DE1293761B - Verfahren zur Herstellung von Aminoketonen - Google Patents
Verfahren zur Herstellung von AminoketonenInfo
- Publication number
- DE1293761B DE1293761B DEST20790A DEST020790A DE1293761B DE 1293761 B DE1293761 B DE 1293761B DE ST20790 A DEST20790 A DE ST20790A DE ST020790 A DEST020790 A DE ST020790A DE 1293761 B DE1293761 B DE 1293761B
- Authority
- DE
- Germany
- Prior art keywords
- ketone
- yield
- melting point
- methylamino
- ether
- 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.)
- Pending
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 54
- -1 methyl-methoxy Chemical group 0.000 claims description 36
- 239000007858 starting material Substances 0.000 claims description 27
- 230000008707 rearrangement Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WMEOMAYOFHGZIF-UHFFFAOYSA-N 1-hydroxy-1,1-diphenylpropan-2-one Chemical compound C=1C=CC=CC=1C(O)(C(=O)C)C1=CC=CC=C1 WMEOMAYOFHGZIF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims 1
- PXKUZMFBETZOJR-UHFFFAOYSA-N C(C)NC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)NCC Chemical compound C(C)NC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)NCC PXKUZMFBETZOJR-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- 230000008018 melting Effects 0.000 description 52
- 238000002844 melting Methods 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- 238000009835 boiling Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 14
- 239000004593 Epoxy Substances 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 238000010992 reflux Methods 0.000 description 6
- VWEZFLADPWFUNE-UHFFFAOYSA-N 1-[2-chloro-3-[C-[2-chloro-3-(1-hydroxycyclopentyl)phenyl]-N-methylcarbonimidoyl]phenyl]cyclopentan-1-ol Chemical compound CN=C(C1=C(C(=CC=C1)C1(CCCC1)O)Cl)C1=C(C(=CC=C1)C1(CCCC1)O)Cl VWEZFLADPWFUNE-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- ASZRBXHYVMVSAX-UHFFFAOYSA-N [1-(ethylamino)cyclopentyl]-(4-methylphenyl)methanone Chemical group C=1C=C(C)C=CC=1C(=O)C1(NCC)CCCC1 ASZRBXHYVMVSAX-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- QKXPNIMOBXBHGW-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(Cl)C=CC=1C1(NC)CCCCC1=O QKXPNIMOBXBHGW-UHFFFAOYSA-N 0.000 description 3
- ZAGBSZSITDFFAF-UHFFFAOYSA-N 2-(methylamino)-2-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(NC)CCCCC1=O ZAGBSZSITDFFAF-UHFFFAOYSA-N 0.000 description 3
- QCXKLSJCXITLHD-UHFFFAOYSA-N 2-methyl-2-(methylamino)-1-phenylbutan-1-one Chemical compound CCC(C)(NC)C(=O)C1=CC=CC=C1 QCXKLSJCXITLHD-UHFFFAOYSA-N 0.000 description 3
- JLVGGPQTLAPRPH-UHFFFAOYSA-N 2-methyl-2-(methylamino)-1-phenylpropan-1-one Chemical compound CNC(C)(C)C(=O)C1=CC=CC=C1 JLVGGPQTLAPRPH-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- YSQNWYVHBOXDIY-UHFFFAOYSA-N 4-(methylamino)-4-phenylhexan-3-one Chemical compound CCC(=O)C(CC)(NC)C1=CC=CC=C1 YSQNWYVHBOXDIY-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- ZOAQLIJZJVAOLU-UHFFFAOYSA-N bis[1-(4-methoxyphenyl)cyclopentyl]methanone Chemical compound COC1=CC=C(C=C1)C1(CCCC1)C(=O)C1(CCCC1)C1=CC=C(C=C1)OC ZOAQLIJZJVAOLU-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GTQWGXVWCDMYRI-UHFFFAOYSA-N (1-bromocyclopentyl)-(4-chlorophenyl)methanone Chemical compound Clc1ccc(cc1)C(=O)C1(Br)CCCC1 GTQWGXVWCDMYRI-UHFFFAOYSA-N 0.000 description 2
- OAUNRWNNNLUFEF-UHFFFAOYSA-N (4-chlorophenyl)-cyclopentylmethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCCC1 OAUNRWNNNLUFEF-UHFFFAOYSA-N 0.000 description 2
- ZUODBPPZEFMRJW-UHFFFAOYSA-N (4-methoxyphenyl)-[1-(methylamino)cyclopentyl]methanone Chemical compound C=1C=C(OC)C=CC=1C(=O)C1(NC)CCCC1 ZUODBPPZEFMRJW-UHFFFAOYSA-N 0.000 description 2
- GEHJFMOOKBKKLG-UHFFFAOYSA-N 2-(butylamino)-2-phenylcyclohexan-1-one Chemical compound C(CCC)NC1(C(CCCC1)=O)C1=CC=CC=C1 GEHJFMOOKBKKLG-UHFFFAOYSA-N 0.000 description 2
- DFZAIVLIQFZJJL-UHFFFAOYSA-N 2-(methylamino)-2-(2-methylphenyl)cyclohexan-1-one Chemical compound C=1C=CC=C(C)C=1C1(NC)CCCCC1=O DFZAIVLIQFZJJL-UHFFFAOYSA-N 0.000 description 2
- UKSNXZFQBYOUHW-UHFFFAOYSA-N 2-(methylamino)-2-(3-phenylmethoxyphenyl)cyclohexan-1-one Chemical compound CNC1(C(CCCC1)=O)C1=CC(=CC=C1)OCC1=CC=CC=C1 UKSNXZFQBYOUHW-UHFFFAOYSA-N 0.000 description 2
- KJMDOBYGKOIRQI-UHFFFAOYSA-N 2-(methylamino)-2-phenylcyclohexan-1-one;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(NC)CCCCC1=O KJMDOBYGKOIRQI-UHFFFAOYSA-N 0.000 description 2
- SPUSRSAJDLMFHW-UHFFFAOYSA-N 2-ethyl-2-(methylamino)-1-phenylbutan-1-one Chemical compound CCC(CC)(NC)C(=O)C1=CC=CC=C1 SPUSRSAJDLMFHW-UHFFFAOYSA-N 0.000 description 2
- RKPGYMUBNMEVJS-UHFFFAOYSA-N 3-(methylamino)-3-phenylbutan-2-one Chemical compound CNC(C)(C(C)=O)C1=CC=CC=C1 RKPGYMUBNMEVJS-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- GVPJTCQZPLYXKO-UHFFFAOYSA-N C=1C=CC=C(C2(O)CCCC2)C=1C(=NC)C1=CC=CC=C1C1(O)CCCC1 Chemical compound C=1C=CC=C(C2(O)CCCC2)C=1C(=NC)C1=CC=CC=C1C1(O)CCCC1 GVPJTCQZPLYXKO-UHFFFAOYSA-N 0.000 description 2
- ZYVJCJGXGDHFEI-UHFFFAOYSA-N CNC1(C(CCCC1)=O)C1=C(C=CC=C1)OCC1=CC=CC=C1 Chemical compound CNC1(C(CCCC1)=O)C1=C(C=CC=C1)OCC1=CC=CC=C1 ZYVJCJGXGDHFEI-UHFFFAOYSA-N 0.000 description 2
- ODXHNAGNKODNQS-UHFFFAOYSA-N COC1(OC12CCCC2)C2=CC=CC=C2 Chemical compound COC1(OC12CCCC2)C2=CC=CC=C2 ODXHNAGNKODNQS-UHFFFAOYSA-N 0.000 description 2
- QBDICYPBQJSNFC-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(=O)C1(CCCC1)NC Chemical compound ClC1=CC=C(C=C1)C(=O)C1(CCCC1)NC QBDICYPBQJSNFC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- RFVHVYKVRGKLNK-UHFFFAOYSA-N bis(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1 RFVHVYKVRGKLNK-UHFFFAOYSA-N 0.000 description 2
- ZWPWLKXZYNXATK-UHFFFAOYSA-N bis(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(C)C=C1 ZWPWLKXZYNXATK-UHFFFAOYSA-N 0.000 description 2
- XSCFWLRTORBXPQ-UHFFFAOYSA-N bis[1-(2-methylphenyl)cyclopentyl]methanone Chemical compound CC1=C(C=CC=C1)C1(CCCC1)C(=O)C1(CCCC1)C1=C(C=CC=C1)C XSCFWLRTORBXPQ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000006049 ring expansion reaction Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZZSWLRQESREDJP-UHFFFAOYSA-N (1-bromocyclopentyl)-(2-methylphenyl)methanone Chemical compound BrC1(CCCC1)C(=O)C1=C(C=CC=C1)C ZZSWLRQESREDJP-UHFFFAOYSA-N 0.000 description 1
- RBFOOUMOTKQRHC-UHFFFAOYSA-N (1-bromocyclopentyl)-(3-methoxyphenyl)methanone Chemical compound COC=1C=C(C=CC=1)C(=O)C1(CCCC1)Br RBFOOUMOTKQRHC-UHFFFAOYSA-N 0.000 description 1
- LZRCVDRYTAYYPI-UHFFFAOYSA-N (1-hydroxycyclopentyl)-phenylmethanone Chemical group C=1C=CC=CC=1C(=O)C1(O)CCCC1 LZRCVDRYTAYYPI-UHFFFAOYSA-N 0.000 description 1
- QIJMMRNZBJHXRI-UHFFFAOYSA-N (2-chlorophenyl)-cyclopentylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1CCCC1 QIJMMRNZBJHXRI-UHFFFAOYSA-N 0.000 description 1
- XOIRTJDXSCKPCE-UHFFFAOYSA-N (3-chlorophenyl)-cyclopentylmethanone Chemical compound ClC1=CC=CC(C(=O)C2CCCC2)=C1 XOIRTJDXSCKPCE-UHFFFAOYSA-N 0.000 description 1
- MMAXUXPERMUHSM-UHFFFAOYSA-N 1-(2-bromocyclopentyl)ethanone Chemical compound CC(=O)C1CCCC1Br MMAXUXPERMUHSM-UHFFFAOYSA-N 0.000 description 1
- CRJUEPCJZRBENT-UHFFFAOYSA-N 1-[3-[C-[3-(1-hydroxycyclopentyl)-2-methoxyphenyl]-N-methylcarbonimidoyl]-2-methoxyphenyl]cyclopentan-1-ol Chemical compound CN=C(C1=C(C(=CC=C1)C1(CCCC1)O)OC)C1=C(C(=CC=C1)C1(CCCC1)O)OC CRJUEPCJZRBENT-UHFFFAOYSA-N 0.000 description 1
- RISAKTCNHUTOLX-UHFFFAOYSA-N 1-[5-chloro-2-[C-[4-chloro-2-(1-hydroxycyclopentyl)phenyl]-N-methylcarbonimidoyl]phenyl]cyclopentan-1-ol Chemical compound CN=C(C1=C(C=C(C=C1)Cl)C1(CCCC1)O)C1=C(C=C(C=C1)Cl)C1(CCCC1)O RISAKTCNHUTOLX-UHFFFAOYSA-N 0.000 description 1
- FJGPXUPMNZOTLX-UHFFFAOYSA-N 1-[c-(2-chlorophenyl)-n-methylcarbonimidoyl]cyclopentan-1-ol Chemical compound C1CCCC1(O)C(=NC)C1=CC=CC=C1Cl FJGPXUPMNZOTLX-UHFFFAOYSA-N 0.000 description 1
- AMHOPTNGSNYSBL-UHFFFAOYSA-N 1-cyclohexylpropan-1-one Chemical compound CCC(=O)C1CCCCC1 AMHOPTNGSNYSBL-UHFFFAOYSA-N 0.000 description 1
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- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- RSUUMMQKSPQBNK-UHFFFAOYSA-N 2,2-diethyl-3-methoxy-3-phenyloxirane Chemical compound CCC1(CC)OC1(OC)C1=CC=CC=C1 RSUUMMQKSPQBNK-UHFFFAOYSA-N 0.000 description 1
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- AGQDQJBGMPVLKJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-2-(methylamino)cyclohexan-1-one hydrochloride Chemical compound Cl.CNC1(C(CCCC1)=O)C1=CC=C(C=C1)OC AGQDQJBGMPVLKJ-UHFFFAOYSA-N 0.000 description 1
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- IDLSBAANXISGEI-UHFFFAOYSA-N 2-(ethylamino)-2-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(NCC)CCCCC1=O IDLSBAANXISGEI-UHFFFAOYSA-N 0.000 description 1
- VNDADFFXYWFPBE-UHFFFAOYSA-N 2-(methylamino)-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(C)(NC)C(=O)C1=CC=CC=C1 VNDADFFXYWFPBE-UHFFFAOYSA-N 0.000 description 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 1
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- XLTHKFYJDGVMQG-UHFFFAOYSA-N 2-ethyl-3-methoxy-2-methyl-3-phenyloxirane Chemical compound CCC1(C)OC1(OC)C1=CC=CC=C1 XLTHKFYJDGVMQG-UHFFFAOYSA-N 0.000 description 1
- HDUKUJBILHMVSV-UHFFFAOYSA-N 2-methoxy-2-(4-methylphenyl)-1-oxaspiro[2.4]heptane Chemical compound COC1(OC11CCCC1)C1=CC=C(C=C1)C HDUKUJBILHMVSV-UHFFFAOYSA-N 0.000 description 1
- VRWKKNHCINTJMN-UHFFFAOYSA-N 2-methoxy-3,3-dimethyl-2-phenyloxirane Chemical compound C=1C=CC=CC=1C1(OC)OC1(C)C VRWKKNHCINTJMN-UHFFFAOYSA-N 0.000 description 1
- GACARISANCFUEB-UHFFFAOYSA-N 2-methyl-2-(methylamino)cyclohexan-1-one Chemical compound CNC1(C)CCCCC1=O GACARISANCFUEB-UHFFFAOYSA-N 0.000 description 1
- GQQDYXPOSOKFHG-UHFFFAOYSA-N 2-methyl-2-(methylamino)cyclohexan-1-one;hydrochloride Chemical compound Cl.CNC1(C)CCCCC1=O GQQDYXPOSOKFHG-UHFFFAOYSA-N 0.000 description 1
- KAYAIBFWOUTDTB-UHFFFAOYSA-N 3-(methylamino)-3-phenylbutan-2-one;hydrochloride Chemical compound Cl.CNC(C)(C(C)=O)C1=CC=CC=C1 KAYAIBFWOUTDTB-UHFFFAOYSA-N 0.000 description 1
- IBWFPYRVHYLXEU-UHFFFAOYSA-N 3-hydroxy-3-phenylbutan-2-one Chemical compound CC(=O)C(C)(O)C1=CC=CC=C1 IBWFPYRVHYLXEU-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- PYGLQHQDAANLKA-UHFFFAOYSA-N 4-(methylamino)-4-phenylhexan-3-one;hydrochloride Chemical compound Cl.CCC(=O)C(CC)(NC)C1=CC=CC=C1 PYGLQHQDAANLKA-UHFFFAOYSA-N 0.000 description 1
- MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
- 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 compound 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 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- RLJVSZAGIWSNRH-UHFFFAOYSA-N BrC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)Br Chemical compound BrC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)Br RLJVSZAGIWSNRH-UHFFFAOYSA-N 0.000 description 1
- IDFPTMMFVSRILW-UHFFFAOYSA-N C(C)NC1(C(CCCC1)=O)C1=CC=C(C=C1)C Chemical compound C(C)NC1(C(CCCC1)=O)C1=CC=C(C=C1)C IDFPTMMFVSRILW-UHFFFAOYSA-N 0.000 description 1
- LDJQRCYADQPDBU-UHFFFAOYSA-N C(CC)NC1(C(CCCC1)=O)C1=CC=C(C=C1)C Chemical compound C(CC)NC1(C(CCCC1)=O)C1=CC=C(C=C1)C LDJQRCYADQPDBU-UHFFFAOYSA-N 0.000 description 1
- RGILONRIBHNTPS-UHFFFAOYSA-N CC=1C=C(C=CC1)C(=O)C1(CCCC1)NC(C)C Chemical compound CC=1C=C(C=CC1)C(=O)C1(CCCC1)NC(C)C RGILONRIBHNTPS-UHFFFAOYSA-N 0.000 description 1
- PPMAGUUIBGPLGC-UHFFFAOYSA-N CCCNC1(CCCC1)C(C1=CC=C(C)C=C1)=O Chemical compound CCCNC1(CCCC1)C(C1=CC=C(C)C=C1)=O PPMAGUUIBGPLGC-UHFFFAOYSA-N 0.000 description 1
- ZUMPQSPGNZMZMQ-UHFFFAOYSA-N CN=C(C1(CCCC1)O)C1=CC(=CC=C1)OC Chemical compound CN=C(C1(CCCC1)O)C1=CC(=CC=C1)OC ZUMPQSPGNZMZMQ-UHFFFAOYSA-N 0.000 description 1
- DCVDZLKRLGBEOJ-UHFFFAOYSA-N CN=C(C1=C(C(=CC=C1)C1(CCCC1)O)C)C1=C(C(=CC=C1)C1(CCCC1)O)C Chemical compound CN=C(C1=C(C(=CC=C1)C1(CCCC1)O)C)C1=C(C(=CC=C1)C1(CCCC1)O)C DCVDZLKRLGBEOJ-UHFFFAOYSA-N 0.000 description 1
- SQNZRDGSSDMTNF-UHFFFAOYSA-N CN=C(C1=C(C(=CC=C1)Cl)C1C(CCC1)O)C1=C(C(=CC=C1)Cl)C1C(CCC1)O Chemical compound CN=C(C1=C(C(=CC=C1)Cl)C1C(CCC1)O)C1=C(C(=CC=C1)Cl)C1C(CCC1)O SQNZRDGSSDMTNF-UHFFFAOYSA-N 0.000 description 1
- YJKKANYHSDSAAO-UHFFFAOYSA-N CN=C(C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC Chemical compound CN=C(C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC YJKKANYHSDSAAO-UHFFFAOYSA-N 0.000 description 1
- JWIOPACGISSPDY-UHFFFAOYSA-N CNC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)NC Chemical compound CNC1(CCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCC1)NC JWIOPACGISSPDY-UHFFFAOYSA-N 0.000 description 1
- BLGXOZLPVNNOHH-UHFFFAOYSA-N CNC1(CCCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCCC1)NC Chemical compound CNC1(CCCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCCC1)NC BLGXOZLPVNNOHH-UHFFFAOYSA-N 0.000 description 1
- YGWJITAYEXQUIX-UHFFFAOYSA-N COC1=C(C=CC=C1)C1(CCCC1)C(=O)C1(CCCC1)C1=C(C=CC=C1)OC Chemical compound COC1=C(C=CC=C1)C1(CCCC1)C(=O)C1(CCCC1)C1=C(C=CC=C1)OC YGWJITAYEXQUIX-UHFFFAOYSA-N 0.000 description 1
- HEYBIWKOXVDZNK-UHFFFAOYSA-N COc1ccc(cc1)C(=O)C1(Br)CCCC1 Chemical compound COc1ccc(cc1)C(=O)C1(Br)CCCC1 HEYBIWKOXVDZNK-UHFFFAOYSA-N 0.000 description 1
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZGQWDAOLJNAADS-UHFFFAOYSA-N Methoxmetamine Chemical compound CNC1(C(CCCC1)=O)C1=CC(=CC=C1)OC ZGQWDAOLJNAADS-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KKHRPQNLRZGTFD-UHFFFAOYSA-N [1-(methylamino)cyclopentyl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(NC)CCCC1 KKHRPQNLRZGTFD-UHFFFAOYSA-N 0.000 description 1
- KTDJZBFLBCWTLC-UHFFFAOYSA-N acetic acid 2-(methylamino)-2-phenylcyclohexan-1-one Chemical compound C(C)(=O)O.CNC1(C(CCCC1)=O)C1=CC=CC=C1 KTDJZBFLBCWTLC-UHFFFAOYSA-N 0.000 description 1
- IZQZNLBFNMTRMF-UHFFFAOYSA-N acetic acid;phosphoric acid Chemical compound CC(O)=O.OP(O)(O)=O IZQZNLBFNMTRMF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- GSNBCDKAHGNAIE-UHFFFAOYSA-N bis(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1OC GSNBCDKAHGNAIE-UHFFFAOYSA-N 0.000 description 1
- QPRFAFKPBOLMDI-UHFFFAOYSA-N bis(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1C QPRFAFKPBOLMDI-UHFFFAOYSA-N 0.000 description 1
- CGXDIDXEMHMPIX-UHFFFAOYSA-N bis(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C=2C=C(C)C=CC=2)=C1 CGXDIDXEMHMPIX-UHFFFAOYSA-N 0.000 description 1
- ULFXZLBNZZIHJH-UHFFFAOYSA-N bis[1-(3-methoxyphenyl)cyclopentyl]methanone Chemical compound COC=1C=C(C=CC1)C1(CCCC1)C(=O)C1(CCCC1)C1=CC(=CC=C1)OC ULFXZLBNZZIHJH-UHFFFAOYSA-N 0.000 description 1
- YKQXRYZQTQDPNY-UHFFFAOYSA-N bis[1-(3-phenylmethoxyphenyl)cyclopentyl]methanone Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC1)C1(CCCC1)C(=O)C1(CCCC1)C1=CC(=CC=C1)OCC1=CC=CC=C1 YKQXRYZQTQDPNY-UHFFFAOYSA-N 0.000 description 1
- FLMZBCWNWQCQDL-UHFFFAOYSA-N bis[2-[1-(ethylamino)cyclopentyl]-4-methylphenyl]methanone Chemical compound C(C)NC1(CCCC1)C1=C(C=CC(=C1)C)C(=O)C1=C(C=C(C=C1)C)C1(CCCC1)NCC FLMZBCWNWQCQDL-UHFFFAOYSA-N 0.000 description 1
- GRBWBBBWQYSRBG-UHFFFAOYSA-N bis[3-(1-bromocyclopentyl)-2-chlorophenyl]methanone Chemical compound ClC1=C(C(=O)C=2C(=C(C=CC=2)C2(Br)CCCC2)Cl)C=CC=C1C1(Br)CCCC1 GRBWBBBWQYSRBG-UHFFFAOYSA-N 0.000 description 1
- PDZWNMQZHHUYFI-UHFFFAOYSA-N bis[3-methyl-2-[1-(propan-2-ylamino)cyclopentyl]phenyl]methanone Chemical compound C(C)(C)NC1(CCCC1)C1=C(C=CC=C1C)C(=O)C1=C(C(=CC=C1)C)C1(CCCC1)NC(C)C PDZWNMQZHHUYFI-UHFFFAOYSA-N 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- PUAQLLVFLMYYJJ-ZETCQYMHSA-N cathinone Chemical compound C[C@H](N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-ZETCQYMHSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VYDIMQRLNMMJBW-UHFFFAOYSA-N cyclopentyl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CCCC1 VYDIMQRLNMMJBW-UHFFFAOYSA-N 0.000 description 1
- ATPGKQPKLIKHTF-UHFFFAOYSA-N cyclopentyl-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1CCCC1 ATPGKQPKLIKHTF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011257 definitive treatment Methods 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ISWNAMNOYHCTSB-UHFFFAOYSA-N methanamine;hydrobromide Chemical compound [Br-].[NH3+]C ISWNAMNOYHCTSB-UHFFFAOYSA-N 0.000 description 1
- OYAUVHORXFUVAJ-UHFFFAOYSA-N methoxyketamine Chemical compound C=1C=CC=C(OC)C=1C1(NC)CCCCC1=O OYAUVHORXFUVAJ-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/13—Amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US206188A US3254124A (en) | 1962-06-29 | 1962-06-29 | Aminoketones and methods for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1293761B true DE1293761B (de) | 1969-04-30 |
Family
ID=22765332
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST20790A Pending DE1293761B (de) | 1962-06-29 | 1963-06-28 | Verfahren zur Herstellung von Aminoketonen |
| DE19631793315 Granted DE1793315B1 (de) | 1962-06-29 | 1963-06-28 | 2-Methylamino-2-(o-chlorphenyl)-cyclohexanon und seine pharmakologisch vertraeglichen Saeureadditionsverbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631793315 Granted DE1793315B1 (de) | 1962-06-29 | 1963-06-28 | 2-Methylamino-2-(o-chlorphenyl)-cyclohexanon und seine pharmakologisch vertraeglichen Saeureadditionsverbindungen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3254124A (cg-RX-API-DMAC7.html) |
| BR (1) | BR6350196D0 (cg-RX-API-DMAC7.html) |
| DE (2) | DE1293761B (cg-RX-API-DMAC7.html) |
| FR (1) | FR2973M (cg-RX-API-DMAC7.html) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3394182A (en) * | 1962-06-29 | 1968-07-23 | Parke Davis & Co | Alpha-hydroxyimines and methods for their production |
| DE1242241B (de) * | 1964-04-08 | 1967-06-15 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von substituierten Phenyl-alpha-aminoketonen und deren Saeureadditionssalzen bzw. deren optischen Antipoden |
| US3522273A (en) * | 1965-03-19 | 1970-07-28 | Parke Davis & Co | 2-(ethylamino)-2-(2-thienyl)cyclohexanone and acid addition salts |
| US3361817A (en) * | 1965-07-30 | 1968-01-02 | Parke Davis & Co | 2-(alkoxyalkyl)amino-2-phenyl-cyclohexanones and salts thereof |
| US3542869A (en) * | 1967-10-25 | 1970-11-24 | Bristol Myers Co | 1-amino-1-(o-chlorophenyl)-2-butanone and the acid salts thereof |
| US3494964A (en) * | 1969-01-13 | 1970-02-10 | Lilly Co Eli | Alpha-halo-alpha-amino ketones |
| DE3541181A1 (de) * | 1985-11-21 | 1987-05-27 | Basf Ag | Propylamine, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US5250732A (en) * | 1991-07-18 | 1993-10-05 | Genentech, Inc. | Ketamine analogues for treatment of thrombocytopenia |
| DE4409671C1 (de) * | 1994-03-15 | 1995-03-23 | Detlef Dr Preiss | Verwendung von 2-Methylamino-2-phenylcyclohexanon zur Behandlung von Bakterien-, Pilz-, Virus-, oder Protozoeninfektionen und zur Immunmodulation |
| US6197830B1 (en) | 1995-09-22 | 2001-03-06 | Bruce M. Frome | Method for achieving relief from sympathetically mediated pain |
| DE10025946A1 (de) * | 2000-05-26 | 2001-11-29 | Gruenenthal Gmbh | Wirkstoffkombination |
| US20040082543A1 (en) * | 2002-10-29 | 2004-04-29 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and NMDA receptor antagonists for the treatment or prevention of neuropathic pain |
| US20060063802A1 (en) * | 2004-03-29 | 2006-03-23 | Matthieu Guitton | Methods for the treatment of tinnitus induced by cochlear excitotoxicity |
| US8268866B2 (en) * | 2004-03-29 | 2012-09-18 | Matthieu Guitton | Methods for the treatment of tinnitus induced by cochlear excitotoxicity |
| US9072662B2 (en) | 2004-03-29 | 2015-07-07 | Auris Medical Ag | Methods for the treatment of tinnitus induced by cochlear excitotoxicity |
| DE102005004343A1 (de) * | 2005-01-25 | 2006-08-10 | Eberhard-Karls-Universität Tübingen Universitätsklinikum | Behandlung von Phantomphänomenen |
| EP1928405B1 (en) | 2005-09-28 | 2014-09-24 | Auris Medical AG | Pharmaceutical compositions for the treatment of inner ear disorders |
| JP5941159B2 (ja) | 2011-12-12 | 2016-06-29 | オトラーヌム アーゲー | 聴覚系における塩素イオン共輸送体ｎｋｃｃ１の調節による耳鳴の治療 |
| HK1212673A1 (zh) * | 2012-10-08 | 2016-06-17 | 奥克兰服务有限公司 | 氯胺酮衍生物 |
| HRP20211629T1 (hr) | 2013-09-13 | 2022-02-04 | National University Corporation Chiba University | Primjena r-ketamina i njegove soli kao lijekova |
| WO2017087691A1 (en) | 2015-11-17 | 2017-05-26 | The Trustees Of Columbia University In The City Of New York | Pharmacological prophylactics against stress-induced affective disorders and their associated symptoms |
| EP3383429B1 (en) | 2015-11-30 | 2020-10-14 | INSERM - Institut National de la Santé et de la Recherche Médicale | Nmdar antagonists for the treatment of tumor angiogenesis |
| EP3442940A1 (en) | 2016-04-11 | 2019-02-20 | Clexio Biosciences Ltd. | Deuterated ketamine derivatives |
| US11491120B2 (en) | 2017-11-09 | 2022-11-08 | The Trustees Of Columbia University In The City Of New York | Pharmacological prophylactics against stress-induced affective disorders in females |
| WO2019094596A1 (en) | 2017-11-09 | 2019-05-16 | The Trustees Of Columbia University In The City Of New York | Biomarkers for efficacy of prophylactic treatments against stress-induced affective disorders |
| EP3505509A1 (en) * | 2017-12-29 | 2019-07-03 | Université de Liège | Methods for the preparation of arylcycloalkylamine derivatives |
| CN111936127A (zh) | 2018-02-15 | 2020-11-13 | 国立大学法人千叶大学 | 炎症性疾病或骨病的预防或治疗剂及医药组合物 |
| CN112533595A (zh) | 2018-05-04 | 2021-03-19 | 感知神经科学公司 | 治疗物质滥用的方法 |
| WO2020237748A1 (zh) * | 2019-05-24 | 2020-12-03 | 北京大学深圳研究生院 | 一种长效化合物的制备方法 |
| WO2022208144A1 (en) * | 2021-03-31 | 2022-10-06 | Supriya Lifescience Ltd | A crystalline form of 2-(2-chlorophenyl)-2-(methylamino) cyclohexanone hydrochloride and method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1159431B (de) * | 1961-08-18 | 1963-12-19 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von 1-Cyclohexyl-2-amino-propanon-(1) und dessen Salzen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB853775A (en) * | 1957-09-19 | 1960-11-09 | Parke Davis & Co | Pharmaceutical compositions and methods for producing phenylcyclohexane compounds |
| US3068236A (en) * | 1960-10-17 | 1962-12-11 | Olin Mathieson | N-(2-imino-2-phenylethyl)amines and a process for their preparation |
-
1962
- 1962-06-29 US US206188A patent/US3254124A/en not_active Expired - Lifetime
-
1963
- 1963-06-26 BR BR150196/63A patent/BR6350196D0/pt unknown
- 1963-06-28 DE DEST20790A patent/DE1293761B/de active Pending
- 1963-06-28 DE DE19631793315 patent/DE1793315B1/de active Granted
- 1963-08-13 FR FR944543A patent/FR2973M/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1159431B (de) * | 1961-08-18 | 1963-12-19 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von 1-Cyclohexyl-2-amino-propanon-(1) und dessen Salzen |
Also Published As
| Publication number | Publication date |
|---|---|
| US3254124A (en) | 1966-05-31 |
| DE1793315B1 (de) | 1972-05-25 |
| BR6350196D0 (pt) | 1973-04-26 |
| DE1793315C2 (cg-RX-API-DMAC7.html) | 1973-01-04 |
| FR2973M (fr) | 1964-11-30 |
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