DK169965B1 - Fremgangsmåde til fremstilling af 4-substituerede indolin-2-oner, samt mellemprodukter til brug herved - Google Patents

Fremgangsmåde til fremstilling af 4-substituerede indolin-2-oner, samt mellemprodukter til brug herved Download PDF

Info

Publication number: DK169965B1
Authority: DK; Denmark
Prior art keywords: formula; compound; equivalents; chloride; preparation
Prior art date: 1987-06-19

Application number

DK334788A

Other languages

Danish (da)

English (en)

Other versions

DK334788D0 (da

DK334788A (da

Inventor

Joseph M Fortunak

Original Assignee

Smith Kline French Lab

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.)

1987-06-19

Filing date

1988-06-17

Publication date

1995-04-18

1988-06-17 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1988-06-17 Publication of DK334788D0 publication Critical patent/DK334788D0/da

1988-12-20 Publication of DK334788A publication Critical patent/DK334788A/da

1995-04-18 Application granted granted Critical

1995-04-18 Publication of DK169965B1 publication Critical patent/DK169965B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims description 19
239000000543 intermediate Chemical class 0.000 title description 2
150000005623 oxindoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 19
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 17
-1 acetyl halide Chemical class 0.000 claims abstract description 14
229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
239000002904 solvent Substances 0.000 claims abstract description 8
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 9
239000012346 acetyl chloride Substances 0.000 claims description 9
125000000217 alkyl 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
239000000460 chlorine Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000006476 reductive cyclization reaction Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical group CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims description 3
238000001953 recrystallisation Methods 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
238000005695 dehalogenation reaction Methods 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
239000000463 material Substances 0.000 claims 1
230000002829 reductive effect Effects 0.000 abstract description 3
150000001412 amines Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000010410 layer Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
PHDOYZATHWYOJK-UHFFFAOYSA-N 2-(2-bromoethyl)benzaldehyde Chemical compound BrCCC1=CC=CC=C1C=O PHDOYZATHWYOJK-UHFFFAOYSA-N 0.000 description 6
FUHGGNYHOLHJRR-UHFFFAOYSA-N 4-(2-bromoethyl)-3-chloro-1,3-dihydroindol-2-one Chemical compound C1=CC(CCBr)=C2C(Cl)C(=O)NC2=C1 FUHGGNYHOLHJRR-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
KJFSOQQZVCONSQ-UHFFFAOYSA-N 4-(2-bromoethyl)-1,3-dihydroindol-2-one Chemical compound BrCCC1=CC=CC2=C1CC(=O)N2 KJFSOQQZVCONSQ-UHFFFAOYSA-N 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
FCPRCFFVLWHIBS-UHFFFAOYSA-N 1-(2-bromoethyl)-2-(2-nitroethenyl)benzene Chemical compound [O-][N+](=O)C=CC1=CC=CC=C1CCBr FCPRCFFVLWHIBS-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000011928 denatured alcohol Substances 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
SYZVQXIUVGKCBJ-UHFFFAOYSA-N 1-ethenyl-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(C=C)=C1 SYZVQXIUVGKCBJ-UHFFFAOYSA-N 0.000 description 2
PIAOLBVUVDXHHL-UHFFFAOYSA-N 2-nitroethenylbenzene Chemical class [O-][N+](=O)C=CC1=CC=CC=C1 PIAOLBVUVDXHHL-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 2
HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
ACUGTEHQOFWBES-UHFFFAOYSA-M sodium hypophosphite monohydrate Chemical compound O.[Na+].[O-]P=O ACUGTEHQOFWBES-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ZGEXDLWUNWEAIA-UHFFFAOYSA-N 1,3-dihydroindol-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)CC2=C1 ZGEXDLWUNWEAIA-UHFFFAOYSA-N 0.000 description 1
UKOXLCVYPDKGMF-UHFFFAOYSA-N 4-(2-bromoethyl)-3-chloro-1,3-dihydroindol-2-one 4-(2-bromoethyl)-1,3-dihydroindol-2-one Chemical compound BrCCC1=C2C(C(NC2=CC=C1)=O)Cl.BrCCC1=C2CC(NC2=CC=C1)=O UKOXLCVYPDKGMF-UHFFFAOYSA-N 0.000 description 1
ZCFYCYNKQCLFQO-UHFFFAOYSA-N 4-ethenylindol-2-one Chemical compound C=CC1=CC=CC2=NC(=O)C=C12 ZCFYCYNKQCLFQO-UHFFFAOYSA-N 0.000 description 1
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-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
238000005086 pumping Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical class [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/08—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms
- C07C205/09—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Polyesters Or Polycarbonates (AREA)
Heat Sensitive Colour Forming Recording (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Glass Compositions (AREA)
Iron Core Of Rotating Electric Machines (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Saccharide Compounds (AREA)

DK334788A 1987-06-19 1988-06-17 Fremgangsmåde til fremstilling af 4-substituerede indolin-2-oner, samt mellemprodukter til brug herved DK169965B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8714371		1987-06-19
GB878714371A GB8714371D0 (en)	1987-06-19	1987-06-19	Process

Publications (3)

Publication Number	Publication Date
DK334788D0 DK334788D0 (da)	1988-06-17
DK334788A DK334788A (da)	1988-12-20
DK169965B1 true DK169965B1 (da)	1995-04-18

Family

ID=10619198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK334788A DK169965B1 (da)	1987-06-19	1988-06-17	Fremgangsmåde til fremstilling af 4-substituerede indolin-2-oner, samt mellemprodukter til brug herved

Country Status (25)

Country	Link
US (1)	US4997954A (de)
EP (1)	EP0300614B1 (de)
JP (1)	JPH07596B2 (de)
KR (1)	KR0143088B1 (de)
CN (1)	CN1019296B (de)
AT (1)	ATE93521T1 (de)
AU (1)	AU600582B2 (de)
CA (1)	CA1326035C (de)
CY (1)	CY1951A (de)
DE (1)	DE3883456T2 (de)
DK (1)	DK169965B1 (de)
EG (1)	EG18412A (de)
ES (1)	ES2058285T3 (de)
FI (1)	FI89264C (de)
GB (1)	GB8714371D0 (de)
HK (1)	HK1003226A1 (de)
HU (4)	HU205339B (de)
IE (1)	IE62830B1 (de)
IL (1)	IL86736A (de)
MY (1)	MY103583A (de)
NO (1)	NO172577C (de)
NZ (1)	NZ225072A (de)
PH (1)	PH24608A (de)
PT (1)	PT87770B (de)
ZA (1)	ZA884334B (de)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9008605D0 (en) *	1990-04-17	1990-06-13	Smith Kline French Lab	Process
MX9304801A (es) *	1992-08-06	1997-06-28	Warner Lambert Co	2-toindoles (selenoidoles) disulfuros (seleniduros) relacinados, los cuales inhiben a las proteinas tirosina cinasas y los cuales tienen propiedades anti-tumorales.
US5278162A (en) *	1992-09-18	1994-01-11	The Du Pont Merck Pharmaceutical Company	3,3'-disubstituted-1,3-dihydro-2H-pyrrolo[2,3-b]heterocyclic-2-one useful in the treatment of cognitive disorders of man
GB9300309D0 (en) *	1993-01-08	1993-03-03	Smithkline Beecham Plc	Process
US6218421B1 (en) *	1999-07-01	2001-04-17	Smithkline Beecham P.L.C.	Method of promoting smoking cessation
AR030557A1 (es)	2000-04-14	2003-08-27	Jagotec Ag	Una tableta en multicapa de liberacion controlada y metodo de tratamiento
AU2002222642A1 (en) *	2000-12-14	2002-06-24	Nissan Chemical Industries Ltd.	Method for producing indole derivative
WO2005074387A2 (en) *	2003-12-30	2005-08-18	Sun Pharmaceutical Industries Limited	Novel crystal forms of 4-[2-di-n-propylamino)ethyl]-2 (3h)- indolone hydrochloride
US7378439B2 (en) *	2004-01-20	2008-05-27	Usv, Ltd.	Process for the preparation of 4-(2-dipropylaminoethyl)-1,3-dihydro-2H-indol-2-one hydrochloride
WO2005105741A1 (en) *	2004-02-11	2005-11-10	Sun Pharmaceutical Industries Limited	Substantially pure 4-[2-(di-n-propylamino)ethyl]-2(3h)-indolone hydrochloride
EP1568689A1 (de) *	2004-02-19	2005-08-31	Helm AG	Verfahren zur Herstellung der 2-oxoindol-Derivat, Ropinirole
WO2005080333A1 (en) *	2004-02-19	2005-09-01	Torrent Pharmaceuticals Ltd	Process for purification of ropinirole
BRPI0510260A (pt)	2004-04-27	2007-10-23	Wyeth Corp	método para purificar um composto, e, kit farmacêutico
EP2007721B1 (de)	2006-03-29	2011-07-27	Alembic Limited	Verfahren zur aufreinigung von ropinirolhydrochlorid
US20070254941A1 (en) *	2006-04-21	2007-11-01	Glenmark Pharmaceuticals Limited	Subtantially pure ropinirole hydrochloride, polymorphic form of ropinirole and process for their preparation
CN100457732C (zh) *	2006-05-25	2009-02-04	药源药物化学（上海）有限公司	罗匹尼罗的制备方法
WO2010023693A2 (en) *	2008-09-01	2010-03-04	Lupin Limited	Novel controlled release compositions of ropinirole
US9238025B2 (en)	2009-05-21	2016-01-19	Hisamitsu Pharmaceutical Co., Inc.	Transdermal preparation comprising a ropinirole derivative
US10961194B2 (en)	2017-06-16	2021-03-30	Zhejiang Huahai Licheng Pharmaceutical Co., Ltd.	Method for purifying ropinirole hydrochloride

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4452808A (en) *	1982-12-07	1984-06-05	Smithkline Beckman Corporation	4-Aminoalkyl-2(3H)-indolones
US4588740A (en) *	1982-12-07	1986-05-13	Smithkline Beckman Corporation	Pharmaceutical methods using 4-aminoalkyl-2(3H)-indolones
US4761485A (en) *	1987-03-11	1988-08-02	Pfizer Inc.	Synthetic method for indol-2(3H)-ones

1987
- 1987-06-19 GB GB878714371A patent/GB8714371D0/en active Pending
1988
- 1988-06-13 CA CA000569292A patent/CA1326035C/en not_active Expired - Lifetime
- 1988-06-13 PH PH37063A patent/PH24608A/en unknown
- 1988-06-13 NO NO882588A patent/NO172577C/no not_active IP Right Cessation
- 1988-06-14 IL IL86736A patent/IL86736A/xx not_active IP Right Cessation
- 1988-06-15 US US07/207,351 patent/US4997954A/en not_active Expired - Lifetime
- 1988-06-16 EP EP88305510A patent/EP0300614B1/de not_active Expired - Lifetime
- 1988-06-16 ES ES88305510T patent/ES2058285T3/es not_active Expired - Lifetime
- 1988-06-16 DE DE88305510T patent/DE3883456T2/de not_active Expired - Lifetime
- 1988-06-16 CN CN88103732A patent/CN1019296B/zh not_active Expired
- 1988-06-16 AT AT88305510T patent/ATE93521T1/de not_active IP Right Cessation
- 1988-06-17 NZ NZ225072A patent/NZ225072A/xx unknown
- 1988-06-17 KR KR1019880007283A patent/KR0143088B1/ko not_active Expired - Lifetime
- 1988-06-17 MY MYPI88000674A patent/MY103583A/en unknown
- 1988-06-17 FI FI882919A patent/FI89264C/fi active IP Right Grant
- 1988-06-17 JP JP63151067A patent/JPH07596B2/ja not_active Expired - Lifetime
- 1988-06-17 PT PT87770A patent/PT87770B/pt not_active IP Right Cessation
- 1988-06-17 DK DK334788A patent/DK169965B1/da not_active IP Right Cessation
- 1988-06-17 HU HU911599A patent/HU205339B/hu not_active IP Right Cessation
- 1988-06-17 HU HU883123A patent/HU202200B/hu unknown
- 1988-06-17 HU HU906948A patent/HUT55360A/hu unknown
- 1988-06-17 HU HU893988A patent/HU203723B/hu not_active IP Right Cessation
- 1988-06-17 AU AU18119/88A patent/AU600582B2/en not_active Expired
- 1988-06-17 ZA ZA884334A patent/ZA884334B/xx unknown
- 1988-06-17 IE IE183788A patent/IE62830B1/en not_active IP Right Cessation
- 1988-06-19 EG EG342/88A patent/EG18412A/xx active
1997
- 1997-05-16 CY CY195197A patent/CY1951A/xx unknown
1998
- 1998-03-19 HK HK98102343A patent/HK1003226A1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0300614A1 (de)	1989-01-25
KR890000421A (ko)	1989-03-14
NO172577B (no)	1993-05-03
AU600582B2 (en)	1990-08-16
IL86736A (en)	1992-03-29
FI89264C (fi)	1993-09-10
CN1019296B (zh)	1992-12-02
JPH07596B2 (ja)	1995-01-11
EG18412A (en)	1992-12-30
ZA884334B (en)	1990-04-25
DE3883456T2 (de)	1994-03-17
FI882919A0 (fi)	1988-06-17
NO882588D0 (no)	1988-06-13
HU202200B (en)	1991-02-28
IE62830B1 (en)	1995-03-08
FI89264B (fi)	1993-05-31
PT87770B (pt)	1992-10-30
NZ225072A (en)	1990-05-28
ES2058285T3 (es)	1994-11-01
FI882919L (fi)	1988-12-20
DK334788D0 (da)	1988-06-17
MY103583A (en)	1993-08-28
CY1951A (en)	1997-05-16
NO882588L (no)	1988-12-20
JPS6419065A (en)	1989-01-23
HUT55360A (en)	1991-05-28
DK334788A (da)	1988-12-20
HK1003226A1 (en)	1998-10-16
KR0143088B1 (ko)	1998-07-15
US4997954A (en)	1991-03-05
IE881837L (en)	1988-12-19
HUT48583A (en)	1989-06-28
AU1811988A (en)	1988-12-22
GB8714371D0 (en)	1987-07-22
CA1326035C (en)	1994-01-11
DE3883456D1 (de)	1993-09-30
EP0300614B1 (de)	1993-08-25
PH24608A (en)	1990-08-17
ATE93521T1 (de)	1993-09-15
HU911599D0 (en)	1991-11-28
PT87770A (pt)	1989-05-31
CN1030076A (zh)	1989-01-04
HUT52043A (en)	1990-06-28
HU205339B (en)	1992-04-28
HU203723B (en)	1991-09-30
NO172577C (no)	1993-08-11

Legal Events

Date	Code	Title	Description
1995-04-18	B1	Patent granted (law 1993)
2008-07-07	PUP	Patent expired

Publication	Publication Date	Title
EP0300614B1 (de)	1993-08-25	Verfahren zur Herstellung von substituierten Indolinonderivaten
SU685151A3 (ru)	1979-09-05	Способ получени карбонилзамещенных 1-сульфонилбензимидазолов
HK1003226B (en)	1998-10-16	Process for the preparation of substituted indolinone derivatives
US4110338A (en)	1978-08-29	Product and preparation of 1H-tetrazole-5-thiol derivatives
JP2846042B2 (ja)	1999-01-13	インドールカルボン酸誘導体の製造法
DK2468716T3 (en)	2017-10-02	PROCEDURE FOR THE PREPARATION OF BENDAMUSTIN ALKYL ESTERS, BENDAMUSTIN AND DERIVATIVES OF SAME
KR20180116371A (ko)	2018-10-24	4-알콕시-3-히드록시피콜린산의 제조 방법
EP0008446B1 (de)	1982-09-22	Verfahren zum Herstellen von Carbazolen und darin verwendete Carbazol-Derivate
CA1332948C (en)	1994-11-08	Process for the preparation of substituted quinolines
EP0412529B1 (de)	1994-03-09	Imidazolderivate, Verfahren zu deren Herstellung und diese enthaltende Antiulkusmittel
JP5640283B2 (ja)	2014-12-17	ピリミジン誘導体の調製プロセス
JPH07121931B2 (ja)	1995-12-25	ベンゾ〔ｂ〕フラン誘導体
DK156391B (da)	1989-08-14	Analogifremgangsmaade til fremstilling af 3-aminopyrrolderivater
SU999967A3 (ru)	1983-02-23	Способ получени 6-N-замещенных 6-амино-3-пиридазинилгидразинов или их солей
US5973169A (en)	1999-10-26	Ipriflavone preparation process
US3230234A (en)	1966-01-18	Process for the preparation of 2, 3-dihydro-1h-cyclohepta [b] pyrrole-2, 8-dione derivatives and products thereof
US7238719B2 (en)	2007-07-03	Process for producing 1,2,3-Triazole compounds
Deady et al.	1986	Nucleophilic-Substitution Reactions in Benzo [C][1, 8] Naphthyridines
SU455104A1 (ru)	1974-12-30	Способ получени 2-метил-3-( -алкил -бензимидазолил-2")-этилиндолов
US4185020A (en)	1980-01-22	5-(4-Nitrophenyl)-2-furanmethanamines derivatives
HU207042B (en)	1993-03-01	Process for producing substituted indolinone derivatives
SU730298A3 (ru)	1980-04-25	Способ получени производных имидазола или их солей, или их комплексов с сол ми металлов
CZ296992B6 (cs)	2006-08-16	Príprava a izolace 2-substituovaných-3-pyridylkarboxylových kyselin, jejich karboxylových solí a produktu redukce
GB1570912A (en)	1980-07-09	Aromatic sulphonamido derivatives and process for their manufacture
SU350253A1 (ru)		Т С- -'^-rrvAa«Зандоц АГ>&>& библиотека'МБА (Швейцари )—•*—.—-._«_ lllr"?..,—=^