims description 2
- MDSQRTZAKRGYAM-MWLCHTKSSA-N (2r,4r)-2-(aminomethyl)-5-cyclopentyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CC1CCCC1 MDSQRTZAKRGYAM-MWLCHTKSSA-N 0.000 claims description 2
- ZUFXWZHSIISWCF-VXNVDRBHSA-N (2r,4r)-2-(aminomethyl)-5-cyclopropyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CC1CC1 ZUFXWZHSIISWCF-VXNVDRBHSA-N 0.000 claims description 2
- BSODDLMOSNGNQB-NWDGAFQWSA-N (2r,4r)-2-(aminomethyl)-6-anilino-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCNC1=CC=CC=C1 BSODDLMOSNGNQB-NWDGAFQWSA-N 0.000 claims description 2
- GRGUMWYQZHKEFA-MWLCHTKSSA-N (2r,4r)-2-(aminomethyl)-6-cyclobutyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCC1CCC1 GRGUMWYQZHKEFA-MWLCHTKSSA-N 0.000 claims description 2
- AODQXFLYIDSDCY-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-6-cyclohexyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCC1CCCCC1 AODQXFLYIDSDCY-DGCLKSJQSA-N 0.000 claims description 2
- DRXKCRRVHJGWRK-ZYHUDNBSSA-N (2r,4r)-2-(aminomethyl)-6-cyclopentyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCC1CCCC1 DRXKCRRVHJGWRK-ZYHUDNBSSA-N 0.000 claims description 2
- CYGGRFBYXBQBAL-PSASIEDQSA-N (2r,4r)-2-(aminomethyl)-6-cyclopropyl-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCC1CC1 CYGGRFBYXBQBAL-PSASIEDQSA-N 0.000 claims description 2
- CLTFILOGSNNJQE-ZYHUDNBSSA-N (2r,4r)-2-(aminomethyl)-7-(2,4-difluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=C(F)C=C1F CLTFILOGSNNJQE-ZYHUDNBSSA-N 0.000 claims description 2
- PBHWMLGPNPSMRO-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-7-(2-fluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=CC=C1F PBHWMLGPNPSMRO-DGCLKSJQSA-N 0.000 claims description 2
- MLDDGCKEOQIAMQ-ZYHUDNBSSA-N (2r,4r)-2-(aminomethyl)-7-(3,4-difluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=C(F)C(F)=C1 MLDDGCKEOQIAMQ-ZYHUDNBSSA-N 0.000 claims description 2
- UFAZDKZYGDDYHI-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-7-(3-fluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=CC(F)=C1 UFAZDKZYGDDYHI-DGCLKSJQSA-N 0.000 claims description 2
- GAWAXAXULKPKFZ-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-7-(4-fluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1=CC=C(F)C=C1 GAWAXAXULKPKFZ-DGCLKSJQSA-N 0.000 claims description 2
- STSNNPOAIIYBBX-CHWSQXEVSA-N (2r,4r)-2-(aminomethyl)-7-anilino-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCNC1=CC=CC=C1 STSNNPOAIIYBBX-CHWSQXEVSA-N 0.000 claims description 2
- QHMNERYXAQBFLN-ZYHUDNBSSA-N (2r,4r)-2-(aminomethyl)-7-cyclobutyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1CCC1 QHMNERYXAQBFLN-ZYHUDNBSSA-N 0.000 claims description 2
- HVZNUPVIHLEIIN-TZMCWYRMSA-N (2r,4r)-2-(aminomethyl)-7-cyclohexyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1CCCCC1 HVZNUPVIHLEIIN-TZMCWYRMSA-N 0.000 claims description 2
- XRZMYRVEOIZSJM-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-7-cyclopentyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1CCCC1 XRZMYRVEOIZSJM-DGCLKSJQSA-N 0.000 claims description 2
- XALBZEZYRXJNLG-MWLCHTKSSA-N (2r,4r)-2-(aminomethyl)-7-cyclopropyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCC1CC1 XALBZEZYRXJNLG-MWLCHTKSSA-N 0.000 claims description 2
- ILBJQLDFGJJNSM-ZIAGYGMSSA-N (2r,4r)-2-(aminomethyl)-8-anilino-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCCNC1=CC=CC=C1 ILBJQLDFGJJNSM-ZIAGYGMSSA-N 0.000 claims description 2
- ZMEMGKXYXGNYKM-DGCLKSJQSA-N (2r,4r)-2-(aminomethyl)-8-cyclobutyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCCC1CCC1 ZMEMGKXYXGNYKM-DGCLKSJQSA-N 0.000 claims description 2
- QVWFMNWNPNIOLX-UKRRQHHQSA-N (2r,4r)-2-(aminomethyl)-8-cyclohexyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCCC1CCCCC1 QVWFMNWNPNIOLX-UKRRQHHQSA-N 0.000 claims description 2
- XBVAHDAMQJJFND-ZYHUDNBSSA-N (2r,4r)-2-(aminomethyl)-8-cyclopropyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCCC1CC1 XBVAHDAMQJJFND-ZYHUDNBSSA-N 0.000 claims description 2
- OAMLTMAKONMRPS-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-4-methyl-6-phenylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCC1=CC=CC=C1 OAMLTMAKONMRPS-WCQYABFASA-N 0.000 claims description 2
- MUXSDKRTQODDAW-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-4-methyl-7-[2-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=CC=C1C(F)(F)F MUXSDKRTQODDAW-WCQYABFASA-N 0.000 claims description 2
- QNZILSQCELRHSU-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-4-methyl-7-[3-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=CC(C(F)(F)F)=C1 QNZILSQCELRHSU-WCQYABFASA-N 0.000 claims description 2
- WOKLCTDEGNYHKT-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-4-methyl-7-[4-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=C(C(F)(F)F)C=C1 WOKLCTDEGNYHKT-WCQYABFASA-N 0.000 claims description 2
- BGDQKNHPMLDZDT-GXTWGEPZSA-N (2r,4s)-2-(aminomethyl)-4-methyl-7-phenylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=CC=C1 BGDQKNHPMLDZDT-GXTWGEPZSA-N 0.000 claims description 2
- CKOBGXLQQKROAR-WCBMZHEXSA-N (2r,4s)-2-(aminomethyl)-5-cyclobutyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CC1CCC1 CKOBGXLQQKROAR-WCBMZHEXSA-N 0.000 claims description 2
- FYZKEPNSXWFCQV-CMPLNLGQSA-N (2r,4s)-2-(aminomethyl)-5-cyclohexyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CC1CCCCC1 FYZKEPNSXWFCQV-CMPLNLGQSA-N 0.000 claims description 2
- MDSQRTZAKRGYAM-GXSJLCMTSA-N (2r,4s)-2-(aminomethyl)-5-cyclopentyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CC1CCCC1 MDSQRTZAKRGYAM-GXSJLCMTSA-N 0.000 claims description 2
- ZUFXWZHSIISWCF-IONNQARKSA-N (2r,4s)-2-(aminomethyl)-5-cyclopropyl-4-methylpentanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CC1CC1 ZUFXWZHSIISWCF-IONNQARKSA-N 0.000 claims description 2
- BSODDLMOSNGNQB-VXGBXAGGSA-N (2r,4s)-2-(aminomethyl)-6-anilino-4-methylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCNC1=CC=CC=C1 BSODDLMOSNGNQB-VXGBXAGGSA-N 0.000 claims description 2
- XLIYHZJFDBLAOF-CMPLNLGQSA-N (2r,4s)-2-(aminomethyl)-6-cyclobutyl-4-ethylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](CC)CCC1CCC1 XLIYHZJFDBLAOF-CMPLNLGQSA-N 0.000 claims description 2
- IKNQIYQBUJJRBD-GXTWGEPZSA-N (2r,4s)-2-(aminomethyl)-6-cyclohexyl-4-ethylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](CC)CCC1CCCCC1 IKNQIYQBUJJRBD-GXTWGEPZSA-N 0.000 claims description 2
- GFRPQZQLKCCHOE-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-6-cyclopentyl-4-ethylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](CC)CCC1CCCC1 GFRPQZQLKCCHOE-WCQYABFASA-N 0.000 claims description 2
- MGASGAWQAYBCJE-GXSJLCMTSA-N (2r,4s)-2-(aminomethyl)-6-cyclopropyl-4-ethylhexanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](CC)CCC1CC1 MGASGAWQAYBCJE-GXSJLCMTSA-N 0.000 claims description 2
- CLTFILOGSNNJQE-CMPLNLGQSA-N (2r,4s)-2-(aminomethyl)-7-(2,4-difluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=C(F)C=C1F CLTFILOGSNNJQE-CMPLNLGQSA-N 0.000 claims description 2
- PBHWMLGPNPSMRO-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-7-(2-fluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=CC=C1F PBHWMLGPNPSMRO-WCQYABFASA-N 0.000 claims description 2
- MLDDGCKEOQIAMQ-CMPLNLGQSA-N (2r,4s)-2-(aminomethyl)-7-(3,4-difluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=C(F)C(F)=C1 MLDDGCKEOQIAMQ-CMPLNLGQSA-N 0.000 claims description 2
- UFAZDKZYGDDYHI-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-7-(3-fluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=CC(F)=C1 UFAZDKZYGDDYHI-WCQYABFASA-N 0.000 claims description 2
- GAWAXAXULKPKFZ-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-7-(4-fluorophenyl)-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1=CC=C(F)C=C1 GAWAXAXULKPKFZ-WCQYABFASA-N 0.000 claims description 2
- STSNNPOAIIYBBX-QWHCGFSZSA-N (2r,4s)-2-(aminomethyl)-7-anilino-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCNC1=CC=CC=C1 STSNNPOAIIYBBX-QWHCGFSZSA-N 0.000 claims description 2
- QHMNERYXAQBFLN-CMPLNLGQSA-N (2r,4s)-2-(aminomethyl)-7-cyclobutyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1CCC1 QHMNERYXAQBFLN-CMPLNLGQSA-N 0.000 claims description 2
- HVZNUPVIHLEIIN-GXTWGEPZSA-N (2r,4s)-2-(aminomethyl)-7-cyclohexyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1CCCCC1 HVZNUPVIHLEIIN-GXTWGEPZSA-N 0.000 claims description 2
- XRZMYRVEOIZSJM-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-7-cyclopentyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1CCCC1 XRZMYRVEOIZSJM-WCQYABFASA-N 0.000 claims description 2
- XALBZEZYRXJNLG-GXSJLCMTSA-N (2r,4s)-2-(aminomethyl)-7-cyclopropyl-4-methylheptanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCC1CC1 XALBZEZYRXJNLG-GXSJLCMTSA-N 0.000 claims description 2
- ILBJQLDFGJJNSM-UONOGXRCSA-N (2r,4s)-2-(aminomethyl)-8-anilino-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCCNC1=CC=CC=C1 ILBJQLDFGJJNSM-UONOGXRCSA-N 0.000 claims description 2
- ZMEMGKXYXGNYKM-WCQYABFASA-N (2r,4s)-2-(aminomethyl)-8-cyclobutyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCCC1CCC1 ZMEMGKXYXGNYKM-WCQYABFASA-N 0.000 claims description 2
- QVWFMNWNPNIOLX-DZGCQCFKSA-N (2r,4s)-2-(aminomethyl)-8-cyclohexyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCCC1CCCCC1 QVWFMNWNPNIOLX-DZGCQCFKSA-N 0.000 claims description 2
- BEGXNTKYXSENLR-GXTWGEPZSA-N (2r,4s)-2-(aminomethyl)-8-cyclopentyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCCC1CCCC1 BEGXNTKYXSENLR-GXTWGEPZSA-N 0.000 claims description 2
- XBVAHDAMQJJFND-CMPLNLGQSA-N (2r,4s)-2-(aminomethyl)-8-cyclopropyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@@H](C)CCCCC1CC1 XBVAHDAMQJJFND-CMPLNLGQSA-N 0.000 claims description 2
- KFUYJCLUBOFHHM-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-methylcyclopropyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(C)CC1 KFUYJCLUBOFHHM-UHFFFAOYSA-N 0.000 claims description 2
- RODVCDKFAMWUKC-UHFFFAOYSA-N 2-(aminomethyl)-4,4-dimethylheptanoic acid Chemical compound CCCC(C)(C)CC(CN)C(O)=O RODVCDKFAMWUKC-UHFFFAOYSA-N 0.000 claims description 2
- JVYGCKSEDCBNBD-UHFFFAOYSA-N 2-(aminomethyl)-4-ethyl-8-methylnonanoic acid Chemical compound NCC(C(O)=O)CC(CC)CCCC(C)C JVYGCKSEDCBNBD-UHFFFAOYSA-N 0.000 claims description 2
- IYWIMUAQVYROEC-UHFFFAOYSA-N 2-(aminomethyl)-4-ethyloctanoic acid Chemical compound CCCCC(CC)CC(CN)C(O)=O IYWIMUAQVYROEC-UHFFFAOYSA-N 0.000 claims description 2
- MUXSDKRTQODDAW-UHFFFAOYSA-N 2-(aminomethyl)-4-methyl-7-[2-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=CC=C1C(F)(F)F MUXSDKRTQODDAW-UHFFFAOYSA-N 0.000 claims description 2
- QNZILSQCELRHSU-UHFFFAOYSA-N 2-(aminomethyl)-4-methyl-7-[3-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=CC(C(F)(F)F)=C1 QNZILSQCELRHSU-UHFFFAOYSA-N 0.000 claims description 2
- WOKLCTDEGNYHKT-UHFFFAOYSA-N 2-(aminomethyl)-4-methyl-7-[4-(trifluoromethyl)phenyl]heptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=C(C(F)(F)F)C=C1 WOKLCTDEGNYHKT-UHFFFAOYSA-N 0.000 claims description 2
- JNPHHJLPRJPYLC-UHFFFAOYSA-N 2-(aminomethyl)-4-methyldecanoic acid Chemical compound CCCCCCC(C)CC(CN)C(O)=O JNPHHJLPRJPYLC-UHFFFAOYSA-N 0.000 claims description 2
- IVYDEZGCXPEAHO-UHFFFAOYSA-N 2-(aminomethyl)-4-methylheptanoic acid Chemical compound CCCC(C)CC(CN)C(O)=O IVYDEZGCXPEAHO-UHFFFAOYSA-N 0.000 claims description 2
- ZPNHCTKBIJFTRN-UHFFFAOYSA-N 2-(aminomethyl)-4-methylhexanoic acid Chemical compound CCC(C)CC(CN)C(O)=O ZPNHCTKBIJFTRN-UHFFFAOYSA-N 0.000 claims description 2
- GWEDLMOKJKIBBL-UHFFFAOYSA-N 2-(aminomethyl)-4-methylnonanoic acid Chemical compound CCCCCC(C)CC(CN)C(O)=O GWEDLMOKJKIBBL-UHFFFAOYSA-N 0.000 claims description 2
- AUVUSCICNWUROE-UHFFFAOYSA-N 2-(aminomethyl)-4-methyloctanoic acid Chemical compound CCCCC(C)CC(CN)C(O)=O AUVUSCICNWUROE-UHFFFAOYSA-N 0.000 claims description 2
- CKOBGXLQQKROAR-UHFFFAOYSA-N 2-(aminomethyl)-5-cyclobutyl-4-methylpentanoic acid Chemical compound NCC(C(O)=O)CC(C)CC1CCC1 CKOBGXLQQKROAR-UHFFFAOYSA-N 0.000 claims description 2
- FYZKEPNSXWFCQV-UHFFFAOYSA-N 2-(aminomethyl)-5-cyclohexyl-4-methylpentanoic acid Chemical compound NCC(C(O)=O)CC(C)CC1CCCCC1 FYZKEPNSXWFCQV-UHFFFAOYSA-N 0.000 claims description 2
- MDSQRTZAKRGYAM-UHFFFAOYSA-N 2-(aminomethyl)-5-cyclopentyl-4-methylpentanoic acid Chemical compound NCC(C(O)=O)CC(C)CC1CCCC1 MDSQRTZAKRGYAM-UHFFFAOYSA-N 0.000 claims description 2
- ZUFXWZHSIISWCF-UHFFFAOYSA-N 2-(aminomethyl)-5-cyclopropyl-4-methylpentanoic acid Chemical compound NCC(C(O)=O)CC(C)CC1CC1 ZUFXWZHSIISWCF-UHFFFAOYSA-N 0.000 claims description 2
- RMVUIOJQERTOEF-UHFFFAOYSA-N 2-(aminomethyl)-5-methylnonanoic acid Chemical compound CCCCC(C)CCC(CN)C(O)=O RMVUIOJQERTOEF-UHFFFAOYSA-N 0.000 claims description 2
- FEVOEYZMTDDAKX-UHFFFAOYSA-N 2-(aminomethyl)-5-methyloctanoic acid Chemical compound CCCC(C)CCC(CN)C(O)=O FEVOEYZMTDDAKX-UHFFFAOYSA-N 0.000 claims description 2
- BSODDLMOSNGNQB-UHFFFAOYSA-N 2-(aminomethyl)-6-anilino-4-methylhexanoic acid Chemical compound NCC(C(O)=O)CC(C)CCNC1=CC=CC=C1 BSODDLMOSNGNQB-UHFFFAOYSA-N 0.000 claims description 2
- GRGUMWYQZHKEFA-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclobutyl-4-methylhexanoic acid Chemical compound NCC(C(O)=O)CC(C)CCC1CCC1 GRGUMWYQZHKEFA-UHFFFAOYSA-N 0.000 claims description 2
- PMDMWEBLZQZESX-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclobutyl-5-methylhexanoic acid Chemical compound NCC(C(O)=O)CCC(C)CC1CCC1 PMDMWEBLZQZESX-UHFFFAOYSA-N 0.000 claims description 2
- AODQXFLYIDSDCY-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclohexyl-4-methylhexanoic acid Chemical compound NCC(C(O)=O)CC(C)CCC1CCCCC1 AODQXFLYIDSDCY-UHFFFAOYSA-N 0.000 claims description 2
- COURDXXVDTXEBE-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclohexyl-5-methylhexanoic acid Chemical compound NCC(C(O)=O)CCC(C)CC1CCCCC1 COURDXXVDTXEBE-UHFFFAOYSA-N 0.000 claims description 2
- DRXKCRRVHJGWRK-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclopentyl-4-methylhexanoic acid Chemical compound NCC(C(O)=O)CC(C)CCC1CCCC1 DRXKCRRVHJGWRK-UHFFFAOYSA-N 0.000 claims description 2
- AEGNDPFGAHPRJH-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclopentyl-5-methylhexanoic acid Chemical compound NCC(C(O)=O)CCC(C)CC1CCCC1 AEGNDPFGAHPRJH-UHFFFAOYSA-N 0.000 claims description 2
- CYGGRFBYXBQBAL-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclopropyl-4-methylhexanoic acid Chemical compound NCC(C(O)=O)CC(C)CCC1CC1 CYGGRFBYXBQBAL-UHFFFAOYSA-N 0.000 claims description 2
- DRMMUQYMPABBCM-UHFFFAOYSA-N 2-(aminomethyl)-6-cyclopropyl-5-methylhexanoic acid Chemical compound NCC(C(O)=O)CCC(C)CC1CC1 DRMMUQYMPABBCM-UHFFFAOYSA-N 0.000 claims description 2
- CLTFILOGSNNJQE-UHFFFAOYSA-N 2-(aminomethyl)-7-(2,4-difluorophenyl)-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=C(F)C=C1F CLTFILOGSNNJQE-UHFFFAOYSA-N 0.000 claims description 2
- PBHWMLGPNPSMRO-UHFFFAOYSA-N 2-(aminomethyl)-7-(2-fluorophenyl)-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=CC=C1F PBHWMLGPNPSMRO-UHFFFAOYSA-N 0.000 claims description 2
- MLDDGCKEOQIAMQ-UHFFFAOYSA-N 2-(aminomethyl)-7-(3,4-difluorophenyl)-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=C(F)C(F)=C1 MLDDGCKEOQIAMQ-UHFFFAOYSA-N 0.000 claims description 2
- UFAZDKZYGDDYHI-UHFFFAOYSA-N 2-(aminomethyl)-7-(3-fluorophenyl)-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=CC(F)=C1 UFAZDKZYGDDYHI-UHFFFAOYSA-N 0.000 claims description 2
- GAWAXAXULKPKFZ-UHFFFAOYSA-N 2-(aminomethyl)-7-(4-fluorophenyl)-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1=CC=C(F)C=C1 GAWAXAXULKPKFZ-UHFFFAOYSA-N 0.000 claims description 2
- STSNNPOAIIYBBX-UHFFFAOYSA-N 2-(aminomethyl)-7-anilino-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCNC1=CC=CC=C1 STSNNPOAIIYBBX-UHFFFAOYSA-N 0.000 claims description 2
- QHMNERYXAQBFLN-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclobutyl-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1CCC1 QHMNERYXAQBFLN-UHFFFAOYSA-N 0.000 claims description 2
- FKWAABOJLOFHPI-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclobutyl-5-methylheptanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCC1CCC1 FKWAABOJLOFHPI-UHFFFAOYSA-N 0.000 claims description 2
- HVZNUPVIHLEIIN-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclohexyl-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1CCCCC1 HVZNUPVIHLEIIN-UHFFFAOYSA-N 0.000 claims description 2
- HEJDDKJXEMTDKZ-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclohexyl-5-methylheptanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCC1CCCCC1 HEJDDKJXEMTDKZ-UHFFFAOYSA-N 0.000 claims description 2
- XRZMYRVEOIZSJM-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclopentyl-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1CCCC1 XRZMYRVEOIZSJM-UHFFFAOYSA-N 0.000 claims description 2
- ZVBLOEINCRJWNU-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclopentyl-5-methylheptanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCC1CCCC1 ZVBLOEINCRJWNU-UHFFFAOYSA-N 0.000 claims description 2
- XALBZEZYRXJNLG-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclopropyl-4-methylheptanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCC1CC1 XALBZEZYRXJNLG-UHFFFAOYSA-N 0.000 claims description 2
- MGIHUBJFJFQHFR-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclopropyl-5-methylheptanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCC1CC1 MGIHUBJFJFQHFR-UHFFFAOYSA-N 0.000 claims description 2
- ILBJQLDFGJJNSM-UHFFFAOYSA-N 2-(aminomethyl)-8-anilino-4-methyloctanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCCNC1=CC=CC=C1 ILBJQLDFGJJNSM-UHFFFAOYSA-N 0.000 claims description 2
- ZMEMGKXYXGNYKM-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclobutyl-4-methyloctanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCCC1CCC1 ZMEMGKXYXGNYKM-UHFFFAOYSA-N 0.000 claims description 2
- ZDFVOKUJMYJYPT-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclobutyl-5-methyloctanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCCC1CCC1 ZDFVOKUJMYJYPT-UHFFFAOYSA-N 0.000 claims description 2
- QVWFMNWNPNIOLX-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclohexyl-4-methyloctanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCCC1CCCCC1 QVWFMNWNPNIOLX-UHFFFAOYSA-N 0.000 claims description 2
- WJNYBTRJKBNQGT-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclohexyl-5-methyloctanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCCC1CCCCC1 WJNYBTRJKBNQGT-UHFFFAOYSA-N 0.000 claims description 2
- BEGXNTKYXSENLR-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclopentyl-4-methyloctanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCCC1CCCC1 BEGXNTKYXSENLR-UHFFFAOYSA-N 0.000 claims description 2
- GVYBFAYUAMNBJF-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclopentyl-5-methyloctanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCCC1CCCC1 GVYBFAYUAMNBJF-UHFFFAOYSA-N 0.000 claims description 2
- XBVAHDAMQJJFND-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclopropyl-4-methyloctanoic acid Chemical compound NCC(C(O)=O)CC(C)CCCCC1CC1 XBVAHDAMQJJFND-UHFFFAOYSA-N 0.000 claims description 2
- BVQSCKOSFUUGIX-UHFFFAOYSA-N 2-(aminomethyl)-8-cyclopropyl-5-methyloctanoic acid Chemical compound NCC(C(O)=O)CCC(C)CCCC1CC1 BVQSCKOSFUUGIX-UHFFFAOYSA-N 0.000 claims description 2
- 206010065390 Inflammatory pain Diseases 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 208000020685 sleep-wake disease Diseases 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 239000001706 (4R)-4-methyloctanoic acid Substances 0.000 claims 1
- FNNKSYVSLDBOII-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-butylcyclopropyl)propanoic acid Chemical compound CCCCC1(CC(CN)C(O)=O)CC1 FNNKSYVSLDBOII-UHFFFAOYSA-N 0.000 claims 1
- CBJOIFOXHOEVNC-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-ethylcyclobutyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CC)CCC1 CBJOIFOXHOEVNC-UHFFFAOYSA-N 0.000 claims 1
- OVRXVVRCMLDOFP-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-ethylcyclohexyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CC)CCCCC1 OVRXVVRCMLDOFP-UHFFFAOYSA-N 0.000 claims 1
- CRBHHRHJKOPDKX-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-ethylcyclopentyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CC)CCCC1 CRBHHRHJKOPDKX-UHFFFAOYSA-N 0.000 claims 1
- ILCGXAXLUIJPAO-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-ethylcyclopropyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CC)CC1 ILCGXAXLUIJPAO-UHFFFAOYSA-N 0.000 claims 1
- ADZSPPFAYPWCCU-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-methylcyclobutyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(C)CCC1 ADZSPPFAYPWCCU-UHFFFAOYSA-N 0.000 claims 1
- XTTYASSPMPOFTR-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-methylcyclohexyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(C)CCCCC1 XTTYASSPMPOFTR-UHFFFAOYSA-N 0.000 claims 1
- YRKOWGXJKIIWLX-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-methylcyclopentyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(C)CCCC1 YRKOWGXJKIIWLX-UHFFFAOYSA-N 0.000 claims 1
- GRCACEMINGMWRZ-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-propan-2-ylcyclopropyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(C(C)C)CC1 GRCACEMINGMWRZ-UHFFFAOYSA-N 0.000 claims 1
- DQTPMQKZIIPRMD-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-propylcyclobutyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CCC)CCC1 DQTPMQKZIIPRMD-UHFFFAOYSA-N 0.000 claims 1
- ADAXYYYTHIYEMC-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-propylcyclohexyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CCC)CCCCC1 ADAXYYYTHIYEMC-UHFFFAOYSA-N 0.000 claims 1
- ZKZXOUMQNYLCDE-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-propylcyclopentyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CCC)CCCC1 ZKZXOUMQNYLCDE-UHFFFAOYSA-N 0.000 claims 1
- FDPFSSPAMMZENL-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-propylcyclopropyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(CCC)CC1 FDPFSSPAMMZENL-UHFFFAOYSA-N 0.000 claims 1
- XKYZZDWTMWQEOW-UHFFFAOYSA-N 2-(aminomethyl)-3-[1-(2-methylpropyl)cyclopropyl]propanoic acid Chemical compound NCC(C(O)=O)CC1(CC(C)C)CC1 XKYZZDWTMWQEOW-UHFFFAOYSA-N 0.000 claims 1
- ZTOJKCGCPJHZPN-UHFFFAOYSA-N 2-(aminomethyl)-3-[1-(4-methylpentyl)cyclopropyl]propanoic acid Chemical compound CC(C)CCCC1(CC(CN)C(O)=O)CC1 ZTOJKCGCPJHZPN-UHFFFAOYSA-N 0.000 claims 1
- QRNWJQJJPFXIDQ-UHFFFAOYSA-N 2-(aminomethyl)-4,6-dimethylheptanoic acid Chemical compound CC(C)CC(C)CC(CN)C(O)=O QRNWJQJJPFXIDQ-UHFFFAOYSA-N 0.000 claims 1
- SLVGNMOCKIHWJE-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-ethylcyclobutyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(CC)CCC1 SLVGNMOCKIHWJE-UHFFFAOYSA-N 0.000 claims 1
- HKMFYLYSBNVTRJ-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-ethylcyclohexyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(CC)CCCCC1 HKMFYLYSBNVTRJ-UHFFFAOYSA-N 0.000 claims 1
- JOATWTIYIMXOQY-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-ethylcyclopentyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(CC)CCCC1 JOATWTIYIMXOQY-UHFFFAOYSA-N 0.000 claims 1
- ABEIOGHTSFBHDL-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-ethylcyclopropyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(CC)CC1 ABEIOGHTSFBHDL-UHFFFAOYSA-N 0.000 claims 1
- NUQUXUGKAXGQSE-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-methylcyclobutyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(C)CCC1 NUQUXUGKAXGQSE-UHFFFAOYSA-N 0.000 claims 1
- INCVWAPVRWINSJ-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-methylcyclohexyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(C)CCCCC1 INCVWAPVRWINSJ-UHFFFAOYSA-N 0.000 claims 1
- PONRROAKJGWGGQ-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-methylcyclopentyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(C)CCCC1 PONRROAKJGWGGQ-UHFFFAOYSA-N 0.000 claims 1
- BKJXILUGQICDCA-UHFFFAOYSA-N 2-(aminomethyl)-4-(1-methylcyclopropyl)butanoic acid Chemical compound NCC(C(O)=O)CCC1(C)CC1 BKJXILUGQICDCA-UHFFFAOYSA-N 0.000 claims 1
- WDYGVYMUTNBBRN-UHFFFAOYSA-N 2-(aminomethyl)-4-cyclobutylbutanoic acid Chemical compound NCC(C(O)=O)CCC1CCC1 WDYGVYMUTNBBRN-UHFFFAOYSA-N 0.000 claims 1
- FFLUTBMPHJSPSA-UHFFFAOYSA-N 2-(aminomethyl)-4-cyclohexylbutanoic acid Chemical compound NCC(C(O)=O)CCC1CCCCC1 FFLUTBMPHJSPSA-UHFFFAOYSA-N 0.000 claims 1
- JROTYWAIBWUQOD-UHFFFAOYSA-N 2-(aminomethyl)-4-cyclopentylbutanoic acid Chemical compound NCC(C(O)=O)CCC1CCCC1 JROTYWAIBWUQOD-UHFFFAOYSA-N 0.000 claims 1
- YUDWTXMVQCQLBP-UHFFFAOYSA-N 2-(aminomethyl)-4-cyclopropylbutanoic acid Chemical compound NCC(C(O)=O)CCC1CC1 YUDWTXMVQCQLBP-UHFFFAOYSA-N 0.000 claims 1
- QCBKSYCQBZQPQE-UHFFFAOYSA-N 2-(aminomethyl)-4-ethyl-5-methylhexanoic acid Chemical compound CCC(C(C)C)CC(CN)C(O)=O QCBKSYCQBZQPQE-UHFFFAOYSA-N 0.000 claims 1
- JWKHJJVNVZSORR-UHFFFAOYSA-N 2-(aminomethyl)-4-ethyl-6-methylheptanoic acid Chemical compound CC(C)CC(CC)CC(CN)C(O)=O JWKHJJVNVZSORR-UHFFFAOYSA-N 0.000 claims 1
- DGOKTOLAJZQIIL-UHFFFAOYSA-N 2-(aminomethyl)-4-ethyl-7-methyloctanoic acid Chemical compound CC(C)CCC(CC)CC(CN)C(O)=O DGOKTOLAJZQIIL-UHFFFAOYSA-N 0.000 claims 1
- YQXHFUSNFIRXSP-UHFFFAOYSA-N 2-(aminomethyl)-4-ethylheptanoic acid Chemical compound CCCC(CC)CC(CN)C(O)=O YQXHFUSNFIRXSP-UHFFFAOYSA-N 0.000 claims 1
- BJIZVOAKFOHTPR-UHFFFAOYSA-N 2-(aminomethyl)-4-ethylhexanoic acid Chemical compound CCC(CC)CC(CN)C(O)=O BJIZVOAKFOHTPR-UHFFFAOYSA-N 0.000 claims 1
- LXKLLNQCHORZCO-UHFFFAOYSA-N 2-(aminomethyl)-4-ethylnonanoic acid Chemical compound CCCCCC(CC)CC(CN)C(O)=O LXKLLNQCHORZCO-UHFFFAOYSA-N 0.000 claims 1
- UNUDRVCYSWKPNL-UHFFFAOYSA-N 2-(aminomethyl)-5-ethyl-6-methylheptanoic acid Chemical compound CCC(C(C)C)CCC(CN)C(O)=O UNUDRVCYSWKPNL-UHFFFAOYSA-N 0.000 claims 1
- XBJUDPROTOXXIS-UHFFFAOYSA-N 2-(aminomethyl)-5-ethyl-7-methyloctanoic acid Chemical compound CC(C)CC(CC)CCC(CN)C(O)=O XBJUDPROTOXXIS-UHFFFAOYSA-N 0.000 claims 1
- DACVOLUCTMBDHF-UHFFFAOYSA-N 2-(aminomethyl)-5-ethyl-8-methylnonanoic acid Chemical compound CC(C)CCC(CC)CCC(CN)C(O)=O DACVOLUCTMBDHF-UHFFFAOYSA-N 0.000 claims 1
- UXZFYMXVNWCJSS-UHFFFAOYSA-N 2-(aminomethyl)-5-ethylheptanoic acid Chemical compound CCC(CC)CCC(CN)C(O)=O UXZFYMXVNWCJSS-UHFFFAOYSA-N 0.000 claims 1
- FPPUCNFHAXMDOL-UHFFFAOYSA-N 2-(aminomethyl)-5-ethylnonanoic acid Chemical compound CCCCC(CC)CCC(CN)C(O)=O FPPUCNFHAXMDOL-UHFFFAOYSA-N 0.000 claims 1
- PVXZYIJHXGJLTB-UHFFFAOYSA-N 2-(aminomethyl)-5-ethyloctanoic acid Chemical compound CCCC(CC)CCC(CN)C(O)=O PVXZYIJHXGJLTB-UHFFFAOYSA-N 0.000 claims 1
- HUIRUQKWSBBBLA-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclobutyl-5-ethylheptanoic acid Chemical compound NCC(C(O)=O)CCC(CC)CCC1CCC1 HUIRUQKWSBBBLA-UHFFFAOYSA-N 0.000 claims 1
- QGESBOVCHFDWHR-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclohexyl-5-ethylheptanoic acid Chemical compound NCC(C(O)=O)CCC(CC)CCC1CCCCC1 QGESBOVCHFDWHR-UHFFFAOYSA-N 0.000 claims 1
- DIBMMKKCDAVUEI-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclopentyl-5-ethylheptanoic acid Chemical compound NCC(C(O)=O)CCC(CC)CCC1CCCC1 DIBMMKKCDAVUEI-UHFFFAOYSA-N 0.000 claims 1
- ODBGGXAYNYINSQ-UHFFFAOYSA-N 2-(aminomethyl)-7-cyclopropyl-5-ethylheptanoic acid Chemical compound NCC(C(O)=O)CCC(CC)CCC1CC1 ODBGGXAYNYINSQ-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 230000035807 sensation Effects 0.000 claims 1
- 150000001576 beta-amino acids Chemical class 0.000 abstract description 10
- 108090000312 Calcium Channels Proteins 0.000 abstract description 4
- 102000003922 Calcium Channels Human genes 0.000 abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 104
- 239000000243 solution Substances 0.000 description 76
- 239000000203 mixture Substances 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
- 238000000034 method Methods 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000003814 drug Substances 0.000 description 31
- 235000019439 ethyl acetate Nutrition 0.000 description 30
- 239000003921 oil Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 229940079593 drug Drugs 0.000 description 24
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 238000010992 reflux Methods 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 239000012267 brine Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 238000007792 addition Methods 0.000 description 14
- 201000006417 multiple sclerosis Diseases 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 208000014674 injury Diseases 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000001154 acute effect Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 230000002490 cerebral effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 0 CC(C(c1ccccc1)O1)N(*(C(C*)CC(*)(*)C*)=O)C1=O Chemical compound CC(C(c1ccccc1)O1)N(*(C(C*)CC(*)(*)C*)=O)C1=O 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 206010022437 insomnia Diseases 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 210000005036 nerve Anatomy 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 208000020401 Depressive disease Diseases 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 208000028017 Psychotic disease Diseases 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- JXEHXYFSIOYTAH-SFYZADRCSA-N imagabalin Chemical compound CCC[C@@H](C)C[C@H](N)CC(O)=O JXEHXYFSIOYTAH-SFYZADRCSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000008764 nerve damage Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 230000008733 trauma Effects 0.000 description 5
- ZYZHMSJNPCYUTB-ZDUSSCGKSA-N (1s)-n-benzyl-1-phenylethanamine Chemical compound N([C@@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 ZYZHMSJNPCYUTB-ZDUSSCGKSA-N 0.000 description 4
- KAOWNNSKQZBPBP-RRQHEKLDSA-N (2s)-2-amino-3,5-dimethylheptanoic acid Chemical compound CCC(C)CC(C)[C@H](N)C(O)=O KAOWNNSKQZBPBP-RRQHEKLDSA-N 0.000 description 4
- JXFSPDBIRPRFMH-HIFRSBDPSA-N (3s,5r)-5-methyl-3-(phenylmethoxycarbonylamino)octanoic acid Chemical compound CCC[C@@H](C)C[C@@H](CC(O)=O)NC(=O)OCC1=CC=CC=C1 JXFSPDBIRPRFMH-HIFRSBDPSA-N 0.000 description 4
- LXHFVSWWDNNDPW-SSDOTTSWSA-N (4r)-4-methylheptanoic acid Chemical compound CCC[C@@H](C)CCC(O)=O LXHFVSWWDNNDPW-SSDOTTSWSA-N 0.000 description 4
- FZVVRHWEJSBBDM-CKEIUWERSA-N (4r,5s)-4-methyl-3-[(4r)-4-methylheptanoyl]-5-phenyl-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(C(=O)CC[C@H](C)CCC)[C@H](C)[C@@H]1C1=CC=CC=C1 FZVVRHWEJSBBDM-CKEIUWERSA-N 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 206010012335 Dependence Diseases 0.000 description 4
- 206010021143 Hypoxia Diseases 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 208000028389 Nerve injury Diseases 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000003542 behavioural effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 201000008482 osteoarthritis Diseases 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 208000033808 peripheral neuropathy Diseases 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 4
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- TVLKZPKESPWMLL-SECBINFHSA-N (2r)-1-iodo-2,6-dimethylheptane Chemical compound CC(C)CCC[C@@H](C)CI TVLKZPKESPWMLL-SECBINFHSA-N 0.000 description 3
- YDFXGYXAYDURTF-MNOVXSKESA-N (2s,4r)-4-methyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]heptanoic acid Chemical compound CCC[C@@H](C)C[C@H](C(O)=O)CC(=O)OC(C)(C)C YDFXGYXAYDURTF-MNOVXSKESA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- MGKJIAFHRWWQMB-UHFFFAOYSA-N 2,2,6-trimethylheptanal Chemical compound CC(C)CCCC(C)(C)C=O MGKJIAFHRWWQMB-UHFFFAOYSA-N 0.000 description 3
- QJHSYUGAMYYOFT-UHFFFAOYSA-N 4-methylhexan-2-imine Chemical compound CCC(C)CC(C)=N QJHSYUGAMYYOFT-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000020925 Bipolar disease Diseases 0.000 description 3
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 3
- 208000001640 Fibromyalgia Diseases 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 206010019196 Head injury Diseases 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 3
- 208000023105 Huntington disease Diseases 0.000 description 3
- 208000004454 Hyperalgesia Diseases 0.000 description 3
- 208000008930 Low Back Pain Diseases 0.000 description 3
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 3
- 208000016285 Movement disease Diseases 0.000 description 3
- 208000000112 Myalgia Diseases 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 208000004550 Postoperative Pain Diseases 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 208000006011 Stroke Diseases 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- AMEWIQLMDPIPRK-UHFFFAOYSA-N benzyl 2-cyano-4,4,8-trimethylnon-2-enoate Chemical compound CC(C)CCCC(C)(C)C=C(C#N)C(=O)OCC1=CC=CC=C1 AMEWIQLMDPIPRK-UHFFFAOYSA-N 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 206010020765 hypersomnia Diseases 0.000 description 3
- 230000007954 hypoxia Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- KXTOJNRWWYAZRZ-UHFFFAOYSA-N methyl 2,2,6-trimethylheptanoate Chemical compound COC(=O)C(C)(C)CCCC(C)C KXTOJNRWWYAZRZ-UHFFFAOYSA-N 0.000 description 3
- 230000036651 mood Effects 0.000 description 3
- 208000013465 muscle pain Diseases 0.000 description 3
- 239000003176 neuroleptic agent Substances 0.000 description 3
- 230000000701 neuroleptic effect Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 210000000278 spinal cord Anatomy 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- HUIHVTVFRDJFTM-PLOVASNDSA-N tert-butyl (3s,5r)-5-methyl-3-[(4r,5s)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]octanoate Chemical compound O1C(=O)N(C(=O)[C@H](CC(=O)OC(C)(C)C)C[C@H](C)CCC)[C@H](C)[C@@H]1C1=CC=CC=C1 HUIHVTVFRDJFTM-PLOVASNDSA-N 0.000 description 3
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 3
- 206010044652 trigeminal neuralgia Diseases 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- RCYIBFNZRWQGNB-SECBINFHSA-N (2R)-2,6-dimethylheptan-1-ol Chemical compound CC(C)CCC[C@@H](C)CO RCYIBFNZRWQGNB-SECBINFHSA-N 0.000 description 2
- RBGFMLVEOIDOFA-SNVBAGLBSA-N (3s)-3-amino-5,5-dimethyldecanoic acid Chemical compound CCCCCC(C)(C)C[C@H](N)CC(O)=O RBGFMLVEOIDOFA-SNVBAGLBSA-N 0.000 description 2
- HCSJVDGOFZXVSV-SECBINFHSA-N (3s)-3-amino-5,5-dimethylnonanoic acid Chemical compound CCCCC(C)(C)C[C@H](N)CC(O)=O HCSJVDGOFZXVSV-SECBINFHSA-N 0.000 description 2
- XQAKDRINXAGBMS-MRVPVSSYSA-N (3s)-3-amino-5,5-dimethyloctanoic acid Chemical compound CCCC(C)(C)C[C@H](N)CC(O)=O XQAKDRINXAGBMS-MRVPVSSYSA-N 0.000 description 2
- RGBGNUZUUNNITH-SNVBAGLBSA-N (3s)-3-amino-6-cyclobutyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CC1CCC1 RGBGNUZUUNNITH-SNVBAGLBSA-N 0.000 description 2
- OUWAXAFAZKDWON-GFCCVEGCSA-N (3s)-3-amino-6-cyclohexyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CC1CCCCC1 OUWAXAFAZKDWON-GFCCVEGCSA-N 0.000 description 2
- QQTUKJBKSPXSRP-LLVKDONJSA-N (3s)-3-amino-6-cyclopentyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CC1CCCC1 QQTUKJBKSPXSRP-LLVKDONJSA-N 0.000 description 2
- RJBVPQISTLTOTF-SECBINFHSA-N (3s)-3-amino-6-cyclopropyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CC1CC1 RJBVPQISTLTOTF-SECBINFHSA-N 0.000 description 2
- HGNRCBSMPHEKHP-LLVKDONJSA-N (3s)-3-amino-7-cyclobutyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CCC1CCC1 HGNRCBSMPHEKHP-LLVKDONJSA-N 0.000 description 2
- OMMUUFIGMMZPRA-CYBMUJFWSA-N (3s)-3-amino-7-cyclohexyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CCC1CCCCC1 OMMUUFIGMMZPRA-CYBMUJFWSA-N 0.000 description 2
- XFDKANJHXNKCAX-GFCCVEGCSA-N (3s)-3-amino-7-cyclopentyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CCC1CCCC1 XFDKANJHXNKCAX-GFCCVEGCSA-N 0.000 description 2
- JEDHAONWLTVVPN-SNVBAGLBSA-N (3s)-3-amino-7-cyclopropyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC(C)(C)CCC1CC1 JEDHAONWLTVVPN-SNVBAGLBSA-N 0.000 description 2
- GUEQOLSQPOTTME-RQJHMYQMSA-N (3s,5r)-3-amino-5-methylheptanoic acid Chemical compound CC[C@@H](C)C[C@H](N)CC(O)=O GUEQOLSQPOTTME-RQJHMYQMSA-N 0.000 description 2
- XKWDZEJCUWTBOM-BDAKNGLRSA-N (3s,5r)-3-amino-5-methylnonanoic acid Chemical compound CCCC[C@@H](C)C[C@H](N)CC(O)=O XKWDZEJCUWTBOM-BDAKNGLRSA-N 0.000 description 2
- CFMZXQJDAJXNHS-WLYNEOFISA-N (3s,5r)-3-amino-5-methyloctanoic acid;hydrochloride Chemical compound Cl.CCC[C@@H](C)C[C@H](N)CC(O)=O CFMZXQJDAJXNHS-WLYNEOFISA-N 0.000 description 2
- KTZLGESLBBDBON-SCZZXKLOSA-N (3s,5r)-3-amino-6-cyclobutyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CC1CCC1 KTZLGESLBBDBON-SCZZXKLOSA-N 0.000 description 2
- LLUFEYITTKGMCY-KOLCDFICSA-N (3s,5r)-3-amino-7-cyclobutyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCC1CCC1 LLUFEYITTKGMCY-KOLCDFICSA-N 0.000 description 2
- VNEAZJRSFULCJJ-YPMHNXCESA-N (3s,5r)-3-amino-7-cyclohexyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCC1CCCCC1 VNEAZJRSFULCJJ-YPMHNXCESA-N 0.000 description 2
- HDLUMIBBUPOCSA-PWSUYJOCSA-N (3s,5r)-3-amino-7-cyclopentyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCC1CCCC1 HDLUMIBBUPOCSA-PWSUYJOCSA-N 0.000 description 2
- MRZJJGINLHHLGH-SCZZXKLOSA-N (3s,5r)-3-amino-7-cyclopropyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCC1CC1 MRZJJGINLHHLGH-SCZZXKLOSA-N 0.000 description 2
- OBXBWMQUUXXWKA-PWSUYJOCSA-N (3s,5r)-3-amino-8-cyclobutyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1CCC1 OBXBWMQUUXXWKA-PWSUYJOCSA-N 0.000 description 2
- ZJAJKCCBTNIBID-OCCSQVGLSA-N (3s,5r)-3-amino-8-cyclohexyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1CCCCC1 ZJAJKCCBTNIBID-OCCSQVGLSA-N 0.000 description 2
- JYSIWAYMQXCEHR-YPMHNXCESA-N (3s,5r)-3-amino-8-cyclopentyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1CCCC1 JYSIWAYMQXCEHR-YPMHNXCESA-N 0.000 description 2
- UNFHAQNQBLGTIX-KOLCDFICSA-N (3s,5r)-3-amino-8-cyclopropyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1CC1 UNFHAQNQBLGTIX-KOLCDFICSA-N 0.000 description 2
- JXEHXYFSIOYTAH-YUMQZZPRSA-N (3s,5s)-3-amino-5-methyloctanoic acid Chemical compound CCC[C@H](C)C[C@H](N)CC(O)=O JXEHXYFSIOYTAH-YUMQZZPRSA-N 0.000 description 2
- KTZLGESLBBDBON-WPRPVWTQSA-N (3s,5s)-3-amino-6-cyclobutyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CC1CCC1 KTZLGESLBBDBON-WPRPVWTQSA-N 0.000 description 2
- LLUFEYITTKGMCY-ONGXEEELSA-N (3s,5s)-3-amino-7-cyclobutyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCC1CCC1 LLUFEYITTKGMCY-ONGXEEELSA-N 0.000 description 2
- VNEAZJRSFULCJJ-AAEUAGOBSA-N (3s,5s)-3-amino-7-cyclohexyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCC1CCCCC1 VNEAZJRSFULCJJ-AAEUAGOBSA-N 0.000 description 2
- HDLUMIBBUPOCSA-JQWIXIFHSA-N (3s,5s)-3-amino-7-cyclopentyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCC1CCCC1 HDLUMIBBUPOCSA-JQWIXIFHSA-N 0.000 description 2
- MRZJJGINLHHLGH-WPRPVWTQSA-N (3s,5s)-3-amino-7-cyclopropyl-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCC1CC1 MRZJJGINLHHLGH-WPRPVWTQSA-N 0.000 description 2
- OBXBWMQUUXXWKA-JQWIXIFHSA-N (3s,5s)-3-amino-8-cyclobutyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1CCC1 OBXBWMQUUXXWKA-JQWIXIFHSA-N 0.000 description 2
- ZJAJKCCBTNIBID-JSGCOSHPSA-N (3s,5s)-3-amino-8-cyclohexyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1CCCCC1 ZJAJKCCBTNIBID-JSGCOSHPSA-N 0.000 description 2
- JYSIWAYMQXCEHR-AAEUAGOBSA-N (3s,5s)-3-amino-8-cyclopentyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1CCCC1 JYSIWAYMQXCEHR-AAEUAGOBSA-N 0.000 description 2
- UNFHAQNQBLGTIX-ONGXEEELSA-N (3s,5s)-3-amino-8-cyclopropyl-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1CC1 UNFHAQNQBLGTIX-ONGXEEELSA-N 0.000 description 2
- VZPIUNDOWLDCTC-SNVBAGLBSA-N (4r)-4,8-dimethylnonanoic acid Chemical compound CC(C)CCC[C@@H](C)CCC(O)=O VZPIUNDOWLDCTC-SNVBAGLBSA-N 0.000 description 2
- QPCLKICBIFGGNH-IIDMSEBBSA-N (4r,5s)-4-methyl-3-[(4r)-4-methyloctanoyl]-5-phenyl-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(C(=O)CC[C@H](C)CCCC)[C@H](C)[C@@H]1C1=CC=CC=C1 QPCLKICBIFGGNH-IIDMSEBBSA-N 0.000 description 2
- PPIBJOQGAJBQDF-VXNVDRBHSA-N (4r,5s)-4-methyl-5-phenyl-1,3-oxazolidin-2-one Chemical compound C[C@H]1NC(=O)O[C@H]1C1=CC=CC=C1 PPIBJOQGAJBQDF-VXNVDRBHSA-N 0.000 description 2
- YRZOHUILUXHAJX-GFCCVEGCSA-N (6r)-2,6-dimethyldec-2-ene Chemical compound CCCC[C@@H](C)CCC=C(C)C YRZOHUILUXHAJX-GFCCVEGCSA-N 0.000 description 2
- IJGHAQBTIYFUQA-LLVKDONJSA-N (6r)-2,6-dimethylnon-2-ene Chemical compound CCC[C@@H](C)CCC=C(C)C IJGHAQBTIYFUQA-LLVKDONJSA-N 0.000 description 2
- QPKCDMXLSDFCQD-JTQLQIEISA-N (6s)-8-bromo-2,6-dimethyloct-2-ene Chemical compound BrCC[C@@H](C)CCC=C(C)C QPKCDMXLSDFCQD-JTQLQIEISA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 2
- WFWLNRWOMFMWJY-UHFFFAOYSA-N 2,2,6-trimethylheptan-1-ol Chemical compound CC(C)CCCC(C)(C)CO WFWLNRWOMFMWJY-UHFFFAOYSA-N 0.000 description 2
- WCTDVPDUYQPJRQ-UHFFFAOYSA-N 2-(aminomethyl)-4,8-dimethylnonanoic acid Chemical compound CC(C)CCCC(C)CC(CN)C(O)=O WCTDVPDUYQPJRQ-UHFFFAOYSA-N 0.000 description 2
- MJLVLHNXEOQASX-UHFFFAOYSA-N 2-bromo-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)C(Br)C(O)=O MJLVLHNXEOQASX-UHFFFAOYSA-N 0.000 description 2
- DUYFASMCTHELDM-UHFFFAOYSA-N 3-amino-5-methyl-8-(4-methylphenyl)octanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=C(C)C=C1 DUYFASMCTHELDM-UHFFFAOYSA-N 0.000 description 2
- RGBGNUZUUNNITH-UHFFFAOYSA-N 3-amino-6-cyclobutyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CC1CCC1 RGBGNUZUUNNITH-UHFFFAOYSA-N 0.000 description 2
- KTZLGESLBBDBON-UHFFFAOYSA-N 3-amino-6-cyclobutyl-5-methylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)CC1CCC1 KTZLGESLBBDBON-UHFFFAOYSA-N 0.000 description 2
- OUWAXAFAZKDWON-UHFFFAOYSA-N 3-amino-6-cyclohexyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CC1CCCCC1 OUWAXAFAZKDWON-UHFFFAOYSA-N 0.000 description 2
- QQTUKJBKSPXSRP-UHFFFAOYSA-N 3-amino-6-cyclopentyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CC1CCCC1 QQTUKJBKSPXSRP-UHFFFAOYSA-N 0.000 description 2
- RJBVPQISTLTOTF-UHFFFAOYSA-N 3-amino-6-cyclopropyl-5,5-dimethylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CC1CC1 RJBVPQISTLTOTF-UHFFFAOYSA-N 0.000 description 2
- HGNRCBSMPHEKHP-UHFFFAOYSA-N 3-amino-7-cyclobutyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CCC1CCC1 HGNRCBSMPHEKHP-UHFFFAOYSA-N 0.000 description 2
- LLUFEYITTKGMCY-UHFFFAOYSA-N 3-amino-7-cyclobutyl-5-methylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)CCC1CCC1 LLUFEYITTKGMCY-UHFFFAOYSA-N 0.000 description 2
- OMMUUFIGMMZPRA-UHFFFAOYSA-N 3-amino-7-cyclohexyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CCC1CCCCC1 OMMUUFIGMMZPRA-UHFFFAOYSA-N 0.000 description 2
- VNEAZJRSFULCJJ-UHFFFAOYSA-N 3-amino-7-cyclohexyl-5-methylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)CCC1CCCCC1 VNEAZJRSFULCJJ-UHFFFAOYSA-N 0.000 description 2
- XFDKANJHXNKCAX-UHFFFAOYSA-N 3-amino-7-cyclopentyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CCC1CCCC1 XFDKANJHXNKCAX-UHFFFAOYSA-N 0.000 description 2
- HDLUMIBBUPOCSA-UHFFFAOYSA-N 3-amino-7-cyclopentyl-5-methylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)CCC1CCCC1 HDLUMIBBUPOCSA-UHFFFAOYSA-N 0.000 description 2
- JEDHAONWLTVVPN-UHFFFAOYSA-N 3-amino-7-cyclopropyl-5,5-dimethylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)(C)CCC1CC1 JEDHAONWLTVVPN-UHFFFAOYSA-N 0.000 description 2
- MRZJJGINLHHLGH-UHFFFAOYSA-N 3-amino-7-cyclopropyl-5-methylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)CCC1CC1 MRZJJGINLHHLGH-UHFFFAOYSA-N 0.000 description 2
- OBXBWMQUUXXWKA-UHFFFAOYSA-N 3-amino-8-cyclobutyl-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1CCC1 OBXBWMQUUXXWKA-UHFFFAOYSA-N 0.000 description 2
- ZJAJKCCBTNIBID-UHFFFAOYSA-N 3-amino-8-cyclohexyl-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1CCCCC1 ZJAJKCCBTNIBID-UHFFFAOYSA-N 0.000 description 2
- JYSIWAYMQXCEHR-UHFFFAOYSA-N 3-amino-8-cyclopentyl-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1CCCC1 JYSIWAYMQXCEHR-UHFFFAOYSA-N 0.000 description 2
- UNFHAQNQBLGTIX-UHFFFAOYSA-N 3-amino-8-cyclopropyl-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1CC1 UNFHAQNQBLGTIX-UHFFFAOYSA-N 0.000 description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 208000001387 Causalgia Diseases 0.000 description 2
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 206010012239 Delusion Diseases 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- 208000012661 Dyskinesia Diseases 0.000 description 2
- 208000027534 Emotional disease Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- 208000035154 Hyperesthesia Diseases 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 208000036626 Mental retardation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 208000008238 Muscle Spasticity Diseases 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 208000006199 Parasomnias Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 206010040744 Sinus headache Diseases 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 208000001407 Vascular Headaches Diseases 0.000 description 2
- REOTWSUDNJILTP-NSHDSACASA-N [(3s)-3,7-dimethyloct-6-enyl] methanesulfonate Chemical compound CS(=O)(=O)OCC[C@@H](C)CCC=C(C)C REOTWSUDNJILTP-NSHDSACASA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 208000028683 bipolar I disease Diseases 0.000 description 2
- 210000003461 brachial plexus Anatomy 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 2
- 229940005991 chloric acid Drugs 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000001916 cyano esters Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 231100000868 delusion Toxicity 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- HWBKVBDRPINQOU-MRVPVSSYSA-N ethyl (3s)-3-methylhex-4-enoate Chemical compound CCOC(=O)C[C@H](C)C=CC HWBKVBDRPINQOU-MRVPVSSYSA-N 0.000 description 2
- ZNRBKJNOXYTPQX-UHFFFAOYSA-N ethyl 2-(aminomethyl)-3-(1-methylcyclopropyl)propanoate Chemical compound CCOC(=O)C(CN)CC1(C)CC1 ZNRBKJNOXYTPQX-UHFFFAOYSA-N 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 208000024714 major depressive disease Diseases 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000003340 mental effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 201000003631 narcolepsy Diseases 0.000 description 2
- 239000006199 nebulizer Substances 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 230000002981 neuropathic effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
- 208000019906 panic disease Diseases 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 208000030062 persistent idiopathic facial pain Diseases 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000002271 resection Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 230000007958 sleep Effects 0.000 description 2
- 201000002859 sleep apnea Diseases 0.000 description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 208000018198 spasticity Diseases 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- VIXLUXLQHUBMGG-NAMMGXCXSA-N tert-butyl (3r,5s)-3-[benzyl(1-phenylethyl)amino]-5-methyloct-6-enoate Chemical compound C=1C=CC=CC=1C(C)N([C@@H](CC(=O)OC(C)(C)C)C[C@H](C)C=CC)CC1=CC=CC=C1 VIXLUXLQHUBMGG-NAMMGXCXSA-N 0.000 description 2
- DKPAQXMFEIGQCB-NEPJUHHUSA-N tert-butyl (3s,5r)-3-amino-5-methylnonanoate Chemical compound CCCC[C@@H](C)C[C@H](N)CC(=O)OC(C)(C)C DKPAQXMFEIGQCB-NEPJUHHUSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- 208000004371 toothache Diseases 0.000 description 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 description 2
- 208000019553 vascular disease Diseases 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- PIZQWRXTMGASCZ-UHFFFAOYSA-N (1-methylcyclopropyl)methanol Chemical compound OCC1(C)CC1 PIZQWRXTMGASCZ-UHFFFAOYSA-N 0.000 description 1
- ZYZHMSJNPCYUTB-CYBMUJFWSA-N (1r)-n-benzyl-1-phenylethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 ZYZHMSJNPCYUTB-CYBMUJFWSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- FYMCYTATQMTTGM-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl) cyclopropanecarboxylate Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OC(=O)C1CC1 FYMCYTATQMTTGM-UHFFFAOYSA-N 0.000 description 1
- UTNRJIHVBWRHPC-UHFFFAOYSA-N (2-tert-butyl-4-methylphenyl) cyclopropanecarboxylate Chemical compound C1(CC1)C(=O)OC1=C(C=C(C=C1)C)C(C)(C)C UTNRJIHVBWRHPC-UHFFFAOYSA-N 0.000 description 1
- WZCSGWJFDMJJIQ-HACHORDNSA-N (2S)-2-amino-3,5-dimethyloctanoic acid Chemical compound N[C@H](C(=O)O)C(CC(CCC)C)C WZCSGWJFDMJJIQ-HACHORDNSA-N 0.000 description 1
- KIBOHRIGZMLNNS-BYPYZUCNSA-N (2r)-3-bromo-2-methylpropan-1-ol Chemical compound OC[C@@H](C)CBr KIBOHRIGZMLNNS-BYPYZUCNSA-N 0.000 description 1
- BEGXNTKYXSENLR-TZMCWYRMSA-N (2r,4r)-2-(aminomethyl)-8-cyclopentyl-4-methyloctanoic acid Chemical compound NC[C@H](C(O)=O)C[C@H](C)CCCCC1CCCC1 BEGXNTKYXSENLR-TZMCWYRMSA-N 0.000 description 1
- GYENDRLMVQQPFJ-ZJLYAJKPSA-N (2r,4r)-2-amino-4-methylheptanoic acid;hydrochloride Chemical compound Cl.CCC[C@@H](C)C[C@@H](N)C(O)=O GYENDRLMVQQPFJ-ZJLYAJKPSA-N 0.000 description 1
- CSDUHKBQMQQYNC-RQJHMYQMSA-N (2s)-2-[(2r)-2-methylbutyl]butanedioic acid Chemical compound CC[C@@H](C)C[C@H](C(O)=O)CC(O)=O CSDUHKBQMQQYNC-RQJHMYQMSA-N 0.000 description 1
- QQLMYDATNWMBAS-BDAKNGLRSA-N (2s)-2-[(2r)-2-methylhexyl]butanedioic acid Chemical compound CCCC[C@@H](C)C[C@H](C(O)=O)CC(O)=O QQLMYDATNWMBAS-BDAKNGLRSA-N 0.000 description 1
- LZFGKZWECGDCGN-SFYZADRCSA-N (2s)-2-[(2r)-2-methylpentyl]butanedioic acid Chemical compound CCC[C@@H](C)C[C@H](C(O)=O)CC(O)=O LZFGKZWECGDCGN-SFYZADRCSA-N 0.000 description 1
- DQZWXDKUALGTBI-RTBKNWGFSA-N (2s)-2-amino-3,5-dimethylnonanoic acid Chemical compound CCCCC(C)CC(C)[C@H](N)C(O)=O DQZWXDKUALGTBI-RTBKNWGFSA-N 0.000 description 1
- PBEBBYQZIJHKSL-LLVKDONJSA-N (2s)-4,4-dimethyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]heptanoic acid Chemical compound CCCC(C)(C)C[C@H](C(O)=O)CC(=O)OC(C)(C)C PBEBBYQZIJHKSL-LLVKDONJSA-N 0.000 description 1
- GYENDRLMVQQPFJ-HHQFNNIRSA-N (2s,4r)-2-amino-4-methylheptanoic acid;hydrochloride Chemical compound Cl.CCC[C@@H](C)C[C@H](N)C(O)=O GYENDRLMVQQPFJ-HHQFNNIRSA-N 0.000 description 1
- SKZYWVHZXPYGLU-ZJUUUORDSA-N (2s,4r)-4-methyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]hexanoic acid Chemical compound CC[C@@H](C)C[C@H](C(O)=O)CC(=O)OC(C)(C)C SKZYWVHZXPYGLU-ZJUUUORDSA-N 0.000 description 1
- YCFOHCAYQLLZFX-NEPJUHHUSA-N (2s,4r)-4-methyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]octanoic acid Chemical compound CCCC[C@@H](C)C[C@H](C(O)=O)CC(=O)OC(C)(C)C YCFOHCAYQLLZFX-NEPJUHHUSA-N 0.000 description 1
- JOZHVTLFJVMINU-IVFYJWHCSA-N (3S,5R)-3-amino-5-methylnonanoic acid (4R)-4-methyloctanoic acid Chemical compound C[C@@H](CCC(=O)O)CCCC.N[C@H](CC(=O)O)C[C@@H](CCCC)C JOZHVTLFJVMINU-IVFYJWHCSA-N 0.000 description 1
- AJBZEKIELRMWEU-IIHSZXCVSA-N (3S,5R)-5-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]nonanoic acid Chemical compound C[C@@H](C[C@@H](CC(=O)O)C(=O)N1C(O[C@H]([C@H]1C)C1=CC=CC=C1)=O)CCCC AJBZEKIELRMWEU-IIHSZXCVSA-N 0.000 description 1
- TZHLPMZJLIAOHQ-RRKGBCIJSA-N (3r)-3-amino-5,9-dimethyldecanoic acid Chemical compound CC(C)CCCC(C)C[C@@H](N)CC(O)=O TZHLPMZJLIAOHQ-RRKGBCIJSA-N 0.000 description 1
- JNILHKVTKKZTKO-RNFRBKRXSA-N (3r,4r)-3-amino-4,5-dimethylhexanoic acid Chemical compound CC(C)[C@@H](C)[C@H](N)CC(O)=O JNILHKVTKKZTKO-RNFRBKRXSA-N 0.000 description 1
- NFVLCHFMYBGJHD-HTQZYQBOSA-N (3r,4r)-3-amino-4,6-dimethylheptanoic acid Chemical compound CC(C)C[C@@H](C)[C@H](N)CC(O)=O NFVLCHFMYBGJHD-HTQZYQBOSA-N 0.000 description 1
- VLWJBYXEBQRSMA-RKDXNWHRSA-N (3r,4r)-3-amino-4,7-dimethyloctanoic acid Chemical compound CC(C)CC[C@@H](C)[C@H](N)CC(O)=O VLWJBYXEBQRSMA-RKDXNWHRSA-N 0.000 description 1
- ULBMATTTZLROEN-NXEZZACHSA-N (3r,4r)-3-amino-4,8-dimethylnonanoic acid Chemical compound CC(C)CCC[C@@H](C)[C@H](N)CC(O)=O ULBMATTTZLROEN-NXEZZACHSA-N 0.000 description 1
- OOSQZJATKLDLNT-GHMZBOCLSA-N (3r,4r)-3-amino-4,9-dimethyldecanoic acid Chemical compound CC(C)CCCC[C@@H](C)[C@H](N)CC(O)=O OOSQZJATKLDLNT-GHMZBOCLSA-N 0.000 description 1
- SLWLIZJXWOIOIT-HTRCEHHLSA-N (3r,4r)-3-amino-4-cyclobutylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)C1CCC1 SLWLIZJXWOIOIT-HTRCEHHLSA-N 0.000 description 1
- CAXPLTIMYMSSQM-PSASIEDQSA-N (3r,4r)-3-amino-4-cyclohexylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)C1CCCCC1 CAXPLTIMYMSSQM-PSASIEDQSA-N 0.000 description 1
- BDSFBZHOMCDBGL-VXNVDRBHSA-N (3r,4r)-3-amino-4-cyclopentylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)C1CCCC1 BDSFBZHOMCDBGL-VXNVDRBHSA-N 0.000 description 1
- SWPZRWPZRQZIJV-IYSWYEEDSA-N (3r,4r)-3-amino-4-cyclopropylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)C1CC1 SWPZRWPZRQZIJV-IYSWYEEDSA-N 0.000 description 1
- WORUZBFCUXZOHJ-NXEZZACHSA-N (3r,4r)-3-amino-4-methyldecanoic acid Chemical compound CCCCCC[C@@H](C)[C@H](N)CC(O)=O WORUZBFCUXZOHJ-NXEZZACHSA-N 0.000 description 1
- KEZZGIFSTDSATA-RKDXNWHRSA-N (3r,4r)-3-amino-4-methylnonanoic acid Chemical compound CCCCC[C@@H](C)[C@H](N)CC(O)=O KEZZGIFSTDSATA-RKDXNWHRSA-N 0.000 description 1
- WNDLIPKAWDXSDD-HTQZYQBOSA-N (3r,4r)-3-amino-4-methyloctanoic acid Chemical compound CCCC[C@@H](C)[C@H](N)CC(O)=O WNDLIPKAWDXSDD-HTQZYQBOSA-N 0.000 description 1
- NJVLKMUQIOVNHG-VXNVDRBHSA-N (3r,4r)-3-amino-5-cyclobutyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CC1CCC1 NJVLKMUQIOVNHG-VXNVDRBHSA-N 0.000 description 1
- XMTQHPFMHQFXNI-MWLCHTKSSA-N (3r,4r)-3-amino-5-cyclohexyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CC1CCCCC1 XMTQHPFMHQFXNI-MWLCHTKSSA-N 0.000 description 1
- WRJAYCQSKUFUTM-PSASIEDQSA-N (3r,4r)-3-amino-5-cyclopentyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CC1CCCC1 WRJAYCQSKUFUTM-PSASIEDQSA-N 0.000 description 1
- XRTYNQXCPKXJIG-HTRCEHHLSA-N (3r,4r)-3-amino-5-cyclopropyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CC1CC1 XRTYNQXCPKXJIG-HTRCEHHLSA-N 0.000 description 1
- ZYBPLQLFVXPOOH-PSASIEDQSA-N (3r,4r)-3-amino-6-cyclobutyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCC1CCC1 ZYBPLQLFVXPOOH-PSASIEDQSA-N 0.000 description 1
- XFLLFZLSCBFNJM-ZYHUDNBSSA-N (3r,4r)-3-amino-6-cyclohexyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCC1CCCCC1 XFLLFZLSCBFNJM-ZYHUDNBSSA-N 0.000 description 1
- SNXUUHWDFVBSBX-MWLCHTKSSA-N (3r,4r)-3-amino-6-cyclopentyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCC1CCCC1 SNXUUHWDFVBSBX-MWLCHTKSSA-N 0.000 description 1
- KFCSCIWLWWRJEP-VXNVDRBHSA-N (3r,4r)-3-amino-6-cyclopropyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCC1CC1 KFCSCIWLWWRJEP-VXNVDRBHSA-N 0.000 description 1
- XAAHGONCEDNHFD-MWLCHTKSSA-N (3r,4r)-3-amino-7-cyclobutyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCC1CCC1 XAAHGONCEDNHFD-MWLCHTKSSA-N 0.000 description 1
- VLFUKHVZHCVEHR-DGCLKSJQSA-N (3r,4r)-3-amino-7-cyclohexyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCC1CCCCC1 VLFUKHVZHCVEHR-DGCLKSJQSA-N 0.000 description 1
- UCIBLQOPLARDGY-ZYHUDNBSSA-N (3r,4r)-3-amino-7-cyclopentyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCC1CCCC1 UCIBLQOPLARDGY-ZYHUDNBSSA-N 0.000 description 1
- FCMZYSLCZFHUMM-PSASIEDQSA-N (3r,4r)-3-amino-7-cyclopropyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCC1CC1 FCMZYSLCZFHUMM-PSASIEDQSA-N 0.000 description 1
- QAHWZDQEOABWLW-ZYHUDNBSSA-N (3r,4r)-3-amino-8-cyclobutyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCC1CCC1 QAHWZDQEOABWLW-ZYHUDNBSSA-N 0.000 description 1
- QGSFQQUMVSTMBX-TZMCWYRMSA-N (3r,4r)-3-amino-8-cyclohexyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCC1CCCCC1 QGSFQQUMVSTMBX-TZMCWYRMSA-N 0.000 description 1
- UYSDRJNMTHVXFC-DGCLKSJQSA-N (3r,4r)-3-amino-8-cyclopentyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCC1CCCC1 UYSDRJNMTHVXFC-DGCLKSJQSA-N 0.000 description 1
- CYGNJFPUSKKPGI-MWLCHTKSSA-N (3r,4r)-3-amino-8-cyclopropyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCC1CC1 CYGNJFPUSKKPGI-MWLCHTKSSA-N 0.000 description 1
- IQVRQFLAPNGDDZ-DGCLKSJQSA-N (3r,4r)-3-amino-9-cyclobutyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCCC1CCC1 IQVRQFLAPNGDDZ-DGCLKSJQSA-N 0.000 description 1
- BHHYAIYNLUAWSP-UKRRQHHQSA-N (3r,4r)-3-amino-9-cyclohexyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCCC1CCCCC1 BHHYAIYNLUAWSP-UKRRQHHQSA-N 0.000 description 1
- RVEFLVVMIXKKIR-TZMCWYRMSA-N (3r,4r)-3-amino-9-cyclopentyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCCC1CCCC1 RVEFLVVMIXKKIR-TZMCWYRMSA-N 0.000 description 1
- QGFBHVWGGPHMQU-ZYHUDNBSSA-N (3r,4r)-3-amino-9-cyclopropyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@H](C)CCCCCC1CC1 QGFBHVWGGPHMQU-ZYHUDNBSSA-N 0.000 description 1
- JNILHKVTKKZTKO-NKWVEPMBSA-N (3r,4s)-3-amino-4,5-dimethylhexanoic acid Chemical compound CC(C)[C@H](C)[C@H](N)CC(O)=O JNILHKVTKKZTKO-NKWVEPMBSA-N 0.000 description 1
- NFVLCHFMYBGJHD-JGVFFNPUSA-N (3r,4s)-3-amino-4,6-dimethylheptanoic acid Chemical compound CC(C)C[C@H](C)[C@H](N)CC(O)=O NFVLCHFMYBGJHD-JGVFFNPUSA-N 0.000 description 1
- VLWJBYXEBQRSMA-DTWKUNHWSA-N (3r,4s)-3-amino-4,7-dimethyloctanoic acid Chemical compound CC(C)CC[C@H](C)[C@H](N)CC(O)=O VLWJBYXEBQRSMA-DTWKUNHWSA-N 0.000 description 1
- ULBMATTTZLROEN-VHSXEESVSA-N (3r,4s)-3-amino-4,8-dimethylnonanoic acid Chemical compound CC(C)CCC[C@H](C)[C@H](N)CC(O)=O ULBMATTTZLROEN-VHSXEESVSA-N 0.000 description 1
- OOSQZJATKLDLNT-WDEREUQCSA-N (3r,4s)-3-amino-4,9-dimethyldecanoic acid Chemical compound CC(C)CCCC[C@H](C)[C@H](N)CC(O)=O OOSQZJATKLDLNT-WDEREUQCSA-N 0.000 description 1
- SLWLIZJXWOIOIT-POYBYMJQSA-N (3r,4s)-3-amino-4-cyclobutylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)C1CCC1 SLWLIZJXWOIOIT-POYBYMJQSA-N 0.000 description 1
- CAXPLTIMYMSSQM-WCBMZHEXSA-N (3r,4s)-3-amino-4-cyclohexylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)C1CCCCC1 CAXPLTIMYMSSQM-WCBMZHEXSA-N 0.000 description 1
- BDSFBZHOMCDBGL-IONNQARKSA-N (3r,4s)-3-amino-4-cyclopentylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)C1CCCC1 BDSFBZHOMCDBGL-IONNQARKSA-N 0.000 description 1
- SWPZRWPZRQZIJV-CAHLUQPWSA-N (3r,4s)-3-amino-4-cyclopropylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)C1CC1 SWPZRWPZRQZIJV-CAHLUQPWSA-N 0.000 description 1
- WORUZBFCUXZOHJ-VHSXEESVSA-N (3r,4s)-3-amino-4-methyldecanoic acid Chemical compound CCCCCC[C@H](C)[C@H](N)CC(O)=O WORUZBFCUXZOHJ-VHSXEESVSA-N 0.000 description 1
- KEZZGIFSTDSATA-DTWKUNHWSA-N (3r,4s)-3-amino-4-methylnonanoic acid Chemical compound CCCCC[C@H](C)[C@H](N)CC(O)=O KEZZGIFSTDSATA-DTWKUNHWSA-N 0.000 description 1
- WNDLIPKAWDXSDD-JGVFFNPUSA-N (3r,4s)-3-amino-4-methyloctanoic acid Chemical compound CCCC[C@H](C)[C@H](N)CC(O)=O WNDLIPKAWDXSDD-JGVFFNPUSA-N 0.000 description 1
- NJVLKMUQIOVNHG-IONNQARKSA-N (3r,4s)-3-amino-5-cyclobutyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CC1CCC1 NJVLKMUQIOVNHG-IONNQARKSA-N 0.000 description 1
- XMTQHPFMHQFXNI-GXSJLCMTSA-N (3r,4s)-3-amino-5-cyclohexyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CC1CCCCC1 XMTQHPFMHQFXNI-GXSJLCMTSA-N 0.000 description 1
- WRJAYCQSKUFUTM-WCBMZHEXSA-N (3r,4s)-3-amino-5-cyclopentyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CC1CCCC1 WRJAYCQSKUFUTM-WCBMZHEXSA-N 0.000 description 1
- XRTYNQXCPKXJIG-POYBYMJQSA-N (3r,4s)-3-amino-5-cyclopropyl-4-methylpentanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CC1CC1 XRTYNQXCPKXJIG-POYBYMJQSA-N 0.000 description 1
- ZYBPLQLFVXPOOH-WCBMZHEXSA-N (3r,4s)-3-amino-6-cyclobutyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCC1CCC1 ZYBPLQLFVXPOOH-WCBMZHEXSA-N 0.000 description 1
- XFLLFZLSCBFNJM-CMPLNLGQSA-N (3r,4s)-3-amino-6-cyclohexyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCC1CCCCC1 XFLLFZLSCBFNJM-CMPLNLGQSA-N 0.000 description 1
- SNXUUHWDFVBSBX-GXSJLCMTSA-N (3r,4s)-3-amino-6-cyclopentyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCC1CCCC1 SNXUUHWDFVBSBX-GXSJLCMTSA-N 0.000 description 1
- KFCSCIWLWWRJEP-IONNQARKSA-N (3r,4s)-3-amino-6-cyclopropyl-4-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCC1CC1 KFCSCIWLWWRJEP-IONNQARKSA-N 0.000 description 1
- XAAHGONCEDNHFD-GXSJLCMTSA-N (3r,4s)-3-amino-7-cyclobutyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCC1CCC1 XAAHGONCEDNHFD-GXSJLCMTSA-N 0.000 description 1
- VLFUKHVZHCVEHR-WCQYABFASA-N (3r,4s)-3-amino-7-cyclohexyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCC1CCCCC1 VLFUKHVZHCVEHR-WCQYABFASA-N 0.000 description 1
- UCIBLQOPLARDGY-CMPLNLGQSA-N (3r,4s)-3-amino-7-cyclopentyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCC1CCCC1 UCIBLQOPLARDGY-CMPLNLGQSA-N 0.000 description 1
- FCMZYSLCZFHUMM-WCBMZHEXSA-N (3r,4s)-3-amino-7-cyclopropyl-4-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCC1CC1 FCMZYSLCZFHUMM-WCBMZHEXSA-N 0.000 description 1
- QAHWZDQEOABWLW-CMPLNLGQSA-N (3r,4s)-3-amino-8-cyclobutyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCC1CCC1 QAHWZDQEOABWLW-CMPLNLGQSA-N 0.000 description 1
- QGSFQQUMVSTMBX-GXTWGEPZSA-N (3r,4s)-3-amino-8-cyclohexyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCC1CCCCC1 QGSFQQUMVSTMBX-GXTWGEPZSA-N 0.000 description 1
- UYSDRJNMTHVXFC-WCQYABFASA-N (3r,4s)-3-amino-8-cyclopentyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCC1CCCC1 UYSDRJNMTHVXFC-WCQYABFASA-N 0.000 description 1
- CYGNJFPUSKKPGI-GXSJLCMTSA-N (3r,4s)-3-amino-8-cyclopropyl-4-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCC1CC1 CYGNJFPUSKKPGI-GXSJLCMTSA-N 0.000 description 1
- IQVRQFLAPNGDDZ-WCQYABFASA-N (3r,4s)-3-amino-9-cyclobutyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCCC1CCC1 IQVRQFLAPNGDDZ-WCQYABFASA-N 0.000 description 1
- BHHYAIYNLUAWSP-DZGCQCFKSA-N (3r,4s)-3-amino-9-cyclohexyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCCC1CCCCC1 BHHYAIYNLUAWSP-DZGCQCFKSA-N 0.000 description 1
- RVEFLVVMIXKKIR-GXTWGEPZSA-N (3r,4s)-3-amino-9-cyclopentyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCCC1CCCC1 RVEFLVVMIXKKIR-GXTWGEPZSA-N 0.000 description 1
- QGFBHVWGGPHMQU-CMPLNLGQSA-N (3r,4s)-3-amino-9-cyclopropyl-4-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)[C@@H](C)CCCCCC1CC1 QGFBHVWGGPHMQU-CMPLNLGQSA-N 0.000 description 1
- IULIQVOUARZGOO-MRVPVSSYSA-N (3s)-3-amino-5,5,6-trimethylheptanoic acid Chemical compound CC(C)C(C)(C)C[C@H](N)CC(O)=O IULIQVOUARZGOO-MRVPVSSYSA-N 0.000 description 1
- LCGCZVFEWKPKBQ-SECBINFHSA-N (3s)-3-amino-5,5,7-trimethyloctanoic acid Chemical compound CC(C)CC(C)(C)C[C@H](N)CC(O)=O LCGCZVFEWKPKBQ-SECBINFHSA-N 0.000 description 1
- HEQORWISLIFIOP-SNVBAGLBSA-N (3s)-3-amino-5,5,8-trimethylnonanoic acid Chemical compound CC(C)CCC(C)(C)C[C@H](N)CC(O)=O HEQORWISLIFIOP-SNVBAGLBSA-N 0.000 description 1
- TXMGNOBMAKSFLA-LLVKDONJSA-N (3s)-3-amino-5,5,9-trimethyldecanoic acid Chemical compound CC(C)CCCC(C)(C)C[C@H](N)CC(O)=O TXMGNOBMAKSFLA-LLVKDONJSA-N 0.000 description 1
- OLDZNUWFLJMUJG-SSDOTTSWSA-N (3s)-3-amino-5,5-dimethylheptanoic acid Chemical compound CCC(C)(C)C[C@H](N)CC(O)=O OLDZNUWFLJMUJG-SSDOTTSWSA-N 0.000 description 1
- ZRZSRUFSARPSBU-DDWIOCJRSA-N (3s)-3-amino-5,5-dimethyloctanoic acid;hydrochloride Chemical compound Cl.CCCC(C)(C)C[C@H](N)CC(O)=O ZRZSRUFSARPSBU-DDWIOCJRSA-N 0.000 description 1
- ITMYONXPNKXDII-ZJUUUORDSA-N (3s,5r)-3-amino-5,8-dimethylnonanoic acid Chemical compound CC(C)CC[C@@H](C)C[C@H](N)CC(O)=O ITMYONXPNKXDII-ZJUUUORDSA-N 0.000 description 1
- ZWYUMQOOBJZKIM-DOMZBBRYSA-N (3s,5r)-3-amino-5-methyl-8-(2-methylphenyl)octanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=CC=C1C ZWYUMQOOBJZKIM-DOMZBBRYSA-N 0.000 description 1
- DYEVZBGHLDTBNR-HIFRSBDPSA-N (3s,5r)-3-amino-5-methyl-8-(3-methylphenyl)octanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=CC(C)=C1 DYEVZBGHLDTBNR-HIFRSBDPSA-N 0.000 description 1
- DUYFASMCTHELDM-HIFRSBDPSA-N (3s,5r)-3-amino-5-methyl-8-(4-methylphenyl)octanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=C(C)C=C1 DUYFASMCTHELDM-HIFRSBDPSA-N 0.000 description 1
- JJDVRTVXSKENRP-OCCSQVGLSA-N (3s,5r)-3-amino-5-methyl-8-phenyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=CC=C1 JJDVRTVXSKENRP-OCCSQVGLSA-N 0.000 description 1
- JWFAQHHLVSZYBE-ZJUUUORDSA-N (3s,5r)-3-amino-5-methyldecanoic acid Chemical compound CCCCC[C@@H](C)C[C@H](N)CC(O)=O JWFAQHHLVSZYBE-ZJUUUORDSA-N 0.000 description 1
- SNVUCYHKFWMKAK-HHQFNNIRSA-N (3s,5r)-3-amino-5-methylheptanoic acid;hydrochloride Chemical compound Cl.CC[C@@H](C)C[C@H](N)CC(O)=O SNVUCYHKFWMKAK-HHQFNNIRSA-N 0.000 description 1
- HPBIXKQDDMOTDK-JROBTXBMSA-N (3s,5r)-3-amino-5-methyloctanoic acid;(6r)-2,6-dimethylnon-2-ene;hydrochloride Chemical compound Cl.CCC[C@@H](C)CCC=C(C)C.CCC[C@@H](C)C[C@H](N)CC(O)=O HPBIXKQDDMOTDK-JROBTXBMSA-N 0.000 description 1
- MPFUZQRZDJJIGX-MNOVXSKESA-N (3s,5r)-3-amino-6-anilino-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CNC1=CC=CC=C1 MPFUZQRZDJJIGX-MNOVXSKESA-N 0.000 description 1
- VHHISCCVQDCXRI-PWSUYJOCSA-N (3s,5r)-3-amino-6-cyclohexyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CC1CCCCC1 VHHISCCVQDCXRI-PWSUYJOCSA-N 0.000 description 1
- UFBOLJVGIKJODE-KOLCDFICSA-N (3s,5r)-3-amino-6-cyclopentyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CC1CCCC1 UFBOLJVGIKJODE-KOLCDFICSA-N 0.000 description 1
- VZGDFJXPUUUDRO-APPZFPTMSA-N (3s,5r)-3-amino-6-cyclopropyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CC1CC1 VZGDFJXPUUUDRO-APPZFPTMSA-N 0.000 description 1
- XWNWLFBIMCWZGL-NEPJUHHUSA-N (3s,5r)-3-amino-7-anilino-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCNC1=CC=CC=C1 XWNWLFBIMCWZGL-NEPJUHHUSA-N 0.000 description 1
- FRXVVOBOAUAOCA-PWSUYJOCSA-N (3s,5r)-3-amino-8-(2,3-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=CC(F)=C1F FRXVVOBOAUAOCA-PWSUYJOCSA-N 0.000 description 1
- WXJZPMQTLWNDGI-MFKMUULPSA-N (3s,5r)-3-amino-8-(2,4-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=C(F)C=C1F WXJZPMQTLWNDGI-MFKMUULPSA-N 0.000 description 1
- BJJUWJRHAOZTDS-MFKMUULPSA-N (3s,5r)-3-amino-8-(2,5-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC(F)=CC=C1F BJJUWJRHAOZTDS-MFKMUULPSA-N 0.000 description 1
- IGEGKZVQKNVMQW-MNOVXSKESA-N (3s,5r)-3-amino-8-(2,6-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=C(F)C=CC=C1F IGEGKZVQKNVMQW-MNOVXSKESA-N 0.000 description 1
- OHWKTBIGJBCPHA-YPMHNXCESA-N (3s,5r)-3-amino-8-(2-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=CC=C1F OHWKTBIGJBCPHA-YPMHNXCESA-N 0.000 description 1
- WRUFUMYBJOJYKF-RISCZKNCSA-N (3s,5r)-3-amino-8-(3-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=CC(F)=C1 WRUFUMYBJOJYKF-RISCZKNCSA-N 0.000 description 1
- IXVWSDRHSNWDRR-RISCZKNCSA-N (3s,5r)-3-amino-8-(4-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCC1=CC=C(F)C=C1 IXVWSDRHSNWDRR-RISCZKNCSA-N 0.000 description 1
- OFZJJHYIDMIOBI-OLZOCXBDSA-N (3s,5r)-3-amino-8-anilino-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CCCNC1=CC=CC=C1 OFZJJHYIDMIOBI-OLZOCXBDSA-N 0.000 description 1
- KUDCOPNNXKGLPZ-OCCSQVGLSA-N (3s,5r)-5-methyl-3-(phenylmethoxycarbonylamino)heptanoic acid Chemical compound CC[C@@H](C)C[C@@H](CC(O)=O)NC(=O)OCC1=CC=CC=C1 KUDCOPNNXKGLPZ-OCCSQVGLSA-N 0.000 description 1
- ITMYONXPNKXDII-UWVGGRQHSA-N (3s,5s)-3-amino-5,8-dimethylnonanoic acid Chemical compound CC(C)CC[C@H](C)C[C@H](N)CC(O)=O ITMYONXPNKXDII-UWVGGRQHSA-N 0.000 description 1
- ZWYUMQOOBJZKIM-WFASDCNBSA-N (3s,5s)-3-amino-5-methyl-8-(2-methylphenyl)octanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=CC=C1C ZWYUMQOOBJZKIM-WFASDCNBSA-N 0.000 description 1
- DYEVZBGHLDTBNR-ZFWWWQNUSA-N (3s,5s)-3-amino-5-methyl-8-(3-methylphenyl)octanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=CC(C)=C1 DYEVZBGHLDTBNR-ZFWWWQNUSA-N 0.000 description 1
- DUYFASMCTHELDM-ZFWWWQNUSA-N (3s,5s)-3-amino-5-methyl-8-(4-methylphenyl)octanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=C(C)C=C1 DUYFASMCTHELDM-ZFWWWQNUSA-N 0.000 description 1
- JJDVRTVXSKENRP-JSGCOSHPSA-N (3s,5s)-3-amino-5-methyl-8-phenyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=CC=C1 JJDVRTVXSKENRP-JSGCOSHPSA-N 0.000 description 1
- JWFAQHHLVSZYBE-UWVGGRQHSA-N (3s,5s)-3-amino-5-methyldecanoic acid Chemical compound CCCCC[C@H](C)C[C@H](N)CC(O)=O JWFAQHHLVSZYBE-UWVGGRQHSA-N 0.000 description 1
- GUEQOLSQPOTTME-BQBZGAKWSA-N (3s,5s)-3-amino-5-methylheptanoic acid Chemical compound CC[C@H](C)C[C@H](N)CC(O)=O GUEQOLSQPOTTME-BQBZGAKWSA-N 0.000 description 1
- XKWDZEJCUWTBOM-IUCAKERBSA-N (3s,5s)-3-amino-5-methylnonanoic acid Chemical compound CCCC[C@H](C)C[C@H](N)CC(O)=O XKWDZEJCUWTBOM-IUCAKERBSA-N 0.000 description 1
- MPFUZQRZDJJIGX-QWRGUYRKSA-N (3s,5s)-3-amino-6-anilino-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@H](C)CNC1=CC=CC=C1 MPFUZQRZDJJIGX-QWRGUYRKSA-N 0.000 description 1
- VHHISCCVQDCXRI-JQWIXIFHSA-N (3s,5s)-3-amino-6-cyclohexyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CC1CCCCC1 VHHISCCVQDCXRI-JQWIXIFHSA-N 0.000 description 1
- UFBOLJVGIKJODE-ONGXEEELSA-N (3s,5s)-3-amino-6-cyclopentyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CC1CCCC1 UFBOLJVGIKJODE-ONGXEEELSA-N 0.000 description 1
- VZGDFJXPUUUDRO-CBAPKCEASA-N (3s,5s)-3-amino-6-cyclopropyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CC1CC1 VZGDFJXPUUUDRO-CBAPKCEASA-N 0.000 description 1
- XWNWLFBIMCWZGL-RYUDHWBXSA-N (3s,5s)-3-amino-7-anilino-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCNC1=CC=CC=C1 XWNWLFBIMCWZGL-RYUDHWBXSA-N 0.000 description 1
- FRXVVOBOAUAOCA-JQWIXIFHSA-N (3s,5s)-3-amino-8-(2,3-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=CC(F)=C1F FRXVVOBOAUAOCA-JQWIXIFHSA-N 0.000 description 1
- WXJZPMQTLWNDGI-GWCFXTLKSA-N (3s,5s)-3-amino-8-(2,4-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=C(F)C=C1F WXJZPMQTLWNDGI-GWCFXTLKSA-N 0.000 description 1
- BJJUWJRHAOZTDS-GWCFXTLKSA-N (3s,5s)-3-amino-8-(2,5-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC(F)=CC=C1F BJJUWJRHAOZTDS-GWCFXTLKSA-N 0.000 description 1
- OHWKTBIGJBCPHA-AAEUAGOBSA-N (3s,5s)-3-amino-8-(2-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=CC=C1F OHWKTBIGJBCPHA-AAEUAGOBSA-N 0.000 description 1
- WRUFUMYBJOJYKF-FZMZJTMJSA-N (3s,5s)-3-amino-8-(3-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=CC(F)=C1 WRUFUMYBJOJYKF-FZMZJTMJSA-N 0.000 description 1
- IXVWSDRHSNWDRR-FZMZJTMJSA-N (3s,5s)-3-amino-8-(4-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCC1=CC=C(F)C=C1 IXVWSDRHSNWDRR-FZMZJTMJSA-N 0.000 description 1
- OFZJJHYIDMIOBI-STQMWFEESA-N (3s,5s)-3-amino-8-anilino-5-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)C[C@@H](C)CCCNC1=CC=CC=C1 OFZJJHYIDMIOBI-STQMWFEESA-N 0.000 description 1
- SVNJVCBZYCFWKE-OCCSQVGLSA-N (3s,6r)-3-amino-10-cyclobutyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCCC1CCC1 SVNJVCBZYCFWKE-OCCSQVGLSA-N 0.000 description 1
- VNWHXNIIPFGSIN-ZBFHGGJFSA-N (3s,6r)-3-amino-10-cyclohexyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCCC1CCCCC1 VNWHXNIIPFGSIN-ZBFHGGJFSA-N 0.000 description 1
- SGYHTWYIEHBCMI-HIFRSBDPSA-N (3s,6r)-3-amino-10-cyclopentyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCCC1CCCC1 SGYHTWYIEHBCMI-HIFRSBDPSA-N 0.000 description 1
- HTDBTBIKBIFJMW-YPMHNXCESA-N (3s,6r)-3-amino-10-cyclopropyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCCC1CC1 HTDBTBIKBIFJMW-YPMHNXCESA-N 0.000 description 1
- KDLUWSRUCDCRJD-BDAKNGLRSA-N (3s,6r)-3-amino-6,7-dimethyloctanoic acid Chemical compound CC(C)[C@H](C)CC[C@H](N)CC(O)=O KDLUWSRUCDCRJD-BDAKNGLRSA-N 0.000 description 1
- LVFHFOOXOPYZJV-ZJUUUORDSA-N (3s,6r)-3-amino-6,8-dimethylnonanoic acid Chemical compound CC(C)C[C@H](C)CC[C@H](N)CC(O)=O LVFHFOOXOPYZJV-ZJUUUORDSA-N 0.000 description 1
- POYVFGYVTDVXAL-MNOVXSKESA-N (3s,6r)-3-amino-6,9-dimethyldecanoic acid Chemical compound CC(C)CC[C@@H](C)CC[C@H](N)CC(O)=O POYVFGYVTDVXAL-MNOVXSKESA-N 0.000 description 1
- QXAPPVCMDBQCQV-SCZZXKLOSA-N (3s,6r)-3-amino-6-cyclobutylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)C1CCC1 QXAPPVCMDBQCQV-SCZZXKLOSA-N 0.000 description 1
- QIANTAAMZOBXPN-PWSUYJOCSA-N (3s,6r)-3-amino-6-cyclohexylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)C1CCCCC1 QIANTAAMZOBXPN-PWSUYJOCSA-N 0.000 description 1
- IMMNOOJXDKHOOA-KOLCDFICSA-N (3s,6r)-3-amino-6-cyclopentylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)C1CCCC1 IMMNOOJXDKHOOA-KOLCDFICSA-N 0.000 description 1
- OSMIIIZIDCILLJ-APPZFPTMSA-N (3s,6r)-3-amino-6-cyclopropylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)C1CC1 OSMIIIZIDCILLJ-APPZFPTMSA-N 0.000 description 1
- UQMJIFBIWYTIII-ZJUUUORDSA-N (3s,6r)-3-amino-6-methyldecanoic acid Chemical compound CCCC[C@@H](C)CC[C@H](N)CC(O)=O UQMJIFBIWYTIII-ZJUUUORDSA-N 0.000 description 1
- BEVWNYGYKVWLPQ-KOLCDFICSA-N (3s,6r)-3-amino-7-cyclobutyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CC1CCC1 BEVWNYGYKVWLPQ-KOLCDFICSA-N 0.000 description 1
- ZDQUKINEHXVJRF-YPMHNXCESA-N (3s,6r)-3-amino-7-cyclohexyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CC1CCCCC1 ZDQUKINEHXVJRF-YPMHNXCESA-N 0.000 description 1
- UHXZGUXGDOJBGD-PWSUYJOCSA-N (3s,6r)-3-amino-7-cyclopentyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CC1CCCC1 UHXZGUXGDOJBGD-PWSUYJOCSA-N 0.000 description 1
- DJKRRSBCJCGREA-SCZZXKLOSA-N (3s,6r)-3-amino-7-cyclopropyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CC1CC1 DJKRRSBCJCGREA-SCZZXKLOSA-N 0.000 description 1
- WMXQQGVTDZLYLJ-PWSUYJOCSA-N (3s,6r)-3-amino-8-cyclobutyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCC1CCC1 WMXQQGVTDZLYLJ-PWSUYJOCSA-N 0.000 description 1
- AHHLMWKLWUYOQH-OCCSQVGLSA-N (3s,6r)-3-amino-8-cyclohexyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCC1CCCCC1 AHHLMWKLWUYOQH-OCCSQVGLSA-N 0.000 description 1
- LVMANRYTMRTWNA-YPMHNXCESA-N (3s,6r)-3-amino-8-cyclopentyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCC1CCCC1 LVMANRYTMRTWNA-YPMHNXCESA-N 0.000 description 1
- SBFUHNDWSDWPNV-KOLCDFICSA-N (3s,6r)-3-amino-8-cyclopropyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCC1CC1 SBFUHNDWSDWPNV-KOLCDFICSA-N 0.000 description 1
- XEDARUVJQRFVGB-YPMHNXCESA-N (3s,6r)-3-amino-9-cyclobutyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCC1CCC1 XEDARUVJQRFVGB-YPMHNXCESA-N 0.000 description 1
- JUKPMBVQCZNQNA-HIFRSBDPSA-N (3s,6r)-3-amino-9-cyclohexyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCC1CCCCC1 JUKPMBVQCZNQNA-HIFRSBDPSA-N 0.000 description 1
- QJTBKRLAAAKINB-OCCSQVGLSA-N (3s,6r)-3-amino-9-cyclopentyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCC1CCCC1 QJTBKRLAAAKINB-OCCSQVGLSA-N 0.000 description 1
- BQRPWAJQPDMQRX-PWSUYJOCSA-N (3s,6r)-3-amino-9-cyclopropyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CCCC1CC1 BQRPWAJQPDMQRX-PWSUYJOCSA-N 0.000 description 1
- SVNJVCBZYCFWKE-JSGCOSHPSA-N (3s,6s)-3-amino-10-cyclobutyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCCC1CCC1 SVNJVCBZYCFWKE-JSGCOSHPSA-N 0.000 description 1
- VNWHXNIIPFGSIN-HOCLYGCPSA-N (3s,6s)-3-amino-10-cyclohexyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCCC1CCCCC1 VNWHXNIIPFGSIN-HOCLYGCPSA-N 0.000 description 1
- SGYHTWYIEHBCMI-ZFWWWQNUSA-N (3s,6s)-3-amino-10-cyclopentyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCCC1CCCC1 SGYHTWYIEHBCMI-ZFWWWQNUSA-N 0.000 description 1
- HTDBTBIKBIFJMW-AAEUAGOBSA-N (3s,6s)-3-amino-10-cyclopropyl-6-methyldecanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCCC1CC1 HTDBTBIKBIFJMW-AAEUAGOBSA-N 0.000 description 1
- KDLUWSRUCDCRJD-IUCAKERBSA-N (3s,6s)-3-amino-6,7-dimethyloctanoic acid Chemical compound CC(C)[C@@H](C)CC[C@H](N)CC(O)=O KDLUWSRUCDCRJD-IUCAKERBSA-N 0.000 description 1
- LVFHFOOXOPYZJV-UWVGGRQHSA-N (3s,6s)-3-amino-6,8-dimethylnonanoic acid Chemical compound CC(C)C[C@@H](C)CC[C@H](N)CC(O)=O LVFHFOOXOPYZJV-UWVGGRQHSA-N 0.000 description 1
- POYVFGYVTDVXAL-QWRGUYRKSA-N (3s,6s)-3-amino-6,9-dimethyldecanoic acid Chemical compound CC(C)CC[C@H](C)CC[C@H](N)CC(O)=O POYVFGYVTDVXAL-QWRGUYRKSA-N 0.000 description 1
- QXAPPVCMDBQCQV-WPRPVWTQSA-N (3s,6s)-3-amino-6-cyclobutylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)C1CCC1 QXAPPVCMDBQCQV-WPRPVWTQSA-N 0.000 description 1
- QIANTAAMZOBXPN-JQWIXIFHSA-N (3s,6s)-3-amino-6-cyclohexylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)C1CCCCC1 QIANTAAMZOBXPN-JQWIXIFHSA-N 0.000 description 1
- IMMNOOJXDKHOOA-ONGXEEELSA-N (3s,6s)-3-amino-6-cyclopentylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)C1CCCC1 IMMNOOJXDKHOOA-ONGXEEELSA-N 0.000 description 1
- OSMIIIZIDCILLJ-CBAPKCEASA-N (3s,6s)-3-amino-6-cyclopropylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)C1CC1 OSMIIIZIDCILLJ-CBAPKCEASA-N 0.000 description 1
- UQMJIFBIWYTIII-UWVGGRQHSA-N (3s,6s)-3-amino-6-methyldecanoic acid Chemical compound CCCC[C@H](C)CC[C@H](N)CC(O)=O UQMJIFBIWYTIII-UWVGGRQHSA-N 0.000 description 1
- IKQZOPMCFWMWNY-IUCAKERBSA-N (3s,6s)-3-amino-6-methylnonanoic acid Chemical compound CCC[C@H](C)CC[C@H](N)CC(O)=O IKQZOPMCFWMWNY-IUCAKERBSA-N 0.000 description 1
- JJYQLFRIPYECNB-YUMQZZPRSA-N (3s,6s)-3-amino-6-methyloctanoic acid Chemical compound CC[C@H](C)CC[C@H](N)CC(O)=O JJYQLFRIPYECNB-YUMQZZPRSA-N 0.000 description 1
- BEVWNYGYKVWLPQ-ONGXEEELSA-N (3s,6s)-3-amino-7-cyclobutyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CC1CCC1 BEVWNYGYKVWLPQ-ONGXEEELSA-N 0.000 description 1
- ZDQUKINEHXVJRF-AAEUAGOBSA-N (3s,6s)-3-amino-7-cyclohexyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CC1CCCCC1 ZDQUKINEHXVJRF-AAEUAGOBSA-N 0.000 description 1
- UHXZGUXGDOJBGD-JQWIXIFHSA-N (3s,6s)-3-amino-7-cyclopentyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CC1CCCC1 UHXZGUXGDOJBGD-JQWIXIFHSA-N 0.000 description 1
- DJKRRSBCJCGREA-WPRPVWTQSA-N (3s,6s)-3-amino-7-cyclopropyl-6-methylheptanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@H](C)CC1CC1 DJKRRSBCJCGREA-WPRPVWTQSA-N 0.000 description 1
- WMXQQGVTDZLYLJ-JQWIXIFHSA-N (3s,6s)-3-amino-8-cyclobutyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCC1CCC1 WMXQQGVTDZLYLJ-JQWIXIFHSA-N 0.000 description 1
- AHHLMWKLWUYOQH-JSGCOSHPSA-N (3s,6s)-3-amino-8-cyclohexyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCC1CCCCC1 AHHLMWKLWUYOQH-JSGCOSHPSA-N 0.000 description 1
- LVMANRYTMRTWNA-AAEUAGOBSA-N (3s,6s)-3-amino-8-cyclopentyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCC1CCCC1 LVMANRYTMRTWNA-AAEUAGOBSA-N 0.000 description 1
- SBFUHNDWSDWPNV-ONGXEEELSA-N (3s,6s)-3-amino-8-cyclopropyl-6-methyloctanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCC1CC1 SBFUHNDWSDWPNV-ONGXEEELSA-N 0.000 description 1
- XEDARUVJQRFVGB-AAEUAGOBSA-N (3s,6s)-3-amino-9-cyclobutyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCC1CCC1 XEDARUVJQRFVGB-AAEUAGOBSA-N 0.000 description 1
- JUKPMBVQCZNQNA-ZFWWWQNUSA-N (3s,6s)-3-amino-9-cyclohexyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCC1CCCCC1 JUKPMBVQCZNQNA-ZFWWWQNUSA-N 0.000 description 1
- QJTBKRLAAAKINB-JSGCOSHPSA-N (3s,6s)-3-amino-9-cyclopentyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCC1CCCC1 QJTBKRLAAAKINB-JSGCOSHPSA-N 0.000 description 1
- BQRPWAJQPDMQRX-JQWIXIFHSA-N (3s,6s)-3-amino-9-cyclopropyl-6-methylnonanoic acid Chemical compound OC(=O)C[C@@H](N)CC[C@@H](C)CCCC1CC1 BQRPWAJQPDMQRX-JQWIXIFHSA-N 0.000 description 1
- OJOFMLDBXPDXLQ-SECBINFHSA-N (4r)-4-benzyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@@H]1CC1=CC=CC=C1 OJOFMLDBXPDXLQ-SECBINFHSA-N 0.000 description 1
- DIVCBWJKVSFZKJ-ZCFIWIBFSA-N (4r)-4-methylhexanoic acid Chemical compound CC[C@@H](C)CCC(O)=O DIVCBWJKVSFZKJ-ZCFIWIBFSA-N 0.000 description 1
- LEGGANXCVQPIAI-MRVPVSSYSA-N (4r)-4-methyloctanoic acid Chemical compound CCCC[C@@H](C)CCC(O)=O LEGGANXCVQPIAI-MRVPVSSYSA-N 0.000 description 1
- YBUPWRYTXGAWJX-YFKPBYRVSA-N (4r)-4-propan-2-yl-1,3-oxazolidin-2-one Chemical compound CC(C)[C@@H]1COC(=O)N1 YBUPWRYTXGAWJX-YFKPBYRVSA-N 0.000 description 1
- GJOBEUUSTJWCJF-XJKCOSOUSA-N (4r,5s)-4-methyl-3-[(4r)-4-methylhexanoyl]-5-phenyl-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(C(=O)CC[C@H](C)CC)[C@H](C)[C@@H]1C1=CC=CC=C1 GJOBEUUSTJWCJF-XJKCOSOUSA-N 0.000 description 1
- OJOFMLDBXPDXLQ-VIFPVBQESA-N (4s)-4-benzyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@H]1CC1=CC=CC=C1 OJOFMLDBXPDXLQ-VIFPVBQESA-N 0.000 description 1
- QDMNNMIOWVJVLY-MRVPVSSYSA-N (4s)-4-phenyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@H]1C1=CC=CC=C1 QDMNNMIOWVJVLY-MRVPVSSYSA-N 0.000 description 1
- YBUPWRYTXGAWJX-RXMQYKEDSA-N (4s)-4-propan-2-yl-1,3-oxazolidin-2-one Chemical compound CC(C)[C@H]1COC(=O)N1 YBUPWRYTXGAWJX-RXMQYKEDSA-N 0.000 description 1
- LQBNCHMAPJGDKP-YOEHRIQHSA-N (4s,5r)-3-(4,4-dimethylheptanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(C(=O)CCC(C)(C)CCC)[C@@H](C)[C@H]1C1=CC=CC=C1 LQBNCHMAPJGDKP-YOEHRIQHSA-N 0.000 description 1
- PPIBJOQGAJBQDF-CBAPKCEASA-N (4s,5r)-4-methyl-5-phenyl-1,3-oxazolidin-2-one Chemical compound C[C@@H]1NC(=O)O[C@@H]1C1=CC=CC=C1 PPIBJOQGAJBQDF-CBAPKCEASA-N 0.000 description 1
- WQNLWKDARWVSKE-SNVBAGLBSA-N (6r)-2,6-dimethyloct-2-ene Chemical compound CC[C@@H](C)CCC=C(C)C WQNLWKDARWVSKE-SNVBAGLBSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- GJYMQFMQRRNLCY-BHYDHMSTSA-N (e,2s)-pent-3-en-2-ol Chemical compound C\C=C\[C@H](C)O GJYMQFMQRRNLCY-BHYDHMSTSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- KHNRCDHEOHOYFY-UHFFFAOYSA-N 1-iodo-4-methylpentane Chemical compound CC(C)CCCI KHNRCDHEOHOYFY-UHFFFAOYSA-N 0.000 description 1
- DXSDIWHOOOBQTJ-UHFFFAOYSA-N 2,2-dimethylpent-4-enal Chemical compound O=CC(C)(C)CC=C DXSDIWHOOOBQTJ-UHFFFAOYSA-N 0.000 description 1
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- MZVYPPMRVNDFHO-UHFFFAOYSA-N 2-(aminomethyl)-4,4-dimethylheptanoic acid;hydrochloride Chemical compound Cl.CCCC(C)(C)CC(CN)C(O)=O MZVYPPMRVNDFHO-UHFFFAOYSA-N 0.000 description 1
- AYBAQLFXIAUSSP-YYVQYPFISA-N 2-(aminomethyl)-4,8-dimethylnonanoic acid (2R)-2,6-dimethylheptan-1-ol Chemical compound C[C@@H](CO)CCCC(C)C.NCC(C(=O)O)CC(CCCC(C)C)C AYBAQLFXIAUSSP-YYVQYPFISA-N 0.000 description 1
- LPWDLGDEXYXAOD-UHFFFAOYSA-N 2-(aminomethyl)-4-propylheptanoic acid Chemical compound CCCC(CCC)CC(CN)C(O)=O LPWDLGDEXYXAOD-UHFFFAOYSA-N 0.000 description 1
- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
- JNSSVMGPTZYYIW-UHFFFAOYSA-N 2-chloro-6-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=CC(Cl)=[N+]1[O-] JNSSVMGPTZYYIW-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
- LQBNCHMAPJGDKP-UHFFFAOYSA-N 3-(4,4-dimethylheptanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(C(=O)CCC(C)(C)CCC)C(C)C1C1=CC=CC=C1 LQBNCHMAPJGDKP-UHFFFAOYSA-N 0.000 description 1
- SVNJVCBZYCFWKE-UHFFFAOYSA-N 3-amino-10-cyclobutyl-6-methyldecanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCCC1CCC1 SVNJVCBZYCFWKE-UHFFFAOYSA-N 0.000 description 1
- VNWHXNIIPFGSIN-UHFFFAOYSA-N 3-amino-10-cyclohexyl-6-methyldecanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCCC1CCCCC1 VNWHXNIIPFGSIN-UHFFFAOYSA-N 0.000 description 1
- SGYHTWYIEHBCMI-UHFFFAOYSA-N 3-amino-10-cyclopentyl-6-methyldecanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCCC1CCCC1 SGYHTWYIEHBCMI-UHFFFAOYSA-N 0.000 description 1
- HTDBTBIKBIFJMW-UHFFFAOYSA-N 3-amino-10-cyclopropyl-6-methyldecanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCCC1CC1 HTDBTBIKBIFJMW-UHFFFAOYSA-N 0.000 description 1
- JNILHKVTKKZTKO-UHFFFAOYSA-N 3-amino-4,5-dimethylhexanoic acid Chemical compound CC(C)C(C)C(N)CC(O)=O JNILHKVTKKZTKO-UHFFFAOYSA-N 0.000 description 1
- NFVLCHFMYBGJHD-UHFFFAOYSA-N 3-amino-4,6-dimethylheptanoic acid Chemical compound CC(C)CC(C)C(N)CC(O)=O NFVLCHFMYBGJHD-UHFFFAOYSA-N 0.000 description 1
- VLWJBYXEBQRSMA-UHFFFAOYSA-N 3-amino-4,7-dimethyloctanoic acid Chemical compound CC(C)CCC(C)C(N)CC(O)=O VLWJBYXEBQRSMA-UHFFFAOYSA-N 0.000 description 1
- ULBMATTTZLROEN-UHFFFAOYSA-N 3-amino-4,8-dimethylnonanoic acid Chemical compound CC(C)CCCC(C)C(N)CC(O)=O ULBMATTTZLROEN-UHFFFAOYSA-N 0.000 description 1
- OOSQZJATKLDLNT-UHFFFAOYSA-N 3-amino-4,9-dimethyldecanoic acid Chemical compound CC(C)CCCCC(C)C(N)CC(O)=O OOSQZJATKLDLNT-UHFFFAOYSA-N 0.000 description 1
- SLWLIZJXWOIOIT-UHFFFAOYSA-N 3-amino-4-cyclobutylpentanoic acid Chemical compound OC(=O)CC(N)C(C)C1CCC1 SLWLIZJXWOIOIT-UHFFFAOYSA-N 0.000 description 1
- CAXPLTIMYMSSQM-UHFFFAOYSA-N 3-amino-4-cyclohexylpentanoic acid Chemical compound OC(=O)CC(N)C(C)C1CCCCC1 CAXPLTIMYMSSQM-UHFFFAOYSA-N 0.000 description 1
- BDSFBZHOMCDBGL-UHFFFAOYSA-N 3-amino-4-cyclopentylpentanoic acid Chemical compound OC(=O)CC(N)C(C)C1CCCC1 BDSFBZHOMCDBGL-UHFFFAOYSA-N 0.000 description 1
- SWPZRWPZRQZIJV-UHFFFAOYSA-N 3-amino-4-cyclopropylpentanoic acid Chemical compound OC(=O)CC(N)C(C)C1CC1 SWPZRWPZRQZIJV-UHFFFAOYSA-N 0.000 description 1
- WORUZBFCUXZOHJ-UHFFFAOYSA-N 3-amino-4-methyldecanoic acid Chemical compound CCCCCCC(C)C(N)CC(O)=O WORUZBFCUXZOHJ-UHFFFAOYSA-N 0.000 description 1
- KEZZGIFSTDSATA-UHFFFAOYSA-N 3-amino-4-methylnonanoic acid Chemical compound CCCCCC(C)C(N)CC(O)=O KEZZGIFSTDSATA-UHFFFAOYSA-N 0.000 description 1
- WNDLIPKAWDXSDD-UHFFFAOYSA-N 3-amino-4-methyloctanoic acid Chemical compound CCCCC(C)C(N)CC(O)=O WNDLIPKAWDXSDD-UHFFFAOYSA-N 0.000 description 1
- IULIQVOUARZGOO-UHFFFAOYSA-N 3-amino-5,5,6-trimethylheptanoic acid Chemical compound CC(C)C(C)(C)CC(N)CC(O)=O IULIQVOUARZGOO-UHFFFAOYSA-N 0.000 description 1
- LCGCZVFEWKPKBQ-UHFFFAOYSA-N 3-amino-5,5,7-trimethyloctanoic acid Chemical compound CC(C)CC(C)(C)CC(N)CC(O)=O LCGCZVFEWKPKBQ-UHFFFAOYSA-N 0.000 description 1
- HEQORWISLIFIOP-UHFFFAOYSA-N 3-amino-5,5,8-trimethylnonanoic acid Chemical compound CC(C)CCC(C)(C)CC(N)CC(O)=O HEQORWISLIFIOP-UHFFFAOYSA-N 0.000 description 1
- RBGFMLVEOIDOFA-UHFFFAOYSA-N 3-amino-5,5-dimethyldecanoic acid Chemical compound CCCCCC(C)(C)CC(N)CC(O)=O RBGFMLVEOIDOFA-UHFFFAOYSA-N 0.000 description 1
- HCSJVDGOFZXVSV-UHFFFAOYSA-N 3-amino-5,5-dimethylnonanoic acid Chemical compound CCCCC(C)(C)CC(N)CC(O)=O HCSJVDGOFZXVSV-UHFFFAOYSA-N 0.000 description 1
- ITMYONXPNKXDII-UHFFFAOYSA-N 3-amino-5,8-dimethylnonanoic acid Chemical compound CC(C)CCC(C)CC(N)CC(O)=O ITMYONXPNKXDII-UHFFFAOYSA-N 0.000 description 1
- NJVLKMUQIOVNHG-UHFFFAOYSA-N 3-amino-5-cyclobutyl-4-methylpentanoic acid Chemical compound OC(=O)CC(N)C(C)CC1CCC1 NJVLKMUQIOVNHG-UHFFFAOYSA-N 0.000 description 1
- XMTQHPFMHQFXNI-UHFFFAOYSA-N 3-amino-5-cyclohexyl-4-methylpentanoic acid Chemical compound OC(=O)CC(N)C(C)CC1CCCCC1 XMTQHPFMHQFXNI-UHFFFAOYSA-N 0.000 description 1
- WRJAYCQSKUFUTM-UHFFFAOYSA-N 3-amino-5-cyclopentyl-4-methylpentanoic acid Chemical compound OC(=O)CC(N)C(C)CC1CCCC1 WRJAYCQSKUFUTM-UHFFFAOYSA-N 0.000 description 1
- XRTYNQXCPKXJIG-UHFFFAOYSA-N 3-amino-5-cyclopropyl-4-methylpentanoic acid Chemical compound OC(=O)CC(N)C(C)CC1CC1 XRTYNQXCPKXJIG-UHFFFAOYSA-N 0.000 description 1
- ZWYUMQOOBJZKIM-UHFFFAOYSA-N 3-amino-5-methyl-8-(2-methylphenyl)octanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=CC=C1C ZWYUMQOOBJZKIM-UHFFFAOYSA-N 0.000 description 1
- DYEVZBGHLDTBNR-UHFFFAOYSA-N 3-amino-5-methyl-8-(3-methylphenyl)octanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=CC(C)=C1 DYEVZBGHLDTBNR-UHFFFAOYSA-N 0.000 description 1
- JJDVRTVXSKENRP-UHFFFAOYSA-N 3-amino-5-methyl-8-phenyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=CC=C1 JJDVRTVXSKENRP-UHFFFAOYSA-N 0.000 description 1
- GUEQOLSQPOTTME-UHFFFAOYSA-N 3-amino-5-methylheptanoic acid Chemical compound CCC(C)CC(N)CC(O)=O GUEQOLSQPOTTME-UHFFFAOYSA-N 0.000 description 1
- XKWDZEJCUWTBOM-UHFFFAOYSA-N 3-amino-5-methylnonanoic acid Chemical compound CCCCC(C)CC(N)CC(O)=O XKWDZEJCUWTBOM-UHFFFAOYSA-N 0.000 description 1
- JXEHXYFSIOYTAH-UHFFFAOYSA-N 3-amino-5-methyloctanoic acid Chemical compound CCCC(C)CC(N)CC(O)=O JXEHXYFSIOYTAH-UHFFFAOYSA-N 0.000 description 1
- KDLUWSRUCDCRJD-UHFFFAOYSA-N 3-amino-6,7-dimethyloctanoic acid Chemical compound CC(C)C(C)CCC(N)CC(O)=O KDLUWSRUCDCRJD-UHFFFAOYSA-N 0.000 description 1
- LVFHFOOXOPYZJV-UHFFFAOYSA-N 3-amino-6,8-dimethylnonanoic acid Chemical compound CC(C)CC(C)CCC(N)CC(O)=O LVFHFOOXOPYZJV-UHFFFAOYSA-N 0.000 description 1
- POYVFGYVTDVXAL-UHFFFAOYSA-N 3-amino-6,9-dimethyldecanoic acid Chemical compound CC(C)CCC(C)CCC(N)CC(O)=O POYVFGYVTDVXAL-UHFFFAOYSA-N 0.000 description 1
- MPFUZQRZDJJIGX-UHFFFAOYSA-N 3-amino-6-anilino-5-methylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)CNC1=CC=CC=C1 MPFUZQRZDJJIGX-UHFFFAOYSA-N 0.000 description 1
- ZYBPLQLFVXPOOH-UHFFFAOYSA-N 3-amino-6-cyclobutyl-4-methylhexanoic acid Chemical compound OC(=O)CC(N)C(C)CCC1CCC1 ZYBPLQLFVXPOOH-UHFFFAOYSA-N 0.000 description 1
- QXAPPVCMDBQCQV-UHFFFAOYSA-N 3-amino-6-cyclobutylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)C1CCC1 QXAPPVCMDBQCQV-UHFFFAOYSA-N 0.000 description 1
- XFLLFZLSCBFNJM-UHFFFAOYSA-N 3-amino-6-cyclohexyl-4-methylhexanoic acid Chemical compound OC(=O)CC(N)C(C)CCC1CCCCC1 XFLLFZLSCBFNJM-UHFFFAOYSA-N 0.000 description 1
- VHHISCCVQDCXRI-UHFFFAOYSA-N 3-amino-6-cyclohexyl-5-methylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)CC1CCCCC1 VHHISCCVQDCXRI-UHFFFAOYSA-N 0.000 description 1
- QIANTAAMZOBXPN-UHFFFAOYSA-N 3-amino-6-cyclohexylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)C1CCCCC1 QIANTAAMZOBXPN-UHFFFAOYSA-N 0.000 description 1
- SNXUUHWDFVBSBX-UHFFFAOYSA-N 3-amino-6-cyclopentyl-4-methylhexanoic acid Chemical compound OC(=O)CC(N)C(C)CCC1CCCC1 SNXUUHWDFVBSBX-UHFFFAOYSA-N 0.000 description 1
- UFBOLJVGIKJODE-UHFFFAOYSA-N 3-amino-6-cyclopentyl-5-methylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)CC1CCCC1 UFBOLJVGIKJODE-UHFFFAOYSA-N 0.000 description 1
- IMMNOOJXDKHOOA-UHFFFAOYSA-N 3-amino-6-cyclopentylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)C1CCCC1 IMMNOOJXDKHOOA-UHFFFAOYSA-N 0.000 description 1
- KFCSCIWLWWRJEP-UHFFFAOYSA-N 3-amino-6-cyclopropyl-4-methylhexanoic acid Chemical compound OC(=O)CC(N)C(C)CCC1CC1 KFCSCIWLWWRJEP-UHFFFAOYSA-N 0.000 description 1
- VZGDFJXPUUUDRO-UHFFFAOYSA-N 3-amino-6-cyclopropyl-5-methylhexanoic acid Chemical compound OC(=O)CC(N)CC(C)CC1CC1 VZGDFJXPUUUDRO-UHFFFAOYSA-N 0.000 description 1
- OSMIIIZIDCILLJ-UHFFFAOYSA-N 3-amino-6-cyclopropylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)C1CC1 OSMIIIZIDCILLJ-UHFFFAOYSA-N 0.000 description 1
- UQMJIFBIWYTIII-UHFFFAOYSA-N 3-amino-6-methyldecanoic acid Chemical compound CCCCC(C)CCC(N)CC(O)=O UQMJIFBIWYTIII-UHFFFAOYSA-N 0.000 description 1
- XWNWLFBIMCWZGL-UHFFFAOYSA-N 3-amino-7-anilino-5-methylheptanoic acid Chemical compound OC(=O)CC(N)CC(C)CCNC1=CC=CC=C1 XWNWLFBIMCWZGL-UHFFFAOYSA-N 0.000 description 1
- XAAHGONCEDNHFD-UHFFFAOYSA-N 3-amino-7-cyclobutyl-4-methylheptanoic acid Chemical compound OC(=O)CC(N)C(C)CCCC1CCC1 XAAHGONCEDNHFD-UHFFFAOYSA-N 0.000 description 1
- BEVWNYGYKVWLPQ-UHFFFAOYSA-N 3-amino-7-cyclobutyl-6-methylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)CC1CCC1 BEVWNYGYKVWLPQ-UHFFFAOYSA-N 0.000 description 1
- VLFUKHVZHCVEHR-UHFFFAOYSA-N 3-amino-7-cyclohexyl-4-methylheptanoic acid Chemical compound OC(=O)CC(N)C(C)CCCC1CCCCC1 VLFUKHVZHCVEHR-UHFFFAOYSA-N 0.000 description 1
- ZDQUKINEHXVJRF-UHFFFAOYSA-N 3-amino-7-cyclohexyl-6-methylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)CC1CCCCC1 ZDQUKINEHXVJRF-UHFFFAOYSA-N 0.000 description 1
- UCIBLQOPLARDGY-UHFFFAOYSA-N 3-amino-7-cyclopentyl-4-methylheptanoic acid Chemical compound OC(=O)CC(N)C(C)CCCC1CCCC1 UCIBLQOPLARDGY-UHFFFAOYSA-N 0.000 description 1
- UHXZGUXGDOJBGD-UHFFFAOYSA-N 3-amino-7-cyclopentyl-6-methylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)CC1CCCC1 UHXZGUXGDOJBGD-UHFFFAOYSA-N 0.000 description 1
- FCMZYSLCZFHUMM-UHFFFAOYSA-N 3-amino-7-cyclopropyl-4-methylheptanoic acid Chemical compound OC(=O)CC(N)C(C)CCCC1CC1 FCMZYSLCZFHUMM-UHFFFAOYSA-N 0.000 description 1
- DJKRRSBCJCGREA-UHFFFAOYSA-N 3-amino-7-cyclopropyl-6-methylheptanoic acid Chemical compound OC(=O)CC(N)CCC(C)CC1CC1 DJKRRSBCJCGREA-UHFFFAOYSA-N 0.000 description 1
- FRXVVOBOAUAOCA-UHFFFAOYSA-N 3-amino-8-(2,3-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=CC(F)=C1F FRXVVOBOAUAOCA-UHFFFAOYSA-N 0.000 description 1
- WXJZPMQTLWNDGI-UHFFFAOYSA-N 3-amino-8-(2,4-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=C(F)C=C1F WXJZPMQTLWNDGI-UHFFFAOYSA-N 0.000 description 1
- BJJUWJRHAOZTDS-UHFFFAOYSA-N 3-amino-8-(2,5-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC(F)=CC=C1F BJJUWJRHAOZTDS-UHFFFAOYSA-N 0.000 description 1
- IGEGKZVQKNVMQW-UHFFFAOYSA-N 3-amino-8-(2,6-difluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=C(F)C=CC=C1F IGEGKZVQKNVMQW-UHFFFAOYSA-N 0.000 description 1
- OHWKTBIGJBCPHA-UHFFFAOYSA-N 3-amino-8-(2-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=CC=C1F OHWKTBIGJBCPHA-UHFFFAOYSA-N 0.000 description 1
- WRUFUMYBJOJYKF-UHFFFAOYSA-N 3-amino-8-(3-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=CC(F)=C1 WRUFUMYBJOJYKF-UHFFFAOYSA-N 0.000 description 1
- IXVWSDRHSNWDRR-UHFFFAOYSA-N 3-amino-8-(4-fluorophenyl)-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCC1=CC=C(F)C=C1 IXVWSDRHSNWDRR-UHFFFAOYSA-N 0.000 description 1
- OFZJJHYIDMIOBI-UHFFFAOYSA-N 3-amino-8-anilino-5-methyloctanoic acid Chemical compound OC(=O)CC(N)CC(C)CCCNC1=CC=CC=C1 OFZJJHYIDMIOBI-UHFFFAOYSA-N 0.000 description 1
- QAHWZDQEOABWLW-UHFFFAOYSA-N 3-amino-8-cyclobutyl-4-methyloctanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCC1CCC1 QAHWZDQEOABWLW-UHFFFAOYSA-N 0.000 description 1
- WMXQQGVTDZLYLJ-UHFFFAOYSA-N 3-amino-8-cyclobutyl-6-methyloctanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCC1CCC1 WMXQQGVTDZLYLJ-UHFFFAOYSA-N 0.000 description 1
- QGSFQQUMVSTMBX-UHFFFAOYSA-N 3-amino-8-cyclohexyl-4-methyloctanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCC1CCCCC1 QGSFQQUMVSTMBX-UHFFFAOYSA-N 0.000 description 1
- AHHLMWKLWUYOQH-UHFFFAOYSA-N 3-amino-8-cyclohexyl-6-methyloctanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCC1CCCCC1 AHHLMWKLWUYOQH-UHFFFAOYSA-N 0.000 description 1
- UYSDRJNMTHVXFC-UHFFFAOYSA-N 3-amino-8-cyclopentyl-4-methyloctanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCC1CCCC1 UYSDRJNMTHVXFC-UHFFFAOYSA-N 0.000 description 1
- LVMANRYTMRTWNA-UHFFFAOYSA-N 3-amino-8-cyclopentyl-6-methyloctanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCC1CCCC1 LVMANRYTMRTWNA-UHFFFAOYSA-N 0.000 description 1
- CYGNJFPUSKKPGI-UHFFFAOYSA-N 3-amino-8-cyclopropyl-4-methyloctanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCC1CC1 CYGNJFPUSKKPGI-UHFFFAOYSA-N 0.000 description 1
- SBFUHNDWSDWPNV-UHFFFAOYSA-N 3-amino-8-cyclopropyl-6-methyloctanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCC1CC1 SBFUHNDWSDWPNV-UHFFFAOYSA-N 0.000 description 1
- IQVRQFLAPNGDDZ-UHFFFAOYSA-N 3-amino-9-cyclobutyl-4-methylnonanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCCC1CCC1 IQVRQFLAPNGDDZ-UHFFFAOYSA-N 0.000 description 1
- XEDARUVJQRFVGB-UHFFFAOYSA-N 3-amino-9-cyclobutyl-6-methylnonanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCC1CCC1 XEDARUVJQRFVGB-UHFFFAOYSA-N 0.000 description 1
- BHHYAIYNLUAWSP-UHFFFAOYSA-N 3-amino-9-cyclohexyl-4-methylnonanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCCC1CCCCC1 BHHYAIYNLUAWSP-UHFFFAOYSA-N 0.000 description 1
- JUKPMBVQCZNQNA-UHFFFAOYSA-N 3-amino-9-cyclohexyl-6-methylnonanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCC1CCCCC1 JUKPMBVQCZNQNA-UHFFFAOYSA-N 0.000 description 1
- RVEFLVVMIXKKIR-UHFFFAOYSA-N 3-amino-9-cyclopentyl-4-methylnonanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCCC1CCCC1 RVEFLVVMIXKKIR-UHFFFAOYSA-N 0.000 description 1
- QJTBKRLAAAKINB-UHFFFAOYSA-N 3-amino-9-cyclopentyl-6-methylnonanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCC1CCCC1 QJTBKRLAAAKINB-UHFFFAOYSA-N 0.000 description 1
- QGFBHVWGGPHMQU-UHFFFAOYSA-N 3-amino-9-cyclopropyl-4-methylnonanoic acid Chemical compound OC(=O)CC(N)C(C)CCCCCC1CC1 QGFBHVWGGPHMQU-UHFFFAOYSA-N 0.000 description 1
- BQRPWAJQPDMQRX-UHFFFAOYSA-N 3-amino-9-cyclopropyl-6-methylnonanoic acid Chemical compound OC(=O)CC(N)CCC(C)CCCC1CC1 BQRPWAJQPDMQRX-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YJUJGBZYQJQTFX-UHFFFAOYSA-N 4,4-dimethylheptanoic acid Chemical compound CCCC(C)(C)CCC(O)=O YJUJGBZYQJQTFX-UHFFFAOYSA-N 0.000 description 1
- XUPXMIAWKPTZLZ-UHFFFAOYSA-N 4-methylhexan-2-one Chemical compound CCC(C)CC(C)=O XUPXMIAWKPTZLZ-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QPKCDMXLSDFCQD-UHFFFAOYSA-N 8-bromo-2,6-dimethyloct-2-ene Chemical compound BrCCC(C)CCC=C(C)C QPKCDMXLSDFCQD-UHFFFAOYSA-N 0.000 description 1
- CMFIWMWBTZQTQH-IDTAVKCVSA-N 9-[(2r,3r,4s,5s)-3,4-dihydroxy-5-(2-methylpropylsulfanylmethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CSCC(C)C)O[C@H]1N1C(NC=NC2=O)=C2N=C1 CMFIWMWBTZQTQH-IDTAVKCVSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- 208000008811 Agoraphobia Diseases 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 208000000412 Avitaminosis Diseases 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- 206010005063 Bladder pain Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KITOMFFQZQCVCK-UHFFFAOYSA-N C(C)OC(C(=CC(CC=C)(C)C)C#N)=O.Cl.NCC(C(=O)O)CC(CCC)(C)C Chemical compound C(C)OC(C(=CC(CC=C)(C)C)C#N)=O.Cl.NCC(C(=O)O)CC(CCC)(C)C KITOMFFQZQCVCK-UHFFFAOYSA-N 0.000 description 1
- HCTJGOHAWPFNGT-UHFFFAOYSA-N C(C)OC(C(=CC1(CC1)C)C#N)=O.NCC(C(=O)O)CC1(CC1)C Chemical compound C(C)OC(C(=CC1(CC1)C)C#N)=O.NCC(C(=O)O)CC1(CC1)C HCTJGOHAWPFNGT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010068631 Childhood depression Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 1
- 238000006568 Claisen-Johnson rearrangement reaction Methods 0.000 description 1
- 208000006561 Cluster Headache Diseases 0.000 description 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- 208000016192 Demyelinating disease Diseases 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010014498 Embolic stroke Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 206010015958 Eye pain Diseases 0.000 description 1
- 206010016059 Facial pain Diseases 0.000 description 1
- 206010016275 Fear Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 201000011240 Frontotemporal dementia Diseases 0.000 description 1
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 1
- 208000001613 Gambling Diseases 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 206010018985 Haemorrhage intracranial Diseases 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- 208000029433 Herpesviridae infectious disease Diseases 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 206010049949 Intercostal neuralgia Diseases 0.000 description 1
- 208000008574 Intracranial Hemorrhages Diseases 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 208000007914 Labor Pain Diseases 0.000 description 1
- 208000035945 Labour pain Diseases 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 206010027940 Mood altered Diseases 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 206010028391 Musculoskeletal Pain Diseases 0.000 description 1
- RFYSVSBRODBZPT-UHFFFAOYSA-N NCC(C(=O)O)CC(CCC)(C)C.NCC(C(=O)O)CC(CCCC(C)C)CC.NCC(C(=O)O)CC(CCCCC)CC.NCC(C(=O)O)CC(CCC(C)C)CC Chemical compound NCC(C(=O)O)CC(CCC)(C)C.NCC(C(=O)O)CC(CCCC(C)C)CC.NCC(C(=O)O)CC(CCCCC)CC.NCC(C(=O)O)CC(CCC(C)C)CC RFYSVSBRODBZPT-UHFFFAOYSA-N 0.000 description 1
- TXPRGGPGXOKVTO-UHFFFAOYSA-N NCC(C(=O)O)CC(CCCC(C)C)(C)C.NCC(C(=O)O)CC1(CC1)CCCC(C)C Chemical compound NCC(C(=O)O)CC(CCCC(C)C)(C)C.NCC(C(=O)O)CC1(CC1)CCCC(C)C TXPRGGPGXOKVTO-UHFFFAOYSA-N 0.000 description 1
- SQACAVHCOKWDEX-UHFFFAOYSA-N NCC(C(=O)O)CC1(CC1)CC(C)C.NCC(C(=O)O)CC1(CC1)CCCC.NCC(C(=O)O)CC1(CC1)C(C)C Chemical compound NCC(C(=O)O)CC1(CC1)CC(C)C.NCC(C(=O)O)CC1(CC1)CCCC.NCC(C(=O)O)CC1(CC1)C(C)C SQACAVHCOKWDEX-UHFFFAOYSA-N 0.000 description 1
- HCMHEJAECMTJOD-UHFFFAOYSA-N NCC(C(=O)O)CC1(CC1)CC.NCC(C(=O)O)CC1(CC1)C Chemical compound NCC(C(=O)O)CC1(CC1)CC.NCC(C(=O)O)CC1(CC1)C HCMHEJAECMTJOD-UHFFFAOYSA-N 0.000 description 1
- SMDNKBBSUIVYHQ-UHFFFAOYSA-N NCC(C(=O)O)CC1(CCC1)CC.NCC(C(=O)O)CC1(CCC1)C.NCC(C(=O)O)CC1(CC1)CCCC(C)C Chemical compound NCC(C(=O)O)CC1(CCC1)CC.NCC(C(=O)O)CC1(CCC1)C.NCC(C(=O)O)CC1(CC1)CCCC(C)C SMDNKBBSUIVYHQ-UHFFFAOYSA-N 0.000 description 1
- IBKWXEFEHOIPEH-UHFFFAOYSA-N NCC(C(=O)O)CC1(CCCCC1)CCC.NCC(C(=O)O)CC1(CCCCC1)CC.NCC(C(=O)O)CC1(CCCCC1)C Chemical compound NCC(C(=O)O)CC1(CCCCC1)CCC.NCC(C(=O)O)CC1(CCCCC1)CC.NCC(C(=O)O)CC1(CCCCC1)C IBKWXEFEHOIPEH-UHFFFAOYSA-N 0.000 description 1
- UOJGIIVHHHACLD-UHFFFAOYSA-N NCC(C(=O)O)CCC1(CCCC1)C.NCC(C(=O)O)CCC1CCCC1.NCC(C(=O)O)CCC1(CCC1)CC.NCC(C(=O)O)CCC1(CCC1)C Chemical compound NCC(C(=O)O)CCC1(CCCC1)C.NCC(C(=O)O)CCC1CCCC1.NCC(C(=O)O)CCC1(CCC1)CC.NCC(C(=O)O)CCC1(CCC1)C UOJGIIVHHHACLD-UHFFFAOYSA-N 0.000 description 1
- WCTRBYIGBZWSME-UHFFFAOYSA-N NCC(C(=O)O)CCC1(CCCCC1)CC.NCC(C(=O)O)CCC1(CCCCC1)C.NCC(C(=O)O)CCC1CCCCC1.NCC(C(=O)O)CCC1(CCCC1)CC Chemical compound NCC(C(=O)O)CCC1(CCCCC1)CC.NCC(C(=O)O)CCC1(CCCCC1)C.NCC(C(=O)O)CCC1CCCCC1.NCC(C(=O)O)CCC1(CCCC1)CC WCTRBYIGBZWSME-UHFFFAOYSA-N 0.000 description 1
- XUKFTAUIEINYIW-UHFFFAOYSA-N NCC(C(=O)O)CCCCCC(C)C.NCC(C(=O)O)CC(CCCC(C)C)(C)C Chemical compound NCC(C(=O)O)CCCCCC(C)C.NCC(C(=O)O)CC(CCCC(C)C)(C)C XUKFTAUIEINYIW-UHFFFAOYSA-N 0.000 description 1
- 206010028923 Neonatal asphyxia Diseases 0.000 description 1
- 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 201000005625 Neuroleptic malignant syndrome Diseases 0.000 description 1
- 208000005890 Neuroma Diseases 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 206010068106 Occipital neuralgia Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 208000004983 Phantom Limb Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 206010073211 Postural tremor Diseases 0.000 description 1
- 208000027030 Premenstrual dysphoric disease Diseases 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 208000027465 Psychotic Affective disease Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 208000005793 Restless legs syndrome Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 206010049002 Scar pain Diseases 0.000 description 1
- 208000020114 Schizophrenia and other psychotic disease Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 201000000552 Scott syndrome Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 208000019568 Shared Paranoid disease Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 208000013200 Stress disease Diseases 0.000 description 1
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010043269 Tension headache Diseases 0.000 description 1
- 208000008548 Tension-Type Headache Diseases 0.000 description 1
- 208000009205 Tinnitus Diseases 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 208000024248 Vascular System injury Diseases 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 208000012339 Vascular injury Diseases 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 206010047627 Vitamin deficiencies Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 206010053552 allodynia Diseases 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000010976 amide bond formation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 206010003074 arachnoiditis Diseases 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000025748 atypical depressive disease Diseases 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 description 1
- RCUIWQWWDLZNMS-UHFFFAOYSA-N benzyl 2-cyanoacetate Chemical compound N#CCC(=O)OCC1=CC=CC=C1 RCUIWQWWDLZNMS-UHFFFAOYSA-N 0.000 description 1
- OIAUXDRKTSQTDO-UHFFFAOYSA-N benzyl n-(methoxymethyl)carbamate Chemical compound COCNC(=O)OCC1=CC=CC=C1 OIAUXDRKTSQTDO-UHFFFAOYSA-N 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 208000022257 bipolar II disease Diseases 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 208000030963 borderline personality disease Diseases 0.000 description 1
- 208000006752 brain edema Diseases 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229960003563 calcium carbonate Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000013172 carotid endarterectomy Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000002585 cerebral angiography Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- IFMWVBVPVXRZHE-UHFFFAOYSA-M chlorotitanium(3+);propan-2-olate Chemical compound [Cl-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-] IFMWVBVPVXRZHE-UHFFFAOYSA-M 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 208000018912 cluster headache syndrome Diseases 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229960002069 diamorphine Drugs 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 201000006517 essential tremor Diseases 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- FNBVLJQKVOCDLF-UHFFFAOYSA-N ethyl 2-(aminomethyl)-4,4-dimethylheptanoate Chemical compound CCCC(C)(C)CC(CN)C(=O)OCC FNBVLJQKVOCDLF-UHFFFAOYSA-N 0.000 description 1
- KUVHKGLXGXVDHG-UHFFFAOYSA-N ethyl 2-cyano-3-(1-methylcyclopropyl)prop-2-enoate Chemical compound CCOC(=O)C(C#N)=CC1(C)CC1 KUVHKGLXGXVDHG-UHFFFAOYSA-N 0.000 description 1
- UUSOZWFRBGMZFS-UHFFFAOYSA-N ethyl 2-cyano-4,4-dimethylhepta-2,6-dienoate Chemical compound CCOC(=O)C(C#N)=CC(C)(C)CC=C UUSOZWFRBGMZFS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001097 facial muscle Anatomy 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000000380 hallucinogen Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 208000003532 hypothyroidism Diseases 0.000 description 1
- 230000002989 hypothyroidism Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 206010021654 increased appetite Diseases 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N isodecanoic acid Natural products CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- 210000004086 maxillary sinus Anatomy 0.000 description 1
- 201000003995 melancholia Diseases 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007510 mood change Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- ZYZHMSJNPCYUTB-UHFFFAOYSA-N n-benzyl-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(C)NCC1=CC=CC=C1 ZYZHMSJNPCYUTB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229940072228 neurontin Drugs 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 229940053982 other anxiolytics in atc Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 208000013667 paroxysmal dyskinesia Diseases 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 208000033300 perinatal asphyxia Diseases 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UIDUKLCLJMXFEO-UHFFFAOYSA-N propylsilane Chemical compound CCC[SiH3] UIDUKLCLJMXFEO-UHFFFAOYSA-N 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000036385 rapid eye movement (rem) sleep Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000008653 root damage Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000005809 status epilepticus Diseases 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 206010042772 syncope Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 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 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- ZCEOVQSIOGHSOW-LLVKDONJSA-N tert-butyl (3s)-3-amino-5,5-dimethyloctanoate Chemical compound CCCC(C)(C)C[C@H](N)CC(=O)OC(C)(C)C ZCEOVQSIOGHSOW-LLVKDONJSA-N 0.000 description 1
- DQRWHAAHPMNUSA-GOSISDBHSA-N tert-butyl (3s)-5,5-dimethyl-3-(phenylmethoxycarbonylamino)octanoate Chemical compound CCCC(C)(C)C[C@@H](CC(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1 DQRWHAAHPMNUSA-GOSISDBHSA-N 0.000 description 1
- NNXLBEZXSLSMDX-DSKINZAPSA-N tert-butyl (3s)-5,5-dimethyl-3-[(4s,5r)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]octanoate Chemical compound O1C(=O)N(C(=O)[C@H](CC(=O)OC(C)(C)C)CC(C)(C)CCC)[C@@H](C)[C@H]1C1=CC=CC=C1 NNXLBEZXSLSMDX-DSKINZAPSA-N 0.000 description 1
- BIRWKKXCRCFMKP-HROGELHOSA-N tert-butyl (3s,5r)-5-methyl-3-[(4r,5s)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]nonanoate Chemical compound O1C(=O)N(C(=O)[C@H](CC(=O)OC(C)(C)C)C[C@H](C)CCCC)[C@H](C)[C@@H]1C1=CC=CC=C1 BIRWKKXCRCFMKP-HROGELHOSA-N 0.000 description 1
- BUNCMUJWNQIRRP-LLVKDONJSA-N tert-butyl (5s)-5-methylocta-2,6-dienoate Chemical compound CC=C[C@@H](C)CC=CC(=O)OC(C)(C)C BUNCMUJWNQIRRP-LLVKDONJSA-N 0.000 description 1
- ZCEOVQSIOGHSOW-UHFFFAOYSA-N tert-butyl 3-amino-5,5-dimethyloctanoate Chemical compound CCCC(C)(C)CC(N)CC(=O)OC(C)(C)C ZCEOVQSIOGHSOW-UHFFFAOYSA-N 0.000 description 1
- NNXLBEZXSLSMDX-UHFFFAOYSA-N tert-butyl 5,5-dimethyl-3-(4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl)octanoate Chemical compound O1C(=O)N(C(=O)C(CC(=O)OC(C)(C)C)CC(C)(C)CCC)C(C)C1C1=CC=CC=C1 NNXLBEZXSLSMDX-UHFFFAOYSA-N 0.000 description 1
- DQRWHAAHPMNUSA-UHFFFAOYSA-N tert-butyl 5,5-dimethyl-3-(phenylmethoxycarbonylamino)octanoate Chemical compound CCCC(C)(C)CC(CC(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1 DQRWHAAHPMNUSA-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- 230000006441 vascular event Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Cardiology (AREA)
- Nutrition Science (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
Abstract
【解決手段】例えば2−アミノメチル−4−メチル−7−フェニル−ヘプタン酸あるいは2−アミノメチル−4−メチル−6−フェニル−ヘキサン酸等のカルシウムチャンネルのアルファ−2−デルタ(α2δ)サブユニットに結合するβ−アミノ酸。
【選択図】なし
Description
本発明はカルシウムチャネルのアルファ−2−デルタ(α2δ)サブユニットに結合するあるβ−アミノ酸に関する。これらの化合物及びそれらの医薬として許容される塩はさまざまな精神科の、痛みの及び他の障害の治療において有用である。
本発明は式Iの化合物:
R2は1〜5のフッ素原子で場合により置換される水素又は(C1−C6)アルキルである;又は
R1及びR2は、それらが結合する炭素と共に、3〜6員のシクロアルキル環を形成する;
R3は(C1−C6)アルキル、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C3)アルキル、フェニル、フェニル−(C1−C3)アルキル、ピリヂル、ピリヂル−(C1−C3)アルキル、フェニル−N(H)−又はピリヂル−N(H)−である、ここで、上記アルキル基のそれぞれは1〜5のフッ素原子で、好ましくは0〜3のフッ素原子で場合により置換されうる、及びここで、前記フェニル及び前記ピリヂル並びに前記フェニル−(C1−C3)アルキル及び前記ピリヂル−(C1−C3)アルキルのフェニル及びピリヂル基、それぞれは、クロロ、フルオロ、アミノ、ニトロ、シアノ、(C1−C3)アルキルアミノ、1〜3のフッ素原子で場合により置換される(C1−C3)アルキル及び1〜3のフッ素原子で場合により置換される(C1−C3)アルコキシから独立に選ばれる、1〜3の置換基で、好ましくは0〜2の置換基で場合により置換されうる;
R4は1〜5のフッ素原子で場合により置換される水素又は(C1−C6)アルキルである;
R5は1〜5のフッ素原子で場合により置換される水素又は(C1−C6)アルキルである;及び
R6は水素又は(C1−C6)アルキルである}
及び上記化合物の医薬として許容される塩に関する。
3−アミノ−5,8−ヂメチル−ノナノン酸;
3−アミノ−5,5,7−トリメチル−オクタノン酸;
3−アミノ−5,5,8−トリメチル−ノナノン酸;
3−アミノ−5,5,6−トリメチル−ヘプタノン酸;
(3S,5S)−3−アミノ−5,8−ヂメチル−ノナノン酸;
(3S,5R)−3−アミノ−5,8−ヂメチル−ノナノン酸;
(3S)−3−アミノ−5,5,6−トリメチル−ヘプタノン酸;
(3S)−3−アミノ−5,5,7−トリメチル−オクタノン酸;
(3S)−3−アミノ−5,5,8−トリメチル−ノナノン酸;及び
(3S)−3−アミノ−5,5,9−トリメチル−デカノン酸
及びそれらの医薬として許容される塩を含む。
3−アミノ−6−シクロブチル−5−メチル−ヘキサノン酸;
3−アミノ−7−シクロプロピル−5−メチル−ヘプタノン酸;
3−アミノ−7−シクロブチル−5−メチル−ヘプタノン酸;
3−アミノ−7−シクロペンチル−5−メチル−ヘプタノン酸;
3−アミノ−7−シクロヘキシル−5−メチル−ヘプタノン酸;
3−アミノ−8−シクロプロピル−5−メチル−オクタノン酸;
3−アミノ−8−シクロブチル−5−メチル−オクタノン酸;
3−アミノ−8−シクロペンチル−5−メチル−オクタノン酸;
3−アミノ−8−シクロヘキシル−5−メチル−オクタノン酸;
3−アミノ−6−シクロプロピル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−6−シクロブチル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−6−シクロペンチル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−6−シクロヘキシル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−7−シクロプロピル−5,5−ヂメチル−ヘプタノン酸;
3−アミノ−7−シクロブチル−5,5−ヂメチル−ヘプタノン酸;
3−アミノ−7−シクロペンチル−5,5−ヂメチル−ヘプタノン酸;
3−アミノ−7−シクロヘキシル−5,5−ヂメチル−ヘプタノン酸;
(3S,5R)−3−アミノ−7−シクロプロピル−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−7−シクロブチル−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−7−シクロペンチル−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−7−シクロヘキシル−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−8−シクロプロピル−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−シクロブチル−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−シクロペンチル−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−シクロヘキシル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−6−シクロブチル−5−メチル−ヘキサノン酸;
(3S,5S)−3−アミノ−7−シクロプロピル−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−7−シクロブチル−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−7−シクロペンチル−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−7−シクロヘキシル−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−8−シクロプロピル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−シクロブチル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−シクロペンチル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−シクロヘキシル−5−メチル−オクタノン酸;
(3S)−3−アミノ−6−シクロプロピル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−6−シクロブチル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−6−シクロペンチル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−6−シクロヘキシル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−7−シクロプロピル−5,5−ヂメチル−ヘプタノン酸;
(3S)−3−アミノ−7−シクロブチル−5,5−ヂメチル−ヘプタノン酸;
(3S)−3−アミノ−7−シクロペンチル−5,5−ヂメチル−ヘプタノン酸;及び
(3S)−3−アミノ−7−シクロヘキシル−5,5−ヂメチル−ヘプタノン酸
及びそれらの医薬として許容される塩である。
3−アミノ−5−メチル−ヘプタノン酸;
3−アミノ−5−メチル−オクタノン酸;
3−アミノ−5−メチル−ノナノン酸;
3−アミノ−5,5−ヂメチル−ノナノン酸;
3−アミノ−5,5−ヂメチル−デカノン酸;
(3S)−3−アミノ−5,5−ヂメチル−ノナノン酸;及び
(3S)−3−アミノ−5,5−ヂメチル−デカノン酸
及びそれらの医薬として許容される塩を含む。
R2は1〜5のフッ素原子で場合により置換される水素又は(C1−C3)アルキルである;又は
R1及びR2は、それらが結合する炭素と共に、3〜6員のシクロアルキル環を形成する;
R3は(C1−C6)アルキル、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C3)アルキル、フェニル、フェニル−(C1−C3)アルキル、ピリヂル、ピリヂル−(C1−C3)アルキル、フェニル−N(H)−又はピリヂル−N(H)−である、ここで、上記アルキル基のそれぞれは1〜5のフッ素原子で、好ましくは0〜3のフッ素原子で場合により置換されうる、及びここで、前記フェニル及び前記ピリヂル並びに前記フェニル−(C1−C3)アルキル及び前記ピリヂル−(C1−C3)アルキルのフェニル及びピリヂル基、それぞれは、クロロ、フルオロ、アミノ、ニトロ、シアノ、(C1−C3)アルキルアミノ、1〜3のフッ素原子で場合により置換される(C1−C3)アルキル及び1〜3のフッ素原子で場合により置換される(C1−C3)アルコキシから独立に選ばれる、1〜3の置換基で、好ましくは0〜2の置換基で場合により置換されうる;
ここで、R1が水素であるとき、R2は水素ではない}
及び上記化合物の医薬として許容される塩にも関する。
3−アミノ−5−メチル−8−フェニルアミノ−オクタノン酸;
3−アミノ−5−メチル−7−フェニルアミノ−ヘプタノン酸;
3−アミノ−5−メチル−6−フェニルアミノ−ヘキサノン酸;
(3S,5R)−3−アミノ−5−メチル−8−フェニルアミノ−オクタノン酸;
(3S,5R)−3−アミノ−5−メチル−7−フェニルアミノ−ヘプタノン酸;
(3S,5R)−3−アミノ−5−メチル−6−フェニルアミノ−ヘキサノン酸;
(3S,5S)−3−アミノ−5−メチル−8−フェニルアミノ−オクタノン酸;
(3S,5S)−3−アミノ−5−メチル−7−フェニルアミノ−ヘプタノン酸;
(3S,5S)−3−アミノ−5−メチル−6−フェニルアミノ−ヘキサノン酸;
3−アミノ−5−メチル−8−フェニル−オクタノン酸;
3−アミノ−8−(2−フルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(3−フルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(4−フルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(2−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(3−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(4−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−5−メチル−8−m−トリル−オクタノン酸;
3−アミノ−5−メチル−8−p−トリル−オクタノン酸;
3−アミノ−5−メチル−8−p−トリル−オクタノン酸;
3−アミノ−8−(2,3−ヂフルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(2,4−ヂフルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(2,5−ヂフルオロ−フェニル)−5−メチル−オクタノン酸;
3−アミノ−8−(2,6−ヂフルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−5−メチル−8−フェニル−オクタノン酸;
(3S,5S)−3−アミノ−5−メチル−8−フェニル−オクタノン酸;
(3S,5R)−3−アミノ−8−(2−フルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(2−フルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(3−フルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(3−フルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(4−フルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(4−フルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(2−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(3−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(3−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(4−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(4−トリフルオロ−フェニル)−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−5−メチル−8−o−トリル−オクタノン酸;
(3S,5R)−3−アミノ−5−メチル−8−m−トリル−オクタノン酸;
(3S,5S)−3−アミノ−5−メチル−8−m−トリル−オクタノン酸;
(3S,5R)−3−アミノ−5−メチル−8−p−トリル−オクタノン酸;
(3S,5S)−3−アミノ−5−メチル−8−p−トリル−オクタノン酸;
(3S,5R)−3−アミノ−8−(2,3−ヂフルオロ−フェニル)5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(2,3−ヂフルオロ−フェニル)5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(2,4−ヂフルオロ−フェニル)5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(2,4−ヂフルオロ−フェニル)5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(2,5−ヂフルオロ−フェニル)5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−(2,5−ヂフルオロ−フェニル)5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−(2,6−ヂフルオロ−フェニル)5−メチル−オクタノン酸;及び
(3S,5S)−3−アミノ−8−(2,6−ヂフルオロ−フェニル)−5−メチル−オクタノン酸
及びそれらの医薬として許容される塩を含む。
(3S,5R)−3−アミノ−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−5−メチル−オクタノン酸;及び
(3S,5R)−3−アミノ−5−メチル−ノナノン酸
及びそれらの医薬として許容される塩である。
及びそれらの医薬として許容される塩にも関し、及びここで、前記化合物は以下の化合物:
3−アミノ−4,5−ヂメチル−ヘキサノン酸;
3−アミノ−4,6−ヂメチル−ヘプタノン酸;
3−アミノ−4,7−ヂメチル−オクタノン酸;
3−アミノ−4,8−ヂメチル−ノナノン酸;
3−アミノ−4,9−ヂメチル−デカノン酸;
3−アミノ−4−シクロプロピル−ペンタノン酸;
3−アミノ−4−シクロブチル−ペンタノン酸;
3−アミノ−4−シクロペンチル−ペンタノン酸;
3−アミノ−4−シクロヘキシル−ペンタノン酸;
3−アミノ−5−シクロブチル−4−メチル−ペンタノン酸;
3−アミノ−5−シクロペンチル−4−メチル−ペンタノン酸;
3−アミノ−5−シクロヘキシル−4−メチル−ペンタノン酸;
3−アミノ−6−シクロプロピル−4−メチル−ヘキサノン酸;
3−アミノ−6−シクロブチル−4−メチル−ヘキサノン酸;
3−アミノ−6−シクロペンチル−4−メチル−ヘキサノン酸;
3−アミノ−6−シクロヘキシル−4−メチル−ヘキサノン酸;
3−アミノ−7−シクロプロピル−4−メチル−ヘプタノン酸;
3−アミノ−7−シクロブチル−4−メチル−ヘプタノン酸;
3−アミノ−7−シクロペンチル−4−メチル−ヘプタノン酸;
3−アミノ−7−シクロヘキシル−4−メチル−ヘプタノン酸;
3−アミノ−8−シクロプロピル−4−メチル−オクタノン酸;
3−アミノ−8−シクロブチル−4−メチル−オクタノン酸;
3−アミノ−8−シクロペンチル−4−メチル−オクタノン酸;
3−アミノ−8−シクロヘキシル−4−メチル−オクタノン酸;
3−アミノ−9−シクロプロピル−4−メチル−ノナノン酸;
3−アミノ−9−シクロブチル−4−メチル−ノナノン酸;
3−アミノ−9−シクロペンチル−4−メチル−ノナノン酸;
3−アミノ−9−シクロヘキシル−4−メチル−ノナノン酸;
3−アミノ−4−メチル−ノナノン酸;
3−アミノ−4−メチル−デカノン酸;
(3R,4R)−3−アミノ−4,5−ヂメチル−ヘキサノン酸;
(3R,4R)−3−アミノ−4,6−ヂメチル−ヘプタノン酸;
(3R,4R)−3−アミノ−4,7−ヂメチル−オクタノン酸;
(3R,4R)−3−アミノ−4,8−ヂメチル−ノナノン酸;
(3R,4R)−3−アミノ−4,9−ヂメチル−デカノン酸;
(3R,4R)−3−アミノ−4−シクロプロピル−ペンタノン酸;
(3R,4R)−3−アミノ−4−シクロブチル−ペンタノン酸;
(3R,4R)−3−アミノ−4−シクロペンチル−ペンタノン酸;
(3R,4R)−3−アミノ−4−シクロヘキシル−ペンタノン酸;
(3R,4R)−3−アミノ−5−シクロプロピル−4−メチル−ペンタノン酸;
(3R,4R)−3−アミノ−5−シクロブチル−4−メチル−ペンタノン酸;
(3R,4R)−3−アミノ−5−シクロペンチル−4−メチル−ペンタノン酸;
(3R,4R)−3−アミノ−5−シクロヘキシル−4−メチル−ペンタノン酸;
(3R,4R)−3−アミノ−6−シクロプロピル−4−メチル−ヘキサノン酸;
(3R,4R)−3−アミノ−6−シクロブチル−4−メチル−ヘキサノン酸;
(3R,4R)−3−アミノ−6−シクロペンチル−4−メチル−ヘキサノン酸;
(3R,4R)−3−アミノ−6−シクロヘキシル−4−メチル−ヘキサノン酸;
(3R,4R)−3−アミノ−7−シクロプロピル−4−メチル−ヘプタノン酸;
(3R,4R)−3−アミノ−7−シクロブチル−4−メチル−ヘプタノン酸;
(3R,4R)−3−アミノ−7−シクロヘキシル−4−メチル−ヘプタノン酸;
(3R,4R)−3−アミノ−8−シクロプロピル−4−メチル−オクタノン酸;
(3R,4R)−3−アミノ−8−シクロブチル−4−メチル−オクタノン酸;
(3R,4R)−3−アミノ−8−シクロペンチル−4−メチル−オクタノン酸;
(3R,4R)−3−アミノ−8−シクロヘキシル−4−メチル−オクタノン酸;
(3R,4R)−3−アミノ−9−シクロプロピル−4−メチル−ノナノン酸;
(3R,4R)−3−アミノ−9−シクロブチル−4−メチル−ノナノン酸;
(3R,4R)−3−アミノ−9−シクロペンチル−4−メチル−ノナノン酸;
(3R,4R)−3−アミノ−9−シクロヘキシル−4−メチル−ノナノン酸;
(3R,4R)−3−アミノ−4−メチル−ノナノン酸;
(3R,4R)−3−アミノ−4−メチル−デカノン酸;
(3R,4S)−3−アミノ−4,5−ヂメチル−ヘキサノン酸;
(3R,4S)−3−アミノ−4,6−ヂメチル−ヘプタノン酸;
(3R,4S)−3−アミノ−4,7−ヂメチル−オクタノン酸;
(3R,4S)−3−アミノ−4,8−ヂメチル−ノナノン酸;
(3R,4S)−3−アミノ−4,9−ヂメチル−デカノン酸;
(3R,4S)−3−アミノ−4−シクロプロピル−ペンタノン酸;
(3R,4S)−3−アミノ−4−シクロブチル−ペンタノン酸;
(3R,4S)−3−アミノ−4−シクロペンチル−ペンタノン酸;
(3R,4S)−3−アミノ−4−シクロヘキシル−ペンタノン酸;
(3R,4S)−3−アミノ−5−シクロブチル−4−メチル−ペンタノン酸;
(3R,4S)−3−アミノ−5−シクロペンチル−4−メチル−ペンタノン酸;
(3R,4S)−3−アミノ−5−シクロヘキシル−4−メチル−ペンタノン酸;
(3R,4S)−3−アミノ−6−シクロプロピル−4−メチル−ヘキサノン酸;
(3R,4S)−3−アミノ−6−シクロブチル−4−メチル−ヘキサノン酸;
(3R,4S)−3−アミノ−6−シクロペンチル−4−メチル−ヘキサノン酸;
(3R,4S)−3−アミノ−6−シクロヘキシル−4−メチル−ヘキサノン酸;
(3R,4S)−3−アミノ−7−シクロプロピル−4−メチル−ヘプタノン酸;
(3R,4S)−3−アミノ−7−シクロブチル−4−メチル−ヘプタノン酸;
(3R,4S)−3−アミノ−7−シクロペンチル−4−メチル−ヘプタノン酸;
(3R,4S)−3−アミノ−7−シクロヘキシル−4−メチル−ヘプタノン酸;
(3R,4S)−3−アミノ−8−シクロプロピル−4−メチル−オクタノン酸;
(3R,4S)−3−アミノ−8−シクロブチル−4−メチル−オクタノン酸;
(3R,4S)−3−アミノ−8−シクロペンチル−4−メチル−オクタノン酸;
(3R,4S)−3−アミノ−8−シクロヘキシル−4−メチル−オクタノン酸;
(3R,4S)−3−アミノ−9−シクロプロピル−4−メチル−ノナノン酸;
(3R,4S)−3−アミノ−9−シクロブチル−4−メチル−ノナノン酸;
(3R,4S)−3−アミノ−9−シクロペンチル−4−メチル−ノナノン酸;
(3R,4S)−3−アミノ−9−シクロヘキシル−4−メチル−ノナノン酸;
(3R,4S)−3−アミノ−4−メチル−オクタノン酸;
(3R,4S)−3−アミノ−4−メチル−ノナノン酸;及び
(3R,4S)−3−アミノ−4−メチル−デカノン酸
及びそれらの医薬として許容される塩から選ばれる。
及びそれらの医薬として許容される塩にも関し、及びここで、前記化合物は以下の化合物:
3−アミノ−6−メチル−デカノン酸;
3−アミノ−6−シクロプロピル−ヘプタノン酸;
3−アミノ−6−シクロブチル−ヘプタノン酸;
3−アミノ−6−シクロペンチル−ヘプタノン酸;
3−アミノ−6−シクロヘキシル−ヘプタノン酸;
3−アミノ−7−シクロブチル−6−メチル−ヘプタノン酸;
3−アミノ−7−シクロペンチル−6−メチル−ヘプタノン酸;
3−アミノ−7−シクロヘキシル−6−メチル−ヘプタノン酸;
3−アミノ−8−シクロプロピル−6−メチル−オクタノン酸;
3−アミノ−8−シクロブチル−6−メチル−オクタノン酸;
3−アミノ−8−シクロペンチル−6−メチル−オクタノン酸;
3−アミノ−8−シクロヘキシル−6−メチル−オクタノン酸;
3−アミノ−9−シクロプロピル−6−メチル−ノナノン酸;
3−アミノ−9−シクロブチル−6−メチル−ノナノン酸;
3−アミノ−9−シクロペンチル−6−メチル−ノナノン酸;
3−アミノ−9−シクロヘキシル−6−メチル−ノナノン酸;
3−アミノ−10−シクロプロピル−6−メチル−デカノン酸;
3−アミノ−10−シクロブチル−6−メチル−デカノン酸;
3−アミノ−10−シクロペンチル−6−メチル−デカノン酸;
3−アミノ−10−シクロヘキシル−6−メチル−デカノン酸;
3−アミノ−6,8−ヂメチル−ノナノン酸;
3−アミノ−6,9−ヂメチル−デカノン酸;
(3S,6R)−3−アミノ−6−メチル−デカノン酸;
(3S,6R)−3−アミノ−6−シクロプロピル−ヘプタノン酸;
(3S,6R)−3−アミノ−6−シクロブチル−ヘプタノン酸;
(3S,6R)−3−アミノ−6−シクロペンチル−ヘプタノン酸;
(3S,6R)−3−アミノ−6−シクロヘキシル−ヘプタノン酸;
(3S,6R)−3−アミノ−7−シクロプロピル−6−メチル−ヘプタノン酸;
(3S,6R)−3−アミノ−7−シクロブチル−6−メチル−ヘプタノン酸;
(3S,6R)−3−アミノ−7−シクロペンチル−6−メチル−ヘプタノン酸;
(3S,6R)−3−アミノ−7−シクロヘキシル−6−メチル−ヘプタノン酸;
(3S,6R)−3−アミノ−8−シクロプロピル−6−メチル−オクタノン酸;
(3S,6R)−3−アミノ−8−シクロブチル−6−メチル−オクタノン酸;
(3S,6R)−3−アミノ−8−シクロペンチル−6−メチル−オクタノン酸;
(3S,6R)−3−アミノ−8−シクロヘキシル−6−メチル−オクタノン酸;
(3S,6R)−3−アミノ−9−シクロプロピル−6−メチル−ノナノン酸;
(3S,6R)−3−アミノ−9−シクロブチル−6−メチル−ノナノン酸;
(3S,6R)−3−アミノ−9−シクロペンチル−6−メチル−ノナノン酸;
(3S,6R)−3−アミノ−9−シクロヘキシル−6−メチル−ノナノン酸;
(3S,6R)−3−アミノ−10−シクロプロピル−6−メチル−デカノン酸;
(3S,6R)−3−アミノ−10−シクロブチル−6−メチル−デカノン酸;
(3S,6R)−3−アミノ−10−シクロペンチル−6−メチル−デカノン酸;
(3S,6R)−3−アミノ−10−シクロヘキシル−6−メチル−デカノン酸;
(3S,6R)−3−アミノ−6,8−ヂメチル−ノナノン酸;
(3S,6R)−3−アミノ−6,9−ヂメチル−デカノン酸;
(3S,6S)−3−アミノ−6−メチル−オクタノン酸;
(3S,6S)−3−アミノ−6−メチル−ノナノン酸;
(3S,6S)−3−アミノ−6−メチル−デカノン酸;
(3S,6S)−3−アミノ−6−シクロプロピル−ヘプタノン酸;
(3S,6S)−3−アミノ−6−シクロブチル−ヘプタノン酸;
(3S,6S)−3−アミノ−6−シクロペンチル−ヘプタノン酸;
(3S,6S)−3−アミノ−6−シクロヘキシル−ヘプタノン酸;
(3S,6S)−3−アミノ−7−シクロブチル−6−メチル−ヘプタノン酸;
(3S,6S)−3−アミノ−7−シクロペンチル−6−メチル−ヘプタノン酸;
(3S,6S)−3−アミノ−7−シクロヘキシル−6−メチル−ヘプタノン酸;
(3S,6S)−3−アミノ−8−シクロプロピル−6−メチル−オクタノン酸;
(3S,6S)−3−アミノ−8−シクロブチル−6−メチル−オクタノン酸;
(3S,6S)−3−アミノ−8−シクロペンチル−6−メチル−オクタノン酸;
(3S,6S)−3−アミノ−8−シクロヘキシル−6−メチル−オクタノン酸;
(3S,6S)−3−アミノ−9−シクロプロピル−6−メチル−ノナノン酸;
(3S,6S)−3−アミノ−9−シクロブチル−6−メチル−ノナノン酸;
(3S,6S)−3−アミノ−9−シクロペンチル−6−メチル−ノナノン酸;
(3S,6S)−3−アミノ−9−シクロヘキシル−6−メチル−ノナノン酸;
(3S,6S)−3−アミノ−10−シクロプロピル−6−メチル−デカノン酸;
(3S,6S)−3−アミノ−10−シクロブチル−6−メチル−デカノン酸;
(3S,6S)−3−アミノ−10−シクロペンチル−6−メチル−デカノン酸;
(3S,6S)−3−アミノ−10−シクロヘキシル−6−メチル−デカノン酸;
(3S,6S)−3−アミノ−6−イソプロピル−ヘプタノン酸;
(3S,6S)−3−アミノ−6,8−ヂメチル−ノナノン酸;及び
(3S,6S)−3−アミノ−6,9−ヂメチル−デカノン酸
及びそれらの医薬として許容される塩から選ばれる。
2−アミノメチル−4−メチル−7−フェニル−ヘプタノン酸;
2−アミノメチル−4−メチル−6−フェニル−ヘキサノン酸;
2−アミノメチル−7−(4−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(3−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(2−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(2,4−ヂフルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(3,4−ヂフルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−4−メチル−7−(3−トリフルオロメチル−フェニル)−ヘプタノン酸;
2−アミノメチル−4−メチル−7−(4−トリフルオロメチル−フェニル)−ヘプタノン酸;
2−アミノメチル−4−メチル−6−フェニルアミノ−ヘキサノン酸;
2−アミノメチル−4−メチル−7−フェニルアミノ−ヘプタノン酸;
2−アミノメチル−4−メチル−8−フェニルアミノ−オクタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−フェニル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−6−フェニル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−7−(4−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−(2−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−(2,4−ヂフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−(3,4−ヂフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−(2−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−(3−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−6−フェニルアミノ−ヘキサノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−フェニルアミノ−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−8−フェニルアミノ−オクタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−フェニル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−6−フェニル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−7−(4−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−(2−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−(2,4−ヂフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−(3,4−ヂフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−(2−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−(3−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−(4−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−6−フェニルアミノ−ヘキサノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−フェニルアミノ−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−8−フェニルアミノ−オクタノン酸;
(2R,4S)−2−アミノメチル−6−シクロヘキシル−4−エチル−ヘキサノン酸;
2−アミノメチル−3−(1−エチル−シクロプロピル)−プロピオン酸
2−アミノメチル−3−(1−プロピル−シクロプロピル)−プロピオン酸
2−アミノメチル−3−(1−イソプロピル−シクロプロピル)−プロピオン酸
2−アミノメチル−3−(1−ブチル−シクロプロピル)−プロピオン酸
2−アミノメチル−3−(1−イソブチル−シクロプロピル)−プロピオン酸
2−アミノメチル−3−[1−(4−メチル−ペンチル)−シクロプロピル]−プロピオン酸
2−アミノメチル−3−(1−メチル−シクロブチル)−プロピオン酸
2−アミノメチル−3−(1−エチル−シクロブチル)−プロピオン酸
2−アミノメチル−3−(1−プロピル−シクロブチル)−プロピオン酸
2−アミノメチル−3−(1−メチル−シクロペンチル)−プロピオン酸
2−アミノメチル−3−(1−エチル−シクロペンチル)−プロピオン酸
2−アミノメチル−3−(1−プロピル−シクロペンチル)−プロピオン酸
2−アミノメチル−3−(1−メチル−シクロヘキシル)−プロピオン酸
2−アミノメチル−3−(1−エチル−シクロヘキシル)−プロピオン酸
2−アミノメチル−3−(1−プロピル−シクロヘキシル)−プロピオン酸
2−アミノメチル−4−エチル−5−メチル−ヘキサノン酸
2−アミノメチル−4−エチル−ヘプタノン酸
2−アミノメチル−4−エチル−6−メチル−ヘプタノン酸
2−アミノメチル−4−エチル−オクタノン酸
2−アミノメチル−4−エチル−7−メチル−オクタノン酸
2−アミノメチル−4−エチル−ノナノン酸
2−アミノメチル−4−エチル−8−メチル−ノナノン酸
2−アミノメチル−4,4−ヂメチル−ヘプタノン酸
2−アミノメチル−4,4,8−トリメチル−ノナノン酸
2−アミノメチル−5−エチル−ヘプタノン酸
2−アミノメチル−5−エチル−6−メチル−ヘプタノン酸
2−アミノメチル−7−シクロプロピル−5−エチル−ヘプタノン酸
2−アミノメチル−7−シクロブチル−5−エチル−ヘプタノン酸
2−アミノメチル−7−シクロペンチル−5−エチル−ヘプタノン酸
2−アミノメチル−7−シクロヘキシル−5−エチル−ヘプタノン酸
2−アミノメチル−5−エチル−オクタノン酸
2−アミノメチル−5−エチル−7−メチル−オクタノン酸
2−アミノメチル−5−エチル−ノナノン酸
2−アミノメチル−5−エチル−8−メチル−ノナノン酸
2−アミノメチル−4−シクロプロピル−ブチル酸
2−アミノメチル−4−(1−メチル−シクロプロピル)−ブチル酸
2−アミノメチル−4−(1−エチル−シクロプロピル)−ブチル酸
2−アミノメチル−4−シクロブチル−ブチル酸
2−アミノメチル−4−(1−エチル−シクロブチル)−ブチル酸
2−アミノメチル−4−シクロペンチル−ブチル酸
2−アミノメチル−4−(1−メチル−シクロペンチル)−ブチル酸
2−アミノメチル−4−(1−エチル−シクロペンチル)−ブチル酸
2−アミノメチル−4−シクロヘキシル−ブチル酸
2−アミノメチル−4−(1−メチル−シクロヘキシル)−ブチル酸
2−アミノメチル−4−(1−エチル−シクロヘキシル)−ブチル酸
(2R,4S)−2−アミノメチル−6−シクロペンチル−4−エチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロブチル−4−エチル−ヘキサノン酸;及び
(2R,4S)−2−アミノメチル−6−シクロプロピル−4−エチル−ヘキサノン酸
及びそれらの医薬として許容される塩を含む。
2−アミノメチル−4−メチル−ヘキサノン酸;
2−アミノメチル−4−メチル−ヘプタノン酸;
2−アミノメチル−4−メチル−オクタノン酸;
2−アミノメチル−4−メチル−ノナノン酸;
2−アミノメチル−4−メチル−デカノン酸;
(2R,4R)−2−アミノメチル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−ノナノン酸;
(2R,4R)−2−アミノメチル−4−メチル−デカノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ノナノン酸;
(2R,4S)−2−アミノメチル−4−メチル−デカノン酸;
2−アミノメチル−5−シクロブチル−4−メチル−ペンタノン酸;
2−アミノメチル−5−シクロペンチル−4−メチル−ペンタノン酸;
2−アミノメチル−5−シクロヘキシル−4−メチル−ペンタノン酸;
2−アミノメチル−6−シクロプロピル−4−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロブチル−4−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロペンチル−4−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロヘキシル−4−メチル−ヘキサノン酸;
2−アミノメチル−7−シクロプロピル−4−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロブチル−4−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロペンチル−4−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロヘキシル−4−メチル−ヘプタノン酸;
2−アミノメチル−8−シクロプロピル−4−メチル−オクタノン酸;
2−アミノメチル−8−シクロブチル−4−メチル−オクタノン酸;
2−アミノメチル−8−シクロペンチル−4−メチル−オクタノン酸;
2−アミノメチル−8−シクロヘキシル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−5−シクロブチル−4−メチル−ペンタノン酸;
(2R,4S)−2−アミノメチル−5−シクロペンチル−4−メチル−ペンタノン酸;
(2R,4S)−2−アミノメチル−5−シクロヘキシル−4−メチル−ペンタノン酸;
(2R,4S)−2−アミノメチル−6−シクロプロピル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロブチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロペンチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロヘキシル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−7−シクロプロピル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−シクロブチル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−シクロヘキシル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−8−シクロプロピル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−8−シクロブチル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−8−シクロペンチル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−8−シクロヘキシル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−5−シクロプロピル−4−メチル−ペンタノン酸;
(2R,4R)−2−アミノメチル−5−シクロペンチル−4−メチル−ペンタノン酸;
(2R,4R)−2−アミノメチル−5−シクロヘキシル−4−メチル−ペンタノン酸;
(2R,4R)−2−アミノメチル−6−シクロプロピル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−6−シクロブチル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−6−シクロペンチル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−6−シクロヘキシル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−7−シクロブチル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−シクロペンチル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−シクロヘキシル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−8−シクロプロピル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−8−シクロブチル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−8−シクロペンチル−4−メチル−オクタノン酸;及び
(2R,4R)−2−アミノメチル−8−シクロヘキシル−4−メチル−オクタノン酸
及びそれらの医薬として許容される塩を含む。
2−アミノメチル−6−シクロプロピル−5−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロブチル−5−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロペンチル−5−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロヘキシル−5−メチル−ヘキサノン酸;
2−アミノメチル−7−シクロプロピル−5−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロブチル−5−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロペンチル−5−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロヘキシル−5−メチル−ヘプタノン酸;
2−アミノメチル−8−シクロプロピル−5−メチル−オクタノン酸;
2−アミノメチル−8−シクロブチル−5−メチル−オクタノン酸;
2−アミノメチル−8−シクロペンチル−5−メチル−オクタノン酸;
2−アミノメチル−8−シクロヘキシル−5−メチル−オクタノン酸;
2−アミノメチル−5−メチル−ヘプタノン酸;
2−アミノメチル−5−メチル−オクタノン酸;
2−アミノメチル−5−メチル−ヘプタノン酸;
2−アミノメチル−5−メチル−ノナノン酸;
(2R,6S)−2−アミノメチル−6−シクロブチル−5−メチル−ヘキサノン酸;
(2R,6S)−2−アミノメチル−6−シクロペンチル−5−メチル−ヘキサノン酸;
(2R,6S)−2−アミノメチル−6−シクロヘキシル−5−メチル−ヘキサノン酸;
(2R,6S)−2−アミノメチル−7−シクロプロピル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−7−シクロブチル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−7−シクロペンチル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−8−シクロプロピル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−8−シクロブチル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−8−シクロペンチル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−8−シクロヘキシル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−5−メチル−ノナノン酸;
(2R,6R)−2−アミノメチル−6−シクロブチル−5−メチル−ヘキサノン酸;
(2R,6R)−2−アミノメチル−6−シクロペンチル−5−メチル−ヘキサノン酸;
(2R,6R)−2−アミノメチル−6−シクロヘキシル−5−メチル−ヘキサノン酸;
(2R,6R)−2−アミノメチル−7−シクロプロピル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−7−シクロブチル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−7−シクロペンチル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−8−シクロプロピル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−8−シクロブチル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−8−シクロペンチル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−8−シクロヘキシル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−5−メチル−ヘプタノン酸;及び
(2R,6R)−2−アミノメチル−5−メチル−ノナノン酸
及びそれらの医薬として許容される塩を含む。
1)例えば、エステラーゼ又はリパーゼにより切断されうるエステル又はアミド誘導体。エステル誘導体については、上記エステルは既知の方法により薬物分子のカルボン酸基に由来する。アミド誘導体については、上記アミドは既知の方法により薬物分子のカルボン酸基又はアミン基に由来しうる。
2)特定の又は非特定のプロテイナーゼにより認識されうるペプチド。ペプチドは既知の方法により薬物分子のアミン又はカルボン酸基とのアミド結合形成を介して薬物分子に結合されうる。
3)プロドラッグ形又は改変されたプロドラッグ形の膜選択をとおして活動部位に蓄積する誘導体。
4)1〜3のいずれかの組み合わせ
でありうる。
本発明に係る化合物は以下に示されるように調製されうる。以下の反応スキーム及び議論において、構造式I、IA、IA−1、IA−2、IB、IC、II、IIA、III、及びIV、並びにラヂカルR1、R2、R3、R4、R5及びR6は、別段の定めなき限り、上記のように定義される。
3−アミノ−6−シクロプロピル−5−メチル−ヘキサノン酸;
3−アミノ−6−シクロブチル−5−メチル−ヘキサノン酸;
3−アミノ−6−シクロペンチル−5−メチル−ヘキサノン酸;
3−アミノ−6−シクロヘキシル−5−メチル−ヘキサノン酸;
3−アミノ−7−シクロプロピル−5−メチル−ヘプタノン酸;
3−アミノ−7−シクロブチル−5−メチル−ヘプタノン酸;
3−アミノ−7−シクロペンチル−5−メチル−ヘプタノン酸;
3−アミノ−7−シクロヘキシル−5−メチル−ヘプタノン酸;
3−アミノ−8−シクロプロピル−5−メチル−オクタノン酸;
3−アミノ−8−シクロブチル−5−メチル−オクタノン酸;
3−アミノ−8−シクロヘキシル−5−メチル−オクタノン酸;
3−アミノ−6−シクロプロピル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−6−シクロブチル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−6−シクロペンチル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−6−シクロヘキシル−5,5−ヂメチル−ヘキサノン酸;
3−アミノ−7−シクロプロピル−5,5−ヂメチル−ヘプタノン酸;
3−アミノ−7−シクロブチル−5,5−ヂメチル−ヘプタノン酸;
3−アミノ−7−シクロペンチル−5,5−ヂメチル−ヘプタノン酸;及び
3−アミノ−7−シクロヘキシル−5,5−ヂメチル−ヘプタノン酸
を含む。
Stephen G.; and Smith, Andrew D, J. Chem. Soc., Perkin Trans. 1, 2001,22,2931−2938により示される方法にしたがって、約−78℃の温度で、テトラヒドロフラン中でのn−ブチル−リチウムでの脱プロトン化後、(R)−(+)−N−ベンジル−α−メチルベンジルアミン、(S)−(−)−N−ベンジル−α−メチルベンジルアミンのいずれかを用いて行われる。好ましくは、この反応は、Bull, Steven D.; Davies, Stephen G.; and Smith, Andrew D, J, Chem. Soc., Perkin Trans. 1, 2001, 22,2931−2938により示される方法にしたがって、約−78℃の温度で、テトラヒドロフラン中のn−ブチル−リチウムでの脱プロトン化後、(R)−(+)−N−ベンジル−α−メチルベンジルアミン又は(S)−(−)−N−ベンジル−α−メチルベンジルアミンのいずれかを用いて行われる。
(3S,5R)−3−アミノ−6−シクロプロピル−5−メチル−ヘキサノン酸;
(3S,5R)−3−アミノ−6−シクロブチル−5−メチル−ヘキサノン酸;
(3S,5R)−3−アミノ−6−シクロペンチル−5−メチル−ヘキサノン酸;
(3S,5R)−3−アミノ−6−シクロヘキシル−5−メチル−ヘキサノン酸;
(3S,5R)−3−アミノ−8−シクロプロピル−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−シクロブチル−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−シクロペンチル−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−8−シクロヘキシル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−6−シクロプロピル−5−メチル−ヘキサノン酸;
(3S,5S)−3−アミノ−6−シクロブチル−5−メチル−ヘキサノン酸;
(3S,5S)−3−アミノ−6−シクロペンチル−5−メチル−ヘキサノン酸;
(3S,5S)−3−アミノ−6−シクロヘキシル−5−メチル−ヘキサノン酸;
(3S,5S)−3−アミノ−8−シクロプロピル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−シクロブチル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−シクロペンチル−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−8−シクロヘキシル−5−メチル−オクタノン酸;
(3S)−3−アミノ−6−シクロプロピル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−6−シクロブチル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−6−シクロペンチル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−6−シクロヘキシル−5,5−ヂメチル−ヘキサノン酸;
(3S)−3−アミノ−7−シクロプロピル−5,5−ヂメチル−ヘプタノン酸;
(3S)−3−アミノ−7−シクロブチル−5,5−ヂメチル−ヘプタノン酸;
(3S)−3−アミノ−7−シクロペンチル−5,5−ヂメチル−ヘプタノン酸;及び
(3S)−3−アミノ−7−シクロヘキシル−5,5−ヂメチル−ヘプタノン酸
を含む。
約50℃〜上記反応混合物のおよそ還流温度の温度で、トルエン、ベンゼン又はTHFの如き好適な溶媒中で、t−ブタノール、ベンジルアルコール又はp−メトキシベンジルアルコールの如き好適なアルコールの存在下でのヂフェニルフォスフォリルアジドでの式12の化合物の処理は、R5がメチル、エチル、t−ブチル、ベンジル又はp−メトキシベンジルである、式13の対応する化合物を与える。R5は使用されるアルコールの選択に因る。好ましくは、この反応は還流条件下でp−メトキシベンジルアルコールの存在下でトルエン溶媒を用いて行われる。
Wiley, 1991を参照のこと)。例えば、この反応はおよそ室温〜上記反応混合物のおよそ還流温度の温度で、好ましくは還流温度で、塩酸又は硫酸の如き適切な酸での処理により又はおよそ室温〜およそ還流温度で、好ましくはおよそ室温で、水酸化ナトリウム、水酸化カリウム又は水酸化リチウム、好ましくは水酸化ナトリウムの如き適切な無機塩基での処理により、加水分解条件下で行われうる。この反応は好ましくは還流温度で塩酸を用いて行われる。しかしながら、PGがt−ブチルであるとき、上記反応は好ましくはトリフルオロ酢酸(TFA)中で行われる。PGが塩基性基であるとき、上記加水分解は当業者に周知の方法を用いて、例えば、水酸化ナトリウム又はカリウムを用いて、塩基性条件下で行われうる。
(3S,5R)−3−アミノ−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−5−メチル−オクタノン酸;
(3S,5R)−3−アミノ−5−メチル−ノナノン酸;
(3S,5R)−3−アミノ−5−メチル−デカノン酸;
(3S,5S)−3−アミノ−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−5−メチル−オクタノン酸;
(3S,5S)−3−アミノ−5−メチル−ノナノン酸;
(3S,5S)−3−アミノ−5−メチル−デカノン酸;
(3S)−3−アミノ−5,5−ヂメチル−ヘプタノン酸;
(3S)−3−アミノ−5,5−ヂメチル−オクタノン酸;
(3S)−3−アミノ−5,5−ヂメチル−ノナノン酸;
(3S)−3−アミノ−5,5−ヂメチル−デカノン酸;
(3S,5R)−3−アミノ−7−シクロブチル−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−7−シクロペンチル−5−メチル−ヘプタノン酸;
(3S,5R)−3−アミノ−7−シクロヘキシル−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−7−シクロプロピル−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−7−シクロブチル−5−メチル−ヘプタノン酸;
(3S,5S)−3−アミノ−7−シクロペンチル−5−メチル−ヘプタノン酸;及び
(3S,5S)−3−アミノ−7−シクロヘキシル−5−メチル−ヘプタノン酸
を含む。
(2R,4R)−2−アミノメチル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−ノナノン酸;
(2R,4R)−2−アミノメチル−4−メチル−デカノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ノナノン酸;
(2R,4S)−2−アミノメチル−4−メチル−デカノン酸;
(2R,4S)−2−アミノメチル−6−シクロプロピル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロブチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロペンチル−4−メチル−ヘキサノン酸;及び
(2R,4S)−2−アミノメチル−6−シクロヘキシル−4−メチル−ヘキサノン酸
を含む。
et al Tetrahedron Asymm., 7,(8),1996,2233及びSeebach et al, Eur. J. Org. Chem., 1999, 335により又はArvanitis et al, J. Chem. Soc. Perkin Trans 1., 1998, 521により示されるものを含む:
“A New And Sensitive Method For Measuring Thermal Nociception In Cutaneous Hyperalgesia”. Pain. 32:77−88, 1988を参照のこと)、不安(Vogel JR, Beer B, and Clody DE, “A Simple And Reliable Conflict Procedure For Testing Anti−Anxiety Agents”, Psychophamacologia 21:1−7,1971)の動物モデルにおいて決定されうる。
実施例1.塩酸(3S,5R)−3−アミノ−5−メチル−オクタノン酸
(R)−2,6−ヂメチル−ノン−2−エン。0℃でTHF(800mL)中の臭化(S)−シトロネルリル(50g、0.228mol)にLiCl(4.3g)、続いてCuCl2(6.8g)を添加した。30分後、塩化メチルマグネシウム(152mLのTHF中の3M溶液、Aldrich)を添加し、及び上記溶液を室温まで温めた。10時間後、上記溶液を0℃まで冷却し、及び飽和水性塩化アンモニウム溶液を注意深く添加した。生ずる2層を分離し、及び上記水相をエーテルで抽出した。混合した有機相を乾燥させ(MgSO4)、及び濃縮させて、(R)−2,6−ヂメチル−ノン−2−エンを得た。32.6g;93%。さらなる精製なしに使用した。
メタンスルフォン酸(S)−3,7−ヂメチル−オクト−6−エニルエステル。0℃でCH2Cl2(800mL)中のS−(−)−シトロネルロール(42.8g、0.274mol)及びトリエチルアミン(91mL、0.657mol)にCH2Cl2(200mL)中の塩化メタンスルフォニル(26mL、0.329mol)を添加した。0℃で2時間後、上記溶液を1N HCl、その後塩水で洗浄した。上記有機相を乾燥させ(MgSO4)、及び濃縮させ、上記表題の化合物、油(60.5g、94%)を得、それをさらなる精製なしに使用した。MS,m/z(比較強度):139[100%],143[100%]。
(4R,5S)−4−メチル−3−((R)−4−メチル−ヘプタノイル)−5−フェニル−オキサゾリヂン−2−オンの合成と同様の手順を利用し、上記表題の化合物を油(35.7g、95%)として得た。MS,m/z(比較強度):
(R)−4−メチル−オクタノン酸。塩化リチウム(0.39g、9.12mmol)及び塩化銅(I)(0.61g、4.56mmol)を環境温度で45mLのTHF中に混合し、及び15分間攪拌し、その後0℃まで冷却し、そのとき臭化エチルマグネシウム(THF中1M溶液、45mL、45mmol)を添加した。臭化(S)−シトロネルリル(5.0g、22.8mmol)を一滴ずつ添加し、及び上記溶液を一晩攪拌しながら環境温度までゆっくり温めた。上記反応を飽和NH4Cl(水性)の注意深い添加により停止させ、及びEt2O及び飽和NH4Cl(水性)で30分間攪拌した。上記相を分離し、及び上記有機相を乾燥させ(MgSO4)、及び濃縮させた。上記粗い(R)−2,6−ヂメチル−デク−2−エンを精製なしに使用した。0℃で50mLアセトン中の(R)−2,6−ヂメチル−デク−2−エン(3.8g、22.8mmol)の溶液にJones’試薬(H2SO4(水性)中2.7M、40mL、108mmol)を添加し、及び上記溶液を一晩攪拌しながら環境温度までゆっくり温めた。上記混合物をEt2O及びH2Oの間で分割し、上記相を分離し、及び上記有機相を塩水で洗浄し、乾燥させ(MgSO4)、及び濃縮させた。上記残留物をフラッシュクロマトグラフィー(8:1 ヘキサン:EtOAc)により精製し、2.14g(59%)の上記表題の化合物を無色の油として得た:LRMS:m/z 156.9(M+);1H NMR(400MHz;CDCl3):δ2.33(m,2H),1.66(m,1H),1.43(m,2H),1.23(m,5H),1.10(m,1H),0.86(m,6H)。Jones’試薬を26.7g CrO3、23mL H2SO4を混合し、及びH2Oで100mLに希釈することにより2.7M溶液として調製した。
5R−メチル−3R−(4S−メチル−2−オキソ−5R−フェニルオキサゾリヂン−3−カルボニル)オクタノン酸。ヂクロロメタン(150mL)中の(3R,5R)−5−メチル−3−((4S,5R)−4−メチル−2−オキソ−5−フェニル−オキサゾリヂン−3−カルボニル)−オクタノン酸第三−ブチルエステル(3.9g、9.34mmol)の溶液をトリフルオロ酢酸(7.21mL、93.4mL)で処理し、及び環境温度で18時間攪拌した。上記溶媒及び試薬をin vacuoで除去した後、生ずる残留物を100mLヘキサン中で粉砕し、3.38gの上記表題の化合物(100%)mp 142〜143℃を得た。
2−シアノ−4,4−ヂメチル−ヘプタ−2,6−ヂエノン酸エチルエステル。170mLのトルエン中の2,2−ヂメチル−ペント−4−エナル(5.0g、44mmol)、シアノ−酢酸エチルエステル(5.12mL、48mmol)、ピペリヂン(1.3mL、14mmol)及び酢酸(4.52mL、80mmol)の溶液をDean−Starkセパレーターで装備したフラスコ中で還流下で18時間熱した。何mLかの水をトラップ中に回収した。上記反応を冷却し、及び1N HCl、NaHCO3及び塩水で連続して洗浄した。上記有機層をNa2SO4上で乾燥させ、及び油になるまで濃縮させた。この油をヘキサン中の20%EtOAcで溶離してクロマトグラフィーにかけ、2ロットの組み合わせ、全部で8.3g(91%)を得た。
3−(4,4−ヂメチル−ヘプタノイル)−(R)−4−メチル−(S)−5−フェニル−オキサゾリヂン−2−オン:50mL THF中の4,4−ヂメチル−ヘプタノン酸(1.58g、10mmol)及びトリエチルアミン(4.6mL)の溶液を0℃まで冷却し、及び塩化2,2−ヂメチル−プロピオニル(1.36mL)で処理した。1時間後、4R−メチル−5S−フェニル−オキサゾリヂン−2−オン(1.95g、11mmol)及び塩化リチウム(0.47g、11mmol)を添加し、及び上記混合物を18時間攪拌した。上記沈殿物をろ過し、及び追加のTHFで完全に洗浄した。上記ろ過物をin
vacuoで濃縮させ、油っぽい固体を得た。この固体を200mL Et2O中に溶解し、飽和NaHCO3、0.5N HCl及び飽和NaClで連続して洗浄し、乾燥させ(MgSO4)、及びin vacuoで濃縮させ、上記表題の化合物を油(3.0g、95%)として得た。
2−シアノ−3−(1−メチル−シクロプロピル)−アクリル酸エチルエステル。50mL CH2Cl2中の1−メチルシクロプロパン−メタノール(Aldrich、1.13mL、11.6mmol)に天然アルミニウム(2.5g)、及びその後PCC(2.5g、11.6mmol)を添加し、及び上記混合物を環境温度で3時間攪拌した。上記混合物を吸引下でシリカゲルの1cmプラグをとおしてろ過し、及びEt2Oですすいだ。上記ろ過物をca.5mL総容積になるまで濃縮させた。上記残留物にTHF(10mL)、シアノ酢酸エチル(1.2mL、11.3mmol)、ピペリヂン(5滴)、及び最後に酢酸(5滴)を添加した。上記全体を環境温度で一晩攪拌し、その後Et2O及び飽和水性NaHCO3の間で分割した。上記相を分離し、及び上記有機相を塩水で洗浄し、乾燥させ(MgSO4)、及び濃縮させた。残留物のフラッシュクロマトグラフィー(10→15% EtOAc/ヘキサン)は0.53g(25%)のエステルを無色の油として与え、それを静止させて結晶化させた;mp35〜37℃。
(5S)−5−メチル−オクタ−2,6−ヂエノン酸第三−ブチルエステル。−78℃で30mLトルエン中の(S)−3−メチル−ヘキス−4−エノン酸エチルエステル(1.0g、6.4mmol)の溶液にDIBAH(THF中1.0M、6.4mL)を一滴ずつ5分間にわたり添加した。上記混合物を−78℃で45分間攪拌し、そのとき5滴のメタノールを添加し、激しいH2放出を生じた。メタノールを、気体放出が観察されなくなるまで添加した(ca.5mL)。このとき、冷浴を除去し、及びca.5mLの飽和水性Na+K+酒石酸を添加した。上記混合物が室温に達したとき、追加の飽和水性Na+K+酒石酸及びEt2Oを添加し、及び上記相がほとんど透明になるまで攪拌を続けた(ca.1時間)。上記相を分離し、及び上記有機相を塩水で洗浄し、乾燥させ(MgSO4)、及び揮発性の懸念のためにca.10mL総容積になるまで濃縮させた。上記粗い混合物を上記に示される方法により10mmolのエステルから調製した追加のバッチのアルデヒドと混合し、及び上記全体を精製なしに使用した。25mL THF中のナトリウムヒドリド(鉱油中60%分散)の懸濁物にt−ブチル−P,P−ヂメチルフォスフォノ酢酸(3.0mL、15mmol)を、H2の放出が制御下に置かれるよう、一滴ずつ1時間にわたり添加した。上記添加が完了した後、トルエン中の粗いアルデヒド(ca.20mL総容積)をすばやく一滴ずつ添加し、及び上記混合物を環境温度で一晩攪拌した。上記混合物をEt2O及び飽和水性NH4Clの間で分割し、上記相を分離し、上記有機相を塩水で洗浄し、乾燥させ(MgSO4)、及び濃縮させた。残留物のフラッシュクロマトグラフィー(0→3→5% EtOAc/ヘキサン)は1.0g(29%、2段階)の不飽和エステルを薄黄色油として与えた:
2−アミノメチル−4,4,8−トリメチル−ノナノン酸の手順と同様の手順を6−メチル−1−ヘプタノールから2−アミノメチル−8−メチル−ノナノン酸を調製するために利用した m/z 202.1(M+)。
(R)−2,6−ヂメチルヘプタン−1−オール:マグネシウムturnings(2.04g、84mmol)及びヨー素の結晶を、1−ブロモ−3−メチルブタン(0.3mL、ストレート)の添加のために5mL THF中に懸濁した。上記混合物をGrignard形成を開始させるために熱した。残りの1−ブロモ−3−メチルブタン(8.63mL、72mmol)をTHF(60mL)中に希釈し、及び一滴ずつ添加した。上記混合物を環境温度で2時間攪拌し、及び−5℃まで冷却した。THF(50mL)中の塩化銅(1.21g、9mmol)及びLiCl(0.76g、18mmol)の溶液を温度を0℃未満に保ちながら一滴ずつ添加した。生ずる混合物を20分間攪拌し、及びTHF(20mL)中の(R)−3−ブロモ−2−メチルプロパノールを、温度を0℃未満に保ちながら一滴ずつ添加した。上記混合物を一晩で環境温度にゆっくり到達させた。上記反応混合物を水酸化アンモニウム及び水で停止させた。上記混合物をEtOAcで希釈し、及び3×20mL EtOAcで抽出した。上記有機物を塩水で洗浄し、乾燥させ(MgSO4)、ろ過し、及び濃縮させた。上記残留の油をシリカゲルクロマトグラフィー(90/10 ヘキサン/EtOAc)を介して精製し、2.67g(R)−2,6−ヂメチルヘプタン−1−オールを得た。
(4R,5S)−4−メチル−3−(R)−4−メチル−ヘプタノイル)−5−オキサゾリヂン−2−オンと同様の手順を利用して3−(4R,8−ヂメチル−ノナノイル)−4(S)−メチル−5(R)−フェニル−オキサゾリヂン−2−オン(1.35g)を得た
m/z 346.5(M+)。
2,2,6−トリメチル−ヘプタノン酸メチルエステル:−78℃でTHF(22mL)中のヂイソプロピルアミン(1.54mL、11.03mmol)にnBuLi(6.89mLのヘキサン中1.6M溶液)を添加した。上記溶液を−78℃で30分間攪拌し、続いてメチルイソブチル酸塩(0.97mL、8.48mmol)を添加した。上記混合物を−78℃で2時間攪拌し、及びその後THF(6mL)中の1−ヨード−4−メチルペンタン(1.8g、8.48mmol)及びDMPU(0.55mL、4.24mmol)を添加した。上記反応を−78℃で攪拌し、及び16時間にわたり環境温度にゆっくり到達させた。上記反応を塩化アンモニウム(飽和水性溶液)の添加により停止させ、及び上記混合物をEtOAc(2×10mL)で抽出した。上記有機物を混合し、水で洗浄し、乾燥させ(MgSO4)、ろ過し、及び濃縮させた。シリカゲルクロマトグラフィー(99/1 ヘキサン/EtOAc)は1.57gの2,2,6−トリメチル−ヘプタノン酸メチルエステルを与えた。
2−アミノメチル−4,4,8−トリメチル−ノナノン酸の手順と同様の手順を利用して2−エチルヘキサナールから2−アミノメチル−4−エチル−オクタノン酸を調製した。m/z 202.1(M+)。
2−アミノメチル−4,4,8−トリメチル−ノナノン酸の手順と同様の手順を利用して2,6−ヂ−t−ブチル−4−メチルフェニル シクロプロピルカルボキシレートから2−アミノメチル−8−メチル−ノナノン酸を調製した。m/z 230.2(M+)。
2−アミノメチル−4,4,8−トリメチル−ノナノン酸の手順と同様の手順を利用して2,6−ヂ−t−ブチル−4−メチルフェニルシクロプロピルカルボキシレートから2−アミノメチル−8−メチル−ノナノン酸を調製した。m/z 228.2(M+)。
2−アミノメチル−4,8−ヂメチル−ノナノン酸と同様の手順を使用して4−エチルヘキサノン酸から2−アミノメチル−4−エチル−ヘキサノン酸を調製した。m/z 174.1。
2−メチル−プロパン−2(S)−スルフィン酸(1,3−ヂメチル−ペンチリデン)−アミド:(S)−(−)−2−メチル−2−プロパンスルフォンアミド(500mg、4.1mmol)、4−メチル−2−ヘキサノン(470mg、4.1mmol)、及びチタン(IV)エトキシド(1.7mL、8.3mmol)の溶液を還流で18時間熱した。上記反応混合物をすばやく攪拌しながら20mL塩水中に注いだ。生ずる溶液をceliteをとおしてろ過し、及び上記有機層を分離した。上記水層を酢酸エチル(2×20mL)で抽出した。上記混合した有機物を乾燥させ(Na2SO4)、ろ過し、及び濃縮させた。生ずる油をシリカゲルクロマトグラフィー(ヘキサン中の25% EtOAc)により精製し、575mgの2−メチル−プロパン−2(S)−スルフィン酸(1,3−ヂメチル−ペンチリデン)−アミドを黄色油として得た。
3(S)−アミノ−3,5−ヂメチル−ヘプタノン酸の手順と同様の手順を使用して3(S)−アミノ−3,5−ヂメチル−ノナノン酸を調製した。m/z 202.1(C11H23NO2+H)。
3(S)−アミノ−3,5−ヂメチル−ヘプタノン酸の手順と同様の手順を使用して3(S)−アミノ−3,5−ヂメチル−ノナノン酸を調製した。m/z 188.1(C10H21NO2+H)。
Claims (10)
- 以下の式II:
R2は、水素又は、1〜5のフッ素原子で場合により置換される(C1−C3)アルキルである;
R3は(C1−C6)アルキル、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C3)アルキル、フェニル、フェニル−(C1−C3)アルキル、ピリヂル、ピリヂル−(C1−C3)アルキル、フェニル−N(H)−又はピリヂル−N(H)−である、ここで、上記アルキル基のそれぞれは1〜5のフッ素原子で場合により置換され、及びここで、前記フェニル及び前記ピリヂル基のそれぞれは、クロロ、フルオロ、アミノ、ニトロ、シアノ、(C1−C3)アルキルアミノ、1〜3のフッ素原子で場合により置換される(C1−C3)アルキル及び1〜3のフッ素原子で場合により置換される(C1−C3)アルコキシから独立に選ばれる1〜3の置換基で場合により置換される;
但し、R1が水素であるとき、R2は水素ではない。}により表される化合物又は医薬として許容されるその塩。 - 以下の式IIA:
- 以下の:
2−アミノメチル−4−メチル−7−フェニル−ヘプタノン酸;
2−アミノメチル−4−メチル−6−フェニル−ヘキサノン酸;
2−アミノメチル−7−(4−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(3−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(2−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(2,4−ジフルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−7−(3,4−ジフルオロ−フェニル)−4−メチル−ヘプタノン酸;
2−アミノメチル−4−メチル−7−(2−トリフルオロメチル−フェニル)−ヘプタノン酸;
2−アミノメチル−4−メチル−7−(3−トリフルオロメチル−フェニル)−ヘプタノン酸;
2−アミノメチル−4−メチル−7−(4−トリフルオロメチル−フェニル)−ヘプタノン酸;
2−アミノメチル−4−メチル−6−フェニルアミノ−ヘキサノン酸;
2−アミノメチル−4−メチル−7−フェニルアミノ−ヘプタノン酸;
2−アミノメチル−4−メチル−8−フェニルアミノ−オクタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−フェニル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−6−フェニル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−7−(4−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−(3−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−(2−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−(2,4−ジフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−(3,4−ジフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−(2−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−(3−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−(4−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−6−フェニルアミノ−ヘキサノン酸;
(2R,4R)−2−アミノメチル−4−メチル−7−フェニルアミノ−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−8−フェニルアミノ−オクタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−フェニル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−6−フェニル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−7−(4−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−(3−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−(2−フルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−(2,4−ジフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−(3,4−ジフルオロ−フェニル)−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−(2−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−(3−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−(4−トリフルオロメチル−フェニル)−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−6−フェニルアミノ−ヘキサノン酸;
(2R,4S)−2−アミノメチル−4−メチル−7−フェニルアミノ−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−8−フェニルアミノ−オクタノン酸;
(2R,4S)−2−アミノメチル−6−シクロヘキシル−4−エチル−ヘキサノン酸;
2−アミノメチル−4−エチル−ヘキサノン酸;
2−アミノメチル−4−エチル−5−メチル−ヘキサノン酸;
2−アミノメチル−4−エチル−ヘプタノン酸;
2−アミノメチル−4−エチル−6−メチル−ヘプタノン酸;
2−アミノメチル−4−エチル−オクタノン酸;
2−アミノメチル−4−エチル−7−メチル−オクタノン酸;
2−アミノメチル−4−エチル−ノナノン酸;
2−アミノメチル−4−エチル−8−メチル−ノナノン酸;
2−アミノメチル−4,4−ジメチル−ヘプタノン酸;
2−アミノメチル−4,6−ジメチル−ヘプタノン酸;
2−アミノメチル−4,4,8−トリメチル−ノナノン酸;
(2R,4S)−2−アミノメチル−6−シクロペンチル−4−エチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロブチル−4−エチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロプロピル−4−エチル−ヘキサノン酸;
2−アミノメチル−4−メチル−ヘキサノン酸;
2−アミノメチル−4−メチル−ヘプタノン酸;
2−アミノメチル−4−メチル−オクタノン酸;
2−アミノメチル−4−メチル−ノナノン酸;
2−アミノメチル−4−メチル−デカノン酸;
(2R,4R)−2−アミノメチル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−4−メチル−ノナノン酸;
(2R,4R)−2−アミノメチル−4−メチル−デカノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−4−メチル−ノナノン酸;
(2R,4S)−2−アミノメチル−4−メチル−デカノン酸;
2−アミノメチル−5−シクロプロピル−4−メチル−ペンタノン酸;
2−アミノメチル−5−シクロブチル−4−メチル−ペンタノン酸;
2−アミノメチル−5−シクロペンチル−4−メチル−ペンタノン酸;
2−アミノメチル−5−シクロヘキシル−4−メチル−ペンタノン酸;
2−アミノメチル−6−シクロプロピル−4−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロブチル−4−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロペンチル−4−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロヘキシル−4−メチル−ヘキサノン酸;
2−アミノメチル−7−シクロプロピル−4−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロブチル−4−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロペンチル−4−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロヘキシル−4−メチル−ヘプタノン酸;
2−アミノメチル−8−シクロプロピル−4−メチル−オクタノン酸;
2−アミノメチル−8−シクロブチル−4−メチル−オクタノン酸;
2−アミノメチル−8−シクロペンチル−4−メチル−オクタノン酸;
2−アミノメチル−8−シクロヘキシル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−5−シクロプロピル−4−メチル−ペンタノン酸;
(2R,4S)−2−アミノメチル−5−シクロブチル−4−メチル−ペンタノン酸;
(2R,4S)−2−アミノメチル−5−シクロペンチル−4−メチル−ペンタノン酸;
(2R,4S)−2−アミノメチル−5−シクロヘキシル−4−メチル−ペンタノン酸;
(2R,4S)−2−アミノメチル−6−シクロプロピル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロブチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロペンチル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−6−シクロヘキシル−4−メチル−ヘキサノン酸;
(2R,4S)−2−アミノメチル−7−シクロプロピル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−シクロブチル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−シクロペンチル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−7−シクロヘキシル−4−メチル−ヘプタノン酸;
(2R,4S)−2−アミノメチル−8−シクロプロピル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−8−シクロブチル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−8−シクロペンチル−4−メチル−オクタノン酸;
(2R,4S)−2−アミノメチル−8−シクロヘキシル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−5−シクロプロピル−4−メチル−ペンタノン酸;
(2R,4R)−2−アミノメチル−5−シクロブチル−4−メチル−ペンタノン酸;
(2R,4R)−2−アミノメチル−5−シクロペンチル−4−メチル−ペンタノン酸;
(2R,4R)−2−アミノメチル−5−シクロヘキシル−4−メチル−ペンタノン酸;
(2R,4R)−2−アミノメチル−6−シクロプロピル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−6−シクロブチル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−6−シクロペンチル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−6−シクロヘキシル−4−メチル−ヘキサノン酸;
(2R,4R)−2−アミノメチル−7−シクロプロピル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−シクロブチル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−シクロペンチル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−7−シクロヘキシル−4−メチル−ヘプタノン酸;
(2R,4R)−2−アミノメチル−8−シクロプロピル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−8−シクロブチル−4−メチル−オクタノン酸;
(2R,4R)−2−アミノメチル−8−シクロペンチル−4−メチル−オクタノン酸;及び
(2R,4R)−2−アミノメチル−8−シクロヘキシル−4−メチル−オクタノン酸、
から選ばれる請求項1に記載の化合物又は医薬として許容されるその塩。 - 以下の式III:
- 以下の式IV:
R3は(C1−C6)アルキル、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C3)アルキル、フェニル、フェニル−(C1−C3)アルキル、ピリヂル、ピリヂル−(C1−C3)アルキル、フェニル−N(H)−又はピリヂル−N(H)−である、ここで、上記アルキル基のそれぞれは1〜5のフッ素原子で場合により置換され、及びここで、前記フェニル及び前記ピリヂル基のそれぞれは、クロロ、フルオロ、アミノ、ニトロ、シアノ、(C1−C3)アルキルアミノ、1〜3のフッ素原子で場合により置換される(C1−C3)アルキル及び1〜3のフッ素原子で場合により置換される(C1−C3)アルコキシから選ばれる1〜3の置換基で場合により置換される。}で表される化合物又は医薬として許容されるその塩。 - 以下の:
2−アミノメチル−5−エチル−ヘプタノン酸;
2−アミノメチル−5−エチル−6−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロプロピル−5−エチル−ヘプタノン酸;
2−アミノメチル−7−シクロブチル−5−エチル−ヘプタノン酸;
2−アミノメチル−7−シクロペンチル−5−エチル−ヘプタノン酸;
2−アミノメチル−7−シクロヘキシル−5−エチル−ヘプタノン酸;
2−アミノメチル−5−エチル−オクタノン酸;
2−アミノメチル−5−エチル−7−メチル−オクタノン酸;
2−アミノメチル−5−エチル−ノナノン酸;
2−アミノメチル−5−エチル−8−メチル−ノナノン酸;
2−アミノメチル−6−シクロプロピル−5−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロブチル−5−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロペンチル−5−メチル−ヘキサノン酸;
2−アミノメチル−6−シクロヘキシル−5−メチル−ヘキサノン酸;
2−アミノメチル−7−シクロプロピル−5−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロブチル−5−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロペンチル−5−メチル−ヘプタノン酸;
2−アミノメチル−7−シクロヘキシル−5−メチル−ヘプタノン酸;
2−アミノメチル−8−シクロプロピル−5−メチル−オクタノン酸;
2−アミノメチル−8−シクロブチル−5−メチル−オクタノン酸;
2−アミノメチル−8−シクロペンチル−5−メチル−オクタノン酸;
2−アミノメチル−8−シクロヘキシル−5−メチル−オクタノン酸;
2−アミノメチル−5−メチル−ヘプタノン酸;
2−アミノメチル−5−メチル−オクタノン酸;
2−アミノメチル−5−メチル−ノナノン酸;
2−アミノメチル−8−メチル−ノナノン酸;
(2R,6S)−2−アミノメチル−6−シクロプロピル−5−メチル−ヘキサノン酸;
(2R,6S)−2−アミノメチル−6−シクロブチル−5−メチル−ヘキサノン酸;
(2R,6S)−2−アミノメチル−6−シクロペンチル−5−メチル−ヘキサノン酸;
(2R,6S)−2−アミノメチル−6−シクロヘキシル−5−メチル−ヘキサノン酸;
(2R,6S)−2−アミノメチル−7−シクロプロピル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−7−シクロブチル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−7−シクロペンチル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−7−シクロヘキシル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−8−シクロプロピル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−8−シクロブチル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−8−シクロペンチル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−8−シクロヘキシル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−5−メチル−ヘプタノン酸;
(2R,6S)−2−アミノメチル−5−メチル−オクタノン酸;
(2R,6S)−2−アミノメチル−5−メチル−ノナノン酸;
(2R,6R)−2−アミノメチル−6−シクロプロピル−5−メチル−ヘキサノン酸;
(2R,6R)−2−アミノメチル−6−シクロブチル−5−メチル−ヘキサノン酸;
(2R,6R)−2−アミノメチル−6−シクロペンチル−5−メチル−ヘキサノン酸;
(2R,6R)−2−アミノメチル−6−シクロヘキシル−5−メチル−ヘキサノン酸;
(2R,6R)−2−アミノメチル−7−シクロプロピル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−7−シクロブチル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−7−シクロペンチル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−7−シクロヘキシル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−8−シクロプロピル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−8−シクロブチル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−8−シクロペンチル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−8−シクロヘキシル−5−メチル−オクタノン酸;
(2R,6R)−2−アミノメチル−5−メチル−ヘプタノン酸;
(2R,6R)−2−アミノメチル−5−メチル−オクタノン酸;及び
(2R,6R)−2−アミノメチル−5−メチル−ノナノン酸、
から選ばれる請求項5に記載の化合物又は医薬として許容されるその塩。 - 以下の:
2−アミノメチル−3−(1−メチル−シクロプロピル)−プロピオン酸;
2−アミノメチル−3−(1−エチル−シクロプロピル)−プロピオン酸;
2−アミノメチル−3−(1−プロピル−シクロプロピル)−プロピオン酸;
2−アミノメチル−3−(1−イソプロピル−シクロプロピル)−プロピオン酸;
2−アミノメチル−3−(1−ブチル−シクロプロピル)−プロピオン酸;
2−アミノメチル−3−(1−イソブチル−シクロプロピル)−プロピオン酸;
2−アミノメチル−3−[1−(4−メチル−ペンチル)−シクロプロピル]−プロピオン酸;
2−アミノメチル−3−(1−メチル−シクロブチル)−プロピオン酸;
2−アミノメチル−3−(1−エチル−シクロブチル)−プロピオン酸;
2−アミノメチル−3−(1−プロピル−シクロブチル)−プロピオン酸;
2−アミノメチル−3−(1−メチル−シクロペンチル)−プロピオン酸;
2−アミノメチル−3−(1−エチル−シクロペンチル)−プロピオン酸;
2−アミノメチル−3−(1−プロピル−シクロペンチル)−プロピオン酸;
2−アミノメチル−3−(1−メチル−シクロヘキシル)−プロピオン酸;
2−アミノメチル−3−(1−エチル−シクロヘキシル)−プロピオン酸;
2−アミノメチル−3−(1−プロピル−シクロヘキシル)−プロピオン酸;
2−アミノメチル−4−シクロプロピル−酪酸;
2−アミノメチル−4−(1−メチル−シクロプロピル)−酪酸;
2−アミノメチル−4−(1−エチル−シクロプロピル)−酪酸;
2−アミノメチル−4−シクロブチル−酪酸;
2−アミノメチル−4−(1−メチル−シクロブチル)−酪酸;
2−アミノメチル−4−(1−エチル−シクロブチル)−酪酸;
2−アミノメチル−4−シクロペンチル−酪酸;
2−アミノメチル−4−(1−メチル−シクロペンチル)−酪酸;
2−アミノメチル−4−(1−エチル−シクロペンチル)−酪酸;
2−アミノメチル−4−シクロヘキシル−酪酸;
2−アミノメチル−4−(1−メチル−シクロヘキシル)−酪酸;及び
2−アミノメチル−4−(1−エチル−シクロヘキシル)−酪酸、
から選ばれる化合物又は医薬として許容されるその塩。 - 以下の:
請求項1〜7のいずれか1項に記載の化合物又は医薬として許容されるその塩の治療的有効量;及び
医薬として許容される担体、
を含む医薬組成物。 - ヒトを含む哺乳動物における障害又は症状の治療用医薬組成物であって、請求項1〜7のいずれか1項に記載の化合物又は医薬として許容されるその塩の治療的有効量を含み、ここで、当該障害又は症状は、炎症性の痛み、慢性の痛み、急性の痛み、神経障害性の痛み、睡眠障害、一過性熱感(突発的衝動)、及び不安から選ばれる、前記医薬組成物。
- 前記障害又は症状が神経障害性の痛みである、請求項9に記載の医薬組成物。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US36841302P | 2002-03-28 | 2002-03-28 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003580276A Division JP3831379B2 (ja) | 2002-03-28 | 2003-03-17 | α2δ−タンパク質へのアフィニティを有するアミノ酸 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006028189A true JP2006028189A (ja) | 2006-02-02 |
JP3857714B2 JP3857714B2 (ja) | 2006-12-13 |
Family
ID=28675482
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003580276A Expired - Fee Related JP3831379B2 (ja) | 2002-03-28 | 2003-03-17 | α2δ−タンパク質へのアフィニティを有するアミノ酸 |
JP2005218738A Expired - Fee Related JP3857714B2 (ja) | 2002-03-28 | 2005-07-28 | α2δ−タンパク質へのアフィニティを有するアミノ酸 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003580276A Expired - Fee Related JP3831379B2 (ja) | 2002-03-28 | 2003-03-17 | α2δ−タンパク質へのアフィニティを有するアミノ酸 |
Country Status (43)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103164756A (zh) * | 2011-12-12 | 2013-06-19 | 苏州艾隆科技有限公司 | 贵重药品的管理方法及其系统 |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10129693A1 (de) * | 2001-06-22 | 2003-01-02 | Jan Loock | Verfahren zur extrakorporalen qualitativen und/oder quantitativen Erfassung neurotoxischer Substanzen im Blutplasma eines Individuums |
NI200300043A (es) * | 2002-03-28 | 2003-11-05 | Warner Lambert Co | AMINOACIDOS CON AFINIDAD POR LA PROTEINA a2DELTA. |
US7419981B2 (en) | 2002-08-15 | 2008-09-02 | Pfizer Inc. | Synergistic combinations of an alpha-2-delta ligand and a cGMP phosphodieterse 5 inhibitor |
CA2451267A1 (en) | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
WO2005002585A1 (en) * | 2003-07-02 | 2005-01-13 | Warner-Lambert Company Llc | Combination of an allosteric inhibitor of matrix metalloproteinase-13 and a ligand to an alpha-2-delta receptor |
WO2005030184A2 (en) * | 2003-09-25 | 2005-04-07 | Warner-Lambert Company Llc | Therapeutic beta aminoacids |
MXPA06003395A (es) * | 2003-09-25 | 2006-06-08 | Warner Lambert Co | Aminoacidos con afinidad por la proteina a2d. |
PT1727620E (pt) * | 2004-03-12 | 2007-11-05 | Warner Lambert Co | Ligandos de biofosfina c1-simétricos e a sua utilização na síntese assimétrica da pregabalina |
BRPI0513028A (pt) * | 2004-07-09 | 2008-04-22 | Warner Lambert Co | preparação de beta-aminoácidos tendo afinidade para a proteìna alfa-2-delta |
WO2006092692A1 (en) * | 2005-03-01 | 2006-09-08 | Pfizer Limited | Use of combinations of pde7 inhibitors and alpha-2-delty ligands for the treatment of neuropathic pain |
US20080194841A1 (en) * | 2005-03-24 | 2008-08-14 | Pfizer Inc. | Preparation of Optically Pure Beta-Amino Acids Having Affinity for the Alpha-Delta Protein |
WO2007052134A1 (en) * | 2005-11-04 | 2007-05-10 | Pfizer Limited | (2s)-2-aminomethyl-5-ethyl heptanoic acid its pharmaceutical use |
EP1954260A2 (en) * | 2005-11-17 | 2008-08-13 | Pfizer Limited | Isocystene derivatives for the treatment of pain |
MX2008011396A (es) * | 2006-03-06 | 2008-09-18 | Pfizer Prod Inc | Ligandos alfa-2-delta para sueño no reconstituyente. |
AR061728A1 (es) * | 2006-06-30 | 2008-09-17 | Pfizer Prod Inc | Composicion para tratamiento usando compuestos selectivos alfa-2-delta-1 |
US20110124705A1 (en) * | 2009-11-24 | 2011-05-26 | Xenoport, Inc. | Prodrugs of alpha-2-delta ligands, pharmaceutical compositions and uses thereof |
PL2710005T3 (pl) | 2011-05-17 | 2017-07-31 | Principia Biopharma Inc. | Inhibitory kinazy tyrozynowej |
CN103717602B (zh) | 2011-05-17 | 2016-11-09 | 加利福尼亚大学董事会 | 激酶抑制剂 |
US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
RS58956B1 (sr) | 2012-09-10 | 2019-08-30 | Principia Biopharma Inc | Jedinjenja pirazolopirimidina kao inhibitori kinaze |
US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
ES2841248T3 (es) | 2014-02-21 | 2021-07-07 | Principia Biopharma Inc | Sales y forma sólida de un inhibidor de BTK |
PT3233103T (pt) | 2014-12-18 | 2021-01-18 | Principia Biopharma Inc | Tratamento de pênfigo |
MA42242A (fr) | 2015-06-24 | 2018-05-02 | Principia Biopharma Inc | Inhibiteurs de la tyrosine kinase |
KR102515813B1 (ko) | 2016-06-29 | 2023-03-30 | 프린시피아 바이오파마, 인코퍼레이티드 | 2-[3-[4-아미노-3-(2-플루오로-4-페녹시-페닐)피라졸로[3,4-d]피리미딘-1-일]피페리딘-1-카르보닐]-4-메틸-4-[4-(옥세탄-3-일)피페라진-1-일]펜트-2-엔니트릴의 변형 방출 제제 |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1377736A (fr) * | 1962-12-21 | 1964-11-06 | Hoffmann La Roche | Procédé pour la préparation d'acides amino-carboxyliques |
FR1377366A (fr) | 1963-08-19 | 1964-11-06 | Dispositif de protection de sécurité pour appareils électriques | |
KR880007441A (ko) * | 1986-12-11 | 1988-08-27 | 알렌 제이.스피겔 | 스피로-치환된 글루타르아미드 이뇨제 |
AU7168091A (en) | 1989-12-22 | 1991-07-24 | Schering Corporation | Mercaptocycloacyl aminoacid endopeptidase inhibitors |
US5614498A (en) | 1990-06-07 | 1997-03-25 | Banyu Pharmaceutical Co., Ltd. | Endothelin antagonistic substance |
US5011066A (en) * | 1990-07-27 | 1991-04-30 | Motorola, Inc. | Enhanced collapse solder interconnection |
US5239113A (en) | 1991-10-15 | 1993-08-24 | Monsanto Company | Substituted β-amino acid derivatives useful as platelet aggregation inhibitors and intermediates thereof |
EP0561758A3 (en) | 1992-03-18 | 1995-04-05 | Monsanto Co | Method of preparing optically active homo-beta-amino acids |
US5578606A (en) * | 1992-10-30 | 1996-11-26 | G. D. Searle & Co. | α- and β-amino acid hydroxyethylamino sulfonyl urea derivatives useful as retroviral protease inhibitors |
AU684878B2 (en) | 1993-11-24 | 1998-01-08 | Merck & Co., Inc. | Compounds and the use thereof to promote the release of growth hormone(s) |
CA2178829A1 (en) | 1993-12-12 | 1995-06-15 | Yigal Cohen | A novel method to protect plants from fungal infection |
US5472830A (en) | 1994-04-18 | 1995-12-05 | Ocg Microelectronic Materials, Inc. | Non-corrosion photoresist stripping composition |
DE69709742T2 (de) | 1996-07-12 | 2002-08-08 | Searle & Co | Asymmetrische synthese von chiralen beta-aminosäuren |
DE69737719D1 (de) * | 1996-10-23 | 2007-06-21 | Warner Lambert Co | Substituierte gamma-aminobuttersäurederivate als arzneimittel |
US6306909B1 (en) | 1997-03-12 | 2001-10-23 | Queen's University At Kingston | Anti-epileptogenic agents |
GB2323594A (en) | 1997-03-25 | 1998-09-30 | Victor Martin | 2-amino-alkanoic acid derivatives, 2-amino alcohols and diamines |
US6201023B1 (en) | 1997-06-10 | 2001-03-13 | Agrogene Ltd. | Methods and compositions to protect crops against plant parasitic nematodes |
US6011066A (en) | 1998-02-02 | 2000-01-04 | Veterans General Hospital-Taipei | Method for treating septic shock |
AU755273B2 (en) | 1998-03-16 | 2002-12-05 | Cytovia, Inc. | Dipeptide caspase inhibitors and the use thereof |
EP1013769A1 (en) | 1998-12-22 | 2000-06-28 | Dsm N.V. | Process for the enzymatic preparation of amino acid derivatives with enhanced optical purity |
FR2791982B1 (fr) | 1999-04-06 | 2002-12-27 | Inst Nat Sante Rech Med | Inhibiteurs de lta4 hydrolase et leurs applications therapeutiques. |
OA11962A (en) * | 1999-06-10 | 2006-04-17 | Warner Lambert Co | Mono-and disubstituted 3-propyl gamma-aminobutyricacids. |
EP1294854A2 (en) * | 2000-05-16 | 2003-03-26 | Warner-Lambert Company | Cell line for the expression of an alpha2-delta2 calcium channel subunit |
AU2001258543A1 (en) | 2000-05-17 | 2001-11-26 | Medivir Uk Limited | Branched amino acids |
NZ525143A (en) | 2000-09-14 | 2005-12-23 | Gruenenthal Chemie | Beta-thio-amino acids |
DE10048715A1 (de) | 2000-09-30 | 2004-05-19 | Grünenthal GmbH | Verwendung von Aminosäure zur Behandlung von Schmerz |
IL157845A0 (en) * | 2001-03-13 | 2004-03-28 | Univ Kingston | Anti-epileptogenic agents |
NI200300043A (es) * | 2002-03-28 | 2003-11-05 | Warner Lambert Co | AMINOACIDOS CON AFINIDAD POR LA PROTEINA a2DELTA. |
GB0219024D0 (en) * | 2002-08-15 | 2002-09-25 | Pfizer Ltd | Synergistic combinations |
CN1228312C (zh) * | 2002-12-27 | 2005-11-23 | 中国科学院化学研究所 | 以酮为原料合成β—氨基酸的方法 |
-
2003
- 2003-03-06 NI NI200300043A patent/NI200300043A/es unknown
- 2003-03-17 EP EP03706831A patent/EP1492761B1/en not_active Expired - Lifetime
- 2003-03-17 PL PL373363A patent/PL209750B1/pl not_active IP Right Cessation
- 2003-03-17 NZ NZ541320A patent/NZ541320A/en unknown
- 2003-03-17 MX MXPA04009373A patent/MXPA04009373A/es active IP Right Grant
- 2003-03-17 CN CNB038112698A patent/CN100462351C/zh not_active Expired - Fee Related
- 2003-03-17 WO PCT/IB2003/000976 patent/WO2003082807A2/en active Application Filing
- 2003-03-17 UA UAA200507455A patent/UA80018C2/uk unknown
- 2003-03-17 NZ NZ535364A patent/NZ535364A/en not_active IP Right Cessation
- 2003-03-17 ES ES03706831T patent/ES2327910T3/es not_active Expired - Lifetime
- 2003-03-17 DE DE60328469T patent/DE60328469D1/de not_active Expired - Lifetime
- 2003-03-17 EP EP05108848A patent/EP1614675A3/en not_active Withdrawn
- 2003-03-17 BR BR0308814-6A patent/BR0308814A/pt active Search and Examination
- 2003-03-17 EA EA200401127A patent/EA008709B1/ru unknown
- 2003-03-17 JP JP2003580276A patent/JP3831379B2/ja not_active Expired - Fee Related
- 2003-03-17 CN CNA2006100070283A patent/CN1817854A/zh active Pending
- 2003-03-17 SI SI200331654T patent/SI1492761T1/sl unknown
- 2003-03-17 OA OA1200400254A patent/OA12795A/en unknown
- 2003-03-17 KR KR1020057025293A patent/KR100694719B1/ko not_active IP Right Cessation
- 2003-03-17 GE GEAP20038907A patent/GEP20084298B/en unknown
- 2003-03-17 DK DK03706831T patent/DK1492761T3/da active
- 2003-03-17 UA UA20040907854A patent/UA80116C2/uk unknown
- 2003-03-17 KR KR1020047015361A patent/KR100630981B1/ko not_active IP Right Cessation
- 2003-03-17 GE GEAP8423A patent/GEP20074123B/en unknown
- 2003-03-17 AU AU2003208538A patent/AU2003208538B2/en not_active Ceased
- 2003-03-17 RS YUP-836/04A patent/RS83604A/sr unknown
- 2003-03-17 PT PT03706831T patent/PT1492761E/pt unknown
- 2003-03-17 IL IL16411003A patent/IL164110A0/xx unknown
- 2003-03-17 AP APAP/P/2004/003144A patent/AP1791A/en active
- 2003-03-17 EA EA200501497A patent/EA200501497A1/ru unknown
- 2003-03-17 CA CA2480872A patent/CA2480872C/en not_active Expired - Fee Related
- 2003-03-17 RS YUP-2005/0667A patent/RS20050667A/sr unknown
- 2003-03-24 TW TW092106516A patent/TWI225864B/zh not_active IP Right Cessation
- 2003-03-25 PE PE2003000303A patent/PE20040349A1/es not_active Application Discontinuation
- 2003-03-25 MY MYPI20031051A patent/MY131424A/en unknown
- 2003-03-26 AR ARP030101060A patent/AR039154A1/es not_active Application Discontinuation
- 2003-03-27 US US10/401,060 patent/US7064147B2/en not_active Expired - Lifetime
- 2003-03-27 UY UY27738A patent/UY27738A1/es not_active Application Discontinuation
- 2003-03-28 GT GT200300072AK patent/GT200300072AA/es unknown
- 2003-03-28 GT GT200300072A patent/GT200300072A/es unknown
- 2003-03-28 PA PA20038570001A patent/PA8570001A1/es unknown
-
2004
- 2004-09-16 IS IS7451A patent/IS7451A/is unknown
- 2004-09-17 ZA ZA2004/07536A patent/ZA200407536B/en unknown
- 2004-09-24 MA MA27874A patent/MA27188A1/fr unknown
- 2004-09-27 CU CU20040212A patent/CU23331B7/es not_active IP Right Cessation
- 2004-09-27 TN TNP2004000186A patent/TNSN04186A1/fr unknown
- 2004-09-28 HR HRP20040891 patent/HRP20040891A2/hr not_active Application Discontinuation
- 2004-09-28 CR CR7501A patent/CR7501A/es unknown
- 2004-09-28 EC EC2004005319A patent/ECSP045319A/es unknown
- 2004-10-26 NO NO20044614A patent/NO20044614L/no not_active Application Discontinuation
-
2005
- 2005-07-01 US US11/173,073 patent/US20050272783A1/en not_active Abandoned
- 2005-07-20 AR ARP050102999A patent/AR050261A2/es unknown
- 2005-07-21 IS IS7951A patent/IS7951A/is unknown
- 2005-07-21 IL IL169820A patent/IL169820A0/en unknown
- 2005-07-28 JP JP2005218738A patent/JP3857714B2/ja not_active Expired - Fee Related
- 2005-08-23 NO NO20053918A patent/NO20053918L/no not_active Application Discontinuation
- 2005-09-02 HR HR20050764A patent/HRP20050764A2/hr not_active Application Discontinuation
- 2005-09-29 HK HK05108642.0A patent/HK1076627A1/xx not_active IP Right Cessation
-
2006
- 2006-03-14 US US11/375,318 patent/US7517909B2/en not_active Expired - Fee Related
-
2009
- 2009-08-12 CY CY20091100858T patent/CY1109304T1/el unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103164756A (zh) * | 2011-12-12 | 2013-06-19 | 苏州艾隆科技有限公司 | 贵重药品的管理方法及其系统 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3857714B2 (ja) | α2δ−タンパク質へのアフィニティを有するアミノ酸 | |
JP4555263B2 (ja) | カルシウムチャンネルα2δサブユニットに親和性を有するプロリン誘導体 | |
US20060247282A1 (en) | Methods for using amino acids with affinity for the alpha2delta-protein | |
AU2005203759B2 (en) | Amino acids with affinity for the alpha-2-delta-protein | |
ZA200601389B (en) | Amino acids with affinity for the alpha2delta-protein |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20051102 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20051115 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20060214 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20060217 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060407 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060509 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060721 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20060815 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20060914 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100922 Year of fee payment: 4 |
|
LAPS | Cancellation because of no payment of annual fees |