NO326227B1 - Nye stereoselektive fremgangsmater for fremstilling av gabapentinanaloger - Google Patents

Nye stereoselektive fremgangsmater for fremstilling av gabapentinanaloger Download PDF

Info

Publication number: NO326227B1
Authority: NO; Norway
Prior art keywords: mixture; prepare; solvent; dissolving; compound
Prior art date: 1997-09-18

Application number

NO20001404A

Other languages

English (en)

Norwegian (no)

Other versions

NO20001404D0 (no

NO20001404L (no

Inventor

Justin Stephen Bryans

Andrew Ian Morrell

Original Assignee

Warner Lambert Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-09-18

Filing date

2000-03-17

Publication date

2008-10-20

2000-03-17 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2000-03-17 Publication of NO20001404D0 publication Critical patent/NO20001404D0/no

2000-03-17 Publication of NO20001404L publication Critical patent/NO20001404L/no

2008-10-20 Publication of NO326227B1 publication Critical patent/NO326227B1/no

Links

UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical class OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 title abstract description 10
238000000034 method Methods 0.000 title abstract description 8
238000002360 preparation method Methods 0.000 title abstract description 3
230000000707 stereoselective effect Effects 0.000 title abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 32
239000002904 solvent Substances 0.000 claims description 22
150000002148 esters Chemical class 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
229910000104 sodium hydride Inorganic materials 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
150000003951 lactams Chemical class 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 8
239000012312 sodium hydride Substances 0.000 claims description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 claims description 6
UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 claims description 4
VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims description 2
HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims 6
150000001875 compounds Chemical class 0.000 claims 5
150000003839 salts Chemical class 0.000 claims 3
MSANHHHQJYQEOK-UHFFFAOYSA-N 3,5-dimethylcyclohexan-1-one Chemical compound CC1CC(C)CC(=O)C1 MSANHHHQJYQEOK-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 11
239000007787 solid Substances 0.000 description 9
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
-1 triphenylphosphonium halide Chemical class 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000010409 thin film Substances 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
239000012267 brine Substances 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
239000011698 potassium fluoride Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
MSANHHHQJYQEOK-KNVOCYPGSA-N (3r,5s)-3,5-dimethylcyclohexan-1-one Chemical compound C[C@H]1C[C@@H](C)CC(=O)C1 MSANHHHQJYQEOK-KNVOCYPGSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
229960002870 gabapentin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Silicates, Zeolites, And Molecular Sieves (AREA)
Crystals, And After-Treatments Of Crystals (AREA)
Indole Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO20001404A 1997-09-18 2000-03-17 Nye stereoselektive fremgangsmater for fremstilling av gabapentinanaloger NO326227B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5920497P	1997-09-18	1997-09-18
PCT/US1998/016652 WO1999014184A1 (en)	1997-09-18	1998-08-11	Novel stereoselective processes for the preparation of gabapentin analogues

Publications (3)

Publication Number	Publication Date
NO20001404D0 NO20001404D0 (no)	2000-03-17
NO20001404L NO20001404L (no)	2000-03-17
NO326227B1 true NO326227B1 (no)	2008-10-20

Family

ID=22021467

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20001404A NO326227B1 (no)	1997-09-18	2000-03-17	Nye stereoselektive fremgangsmater for fremstilling av gabapentinanaloger

Country Status (20)

Country	Link
US (1)	US6465689B1 (is)
EP (1)	EP1015415B1 (is)
JP (1)	JP3878809B2 (is)
KR (1)	KR100563894B1 (is)
AT (1)	ATE239695T1 (is)
AU (1)	AU752444B2 (is)
BR (1)	BR9812351A (is)
CA (1)	CA2295993C (is)
DE (1)	DE69814420T2 (is)
DK (1)	DK1015415T3 (is)
ES (1)	ES2197493T3 (is)
HU (1)	HUP0004582A3 (is)
IL (2)	IL133782A0 (is)
IS (1)	IS2198B (is)
NO (1)	NO326227B1 (is)
NZ (1)	NZ502786A (is)
PL (1)	PL192180B1 (is)
PT (1)	PT1015415E (is)
WO (1)	WO1999014184A1 (is)
ZA (1)	ZA988508B (is)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10203122A1 (de) *	2002-01-25	2003-07-31	Gruenenthal Gmbh	Verfahren zur Herstellung von substituierten Acrylsäureestern bzw. deren Einsatz zur Herstellung von substituierten gamma-Aminosäuren
US7439387B2 (en)	2003-04-21	2008-10-21	Matrix Laboratories Ltd.	Process for the preparation of Gabapentin form-II
US20050187295A1 (en) *	2004-02-19	2005-08-25	Surendra Kalyan	Processes for the preparation of gabapentin
US7632864B2 (en)	2004-03-17	2009-12-15	Hikal Ltd.	Gabapentin analogues and process thereof
CA2570255A1 (en)	2004-03-17	2005-09-22	Hikal Limited	4-t-butylgabapentin and its synthesis
US7442834B2 (en)	2006-06-12	2008-10-28	Zhejiang Chiral Medicine Chemicals Co., Ltd.	Process suitable for industrial scale production of gabapentin
WO2013190357A1 (en) *	2012-06-18	2013-12-27	Hikal Limited	A process for the preparation of gabapentin

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3928182A1 (de)	1989-08-25	1991-02-28	Goedecke Ag	Verfahren zur herstellung von gabapentin
EP0888325B1 (en) *	1996-02-07	2002-05-29	Warner-Lambert Company	Novel cyclic amino acids as pharmaceutical agents
IL125364A0 (en)	1996-03-14	1999-03-12	Warner Lambert Co	Novel bridged cyclic amino acids and pharmaceutical compositions containing them

1998
- 1998-08-11 AT AT98939340T patent/ATE239695T1/de not_active IP Right Cessation
- 1998-08-11 IL IL13378298A patent/IL133782A0/xx active IP Right Grant
- 1998-08-11 WO PCT/US1998/016652 patent/WO1999014184A1/en not_active Ceased
- 1998-08-11 DE DE69814420T patent/DE69814420T2/de not_active Expired - Fee Related
- 1998-08-11 BR BR9812351-3A patent/BR9812351A/pt active Search and Examination
- 1998-08-11 KR KR1020007002825A patent/KR100563894B1/ko not_active Expired - Fee Related
- 1998-08-11 EP EP98939340A patent/EP1015415B1/en not_active Expired - Lifetime
- 1998-08-11 PL PL339296A patent/PL192180B1/pl not_active IP Right Cessation
- 1998-08-11 HU HU0004582A patent/HUP0004582A3/hu unknown
- 1998-08-11 PT PT98939340T patent/PT1015415E/pt unknown
- 1998-08-11 DK DK98939340T patent/DK1015415T3/da active
- 1998-08-11 ES ES98939340T patent/ES2197493T3/es not_active Expired - Lifetime
- 1998-08-11 CA CA002295993A patent/CA2295993C/en not_active Expired - Fee Related
- 1998-08-11 JP JP2000511737A patent/JP3878809B2/ja not_active Expired - Fee Related
- 1998-08-11 AU AU87791/98A patent/AU752444B2/en not_active Ceased
- 1998-08-11 NZ NZ502786A patent/NZ502786A/en unknown
- 1998-08-11 US US09/445,633 patent/US6465689B1/en not_active Expired - Fee Related
- 1998-09-17 ZA ZA988508A patent/ZA988508B/xx unknown
1999
- 1999-12-29 IL IL133782A patent/IL133782A/en not_active IP Right Cessation
2000
- 2000-01-21 IS IS5355A patent/IS2198B/is unknown
- 2000-03-17 NO NO20001404A patent/NO326227B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL133782A (en)	2006-12-31
IS5355A (is)	2000-05-22
NZ502786A (en)	2002-05-31
EP1015415B1 (en)	2003-05-07
US6465689B1 (en)	2002-10-15
PL339296A1 (en)	2000-12-04
DK1015415T3 (da)	2003-07-21
NO20001404D0 (no)	2000-03-17
HUP0004582A3 (en)	2002-01-28
JP3878809B2 (ja)	2007-02-07
DE69814420T2 (de)	2003-11-27
DE69814420D1 (de)	2003-06-12
BR9812351A (pt)	2000-09-19
PT1015415E (pt)	2003-09-30
KR20010024079A (ko)	2001-03-26
JP2001516738A (ja)	2001-10-02
PL192180B1 (pl)	2006-09-29
HUP0004582A2 (hu)	2001-05-28
ES2197493T3 (es)	2004-01-01
EP1015415A1 (en)	2000-07-05
AU8779198A (en)	1999-04-05
AU752444B2 (en)	2002-09-19
NO20001404L (no)	2000-03-17
CA2295993C (en)	2004-05-04
IL133782A0 (en)	2001-04-30
ZA988508B (en)	1999-03-30
CA2295993A1 (en)	1999-03-25
ATE239695T1 (de)	2003-05-15
WO1999014184A1 (en)	1999-03-25
IS2198B (is)	2007-02-15
KR100563894B1 (ko)	2006-03-24

Publication	Publication Date	Title
MX2007012606A (es)	2008-01-11	Proceso para elaborar (s)-pregabalina.
US5095148A (en)	1992-03-10	Process for the production of 1-(aminomethyl)cyclohexane acetic acid
HU226475B1 (en)	2009-01-28	Process for producing (1r,4s)- and (1s,4r)-1-amino-4-hydroxymethyl-2-cyclopentene and the new intermediates
WO2010100429A1 (en)	2010-09-10	Process for the preparation of cinacalcet and salts thereof, and intermediates for use in the process
NO326227B1 (no)	2008-10-20	Nye stereoselektive fremgangsmater for fremstilling av gabapentinanaloger
EP2061318B1 (en)	2012-03-21	Process for the synthesis of (+) and (-) -1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane
JPH06184069A (ja)	1994-07-05	α−ヒドロキシ−β−アミノカルボン酸の製造方法
US5136091A (en)	1992-08-04	Process for the production of 1-(aminomethyl) cyclohexane acetic acid
WO2025118134A1 (zh)	2025-06-12	一种苯磺酸米洛巴林的合成方法
EP1347960A1 (en)	2003-10-01	Process for preparing ( ) trans-4-p-fluorophenyl-3-hydroxymethyl-1
US5149870A (en)	1992-09-22	Process for the production of 1-(aminomethyl)cyclohexane acetic acid
MXPA00000063A (en)	2000-09-08	Novel stereoselective processes for the preparation of gabapentin analogues
EA003555B1 (ru)	2003-06-26	Способ получения 1-(аминометил)циклогексилуксусной кислоты
JP2810465B2 (ja)	1998-10-15	Ｎ−メチル−４−ｔ−ブチルベンジルアミンの製造法
JP3221636B2 (ja)	2001-10-22	３−フェニルスルホニルアミノ−ビシクロ［２，２，１］ヘプタン−２−カルボン酸アルキルエステルの製造方法
JPH10158239A (ja)	1998-06-16	４−ヒドロキシ−２−ピロリジノンの製造方法ならびに精製方法
HUP0104036A2 (hu)	2002-02-28	Aril-piperidin-karbonil-származékok és közbenső termékeik, és eljárás előállításukra
JPH07242614A (ja)	1995-09-19	光学活性なオキシム誘導体およびその製造方法
HK1127899B (en)	2012-09-21	Process for the synthesis of (+) and (-) -1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane
JPH0959265A (ja)	1997-03-04	光学活性オキサゾリジノン、その製造方法、製造の中間体および不斉補助基としての利用
AU2001226773A1 (en)	2002-07-16	Process for preparing (plus or minus) trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidine
EP3160937A1 (en)	2017-05-03	A novel method for synthesis of optically pure beta-amino alcohols

Legal Events

Date	Code	Title	Description
2010-03-22	MM1K	Lapsed by not paying the annual fees