SK284328B6 - Dimetyl-(3-aryl-but-3-enyl)-aminozlúčeniny, spôsob ich výroby a ich použitie na výrobu liečiv - Google Patents
Dimetyl-(3-aryl-but-3-enyl)-aminozlúčeniny, spôsob ich výroby a ich použitie na výrobu liečiv Download PDFInfo
- Publication number
- SK284328B6 SK284328B6 SK321-97A SK32197A SK284328B6 SK 284328 B6 SK284328 B6 SK 284328B6 SK 32197 A SK32197 A SK 32197A SK 284328 B6 SK284328 B6 SK 284328B6
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- carbon atoms
- alkyl
- hydrogen atom
- hydrogen
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- -1 (C 1 -C 4) O-alkyl Chemical group 0.000 claims description 14
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 208000002193 Pain Diseases 0.000 claims description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 239000002585 base Substances 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 34
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- PIARDTFGLNPXMD-PSUINESXSA-N (z)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=C/C)\C(C)CN(C)C)=C1 PIARDTFGLNPXMD-PSUINESXSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 17
- 235000019253 formic acid Nutrition 0.000 description 17
- 239000005051 trimethylchlorosilane Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- 150000003840 hydrochlorides Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 5
- IWJTXTSZGVMTQC-UHFFFAOYSA-N 3-[5-(dimethylamino)-2,4-dimethylpent-2-en-3-yl]phenol;hydrochloride Chemical compound Cl.CN(C)CC(C)C(=C(C)C)C1=CC=CC(O)=C1 IWJTXTSZGVMTQC-UHFFFAOYSA-N 0.000 description 5
- FZPDGVOXZFKFHI-MFGIPTIESA-N 4-[(z)-5-(dimethylamino)-4-methylpent-2-en-3-yl]phenol;hydrochloride Chemical compound Cl.CN(C)CC(C)/C(=C/C)C1=CC=C(O)C=C1 FZPDGVOXZFKFHI-MFGIPTIESA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 238000004296 chiral HPLC Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CLGROUXNVAYTBM-OHGISNTKSA-N (e)-3-(3-methoxyphenyl)-n,n,2-trimethylhex-3-en-1-amine;hydrochloride Chemical compound Cl.CN(C)CC(C)\C(=C/CC)C1=CC=CC(OC)=C1 CLGROUXNVAYTBM-OHGISNTKSA-N 0.000 description 4
- PEUBDHMCKFQJKD-UHFFFAOYSA-N 1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylhexan-3-ol Chemical compound CN(C)CC(C)C(O)(CCC)C1=CC=CC(OC)=C1 PEUBDHMCKFQJKD-UHFFFAOYSA-N 0.000 description 4
- TZOOYBCJSXMJPM-MFGIPTIESA-N 3-[(Z)-5-(dimethylamino)-4-methylpent-2-en-3-yl]phenol hydrochloride Chemical compound Cl.CN(C)CC(C)/C(=C/C)C1=CC=CC(O)=C1 TZOOYBCJSXMJPM-MFGIPTIESA-N 0.000 description 4
- TZOOYBCJSXMJPM-OCSIRBNJSA-N 3-[(e)-5-(dimethylamino)-4-methylpent-2-en-3-yl]phenol;hydrochloride Chemical compound Cl.CN(C)CC(C)\C(=C/C)C1=CC=CC(O)=C1 TZOOYBCJSXMJPM-OCSIRBNJSA-N 0.000 description 4
- BZRRKCWIPYYGLW-UHFFFAOYSA-N Cl.CN(CC(C)C(=C)C=1C=C(C=CC1)O)C Chemical compound Cl.CN(CC(C)C(=C)C=1C=C(C=CC1)O)C BZRRKCWIPYYGLW-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229960004380 tramadol Drugs 0.000 description 4
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 4
- QVWGKOYVOZJNRJ-UHFFFAOYSA-N 1-(dimethylamino)-2-methylpentan-3-one Chemical compound CCC(=O)C(C)CN(C)C QVWGKOYVOZJNRJ-UHFFFAOYSA-N 0.000 description 3
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 3
- DJYZWEYOQWPKCJ-UHFFFAOYSA-N 2-[1-(3-methoxyphenyl)ethenyl]-n,n-dimethylpentan-1-amine;hydrochloride Chemical compound Cl.CCCC(CN(C)C)C(=C)C1=CC=CC(OC)=C1 DJYZWEYOQWPKCJ-UHFFFAOYSA-N 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
- RUFSZLYNACSUDL-UHFFFAOYSA-N 3-(3-methoxyphenyl)-n,n,2,4-tetramethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(C(C)CN(C)C)=C(C)C)=C1 RUFSZLYNACSUDL-UHFFFAOYSA-N 0.000 description 3
- SDSRJHFFCZOQFF-HAZZGOGXSA-N 3-[(e)-1-(dimethylamino)-2-methylhex-3-en-3-yl]phenol;hydrochloride Chemical compound Cl.CN(C)CC(C)\C(=C/CC)C1=CC=CC(O)=C1 SDSRJHFFCZOQFF-HAZZGOGXSA-N 0.000 description 3
- SDSRJHFFCZOQFF-DFPPEFKWSA-N 3-[(z)-1-(dimethylamino)-2-methylhex-3-en-3-yl]phenol;hydrochloride Chemical compound Cl.CN(C)CC(C)/C(=C/CC)C1=CC=CC(O)=C1 SDSRJHFFCZOQFF-DFPPEFKWSA-N 0.000 description 3
- VIBKCCHMNVUCEA-UHFFFAOYSA-N 3-[3-(difluoromethyl)phenyl]-1-(dimethylamino)-2-methylpentan-3-ol Chemical compound CN(C)CC(C)C(O)(CC)C1=CC=CC(C(F)F)=C1 VIBKCCHMNVUCEA-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 239000000730 antalgic agent 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
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229940005483 opioid analgesics Drugs 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- QDHLEFBSGUGHCL-UHFFFAOYSA-N 2-[(dimethylamino)methyl]cyclohexan-1-one Chemical compound CN(C)CC1CCCCC1=O QDHLEFBSGUGHCL-UHFFFAOYSA-N 0.000 description 2
- BYTITZBFNNYKEE-UHFFFAOYSA-N 2-[6-[(dimethylamino)methyl]cyclohexen-1-yl]phenol;hydrochloride Chemical compound Cl.CN(C)CC1CCCC=C1C1=CC=CC=C1O BYTITZBFNNYKEE-UHFFFAOYSA-N 0.000 description 2
- BLZKSRBAQDZAIX-UHFFFAOYSA-N 2-methyl-1-benzothiophene Chemical compound C1=CC=C2SC(C)=CC2=C1 BLZKSRBAQDZAIX-UHFFFAOYSA-N 0.000 description 2
- IRGWVAWLHXDKIX-PBCQUBLHSA-N 3-[(1r,2r)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol;hydrochloride Chemical compound Cl.CN(C)C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1 IRGWVAWLHXDKIX-PBCQUBLHSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000000094 Chronic Pain Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ISFZZSTVAAOUQM-QCCPDHKASA-N (1r,2r,5s)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-5-methylcyclohexan-1-ol;hydrochloride Chemical compound Cl.COC1=CC=CC([C@]2(O)[C@H](CC[C@H](C)C2)CN(C)C)=C1 ISFZZSTVAAOUQM-QCCPDHKASA-N 0.000 description 1
- ISFZZSTVAAOUQM-DGVZIRGRSA-N (1s,2s,5r)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-5-methylcyclohexan-1-ol;hydrochloride Chemical compound Cl.COC1=CC=CC([C@@]2(O)[C@@H](CC[C@@H](C)C2)CN(C)C)=C1 ISFZZSTVAAOUQM-DGVZIRGRSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- PPKXEPBICJTCRU-XMZRARIVSA-N (R,R)-tramadol hydrochloride Chemical compound Cl.COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-XMZRARIVSA-N 0.000 description 1
- PIARDTFGLNPXMD-AWXXIEIHSA-N (e)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=C\C)\C(C)CN(C)C)=C1 PIARDTFGLNPXMD-AWXXIEIHSA-N 0.000 description 1
- JHKJGWJFBYPMCY-UUASQNMZSA-N (z)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=C/C)\C(C)CN(C)C)=C1 JHKJGWJFBYPMCY-UUASQNMZSA-N 0.000 description 1
- SUODVTRGWCTGEF-PSUINESXSA-N (z)-n,n,2-trimethyl-3-(3-methylphenyl)pent-3-en-1-amine;hydrochloride Chemical compound Cl.CN(C)CC(C)/C(=C/C)C1=CC=CC(C)=C1 SUODVTRGWCTGEF-PSUINESXSA-N 0.000 description 1
- BBTXSBPZBKNEDB-UHFFFAOYSA-N 1-(dimethylamino)-2,4-dimethylpentan-3-one Chemical compound CC(C)C(=O)C(C)CN(C)C BBTXSBPZBKNEDB-UHFFFAOYSA-N 0.000 description 1
- ABXRRVPKFOAILP-UHFFFAOYSA-N 1-(dimethylamino)-2-methyl-3-(3-methylphenyl)pentan-3-ol;hydrochloride Chemical compound Cl.CN(C)CC(C)C(O)(CC)C1=CC=CC(C)=C1 ABXRRVPKFOAILP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
-
- 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
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- 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
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- 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
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- 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
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19609847A DE19609847A1 (de) | 1996-03-13 | 1996-03-13 | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
Publications (2)
Publication Number | Publication Date |
---|---|
SK32197A3 SK32197A3 (en) | 1997-12-10 |
SK284328B6 true SK284328B6 (sk) | 2005-01-03 |
Family
ID=7788151
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK321-97A SK284328B6 (sk) | 1996-03-13 | 1997-03-12 | Dimetyl-(3-aryl-but-3-enyl)-aminozlúčeniny, spôsob ich výroby a ich použitie na výrobu liečiv |
Country Status (28)
Country | Link |
---|---|
US (1) | US5811582A (zh) |
EP (4) | EP0983994A3 (zh) |
JP (2) | JP4205182B2 (zh) |
KR (2) | KR100538662B1 (zh) |
CN (1) | CN1157366C (zh) |
AR (1) | AR008991A1 (zh) |
AT (3) | ATE223888T1 (zh) |
AU (1) | AU725430B2 (zh) |
BR (1) | BR9700369B1 (zh) |
CA (1) | CA2199679C (zh) |
CO (1) | CO4520279A1 (zh) |
CZ (1) | CZ293971B6 (zh) |
DE (4) | DE19609847A1 (zh) |
DK (3) | DK0983995T3 (zh) |
ES (3) | ES2183030T3 (zh) |
HK (2) | HK1026197A1 (zh) |
HU (1) | HU224819B1 (zh) |
IL (1) | IL120430A (zh) |
NO (1) | NO308294B1 (zh) |
NZ (1) | NZ314384A (zh) |
PE (1) | PE55798A1 (zh) |
PL (1) | PL186050B1 (zh) |
PT (3) | PT799819E (zh) |
RU (1) | RU2167146C2 (zh) |
SI (3) | SI0983995T1 (zh) |
SK (1) | SK284328B6 (zh) |
UA (1) | UA55373C2 (zh) |
ZA (1) | ZA972147B (zh) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
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DE4426245A1 (de) | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
DE19732928C2 (de) * | 1997-07-31 | 2000-05-18 | Gruenenthal Gmbh | Verwendung substituierter Imidazolidin-2,4-dion-Verbindungen als Schmerzmittel |
DE19830105C1 (de) * | 1998-07-06 | 2000-02-17 | Gruenenthal Gmbh | Acridinderivate |
ES2141688B1 (es) * | 1998-11-06 | 2001-02-01 | Vita Invest Sa | Nuevos esteres derivados de compuestos fenil-ciclohexil sustituidos. |
DE10000311A1 (de) * | 2000-01-05 | 2001-07-12 | Gruenenthal Gmbh | Aminomethyl-Phonyl-Cyclohexanonderivate |
DE10025948A1 (de) * | 2000-05-26 | 2001-11-29 | Gruenenthal Gmbh | Wirkstoffkombination |
DE10049483A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte 1-Aminobutan-3-ol-Derivate |
DE10049481A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte C-Cyclohexylmethylamin-Derivate |
DE10059413A1 (de) * | 2000-11-30 | 2002-06-20 | Gruenenthal Gmbh | Verwendung von substituierten 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbindungen zur Therapie der Harninkontinenz |
US20050176790A1 (en) | 2001-02-28 | 2005-08-11 | Johannes Bartholomaus | Pharmaceutical salts |
PT1397126E (pt) | 2001-03-16 | 2006-10-31 | Dmi Biosciences Inc | Utilizacao de tramadol para retardar a ejaculacao |
DE10132747A1 (de) * | 2001-07-05 | 2003-01-23 | Gruenenthal Gmbh | Substituierte 1-Aryl-but-3-enylamin- und 1-Aryl-but-2-enylaminverbindungen |
DE10146275A1 (de) * | 2001-09-18 | 2003-04-24 | Gruenenthal Gmbh | Kombination ausgewählter Opioide mit Muscarin-Antagonisten zur Therapie der Harninkontinenz |
PE20030527A1 (es) | 2001-10-24 | 2003-07-26 | Gruenenthal Chemie | Formulacion farmaceutica con liberacion retardada que contiene 3-(3-dimetilamino-1-etil-2-metil-propil) fenol o una sal farmaceuticamente aceptable del mismo y tabletas para administracion oral que la contienen |
DE10224624A1 (de) * | 2002-05-30 | 2003-12-11 | Gruenenthal Gmbh | Metabolite und Prodrugs von 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol |
DE10225315A1 (de) * | 2002-06-06 | 2003-12-24 | Gruenenthal Gmbh | Wirkstoffsalze und Ester von 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl- pentan-3-ol und 3-(3-Dimethylamino-1-ethyl-1-hydroxy-2-methyl- propyl)-phenol |
DE10261091A1 (de) * | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Gesättigte und ungesättigte Heteroarylcycloalkylmethyl-Amine |
DE10326097A1 (de) | 2003-06-06 | 2005-01-05 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
DE10328316A1 (de) * | 2003-06-23 | 2005-01-20 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe |
DE102004034619A1 (de) * | 2004-07-16 | 2006-02-23 | Grünenthal GmbH | Substituierte Aminoverbindungen als 5-HT/NA Uptakehemmer |
DE102005033732B4 (de) | 2005-05-27 | 2014-02-13 | Grünenthal GmbH | Trennung stereoisomerer N,N-Dialkylamino-2-alkyl-3-hydroxy-3-phenyl-alkane |
DE102005052588A1 (de) | 2005-11-02 | 2007-05-10 | Grünenthal GmbH | Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse |
DE102005061429A1 (de) * | 2005-12-22 | 2007-06-28 | Grünenthal GmbH | Substituierte Oxazol-Derivate |
TWI496762B (zh) * | 2006-07-24 | 2015-08-21 | 製備(1r,2r)-3-(3-二甲胺基-1-乙基-2-甲基-丙基)-酚之方法 | |
DE602007004494D1 (de) * | 2006-07-24 | 2010-03-11 | Janssen Pharmaceutica Nv | Herstellung von (2r,3r)-3-(3-methoxyphenyl)-n,n,2- trimethylpentanamin |
CN101948397A (zh) * | 2010-09-07 | 2011-01-19 | 天津泰普药品科技发展有限公司 | 镇痛药他喷他多重要中间体的制备方法 |
US8552219B2 (en) | 2010-09-20 | 2013-10-08 | Ind-Swift Laboratories Limited | Process for preparing L-phenyl-3-dimethylaminopropane derivative |
EP2674414A1 (en) | 2012-06-15 | 2013-12-18 | Siegfried AG | Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds |
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DE1518663A1 (de) * | 1965-08-02 | 1969-12-18 | Gruenenthal Chemie | Basisch substituierte Cycloalken-derivate und Verfahren zu ihrer Herstellung |
US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
US3978129A (en) * | 1972-01-28 | 1976-08-31 | A. H. Robins Company, Incorporated | Alkenyl- and alkanylamines |
DE2409990C2 (de) * | 1974-02-27 | 1982-11-25 | Siemens AG, 1000 Berlin und 8000 München | Meßwandler für Hochspannungsschaltanlagen mit Metallkapselung |
GB1502635A (en) * | 1974-02-27 | 1978-03-01 | Schering Ag | Process for splitting steroid ethers |
JPS598259B2 (ja) * | 1976-01-01 | 1984-02-23 | 武田薬品工業株式会社 | 新規シクロヘキセン誘導体 |
US4173649A (en) * | 1978-02-27 | 1979-11-06 | E. R. Squibb & Sons, Inc. | 5-Phenyl-2,4-pentadien-1-amines and method for inhibiting prostaglandin dehydrogenase |
FR2559765B1 (fr) * | 1984-02-16 | 1986-06-13 | Rhone Poulenc Sante | Nouveaux derives de la phenyl-3 propene-2 amine, leur preparation et les medicaments qui les contiennent |
IT1213219B (it) * | 1984-09-28 | 1989-12-14 | Consiglio Nazionale Ricerche | Derivati amminoalchilnaftalenici ad attivita' farmacologica. |
US5430044A (en) * | 1987-02-06 | 1995-07-04 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
SE9202218D0 (sv) * | 1992-07-22 | 1992-07-22 | Kabi Pharmacia Ab | Pharmacologically active alfa-(tertiary-aminomethyl)-benzenemethanol derivatives, pharmaceutical composition containing them, therapeutical use thereof and processes for their preparation |
DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
-
1996
- 1996-03-13 DE DE19609847A patent/DE19609847A1/de not_active Withdrawn
-
1997
- 1997-02-22 EP EP99119108A patent/EP0983994A3/de not_active Withdrawn
- 1997-02-22 EP EP99119109A patent/EP0983995B1/de not_active Expired - Lifetime
- 1997-02-22 EP EP00116745A patent/EP1069106B1/de not_active Expired - Lifetime
- 1997-02-22 SI SI9730653T patent/SI0983995T1/xx unknown
- 1997-02-22 DE DE59711477T patent/DE59711477D1/de not_active Expired - Lifetime
- 1997-02-22 PT PT97102923T patent/PT799819E/pt unknown
- 1997-02-22 ES ES97102923T patent/ES2183030T3/es not_active Expired - Lifetime
- 1997-02-22 EP EP97102923A patent/EP0799819B1/de not_active Expired - Lifetime
- 1997-02-22 DK DK99119109T patent/DK0983995T3/da active
- 1997-02-22 PT PT00116745T patent/PT1069106E/pt unknown
- 1997-02-22 DE DE59708160T patent/DE59708160D1/de not_active Expired - Lifetime
- 1997-02-22 DE DE59711267T patent/DE59711267D1/de not_active Expired - Lifetime
- 1997-02-22 SI SI9730428T patent/SI0799819T1/xx unknown
- 1997-02-22 AT AT97102923T patent/ATE223888T1/de active
- 1997-02-22 DK DK00116745T patent/DK1069106T3/da active
- 1997-02-22 PT PT99119109T patent/PT983995E/pt unknown
- 1997-02-22 AT AT00116745T patent/ATE258544T1/de active
- 1997-02-22 ES ES99119109T patent/ES2218924T3/es not_active Expired - Lifetime
- 1997-02-22 DK DK97102923T patent/DK0799819T3/da active
- 1997-02-22 SI SI9730618T patent/SI1069106T1/xx unknown
- 1997-02-22 AT AT99119109T patent/ATE263140T1/de active
- 1997-02-22 ES ES00116745T patent/ES2213526T3/es not_active Expired - Lifetime
- 1997-03-07 PE PE1997000175A patent/PE55798A1/es not_active Application Discontinuation
- 1997-03-07 BR BRPI9700369-7A patent/BR9700369B1/pt not_active IP Right Cessation
- 1997-03-11 NZ NZ314384A patent/NZ314384A/xx unknown
- 1997-03-11 KR KR1019970008046A patent/KR100538662B1/ko not_active IP Right Cessation
- 1997-03-11 AR ARP970100969A patent/AR008991A1/es active IP Right Grant
- 1997-03-11 CA CA002199679A patent/CA2199679C/en not_active Expired - Fee Related
- 1997-03-12 UA UA97031138A patent/UA55373C2/uk unknown
- 1997-03-12 CN CNB971034877A patent/CN1157366C/zh not_active Expired - Fee Related
- 1997-03-12 NO NO971137A patent/NO308294B1/no not_active IP Right Cessation
- 1997-03-12 JP JP05769597A patent/JP4205182B2/ja not_active Expired - Fee Related
- 1997-03-12 ZA ZA9702147A patent/ZA972147B/xx unknown
- 1997-03-12 CZ CZ1997759A patent/CZ293971B6/cs not_active IP Right Cessation
- 1997-03-12 HU HU9700574A patent/HU224819B1/hu not_active IP Right Cessation
- 1997-03-12 US US08/820,377 patent/US5811582A/en not_active Expired - Lifetime
- 1997-03-12 AU AU16251/97A patent/AU725430B2/en not_active Ceased
- 1997-03-12 PL PL97318922A patent/PL186050B1/pl not_active IP Right Cessation
- 1997-03-12 RU RU97103580/04A patent/RU2167146C2/ru active
- 1997-03-12 SK SK321-97A patent/SK284328B6/sk not_active IP Right Cessation
- 1997-03-12 IL IL12043097A patent/IL120430A/xx not_active IP Right Cessation
- 1997-03-12 CO CO97013358A patent/CO4520279A1/es unknown
-
2000
- 2000-08-24 HK HK00105323A patent/HK1026197A1/xx not_active IP Right Cessation
-
2001
- 2001-03-20 HK HK01101989A patent/HK1031864A1/xx not_active IP Right Cessation
-
2005
- 2005-06-03 KR KR1020050047916A patent/KR100602810B1/ko not_active IP Right Cessation
-
2008
- 2008-03-17 JP JP2008066934A patent/JP4846750B2/ja not_active Expired - Fee Related
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Legal Events
Date | Code | Title | Description |
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MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20100312 |