LT3982B - Process for the enantioselective synthesis of alkylated oxindoles - Google Patents

Process for the enantioselective synthesis of alkylated oxindoles Download PDF

Info

Publication number: LT3982B
Authority: LT; Lithuania
Prior art keywords: oxindole; process according; enantiomers; mixture; solvent
Prior art date: 1990-01-22

Application number

LTIP1629A

Other languages

English (en)

Lithuanian (lt)

Inventor

Thomas Bing Kin Dr Lee

George S K Wong

Original Assignee

Hoechst Roussel Pharma

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.)

1990-01-22

Filing date

1993-12-20

Publication date

1996-06-25

1993-12-20 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1995-07-25 Publication of LTIP1629A publication Critical patent/LTIP1629A/xx

1996-06-25 Publication of LT3982B publication Critical patent/LT3982B/lt

Links

238000000034 method Methods 0.000 title claims abstract description 64
230000008569 process Effects 0.000 title claims abstract description 40
230000015572 biosynthetic process Effects 0.000 title claims abstract description 38
150000005623 oxindoles Chemical class 0.000 title claims abstract description 35
238000003786 synthesis reaction Methods 0.000 title claims abstract description 35
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 abstract description 41
230000000707 stereoselective effect Effects 0.000 claims abstract description 22
239000002253 acid Substances 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
150000007960 acetonitrile Chemical class 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 53
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 claims description 37
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 35
239000011541 reaction mixture Substances 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
125000001309 chloro group Chemical group Cl* 0.000 claims description 14
230000002051 biphasic effect Effects 0.000 claims description 13
150000007529 inorganic bases Chemical class 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 claims description 10
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239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
150000003892 tartrate salts Chemical class 0.000 claims description 8
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150000002825 nitriles Chemical class 0.000 claims description 7
239000012071 phase Substances 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
229910052794 bromium Chemical group 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
-1 primary amine enantiomers Chemical class 0.000 claims description 6
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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JRUQXVDEQZLXLV-UHFFFAOYSA-N 1-benzyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1CC1=CC=CC=C1 JRUQXVDEQZLXLV-UHFFFAOYSA-N 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 11
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238000011914 asymmetric synthesis Methods 0.000 description 10
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238000000926 separation method Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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239000002168 alkylating agent Substances 0.000 description 7
229940100198 alkylating agent Drugs 0.000 description 7
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 7
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239000012670 alkaline solution Substances 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
230000008512 biological response Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960000846 camphor Drugs 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000012069 chiral reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000000718 cholinopositive effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
238000004891 communication Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000002964 excitative effect Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
230000006870 function Effects 0.000 description 1
210000000609 ganglia Anatomy 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000006698 induction Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000006984 memory degeneration Effects 0.000 description 1
208000023060 memory loss Diseases 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
210000000715 neuromuscular junction Anatomy 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
210000000225 synapse Anatomy 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Saccharide Compounds (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Inorganic Compounds Of Heavy Metals (AREA)

LTIP1629A 1990-01-22 1993-12-20 Process for the enantioselective synthesis of alkylated oxindoles LT3982B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US46988290A	1990-01-22	1990-01-22

Publications (2)

Publication Number	Publication Date
LTIP1629A LTIP1629A (en)	1995-07-25
LT3982B true LT3982B (en)	1996-06-25

Family

ID=23865415

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP1629A LT3982B (en)	1990-01-22	1993-12-20	Process for the enantioselective synthesis of alkylated oxindoles

Country Status (22)

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EP (1)	EP0438796B1 (cs)
JP (1)	JPH0757747B2 (cs)
KR (1)	KR0175933B1 (cs)
AT (1)	ATE170173T1 (cs)
AU (1)	AU631957B2 (cs)
CA (1)	CA2034668A1 (cs)
CZ (1)	CZ278815B6 (cs)
DE (1)	DE69032595T2 (cs)
DK (1)	DK0438796T3 (cs)
ES (1)	ES2120407T3 (cs)
HR (1)	HRP930321B1 (cs)
HU (2)	HU9801313D0 (cs)
IE (1)	IE910194A1 (cs)
IL (1)	IL97002A (cs)
LT (1)	LT3982B (cs)
NZ (1)	NZ236837A (cs)
PH (1)	PH30059A (cs)
PT (1)	PT96534B (cs)
RU (1)	RU2072354C1 (cs)
SG (1)	SG52631A1 (cs)
YU (1)	YU9891A (cs)
ZA (1)	ZA91410B (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0418770B1 (en) *	1989-09-19	1995-07-19	Hoechst-Roussel Pharmaceuticals Incorporated	Process for the chemical resolution of 5-alkoxy-substituted (+/-)-1,3-dimethyloxindolylethylamines
US4914102A (en) *	1989-09-28	1990-04-03	Hoechst Roussel Pharmaceuticals, Inc.	N-aminocarbamates related to physostigmine, pharmacentical compositions and use
US5521320A (en) *	1990-01-22	1996-05-28	Hoechst-Roussel Pharmaceuticals Incorporated	Process for the enantioselective synthesis of intermediates used in the preparation of physostigmine
US5840915A (en) *	1990-01-22	1998-11-24	Hoechst Marion Roussel, Inc.	Process for the enatioselective synthesis of intermediates used
GB0011120D0 (en) *	2000-05-09	2000-06-28	Avecia Ltd	Process
US6596870B2 (en)	2000-07-13	2003-07-22	Brandeis University	Asymmetric synthetic methods based on phase transfer catalysis
JP2004529110A (ja)	2001-03-06	2004-09-24	アストラゼネカアクチボラグ	脈管損傷活性を有するインドール誘導体
US9126995B2 (en) *	2011-11-08	2015-09-08	Nissan Chemical Industries, Ltd.	Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound
EP4019516A1 (en) *	2012-03-14	2022-06-29	Merck Sharp & Dohme Corp.	Asymmetric phase transfer catalysis

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US4578509A (en)	1983-04-01	1986-03-25	Merck & Co., Inc.	Process for preparing a manipulated enantiomer mixture by asymmetric chiral phase transfer catalysis
US4791107A (en)	1986-07-16	1988-12-13	Hoechst-Roussel Pharmaceuticals, Inc.	Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use
US5605761A (en)	1994-11-28	1997-02-25	Minnesota Mining And Manufacturing Company	Articles exhibiting durable color containing a polycarbonate, a fluorescent dye and an amine light stabilizer

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EP0418770B1 (en) *	1989-09-19	1995-07-19	Hoechst-Roussel Pharmaceuticals Incorporated	Process for the chemical resolution of 5-alkoxy-substituted (+/-)-1,3-dimethyloxindolylethylamines
US4914102A (en) *	1989-09-28	1990-04-03	Hoechst Roussel Pharmaceuticals, Inc.	N-aminocarbamates related to physostigmine, pharmacentical compositions and use

1990
- 1990-12-28 DE DE69032595T patent/DE69032595T2/de not_active Expired - Fee Related
- 1990-12-28 SG SG1996007048A patent/SG52631A1/en unknown
- 1990-12-28 EP EP90125644A patent/EP0438796B1/en not_active Expired - Lifetime
- 1990-12-28 AT AT90125644T patent/ATE170173T1/de not_active IP Right Cessation
- 1990-12-28 DK DK90125644T patent/DK0438796T3/da active
- 1990-12-28 ES ES90125644T patent/ES2120407T3/es not_active Expired - Lifetime
1991
- 1991-01-18 NZ NZ236837A patent/NZ236837A/xx unknown
- 1991-01-21 KR KR1019910000934A patent/KR0175933B1/ko not_active Expired - Fee Related
- 1991-01-21 HU HU9801313A patent/HU9801313D0/hu unknown
- 1991-01-21 HU HU91210A patent/HUT56539A/hu unknown
- 1991-01-21 IE IE019491A patent/IE910194A1/en not_active IP Right Cessation
- 1991-01-21 YU YU9891A patent/YU9891A/sh unknown
- 1991-01-21 CZ CS91123A patent/CZ278815B6/cs not_active IP Right Cessation
- 1991-01-21 CA CA002034668A patent/CA2034668A1/en not_active Abandoned
- 1991-01-21 AU AU69496/91A patent/AU631957B2/en not_active Ceased
- 1991-01-21 RU SU914894301A patent/RU2072354C1/ru active
- 1991-01-21 PT PT96534A patent/PT96534B/pt not_active IP Right Cessation
- 1991-01-21 JP JP3078153A patent/JPH0757747B2/ja not_active Expired - Lifetime
- 1991-01-21 PH PH41878A patent/PH30059A/en unknown
- 1991-01-21 ZA ZA91410A patent/ZA91410B/xx unknown
- 1991-01-22 IL IL9700291A patent/IL97002A/en not_active IP Right Cessation
1993
- 1993-03-11 HR HRP-98/91A patent/HRP930321B1/xx not_active IP Right Cessation
- 1993-12-20 LT LTIP1629A patent/LT3982B/lt not_active IP Right Cessation

Patent Citations (3)

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US4578509A (en)	1983-04-01	1986-03-25	Merck & Co., Inc.	Process for preparing a manipulated enantiomer mixture by asymmetric chiral phase transfer catalysis
US4791107A (en)	1986-07-16	1988-12-13	Hoechst-Roussel Pharmaceuticals, Inc.	Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use
US5605761A (en)	1994-11-28	1997-02-25	Minnesota Mining And Manufacturing Company	Articles exhibiting durable color containing a polycarbonate, a fluorescent dye and an amine light stabilizer

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D. L. HUGHES ET AL.: "Efficient catalytic asymmetric alkylations. 3. A kinetic and mechanistic study of the enantioselective phase-transfer methylation of 6,7-dichloro-5-methoxy-2-phenyl-1-indanone", J. ORG. CHEM, 1987, pages 745 - 4752
PERCY L. JULIAN, JOSEF PIKL: "Studies in the Indole Series. IV. The Synthesis of d,l-Eserethole", J. AM. CHEM. SOC., 1935, pages 563 - 566
PERCY L. JULIAN, JOSEF PIKL: "Studies in the Indole Series. V. The Complete Synthesis of Physostigmine (Eserine)", J. AM. CHEM. SOC., 1935, pages 755 - 757
SCHONENBERGER, B., BROSSI, A.: "Fragmentation of optically active (1-phenylethyl)- and (1-naphthylethyl)-ureas in refluxing alcohols: Easy preparation of optically active amines of high optical purity", HELV. CHIM. ACTA., 1986, pages 1486, XP055026358, DOI: doi:10.1002/hlca.19860690620

Also Published As

Publication number	Publication date
ZA91410B (en)	1991-10-30
HU9801313D0 (en)	1998-08-28
SG52631A1 (en)	1998-09-28
CZ278815B6 (en)	1994-07-13
YU9891A (sh)	1994-06-24
HRP930321A2 (en)	1996-08-31
JPH0757747B2 (ja)	1995-06-21
LTIP1629A (en)	1995-07-25
IL97002A (en)	1994-10-21
EP0438796A3 (en)	1992-03-18
RU2072354C1 (ru)	1997-01-27
ATE170173T1 (de)	1998-09-15
DK0438796T3 (da)	1999-05-25
DE69032595T2 (de)	1999-03-25
AU6949691A (en)	1991-07-25
CA2034668A1 (en)	1991-07-23
IL97002A0 (en)	1992-03-29
HUT56539A (en)	1991-09-30
HU910210D0 (en)	1991-08-28
ES2120407T3 (es)	1998-11-01
JPH04342566A (ja)	1992-11-30
PH30059A (en)	1996-11-08
DE69032595D1 (de)	1998-10-01
EP0438796A2 (en)	1991-07-31
KR910014349A (ko)	1991-08-31
HK1011993A1 (en)	1999-07-23
PT96534B (pt)	1998-07-31
NZ236837A (en)	1993-03-26
PT96534A (pt)	1991-10-15
EP0438796B1 (en)	1998-08-26
IE910194A1 (en)	1991-07-31
CS9100123A2 (en)	1991-09-15
HRP930321B1 (en)	1999-02-28
AU631957B2 (en)	1992-12-10
KR0175933B1 (ko)	1999-03-20

Legal Events

Date	Code	Title	Description
1997-06-25	PD9A	Change of patent owner	Free format text: HOECHST MARION ROUSSEL, INC.,10236 MARION PARK DRIVE, KANSAS CITY, MISSOURRI 64137-1405,US,19970429
2001-08-27	MM9A	Lapsed patents	Effective date: 20001220

Publication	Publication Date	Title
LT3982B (en)	1996-06-25	Process for the enantioselective synthesis of alkylated oxindoles
US5274117A (en)	1993-12-28	Process for the enantioselective synthesis of intermediates used in the preparation of physostigmine
RU2109013C1 (ru)	1998-04-20	Способ стереоселективного синтеза алкилированного оксиндола и способ получения оптически чистого энантиомера алкилированного оксиндола
EP0418770B1 (en)	1995-07-19	Process for the chemical resolution of 5-alkoxy-substituted (+/-)-1,3-dimethyloxindolylethylamines
US4614806A (en)	1986-09-30	Process for the asymmetric synthesis of chiral indoline-2-carboxylic acids
EP1354876B1 (fr)	2005-04-27	Nouveau procédé de synthèse de l'acide (2S, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application à la synthèse du perindopril
US5840915A (en)	1998-11-24	Process for the enatioselective synthesis of intermediates used
JP2008169204A (ja)	2008-07-24	（１ｒ，２ｒ）−２−アミノ−１−シクロペンタノールの製造方法
HK1040516A1 (en)	2002-06-14	Process for the production of paroxetine
US7943784B2 (en)	2011-05-17	Process for the preparation of almotriptan
HK1011993B (en)	2000-04-28	Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine
US4644081A (en)	1987-02-17	Process for the asymmetric synthesis of chiral indoline-2-carboxylic acids
EP0088849A1 (fr)	1983-09-21	Isomères lévogyres de composés benzènesulfonamides N-substitués, leur procédé de préparation et compositions pharmaceutiques les contenant