UY25174A1 - Método para la síntesis de derivados de quinolina - Google Patents

Método para la síntesis de derivados de quinolina

Info

Publication number
UY25174A1
UY25174A1 UY25174A UY25174A UY25174A1 UY 25174 A1 UY25174 A1 UY 25174A1 UY 25174 A UY25174 A UY 25174A UY 25174 A UY25174 A UY 25174A UY 25174 A1 UY25174 A1 UY 25174A1
Authority
UY
Uruguay
Prior art keywords
group
alkyl
alkoxy
optionally substituted
ring
Prior art date
Application number
UY25174A
Other languages
English (en)
Inventor
Conrad Kowalski
Mark Mellinger
Joseph Sisko
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
Priority to UY25407A priority Critical patent/UY25407A1/es
Publication of UY25174A1 publication Critical patent/UY25174A1/es

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/36Sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/30Indoles; 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
    • C07D209/32Oxygen atoms
    • C07D209/38Oxygen atoms in positions 2 and 3, e.g. isatin
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C07D215/52Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pulmonology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Esta invención se refiere a nuevos compuestos intermedios y procedimientos para preparar compuestos de quinolina, farmacéuticamente activos, incluida la (-)-(S)-N-(alpa-etilbencil)-3-hidroxi-2-fenilquinolina-4-carboxamida como preferido. Un aspecto de esta invención es un método para preparar compuestos de fórmula (I), o una de sus formas salificadas farmacéuticamente aceptables, en la que: Ar es un grupo fenilo opcionalmente sustituido, un grupo naftilo o cicloalcadienilo, o un grupo heterocíclico de un solo anillo o de anillos condensados, opcionalmente sustituido, que tiene carácter aromático, que contiene de 5 a 12 átomos en el anillo y que comprende hasta 4 heteroátomos en el anillo o en cada uno de ellos, seleccionados entre S, O y N; R es alquilo lineal o ramificado, cicloalquilo, cicloalquilalquilo, fenilo opcionalmente sustituido o un grupo fenilalquilo, un anillo heteroaromático de 5 miembros, opcionalmente sustituido, que comprende hasta 4 heteroátomos seleccionados entre O y N, hidroxialquilo, di-alquil-aminoalquilo, acil-aminoalquilo, alcoxi-alquilo, alquilcarbonilo, carboxi, alcoxi-carbonilo, alcoxi-carbonilalquilo, aminocarbonilo, alquil-aminocarbonilo, di-alquil-aminocarbonilo; ó es un grupo (CH2)p cuando cierra un ciclo con Ar; R1 y R2, son independientemente hidrógeno o alquilo lineal o ramificado, o juntos forman un grupo (CH2)n; ó R1 junto con R forma un grupo (CH2)q; R3 y R4, son independientemente hidrógeno, alquilo lineal o ramificado, alquenilo, arilo, alcoxi, hidroxi, halógeno, nitro, ciano, carboxi, carboxamido, sulfonamido, trifluorometilo, amino, mono- y du-alquilo-amino, O(CH2)r-NT2; O(CH2)s-OW2; ó R4 es un grupo (CH2)t cuando cierra un ciclo con R5 cuando es arilo; R5 es alquilo lineal o ramificado, cicloalquilo, cicloalquilalquilo, arilo. Son antagonistas de NK-3 y son útiles para tratar trastornos pulmonares (asma, enfermedad pulmonar obstructiva crónica, etc), trastornos y picores en la piel (dermatitis, ronchas, etc), trastornos del SNC (Parkinson, Alzheimar, Huntington, convulsiones, epilepsia), trastornos de la alimentación, incontinencia urinaria, entre otras.
UY25174A 1997-09-17 1998-09-08 Método para la síntesis de derivados de quinolina UY25174A1 (es)

Priority Applications (1)

Application Number Priority Date Filing Date Title
UY25407A UY25407A1 (es) 1997-09-17 1999-02-26 Método para la síntesis de (-)-(s)-n-(alpha-etilbencil)-3-hidroxi-2-fenilquinolina-4-carboxamida

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US5930397P 1997-09-17 1997-09-17

Publications (1)

Publication Number Publication Date
UY25174A1 true UY25174A1 (es) 2001-07-31

Family

ID=22022126

Family Applications (2)

Application Number Title Priority Date Filing Date
UY25174A UY25174A1 (es) 1997-09-17 1998-09-08 Método para la síntesis de derivados de quinolina
UY25407A UY25407A1 (es) 1997-09-17 1999-02-26 Método para la síntesis de (-)-(s)-n-(alpha-etilbencil)-3-hidroxi-2-fenilquinolina-4-carboxamida

Family Applications After (1)

Application Number Title Priority Date Filing Date
UY25407A UY25407A1 (es) 1997-09-17 1999-02-26 Método para la síntesis de (-)-(s)-n-(alpha-etilbencil)-3-hidroxi-2-fenilquinolina-4-carboxamida

Country Status (32)

Country Link
US (6) US6335448B1 (es)
EP (1) EP1017676B1 (es)
JP (1) JP2001516744A (es)
KR (1) KR20010024031A (es)
CN (1) CN1125815C (es)
AP (1) AP1201A (es)
AR (1) AR015445A1 (es)
AT (1) ATE353879T1 (es)
AU (1) AU744538B2 (es)
BG (1) BG104243A (es)
BR (1) BR9812085A (es)
CA (1) CA2303026A1 (es)
DE (1) DE69837100T2 (es)
DZ (1) DZ2607A1 (es)
EA (1) EA002633B1 (es)
ES (1) ES2283072T3 (es)
HU (1) HUP0004855A3 (es)
ID (1) ID24140A (es)
IL (1) IL134991A0 (es)
MA (1) MA24644A1 (es)
MY (1) MY120237A (es)
NO (1) NO314303B1 (es)
NZ (1) NZ503307A (es)
OA (1) OA11340A (es)
PE (1) PE129299A1 (es)
PL (1) PL339340A1 (es)
SK (1) SK3672000A3 (es)
TR (1) TR200000720T2 (es)
TW (1) TW509678B (es)
UY (2) UY25174A1 (es)
WO (1) WO1999014196A1 (es)
ZA (1) ZA988455B (es)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AP1201A (en) * 1997-09-17 2003-09-01 Smithkline Beecham Corp Method for the synthesis of quinoline derivatives.
CA2368455A1 (en) 1999-03-29 2000-10-05 Neurogen Corporation 4-substituted quinoline derivatives as nk-3 and/or gaba(a) receptor ligands
JP2007520543A (ja) 2004-02-04 2007-07-26 ファイザー・プロダクツ・インク 置換キノリン化合物
AU2006253054A1 (en) * 2005-06-03 2006-12-07 Astrazeneca Ab Quinoline derivatives as NK3 anatgonists
WO2007016609A2 (en) * 2005-08-02 2007-02-08 Smithkline Beecham Corporation Method for the synthesis of quinoliνe derivatives
JP2009504642A (ja) * 2005-08-11 2009-02-05 アストラゼネカ・アクチエボラーグ Nk−3受容体の調節剤としてのオキソピリジルキノリンアミド
AR057130A1 (es) * 2005-09-21 2007-11-14 Astrazeneca Ab Quinolinas de alquilsulfoxido y una composicion farmaceutica
US20080234269A1 (en) * 2005-09-21 2008-09-25 Astrazeneca Ab N-Oxo-Heterocycle and N-Oxo-Alkyl Quinoline-4-Carboxamides as Nk-3 Receptor Ligands
WO2007086799A1 (en) * 2006-01-27 2007-08-02 Astrazeneca Ab Amide substituted quinolines
CN102702099A (zh) * 2012-06-21 2012-10-03 江苏恩华药业股份有限公司 (s)-3-羟基-2-苯基-n-(1-苯基丙基)喹啉-4-甲酰胺的制备方法
CN102924375B (zh) * 2012-06-21 2015-02-18 江苏恩华药业股份有限公司 Talnetant中间体及其制备方法和应用
CN103214416A (zh) * 2013-04-26 2013-07-24 扬州大学 一种合成多取代喹啉类化合物的方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2776290A (en) * 1957-01-01 Hydroxy cevchoninates and carboxylic
PT940391E (pt) * 1994-05-27 2004-12-31 Glaxosmithkline Spa Derivados de quinolina como antagonistas do receptor de taquicinina nk3
US5627193A (en) * 1995-02-09 1997-05-06 Mitsui Toatsu Chemicals, Inc. Quinoline-4-carbonylguanidine derivatives, process for producing the same and pharmaceutical preparations containing the compounds
AP1201A (en) * 1997-09-17 2003-09-01 Smithkline Beecham Corp Method for the synthesis of quinoline derivatives.

Also Published As

Publication number Publication date
AR015445A1 (es) 2001-05-02
BR9812085A (pt) 2000-09-26
PE129299A1 (es) 2000-02-19
HUP0004855A3 (en) 2001-08-28
CN1278796A (zh) 2001-01-03
SK3672000A3 (en) 2000-09-12
ID24140A (id) 2000-07-06
AP2000001767A0 (en) 2000-03-31
OA11340A (en) 2003-12-09
DE69837100D1 (de) 2007-03-29
US20050171152A1 (en) 2005-08-04
EA002633B1 (ru) 2002-08-29
KR20010024031A (ko) 2001-03-26
ZA988455B (en) 1999-02-17
US20020038029A1 (en) 2002-03-28
JP2001516744A (ja) 2001-10-02
NO20001387D0 (no) 2000-03-16
US20040049031A1 (en) 2004-03-11
UY25407A1 (es) 1999-11-17
EP1017676B1 (en) 2007-02-14
AU744538B2 (en) 2002-02-28
US6335448B1 (en) 2002-01-01
EA200000322A1 (ru) 2000-10-30
PL339340A1 (en) 2000-12-18
DZ2607A1 (fr) 2003-03-01
ES2283072T3 (es) 2007-10-16
TR200000720T2 (tr) 2000-08-21
CA2303026A1 (en) 1999-03-25
NO20001387L (no) 2000-03-16
BG104243A (en) 2001-05-31
US20020173657A1 (en) 2002-11-21
CN1125815C (zh) 2003-10-29
WO1999014196A1 (en) 1999-03-25
NO314303B1 (no) 2003-03-03
MY120237A (en) 2005-09-30
US20060189809A1 (en) 2006-08-24
EP1017676A4 (en) 2002-12-04
IL134991A0 (en) 2001-05-20
EP1017676A1 (en) 2000-07-12
NZ503307A (en) 2002-04-26
MA24644A1 (fr) 1999-04-01
ATE353879T1 (de) 2007-03-15
DE69837100T2 (de) 2007-11-22
AU9395898A (en) 1999-04-05
HUP0004855A2 (hu) 2001-06-28
TW509678B (en) 2002-11-11
AP1201A (en) 2003-09-01

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Legal Events

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Effective date: 20121220