FI93952B - Förfarande för framställning av farmakologiskt aktiva 4-amino-3-acylkinolinderivat samt nya mellanprodukter - Google Patents

Förfarande för framställning av farmakologiskt aktiva 4-amino-3-acylkinolinderivat samt nya mellanprodukter Download PDF

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Publication number
FI93952B
FI93952B FI895048A FI895048A FI93952B FI 93952 B FI93952 B FI 93952B FI 895048 A FI895048 A FI 895048A FI 895048 A FI895048 A FI 895048A FI 93952 B FI93952 B FI 93952B
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FI
Finland
Prior art keywords
methylphenylamino
quinoline
butyryl
formula
preparation
Prior art date
Application number
FI895048A
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English (en)
Finnish (fi)
Other versions
FI895048A0 (sv
FI93952C (sv
Inventor
Robert John Ife
Thomas Henry Brown
Colin Andrew Leach
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Smithkline Beckman Intercredit
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Publication date
Application filed by Smithkline Beckman Intercredit filed Critical Smithkline Beckman Intercredit
Publication of FI895048A0 publication Critical patent/FI895048A0/sv
Application granted granted Critical
Publication of FI93952B publication Critical patent/FI93952B/sv
Publication of FI93952C publication Critical patent/FI93952C/sv

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic 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
    • C07D215/16—Heterocyclic 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic 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
    • C07D215/16—Heterocyclic 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
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic 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
    • C07D215/16—Heterocyclic 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (10)

1. Förfarande för framställning av en farmakologiskt aktiv förening med formeln (I) NH 0
15 R3 väri R1 är C,.6alkyl, C3_6cykloalkyl eller C3j6cykloalkyl-C,.6alkyl; R2 är väte, C^alkyl, C^alkoxi, amino, C,.6alkyltio, halogen, 20 cyano, hydroxi, karbamoyl, karboxi, C^alkanoyl eller tri-fluormetyl; m är 1, 2 eller 3;
2. R3 är hydroxi - C].6alkyl, C^alkoxi-Chalky 1, hydroxi-C,_6alkoxi, C^alkoxi-C^alkoxi, hydroxi-C^alkoxi-C^alkoxi eller hydroxi-C^alkoxi - C,^alkoxi - C^alkoxi; eller ett sait därav, kännetecknat av att 30 (a) en förening med formeln (II) omsättes med en förening med formeln (III) roiY-' {R2)m
40 R3' (ID (III) 44 93952 där R1, R2 och m har ovan angiven betydelse, R3' är en even-tuellt skyddad grupp R3 och X är en grupp som kan ersättas med en amin; eller 5 b) en förening med formeln (VII) --O X? NR1 0 ^ 1 II (VII) XXXW/ ^ R1 15 HO alkyleras, där R1, R2 och m har ovan angiven betydelse och R1 20 är väte eller en kväveskyddsgrupp; och därefter om sä önskas i) avlägsnas en eventuell skyddsgrupp; ii) en grupp R1 omvandlas tili en annan grupp R1; iii) en grupp R3 omvandlas tili en annan grupp R3; 25 iv) bildas ett sait.
2. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en forening med formeln (I) väri m är 1 och gruppen R2 finns i ringens 2-ställning, 30
3. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en förening med formeln (I) väri tvä R2-grupper finns i ringens 2- och 4-ställningar. 35 4. Förfarande enligt patentkrav 2 eller 3, kännetecknat av att man framställer en förening med formeln (I) väri gruppen R3 finns i kinolinringens 8-ställning. Il Förfarande enligt patentkrav 4, kännetecknat av att man 40 framställer en förening med formeln (I) väri gruppen R3 är en ; hydroxi-C,.6alkyl- eller C^alkoxi-Cj^alkoxigrupp. 93952 45
6. Förfarande enligt patentkrav 1, kannetecknat av att man framställer 3-butyryl-4-(2-metylfenylamino)-8-(hydroximetyl)kinolin, 3-butyryl-4-(2-metylfenylamino)-8-(2-metoxietoxi)kinolin, 5 3-butyryl-4-(4-hydroxi-2-metylfenylamino)-8-(hydroximetyl)-kinolinhydroklorid, 3-butyryl-4-(2-metylfenylamino)-8-(1-hydroxietyl)kinolin, 3-butyryl-4-(2-metylfenylamino)-6-(hydroxietyl)kinolin, 3-butyryl-4-(2-metylfenylamino)-7-(hydroximetyl)kinolin, 10 3-isobutyryl-4 -(2-metylfenylamino)-8-(hydroximetyl)kinolin, 3-isobutyryl-4-(4-fluor-2-metylfenylamino)-8-(hydroximetyl)-kinolin, 3-butyryl-4-(4-fluor-2-metylfenylamino)-8-(hydroximetyl)-kinolin, 15 3-butyryl-4-(2-metylfenylamino)-8-(2-hydroxietoxi)kinolin, 3-butyryl-4-(2-metylfenylamino)-8-(2-(2-hydroxietoxi)etoxi)-kinolin, 3-butyryl-4-(2-metylfenylamino)-8-(2-(2-(2-hydroxietoxi)etoxi) etoxi)kinolin, 20 3-butyryl-4-(4 - fluor-2-metylfenylamino)-8-(2-(2-hydroxietoxi) etoxi)kinolin, 3-butyryl-4-(4-fluor-2-metylfenylamino)-8-(2-hydroxietoxi)-kinolin, 3-butyryl-4-(4-hydroxi-2-metylfenylamino)-8-(1-hydroxietyl)-25 kinolin, 3-isobutyryl-4-(4-hydroxi-2-metylfenylamino)-8-(hydroximetyl) kinolinhydroklorid, 3-butyryl-4-(4-fluor-2-metylfenylamino)-8-(2-metoxietoxi)-kinolin, 30 3-isobutyryl-4-(2-metylfenylamino)-8-(2-hydroxietoxi)kino lin, 3-isobutyryl-4-(4-fluor-2-metylfenylamino)-8-(2-hydroxietoxi) kinolin, 3-isobutyryl-4-(2-metylfenylamino)-8-(2-metoxietoxi)kinolin, 35 3-propanoyl-4-(2-metylfenylamino)-8-(2-hydroxietoxi)kinolin, eller 3-propanoyl-4-(4-fluor-2-metylfenylamino)-8-(2-hydroxietoxi) kinolin, eller ett sait därav. 93952 46
7. Förening med formeln (II) X 0 Q (II> R3’ 10 väri R1 är sasom definierats i formeln (I) i patentkrav 1, R3’ är sasom definierats för R3 i formeln (I) eller den utgö-res av bensoyloximetyl eller 4-metoxibensoyloximetyl och X är klor. 15
8. Förening med formeln (VII) 20 ^ NR5 0 J II 1 (VII) 25 rpiY" HO 30 väri R1, R2 och m är säsom definierats i formeln (I) i patentkrav l och R5 är väte.
FI895048A 1988-02-25 1989-10-24 Förfarande för framställning av farmakologiskt aktiva 4-amino-3-acylkinolinderivat samt nya mellanprodukter FI93952C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB888804444A GB8804444D0 (en) 1988-02-25 1988-02-25 Compounds
GB8804444 1988-02-25
PCT/EP1989/000175 WO1989008104A1 (en) 1988-02-25 1989-02-20 4-amino-3-acylquinoline derivatives and their use as inhibitors of gastric secretion
EP8900175 1989-02-20

Publications (3)

Publication Number Publication Date
FI895048A0 FI895048A0 (sv) 1989-10-24
FI93952B true FI93952B (sv) 1995-03-15
FI93952C FI93952C (sv) 1995-06-26

Family

ID=10632376

Family Applications (1)

Application Number Title Priority Date Filing Date
FI895048A FI93952C (sv) 1988-02-25 1989-10-24 Förfarande för framställning av farmakologiskt aktiva 4-amino-3-acylkinolinderivat samt nya mellanprodukter

Country Status (22)

Country Link
US (1) US5089504A (sv)
EP (1) EP0330485B1 (sv)
JP (1) JPH0774204B2 (sv)
KR (1) KR0159083B1 (sv)
CN (2) CN1027368C (sv)
AU (1) AU606508B2 (sv)
CA (1) CA1332839C (sv)
CZ (1) CZ398391A3 (sv)
DE (1) DE68906687T2 (sv)
DK (1) DK166623B1 (sv)
ES (1) ES2055037T3 (sv)
FI (1) FI93952C (sv)
GB (1) GB8804444D0 (sv)
HU (1) HU208814B (sv)
IE (1) IE63239B1 (sv)
IL (1) IL89346A (sv)
MY (1) MY105158A (sv)
NZ (1) NZ228098A (sv)
PT (1) PT89789B (sv)
WO (1) WO1989008104A1 (sv)
ZA (1) ZA891402B (sv)
ZW (1) ZW1989A1 (sv)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8918265D0 (en) * 1989-08-10 1989-09-20 Smithkline Beckman Intercredit Compounds
US5215999A (en) * 1990-03-28 1993-06-01 Otsuka Pharmaceutical Co., Ltd. Quinoline derivative and antiulcer agent containing said quinoline derivative
MX9200338A (es) * 1991-01-29 1992-12-01 Smithkline Beecham Intercredit Sales de compuestos de quinolina y composiciones farmaceuticas que las contienen
GB9126438D0 (en) * 1991-12-12 1992-02-12 Smithkline Beecham Intercredit New quinoline derivatives
US5362743A (en) * 1993-03-09 1994-11-08 Pfizer Inc. Aminoquinoline derivatives
IS4164A (is) * 1993-06-11 1994-12-12 Ab Astra Efnasambönd sem hindra flæði magasýru
SE9302005D0 (sv) 1993-06-11 1993-06-11 Ab Astra New active compounds
US5556863A (en) * 1993-06-11 1996-09-17 Astra Aktiebolag Compound for gastric acid secretion inhibition
EP1086094A1 (en) * 1998-05-23 2001-03-28 Byk Gulden Lomberg Chemische Fabrik GmbH Quinoline-aminomethyl-pyridyl derivatives with anti-helicobacter activity
US6852739B1 (en) 1999-02-26 2005-02-08 Nitromed Inc. Methods using proton pump inhibitors and nitric oxide donors
HN2000000203A (es) 1999-11-30 2001-06-13 Pfizer Prod Inc Procedimiento para la obtencion de 1,2,3,4-tetrahidroquinolinas 4-carboxiamino-2- sustituidas.
UA80393C2 (uk) 2000-12-07 2007-09-25 Алтана Фарма Аг Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці
WO2003043614A2 (en) * 2001-11-19 2003-05-30 Altana Pharma Ag Reversible proton pump inhibitors for the treatment of airway disorders
MY140561A (en) * 2002-02-20 2009-12-31 Nycomed Gmbh Dosage form containing pde 4 inhibitor as active ingredient
US7211590B2 (en) 2002-08-01 2007-05-01 Nitromed, Inc. Nitrosated proton pump inhibitors, compositions and methods of use
PT1606261E (pt) 2003-03-10 2010-01-11 Nycomed Gmbh Novo processo para a preparação de roflumilast
EP1974730A1 (en) 2003-11-03 2008-10-01 AstraZeneca AB Imidazo[1,2-a]pyridine derivatives for use in the treatment of sleep disturbance due to silent gastro-esophageal reflux
CA2601250C (en) * 2005-03-16 2014-10-28 Nycomed Gmbh Taste masked dosage form containing roflumilast
CN106496119A (zh) * 2016-10-17 2017-03-15 江南大学 一种n‑苯基‑8‑氨基喹啉的制备方法

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Publication number Priority date Publication date Assignee Title
US2652398A (en) * 1949-11-17 1953-09-15 Endo Products Inc N-substituted-2-amino (methyl) quinolines
US3470186A (en) * 1967-06-02 1969-09-30 American Cyanamid Co Substituted 4-anilino-3-quinolinecarboxylic acids and esters
CA942748A (en) * 1970-09-18 1974-02-26 Venkatachala L. Narayanan 1-aziridinylcarbonyl substituted-3-quinolinecarboxylic acid compounds
US4343804A (en) * 1979-03-26 1982-08-10 A. H. Robins Company, Inc. 4-Amino-3-quinolinecarboxylic acids and esters-antisecretory anti-ulcer compounds
ZA801526B (en) * 1979-03-26 1981-08-26 Robins Co Inc A H 4-amino-3-quinolinecarboxylic acids and esters-antisecretory, anti-ulcer compounds
GB8621425D0 (en) * 1986-09-05 1986-10-15 Smith Kline French Lab Compounds
GB8804446D0 (en) * 1988-02-25 1988-03-23 Smithkline Beckman Intercredit Compounds
GB8804443D0 (en) * 1988-02-25 1988-03-23 Smithkline Beckman Intercredit Compounds
GB8804445D0 (en) * 1988-02-25 1988-03-23 Smithkline Beckman Intercredit Compounds

Also Published As

Publication number Publication date
IL89346A (en) 1994-01-25
EP0330485A1 (en) 1989-08-30
JPH02503318A (ja) 1990-10-11
PT89789B (pt) 1994-05-31
DK528889D0 (da) 1989-10-24
CZ398391A3 (en) 1994-05-18
KR0159083B1 (ko) 1998-12-01
NZ228098A (en) 1990-10-26
WO1989008104A1 (en) 1989-09-08
FI895048A0 (sv) 1989-10-24
GB8804444D0 (en) 1988-03-23
US5089504A (en) 1992-02-18
PT89789A (pt) 1989-10-04
MY105158A (en) 1994-08-30
EP0330485B1 (en) 1993-05-26
ES2055037T3 (es) 1994-08-16
JPH0774204B2 (ja) 1995-08-09
CN1100414A (zh) 1995-03-22
ZW1989A1 (en) 1989-09-13
DE68906687D1 (de) 1993-07-01
IE890568L (en) 1989-08-25
DK166623B1 (da) 1993-06-21
HU891463D0 (en) 1990-01-28
DK528889A (da) 1989-10-24
CN1035501A (zh) 1989-09-13
AU3181989A (en) 1989-09-22
HU208814B (en) 1994-01-28
DE68906687T2 (de) 1993-12-02
FI93952C (sv) 1995-06-26
CA1332839C (en) 1994-11-01
KR900700457A (ko) 1990-08-13
AU606508B2 (en) 1991-02-07
ZA891402B (en) 1990-09-26
HUT53086A (en) 1990-09-28
IE63239B1 (en) 1995-04-05
CN1027368C (zh) 1995-01-11

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Owner name: SMITHKLINE BECKMAN INTERCREDIT B.V.