SK283663B6 - Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej - Google Patents
Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej Download PDFInfo
- Publication number
- SK283663B6 SK283663B6 SK1621-97A SK162197A SK283663B6 SK 283663 B6 SK283663 B6 SK 283663B6 SK 162197 A SK162197 A SK 162197A SK 283663 B6 SK283663 B6 SK 283663B6
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- carbamoylmethyl
- methylhexanoic acid
- methylhexanoic
- reacting
- Prior art date
Links
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- NPDKTSLVWGFPQG-SSDOTTSWSA-N (3r)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical compound CC(C)C[C@H](CC(N)=O)CC(O)=O NPDKTSLVWGFPQG-SSDOTTSWSA-N 0.000 claims abstract description 42
- UATSLDZQNXAKMA-UHFFFAOYSA-N 3-(2-methylpropyl)pentanedioic acid Chemical compound CC(C)CC(CC(O)=O)CC(O)=O UATSLDZQNXAKMA-UHFFFAOYSA-N 0.000 claims abstract description 25
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims abstract description 22
- -1 alkyl cyanoacetate Chemical compound 0.000 claims abstract description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 8
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- NPDKTSLVWGFPQG-UHFFFAOYSA-N 3-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical compound CC(C)CC(CC(N)=O)CC(O)=O NPDKTSLVWGFPQG-UHFFFAOYSA-N 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- XLSGYCWYKZCYCK-UHFFFAOYSA-N 4-(2-methylpropyl)oxane-2,6-dione Chemical compound CC(C)CC1CC(=O)OC(=O)C1 XLSGYCWYKZCYCK-UHFFFAOYSA-N 0.000 claims description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- NPDKTSLVWGFPQG-ZETCQYMHSA-N (3s)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical compound CC(C)C[C@@H](CC(N)=O)CC(O)=O NPDKTSLVWGFPQG-ZETCQYMHSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 6
- 239000012346 acetyl chloride Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical class C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical group CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 4
- JPWITCRJVNDZOC-UHFFFAOYSA-N 2-cyano-5-methylhex-2-enoic acid Chemical compound CC(C)CC=C(C#N)C(O)=O JPWITCRJVNDZOC-UHFFFAOYSA-N 0.000 claims description 4
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims 5
- VVOMQUUPOSVZDJ-MRVPVSSYSA-N (3s)-3-(2-aminoethyl)-5-methylhexanoic acid Chemical compound CC(C)C[C@@H](CCN)CC(O)=O VVOMQUUPOSVZDJ-MRVPVSSYSA-N 0.000 claims 4
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 150000008045 alkali metal halides Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000001537 neural effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 108091022930 Glutamate decarboxylase Proteins 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
- ZQFYQLSPBFLIHX-ZETCQYMHSA-N (2s)-2-(aminomethyl)-5-methylhexanoic acid Chemical compound CC(C)CC[C@@H](CN)C(O)=O ZQFYQLSPBFLIHX-ZETCQYMHSA-N 0.000 description 2
- AYXYPKUFHZROOJ-UHFFFAOYSA-N 3-(azaniumylmethyl)-5-methylhexanoate Chemical compound CC(C)CC(CN)CC(O)=O AYXYPKUFHZROOJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000000573 anti-seizure effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- AVGXIMRWATWCHC-HFEGYEGKSA-N (3r)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid;(1r)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1.CC(C)C[C@H](CC(N)=O)CC(O)=O AVGXIMRWATWCHC-HFEGYEGKSA-N 0.000 description 1
- PPIBJOQGAJBQDF-VXNVDRBHSA-N (4r,5s)-4-methyl-5-phenyl-1,3-oxazolidin-2-one Chemical compound C[C@H]1NC(=O)O[C@H]1C1=CC=CC=C1 PPIBJOQGAJBQDF-VXNVDRBHSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- PEZNEXFPRSOYPL-UHFFFAOYSA-N (bis(trifluoroacetoxy)iodo)benzene Chemical compound FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)C1=CC=CC=C1 PEZNEXFPRSOYPL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RKURAVRGGUYOLJ-UHFFFAOYSA-N 2-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical compound CC(C)CCC(C(O)=O)CC(N)=O RKURAVRGGUYOLJ-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- HCNGDJQHZLJWRQ-UHFFFAOYSA-N C(C)(=O)OC1(C(C=CC=C1)I)OC(C)=O Chemical compound C(C)(=O)OC1(C(C=CC=C1)I)OC(C)=O HCNGDJQHZLJWRQ-UHFFFAOYSA-N 0.000 description 1
- 108090000489 Carboxy-Lyases Proteins 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000006105 Hofmann reaction Methods 0.000 description 1
- 206010061296 Motor dysfunction Diseases 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KTLFENNEPHBKJD-UHFFFAOYSA-K benzyl(trimethyl)azanium;tribromide Chemical compound [Br-].[Br-].[Br-].C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1 KTLFENNEPHBKJD-UHFFFAOYSA-K 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000003842 bromide salts Chemical class 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000792 effect on seizure Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- 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
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/458,950 US5616793A (en) | 1995-06-02 | 1995-06-02 | Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| PCT/US1996/005831 WO1996038405A1 (en) | 1995-06-02 | 1996-04-26 | Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK162197A3 SK162197A3 (en) | 1998-10-07 |
| SK283663B6 true SK283663B6 (sk) | 2003-11-04 |
Family
ID=23822760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1621-97A SK283663B6 (sk) | 1995-06-02 | 1996-04-26 | Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US5616793A (cs) |
| EP (1) | EP0828704B1 (cs) |
| JP (1) | JP3965440B2 (cs) |
| AT (1) | ATE214361T1 (cs) |
| AU (1) | AU699982B2 (cs) |
| CZ (1) | CZ297631B6 (cs) |
| DE (1) | DE69619809T2 (cs) |
| DK (1) | DK0828704T3 (cs) |
| EE (1) | EE03964B1 (cs) |
| ES (1) | ES2173279T3 (cs) |
| HU (1) | HUP9802090A3 (cs) |
| NZ (1) | NZ307030A (cs) |
| PL (1) | PL185034B1 (cs) |
| PT (1) | PT828704E (cs) |
| SK (1) | SK283663B6 (cs) |
| WO (1) | WO1996038405A1 (cs) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU228426B1 (hu) | 1996-07-24 | 2013-03-28 | Warner Lambert Co | Izobutil-gaba és származékai alkalmazása fájdalom kezelésére alkalmas gyógyszer elõállítására |
| WO2001055090A1 (en) * | 2000-01-27 | 2001-08-02 | Warner-Lambert Company | Asymmetric synthesis of pregabalin |
| EP1543831A1 (en) * | 2003-12-18 | 2005-06-22 | Pfizer GmbH Arzneimittelwerk Gödecke | Pregabalin composition |
| ES2292107T3 (es) * | 2004-03-12 | 2008-03-01 | Warner-Lambert Company Llc | Ligandos de bifosfina simetricos en c1 y su uso en la sintesis asimetrica de pregabalina. |
| KR100847927B1 (ko) * | 2004-06-21 | 2008-07-22 | 워너-램버트 캄파니 엘엘씨 | 프레가발린 및 관련 화합물의 제조방법 |
| WO2006108151A1 (en) * | 2005-04-06 | 2006-10-12 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of pregabalin |
| US7488846B2 (en) * | 2005-04-11 | 2009-02-10 | Teva Pharmaceuical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| EP1768950A2 (en) * | 2005-04-11 | 2007-04-04 | Teva Pharmaceutical Industries Ltd. | Process for making (s)-pregabalin |
| JP2008505980A (ja) * | 2005-05-10 | 2008-02-28 | テバ ファーマシューティカル インダストリーズ リミティド | イソブチルグルタル酸を有さないプレガバリン及びその調製方法 |
| WO2006122258A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Method for the preparation of pregabalin and salts thereof |
| WO2006121557A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| EP1879854B1 (en) * | 2005-05-10 | 2011-09-07 | Teva Pharmaceutical Industries Ltd | Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid |
| CN100410242C (zh) * | 2005-06-23 | 2008-08-13 | 江苏恩华药业股份有限公司 | 普瑞巴林中间体及其制备方法 |
| BRPI0606118A2 (pt) | 2005-09-19 | 2009-06-02 | Teva Pharma | uma sìntese assimétrica de (s) - (+) -3- (aminometil) -5- ácido metilhexanóico |
| NL2000281C2 (nl) | 2005-11-02 | 2007-08-07 | Pfizer Prod Inc | Vaste farmaceutische samenstellingen die pregabaline bevatten. |
| US20070259917A1 (en) * | 2006-04-24 | 2007-11-08 | Kansal Vinod K | Processes for the synthesis of 3-isobutylglutaric acid |
| CA2649115A1 (en) * | 2006-05-24 | 2007-12-06 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof |
| US20080015385A1 (en) * | 2006-05-31 | 2008-01-17 | Lilach Hedvati | Preparation of (S)-pregabalin-nitrile |
| WO2007143113A2 (en) | 2006-05-31 | 2007-12-13 | Teva Pharmaceutical Industries Ltd. | The use of enzymatic resolution for the preparation of intermediates of pregabalin |
| ITMI20061297A1 (it) * | 2006-07-04 | 2008-01-05 | Laboratorio Chimico Int Spa | Procedimento per la preparazione della'acido (r)-(-)-3-(carbamoilmetil)-5-metilesanoico e del pregabalin e intermedi di sintesi |
| GB0614133D0 (en) * | 2006-07-15 | 2006-08-23 | Pliva Istrazivanje I Razvoj D | Process for preparing a pharmaceutical compound |
| KR101036536B1 (ko) * | 2007-03-22 | 2011-05-24 | 테바 파마슈티컬 인더스트리즈 리미티드 | (ｓ)-(+)-3-(아미노메틸)-5-메틸 헥산산의 합성 |
| WO2008137512A2 (en) * | 2007-05-03 | 2008-11-13 | Dr. Reddy's Laboratories Ltd. | Process for preparing pregabalin via hofmann reaction and crystalline form thereof |
| WO2009004643A2 (en) * | 2007-05-08 | 2009-01-08 | Cadila Healthcare Limited | An improved process for preparation of (s)-pregabalin and intermediates thereof |
| EP1992609A1 (en) * | 2007-05-14 | 2008-11-19 | Dipharma Francis S.r.l. | A process for the preparation of a (S)(+)-3-(aminomethyl)-5-methylhexanoic acid |
| WO2009046309A2 (en) * | 2007-10-03 | 2009-04-09 | Teva Pharmaceutical Industries Ltd. | Pregabalin -4-eliminate, pregabalin 5-eliminate, their use as reference marker and standard, and method to produce pregabalin containing low levels thereof |
| JP5234901B2 (ja) * | 2007-10-04 | 2013-07-10 | 学校法人東京理科大学 | 不斉触媒マイケル反応生成物の製造方法 |
| DK2225198T3 (da) * | 2007-11-30 | 2013-02-11 | Laboratorio Chimico Int Spa | Fremgangsmåde til fremstilling af en substitueret gamma-aminosyre |
| ITMI20072262A1 (it) * | 2007-12-03 | 2009-06-04 | Dipharma Francis Srl | Procedimento per la preparazione di acido (s)(+)-3-(amminometil)-5-metilesanoico |
| US20100312010A1 (en) * | 2007-12-18 | 2010-12-09 | Watson Pharma Private Limited | Process for the Preparation of (S)-Pregabalin |
| US20110144383A1 (en) * | 2008-02-18 | 2011-06-16 | Matrix Laboratories Limited | Process for preparing (s)-3-(aminomethyl)-5-methylhexanoic acid |
| UA103997C2 (ru) | 2008-05-21 | 2013-12-25 | Сандоз Аг | Способ стереоселективного ферментативного гидролиза эстера 5-метил-3-нитрометилгексановой кислоты |
| US20100087525A1 (en) * | 2008-06-23 | 2010-04-08 | Lilach Hedvati | Stereoselective enzymatic synthesis of (s) or (r)-iso-butyl-glutaric ester |
| WO2010070593A2 (en) | 2008-12-19 | 2010-06-24 | Pfizer Ireland Pharmaceuticals | Malonate esters |
| EP2213659A1 (en) | 2009-01-29 | 2010-08-04 | The Provost, Fellows and Scholars of the College of the Holy and Undivided Trinity of Queen Elizabeth near Dublin | Intermediates in the Enantioselective Synthesis of 3-(Aminomethyl)-5-Methyl-Hexanoic Acid |
| CN101987826A (zh) * | 2009-08-04 | 2011-03-23 | 铜陵凯顺生物科技有限公司 | 一种(3s)-3-氨甲基-5-甲基己酸的合成方法 |
| CN102126979A (zh) * | 2009-12-15 | 2011-07-20 | 中国科学院成都有机化学有限公司 | 一种光学纯的3-(氨甲酰甲基)-5-甲基己酸的制备方法 |
| ES2362913B1 (es) | 2009-12-24 | 2012-05-24 | Moehs Iberica S.L. | Nuevo método para la preparación de (s)-pregabalina. |
| WO2011077463A1 (en) * | 2009-12-24 | 2011-06-30 | Msn Laboratories Limited | Process for preparing pregabalin and its intermediate |
| WO2011078172A1 (ja) * | 2009-12-25 | 2011-06-30 | 株式会社カネカ | 光学活性３－置換グルタル酸モノアミドの製造法 |
| US8212072B2 (en) | 2010-08-13 | 2012-07-03 | Divi's Laboratories, Ltd. | Process for the preparation of pregabalin |
| WO2012025861A1 (en) | 2010-08-23 | 2012-03-01 | Pfizer Manufacturing Ireland | Process for the preparation of ( s ) - 3 - cyano - 5 - methylhexanoic acid derivatives adn of pregabalin |
| KR101306585B1 (ko) * | 2011-04-14 | 2013-09-10 | 한국외국어대학교 연구산학협력단 | 프레가발린의 제조방법 |
| EP2700645A4 (en) | 2011-04-20 | 2014-09-24 | Kemphys Ltd | SILICONE-CONTAINING CARBOXYLENE DERIVATIVE |
| WO2013076630A1 (en) | 2011-11-24 | 2013-05-30 | Lupin Limited | Novel process for racemization of an optically active (s)-3-carbamoylmethyl-5-methyl-hexanoic acid to corresponding 3-carbamoylmethyl-5-methyl-hexanoic acid racemate |
| CN102863326A (zh) * | 2012-03-20 | 2013-01-09 | 常州制药厂有限公司 | 一种抗癫痫药物中间体的制备方法 |
| JP5572783B1 (ja) | 2012-10-18 | 2014-08-13 | 有限会社ケムフィズ | ケイ素含有カルボン酸誘導体 |
| CN102898320A (zh) * | 2012-10-26 | 2013-01-30 | 浙江省天台县奥锐特药业有限公司 | (3r)-(-)-3-(2-乙酰氨基)-5-甲基己酸的制备方法 |
| US10023885B2 (en) | 2012-11-07 | 2018-07-17 | Hikal Limited | Process for the preparation of pregabalin |
| CN102964263B (zh) * | 2012-11-29 | 2014-12-03 | 太仓市茜泾化工有限公司 | 一种(±)-3-(氨甲酰基)-5-甲基己酸的制备方法 |
| CN103980144B (zh) * | 2014-05-16 | 2018-08-17 | 浙江华海药业股份有限公司 | 一种普瑞巴林中间体母液的套用方法 |
| CN104086439B (zh) * | 2014-06-30 | 2018-11-16 | 浙江华海药业股份有限公司 | 一种pregabalin中间体拆分剂(R)-(+)-α-苯乙胺的回收方法 |
| CN104356016B (zh) | 2014-10-24 | 2019-08-23 | 浙江华海药业股份有限公司 | 一种用回收制备3-异丁基戊二酸单酰胺的方法 |
| WO2016075082A1 (en) | 2014-11-10 | 2016-05-19 | Sandoz Ag | Stereoselective reductive amination of alpha-chiral aldehydes using omega-transaminases for the synthesis of precursors of pregabalin and brivaracetam |
| CN104496832A (zh) * | 2014-11-21 | 2015-04-08 | 浙江美诺华药物化学有限公司 | 一种普瑞巴林的合成方法 |
| CN104557577B (zh) * | 2014-12-26 | 2016-08-17 | 上海臣邦医药科技有限公司 | 高纯度(+)-普瑞巴林和(-)-普瑞巴林的制备方法 |
| US10450315B2 (en) | 2015-01-08 | 2019-10-22 | Lee Pharma Limited | Process for the preparation of dipeptidyl peptidase-4 (DPP-4) enzyme inhibitor |
| CN104803869A (zh) * | 2015-03-27 | 2015-07-29 | 浙江华海药业股份有限公司 | 一种无溶剂反应制备3-异丁基戊二酸单酰胺的方法 |
| CN104803868B (zh) * | 2015-03-27 | 2020-10-02 | 浙江华海药业股份有限公司 | 一种回收3-异丁基戊二酸单酰胺的方法 |
| CN104803871B (zh) * | 2015-05-12 | 2021-03-05 | 浙江华海药业股份有限公司 | 一种制备普瑞巴林中间体的方法 |
| CN104892441A (zh) * | 2015-05-22 | 2015-09-09 | 浙江华海药业股份有限公司 | 一种制备普瑞巴林异构体r-普瑞巴林的方法 |
| CN107920987A (zh) | 2015-05-26 | 2018-04-17 | 艾萨·欧蒂迪 | 控制延缓释放普瑞巴林 |
| WO2017019791A1 (en) | 2015-07-27 | 2017-02-02 | Teva Pharmaceuticals International Gmbh | Synthesis of (s)-pregabalin |
| CN105481712A (zh) * | 2015-11-30 | 2016-04-13 | 常州市阳光药业有限公司 | 普瑞巴林中间体拆分母液的消旋回收方法 |
| WO2019193607A1 (en) * | 2018-04-04 | 2019-10-10 | Msn Laboratories Private Limited, R&D Center | An improved process for the preparation of pregabalin |
| CN108912004B (zh) * | 2018-08-01 | 2021-05-07 | 宏冠生物药业有限公司 | 一种普瑞巴林中间体的合成方法 |
| CN109942446B (zh) * | 2019-04-17 | 2021-09-07 | 黄冈鲁班药业股份有限公司 | 一种普瑞巴林的制备方法 |
| CN112062689A (zh) * | 2019-06-11 | 2020-12-11 | 太仓市茜泾化工有限公司 | 一种r-3-（氨甲酰基）-5-甲基己酸的制备方法 |
| CN113045468A (zh) * | 2019-12-26 | 2021-06-29 | 上虞京新药业有限公司 | 一种布瓦西坦中间体的制备方法 |
| EP4103168A4 (en) | 2020-02-14 | 2024-04-24 | Council Of Scientific & Industrial Research | PROCESS FOR PREPARING GAMMA-AMINO-BUTYRIC ACIDS AND THEIR ANALOGS |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2944969A (en) * | 1957-02-06 | 1960-07-12 | Petrolite Corp | Prevention of rust and corrosion |
| US3544467A (en) * | 1966-02-07 | 1970-12-01 | Chevron Res | Acid-amide pour point depressants |
| US3857879A (en) * | 1967-12-04 | 1974-12-31 | W Abramitis | Amine salts of substituted succinamic acids |
| US4024174A (en) * | 1973-12-25 | 1977-05-17 | Ono Pharmaceutical Company | Tranes-delta 2-prostaglandins |
| US4123438A (en) * | 1975-03-05 | 1978-10-31 | Stamicarbon, B.V. | Process for preparing 2-pyrrolidones |
| US4739114A (en) * | 1982-09-30 | 1988-04-19 | Rhone-Poulenc Agrochimie | Process for the preparation of 3-alkyl-substituted glutaric acids and 2-alkyl-substituted succinic acids |
| US4711671A (en) * | 1985-10-03 | 1987-12-08 | National Starch And Chemical Corporation | Storage stable paper size composition containing ethoxylated lanolin |
| DE4033259A1 (de) * | 1990-10-19 | 1992-04-23 | Basf Ag | Verfahren zur herstellung von 2-pyrrolidinonen |
| WO1993023383A1 (en) * | 1992-05-20 | 1993-11-25 | Northwestern University | Gaba and l-glutamic acid analogs for antiseizure treatment |
-
1995
- 1995-06-02 US US08/458,950 patent/US5616793A/en not_active Expired - Lifetime
-
1996
- 1996-04-26 EP EP96913186A patent/EP0828704B1/en not_active Expired - Lifetime
- 1996-04-26 AT AT96913186T patent/ATE214361T1/de not_active IP Right Cessation
- 1996-04-26 PT PT96913186T patent/PT828704E/pt unknown
- 1996-04-26 SK SK1621-97A patent/SK283663B6/sk not_active IP Right Cessation
- 1996-04-26 HU HU9802090A patent/HUP9802090A3/hu unknown
- 1996-04-26 CZ CZ0374297A patent/CZ297631B6/cs not_active IP Right Cessation
- 1996-04-26 WO PCT/US1996/005831 patent/WO1996038405A1/en not_active Application Discontinuation
- 1996-04-26 PL PL96323563A patent/PL185034B1/pl unknown
- 1996-04-26 EE EE9700311A patent/EE03964B1/xx not_active IP Right Cessation
- 1996-04-26 JP JP53647696A patent/JP3965440B2/ja not_active Expired - Fee Related
- 1996-04-26 DK DK96913186T patent/DK0828704T3/da active
- 1996-04-26 DE DE69619809T patent/DE69619809T2/de not_active Expired - Fee Related
- 1996-04-26 ES ES96913186T patent/ES2173279T3/es not_active Expired - Lifetime
- 1996-04-26 NZ NZ307030A patent/NZ307030A/xx unknown
- 1996-04-26 AU AU55778/96A patent/AU699982B2/en not_active Ceased
- 1996-06-28 US US08/672,783 patent/US5629447A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9802090A2 (hu) | 1998-12-28 |
| EE03964B1 (et) | 2003-02-17 |
| EP0828704A1 (en) | 1998-03-18 |
| CZ297631B6 (cs) | 2007-02-14 |
| PL185034B1 (pl) | 2003-02-28 |
| EE9700311A (et) | 1998-06-15 |
| US5629447A (en) | 1997-05-13 |
| NZ307030A (en) | 1999-02-25 |
| JP3965440B2 (ja) | 2007-08-29 |
| DK0828704T3 (da) | 2002-07-01 |
| ATE214361T1 (de) | 2002-03-15 |
| US5616793A (en) | 1997-04-01 |
| SK162197A3 (en) | 1998-10-07 |
| DE69619809D1 (de) | 2002-04-18 |
| EP0828704B1 (en) | 2002-03-13 |
| JPH11506098A (ja) | 1999-06-02 |
| DE69619809T2 (de) | 2002-09-26 |
| CZ374297A3 (cs) | 1998-10-14 |
| ES2173279T3 (es) | 2002-10-16 |
| AU5577896A (en) | 1996-12-18 |
| HUP9802090A3 (en) | 1999-08-30 |
| AU699982B2 (en) | 1998-12-17 |
| PT828704E (pt) | 2002-08-30 |
| PL323563A1 (en) | 1998-04-14 |
| WO1996038405A1 (en) | 1996-12-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK283663B6 (sk) | Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej | |
| EP0830338B1 (en) | Method of making 3-(aminomethyl)-5-methylhexanoic acid | |
| US11384050B1 (en) | Method for preparing levetiracetam and intermediates thereof | |
| WO2008009897A1 (en) | Process for preparing pregabalin and its opposite enantiomer | |
| US4297282A (en) | Resolution of mercaptopropionic acids | |
| US20080312457A1 (en) | Process | |
| US4724102A (en) | Optical resolution of racemic mixtures of alpha-naphthylpropionic acids and derivatives of said acids | |
| HU204247B (en) | Process for optical resolving raceme compositions of alpha-naphtyl-propionic acid derivatives | |
| JPS60132930A (ja) | ａ‐ナフチルプロピオン酸のラセミ混合物の光学分割法 | |
| US6140529A (en) | Synthesis of optically active cyclohexylphenylglycolate esters | |
| CA2219278C (en) | Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid | |
| US4411836A (en) | Racemization of an α-methyl-β-acylthiopropionic acid | |
| MXPA97008338A (en) | Methods to make acid (s) -3- (aminomethyl) -5-methylhexane | |
| AU700091C (en) | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid | |
| JPH1059947A (ja) | キラルで、非ラセミの（４−アリール−２，５−ジオキソイミダゾリジン−１−イル）酢酸の製造方法 | |
| WO1991001968A1 (en) | Phenyl-glycine derivatives | |
| EP0179487A1 (en) | 2-Phenylpropionic acid esters, method for optical resolution thereof and optically active substance thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20090426 |