ZA200600109B - Method for the producting of substituted 3-aryl-butyl amine compounds - Google Patents
Method for the producting of substituted 3-aryl-butyl amine compounds Download PDFInfo
- Publication number
- ZA200600109B ZA200600109B ZA200600109A ZA200600109A ZA200600109B ZA 200600109 B ZA200600109 B ZA 200600109B ZA 200600109 A ZA200600109 A ZA 200600109A ZA 200600109 A ZA200600109 A ZA 200600109A ZA 200600109 B ZA200600109 B ZA 200600109B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- phenyl
- dimethylamine
- methoxy
- dimethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 136
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- -1 p-isopropyl -phenyl -carbamoyl Chemical group 0.000 claims description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- JKVBTSJLQLSTHJ-SWLSCSKDSA-N (2r,3r)-3-(3-methoxyphenyl)-n,n,2-trimethylpentan-1-amine Chemical compound CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(OC)=C1 JKVBTSJLQLSTHJ-SWLSCSKDSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 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 16
- JHKJGWJFBYPMCY-FCGPPKDQSA-N (e,2r)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=C\C)\[C@@H](C)CN(C)C)=C1 JHKJGWJFBYPMCY-FCGPPKDQSA-N 0.000 claims description 13
- JKVBTSJLQLSTHJ-UHFFFAOYSA-N 3-(3-methoxyphenyl)-n,n,2-trimethylpentan-1-amine Chemical compound CN(C)CC(C)C(CC)C1=CC=CC(OC)=C1 JKVBTSJLQLSTHJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- JHKJGWJFBYPMCY-CJTQKWKHSA-N (z,2r)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=C/C)\[C@@H](C)CN(C)C)=C1 JHKJGWJFBYPMCY-CJTQKWKHSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- KWTWDQCKEHXFFR-UHFFFAOYSA-N 3-[1-(dimethylamino)-2-methylpentan-3-yl]phenol Chemical compound CN(C)CC(C)C(CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-UHFFFAOYSA-N 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- JHKJGWJFBYPMCY-UHFFFAOYSA-N 3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=CC)C(C)CN(C)C)=C1 JHKJGWJFBYPMCY-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- FKTFYPCLRBUSDX-UHFFFAOYSA-N 3-(3-methoxyphenyl)-2-methylpentan-3-ol Chemical compound CCC(O)(C(C)C)C1=CC=CC(OC)=C1 FKTFYPCLRBUSDX-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- KWTWDQCKEHXFFR-SMDDNHRTSA-N tapentadol Chemical compound CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-SMDDNHRTSA-N 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- PZNRRUTVGXCKFC-DOMZBBRYSA-N (2r,3s)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol Chemical compound CN(C)C[C@@H](C)[C@@](O)(CC)C1=CC=CC(OC)=C1 PZNRRUTVGXCKFC-DOMZBBRYSA-N 0.000 claims description 4
- JHKJGWJFBYPMCY-FVTUNSQFSA-N (z,2s)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=C/C)\[C@H](C)CN(C)C)=C1 JHKJGWJFBYPMCY-FVTUNSQFSA-N 0.000 claims description 4
- INCYIBYTUZLVLV-RISCZKNCSA-N 3-[(2r,3s)-1-(dimethylamino)-3-hydroxy-2-methylpentan-3-yl]phenol Chemical compound CN(C)C[C@@H](C)[C@@](O)(CC)C1=CC=CC(O)=C1 INCYIBYTUZLVLV-RISCZKNCSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- AXDGIPSSPVZITC-FDDCHVKYSA-N [3-[(2r,3r)-1-(dimethylamino)-2-methylpentan-3-yl]phenyl] n-(4-propan-2-ylphenyl)carbamate Chemical compound CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(OC(=O)NC=2C=CC(=CC=2)C(C)C)=C1 AXDGIPSSPVZITC-FDDCHVKYSA-N 0.000 claims description 3
- ZMUWFZKOOHQRKU-ZUHLXGTJSA-N [3-[(e,4r)-5-(dimethylamino)-4-methylpent-2-en-3-yl]phenyl] n-(4-propan-2-ylphenyl)carbamate Chemical compound CN(C)C[C@H](C)\C(=C/C)C1=CC=CC(OC(=O)NC=2C=CC(=CC=2)C(C)C)=C1 ZMUWFZKOOHQRKU-ZUHLXGTJSA-N 0.000 claims description 3
- ZMUWFZKOOHQRKU-YRFUCCNRSA-N [3-[(z,4r)-5-(dimethylamino)-4-methylpent-2-en-3-yl]phenyl] n-(4-propan-2-ylphenyl)carbamate Chemical compound CN(C)C[C@H](C)/C(=C/C)C1=CC=CC(OC(=O)NC=2C=CC(=CC=2)C(C)C)=C1 ZMUWFZKOOHQRKU-YRFUCCNRSA-N 0.000 claims description 3
- AXDGIPSSPVZITC-UHFFFAOYSA-N [3-[1-(dimethylamino)-2-methylpentan-3-yl]phenyl] n-(4-propan-2-ylphenyl)carbamate Chemical compound CN(C)CC(C)C(CC)C1=CC=CC(OC(=O)NC=2C=CC(=CC=2)C(C)C)=C1 AXDGIPSSPVZITC-UHFFFAOYSA-N 0.000 claims description 3
- ZMUWFZKOOHQRKU-UHFFFAOYSA-N [3-[5-(dimethylamino)-4-methylpent-2-en-3-yl]phenyl] n-(4-propan-2-ylphenyl)carbamate Chemical compound CN(C)CC(C)C(=CC)C1=CC=CC(OC(=O)NC=2C=CC(=CC=2)C(C)C)=C1 ZMUWFZKOOHQRKU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- PZNRRUTVGXCKFC-SWLSCSKDSA-N (2s,3r)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol Chemical compound CN(C)C[C@H](C)[C@](O)(CC)C1=CC=CC(OC)=C1 PZNRRUTVGXCKFC-SWLSCSKDSA-N 0.000 claims description 2
- INCYIBYTUZLVLV-BXUZGUMPSA-N 3-[(2r,3r)-1-(dimethylamino)-3-hydroxy-2-methylpentan-3-yl]phenol Chemical compound CN(C)C[C@@H](C)[C@](O)(CC)C1=CC=CC(O)=C1 INCYIBYTUZLVLV-BXUZGUMPSA-N 0.000 claims description 2
- INCYIBYTUZLVLV-UHFFFAOYSA-N 3-[1-(dimethylamino)-3-hydroxy-2-methylpentan-3-yl]phenol Chemical compound CN(C)CC(C)C(O)(CC)C1=CC=CC(O)=C1 INCYIBYTUZLVLV-UHFFFAOYSA-N 0.000 claims description 2
- XQYBUKLCTLZPHS-UHFFFAOYSA-N CNC.C(C)(C)C1=CC=C(C=C1)NC(=O)OC=1C=C(C=CC1)C(C(C)C)(CC)O Chemical compound CNC.C(C)(C)C1=CC=C(C=C1)NC(=O)OC=1C=C(C=CC1)C(C(C)C)(CC)O XQYBUKLCTLZPHS-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- 239000003929 acidic solution Substances 0.000 claims 5
- JHKJGWJFBYPMCY-BYQGBLLGSA-N (e,2s)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=C\C)\[C@H](C)CN(C)C)=C1 JHKJGWJFBYPMCY-BYQGBLLGSA-N 0.000 claims 4
- 239000011260 aqueous acid Substances 0.000 claims 4
- 239000003610 charcoal Substances 0.000 claims 4
- 239000011261 inert gas Substances 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- NJSYYJGNHXRFAW-UHFFFAOYSA-N 3-[5-(dimethylamino)-4-methylpent-1-en-3-yl]phenol Chemical compound CN(C)CC(C)C(C=C)C1=CC=CC(O)=C1 NJSYYJGNHXRFAW-UHFFFAOYSA-N 0.000 claims 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 2
- 239000010931 gold Substances 0.000 claims 2
- 229910052737 gold Inorganic materials 0.000 claims 2
- 229910000510 noble metal Inorganic materials 0.000 claims 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- 229920000728 polyester Polymers 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 description 17
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001768 cations Chemical class 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
- 239000003814 drug Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 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 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 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
- JHKJGWJFBYPMCY-LBPRGKRZSA-N (2r)-3-(3-methoxyphenyl)-n,n,2-trimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=CC)[C@@H](C)CN(C)C)=C1 JHKJGWJFBYPMCY-LBPRGKRZSA-N 0.000 description 1
- PZNRRUTVGXCKFC-IUODEOHRSA-N (2r,3r)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol Chemical compound CN(C)C[C@@H](C)[C@](O)(CC)C1=CC=CC(OC)=C1 PZNRRUTVGXCKFC-IUODEOHRSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
- NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 description 1
- VIKBNMWOLLIQPG-UHFFFAOYSA-N 2-methyldecanedioic acid Chemical compound OC(=O)C(C)CCCCCCCC(O)=O VIKBNMWOLLIQPG-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
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- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000021092 sugar substitutes Nutrition 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C07C217/64—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 further substituted by singly-bound oxygen atoms
- C07C217/66—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 further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/72—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 further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain 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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
-
- 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
- C07C211/27—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 saturated 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
- C07C211/28—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
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy 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
- C07C215/56—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 further substituted by hydroxy groups
- C07C215/58—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 further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/62—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 further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10326097A DE10326097A1 (de) | 2003-06-06 | 2003-06-06 | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
Publications (1)
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ZA200600109B true ZA200600109B (en) | 2007-01-31 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200600109A ZA200600109B (en) | 2003-06-06 | 2006-01-05 | Method for the producting of substituted 3-aryl-butyl amine compounds |
Country Status (26)
Country | Link |
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US (1) | US7417170B2 (fr) |
EP (1) | EP1633697B1 (fr) |
JP (1) | JP4848268B2 (fr) |
KR (1) | KR101146205B1 (fr) |
CN (1) | CN1829681B (fr) |
AT (1) | ATE425136T1 (fr) |
AU (1) | AU2004245223C1 (fr) |
BR (1) | BRPI0411268C8 (fr) |
CA (1) | CA2528087C (fr) |
CY (1) | CY1109088T1 (fr) |
DE (2) | DE10326097A1 (fr) |
DK (1) | DK1633697T3 (fr) |
EC (1) | ECSP056218A (fr) |
ES (1) | ES2323870T3 (fr) |
HK (1) | HK1088597A1 (fr) |
HR (1) | HRP20090333T1 (fr) |
IL (1) | IL172357A (fr) |
MX (1) | MXPA05013193A (fr) |
NO (1) | NO335587B1 (fr) |
NZ (1) | NZ544231A (fr) |
PL (1) | PL1633697T3 (fr) |
PT (1) | PT1633697E (fr) |
RU (1) | RU2380355C2 (fr) |
SI (1) | SI1633697T1 (fr) |
WO (1) | WO2004108658A1 (fr) |
ZA (1) | ZA200600109B (fr) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10328316A1 (de) | 2003-06-23 | 2005-01-20 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe |
DE102005052588A1 (de) | 2005-11-02 | 2007-05-10 | Grünenthal GmbH | Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse |
DK2046726T3 (da) * | 2006-07-24 | 2010-05-10 | Janssen Pharmaceutica Nv | Fremstilling af (2R,3R)-3-3-methoxyphenyl)-N,N, 2-trimethylpentanamin |
TWI448447B (zh) * | 2006-07-24 | 2014-08-11 | Gruenenthal Chemie | 製備(1r,2r)-3-(3-二甲胺基-1-乙基-2-甲基-丙基)-酚之方法 |
TWI401237B (zh) | 2006-07-24 | 2013-07-11 | 3-〔(1r,2r)-3-(二甲基氨基)-1-乙基-2-甲基丙基〕酚之製備 | |
ES2623413T3 (es) * | 2007-12-07 | 2017-07-11 | Grünenthal GmbH | Modificaciones cristalinas de (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenol |
WO2010100477A2 (fr) * | 2009-03-03 | 2010-09-10 | Shire Llc | Promédicaments de carbamate d'acide aminé et de peptide de tapentadol et leurs utilisations |
CN102002065B (zh) * | 2009-09-02 | 2014-09-10 | 上海特化医药科技有限公司 | 他喷他多的制备方法及其中间体 |
US8288592B2 (en) | 2009-09-22 | 2012-10-16 | Actavis Group Ptc Ehf | Solid state forms of tapentadol salts |
IT1397189B1 (it) * | 2009-12-01 | 2013-01-04 | Archimica Srl | Nuovo processo per la preparazione di tapentadol e suoi intermedi. |
MX2012007759A (es) | 2009-12-29 | 2012-08-01 | Mapi Pharma Ltd | Compuestos intermedios y procesos para la preparacion de tapentadol y compuestos relacionados. |
WO2011092719A2 (fr) * | 2010-02-01 | 2011-08-04 | Ind-Swift Laboratories Limited | Procédé de préparation de dérivés l-phényl-3-diméthylaminopropane |
AU2011222644A1 (en) | 2010-03-05 | 2012-09-06 | Actavis Group Ptc Ehf | Improved resolution methods for isolating desired enantiomers of tapentadol intermediates and use thereof for the preparation of tapentadol |
US20130096347A1 (en) | 2010-04-05 | 2013-04-18 | Actavis Group Ptc Ehf | Novel process for preparing highly pure tapentadol or a pharmaceutically acceptable salt thereof |
ITMI20100924A1 (it) * | 2010-05-21 | 2011-11-22 | Fidia Farmaceutici | Nuovo metodo di sintesi delle due forme enantiomeriche del tapentadol |
EP2582659B1 (fr) * | 2010-06-15 | 2015-03-11 | Grünenthal GmbH | Procédé de préparation de composés 3-(1-amino-2-methylpentane-3-yl)phényle substitué |
IT1401109B1 (it) | 2010-07-02 | 2013-07-12 | Archimica Srl | Nuovo processo per la preparazione di tapentadol e suoi intermedi. |
KR102146233B1 (ko) * | 2010-07-23 | 2020-08-21 | 그뤼넨탈 게엠베하 | 3-(3-디메틸아미노-1-에틸-2-메틸-프로필)-페놀의 염 또는 공결정 |
US8853456B2 (en) | 2010-08-16 | 2014-10-07 | Indoco Remedies Limited | Process for the preparation of tapentadol |
EP2619174A4 (fr) | 2010-09-20 | 2014-05-14 | Ind Swift Lab Ltd | Procédé de préparation de dérivés de l-phényl-3-diméthylaminopropane |
CN102477016B (zh) * | 2010-11-26 | 2014-12-17 | 中国医学科学院药物研究所 | 他喷他多的中间体的合成与应用 |
WO2012089181A1 (fr) * | 2010-12-30 | 2012-07-05 | Zentiva, K.S. | Acides (2r, 3r)-3-(3-hydroxyphényle)-2-méthyl-4-penténoïques o-substitués et leur procédé d'obtention |
CZ2010998A3 (cs) * | 2010-12-30 | 2012-02-08 | Zentiva, K.S. | Zpusob výroby (2R,3R)-N,N-dimethyl-3-(3-hydroxyfenyl)-2-methylpentylaminu (tapentadolu) |
CZ302992B6 (cs) * | 2010-12-30 | 2012-02-08 | Zentiva, K.S. | Zpusob výroby (2R,3R)-N,N-dimethyl-3-(3-hydroxyfenyl)-2-methylpentylaminu (tapentadolu) |
WO2012146978A2 (fr) | 2011-04-28 | 2012-11-01 | Actavis Group Ptc Ehf | Nouveau processus de préparation de tapentadol ou d'un sel pharmaceutiquement acceptable de ce dernier |
EP2530072A1 (fr) | 2011-06-03 | 2012-12-05 | Lacer, S.A. | Nouveaux composés, synthèse et utilisation dans le traitement de la douleur |
WO2013016840A1 (fr) | 2011-07-29 | 2013-02-07 | 安徽省新星药物开发有限责任公司 | Nouvel intermédiaire utilisé pour préparer du tapentadol ou ses analogues |
WO2013105109A1 (fr) | 2011-11-09 | 2013-07-18 | Indoco Remedies Limited | Procédé de préparation de tapentadol |
WO2013090161A1 (fr) | 2011-12-12 | 2013-06-20 | Boehringer Ingelheim International Gmbh | Synthèse stéréosélective du tapendatol et de ses sels |
WO2013120466A1 (fr) | 2012-02-17 | 2013-08-22 | Zentiva, K.S. | Nouvelle forme solide du tapentadol et procédé pour sa préparation |
EP2674414A1 (fr) | 2012-06-15 | 2013-12-18 | Siegfried AG | Appareils dýimpression |
CN103159633B (zh) * | 2012-07-06 | 2015-08-12 | 江苏恩华药业股份有限公司 | 他喷他多的制备方法及用于制备他喷他多的化合物 |
IN2013MU03670A (fr) | 2013-11-21 | 2015-07-31 | Unimark Remedies Ltd | |
WO2015091068A1 (fr) | 2013-12-16 | 2015-06-25 | Farma Grs, D.O.O. | Formes cristallines d'intermédiaire du tapentadol |
CZ307492B6 (cs) | 2014-02-04 | 2018-10-17 | Zentiva, K.S. | Pevná forma maleátu tapentadolu a způsob její přípravy |
PL3319941T3 (pl) | 2015-07-10 | 2022-05-02 | SpecGx LLC | Dwuetapowy sposób wytwarzania 3-podstawionych fenyloalkiloamin |
EP4269384A1 (fr) | 2022-04-26 | 2023-11-01 | KRKA, d.d., Novo mesto | PROCÉDÉ DE CRISTALLISATION d'un INTERMÉDIAIRE DE TAPENTADOL, INTERMÉDIAIRE DE TAPENTADOL DE HAUTE PURETÉ, PROCÉDÉ DE FABRICATION DE TAPENTADOL ET TAPENTADOL DE HAUTE PURETÉ |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3978129A (en) * | 1972-01-28 | 1976-08-31 | A. H. Robins Company, Incorporated | Alkenyl- and alkanylamines |
DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
DE19609847A1 (de) | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
DE19857475A1 (de) * | 1998-12-14 | 2000-06-15 | Gruenenthal Gmbh | Substituierte Cycloheptene, deren Herstellung und Verwendung |
DE19933421A1 (de) | 1999-07-16 | 2001-01-25 | Gruenenthal Gmbh | 2-Benzyl-3-dimethylamino-1-phenyl-propanderi- vate |
DE10000311A1 (de) * | 2000-01-05 | 2001-07-12 | Gruenenthal Gmbh | Aminomethyl-Phonyl-Cyclohexanonderivate |
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- 2004-06-04 EP EP04739583A patent/EP1633697B1/fr not_active Expired - Lifetime
- 2004-06-04 KR KR1020057023464A patent/KR101146205B1/ko active IP Right Grant
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