AU2013328280B2 - Ketamine derivatives - Google Patents
Ketamine derivatives Download PDFInfo
- Publication number
- AU2013328280B2 AU2013328280B2 AU2013328280A AU2013328280A AU2013328280B2 AU 2013328280 B2 AU2013328280 B2 AU 2013328280B2 AU 2013328280 A AU2013328280 A AU 2013328280A AU 2013328280 A AU2013328280 A AU 2013328280A AU 2013328280 B2 AU2013328280 B2 AU 2013328280B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- amino
- chlorophenyl
- oxocyclohexyl
- optionally substituted
- 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.)
- Ceased
Links
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical class C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 title abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 50
- 208000002193 Pain Diseases 0.000 claims abstract description 18
- 230000036407 pain Effects 0.000 claims abstract description 18
- 230000001624 sedative effect Effects 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 130
- 239000001257 hydrogen Substances 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 150000002431 hydrogen Chemical group 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
- 239000012453 solvate Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- OSYLIDUZSLQOIW-UHFFFAOYSA-N ethyl 3-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]propanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCC(=O)OCC)CCCCC1=O OSYLIDUZSLQOIW-UHFFFAOYSA-N 0.000 claims description 5
- FZIHUEMGZWQMJF-UHFFFAOYSA-N ethyl 4-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]butanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCC(=O)OCC)CCCCC1=O FZIHUEMGZWQMJF-UHFFFAOYSA-N 0.000 claims description 5
- KFZMXHQTFSGYLL-UHFFFAOYSA-N ethyl 5-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]pentanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCCC(=O)OCC)CCCCC1=O KFZMXHQTFSGYLL-UHFFFAOYSA-N 0.000 claims description 5
- QFFBIIVCZDWTKZ-UHFFFAOYSA-N methyl 5-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]pentanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCCC(=O)OC)CCCCC1=O QFFBIIVCZDWTKZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UMTAVENMCNHZKS-UHFFFAOYSA-N propan-2-yl 4-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]butanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCC(=O)OC(C)C)CCCCC1=O UMTAVENMCNHZKS-UHFFFAOYSA-N 0.000 claims description 4
- VELFQRXGQQEDQS-UHFFFAOYSA-N propan-2-yl 5-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]pentanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCCC(=O)OC(C)C)CCCCC1=O VELFQRXGQQEDQS-UHFFFAOYSA-N 0.000 claims description 4
- BEMFAESGNZMDAI-UHFFFAOYSA-N 3-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]propyl acetate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCOC(=O)C)CCCCC1=O BEMFAESGNZMDAI-UHFFFAOYSA-N 0.000 claims description 3
- GNIZNSSNZICSGW-UHFFFAOYSA-N ethyl 3-[[1-(2-chlorophenyl)-2-oxocyclohexyl]-methylamino]propanoate Chemical compound C=1C=CC=C(Cl)C=1C1(N(C)CCC(=O)OCC)CCCCC1=O GNIZNSSNZICSGW-UHFFFAOYSA-N 0.000 claims description 3
- MLQTZSYHBXPNKI-UHFFFAOYSA-N ethyl 4-[[1-(2-chlorophenyl)-2-oxocyclohexyl]-methylamino]butanoate Chemical compound C=1C=CC=C(Cl)C=1C1(N(C)CCCC(=O)OCC)CCCCC1=O MLQTZSYHBXPNKI-UHFFFAOYSA-N 0.000 claims description 2
- OYHDMPDRGZQTIM-UHFFFAOYSA-N propan-2-yl 3-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]propanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCC(=O)OC(C)C)CCCCC1=O OYHDMPDRGZQTIM-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- GSLQTNIISBAJKM-UHFFFAOYSA-N propyl 3-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]propanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCC(=O)OCCC)CCCCC1=O GSLQTNIISBAJKM-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 22
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
- 229960003299 ketamine Drugs 0.000 description 29
- -1 diastereomeric Chemical class 0.000 description 28
- 239000000203 mixture Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 206010039897 Sedation Diseases 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 230000036280 sedation Effects 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 16
- 238000001802 infusion Methods 0.000 description 15
- BEQZHFIKTBVCAU-UHFFFAOYSA-N 2-amino-2-(2-chlorophenyl)-1-cyclohexanone Chemical compound C=1C=CC=C(Cl)C=1C1(N)CCCCC1=O BEQZHFIKTBVCAU-UHFFFAOYSA-N 0.000 description 14
- 206010002091 Anaesthesia Diseases 0.000 description 14
- 230000003444 anaesthetic effect Effects 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 230000037005 anaesthesia Effects 0.000 description 13
- 238000001949 anaesthesia Methods 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000001939 inductive effect Effects 0.000 description 12
- 238000011084 recovery Methods 0.000 description 12
- 230000028527 righting reflex Effects 0.000 description 12
- 238000001990 intravenous administration Methods 0.000 description 11
- 230000003389 potentiating effect Effects 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 208000012802 recumbency Diseases 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 230000036592 analgesia Effects 0.000 description 5
- 230000011514 reflex Effects 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- BEQZHFIKTBVCAU-LBPRGKRZSA-N (2s)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one Chemical compound C=1C=CC=C(Cl)C=1[C@@]1(N)CCCCC1=O BEQZHFIKTBVCAU-LBPRGKRZSA-N 0.000 description 4
- FGTRLPFQPZJCQO-UHFFFAOYSA-N 2-iminocyclopentan-1-ol Chemical compound OC1CCCC1=N FGTRLPFQPZJCQO-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical group [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 4
- 230000000147 hypnotic effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000006485 reductive methylation reaction Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
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- 238000001356 surgical procedure Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
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- DDVNLGGCSRULIL-UHFFFAOYSA-N (1-bromocyclopentyl)-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C1(Br)CCCC1 DDVNLGGCSRULIL-UHFFFAOYSA-N 0.000 description 3
- QIJMMRNZBJHXRI-UHFFFAOYSA-N (2-chlorophenyl)-cyclopentylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1CCCC1 QIJMMRNZBJHXRI-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- WNXNUPJZWYOKMW-UHFFFAOYSA-M 5-bromopentanoate Chemical compound [O-]C(=O)CCCCBr WNXNUPJZWYOKMW-UHFFFAOYSA-M 0.000 description 3
- 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 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- 229940124326 anaesthetic agent Drugs 0.000 description 3
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- AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 3
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- FRANGXMVILSKAR-UHFFFAOYSA-N methyl 5-[[1-(2-chlorophenyl)-2-oxocyclohexyl]-methylamino]pentanoate Chemical compound C=1C=CC=C(Cl)C=1C1(N(C)CCCCC(=O)OC)CCCCC1=O FRANGXMVILSKAR-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- KQNJUTDIDREYGN-UHFFFAOYSA-N propan-2-yl 3-bromopropanoate Chemical compound CC(C)OC(=O)CCBr KQNJUTDIDREYGN-UHFFFAOYSA-N 0.000 description 3
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- DXFHVUUGWSXHQY-UHFFFAOYSA-N propyl 3-bromopropanoate Chemical compound CCCOC(=O)CCBr DXFHVUUGWSXHQY-UHFFFAOYSA-N 0.000 description 1
- VBIALSIHBKQBCK-UHFFFAOYSA-N propyl 4-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]butanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCC(=O)OCCC)CCCCC1=O VBIALSIHBKQBCK-UHFFFAOYSA-N 0.000 description 1
- GKTWIJVDNVTXCV-UHFFFAOYSA-N propyl 5-bromopentanoate Chemical compound CCCOC(=O)CCCCBr GKTWIJVDNVTXCV-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
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 230000000638 stimulation 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000001755 vocal effect Effects 0.000 description 1
- 150000003751 zinc Chemical class 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
- C07C229/10—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 acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—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 acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
-
- 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
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ60288512 | 2012-10-08 | ||
| NZ602885 | 2012-10-08 | ||
| NZ611202 | 2013-05-28 | ||
| NZ61120213 | 2013-05-28 | ||
| PCT/IB2013/059191 WO2014057414A1 (en) | 2012-10-08 | 2013-10-08 | Ketamine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2013328280A1 AU2013328280A1 (en) | 2015-05-14 |
| AU2013328280B2 true AU2013328280B2 (en) | 2017-12-21 |
Family
ID=50476991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013328280A Ceased AU2013328280B2 (en) | 2012-10-08 | 2013-10-08 | Ketamine derivatives |
Country Status (13)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HK1212673A1 (zh) * | 2012-10-08 | 2016-06-17 | 奥克兰服务有限公司 | 氯胺酮衍生物 |
| US20160332962A1 (en) * | 2015-05-13 | 2016-11-17 | Janssen Pharmaceutica Nv | (s)-csa salt of s-ketamine, (r)-csa salt of s-ketamine and processes for the preparation of s-ketamine |
| JP6845162B2 (ja) | 2015-06-27 | 2021-03-17 | シェノックス・ファーマシューティカルズ・エルエルシー | ケタミン経皮送達システム |
| US11827606B2 (en) | 2015-11-18 | 2023-11-28 | Spirify Pharma Inc. | Phenyl cyclohexanone derivatives and methods of making and using them |
| US11111210B2 (en) | 2015-11-18 | 2021-09-07 | Spirify Pharma Inc. | Phenyl cyclohexanone derivatives and methods of making and using them |
| CN115108927A (zh) * | 2016-03-25 | 2022-09-27 | 美国政府健康及人类服务部 | (2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 |
| KR20230110828A (ko) | 2018-01-10 | 2023-07-25 | 엑스더블유파마 리미티드 | 케타민의 전구약물, 및 이의 조성물 및 용도 |
| WO2019186357A1 (en) * | 2018-03-26 | 2019-10-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| EP3802480B1 (en) * | 2018-06-04 | 2023-08-02 | The United States of America, as represented by the Secretary, Department of Health and Human Services | Process for synthesis and purification of (2r,6r)-hydroxynorketamine |
| CN112125816A (zh) * | 2020-03-17 | 2020-12-25 | 国药集团工业有限公司 | 一种氯胺酮、其衍生物或其盐的消旋化方法 |
| DE102021105268A1 (de) * | 2021-03-04 | 2022-09-08 | Lts Lohmann Therapie-Systeme Ag. | Oraler Dünnfilm |
| TWI844074B (zh) | 2021-08-13 | 2024-06-01 | 凱瑞康寧生技股份有限公司 | 氯胺酮衍生物之醫藥組成物及口服劑型 |
| CN115677444A (zh) * | 2022-10-26 | 2023-02-03 | 公安部第三研究所 | 同位素毒品代谢物标记化合物及其制备方法、用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004045601A1 (en) * | 2002-11-18 | 2004-06-03 | Yaupon Therapeutics, Inc. | Analgesic uses of norketamine and ketamine/norketamine prodrugs |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254124A (en) * | 1962-06-29 | 1966-05-31 | Parke Davis & Co | Aminoketones and methods for their production |
| GB1134146A (en) * | 1967-09-15 | 1968-11-20 | Parke Davis & Co | New organic amines and methods for their production |
| US5019583A (en) | 1989-02-15 | 1991-05-28 | Glaxo Inc. | N-phenyl-N-(4-piperidinyl)amides useful as analgesics |
| US5466700A (en) | 1993-08-30 | 1995-11-14 | Glaxo Wellcome Inc. | Anesthetic use of N-phenyl-N-(4-piperidinyl)amides |
| US5866591A (en) | 1996-09-11 | 1999-02-02 | Glaxo Wellcome Inc. | Stable formulations of remifentanil |
| CA2397831A1 (en) * | 2000-01-28 | 2001-08-02 | Rohm And Haas Company | Enhanced propertied pharmaceuticals |
| US20040248963A1 (en) | 2001-11-23 | 2004-12-09 | Bueno Melendo Ana Belen | Prodrugs of excitatory amino acids |
| EP1333023B1 (en) | 2002-01-31 | 2010-12-22 | Randox Laboratories Ltd. | Immunogens, antibodies and conjugates to ketamine and its metabolites |
| EP1928405B1 (en) * | 2005-09-28 | 2014-09-24 | Auris Medical AG | Pharmaceutical compositions for the treatment of inner ear disorders |
| EP2139848A1 (en) | 2007-04-26 | 2010-01-06 | Auspex Pharmaceuticals, Inc. | Deuterium labelled ketamine |
| ES2886361T3 (es) * | 2011-10-14 | 2021-12-17 | The Us Secretary Department Of Health & Human Services | Uso de (2R,6R)-hidroxinorketamina y otros metabolitos hidroxilados estereoisómeros de (R,S)-ketamina en el tratamiento de depresión y dolor neuropático |
| HK1212673A1 (zh) * | 2012-10-08 | 2016-06-17 | 奥克兰服务有限公司 | 氯胺酮衍生物 |
-
2013
- 2013-10-08 HK HK16100661.0A patent/HK1212673A1/zh unknown
- 2013-10-08 KR KR1020157012009A patent/KR20150065873A/ko not_active Ceased
- 2013-10-08 WO PCT/IB2013/059191 patent/WO2014057414A1/en not_active Ceased
- 2013-10-08 EP EP13846133.0A patent/EP2903963A4/en not_active Withdrawn
- 2013-10-08 MX MX2015004362A patent/MX2015004362A/es unknown
- 2013-10-08 CN CN201380061537.2A patent/CN104837810B/zh not_active Expired - Fee Related
- 2013-10-08 AU AU2013328280A patent/AU2013328280B2/en not_active Ceased
- 2013-10-08 CA CA2922340A patent/CA2922340A1/en not_active Abandoned
- 2013-10-08 EA EA201590697A patent/EA201590697A1/ru unknown
- 2013-10-08 JP JP2015535162A patent/JP6309957B2/ja not_active Expired - Fee Related
- 2013-10-08 IN IN3854DEN2015 patent/IN2015DN03854A/en unknown
- 2013-10-08 US US14/433,957 patent/US20150259277A1/en not_active Abandoned
- 2013-10-08 BR BR112015007647A patent/BR112015007647A2/pt not_active Application Discontinuation
-
2017
- 2017-03-20 US US15/463,532 patent/US10239825B2/en not_active Expired - Fee Related
-
2018
- 2018-03-14 JP JP2018046540A patent/JP2018127466A/ja active Pending
-
2019
- 2019-02-06 US US16/269,015 patent/US20190169113A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004045601A1 (en) * | 2002-11-18 | 2004-06-03 | Yaupon Therapeutics, Inc. | Analgesic uses of norketamine and ketamine/norketamine prodrugs |
Also Published As
| Publication number | Publication date |
|---|---|
| IN2015DN03854A (cg-RX-API-DMAC7.html) | 2015-10-02 |
| JP2018127466A (ja) | 2018-08-16 |
| US10239825B2 (en) | 2019-03-26 |
| EP2903963A1 (en) | 2015-08-12 |
| CA2922340A1 (en) | 2014-04-17 |
| US20170190653A1 (en) | 2017-07-06 |
| CN104837810B (zh) | 2019-08-06 |
| MX2015004362A (es) | 2015-12-08 |
| WO2014057414A1 (en) | 2014-04-17 |
| US20190169113A1 (en) | 2019-06-06 |
| WO2014057414A9 (en) | 2014-12-18 |
| EA201590697A1 (ru) | 2015-09-30 |
| CN104837810A (zh) | 2015-08-12 |
| US20150259277A1 (en) | 2015-09-17 |
| EP2903963A4 (en) | 2016-05-25 |
| JP2015535847A (ja) | 2015-12-17 |
| AU2013328280A1 (en) | 2015-05-14 |
| KR20150065873A (ko) | 2015-06-15 |
| JP6309957B2 (ja) | 2018-04-11 |
| HK1212673A1 (zh) | 2016-06-17 |
| BR112015007647A2 (pt) | 2017-07-04 |
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Legal Events
| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |