IL133235A - 1-amino-alkylcyclohexane nmda receptor antagonists and pharmaceutical compositions comprising them - Google Patents

1-amino-alkylcyclohexane nmda receptor antagonists and pharmaceutical compositions comprising them

Info

Publication number: IL133235A
Authority: IL; Israel
Prior art keywords: amino; ethyl; compound; pharmaceutical composition; methyl
Prior art date: 1997-06-30

Application number

IL13323598A

Other languages

English (en)

Other versions

IL133235A0 (en

Original Assignee

Merz Pharma Gmbh & Co Kgaa

Priority date (The priority date 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 date listed.)

1997-06-30

Filing date

1998-06-24

Publication date

2004-02-19

1998-06-24 Application filed by Merz Pharma Gmbh & Co Kgaa filed Critical Merz Pharma Gmbh & Co Kgaa

2001-03-19 Publication of IL133235A0 publication Critical patent/IL133235A0/xx

2004-02-19 Publication of IL133235A publication Critical patent/IL133235A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 41
229940127523 NMDA Receptor Antagonists Drugs 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 66
150000003839 salts Chemical class 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 47
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
230000000694 effects Effects 0.000 claims description 17
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 9
241000282414 Homo sapiens Species 0.000 claims description 8
241001465754 Metazoa Species 0.000 claims description 8
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 8
239000000969 carrier Substances 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
RUUUZPJNWLBOMQ-UHFFFAOYSA-N n,1,3,3,5,5-hexamethylcyclohexan-1-amine Chemical compound CNC1(C)CC(C)(C)CC(C)(C)C1 RUUUZPJNWLBOMQ-UHFFFAOYSA-N 0.000 claims description 6
JVUYSNBGWFWRLJ-UHFFFAOYSA-N n-ethyl-1,3,3,5,5-pentamethylcyclohexan-1-amine Chemical compound CCNC1(C)CC(C)(C)CC(C)(C)C1 JVUYSNBGWFWRLJ-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
208000005176 Hepatitis C Diseases 0.000 claims description 5
241000700605 Viruses Species 0.000 claims description 5
230000003042 antagnostic effect Effects 0.000 claims description 5
230000000078 anti-malarial effect Effects 0.000 claims description 5
230000002519 immonomodulatory effect Effects 0.000 claims description 5
229940099433 NMDA receptor antagonist Drugs 0.000 claims description 3
239000003430 antimalarial agent Substances 0.000 claims description 3
239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 3
YKLPCZMZROZLJA-UHFFFAOYSA-N 1-ethyl-3,3,5,5-tetramethylcyclohexan-1-amine Chemical compound CCC1(N)CC(C)(C)CC(C)(C)C1 YKLPCZMZROZLJA-UHFFFAOYSA-N 0.000 claims description 2
OGZQTTHDGQBLBT-UHFFFAOYSA-N neramexane Chemical compound CC1(C)CC(C)(C)CC(C)(N)C1 OGZQTTHDGQBLBT-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 5
NBZGMQHFDNUNRQ-UHFFFAOYSA-N 3,3-diethyl-1,5,5-trimethylcyclohexan-1-amine Chemical compound CCC1(CC)CC(C)(C)CC(C)(N)C1 NBZGMQHFDNUNRQ-UHFFFAOYSA-N 0.000 claims 1
JINZKAFNDLFUEW-UHFFFAOYSA-N 3-ethyl-1,3,5,5-tetramethylcyclohexan-1-amine Chemical compound CCC1(C)CC(C)(C)CC(C)(N)C1 JINZKAFNDLFUEW-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
SGPWXFVFSVUKME-UHFFFAOYSA-N n,1,3,3,5-pentamethylcyclohexan-1-amine Chemical compound CNC1(C)CC(C)CC(C)(C)C1 SGPWXFVFSVUKME-UHFFFAOYSA-N 0.000 abstract 1
239000000203 mixture Substances 0.000 description 45
239000000243 solution Substances 0.000 description 45
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
238000002360 preparation method Methods 0.000 description 24
235000002639 sodium chloride Nutrition 0.000 description 23
239000004480 active ingredient Substances 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000011780 sodium chloride Substances 0.000 description 14
101150041968 CDC13 gene Proteins 0.000 description 13
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
210000004027 cell Anatomy 0.000 description 13
238000009472 formulation Methods 0.000 description 13
238000012360 testing method Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000002609 medium Substances 0.000 description 10
-1 ES 242S Chemical compound 0.000 description 9
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
230000027455 binding Effects 0.000 description 8
239000012043 crude product Substances 0.000 description 8
206010010904 Convulsion Diseases 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000036461 convulsion Effects 0.000 description 7
238000000338 in vitro Methods 0.000 description 7
238000001727 in vivo Methods 0.000 description 7
230000036515 potency Effects 0.000 description 7
239000000725 suspension Substances 0.000 description 7
230000036967 uncompetitive effect Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000004471 Glycine Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000008485 antagonism Effects 0.000 description 6
230000002082 anti-convulsion Effects 0.000 description 6
150000001934 cyclohexanes Chemical class 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
238000011534 incubation Methods 0.000 description 6
239000011777 magnesium Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
ZUYKJZQOPXDNOK-UHFFFAOYSA-N 2-(ethylamino)-2-thiophen-2-ylcyclohexan-1-one;hydrochloride Chemical class Cl.C=1C=CSC=1C1(NCC)CCCCC1=O ZUYKJZQOPXDNOK-UHFFFAOYSA-N 0.000 description 5
OQJMHUOCLRCSED-UHFFFAOYSA-N 3,3,5,5-tetramethylcyclohexan-1-one Chemical compound CC1(C)CC(=O)CC(C)(C)C1 OQJMHUOCLRCSED-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
241000700159 Rattus Species 0.000 description 5
229930006000 Sucrose Natural products 0.000 description 5
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 5
239000005557 antagonist Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
208000015114 central nervous system disease Diseases 0.000 description 5
210000003618 cortical neuron Anatomy 0.000 description 5
JBBJFKIJUJEHRH-UHFFFAOYSA-N ethyl 2-(3,3,5,5-tetramethylcyclohexyl)acetate Chemical compound CCOC(=O)CC1CC(C)(C)CC(C)(C)C1 JBBJFKIJUJEHRH-UHFFFAOYSA-N 0.000 description 5
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
230000003492 excitotoxic effect Effects 0.000 description 5
231100000063 excitotoxicity Toxicity 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
239000012528 membrane Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 5
239000008213 purified water Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
230000003595 spectral effect Effects 0.000 description 5
229960004793 sucrose Drugs 0.000 description 5
BMRINMQQUFUCHR-UHFFFAOYSA-N 1,3,3,5,5-pentamethylcyclohexan-1-ol Chemical compound CC1(C)CC(C)(C)CC(C)(O)C1 BMRINMQQUFUCHR-UHFFFAOYSA-N 0.000 description 4
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
206010003591 Ataxia Diseases 0.000 description 4
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
229940127351 Uncompetitive NMDA Receptor Antagonists Drugs 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
229930195712 glutamate Natural products 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
239000012280 lithium aluminium hydride Substances 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
239000002105 nanoparticle Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000007920 subcutaneous administration Methods 0.000 description 4
230000024587 synaptic transmission, glutamatergic Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
229940075614 colloidal silicon dioxide Drugs 0.000 description 3
239000003636 conditioned culture medium Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 3
235000013681 dietary sucrose Nutrition 0.000 description 3
239000003814 drug Substances 0.000 description 3
206010015037 epilepsy Diseases 0.000 description 3
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
150000003840 hydrochlorides Chemical class 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
230000000978 myorelaxation Effects 0.000 description 3
239000008188 pellet Substances 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
238000007747 plating Methods 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
229960002668 sodium chloride Drugs 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
231100001274 therapeutic index Toxicity 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
WXONXIOSNYEXNX-UHFFFAOYSA-N 2-(3,3,5,5-tetramethylcyclohexyl)ethanol Chemical compound CC1(C)CC(CCO)CC(C)(C)C1 WXONXIOSNYEXNX-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
VJOWHRBAXBIQDR-UHFFFAOYSA-N 2-methyl-1-(3,3,5,5-tetramethylcyclohexyl)propan-2-ol Chemical compound CC(C)(O)CC1CC(C)(C)CC(C)(C)C1 VJOWHRBAXBIQDR-UHFFFAOYSA-N 0.000 description 2
OMYKWZGACJRFAJ-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-propylcyclohexan-1-amine Chemical compound CCCC1(N)CC(C)(C)CC(C)(C)C1 OMYKWZGACJRFAJ-UHFFFAOYSA-N 0.000 description 2
HALCXXAVLJHSTJ-UHFFFAOYSA-N 3-ethoxy-5,5-dimethylcyclohex-2-en-1-one Chemical compound CCOC1=CC(=O)CC(C)(C)C1 HALCXXAVLJHSTJ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
108091006146 Channels Proteins 0.000 description 2
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
102000016911 Deoxyribonucleases Human genes 0.000 description 2
108010053770 Deoxyribonucleases Proteins 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
239000007995 HEPES buffer Substances 0.000 description 2
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 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
208000018737 Parkinson disease Diseases 0.000 description 2
229920002730 Poly(butyl cyanoacrylate) Polymers 0.000 description 2
241000350158 Prioria balsamifera Species 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 2
229960003805 amantadine Drugs 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
239000012131 assay buffer Substances 0.000 description 2
210000001130 astrocyte Anatomy 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
244000309464 bull Species 0.000 description 2
AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
239000006285 cell suspension Substances 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
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
238000010219 correlation analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000006735 deficit Effects 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
206010013663 drug dependence Diseases 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
XSIUZCPGSAKPOY-UHFFFAOYSA-N ethyl 2-cyano-2-(1,3,3,5,5-pentamethylcyclohexyl)acetate Chemical compound CCOC(=O)C(C#N)C1(C)CC(C)(C)CC(C)(C)C1 XSIUZCPGSAKPOY-UHFFFAOYSA-N 0.000 description 2
PRQQYOOUHLGISO-UHFFFAOYSA-N ethyl 2-cyano-2-(3,3,5,5-tetramethylcyclohexylidene)acetate Chemical compound CCOC(=O)C(C#N)=C1CC(C)(C)CC(C)(C)C1 PRQQYOOUHLGISO-UHFFFAOYSA-N 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
239000012894 fetal calf serum Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000002518 glial effect Effects 0.000 description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
208000014674 injury Diseases 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
208000028867 ischemia Diseases 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000007758 minimum essential medium Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
230000004973 motor coordination Effects 0.000 description 2
FLKDCOXDLOAGMV-UHFFFAOYSA-N n,1,3,3,5,5-hexamethylcyclohexan-1-amine;hydrochloride Chemical compound Cl.CNC1(C)CC(C)(C)CC(C)(C)C1 FLKDCOXDLOAGMV-UHFFFAOYSA-N 0.000 description 2
210000002569 neuron Anatomy 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
229950010883 phencyclidine Drugs 0.000 description 2
229920000729 poly(L-lysine) polymer Polymers 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
230000000506 psychotropic effect Effects 0.000 description 2
239000002464 receptor antagonist Substances 0.000 description 2
229940044551 receptor antagonist Drugs 0.000 description 2
230000011514 reflex Effects 0.000 description 2
230000004044 response Effects 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
230000035939 shock Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
208000011117 substance-related disease Diseases 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000007916 tablet composition Substances 0.000 description 2
238000011287 therapeutic dose Methods 0.000 description 2
229940098465 tincture Drugs 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
230000008733 trauma Effects 0.000 description 2
230000003442 weekly effect Effects 0.000 description 2
SSJNMFPQWNHVBU-UHFFFAOYSA-N (3,3,5,5-tetramethylcyclohexyl)methanamine;hydrochloride Chemical compound Cl.CC1(C)CC(CN)CC(C)(C)C1 SSJNMFPQWNHVBU-UHFFFAOYSA-N 0.000 description 1
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
QHDHNVFIKWGRJR-UHFFFAOYSA-N 1-cyclohexenol Chemical class OC1=CCCCC1 QHDHNVFIKWGRJR-UHFFFAOYSA-N 0.000 description 1
UHGZQGRPVLAYLW-UHFFFAOYSA-N 2-(3,3,5,5-tetramethylcyclohexyl)ethyl methanesulfonate Chemical compound CC1(C)CC(CCOS(C)(=O)=O)CC(C)(C)C1 UHGZQGRPVLAYLW-UHFFFAOYSA-N 0.000 description 1
YSGASDXSLKIKOD-UHFFFAOYSA-N 2-amino-N-(1,2-diphenylpropan-2-yl)acetamide Chemical compound C=1C=CC=CC=1C(C)(NC(=O)CN)CC1=CC=CC=C1 YSGASDXSLKIKOD-UHFFFAOYSA-N 0.000 description 1
AMZSLPUETUJXMD-UHFFFAOYSA-N 5-(2-azidoethyl)-1,1,3,3-tetramethylcyclohexane Chemical compound CC1(C)CC(CCN=[N+]=[N-])CC(C)(C)C1 AMZSLPUETUJXMD-UHFFFAOYSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
208000024827 Alzheimer disease Diseases 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
208000019901 Anxiety disease Diseases 0.000 description 1
238000012371 Aseptic Filling Methods 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
239000012583 B-27 Supplement Substances 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
101100483112 Caenorhabditis elegans ttx-3 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
108091005462 Cation channels Proteins 0.000 description 1
208000000094 Chronic Pain Diseases 0.000 description 1
244000183685 Citrus aurantium Species 0.000 description 1
235000007716 Citrus aurantium Nutrition 0.000 description 1
240000002319 Citrus sinensis Species 0.000 description 1
235000005976 Citrus sinensis Nutrition 0.000 description 1
229920002261 Corn starch Polymers 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
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
206010052804 Drug tolerance Diseases 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
229930182566 Gentamicin Natural products 0.000 description 1
102000018899 Glutamate Receptors Human genes 0.000 description 1
108010027915 Glutamate Receptors Proteins 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
208000006264 Korsakoff syndrome Diseases 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
208000026072 Motor neurone disease Diseases 0.000 description 1
208000001089 Multiple system atrophy Diseases 0.000 description 1
208000008238 Muscle Spasticity Diseases 0.000 description 1
108010064983 Ovomucin Proteins 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
206010043118 Tardive Dyskinesia Diseases 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
208000009205 Tinnitus Diseases 0.000 description 1
206010043994 Tonic convulsion 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
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
102000004142 Trypsin Human genes 0.000 description 1
108090000631 Trypsin Proteins 0.000 description 1
201000004810 Vascular dementia Diseases 0.000 description 1
201000008485 Wernicke-Korsakoff syndrome Diseases 0.000 description 1
238000001793 Wilcoxon signed-rank test Methods 0.000 description 1
KWEWNAXCUWXEHQ-UHFFFAOYSA-M [I-].CCC[Mg+] Chemical compound [I-].CCC[Mg+] KWEWNAXCUWXEHQ-UHFFFAOYSA-M 0.000 description 1
239000013543 active substance Substances 0.000 description 1
208000005298 acute pain Diseases 0.000 description 1
IFLVGRRVGPXYON-UHFFFAOYSA-N adci Chemical compound C12=CC=CC=C2C2(C(=O)N)C3=CC=CC=C3CC1N2 IFLVGRRVGPXYON-UHFFFAOYSA-N 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 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
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
QIHLUZAFSSMXHQ-UHFFFAOYSA-N budipine Chemical compound C1CN(C(C)(C)C)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QIHLUZAFSSMXHQ-UHFFFAOYSA-N 0.000 description 1
229960002452 budipine Drugs 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 description 1
229960004195 carvedilol Drugs 0.000 description 1
230000004663 cell proliferation Effects 0.000 description 1
230000003833 cell viability Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
229960003920 cocaine Drugs 0.000 description 1
238000007398 colorimetric assay Methods 0.000 description 1
238000004590 computer program Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
LBOJYSIDWZQNJS-CVEARBPZSA-N dizocilpine Chemical compound C12=CC=CC=C2[C@]2(C)C3=CC=CC=C3C[C@H]1N2 LBOJYSIDWZQNJS-CVEARBPZSA-N 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000012154 double-distilled water Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000009509 drug development Methods 0.000 description 1
238000003372 electrophysiological method Methods 0.000 description 1
210000002257 embryonic structure Anatomy 0.000 description 1
JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 1
229950010048 enbucrilate Drugs 0.000 description 1
CCRRWMXDTVMKJD-UHFFFAOYSA-N ethyl 2-(3,3,5,5-tetramethylcyclohexylidene)acetate Chemical compound CCOC(=O)C=C1CC(C)(C)CC(C)(C)C1 CCRRWMXDTVMKJD-UHFFFAOYSA-N 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229960003472 felbamate Drugs 0.000 description 1
WKGXYQFOCVYPAC-UHFFFAOYSA-N felbamate Chemical compound NC(=O)OCC(COC(N)=O)C1=CC=CC=C1 WKGXYQFOCVYPAC-UHFFFAOYSA-N 0.000 description 1
230000001605 fetal effect Effects 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
210000004744 fore-foot Anatomy 0.000 description 1
239000012737 fresh medium Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000009454 functional inhibition Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
208000007386 hepatic encephalopathy Diseases 0.000 description 1
210000004295 hippocampal neuron Anatomy 0.000 description 1
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000036512 infertility Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
231100000225 lethality Toxicity 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
230000007774 longterm Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
229960004640 memantine Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
RXCRERJDURGKRL-UHFFFAOYSA-N methyl n-methyl-n-(1,3,3,5,5-pentamethylcyclohexyl)carbamate Chemical compound COC(=O)N(C)C1(C)CC(C)(C)CC(C)(C)C1 RXCRERJDURGKRL-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
230000002025 microglial effect Effects 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
210000003470 mitochondria Anatomy 0.000 description 1
230000004065 mitochondrial dysfunction Effects 0.000 description 1
230000011278 mitosis Effects 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
230000001670 myorelaxant effect Effects 0.000 description 1
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
JBKMIOMRWFWTRG-UHFFFAOYSA-N n-(1,3,3,5,5-pentamethylcyclohexyl)acetamide Chemical compound CC(=O)NC1(C)CC(C)(C)CC(C)(C)C1 JBKMIOMRWFWTRG-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
230000004770 neurodegeneration Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
210000004498 neuroglial cell Anatomy 0.000 description 1
239000004090 neuroprotective agent Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
210000004248 oligodendroglia Anatomy 0.000 description 1
208000031237 olivopontocerebellar atrophy Diseases 0.000 description 1
229940005483 opioid analgesics Drugs 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002913 oxalic acids Chemical class 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229960000502 poloxamer Drugs 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229950000659 remacemide Drugs 0.000 description 1
238000009877 rendering Methods 0.000 description 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000010825 rotarod performance test Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
208000018198 spasticity Diseases 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 1
229950010357 tetrodotoxin Drugs 0.000 description 1
CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 1
231100000886 tinnitus Toxicity 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
238000012345 traction test Methods 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
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000012588 trypsin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- A61P25/14—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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/16—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings
- C07C211/17—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings containing only non-condensed rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
- 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)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Immunology (AREA)
Tropical Medicine & Parasitology (AREA)
Epidemiology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Psychology (AREA)
Gastroenterology & Hepatology (AREA)
Virology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL13323598A 1997-06-30 1998-06-24 1-amino-alkylcyclohexane nmda receptor antagonists and pharmaceutical compositions comprising them IL133235A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US88594497A	1997-06-30	1997-06-30
PCT/EP1998/004026 WO1999001416A2 (fr)	1997-06-30	1998-06-24	1-aminoalkylcyclohexanes antagonistes du recepteur de nmda

Publications (2)

Publication Number	Publication Date
IL133235A0 IL133235A0 (en)	2001-03-19
IL133235A true IL133235A (en)	2004-02-19

Family

ID=25388050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13323598A IL133235A (en)	1997-06-30	1998-06-24	1-amino-alkylcyclohexane nmda receptor antagonists and pharmaceutical compositions comprising them

Country Status (25)

Country	Link
US (1)	US6034134A (fr)
EP (1)	EP1009732B1 (fr)
JP (1)	JP3963488B2 (fr)
KR (1)	KR100630506B1 (fr)
CN (1)	CN1136187C (fr)
AR (1)	AR010708A1 (fr)
AT (1)	ATE240936T1 (fr)
AU (1)	AU724974B2 (fr)
CA (1)	CA2292558C (fr)
CZ (1)	CZ293248B6 (fr)
DE (1)	DE69814878T2 (fr)
DK (1)	DK1009732T3 (fr)
EA (1)	EA002254B1 (fr)
ES (1)	ES2200358T3 (fr)
FI (1)	FI119809B (fr)
GE (1)	GEP20032995B (fr)
HU (1)	HU226110B1 (fr)
IL (1)	IL133235A (fr)
NO (1)	NO314353B1 (fr)
PL (1)	PL193237B1 (fr)
PT (1)	PT1009732E (fr)
TW (1)	TW593225B (fr)
UA (1)	UA61962C2 (fr)
WO (1)	WO1999001416A2 (fr)
ZA (1)	ZA985678B (fr)

Families Citing this family (147)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7135584B2 (en) *	1995-08-07	2006-11-14	Wake Forest University	Lipid analogs for treating viral infections
EP0781138B1 (fr)	1994-08-29	2008-05-21	Wake Forest University	Analogues de lipides pour le traitement d'infections virales
UA72558C2 (uk) *	1999-11-01	2005-03-15	Мерц Фарма Гмбх Унд Ко. Кгаа	1-аміноалкілциклогексанові антагоністи рецептора nmda
US6444702B1 (en)	2000-02-22	2002-09-03	Neuromolecular, Inc.	Aminoadamantane derivatives as therapeutic agents
PY0111577A (es)	2000-05-23	2017-01-02	Idenix Cayman Ltd	Métodos y composiciones para el tratamiento del virus de la hepatitis c
AP2006003708A0 (en)	2000-05-26	2006-08-31	Idenix Cayman Ltd	Methods and compositions for treating flavivirusesand pestiviruses
TW593223B (en)	2000-06-20	2004-06-21	Merz Pharma Gmbh & Co Kgaa	1-amino-alkylcyclohexanes as 5-HT3 and neuronal nicotinic receptor antagonists
US6602862B1 (en)	2000-09-19	2003-08-05	Merz Pharma Gmbh & Co., Kgaa	1-Amino-alkylcyclohexanes as trypanocidal agents
JP2004533406A (ja)	2000-10-18	2004-11-04	フアーマセツト・リミテツド	ウイルス感染症および異常細胞増殖を治療するための修飾ヌクレオシド
WO2002044717A1 (fr) *	2000-12-01	2002-06-06	Cornell Research Foundation	Modele animal d'infection par virus des flaviviridae
AU2002232660A1 (en) *	2000-12-15	2002-06-24	Pharmasset Ltd.	Antiviral agents for treatment of flaviviridae infections
WO2002072542A2 (fr) *	2001-03-08	2002-09-19	Emory University	Antagonistes du recepteur nmda dependant du ph
AU2002330154A1 (en) *	2001-09-28	2003-04-07	Centre National De La Recherche Scientifique	Methods and compositions for treating hepatitis c virus using 4'-modified nucleosides
US6828462B2 (en) *	2001-11-07	2004-12-07	Merz Pharma Gmbh & Co. Kgaa	Unsaturated 1-amino-alkylcyclohexane NMDA, 5HT3, and neuronal nicotinic receptor antagonists
WO2003068162A2 (fr) *	2002-02-14	2003-08-21	Pharmasset Ltd.	Analogues de nucleoside fluores modifies
PT1523489E (pt)	2002-06-28	2014-06-24	Centre Nat Rech Scient	Profármacos de nucleósido modificado em 2' e 3' para tratamento de infecções por flaviridae
EP1523309A2 (fr) *	2002-07-19	2005-04-20	Khalid Iqbal	Antagonistes du recepteur nmda et leur utilisation pour inhiber l'hyperphosphorylation de la proteine associee aux microtubules tau
JP2006507235A (ja) *	2002-08-01	2006-03-02	フアーマセツト・インコーポレイテツド	フラビウイルス科ウイルス感染治療のためのビシクロ［４．２．１］ノナン系を有する化合物
AU2003274353B2 (en)	2002-10-24	2007-04-05	Merz Pharma Gmbh & Co. Kgaa	Combination therapy using 1-aminocyclohexane derivatives and acetylcholinesterase inhibitors
RU2005118421A (ru)	2002-11-15	2006-01-20	Айденикс (Кайман) Лимитед (Ky)	2'-разветвленные нуклеозиды и мутация flaviviridae
US7732162B2 (en)	2003-05-05	2010-06-08	Probiodrug Ag	Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases
MXPA05012493A (es) *	2003-05-27	2006-05-25	Forest Laboratories	Combinacion de un antagonista del receptor de nmda y un inhibidor selectivo de reabsorcion de serotonina para el tratamiento de depresion y otros trastornos de estado de animo.
BRPI0419345B8 (pt)	2003-05-30	2021-05-25	Gilead Pharmasset Llc	uso do (2r)-2-desoxi-2-flúor-2-c-metil nucleosídeo e de uma composição farmacêutica que o compreende
DK1658302T3 (da)	2003-07-25	2010-11-22	Idenix Pharmaceuticals Inc	Purinnukleosidanaloge til behandling af sygdomme forårsaget af Flavirividae, herunder hepatitis C
AU2004258751C1 (en) *	2003-07-28	2008-07-17	Merz Pharma Gmbh & Co. Kgaa	The use of 1-amino-alkylcyclohexane compounds in the treatment of pain hypersensitivity
US20050113458A1 (en) *	2003-10-22	2005-05-26	Forest Laboratories, Inc.	Use of 1-aminocyclohexane derivatives to modify deposition of fibrillogenic a-beta peptides in amyloidopathies
AR046314A1 (es)	2003-11-05	2005-11-30	Merz Pharma Gmbh & Co Kgaa	Composiciones que comprenden ciclohexilaminas y aminoadamantanos
UY28650A1 (es) *	2003-12-05	2005-02-28	Forest Laboratories	Memantina para la prevencion o disminucion de la conducta suicida y para el tratamiento de la depresion mayor asociada con esta conducta
GB0500020D0 (en)	2005-01-04	2005-02-09	Novartis Ag	Organic compounds
AU2005204358B2 (en) *	2004-01-05	2008-09-04	Merz Pharma Gmbh & Co. Kgaa	Memantine for the treatment of mild and mild-to-moderate Alzheimer's disease
US20050187191A1 (en) *	2004-02-20	2005-08-25	Kucera Louis S.	Methods and compositions for the treatment of respiratory syncytial virus
US20050187192A1 (en) *	2004-02-20	2005-08-25	Kucera Pharmaceutical Company	Phospholipids for the treatment of infection by togaviruses, herpes viruses and coronaviruses
TW200531680A (en) *	2004-03-03	2005-10-01	Merz Pharma Gmbh & Co Kgaa	Therapy using 1-aminocyclohexane derivatives for the treatment of behavioral disorders associated with alzheimer's disease
US20060002999A1 (en) *	2004-06-17	2006-01-05	Forest Laboratories, Inc.	Immediate release formulations of 1-aminocyclohexane compounds, memantine and neramexane
ES2483126T3 (es) *	2004-06-17	2014-08-05	Merz Pharma Gmbh & Co. Kgaa	Formulaciones de formas de dosificación de neramexano
JP2008503475A (ja) *	2004-06-17	2008-02-07	フォーレストラボラトリーズ，インコーポレイテッド	メマンチンの放出が改変された製剤
WO2006000922A2 (fr) *	2004-06-23	2006-01-05	Idenix (Cayman) Limited	Derives de 5-aza-7-deazapurine pour le traitement des flaviviridae
CN101023094B (zh) *	2004-07-21	2011-05-18	法莫赛特股份有限公司	烷基取代的2-脱氧-2-氟代-d-呋喃核糖基嘧啶和嘌呤及其衍生物的制备
MX2007003085A (es)	2004-09-14	2007-08-02	Pharmasset Inc	Preparacion de 2'-fluoro-2'-alquilo sustituido u otras ribofuranosil pirimidinas y purinas opcionalmente sustituidas y sus derivados.
TW200621677A (en) *	2004-09-21	2006-07-01	Astellas Pharma Inc	Cyclic amine derivative or salt thereof
US20060205822A1 (en) *	2004-12-22	2006-09-14	Forest Laboratories, Inc.	1-Aminocyclohexane derivatives for the treatment of multiple sclerosis, emotional lability and pseudobulbar affect
EA013474B1 (ru) *	2005-06-16	2010-04-30	Форест Лэборэтериз, Инк.	Композиция в виде гранул с модифицированным и немедленным высвобождением мемантина
US20070099947A1 (en) *	2005-11-03	2007-05-03	Alkermes, Inc.	Methods and compositions for the treatment of brain reward system disorders by combination therapy
US20070141148A1 (en) *	2005-11-30	2007-06-21	Merz Pharma Gmbh & Co. Kgaa	Neramexane MR matrix tablet
CA2643680A1 (fr)	2006-04-11	2007-11-22	Novartis Ag	Composes organiques et leurs utilisations
WO2008005534A2 (fr) *	2006-07-06	2008-01-10	Forest Laboratories, Inc.	Formulations à dissolution orale de mémantine
KR101389209B1 (ko)	2006-07-18	2014-04-24	아스텔라스세이야쿠 가부시키가이샤	아미노인단 유도체 또는 그의 염
US7985753B2 (en)	2006-08-04	2011-07-26	Merz Pharma Gmbh & Co. Kgaa	Substituted pyrazolo[1,5-A]pyrimidines as metabotropic glutamate receptor modulators
US8278345B2 (en)	2006-11-09	2012-10-02	Probiodrug Ag	Inhibitors of glutaminyl cyclase
JP5523107B2 (ja)	2006-11-30	2014-06-18	プロビオドルグエージー	グルタミニルシクラーゼの新規阻害剤
WO2008106167A1 (fr) *	2007-02-28	2008-09-04	Conatus Pharmaceuticals, Inc.	Polythérapie incluant des inhibiteurs de métalloprotéinases matricielles et des inhibiteurs de caspases pour le traitement de maladies hépatiques
BRPI0808089A2 (pt) *	2007-02-28	2014-07-15	Conatus Pharmaceuticals Inc	Método para tratar uma doença do fígado, para diminuir um nível elevado de uma enzima do fígado, para inibir uma cascata de sinalização de tnf-alfa e uma cascata de sinalização de alfa-faz, para reduzir um dano ao fígado, para suprimir a apoptose excessiva em uma célula de fígado, e para inibir a replicação do vírus da hepatite c.
EP2481408A3 (fr)	2007-03-01	2013-01-09	Probiodrug AG	Nouvelle utilisation d'inhibiteurs glutaminyle cyclase
US7964580B2 (en)	2007-03-30	2011-06-21	Pharmasset, Inc.	Nucleoside phosphoramidate prodrugs
WO2008128985A1 (fr)	2007-04-18	2008-10-30	Probiodrug Ag	Dérivés de thio-urée utilisés comme inhibiteurs de la glutaminyl cyclase
TW200916091A (en) *	2007-06-08	2009-04-16	Merz Pharma Gmbh & Amp Co Kgaa	Neramexane for the treatment of nystagmus
CN103058957A (zh)	2007-06-29	2013-04-24	埃莫里大学	用于神经保护的nmda受体拮抗剂
EP2018854A1 (fr) *	2007-07-27	2009-01-28	Merz Pharma GmbH & Co. KGaA	Nouvelles combinaisons de néramexane pour le traitement des troubles neuro-dégénératifs
RU2446794C2 (ru) *	2007-09-12	2012-04-10	Мерц Фарма Гмбх Унд Ко. Кгаа	Терапия с интервалами для лечения тиннитуса
ATE532507T1 (de)	2007-09-12	2011-11-15	Merz Pharma Gmbh & Co Kgaa	Neramexane zur behandlung von subakuten tinnitus
EP2085398A1 (fr)	2008-02-01	2009-08-05	Merz Pharma GmbH & Co. KGaA	Pyrazolopyrimidines, leur procédé de préparation et leur utilisation en tant que médicament
EP2090576A1 (fr)	2008-02-01	2009-08-19	Merz Pharma GmbH & Co.KGaA	6-halo-pyrazolo[1,5-a]pyridines, leur procédé de préparation et leur utilisation en tant que modulateurs des récepteurs metabotropiques du glutamate (mGluR)
TW200946541A (en) *	2008-03-27	2009-11-16	Idenix Pharmaceuticals Inc	Solid forms of an anti-HIV phosphoindole compound
US20090247644A1 (en) *	2008-03-28	2009-10-01	Forest Laboratories Holdings Limited	Memantine formulations
US20110034565A1 (en)	2008-04-18	2011-02-10	University College Dublin, National University Of Ireland, Dublin	Psycho-pharmaceuticals
EP2111858A1 (fr)	2008-04-25	2009-10-28	EPFL Ecole Polytechnique Fédérale de Lausanne	Nouveau traitement pour la maladie d'Alzheimer
US20090275597A1 (en) *	2008-05-02	2009-11-05	Forest Laboratories Holdings Limited	Methods of treating cns disorders
US8173621B2 (en)	2008-06-11	2012-05-08	Gilead Pharmasset Llc	Nucleoside cyclicphosphates
TW201010691A (en) *	2008-06-12	2010-03-16	Merz Pharma Gmbh & Co Kgaa	1-amino-alkylcyclohexane derivatives for the treatment of sleep disorders
TW201006463A (en) *	2008-06-26	2010-02-16	Merz Pharma Gmbh & Co Kgaa	Pharmaceutical compositions comprising aminocyclohexane derivatives
WO2010014134A1 (fr)	2008-07-02	2010-02-04	Idenix Pharamaceuticals, Inc.	Composés et compositions pharmaceutiques pour le traitement d'infections virales
UA105182C2 (ru)	2008-07-03	2014-04-25	Ньюрексон, Інк.	Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность
CA2737335C (fr) *	2008-12-19	2013-10-01	Merz Pharma Gmbh & Co. Kgaa	Derives de 1-amino-alkylcyclohexane dans le traitement de maladies mediees par des mastocytes
TWI432188B (zh)	2008-12-19	2014-04-01	Merz Pharma Gmbh & Co Kgaa	供治療發炎性皮膚疾病之１－胺基－烷基環己烷衍生物類
CL2009002206A1 (es)	2008-12-23	2011-08-26	Gilead Pharmasset Llc	Compuestos derivados de pirrolo -(2-3-d]-pirimidin-7(6h)-tetrahidrofuran-2-il fosfonamidato, composicion farmaceutica; y su uso en el tratamiento de enfermedades virales.
JP6104504B2 (ja)	2008-12-23	2017-03-29	ギリアドファーマセットエルエルシー	ヌクレオシド類似体
TW201026715A (en)	2008-12-23	2010-07-16	Pharmasset Inc	Nucleoside phosphoramidates
JP5690286B2 (ja)	2009-03-04	2015-03-25	イデニクプハルマセウティカルス，インコーポレイテッド	ホスホチオフェン及びホスホチアゾールｈｃｖポリメラーゼ阻害剤
US8512690B2 (en)	2009-04-10	2013-08-20	Novartis Ag	Derivatised proline containing peptide compounds as protease inhibitors
US20110182850A1 (en)	2009-04-10	2011-07-28	Trixi Brandl	Organic compounds and their uses
CN102438981B (zh) *	2009-04-17	2015-04-22	德国麦氏大药厂	1-氨基-1,3,3,5,5-五甲基环己烷甲磺酸盐的合成
US8618076B2 (en)	2009-05-20	2013-12-31	Gilead Pharmasset Llc	Nucleoside phosphoramidates
TWI583692B (zh)	2009-05-20	2017-05-21	基利法瑪席特有限責任公司	核苷磷醯胺
WO2011000537A1 (fr)	2009-06-29	2011-01-06	Merz Pharma Gmbh & Co. Kgaa	Procédé de préparation de 1-chloroacétamido-1,3,3,5,5-pentaméthylcyclohexane
CA2765741A1 (fr) *	2009-06-29	2011-01-06	Merz Pharma Gmbh & Co. Kgaa	Procede de preparation de 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane
BRPI1012669A2 (pt) *	2009-06-29	2016-04-05	Merz Pharma Gmbh & Co Kgaa	metodo de preparacao de 3,3,5,5-tetrametliciclohexanona, método de preparção de 1-amino-1,3,3,5,5,-pentametilciclohexano ou um sal farmaceuticamente aceitável do mesmo e composto
TW201116532A (en)	2009-08-05	2011-05-16	Merz Pharma Gmbh & Co Kgaa	Metabotropic glutamate receptor modulators
US9284307B2 (en)	2009-08-05	2016-03-15	Idenix Pharmaceuticals Llc	Macrocyclic serine protease inhibitors
MX2012002993A (es)	2009-09-11	2012-04-19	Probiodrug Ag	Derivados heterociclicos como inhibidores de ciclasa glutaminilo.
JP2013505902A (ja) *	2009-09-28	2013-02-21	メルツファーマゲゼルシャフトミットベシュレンクテルハフツングウントコンパニーコマンディトゲゼルシャフトアウフアクティーン	ネラメキサン又はその塩を調製する方法
US20110117055A1 (en)	2009-11-19	2011-05-19	Macdonald James E	Methods of Treating Hepatitis C Virus with Oxoacetamide Compounds
SG181797A1 (en)	2009-12-18	2012-07-30	Idenix Pharmaceuticals Inc	5,5-fused arylene or heteroarylene hepatitis c virus inhibitors
JP6026284B2 (ja)	2010-03-03	2016-11-16	プロビオドルグエージー	グルタミニルシクラーゼの阻害剤
US8269019B2 (en)	2010-03-10	2012-09-18	Probiodrug Ag	Inhibitors
PL3290428T3 (pl)	2010-03-31	2022-02-07	Gilead Pharmasset Llc	Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu
CL2011000716A1 (es)	2010-03-31	2012-04-20	Gilead Pharmasset Llc	Formas cristalinas 1 6 de (s)-isopropil-2-(((s)-(((2r.3r.4r.5r)-5-(2,4-dioxo-3,4-dihidropirimidin-1(2h)-il)-4-fluoro-3-hidroxi-4-metil tetrahidrofuran-2-il)metoxi)(fenoxi)fosforil)amino)propanoato; composicion y combinacion farmaceutica; y su uso para tratar una infeccion por el virus de la hepatitis c.
TWI515000B (zh)	2010-04-01	2016-01-01	伊迪尼克製藥公司	用於治療病毒感染之化合物及醫藥組合物
WO2011131748A2 (fr)	2010-04-21	2011-10-27	Probiodrug Ag	Nouveaux inhibiteurs
US20110294890A1 (en)	2010-05-28	2011-12-01	Merz Pharma Gmbh & Co. Kgaa	Neramexane for the treatment or prevention of inner ear disorders
MX2012012318A (es) *	2010-06-18	2012-11-21	Merz Pharma Gmbh & Co Kgaa	Formulaciones en gel para el uso topico de derivados de 1-amino-alquiciclohexano.
EP2624826B1 (fr)	2010-10-08	2018-07-18	Novartis AG	Compositions comprenant de la vitamine e et des sulfamides inhibiteurs du ns3
WO2012048871A1 (fr)	2010-10-12	2012-04-19	Merz Pharma Gmbh & Co. Kgaa	Mémantine pour l'amélioration de la performance cognitive chez des sujets
WO2012075140A1 (fr)	2010-11-30	2012-06-07	Pharmasset, Inc.	Composés
WO2012080050A1 (fr)	2010-12-14	2012-06-21	F. Hoffmann-La Roche Ag	Formes solides d'un composé de phénoxybenzènesulfonyle
JP6084931B2 (ja)	2011-01-20	2017-02-22	メルツファーマゲゼルシャフトミットベシュレンクテルハフツングウントコンパニーコマンディトゲゼルシャフトアウフアクティーン	ストレス又は急性聴力損失に関連する耳鳴の治療又は予防のためのネラメキサン
US9353100B2 (en)	2011-02-10	2016-05-31	Idenix Pharmaceuticals Llc	Macrocyclic serine protease inhibitors, pharmaceutical compositions thereof, and their use for treating HCV infections
WO2012107584A1 (fr)	2011-02-11	2012-08-16	Universite Pierre Et Marie Curie (Paris 6)	Procédés de prédiction des résultats d'une infection par le virus de l'hépatite
ES2570167T3 (es)	2011-03-16	2016-05-17	Probiodrug Ag	Derivados de benzimidazol como inhibidores de glutaminil ciclasa
US20120252721A1 (en)	2011-03-31	2012-10-04	Idenix Pharmaceuticals, Inc.	Methods for treating drug-resistant hepatitis c virus infection with a 5,5-fused arylene or heteroarylene hepatitis c virus inhibitor
CN103842369A (zh)	2011-03-31	2014-06-04	埃迪尼克斯医药公司	用于治疗病毒感染的化合物和药物组合物
AU2012292032A1 (en)	2011-08-03	2014-03-13	Cytheris	HCV immunotherapy
AR088441A1 (es)	2011-09-12	2014-06-11	Idenix Pharmaceuticals Inc	Compuestos de carboniloximetilfosforamidato sustituido y composiciones farmaceuticas para el tratamiento de infecciones virales
WO2013039855A1 (fr)	2011-09-12	2013-03-21	Idenix Pharmaceuticals, Inc.	Composés et compositions pharmaceutiques pour le traitement d'infections virales
TW201331221A (zh)	2011-10-14	2013-08-01	Idenix Pharmaceuticals Inc	嘌呤核苷酸化合物類之經取代的３’，５’－環磷酸酯及用於治療病毒感染之醫藥組成物
US8889159B2 (en)	2011-11-29	2014-11-18	Gilead Pharmasset Llc	Compositions and methods for treating hepatitis C virus
CA3131037A1 (fr)	2011-11-30	2013-06-06	Emory University	Inhibiteurs de jak antiviraux utiles dans le traitement ou la prevention d'infections retrovirales et autres infections virales
US8809354B2 (en)	2011-12-31	2014-08-19	Sheikh Riazuddin	3-amino-2-(4-nitrophenyl)-4-(3H)-quinazolinone or derivatives thereof for treating or preventing antiviral infections
WO2013133927A1 (fr)	2012-02-13	2013-09-12	Idenix Pharmaceuticals, Inc.	Compositions pharmaceutiques de 2'-c-méthyl-guanosine, 5'-[2-[(3-hydroxy-2,2-diméthyl-1-oxopropyl)thio]éthyl n-(phénylméthyl)phosphoramidate]
US9296778B2 (en)	2012-05-22	2016-03-29	Idenix Pharmaceuticals, Inc.	3′,5′-cyclic phosphate prodrugs for HCV infection
AP3913A (en)	2012-05-22	2016-11-26	Idenix Pharamaceuticals Inc	D-amino acid compounds for liver disease
EP2852604B1 (fr)	2012-05-22	2017-04-12	Idenix Pharmaceuticals LLC	Promédicaments de 3',5'-phosphoramidate cyclique pour traiter une infection par le virus de l'hépatite c
RU2488388C1 (ru) *	2012-05-24	2013-07-27	Ооо "Валента Интеллект"	Фармацевтическая композиция для профилактики и лечения психических, поведенческих, когнитивных расстройств
UA107653U (uk)	2012-10-01	2016-06-24	Общєство С Огранічєнной Отвєтствєнностью "Валєнта-Інтєллєкт"	Композиція лікарських засобів для лікування та профілактики поведінкових, психічних та когнітивних розладів
SG11201502750UA (en)	2012-10-08	2015-06-29	Idenix Pharmaceuticals Inc	2'-chloro nucleoside analogs for hcv infection
US20140112886A1 (en)	2012-10-19	2014-04-24	Idenix Pharmaceuticals, Inc.	Dinucleotide compounds for hcv infection
EP2909222B1 (fr)	2012-10-22	2021-05-26	Idenix Pharmaceuticals LLC	Nucléosides 2', 4'-pontés pour l'infection par le vhc
EP2920195A1 (fr)	2012-11-14	2015-09-23	IDENIX Pharmaceuticals, Inc.	Ester de d-alanine d'analogue de rp-nucléoside
US20140140952A1 (en)	2012-11-14	2014-05-22	Idenix Pharmaceuticals, Inc.	D-Alanine Ester of Sp-Nucleoside Analog
EP2935304A1 (fr)	2012-12-19	2015-10-28	IDENIX Pharmaceuticals, Inc.	4'-fluoro-nucléosides pour le traitement du vhc
US9309275B2 (en)	2013-03-04	2016-04-12	Idenix Pharmaceuticals Llc	3′-deoxy nucleosides for the treatment of HCV
WO2014137930A1 (fr)	2013-03-04	2014-09-12	Idenix Pharmaceuticals, Inc.	Nucléosides de thiophosphate pour le traitement du vhc
EP2981542B1 (fr)	2013-04-01	2021-09-15	Idenix Pharmaceuticals LLC	2',4'-fluoronucléosides pour le traitement du vhc
US10005779B2 (en)	2013-06-05	2018-06-26	Idenix Pharmaceuticals Llc	1′,4′-thio nucleosides for the treatment of HCV
WO2015017713A1 (fr)	2013-08-01	2015-02-05	Idenix Pharmaceuticals, Inc.	Pronucléotides phosphoramidates avec acides aminés d de composés halogéno pyrimidines pour le traitement des hépatopathies
JP2016529293A (ja)	2013-08-27	2016-09-23	ギリアドファーマセットエルエルシー	２つの抗ウイルス化合物の組合せ製剤
WO2015042375A1 (fr)	2013-09-20	2015-03-26	Idenix Pharmaceuticals, Inc.	Inhibiteurs du virus de l'hépatite c
WO2015061683A1 (fr)	2013-10-25	2015-04-30	Idenix Pharmaceuticals, Inc.	Pronucléotides thiophosphoramidates à acide aminé d et pronucléotides thiophosphoramidates à d-analine de composés de nucléoside utiles pour le traitement du vhc
WO2015066370A1 (fr)	2013-11-01	2015-05-07	Idenix Pharmaceuticals, Inc.	Pronucléotides phosphoramidates de d-alanine de composés de nucléoside 2'-méthyl 2'-fluoro guanosine dans le traitement du vhc
EP3074399A1 (fr)	2013-11-27	2016-10-05	Idenix Pharmaceuticals LLC	Analogues de nucléoside 2'-dichloro et 2'-fluoro-2'-chloro analogues pour l'infection par le vhc
EP3083654A1 (fr)	2013-12-18	2016-10-26	Idenix Pharmaceuticals LLC	Nucléosides 4'-or pour le traitement du vhc
US20170066779A1 (en)	2014-03-05	2017-03-09	Idenix Pharmaceuticals Llc	Solid forms of a flaviviridae virus inhibitor compound and salts thereof
WO2015134561A1 (fr)	2014-03-05	2015-09-11	Idenix Pharmaceuticals, Inc.	Compositions pharmaceutiques comprenant un inhibiteur de flaviviridae hétéroarylène fusionné en 5,5 et son utilisation pour le traitement ou la prévention d'une infection par les flaviviridae
WO2015161137A1 (fr)	2014-04-16	2015-10-22	Idenix Pharmaceuticals, Inc.	Nucléosides méthyle ou alcynyle substitués en position 3 pour le traitement du virus de l'hépatite c
WO2018129609A1 (fr) *	2017-01-10	2018-07-19	Owen-Barry Pharmaceuticals Inc.	Composés anticonvulsivants
PL3461819T3 (pl)	2017-09-29	2020-11-30	Probiodrug Ag	Inhibitory cyklazy glutaminylowej
US20250161238A1 (en)	2022-02-08	2025-05-22	Fikret Sahin	NMDAR Antagonists Prevent Ageing and Aging-Associated Conditions and Diseases Through Increasing 20S Proteasome Activity
CN117658827A (zh) *	2022-09-01	2024-03-08	上海睿智化学研究有限公司	烷基环己基乙胺的合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3541181A1 (de) *	1985-11-21	1987-05-27	Basf Ag	Propylamine, verfahren zu ihrer herstellung und ihre verwendung als fungizide
US5084479A (en) *	1990-01-02	1992-01-28	Warner-Lambert Company	Novel methods for treating neurodegenerative diseases

1998
- 1998-06-24 UA UA2000010462A patent/UA61962C2/uk unknown
- 1998-06-24 EP EP98939579A patent/EP1009732B1/fr not_active Expired - Lifetime
- 1998-06-24 HU HU0100266A patent/HU226110B1/hu not_active IP Right Cessation
- 1998-06-24 TW TW087110177A patent/TW593225B/zh not_active IP Right Cessation
- 1998-06-24 ES ES98939579T patent/ES2200358T3/es not_active Expired - Lifetime
- 1998-06-24 JP JP50632399A patent/JP3963488B2/ja not_active Expired - Fee Related
- 1998-06-24 IL IL13323598A patent/IL133235A/en not_active IP Right Cessation
- 1998-06-24 WO PCT/EP1998/004026 patent/WO1999001416A2/fr not_active Ceased
- 1998-06-24 DE DE69814878T patent/DE69814878T2/de not_active Expired - Lifetime
- 1998-06-24 AT AT98939579T patent/ATE240936T1/de active
- 1998-06-24 EA EA200000080A patent/EA002254B1/ru not_active IP Right Cessation
- 1998-06-24 AU AU88042/98A patent/AU724974B2/en not_active Ceased
- 1998-06-24 PL PL337809A patent/PL193237B1/pl unknown
- 1998-06-24 DK DK98939579T patent/DK1009732T3/da active
- 1998-06-24 KR KR1019997011753A patent/KR100630506B1/ko not_active Expired - Fee Related
- 1998-06-24 GE GEAP19985193A patent/GEP20032995B/en unknown
- 1998-06-24 CZ CZ19994571A patent/CZ293248B6/cs not_active IP Right Cessation
- 1998-06-24 CN CNB988067757A patent/CN1136187C/zh not_active Expired - Fee Related
- 1998-06-24 CA CA002292558A patent/CA2292558C/fr not_active Expired - Fee Related
- 1998-06-24 PT PT98939579T patent/PT1009732E/pt unknown
- 1998-06-29 ZA ZA9805678A patent/ZA985678B/xx unknown
- 1998-06-30 AR ARP980103171A patent/AR010708A1/es active IP Right Grant
- 1998-08-27 US US09/141,381 patent/US6034134A/en not_active Expired - Lifetime
1999
- 1999-12-29 FI FI992801A patent/FI119809B/fi not_active IP Right Cessation
- 1999-12-29 NO NO19996548A patent/NO314353B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA985678B (en)	2000-01-10
DE69814878D1 (de)	2003-06-26
CZ457199A3 (cs)	2000-06-14
FI19992801L (fi)	1999-12-29
UA61962C2 (uk)	2003-12-15
DK1009732T3 (da)	2003-09-22
ATE240936T1 (de)	2003-06-15
NO996548D0 (no)	1999-12-29
KR20010013738A (ko)	2001-02-26
JP3963488B2 (ja)	2007-08-22
CA2292558C (fr)	2006-09-19
US6034134A (en)	2000-03-07
HU226110B1 (en)	2008-04-28
AR010708A1 (es)	2000-07-12
JP2002511873A (ja)	2002-04-16
EA200000080A1 (ru)	2000-08-28
TW593225B (en)	2004-06-21
CA2292558A1 (fr)	1999-01-14
FI119809B (fi)	2009-03-31
HUP0100266A3 (en)	2003-07-28
HUP0100266A2 (hu)	2002-05-29
NO996548L (no)	2000-02-28
CN1136187C (zh)	2004-01-28
WO1999001416A3 (fr)	1999-08-19
EP1009732A2 (fr)	2000-06-21
CZ293248B6 (cs)	2004-03-17
GEP20032995B (en)	2003-06-25
HK1029574A1 (en)	2001-04-06
IL133235A0 (en)	2001-03-19
PL193237B1 (pl)	2007-01-31
AU724974B2 (en)	2000-10-05
EP1009732B1 (fr)	2003-05-21
EA002254B1 (ru)	2002-02-28
CN1266423A (zh)	2000-09-13
PL337809A1 (en)	2000-09-11
DE69814878T2 (de)	2004-05-19
KR100630506B1 (ko)	2006-09-29
PT1009732E (pt)	2003-10-31
ES2200358T3 (es)	2004-03-01
NO314353B1 (no)	2003-03-10
AU8804298A (en)	1999-01-25
WO1999001416A2 (fr)	1999-01-14

Legal Events

Date	Code	Title
2004-07-25	FF	Patent granted
2008-08-10	KB	Patent renewed
2012-06-28	KB	Patent renewed
2017-01-31	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP1009732B1 (fr)	2003-05-21	1-aminoalkylcyclohexanes antagonistes du recepteur de nmda
US6071966A (en)	2000-06-06	1-amino-alkylcyclohexane NMDA receptor antagonists
US6828462B2 (en)	2004-12-07	Unsaturated 1-amino-alkylcyclohexane NMDA, 5HT3, and neuronal nicotinic receptor antagonists
US20070185151A1 (en)	2007-08-09	Azabicyclic, azatricyclic and azaspirocyclic derivatives of aminocyclohexane NMDA, 5HT3 and neuronal nicotinic receptor antagonists
AU2002337389A1 (en)	2003-07-24	Unsaturated 1-amino-alkylcyclohexane NMDA,5HT3 and neuronal nicotinic receptor antagonists
EP2277850A1 (fr)	2011-01-26	1-amino-alkylcyclohexanes en tant que 5-HT3 et antagonistes du récepteur nicotinique neuronale
MXPA99011993A (en)	2000-12-06	1-amino-alkylcyclohexane nmda receptor antagonists
ZA200403456B (en)	2005-05-19	Unsaturated 1-amino-alkylcyclohexane NMDA, 5HT3 and neuronal nicotinic receptor antagonists.
HK1075037B (en)	2009-06-19	Unsaturated 1-amino-alkylcyclohexane nmda, 5ht3 and neuronal nicotinic receptor antagonists