PL185560B1 - Sól kwasu migdałowego kwasu 3-(aminometylo)-5-metyloheksanowego - Google Patents
Sól kwasu migdałowego kwasu 3-(aminometylo)-5-metyloheksanowegoInfo
- Publication number
- PL185560B1 PL185560B1 PL96350439A PL35043996A PL185560B1 PL 185560 B1 PL185560 B1 PL 185560B1 PL 96350439 A PL96350439 A PL 96350439A PL 35043996 A PL35043996 A PL 35043996A PL 185560 B1 PL185560 B1 PL 185560B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- aminomethyl
- water
- solid
- mixture
- Prior art date
Links
- AYXYPKUFHZROOJ-UHFFFAOYSA-N 3-(azaniumylmethyl)-5-methylhexanoate Chemical compound CC(C)CC(CN)CC(O)=O AYXYPKUFHZROOJ-UHFFFAOYSA-N 0.000 title description 21
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical class CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims abstract description 16
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical class OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 claims abstract description 11
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims abstract description 11
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical class OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 9
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
- PZDIOSMERCSXQS-MRVPVSSYSA-N (2r)-2-ethyl-4-methylpentan-1-amine Chemical class CC[C@@H](CN)CC(C)C PZDIOSMERCSXQS-MRVPVSSYSA-N 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000007787 solid Substances 0.000 description 46
- 239000000203 mixture Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 22
- 238000004821 distillation Methods 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 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 7
- LCPQXKAEQQWPAB-UHFFFAOYSA-N 4-ethoxycarbonyl-7-methyloct-4-enoic acid Chemical compound CCOC(=O)C(CCC(O)=O)=CCC(C)C LCPQXKAEQQWPAB-UHFFFAOYSA-N 0.000 description 7
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229960002510 mandelic acid Drugs 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003880 polar aprotic solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- MBZSCAJFNRHIKS-UHFFFAOYSA-N 5-cyano-4-ethoxycarbonyl-7-methyloctanoic acid Chemical compound CCOC(=O)C(CCC(O)=O)C(CC(C)C)C#N MBZSCAJFNRHIKS-UHFFFAOYSA-N 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 4
- 108091022930 Glutamate decarboxylase Proteins 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000010268 HPLC based assay Methods 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000002858 neurotransmitter agent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
- UBMASBWZWXREGH-UHFFFAOYSA-N 4-ethoxycarbonyl-7-methyloct-5-enoic acid Chemical group CCOC(=O)C(CCC(O)=O)C=CC(C)C UBMASBWZWXREGH-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000012521 purified sample Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
- -1 3- (aminomethyl) -5-methylhexanoic acid mandelic acid salts Chemical class 0.000 description 1
- 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 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 108090000489 Carboxy-Lyases Proteins 0.000 description 1
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 1
- 230000000792 effect on seizure Effects 0.000 description 1
- WBQBMWWPFBMMOD-UHFFFAOYSA-N ethyl 3-cyano-5-methylhexanoate Chemical compound CCOC(=O)CC(C#N)CC(C)C WBQBMWWPFBMMOD-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- AYXYPKUFHZROOJ-SSDOTTSWSA-N pregabalin Chemical compound CC(C)C[C@@H](CN)CC(O)=O AYXYPKUFHZROOJ-SSDOTTSWSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000001665 trituration Methods 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
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- 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
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/10—Formation of amino groups in compounds containing carboxyl groups with simultaneously increasing the number of carbon atoms in the carbon skeleton
-
- 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
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
- C07C255/22—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton containing cyano groups and at least two carboxyl groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Seasonings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/474,874 US5637767A (en) | 1995-06-07 | 1995-06-07 | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| PCT/US1996/006819 WO1996040617A1 (en) | 1995-06-07 | 1996-05-13 | Method of making (s)-3-(aminomethyl)-5-methylhexanoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL185560B1 true PL185560B1 (pl) | 2003-06-30 |
Family
ID=23885291
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL96350439A PL185560B1 (pl) | 1995-06-07 | 1996-05-13 | Sól kwasu migdałowego kwasu 3-(aminometylo)-5-metyloheksanowego |
| PL96350438A PL185557B1 (pl) | 1995-06-07 | 1996-05-13 | Sposób wydzielania kwasu (S)-3-(aminometylo)-5-metyloheksanowego z kwasu (+)-3-(aminometylo)-5-metyloheksanowego |
| PL96323795A PL185425B1 (pl) | 1995-06-07 | 1996-05-13 | Pochodne kwasu 3 cyjano-5-metyloheksanowego oraz sposób wytwarzania kwasu (+)-3-(aminometylo)-5-metyloheksanowego |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL96350438A PL185557B1 (pl) | 1995-06-07 | 1996-05-13 | Sposób wydzielania kwasu (S)-3-(aminometylo)-5-metyloheksanowego z kwasu (+)-3-(aminometylo)-5-metyloheksanowego |
| PL96323795A PL185425B1 (pl) | 1995-06-07 | 1996-05-13 | Pochodne kwasu 3 cyjano-5-metyloheksanowego oraz sposób wytwarzania kwasu (+)-3-(aminometylo)-5-metyloheksanowego |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US5637767A (enExample) |
| EP (1) | EP0830338B1 (enExample) |
| JP (1) | JP3874306B2 (enExample) |
| AT (1) | ATE210628T1 (enExample) |
| CA (1) | CA2219150C (enExample) |
| CZ (2) | CZ296895B6 (enExample) |
| DE (1) | DE69617948T2 (enExample) |
| DK (1) | DK0830338T3 (enExample) |
| EE (1) | EE04053B1 (enExample) |
| ES (1) | ES2170231T3 (enExample) |
| GE (1) | GEP19991870B (enExample) |
| HU (2) | HU228194B1 (enExample) |
| NZ (2) | NZ308319A (enExample) |
| PL (3) | PL185560B1 (enExample) |
| PT (1) | PT830338E (enExample) |
| SI (1) | SI0830338T1 (enExample) |
| SK (2) | SK283507B6 (enExample) |
| WO (1) | WO1996040617A1 (enExample) |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5858736A (en) * | 1996-05-17 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Preparation of lactams from aliphatic α,ω-dinitriles |
| AU714980B2 (en) | 1996-07-24 | 2000-01-13 | Warner-Lambert Company Llc | Isobutylgaba and its derivatives for the treatment of pain |
| AU9019198A (en) | 1997-08-19 | 1999-03-08 | Warner-Lambert Company | Methods for treating physiological conditions associated with the use, or sequelae of use, of cocaine or other psychomotor stimulants |
| KR100694735B1 (ko) * | 1999-06-10 | 2007-03-14 | 워너-램버트 캄파니 엘엘씨 | 일치환 및 이치환된 3-프로필 감마-아미노부티르산 |
| US6891059B2 (en) * | 2000-01-27 | 2005-05-10 | Warner-Lambert Company | Asymmetric synthesis of pregabalin |
| GB2368579A (en) * | 2000-10-31 | 2002-05-08 | Parke Davis & Co Ltd | Azole pharmaceutical agents |
| US7169812B2 (en) * | 2003-07-01 | 2007-01-30 | Medtronic, Inc. | Process for producing injectable gabapentin compositions |
| EP1543831A1 (en) * | 2003-12-18 | 2005-06-22 | Pfizer GmbH Arzneimittelwerk Gödecke | Pregabalin composition |
| KR100823758B1 (ko) * | 2004-03-12 | 2008-04-21 | 워너-램버트 캄파니 엘엘씨 | Ｃ1-대칭 비스포스핀 리간드 및 프레가발린의 비대칭합성에서의 이들의 용도 |
| UA82292C2 (uk) * | 2004-04-14 | 2008-03-25 | Пфайзер Продактс Инк. | Спосіб стереоселективного біоперетворення аліфатичних динітрилів в ціанокарбонові кислоти (варіанти) |
| CN102102114B (zh) * | 2004-06-21 | 2013-08-14 | 沃尼尔·朗伯有限责任公司 | 普瑞巴林和相关化合物的制备 |
| US7417165B2 (en) * | 2005-04-06 | 2008-08-26 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of pregabalin |
| EP1768950A2 (en) * | 2005-04-11 | 2007-04-04 | Teva Pharmaceutical Industries Ltd. | Process for making (s)-pregabalin |
| US7488846B2 (en) * | 2005-04-11 | 2009-02-10 | Teva Pharmaceuical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| 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 |
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- 1996-05-13 HU HU9802504A patent/HU228194B1/hu unknown
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- 1996-05-13 DK DK96914618T patent/DK0830338T3/da active
- 1996-05-13 PL PL96350439A patent/PL185560B1/pl unknown
- 1996-05-13 CZ CZ20010732A patent/CZ296895B6/cs not_active IP Right Cessation
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- 1996-05-13 WO PCT/US1996/006819 patent/WO1996040617A1/en not_active Ceased
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- 1996-05-13 SK SK1645-97A patent/SK282865B6/sk not_active IP Right Cessation
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