NO309924B1 - Anvendelse av fenalkylaminer og nye fenylalkylaminer - Google Patents

Anvendelse av fenalkylaminer og nye fenylalkylaminer Download PDF

Info

Publication number: NO309924B1
Authority: NO; Norway
Prior art keywords: phenyl; methyl; allyl; amino; bromo
Prior art date: 1993-07-14

Application number

NO942606A

Other languages

English (en)

Norwegian (no)

Other versions

NO942606D0 (no

NO942606L (no

Inventor

Johannes Aebi

Philippe Guerry

Synese Jolidon

Oliver Morand

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.)

1993-07-14

Filing date

1994-07-12

Publication date

2001-04-23

1994-07-12 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1994-07-12 Publication of NO942606D0 publication Critical patent/NO942606D0/no

1995-01-16 Publication of NO942606L publication Critical patent/NO942606L/no

2001-04-23 Publication of NO309924B1 publication Critical patent/NO309924B1/no

Links

150000001875 compounds Chemical class 0.000 claims abstract description 33
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 14
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical class 0.000 claims abstract description 13
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 9
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 14
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
-1 2,6-dimethyl-5-heptyl Chemical group 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 10
239000012965 benzophenone Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
RNTIMLQORXMWOI-UHFFFAOYSA-N (4-bromophenyl)-[4-[6-[methyl(prop-2-enyl)amino]hexoxy]phenyl]methanone Chemical compound C1=CC(OCCCCCCN(C)CC=C)=CC=C1C(=O)C1=CC=C(Br)C=C1 RNTIMLQORXMWOI-UHFFFAOYSA-N 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
CMYCCJYVZIMDFU-UHFFFAOYSA-N Ro 48-8071 Chemical compound FC1=CC(OCCCCCCN(C)CC=C)=CC=C1C(=O)C1=CC=C(Br)C=C1 CMYCCJYVZIMDFU-UHFFFAOYSA-N 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
OHZDMBQUJHJOTJ-SNAWJCMRSA-N (4-bromophenyl)-[4-[(e)-4-[ethyl(methyl)amino]but-2-enoxy]phenyl]methanone Chemical compound C1=CC(OC/C=C/CN(C)CC)=CC=C1C(=O)C1=CC=C(Br)C=C1 OHZDMBQUJHJOTJ-SNAWJCMRSA-N 0.000 claims description 2
PHWCMMNCJNFLCS-UHFFFAOYSA-N 1,7-bis[4-[4-[(dimethylamino)methyl]phenyl]phenyl]heptan-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(C=C1)=CC=C1CCCC(=O)CCCC1=CC=C(C=2C=CC(CN(C)C)=CC=2)C=C1 PHWCMMNCJNFLCS-UHFFFAOYSA-N 0.000 claims description 2
YXJBCOJMFLUVLM-UHFFFAOYSA-N [3-chloro-4-[4-(dimethylamino)but-2-enoxy]phenyl]-phenylmethanone Chemical compound C1=C(Cl)C(OCC=CCN(C)C)=CC=C1C(=O)C1=CC=CC=C1 YXJBCOJMFLUVLM-UHFFFAOYSA-N 0.000 claims description 2
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 2
NVYFMEJWCVZVKH-UHFFFAOYSA-N bis[3-(3,4-dichlorophenyl)-4-[4-[(dimethylamino)methyl]phenyl]phenyl]methanone Chemical compound ClC=1C=C(C=CC=1Cl)C1=C(C=CC(=C1)C(=O)C1=CC(=C(C=C1)C1=CC=C(C=C1)CN(C)C)C1=CC(=C(C=C1)Cl)Cl)C1=CC=C(C=C1)CN(C)C NVYFMEJWCVZVKH-UHFFFAOYSA-N 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
LJVHJHLTRBXGMH-HNQUOIGGSA-N (e)-1,4-dibromobut-1-ene Chemical compound BrCC\C=C\Br LJVHJHLTRBXGMH-HNQUOIGGSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229940024874 benzophenone Drugs 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000007903 gelatin capsule Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000013543 active substance Substances 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
BNOUBIJDOMWKPY-UHFFFAOYSA-N (4-bromophenyl)-(2-fluoro-4-hydroxyphenyl)methanone Chemical compound FC1=CC(O)=CC=C1C(=O)C1=CC=C(Br)C=C1 BNOUBIJDOMWKPY-UHFFFAOYSA-N 0.000 description 3
HRQGKJVRJYEBPA-UHFFFAOYSA-N (4-bromophenyl)-(3-fluoro-4-hydroxyphenyl)methanone Chemical compound C1=C(F)C(O)=CC=C1C(=O)C1=CC=C(Br)C=C1 HRQGKJVRJYEBPA-UHFFFAOYSA-N 0.000 description 3
GCSYLFJQFPSOBR-UHFFFAOYSA-N (4-bromophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(Br)C=C1 GCSYLFJQFPSOBR-UHFFFAOYSA-N 0.000 description 3
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
239000007818 Grignard reagent Substances 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
IYPKEFFZXIOKJL-UHFFFAOYSA-N [3-bromo-4-(4-bromobut-2-enoxy)phenyl]-(4-bromophenyl)methanone Chemical compound C1=C(Br)C(OCC=CCBr)=CC=C1C(=O)C1=CC=C(Br)C=C1 IYPKEFFZXIOKJL-UHFFFAOYSA-N 0.000 description 3
SYFFUZGMEFPESB-UHFFFAOYSA-N [4-(6-bromohexoxy)-3-chlorophenyl]-(4-bromophenyl)methanone Chemical compound C1=C(OCCCCCCBr)C(Cl)=CC(C(=O)C=2C=CC(Br)=CC=2)=C1 SYFFUZGMEFPESB-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
150000004795 grignard reagents Chemical class 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000052 vinegar Substances 0.000 description 3
235000021419 vinegar Nutrition 0.000 description 3
UMMBAAGFWRINMM-UHFFFAOYSA-N (2,6-difluorophenyl)-(3-fluoro-4-hydroxyphenyl)methanone Chemical compound C1=C(F)C(O)=CC=C1C(=O)C1=C(F)C=CC=C1F UMMBAAGFWRINMM-UHFFFAOYSA-N 0.000 description 2
AQUALGKCHBFFCK-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-(4-methylphenyl)phenyl]methanone Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(=O)C=2C=C(Cl)C(Cl)=CC=2)C=C1 AQUALGKCHBFFCK-UHFFFAOYSA-N 0.000 description 2
ZKIHKABXBPHQCE-UHFFFAOYSA-N (3-bromo-4-hydroxyphenyl)-(4-bromophenyl)methanone Chemical compound C1=C(Br)C(O)=CC=C1C(=O)C1=CC=C(Br)C=C1 ZKIHKABXBPHQCE-UHFFFAOYSA-N 0.000 description 2
FUUHDAKJQKNBEF-UHFFFAOYSA-N (3-chloro-4-hydroxyphenyl)-phenylmethanone Chemical compound C1=C(Cl)C(O)=CC=C1C(=O)C1=CC=CC=C1 FUUHDAKJQKNBEF-UHFFFAOYSA-N 0.000 description 2
VFLIJYQKWRGEKI-UHFFFAOYSA-N (4-bromophenyl)-[3-chloro-4-[6-(dimethylamino)hexoxy]phenyl]methanone Chemical compound C1=C(Cl)C(OCCCCCCN(C)C)=CC=C1C(=O)C1=CC=C(Br)C=C1 VFLIJYQKWRGEKI-UHFFFAOYSA-N 0.000 description 2
IEXMDLWVLFRZDB-UHFFFAOYSA-N 1-(3-fluoro-4-hydroxyphenyl)-6-methylhept-5-en-2-one Chemical compound CC(C)=CCCC(=O)CC1=CC=C(O)C(F)=C1 IEXMDLWVLFRZDB-UHFFFAOYSA-N 0.000 description 2
ZRCSJVMJTNVKKZ-UHFFFAOYSA-N 1-(3-fluoro-4-methoxyphenyl)-5-methylhexan-1-one Chemical compound COC1=CC=C(C(=O)CCCC(C)C)C=C1F ZRCSJVMJTNVKKZ-UHFFFAOYSA-N 0.000 description 2
KJDIRVZPWWVSDH-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(3-fluoro-4-hydroxyphenyl)ethanone Chemical compound C1=C(F)C(O)=CC=C1CC(=O)C1=CC=C(Br)C=C1 KJDIRVZPWWVSDH-UHFFFAOYSA-N 0.000 description 2
ZVDWVVMNDONXPR-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-hydroxyphenyl)ethanone Chemical compound C1=CC(O)=CC=C1CC(=O)C1=CC=C(Br)C=C1 ZVDWVVMNDONXPR-UHFFFAOYSA-N 0.000 description 2
KJZTZIQNEYTQSN-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-5-methylhex-4-en-1-one Chemical compound CC(C)=CCCC(=O)C1=CC=C(O)C=C1 KJZTZIQNEYTQSN-UHFFFAOYSA-N 0.000 description 2
RWBMJSWTNLBNLN-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-5-methylhexan-1-one Chemical compound CC(C)CCCC(=O)C1=CC=C(O)C=C1 RWBMJSWTNLBNLN-UHFFFAOYSA-N 0.000 description 2
XLZVHOFYSQGUQA-UHFFFAOYSA-N 1-[2-(4-bromophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(Br)C=C1 XLZVHOFYSQGUQA-UHFFFAOYSA-N 0.000 description 2
WAEKCHUPDOGQJY-UHFFFAOYSA-N 1-chloro-3-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=CC(Cl)=C1 WAEKCHUPDOGQJY-UHFFFAOYSA-N 0.000 description 2
YDKOXGXRYCTKLM-UHFFFAOYSA-N 2-(3-fluoro-4-trimethylsilyloxyphenyl)-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CC1=CC=C(O[Si](C)(C)C)C(F)=C1 YDKOXGXRYCTKLM-UHFFFAOYSA-N 0.000 description 2
ZTWGIBUESKWKHQ-UHFFFAOYSA-N 2-chloro-4-(4-methylphenyl)benzaldehyde Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=O)C(Cl)=C1 ZTWGIBUESKWKHQ-UHFFFAOYSA-N 0.000 description 2
PCQMBPJCAHOPOF-UHFFFAOYSA-N 4-(3-fluoro-4-hydroxybenzoyl)benzonitrile Chemical compound C1=C(F)C(O)=CC=C1C(=O)C1=CC=C(C#N)C=C1 PCQMBPJCAHOPOF-UHFFFAOYSA-N 0.000 description 2
ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 2
DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
HLDHFOCXVJJMBT-UHFFFAOYSA-N 5-methylhexanoyl chloride Chemical compound CC(C)CCCC(Cl)=O HLDHFOCXVJJMBT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 2
229940127328 Cholesterol Synthesis Inhibitors Drugs 0.000 description 2
208000035150 Hypercholesterolemia Diseases 0.000 description 2
102000000853 LDL receptors Human genes 0.000 description 2
108010001831 LDL receptors Proteins 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
FLAJEHZOIBLCHA-UHFFFAOYSA-N [4-[4-(bromomethyl)phenyl]phenyl]-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1=CC=C(C=2C=CC(CBr)=CC=2)C=C1 FLAJEHZOIBLCHA-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
208000011775 arteriosclerosis disease Diseases 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000008298 dragée Substances 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
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235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000003827 upregulation Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000012178 vegetable wax Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
- 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
- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Emergency Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO942606A 1993-07-14 1994-07-12 Anvendelse av fenalkylaminer og nye fenylalkylaminer NO309924B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH210793		1993-07-14
CH132094		1994-04-28

Publications (3)

Publication Number	Publication Date
NO942606D0 NO942606D0 (no)	1994-07-12
NO942606L NO942606L (no)	1995-01-16
NO309924B1 true NO309924B1 (no)	2001-04-23

Family

ID=25687322

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO942606A NO309924B1 (no)	1993-07-14	1994-07-12	Anvendelse av fenalkylaminer og nye fenylalkylaminer

Country Status (22)

Country	Link
US (3)	US5495048A (da)
EP (1)	EP0636367B1 (da)
JP (1)	JP2519022B2 (da)
KR (1)	KR100312441B1 (da)
CN (1)	CN1087934C (da)
AT (1)	ATE191142T1 (da)
AU (1)	AU684507B2 (da)
CA (1)	CA2126518C (da)
CZ (1)	CZ288518B6 (da)
DE (1)	DE59409248D1 (da)
DK (1)	DK0636367T3 (da)
ES (1)	ES2144471T3 (da)
GR (1)	GR3033645T3 (da)
HU (1)	HUT70835A (da)
IL (1)	IL110254A (da)
NO (1)	NO309924B1 (da)
NZ (1)	NZ260968A (da)
PH (1)	PH31092A (da)
PT (1)	PT636367E (da)
RU (1)	RU2141942C1 (da)
TW (1)	TW438774B (da)
UA (1)	UA37199C2 (da)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2190699A1 (en)	1995-12-08	1997-06-09	Johannes Aebi	Tertiary amines
CA2190708A1 (en) *	1995-12-08	1997-06-09	Johannes Aebi	Aminoalkyl substituted benzo-heterocyclic compounds
AU2001289642B2 (en) *	2000-07-18	2005-01-13	F. Hoffmann-La Roche Ag	Aniline derivatives
HRP20030086A2 (en)	2000-08-16	2005-02-28	F. Hoffmann - La Roche Ag	Novel aminocyclohexane derivatives
US6964974B2 (en)	2000-09-08	2005-11-15	Hoffmann-La Roche Inc.	2,3-oxidosqualene-lanosterol cyclase inhibitors
US6503907B2 (en) *	2000-11-28	2003-01-07	Hoffmann-La Roche Inc.	Indole and dihydroindole derivatives
US6706751B2 (en)	2000-12-21	2004-03-16	Hoffman-La Roche Inc.	Dihydroindole and tetrahydroquinoline derivatives
AU2002358096B2 (en) *	2001-12-12	2006-05-11	F. Hoffmann-La Roche Ag	Substituted cyclohexane derivatives
US7012077B2 (en) *	2001-12-20	2006-03-14	Hoffmann-La Roche Inc.	Substituted cyclohexane derivatives
US6727277B1 (en)	2002-11-12	2004-04-27	Kansas State University Research Foundation	Compounds affecting cholesterol absorption
TW200524849A (en) *	2003-07-02	2005-08-01	Hoffmann La Roche	Hydroxyalkylamide derivatives
KR100806603B1 (ko) *	2003-09-22	2008-02-29	에프. 호프만-라 로슈 아게	아미노알킬아미드 치환된 사이클로헥실 유도체
CN101583593A (zh) *	2006-11-13	2009-11-18	辉瑞产品公司	二芳基、二吡啶基和芳基-吡啶基衍生物及其用途
CN108530390B (zh) *	2017-03-06	2020-04-21	西南化工研究设计院有限公司	一种4-羟基二苯甲酮的烷基化方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3647863A (en) *	1968-11-25	1972-03-07	Richardson Merrell Inc	Aminoalkoxy-triphenyl ethylenes and the salts thereof
US3928449A (en) *	1969-04-03	1975-12-23	Sandoz Ag	Aminoalkoxy-terphenyls and the salts thereof
CA2016738A1 (en) *	1989-06-08	1990-12-08	Philippe Guerry	Substituted aminoalkylbenzene derivatives
US5214046A (en) *	1989-07-27	1993-05-25	Hoffmann-La Roche Inc.	Substituted aminoalkoxybenzene anti-fungicidal compositions and use
CA2020888A1 (en) *	1989-07-27	1991-01-28	Philippe Guerry	Substituted aminoalkoxybenzene derivatives
US5239084A (en) *	1990-06-29	1993-08-24	Hoffmann-La Roche Inc.	Substituted aminoalkyl biphenyl compounds
CA2044533A1 (en) *	1990-06-29	1991-12-30	Philippe Guerry	Substituted aminoalkylbiphenyl derivatives

1994
- 1994-06-16 TW TW083105454A patent/TW438774B/zh not_active IP Right Cessation
- 1994-06-17 US US08/261,615 patent/US5495048A/en not_active Expired - Fee Related
- 1994-06-22 CA CA002126518A patent/CA2126518C/en not_active Expired - Fee Related
- 1994-07-01 EP EP94110246A patent/EP0636367B1/de not_active Expired - Lifetime
- 1994-07-01 DK DK94110246T patent/DK0636367T3/da active
- 1994-07-01 DE DE59409248T patent/DE59409248D1/de not_active Expired - Fee Related
- 1994-07-01 ES ES94110246T patent/ES2144471T3/es not_active Expired - Lifetime
- 1994-07-01 PT PT94110246T patent/PT636367E/pt unknown
- 1994-07-01 AT AT94110246T patent/ATE191142T1/de not_active IP Right Cessation
- 1994-07-08 JP JP6157038A patent/JP2519022B2/ja not_active Expired - Fee Related
- 1994-07-08 AU AU67358/94A patent/AU684507B2/en not_active Ceased
- 1994-07-08 NZ NZ260968A patent/NZ260968A/en unknown
- 1994-07-08 RU RU94026094/04A patent/RU2141942C1/ru not_active IP Right Cessation
- 1994-07-08 IL IL110254A patent/IL110254A/en not_active IP Right Cessation
- 1994-07-12 PH PH48609A patent/PH31092A/en unknown
- 1994-07-12 CZ CZ19941676A patent/CZ288518B6/cs not_active IP Right Cessation
- 1994-07-12 NO NO942606A patent/NO309924B1/no unknown
- 1994-07-13 CN CN94108447A patent/CN1087934C/zh not_active Expired - Fee Related
- 1994-07-13 UA UA94075630A patent/UA37199C2/uk unknown
- 1994-07-13 HU HU9402085A patent/HUT70835A/hu unknown
- 1994-07-13 KR KR1019940016823A patent/KR100312441B1/ko not_active Expired - Fee Related
1995
- 1995-06-06 US US08/468,114 patent/US5574071A/en not_active Expired - Fee Related
- 1995-11-08 US US08/555,054 patent/US5637771A/en not_active Expired - Fee Related
2000
- 2000-06-12 GR GR20000401332T patent/GR3033645T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
US5574071A (en)	1996-11-12
EP0636367A1 (de)	1995-02-01
JPH0753479A (ja)	1995-02-28
TW438774B (en)	2001-06-07
JP2519022B2 (ja)	1996-07-31
DE59409248D1 (de)	2000-05-04
DK0636367T3 (da)	2000-07-31
PH31092A (en)	1998-02-05
RU94026094A (ru)	1996-05-20
HU9402085D0 (en)	1994-09-28
KR960014096A (ko)	1996-05-22
KR100312441B1 (ko)	2002-10-31
CN1087934C (zh)	2002-07-24
GR3033645T3 (en)	2000-10-31
RU2141942C1 (ru)	1999-11-27
CZ167694A3 (en)	1995-01-18
ES2144471T3 (es)	2000-06-16
IL110254A (en)	1998-04-05
AU684507B2 (en)	1997-12-18
ATE191142T1 (de)	2000-04-15
NO942606D0 (no)	1994-07-12
EP0636367B1 (de)	2000-03-29
PT636367E (pt)	2000-07-31
CA2126518C (en)	2006-11-21
CA2126518A1 (en)	1995-01-15
HUT70835A (en)	1995-11-28
NO942606L (no)	1995-01-16
UA37199C2 (uk)	2001-05-15
US5495048A (en)	1996-02-27
CN1103781A (zh)	1995-06-21
NZ260968A (en)	1996-06-25
IL110254A0 (en)	1994-10-21
AU6735894A (en)	1995-01-27
US5637771A (en)	1997-06-10
CZ288518B6 (cs)	2001-07-11

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JP7836260B2 (ja)	2026-03-26	新規な甲状腺ホルモン模倣物
RU2532545C2 (ru)	2014-11-10	Замещенные производные 4-аминоциклогексана
US7569601B2 (en)	2009-08-04	Cycloalkylidene compounds as modulators of estrogen receptor
HU214875B (hu)	1998-07-28	Eljárás lipidszintcsökkentő oxamidsavszármazékok és hatóanyagként ilyen vegyületeket tartalmazó gyógyszerkészítmények előállítására
KR100312441B1 (ko)	2002-10-31	펜알킬아민 및 이를 포함하는 콜레스테롤 저하제
JPH02180855A (ja)	1990-07-13	リシルオキシダーゼの阻害剤
MXPA06003839A (es)	2006-07-03	Compuestos que comprenden una fraccion de oxido nitrico para inducir la expresion de apoa1 para el tratamiento de desordenes cardiovasculares.
US20210053917A1 (en)	2021-02-25	Novel thyromimetics
JPH07267908A (ja)	1995-10-17	興奮性アミノ酸受容体拮抗剤
US4540690A (en)	1985-09-10	2-(Phenylmethylene)cycloalkylamines and -azetidines
US5494934A (en)	1996-02-27	Guanidine compounds
CZ181891A3 (en)	1994-01-19	Hexahydroazepine derivatives
US5006563A (en)	1991-04-09	Alkylamino- and alkylamino alkyl diarylketones
CN110372571B (zh)	2022-11-15	一种2-(2,2-二芳基乙基)-环胺衍生物或盐及合成和应用与组合物
EP0589039A1 (en)	1994-03-30	Triphenylethylene derivative and pharmaceutical preparation containing the same
CZ305140B6 (cs)	2015-05-20	Cyklohexyl(alkyl)propanolaminy, způsob jejich přípravy a farmaceutické prostředky, které je obsahují
JPS58159444A (ja)	1983-09-21	２−（フエニルメチレン）シクロアルキルアミン類および−アゼチジン類
US5300527A (en)	1994-04-05	Alkylamino-and alkylamino alkyl diarylketones
EA048616B1 (ru)	2024-12-18	Новые тиромиметики
PL176197B1 (pl)	1999-04-30	Nowe fenyloalkiloaminy oraz środek leczniczy obniżający poziom cholesterolu
US20050054641A1 (en)	2005-03-10	Propanolaminomethyltetralines, their preparation and pharmaceutical composition comprising same
JPH04208255A (ja)	1992-07-29	アルキルアミノ−およびアルキルアミノアルキルジアリールケトンおよびその製造方法
JPH0667882B2 (ja)	1994-08-31	フェニルカルボン酸誘導体