PE121599A1 - METHOD FOR PREPARING SUBSTITUTED 4-PHENYL-4-CYANOCICLOHEXANOIC ACIDS - Google Patents

METHOD FOR PREPARING SUBSTITUTED 4-PHENYL-4-CYANOCICLOHEXANOIC ACIDS

Info

Publication number
PE121599A1
PE121599A1 PE1998000955A PE00095598A PE121599A1 PE 121599 A1 PE121599 A1 PE 121599A1 PE 1998000955 A PE1998000955 A PE 1998000955A PE 00095598 A PE00095598 A PE 00095598A PE 121599 A1 PE121599 A1 PE 121599A1
Authority
PE
Peru
Prior art keywords
cr4r5
alkyl
precipitate
compound
halo
Prior art date
Application number
PE1998000955A
Other languages
Spanish (es)
Inventor
Wilford Mendelson
Kevin Webb
Jianhao Chen
Original Assignee
Smithkline Beecham Corp
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 Smithkline Beecham Corp filed Critical Smithkline Beecham Corp
Publication of PE121599A1 publication Critical patent/PE121599A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • 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

Abstract

SE REFIERE A UN METODO PARA SINTETIZAR UN COMPUESTO I, DONDE R1 ES -C(R4R5)nC(O)O(CR4R5)mR6, -(CR4R5)nC(O)NR4(CR4R5)mR6, -(CR4R5)nO(CR4R5)mR6 O -(CR4R5)rR6; m ES 0-2; n ES 1-4; r ES 0-6; R4 Y R5 SON H O ALQUILO C1-C2; R6 ES H, METILO, OH, ARILO; CUANDO R6 ES OH, ENTONCES m ES 2, r ES 2-6; CUANDO R6 ES 2-TETRAHIDROPIRANILO, 2-TETRAHIDROTIOPIRANILO, 2-TETRAHIDROFURANILO, 2-TETRAHIDROTIENILO, ENTONCES m ES 1 o 2; r ES 1-6; CUANDO n ES 1 Y m ES CERO, ENTONCES R6 ES DISTINTO DE H; X ES YR2, HALO, NITRO, NH2 O FORMILAMINA; X2 ES O o NR8; Y ES O o S(O)m`; m' ES 0-2; R2 ES -CH3 o -CH2CH3; R3 ES H, HALO, ALQUILO C1-C4, ENTRE OTROS, R8 ES H o ALQUILO C1-C4; R8' ES R8 o FLUOR; R10 ES OR8 o R11; R11 ES H O ALQUILO C1-C4; Z' ES O, NR9, NOR8, ENTRE OTROS; R' Y R'' SON H o C(O)OX; X ES H o -C(O)OX; X ES H, CATION METALICO o NH4; QUE COMPRENDE a)COMBINAR UN HALURO DE UN METAL DEL GRUPO Ia o IIa (BROMURO DE LITIO O DE MAGNESIO) CON UN COMPUESTO IIa o IIb EN UN DISOLVENTE APROTICO DIPOLAR AMIDICO (DIMETILFORMAMIDA), AGUA; b)CALENTAR LA COMBINACION A 60°C DURANTE VARIAS HORAS, OPCIONALMENTE EN UNA ATMOSFERA INERTE; c)PRECIPITAR UN COMPUESTO I POR ADICION DE UNA BASE FUERTE (HIDROXIDO DE LITIO); d)RETIRAR EL DISOLVENTE AMIDICO Y PURIFICAR EL PRECIPITADO O ACIDULAR EL PRECIPITADO PARA OBTENER EL ACIDO LIBREREFERS TO A METHOD FOR SYNTHESIZING A COMPOUND I, WHERE R1 IS -C (R4R5) nC (O) O (CR4R5) mR6, - (CR4R5) nC (O) NR4 (CR4R5) mR6, - (CR4R5) nO (CR4R5 ) mR6 O - (CR4R5) rR6; m IS 0-2; n ES 1-4; r IS 0-6; R4 AND R5 ARE H OR C1-C2 ALKYL; R6 IS H, METHYL, OH, ARYL; WHEN R6 IS OH, THEN m IS 2, r IS 2-6; WHEN R6 IS 2-TETRAHYDROPYRANYL, 2-TETRAHYDROTIOPYRANYL, 2-TETRAHYDROFURANYL, 2-TETRAHYDROTYHENYL, THEN m IS 1 or 2; r IS 1-6; WHEN n IS 1 AND m IS ZERO, THEN R6 IS DIFFERENT FROM H; X IS YR2, HALO, NITRO, NH2 OR FORMYLAMINE; X2 IS O or NR8; Y IS O or S (O) m`; m 'ES 0-2; R2 is -CH3 or -CH2CH3; R3 IS H, HALO, C1-C4 ALKYL, AMONG OTHERS, R8 IS H or C1-C4 ALKYL; R8 'IS R8 or FLUORINE; R10 IS OR8 or R11; R11 IS H OR C1-C4 ALKYL; Z 'ES O, NR9, NOR8, AMONG OTHERS; R 'Y R' 'ARE H or C (O) OX; X IS H or -C (O) OX; X IS H, CATION METALLIC or NH4; WHICH INCLUDES a) COMBINING A METALLIC HALIDE IN GROUP Ia or IIa (LITHIUM OR MAGNESIUM BROMIDE) WITH A COMPOUND IIa or IIb IN A DIPOLAR APPROXY SOLID AMIDIC (DIMETHYLFORMAMIDE); b) HEATING THE COMBINATION TO 60 ° C FOR SEVERAL HOURS, OPTIONALLY IN AN INERT ATMOSPHERE; c) PRECIPITATE A COMPOUND I BY ADDITION OF A STRONG BASE (LITHIUM HYDROXIDE); d) WITHDRAW THE AMIDIC SOLVENT AND PURIFY THE PRECIPITATE OR ACIDULATE THE PRECIPITATE TO OBTAIN FREE ACID

PE1998000955A 1997-10-10 1998-10-09 METHOD FOR PREPARING SUBSTITUTED 4-PHENYL-4-CYANOCICLOHEXANOIC ACIDS PE121599A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US6161397P 1997-10-10 1997-10-10

Publications (1)

Publication Number Publication Date
PE121599A1 true PE121599A1 (en) 2000-02-19

Family

ID=22036929

Family Applications (1)

Application Number Title Priority Date Filing Date
PE1998000955A PE121599A1 (en) 1997-10-10 1998-10-09 METHOD FOR PREPARING SUBSTITUTED 4-PHENYL-4-CYANOCICLOHEXANOIC ACIDS

Country Status (30)

Country Link
EP (1) EP1043930A4 (en)
JP (1) JP2001519363A (en)
KR (1) KR100560038B1 (en)
CN (1) CN1192025C (en)
AP (1) AP1335A (en)
AR (1) AR015952A1 (en)
AU (1) AU741832B2 (en)
BG (1) BG104302A (en)
BR (1) BR9814064A (en)
CA (1) CA2305614A1 (en)
DZ (1) DZ2619A1 (en)
EA (1) EA003609B1 (en)
HU (1) HUP0003905A3 (en)
ID (1) ID25536A (en)
IL (1) IL135434A (en)
MA (1) MA24670A1 (en)
MY (1) MY122105A (en)
NO (1) NO20001777L (en)
NZ (1) NZ503759A (en)
OA (1) OA11347A (en)
PE (1) PE121599A1 (en)
PL (1) PL191974B1 (en)
SA (1) SA99191000A (en)
SK (1) SK4902000A3 (en)
TR (1) TR200000945T2 (en)
TW (1) TW440557B (en)
UA (1) UA67753C2 (en)
UY (2) UY25201A1 (en)
WO (1) WO1999018793A1 (en)
ZA (1) ZA989228B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9920152D0 (en) * 1999-08-25 1999-10-27 Smithkline Beecham Plc Novel process
WO2001043692A2 (en) * 1999-12-15 2001-06-21 Smithkline Beecham Corporation SALTS OF Cis-4-CYANO-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANE-1-CARBOXYLIC ACID
MXPA02007300A (en) * 2000-01-26 2002-11-29 Smithkline Beecham Corp Monohydrate of cis lithium cyano 4 [3 (cyclopentyloxy) 4 methoxyphenyl]cy clohexanecarboxylate.
EP2258689A1 (en) 2000-03-16 2010-12-08 Biolipox AB Benzylated PDE4 inhibitors
US7250518B2 (en) 2001-01-31 2007-07-31 Pfizer Inc. Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes
MXPA03006885A (en) 2001-01-31 2003-11-13 Pfizer Prod Inc Ether derivatives useful as inhibitors of pde4 isozymes.
EE200300360A (en) 2001-01-31 2003-12-15 Pfizer Products Inc. Biaryl derivatives of nicotinamide used as inhibitors of PDE4 isozymes
JP2004518691A (en) 2001-01-31 2004-06-24 ファイザー・プロダクツ・インク Thiazolyl-, oxazolyl-, pyrrolyl-, and imidazolyl-acid amide derivatives effective as PDE4 isozyme inhibitors
CN102491959B (en) * 2011-12-19 2015-03-25 江苏澄扬作物科技有限公司 Preparation method of oxirane derivative

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4021478A (en) * 1972-07-13 1977-05-03 The Upjohn Company Preparation of carboxylic acids from glycidonitriles with ionic lewis acids
EP0633776B1 (en) * 1992-04-02 2001-05-09 Smithkline Beecham Corporation Compounds useful for treating allergic and inflammatory diseases
US5524438A (en) * 1994-12-15 1996-06-11 United Technologies Corporation Segmented bulkhead liner for a gas turbine combustor
AR012550A1 (en) * 1997-02-12 2000-11-08 Smithkline Beecham Corp METHOD FOR PREPARING SUBSTITUTED 4-PHENYL-4-CIANO-CYCLOHEXANOIC ACIDS AND INTERMEDIATE COMPOUNDS
US6452022B1 (en) * 1997-10-10 2002-09-17 Smithkline Beecham Corporation Method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids

Also Published As

Publication number Publication date
BG104302A (en) 2001-08-31
OA11347A (en) 2003-12-17
TR200000945T2 (en) 2000-10-23
UA67753C2 (en) 2004-07-15
AU9687498A (en) 1999-05-03
AU741832B2 (en) 2001-12-13
EA200000406A1 (en) 2000-10-30
PL191974B1 (en) 2006-07-31
MA24670A1 (en) 1999-07-01
ID25536A (en) 2000-10-12
AP1335A (en) 2004-11-29
BR9814064A (en) 2000-09-26
NO20001777L (en) 2000-05-03
MY122105A (en) 2006-03-31
IL135434A0 (en) 2001-05-20
PL339759A1 (en) 2001-01-02
CA2305614A1 (en) 1999-04-22
UY25524A1 (en) 2000-02-23
CN1275052A (en) 2000-11-29
AP2000001782A0 (en) 2000-06-30
EP1043930A4 (en) 2004-09-15
ZA989228B (en) 1999-04-12
SA99191000A (en) 2005-12-03
KR100560038B1 (en) 2006-03-13
CN1192025C (en) 2005-03-09
WO1999018793A1 (en) 1999-04-22
HUP0003905A3 (en) 2002-01-28
AR015952A1 (en) 2001-05-30
DZ2619A1 (en) 2003-03-08
JP2001519363A (en) 2001-10-23
TW440557B (en) 2001-06-16
SK4902000A3 (en) 2000-11-07
NZ503759A (en) 2002-03-01
EP1043930A1 (en) 2000-10-18
HUP0003905A2 (en) 2001-03-28
NO20001777D0 (en) 2000-04-06
EA003609B1 (en) 2003-06-26
UY25201A1 (en) 2001-08-27
IL135434A (en) 2004-12-15
KR20010015709A (en) 2001-02-26

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