WO2006118955A3 - Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles - Google Patents

Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles Download PDF

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Publication number
WO2006118955A3
WO2006118955A3 PCT/US2006/016051 US2006016051W WO2006118955A3 WO 2006118955 A3 WO2006118955 A3 WO 2006118955A3 US 2006016051 W US2006016051 W US 2006016051W WO 2006118955 A3 WO2006118955 A3 WO 2006118955A3
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WO
WIPO (PCT)
Prior art keywords
oxindoles
preparing
compounds
thio
disubstituted
Prior art date
Application number
PCT/US2006/016051
Other languages
French (fr)
Other versions
WO2006118955A2 (en
Inventor
Bogdan Kazimierz Wilk
Original Assignee
Wyeth Corp
Bogdan Kazimierz Wilk
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.)
Filing date
Publication date
Application filed by Wyeth Corp, Bogdan Kazimierz Wilk filed Critical Wyeth Corp
Priority to BRPI0608221-1A priority Critical patent/BRPI0608221A2/en
Priority to AU2006242542A priority patent/AU2006242542A1/en
Priority to EP06751659A priority patent/EP1877377A2/en
Priority to JP2008509126A priority patent/JP2008540337A/en
Priority to MX2007013450A priority patent/MX2007013450A/en
Priority to CA002603818A priority patent/CA2603818A1/en
Publication of WO2006118955A2 publication Critical patent/WO2006118955A2/en
Publication of WO2006118955A3 publication Critical patent/WO2006118955A3/en

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    • 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
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/64—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Abstract

Methods for preparing oxindole and thio-oxindole compounds are provided, which compounds are useful as precursors to useful pharmaceutical compounds. Specifically provided are methods for preparing 5-pyrrole-3,3-oxindole compounds and 5-(7-fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-lH-indol-5-yl)-l-methyl-lH-pyrrole-2-carbonitrile. Also provided are methods for preparing iminobenzo[b]thioρhene and benzo[b]thiophenone compounds.
PCT/US2006/016051 2005-04-29 2006-04-27 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles WO2006118955A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BRPI0608221-1A BRPI0608221A2 (en) 2005-04-29 2006-04-27 methods for preparing a compound, and for selectively preparing a nitrile compound, and,
AU2006242542A AU2006242542A1 (en) 2005-04-29 2006-04-27 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
EP06751659A EP1877377A2 (en) 2005-04-29 2006-04-27 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
JP2008509126A JP2008540337A (en) 2005-04-29 2006-04-27 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
MX2007013450A MX2007013450A (en) 2005-04-29 2006-04-27 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles.
CA002603818A CA2603818A1 (en) 2005-04-29 2006-04-27 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US67638105P 2005-04-29 2005-04-29
US60/676,381 2005-04-29

Publications (2)

Publication Number Publication Date
WO2006118955A2 WO2006118955A2 (en) 2006-11-09
WO2006118955A3 true WO2006118955A3 (en) 2007-01-11

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PCT/US2006/016051 WO2006118955A2 (en) 2005-04-29 2006-04-27 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles

Country Status (12)

Country Link
US (1) US7595338B2 (en)
EP (1) EP1877377A2 (en)
JP (1) JP2008540337A (en)
CN (1) CN101166722A (en)
AU (1) AU2006242542A1 (en)
BR (1) BRPI0608221A2 (en)
CA (1) CA2603818A1 (en)
GT (1) GT200600179A (en)
MX (1) MX2007013450A (en)
PE (1) PE20061370A1 (en)
TW (1) TW200716517A (en)
WO (1) WO2006118955A2 (en)

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PE20070220A1 (en) * 2005-07-29 2007-03-19 Wyeth Corp PROCESS FOR THE SYNTHESIS OF PROGESTERONE RECEPTOR MODULATORS
EP2076518A1 (en) * 2006-10-12 2009-07-08 Xenon Pharmaceuticals Inc. Tricyclic spiro-oxindole derivatives and their uses as therapeutic agents
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US20080312306A1 (en) * 2007-06-15 2008-12-18 Wyeth Polymorphs, solvates, and hydrate of 5-(4'-fluoro-2'-oxo-1',2'-dihydrospiro[cyclopropane-1,3'-indol]-5'-yl)-1-methyl-1h-pyrrole-2-carbonitrile
US20080319204A1 (en) * 2007-06-25 2008-12-25 Wyeth Process for the synthesis of progesterone receptor modulators
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US8101647B2 (en) * 2008-10-17 2012-01-24 Xenon Pharmaceuticals Inc. Spiro-oxindole compounds and their use as therapeutic agents
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Also Published As

Publication number Publication date
GT200600179A (en) 2006-11-22
BRPI0608221A2 (en) 2009-11-24
PE20061370A1 (en) 2007-01-08
WO2006118955A2 (en) 2006-11-09
JP2008540337A (en) 2008-11-20
CA2603818A1 (en) 2006-11-09
EP1877377A2 (en) 2008-01-16
AU2006242542A1 (en) 2006-11-09
CN101166722A (en) 2008-04-23
US20060247441A1 (en) 2006-11-02
MX2007013450A (en) 2008-01-21
US7595338B2 (en) 2009-09-29
TW200716517A (en) 2007-05-01

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