HRP990256A2 - The use of aryl-cyclohexylamine derivatives against cns disorders - Google Patents

The use of aryl-cyclohexylamine derivatives against cns disorders Download PDF

Info

Publication number: HRP990256A2
Authority: HR; Croatia
Prior art keywords: phenyl; cyclohexyl; trans; phenol; methyl
Prior art date: 1998-08-18

Application number

HR98115484.2A

Other languages

English (en)

Croatian (hr)

Inventor

Alexander Alanine

Bernd Buettelmann

Marie-Paule Heitz Neidhart

Emmanuel Pinard

Rene Wyler

Original Assignee

Hoffmann La Roche

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.)

1998-08-18

Filing date

1999-08-18

Publication date

2000-04-30

1999-08-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2000-04-30 Publication of HRP990256A2 publication Critical patent/HRP990256A2/hr

Links

150000001875 compounds Chemical class 0.000 claims description 53
-1 nitro, amino Chemical group 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 9
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 8
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 8
230000004770 neurodegeneration Effects 0.000 claims description 8
QPXQQOWQDOGSAY-UHFFFAOYSA-N 4-[4-[methyl(3-phenylpropyl)amino]cyclohexyl]phenol Chemical compound C1CC(C=2C=CC(O)=CC=2)CCC1N(C)CCCC1=CC=CC=C1 QPXQQOWQDOGSAY-UHFFFAOYSA-N 0.000 claims description 5
MMPGKIULWGETNC-AQYVVDRMSA-N CCN(CCCc1ccccc1)[C@H]1CC[C@@H](CC1)c1ccc(O)cc1 Chemical compound CCN(CCCc1ccccc1)[C@H]1CC[C@@H](CC1)c1ccc(O)cc1 MMPGKIULWGETNC-AQYVVDRMSA-N 0.000 claims description 5
HUFQZJXWQQDFFF-KESTWPANSA-N CN(CCOc1ccc(C)cc1)[C@H]1CC[C@@H](CC1)c1ccc(O)cc1 Chemical compound CN(CCOc1ccc(C)cc1)[C@H]1CC[C@@H](CC1)c1ccc(O)cc1 HUFQZJXWQQDFFF-KESTWPANSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
MFZGWTAJGYWBEU-UHFFFAOYSA-N 4-[4-(3-phenylpropylamino)cyclohexyl]phenol Chemical group C1=CC(O)=CC=C1C1CCC(NCCCC=2C=CC=CC=2)CC1 MFZGWTAJGYWBEU-UHFFFAOYSA-N 0.000 claims description 4
JUMWWQUGQVXHOA-LSAOGOSGSA-N OCC(CCc1ccccc1)N[C@H]1CC[C@@H](CC1)c1ccc(O)cc1 Chemical compound OCC(CCc1ccccc1)N[C@H]1CC[C@@H](CC1)c1ccc(O)cc1 JUMWWQUGQVXHOA-LSAOGOSGSA-N 0.000 claims description 4
QPFHWVRUOPTRBQ-UAPYVXQJSA-N Oc1ccc(cc1)[C@H]1OC[C@@H](CO1)NCCCc1ccccc1 Chemical group Oc1ccc(cc1)[C@H]1OC[C@@H](CO1)NCCCc1ccccc1 QPFHWVRUOPTRBQ-UAPYVXQJSA-N 0.000 claims description 4
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
JYGVPBTTWUXNAH-UHFFFAOYSA-N 4-[4-[methyl(3-phenylpropyl)amino]piperidin-1-yl]phenol Chemical compound C1CN(C=2C=CC(O)=CC=2)CCC1N(C)CCCC1=CC=CC=C1 JYGVPBTTWUXNAH-UHFFFAOYSA-N 0.000 claims description 3
SLNWEKVEANGPJW-OIFYPAEGSA-N OCC(CN[C@H]1CC[C@@H](CC1)c1ccc(O)cc1)Cc1ccccc1 Chemical compound OCC(CN[C@H]1CC[C@@H](CC1)c1ccc(O)cc1)Cc1ccccc1 SLNWEKVEANGPJW-OIFYPAEGSA-N 0.000 claims description 3
AGKKZDATHXMERD-XUTJKUGGSA-N Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCCCc1ccccc1 Chemical compound Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCCCc1ccccc1 AGKKZDATHXMERD-XUTJKUGGSA-N 0.000 claims description 3
230000001154 acute effect Effects 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
230000001580 bacterial effect Effects 0.000 claims description 3
230000001684 chronic effect Effects 0.000 claims description 3
NQDJXXFJXQNQPY-UHFFFAOYSA-N 4-[3-methyl-4-[methyl(3-phenylpropyl)amino]cyclohexyl]phenol Chemical compound CC1CC(C=2C=CC(O)=CC=2)CCC1N(C)CCCC1=CC=CC=C1 NQDJXXFJXQNQPY-UHFFFAOYSA-N 0.000 claims description 2
208000024827 Alzheimer disease Diseases 0.000 claims description 2
208000023105 Huntington disease Diseases 0.000 claims description 2
IUZOIYJLQPVIRJ-IRJFHVNHSA-N Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCCc1ccc(F)cc1 Chemical compound Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCCc1ccc(F)cc1 IUZOIYJLQPVIRJ-IRJFHVNHSA-N 0.000 claims description 2
208000018737 Parkinson disease Diseases 0.000 claims description 2
208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
208000034189 Sclerosis Diseases 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
208000015181 infectious disease Diseases 0.000 claims 1
230000009278 visceral effect Effects 0.000 claims 1
238000007429 general method Methods 0.000 description 98
239000007787 solid Substances 0.000 description 60
239000013078 crystal Substances 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
238000000034 method Methods 0.000 description 37
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 36
239000003921 oil Substances 0.000 description 36
235000019198 oils Nutrition 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
238000004587 chromatography analysis Methods 0.000 description 22
239000002904 solvent Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
230000008018 melting Effects 0.000 description 21
238000002844 melting Methods 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
229910052681 coesite Inorganic materials 0.000 description 18
229910052906 cristobalite Inorganic materials 0.000 description 18
239000000377 silicon dioxide Substances 0.000 description 18
235000012239 silicon dioxide Nutrition 0.000 description 18
229910052682 stishovite Inorganic materials 0.000 description 18
229910052905 tridymite Inorganic materials 0.000 description 18
239000012230 colorless oil Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
229940117803 phenethylamine Drugs 0.000 description 10
BEBTXYAQBNBPJY-UHFFFAOYSA-N 2-(4-methoxyphenyl)cyclohexan-1-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)CCCC1 BEBTXYAQBNBPJY-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000007832 Na2SO4 Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000872 buffer Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002178 crystalline material Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
NHGFHASFPCIYQE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(2-phenylethyl)cyclohexan-1-amine Chemical compound C1=CC(OC)=CC=C1C1CC(NCCC=2C=CC=CC=2)CCC1 NHGFHASFPCIYQE-UHFFFAOYSA-N 0.000 description 5
NDTXATIPONZYNP-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(4-phenylbutyl)cyclohexan-1-amine Chemical compound C1=CC(OC)=CC=C1C1CC(NCCCCC=2C=CC=CC=2)CCC1 NDTXATIPONZYNP-UHFFFAOYSA-N 0.000 description 5
WSJCOYPAJXGQGD-UHFFFAOYSA-N 3-methyl-1-(4-phenylmethoxyphenyl)-n-(3-phenylpropyl)piperidin-4-amine Chemical compound CC1CN(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCC1NCCCC1=CC=CC=C1 WSJCOYPAJXGQGD-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
SGSFKVQGZKWXJK-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(3-phenylpropyl)piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1CCC(NCCCC=2C=CC=CC=2)CC1 SGSFKVQGZKWXJK-UHFFFAOYSA-N 0.000 description 4
XMPAGUKYJJNJJE-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)piperidin-4-amine Chemical compound C1CC(N)CCN1C(C=C1)=CC=C1OCC1=CC=CC=C1 XMPAGUKYJJNJJE-UHFFFAOYSA-N 0.000 description 4
MBLQWOPDBGTOOL-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(2-phenylethyl)cyclohexan-1-amine Chemical compound C1=CC(OC)=CC=C1C1C(NCCC=2C=CC=CC=2)CCCC1 MBLQWOPDBGTOOL-UHFFFAOYSA-N 0.000 description 4
NGFJULVMKVJTBD-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(3-phenylpropyl)cyclohex-2-en-1-amine Chemical compound C1=CC(OC)=CC=C1C1=CC(NCCCC=2C=CC=CC=2)CCC1 NGFJULVMKVJTBD-UHFFFAOYSA-N 0.000 description 4
MNZYPWSIMOQVLV-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(3-phenylpropyl)cyclohexan-1-amine Chemical compound C1=CC(OC)=CC=C1C1CC(NCCCC=2C=CC=CC=2)CCC1 MNZYPWSIMOQVLV-UHFFFAOYSA-N 0.000 description 4
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
GMIWLFZQXCZILR-UHFFFAOYSA-N 4-(4-phenylmethoxyphenyl)cyclohexan-1-one Chemical compound C1CC(=O)CCC1C(C=C1)=CC=C1OCC1=CC=CC=C1 GMIWLFZQXCZILR-UHFFFAOYSA-N 0.000 description 4
UVTDXOFGONOVCR-UHFFFAOYSA-N 4-[3-(2-phenylethylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CC(NCCC=2C=CC=CC=2)CCC1 UVTDXOFGONOVCR-UHFFFAOYSA-N 0.000 description 4
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 4
AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 4
229910010084 LiAlH4 Inorganic materials 0.000 description 4
XBKIWSGYCVHXHU-RXMMZNSPSA-N N([C@@H]1CC[C@H](CC1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C(C)CCC1=CC=CC=C1 Chemical compound N([C@@H]1CC[C@H](CC1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C(C)CCC1=CC=CC=C1 XBKIWSGYCVHXHU-RXMMZNSPSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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239000003054 catalyst Substances 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
CAAJNRHCJHQMCJ-UHFFFAOYSA-N n-[1-(4-methoxyphenyl)piperidin-4-yl]-3-phenylpropanamide Chemical compound C1=CC(OC)=CC=C1N1CCC(NC(=O)CCC=2C=CC=CC=2)CC1 CAAJNRHCJHQMCJ-UHFFFAOYSA-N 0.000 description 4
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
YEDABTMVGPSROH-VZCXRCSSSA-N (nz)-n-[3,3-dimethyl-1-(4-phenylmethoxyphenyl)piperidin-4-ylidene]hydroxylamine Chemical compound C1C\C(=N\O)C(C)(C)CN1C(C=C1)=CC=C1OCC1=CC=CC=C1 YEDABTMVGPSROH-VZCXRCSSSA-N 0.000 description 3
YQBSXEDOWCRFMQ-VXPUYCOJSA-N (nz)-n-[3-methyl-1-(4-phenylmethoxyphenyl)piperidin-4-ylidene]hydroxylamine Chemical compound C1C\C(=N\O)C(C)CN1C(C=C1)=CC=C1OCC1=CC=CC=C1 YQBSXEDOWCRFMQ-VXPUYCOJSA-N 0.000 description 3
CFURUOIWOWOEND-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-methyl-n-(3-phenylpropyl)piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1CCC(N(C)CCCC=2C=CC=CC=2)CC1 CFURUOIWOWOEND-UHFFFAOYSA-N 0.000 description 3
LLQPZJOXQGVEEQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1CCC(N)CC1 LLQPZJOXQGVEEQ-UHFFFAOYSA-N 0.000 description 3
KACQSVYTBQDRGP-UHFFFAOYSA-N 2-(3-methoxyphenyl)cyclohexan-1-one Chemical compound COC1=CC=CC(C2C(CCCC2)=O)=C1 KACQSVYTBQDRGP-UHFFFAOYSA-N 0.000 description 3
DGTJSRADXAFSLG-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(3-phenylbutyl)cyclohexan-1-amine Chemical compound C1=CC(OC)=CC=C1C1C(NCCC(C)C=2C=CC=CC=2)CCCC1 DGTJSRADXAFSLG-UHFFFAOYSA-N 0.000 description 3
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 3
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 3
GNBRDUCVQNFJFK-UHFFFAOYSA-N 2-methyl-4-(4-phenylmethoxyphenyl)-n-(3-phenylpropyl)cyclohexan-1-amine Chemical compound CC1CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCC1NCCCC1=CC=CC=C1 GNBRDUCVQNFJFK-UHFFFAOYSA-N 0.000 description 3
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BFRMOQFXHSSGLB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(4-phenylbutyl)cyclohex-2-en-1-amine Chemical compound C1=CC(OC)=CC=C1C1=CC(NCCCCC=2C=CC=CC=2)CCC1 BFRMOQFXHSSGLB-UHFFFAOYSA-N 0.000 description 3
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OUCGTTVBUYSJDJ-UHFFFAOYSA-N 3-methyl-1-(4-phenylmethoxyphenyl)piperidin-4-one Chemical compound C1CC(=O)C(C)CN1C(C=C1)=CC=C1OCC1=CC=CC=C1 OUCGTTVBUYSJDJ-UHFFFAOYSA-N 0.000 description 3
CCHKOVOXVCKVHF-UHFFFAOYSA-N 4-(3-phenylpropylamino)cyclohexan-1-one Chemical compound C1CC(=O)CCC1NCCCC1=CC=CC=C1 CCHKOVOXVCKVHF-UHFFFAOYSA-N 0.000 description 3
PKZGPCXLJQQSSZ-UHFFFAOYSA-N 4-[2-(4-phenylbutylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1C(NCCCCC=2C=CC=CC=2)CCCC1 PKZGPCXLJQQSSZ-UHFFFAOYSA-N 0.000 description 3
WWLZMWYCSMQWGL-UHFFFAOYSA-N 4-[3-methyl-4-(3-phenylpropylamino)piperidin-1-yl]phenol Chemical compound CC1CN(C=2C=CC(O)=CC=2)CCC1NCCCC1=CC=CC=C1 WWLZMWYCSMQWGL-UHFFFAOYSA-N 0.000 description 3
ZWCKJNFUDJGZAD-UHFFFAOYSA-N 4-[4-(3-phenylpropylamino)piperidin-1-yl]phenol Chemical compound C1=CC(O)=CC=C1N1CCC(NCCCC=2C=CC=CC=2)CC1 ZWCKJNFUDJGZAD-UHFFFAOYSA-N 0.000 description 3
AGKKZDATHXMERD-UHFFFAOYSA-N 4-[4-(4-phenylbutylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CCC(NCCCCC=2C=CC=CC=2)CC1 AGKKZDATHXMERD-UHFFFAOYSA-N 0.000 description 3
JIZDOLOJXKUURO-UHFFFAOYSA-N 4-[4-(4-phenylbutylamino)piperidin-1-yl]phenol Chemical compound C1=CC(O)=CC=C1N1CCC(NCCCCC=2C=CC=CC=2)CC1 JIZDOLOJXKUURO-UHFFFAOYSA-N 0.000 description 3
SNWXKZZABLIQTH-UHFFFAOYSA-N 4-hydroxy-4-(4-phenylmethoxyphenyl)cyclohexan-1-one Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C1(O)CCC(=O)CC1 SNWXKZZABLIQTH-UHFFFAOYSA-N 0.000 description 3
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Classifications

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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
- 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
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- A—HUMAN NECESSITIES
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- 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
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- 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
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
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Landscapes

Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Emergency Medicine (AREA)
Psychology (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (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)
Hydrogenated Pyridines (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

HR98115484.2A 1998-08-18 1999-08-18 The use of aryl-cyclohexylamine derivatives against cns disorders HRP990256A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98115484		1998-08-18

Publications (1)

Publication Number	Publication Date
HRP990256A2 true HRP990256A2 (en)	2000-04-30

Family

ID=8232474

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR98115484.2A HRP990256A2 (en)	1998-08-18	1999-08-18	The use of aryl-cyclohexylamine derivatives against cns disorders

Country Status (24)

Country	Link
US (1)	US6184236B1 (de)
JP (1)	JP3455142B2 (de)
KR (1)	KR100341194B1 (de)
CN (1)	CN1141936C (de)
AR (1)	AR021770A1 (de)
AT (1)	ATE326219T1 (de)
AU (1)	AU756408B2 (de)
BR (1)	BR9903779A (de)
CA (1)	CA2280455A1 (de)
DE (1)	DE69931316D1 (de)
HR (1)	HRP990256A2 (de)
HU (1)	HUP9902737A3 (de)
ID (1)	ID23107A (de)
IL (1)	IL131399A0 (de)
MA (1)	MA26677A1 (de)
MY (1)	MY133133A (de)
NO (1)	NO993948L (de)
NZ (1)	NZ337243A (de)
PE (1)	PE20000955A1 (de)
PL (1)	PL334949A1 (de)
SG (1)	SG82014A1 (de)
TR (1)	TR199902015A3 (de)
YU (1)	YU38699A (de)
ZA (1)	ZA995212B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2001263130A1 (en) *	2000-06-06	2001-12-17	Warner Lambert Company	Bicyclic cyclohexylamines and their use as nmda receptor antagonists
US7375136B2 (en) *	2001-03-08	2008-05-20	Emory University	pH-dependent NMDA receptor antagonists
DE10153345A1 (de) *	2001-10-29	2003-05-08	Gruenenthal Gmbh	Substituierte 1H-Chinoxalin-2-on-Verbindungen und substituierte 4-Aryl- und 4-Heteroarylcyclohexan-Verbindungen
US20070004805A1 (en) *	2005-07-01	2007-01-04	Navinta Llc	Process for preparation of liquid dosage form containing sodium 4-phenylbutyrate
EA201070077A1 (ru) *	2007-06-29	2010-08-30	Эмори Юниверсити	Антагонисты nmda-рецепторов с нейропротективным действием

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4032766A1 (de)	1990-10-16	1992-04-30	Basf Ag	Phenylpiperidinoylamine und diese enthaltende arzneimittel
DE4117904A1 (de)	1991-05-31	1992-12-03	Basf Ag	Substituierte n-phenylpiperidine
ATE130851T1 (de)	1991-03-14	1995-12-15	Basf Ag	Substituierte n-phenylpiperidine und arzneimittel daraus.
WO1997015549A1 (en)	1995-10-26	1997-05-01	Tokyo Tanabe Company Limited	PHENYLETHANOLAMINE COMPOUNDS USEFUL AS β3 AGONIST, PROCESS FOR PRODUCING THE SAME, AND INTERMEDIATES IN THE PRODUCTION OF THE SAME

1999
- 1999-08-09 DE DE69931316T patent/DE69931316D1/de not_active Expired - Lifetime
- 1999-08-09 AT AT99115114T patent/ATE326219T1/de not_active IP Right Cessation
- 1999-08-09 US US09/370,602 patent/US6184236B1/en not_active Expired - Fee Related
- 1999-08-13 AR ARP990104079A patent/AR021770A1/es not_active Application Discontinuation
- 1999-08-13 IL IL13139999A patent/IL131399A0/xx unknown
- 1999-08-13 NZ NZ337243A patent/NZ337243A/xx unknown
- 1999-08-13 CA CA002280455A patent/CA2280455A1/en not_active Abandoned
- 1999-08-13 PE PE1999000826A patent/PE20000955A1/es not_active Application Discontinuation
- 1999-08-16 SG SG9903973A patent/SG82014A1/en unknown
- 1999-08-16 ID IDP990791A patent/ID23107A/id unknown
- 1999-08-16 HU HU9902737A patent/HUP9902737A3/hu unknown
- 1999-08-16 JP JP22965899A patent/JP3455142B2/ja not_active Expired - Fee Related
- 1999-08-16 YU YU38699A patent/YU38699A/sh unknown
- 1999-08-16 MY MYPI99003508A patent/MY133133A/en unknown
- 1999-08-16 ZA ZA9905212A patent/ZA995212B/xx unknown
- 1999-08-17 AU AU44537/99A patent/AU756408B2/en not_active Ceased
- 1999-08-17 MA MA25736A patent/MA26677A1/fr unknown
- 1999-08-17 CN CNB991179110A patent/CN1141936C/zh not_active Expired - Fee Related
- 1999-08-17 BR BR9903779-3A patent/BR9903779A/pt not_active IP Right Cessation
- 1999-08-17 KR KR1019990033814A patent/KR100341194B1/ko not_active Expired - Fee Related
- 1999-08-17 NO NO993948A patent/NO993948L/no unknown
- 1999-08-17 PL PL99334949A patent/PL334949A1/xx not_active Application Discontinuation
- 1999-08-18 HR HR98115484.2A patent/HRP990256A2/hr not_active Application Discontinuation
- 1999-08-18 TR TR1999/02015A patent/TR199902015A3/tr unknown

Also Published As

Publication number	Publication date
KR20000017343A (ko)	2000-03-25
PL334949A1 (en)	2000-02-28
PE20000955A1 (es)	2000-09-28
TR199902015A2 (xx)	2000-03-21
CA2280455A1 (en)	2000-02-18
ATE326219T1 (de)	2006-06-15
BR9903779A (pt)	2000-09-19
AU4453799A (en)	2000-05-04
KR100341194B1 (ko)	2002-06-20
TR199902015A3 (tr)	2000-03-21
DE69931316D1 (de)	2006-06-22
JP3455142B2 (ja)	2003-10-14
CN1248439A (zh)	2000-03-29
AU756408B2 (en)	2003-01-09
US6184236B1 (en)	2001-02-06
NO993948L (no)	2000-02-21
HUP9902737A3 (en)	2001-01-29
JP2000109429A (ja)	2000-04-18
HU9902737D0 (en)	1999-10-28
ID23107A (id)	2000-02-24
ZA995212B (en)	2000-02-18
MY133133A (en)	2007-10-31
NZ337243A (en)	2000-12-22
NO993948D0 (no)	1999-08-17
IL131399A0 (en)	2001-01-28
SG82014A1 (en)	2001-07-24
CN1141936C (zh)	2004-03-17
MA26677A1 (fr)	2004-12-20
YU38699A (sh)	2002-03-18
AR021770A1 (es)	2002-08-07
HUP9902737A2 (hu)	2000-06-28

Legal Events

Date	Code	Title
2000-04-30	A1OB	Publication of a patent application
2000-10-06	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2007-08-30	ODBI	Application refused

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EP0031910B1 (de)	1983-04-13	Anilinderivate, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung
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