ZA91410B - Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine - Google Patents

Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine

Info

Publication number: ZA91410B
Authority: ZA; South Africa
Prior art keywords: synthesis; physostigmine; enantioselection; intermediates; preparation
Prior art date: 1990-01-22

Application number

ZA91410A

Other languages

English (en)

Inventor

Thomas B K Lee

B K Lee Thomas

George S K Wong

S K Wong George

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

1991-01-21

Publication date

1991-10-30

1991-01-21 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1991-10-30 Publication of ZA91410B publication Critical patent/ZA91410B/xx

Links

230000015572 biosynthetic process Effects 0.000 title abstract 3
238000003786 synthesis reaction Methods 0.000 title abstract 3
PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 title abstract 2
238000000034 method Methods 0.000 title abstract 2
150000005623 oxindoles Chemical class 0.000 title abstract 2
PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 title abstract 2
229960001697 physostigmine Drugs 0.000 title abstract 2
239000000543 intermediate Substances 0.000 title 1
238000002360 preparation method Methods 0.000 title 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 abstract 2
150000003141 primary amines Chemical class 0.000 abstract 2
230000000707 stereoselective effect Effects 0.000 abstract 2
XEEBADQXIMNBQG-UHFFFAOYSA-N 3-(2-aminoethyl)-5-methoxy-1,3-dimethyl-2-indolone Chemical compound COC1=CC=C2N(C)C(=O)C(C)(CCN)C2=C1 XEEBADQXIMNBQG-UHFFFAOYSA-N 0.000 abstract 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
150000007960 acetonitrile Chemical class 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
239000003054 catalyst Substances 0.000 abstract 1
238000010531 catalytic reduction reaction Methods 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
239000002244 precipitate Substances 0.000 abstract 1
239000000047 product Substances 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
235000002906 tartaric acid Nutrition 0.000 abstract 1
239000011975 tartaric acid Substances 0.000 abstract 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)

ZA91410A 1990-01-22 1991-01-21 Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine ZA91410B (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
ZA91410B true ZA91410B (en)	1991-10-30

Family

ID=23865415

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA91410A ZA91410B (en)	1990-01-22	1991-01-21	Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine

Country Status (22)

Country	Link
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)	HUT56539A (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
DE69020989T2 (de) *	1989-09-19	1996-02-08	Hoechst Roussel Pharma	Verfahren zur Racematspaltung von 5-alkoxy-substituierten (+/-)-1,3-dimethyloxindolylethylaminen.
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
WO2002070478A1 (en)	2001-03-06	2002-09-12	Astrazeneca Ab	Indolone derivatives having vascular-damaging activity
JP6075563B2 (ja) *	2011-11-08	2017-02-08	日産化学工業株式会社	光学活性イソキサゾリン化合物の触媒的不斉合成方法及び光学活性イソキサゾリン化合物
WO2013138413A1 (en)	2012-03-14	2013-09-19	Merck Sharp & Dohme Corp.	Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE69020989T2 (de) *	1989-09-19	1996-02-08	Hoechst Roussel Pharma	Verfahren zur Racematspaltung von 5-alkoxy-substituierten (+/-)-1,3-dimethyloxindolylethylaminen.
US4914102A (en) *	1989-09-28	1990-04-03	Hoechst Roussel Pharmaceuticals, Inc.	N-aminocarbamates related to physostigmine, pharmacentical compositions and use
CN1071359C (zh)	1994-11-28	2001-09-19	美国3M公司	具有耐久的色彩和/或荧光性能的制品

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

Also Published As

Publication number	Publication date
CA2034668A1 (en)	1991-07-23
EP0438796A2 (en)	1991-07-31
YU9891A (sh)	1994-06-24
CS9100123A2 (en)	1991-09-15
HRP930321B1 (en)	1999-02-28
HU9801313D0 (en)	1998-08-28
HK1011993A1 (en)	1999-07-23
PT96534B (pt)	1998-07-31
CZ278815B6 (en)	1994-07-13
SG52631A1 (en)	1998-09-28
PH30059A (en)	1996-11-08
HU910210D0 (en)	1991-08-28
IE910194A1 (en)	1991-07-31
ATE170173T1 (de)	1998-09-15
IL97002A (en)	1994-10-21
PT96534A (pt)	1991-10-15
DK0438796T3 (da)	1999-05-25
HUT56539A (en)	1991-09-30
KR910014349A (ko)	1991-08-31
NZ236837A (en)	1993-03-26
AU6949691A (en)	1991-07-25
JPH0757747B2 (ja)	1995-06-21
LTIP1629A (en)	1995-07-25
KR0175933B1 (ko)	1999-03-20
ES2120407T3 (es)	1998-11-01
JPH04342566A (ja)	1992-11-30
AU631957B2 (en)	1992-12-10
DE69032595D1 (de)	1998-10-01
EP0438796A3 (en)	1992-03-18
RU2072354C1 (ru)	1997-01-27
HRP930321A2 (en)	1996-08-31
EP0438796B1 (en)	1998-08-26
IL97002A0 (en)	1992-03-29
DE69032595T2 (de)	1999-03-25
LT3982B (en)	1996-06-25

Publication	Publication Date	Title
GR3015887T3 (en)	1995-07-31	Chiral azabicyloheptanone and a process for their preparation.
GB2208646B (en)	1991-06-26	Indole derivatives
HRP930321B1 (en)	1999-02-28	Process for the enantioselection synthesis of alkylated oxyndoles used as intermediates in the preparation of physostigmine
HUT36127A (en)	1985-08-28	Process for preparing new pyrrolo-benzoxazepines
EP0802182A4 (en)	2001-01-17	PROCESS FOR THE PRODUCTION OF N- (D-alpha-METHYLE-beta-MERCAPTOPROPIONYL) -L-PROLINE AND ITS INTERMEDIATES
AU590748B2 (en)	1989-11-16	Benzo(C)-1,5-naphthyridines, a process and intermediates for their preparation and their use as medicaments
PL236951A1 (en)	1983-02-14	Process for preparing novel derivative of 1-benzyl-3,4-dihydroisoquinoline
ES8704895A1 (es)	1987-04-16	Un metodo para preparar 1-aminoalquilamino-4-ariloxipiperidinas sustituidas
HUT60716A (en)	1992-10-28	New process for producing 3-substituted indole compounds
HUT63829A (en)	1993-10-28	Process for producing (s)-vinyl- and allenyl-gabe, as well as (s)-vinyl- and allenyl-pyrrolidinone
DE3261465D1 (en)	1985-01-17	Process for the manufacture of l-proline
ES8605767A1 (es)	1986-04-01	Procedimiento de preparacion de un derivado del acido feni- lacetico