FI111631B - Förfarande för framställning av terapeutiskt användbara 4-anilinokinazolinderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara 4-anilinokinazolinderivat Download PDF

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Publication number
FI111631B
FI111631B FI930208A FI930208A FI111631B FI 111631 B FI111631 B FI 111631B FI 930208 A FI930208 A FI 930208A FI 930208 A FI930208 A FI 930208A FI 111631 B FI111631 B FI 111631B
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Finland
Prior art keywords
alkyl
alkoxy
amino
mixture
quinazoline
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FI930208A
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English (en)
Finnish (fi)
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FI930208A (fi
FI930208A0 (fi
Inventor
Andrew John Barker
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Astrazeneca Ab
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Priority claimed from GB929201095A external-priority patent/GB9201095D0/en
Priority claimed from GB929213572A external-priority patent/GB9213572D0/en
Priority claimed from GB929223735A external-priority patent/GB9223735D0/en
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of FI930208A0 publication Critical patent/FI930208A0/fi
Publication of FI930208A publication Critical patent/FI930208A/fi
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Publication of FI111631B publication Critical patent/FI111631B/sv

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

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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)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Claims (4)

1. Förfarande för framställning av ny a, tera-peutiskt användbara 4-anilinokinazolinderivat med formeln 5 I { rZ>" 10 I I H—(Rl,m ΛΛ/ 15 i vilken m är 1, 2 eller 3 och varje R1 är oberoende hydr-oxi, amino, karboxi, karbamoyl, ureido, (l-4C)alkoxikar-bonyl, N-(l-4C)alkylkarbamoyl, M,Jä-di-[(l-4C)alkyl]karbamoyl, hydroxiamino, trifluormetoxi, (l-4C)alkyl, (l-4C)al-20 koxi, (l-3C)alkylendioxi, (l-4C)alkylamino, di-[(l-4C)al- kyl]amino, pyrrolidin-1-yl, piperidino, morfolino, pipe-razin-l-yl, 4-(l-4C)alkylpiperazin-l-yl, (l-4C)alkyltio, halogen(1-4c)alkyl (av annat slag än trifluormetyl), hyd-roxi(1-4C)alkyl, (l-4C)alkoxi-(l-4C)alkyl, amino-(l-4C)al-25 kyl, (l-4C)alkylamino-(1-4C)alkyl, di-[1-4C)alkyl]amino- ( 1-4C) alkyl, piperidino-(1-4C)alkyl, morfolino- (l-4C)alkyl, piperazin-l-yl-(l-4C)alkyl, 4-(l-4C)alkylpi-perazin-l-yl-(l-4C)alkyl, hydroxi-(2-4C)alkoxi-(1-4C) alkyl, (l-4C)alkoxi-(2-4C)alkoxi-(l-4C)alkyl, (l-4C)alkyl-30 tio-(1-4CJalkyl, hydroxi(2-4C)alkyltio-(l-4C)alkyl, anili- ... no-( 1-4C) alkyl, fenyltio-( l-4C)alkyl, cyano-( 1-4C) alkyl, halogen(2-4C)alkoxi, hydroxi-(2-4C)alkoxi, (l-4C)alkoxi-(2-4C)alkoxi, karboxi-(l-4C)alkoxi, (l-4c)alkoxikarbo-nyl-(l-4C)alkoxi, karbamoyl-(l-4C)alkoxi, amino-(2-4C)-35 alkoxi, (l-4C)alkylamino-(2-4C)alkoxi, di-[(l-4C)alkyl]- 108 111631 amino-(2-4C)alkoxi, (l-4C)alkoxi-(2-4C)alkanoyloxi, fenyl-(l-4C)alkoxi, anilino-(2-4C)alkoxi, piperidino-(2-4C)alkoxi, morfolino-(2-4C)alkoxi, piperazin-l-yl-(2-4C)alkoxi, 4-(1-4C)alkylpiperazin-l-yl-(2-4C)alkoxi, 5 hydroxi-(2-4C)alkylamino, (l-4C)alkoxi-(2-4C)alkylamino, amino-(2-4C)alkylamino,(1-4C)alkylamino-(2-4C)alkylamino, di-[(1-4C)alkyl]amino-(2-4C)alkylamino, fenyl-(1-4C)alky-lamino, (2-4C)alkanoylamino, bensamido, bensensulfonamido, 3- fenylureido, 2-oxopyrrolidin-l-yl, 2,5-dioxopyrroli- 10 din-l-yl, halogen(2-4C)alkanoylamino, hydroxi-(2-4C)al- kanoylamino, (l-4C)alkoxi-(2-4C)alkanoylamino, (l-4C)alk-oxikarbonyl-(2-4C)alkanoylamino, amino-(2-4C)alkanoylami-no, (l-4C)alkylamino-(2-4C)alkanoylamino eller di-(1-4C)alkyl]amino-(2-4C)alkanoylamino; 15 n är 1 eller 2; och varje R2 är oberoende väte, hydroxi, halogen, trifluor-metyl, amino, nitro, cyano, (l-4C)alkyl eller (l-4C)alk-oxi; eller terapeutiskt acceptabla salter därav; 20 med undantag av att 4- (4'-hydroxianilino)-6-metoxikinazolin, 4-(4'-hydroxianilino)-6,7-metylendioxikinazolin, 4-(4'-hydroxianilino)-6,7,8-trimetoxikinazolin, 6-amino-4-(4'-aminoanilino)kinazolin, .. 25 4-anilino-6-metylkinazolin och hydrokloridsaltet därav och 4-anilino-6,7-dimetoxikinazolin och hydrokloridsaltet därav, 4-(4'-metoxianilino)-8-metoxikinazolin, 4-(4'-kloranilino)-8-metoxikinazolin, 30 8-hydroxi-4-(4'-metoxianilinoJkinazolin och 4-(4’-kloranilino)-8-hydroxikinazolin är exkluderade, kännetecknatav att (a) en kinazolin med formeln III 35 2 109 111631
5 JL j—(Rl^ i vilken Z är en utbytbar grupp, omsätts med en anilin med 10 formeln IV ( R2 )„ IV 15 (b) för framställning av sädana förenlngar med formeln I, i vilken R1 eller R2 är hydroxi, avspjälks ett ki- 20 nazolinderivat med formeln I, i vilken R1 eller R2 är (l-4C)alkoxi; (c) för framställning av sädana föreningar med formeln I, i vilken R1 ä amino, reduceras ett kinazolinderivat med formeln I, i vilken R1 är nitro: ... 25 (d) för framställning av sädana föreningar med for meln I, i vilken R1 är (2-4C)alkanoylamino eller substi-tuerad (2-4C)alkanoylamino, ureido, 3-fenylureido eller bensamido, acyleras av ett kinazolinderivat med formeln I, i vilken R1 är amino: 30 (e) för framställning av sädana föreningar med for meln I, i vilken R1 är (l-4C)alkoxi eller substituerad (l-4C)alkoxi eller R1 är (1-4C)alkylamino eller substituerad (l-4C)alkylamino, alkyleras av ett kinazolinderivat med formeln I, i vilken R1 är hydroxi eller amino, allt 35 efter vad som är lämpligt; 111631 110 ( f) för framställning av sädana föreningar med for-meln I, i vilken R1 är en karboxisubstituent eller en substituent som innehäller en karboxigrupp, hydrolyseras av ett kinazolinderivat med formeln I, i vilken R1 är en 5 (l-4c)alkoxikarbonylsubstituent eller en substituent som innehäller en (l-4c)alkoxikarbonylgrupp; eller (g) för framställning av sädana föreningar med formeln I, i vilken R1 är en amino-, oxi-, tio- eller cyanosubstituerad (l-4C)alkylsubstituent, omsätts av ett 10 kinazolinderivat med formeln I, i vilken R1 är en (l-4C)al-kylsubstituent som bär en utbytbar grupp, med en lämplig amin, alkohol, tiol eller cyanid; och dä önskas, ett kinazolinderivat med formeln I överförs tili ett farmaceutiskt acceptabelt sait genom att 15 föreningen med formeln I bringas att reagera med en lämplig syra med användning av en konventionell procedur.
2. Förfarande enligt patentkrav 1, k ä n n e -tecknat av att det framställs ett 4-anilinokinazo-linderivat med formeln I, där (R1 -)m är 6-hydroxi, 7-hydr-20 oxi, 6,7-dihydroxi, 6-amino, 7-amino, 6-ureido 6-trifluor-metoxi, 6-metyl, 6,7-dimetyl, 6-metoxi, 7-metoxi, 6,7-di-metoxi, 6,7-dietoxi, 6-hydroxi-7-metoxi, 7-hydroxi-6-metoxi, 6-amino-7-metoxi, 6-amino-7-metyltio, 5-amino-6,7-di-metoxi, 6-metoxi-7-isopropoxi, 6,7-metylendioxi, 6,7-ety-.. 25 lendioxi, 6-dimetylamino, 6-metoximetyl, 6-(2-metoxietoxi- metyl), 6-cyanometyl, 7-(2-hydroxietoxi)-6-metoxi, 6,7-di-(2-hydroxietoxi), 6-(2-metoxietoxi), 6-metoxi-7-(2-met- oxietoxi), 6,7-di-(2-metoxietoxi), 7-(2-brometoxi)-6-met-oxi, 7-bensyloxi-6-metoxi, 6-(2-metoxietylamino), 6-acet-30 amido, 6-(2-kloracetamido), 6-(2-metoxiacetamido) eller 7-(2-metoxiacetamido), och (R2)n är väte, 4'-fluor, 3'-klor, 3'-brom, 3',4'-diklor, 4'-fluor-3'-klor, 3'-tri-fluormetyl, 4'-fluoro-3'trifluormetyl, 3'-nitro, 3'-nit-ro-4'-klor, 3'-nitro-4'-fluor eller 3'-metyl; 35 eller ett farmaceutiskt acceptabelt syraadditionssalt därav. 111631 111 ö
3. Förfarande enligt patentkrav 1, k ä n n e -tecknat av att 4-(3'-klor-4'-fluoranilino)-6,7-di-metoxikinazolin framställs.
4. Förfarande enligt patentkrav 1, k ä n n e - 5 tecknat av att 4-(3,-bromanilino)-6,7-dimetoxi-kinazolin framställs.
FI930208A 1992-01-20 1993-01-19 Förfarande för framställning av terapeutiskt användbara 4-anilinokinazolinderivat FI111631B (sv)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB9201095 1992-01-20
GB929201095A GB9201095D0 (en) 1992-01-20 1992-01-20 Quinazoline derivatives
GB9213572 1992-06-26
GB929213572A GB9213572D0 (en) 1992-06-26 1992-06-26 Quinazoline derivatives
GB9223735 1992-11-12
GB929223735A GB9223735D0 (en) 1992-11-12 1992-11-12 Quinazoline derivatives

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FI930208A0 FI930208A0 (fi) 1993-01-19
FI930208A FI930208A (fi) 1993-07-21
FI111631B true FI111631B (sv) 2003-08-29

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FI930208A FI111631B (sv) 1992-01-20 1993-01-19 Förfarande för framställning av terapeutiskt användbara 4-anilinokinazolinderivat

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US (2) US5457105A (sv)
EP (1) EP0566226B1 (sv)
KR (1) KR100229294B1 (sv)
AT (1) ATE130000T1 (sv)
AU (1) AU661533B2 (sv)
CA (1) CA2086968C (sv)
CZ (1) CZ282038B6 (sv)
DE (1) DE69300754T2 (sv)
DK (1) DK0566226T3 (sv)
ES (1) ES2078798T3 (sv)
FI (1) FI111631B (sv)
GB (1) GB9300059D0 (sv)
GR (1) GR3018143T3 (sv)
HK (1) HK36497A (sv)
HU (2) HU221622B1 (sv)
IL (1) IL104479A (sv)
NO (1) NO301541B1 (sv)
NZ (1) NZ245662A (sv)
RU (1) RU2127263C1 (sv)
SK (1) SK281551B6 (sv)
TW (1) TW283146B (sv)
UA (1) UA34426C2 (sv)

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