FI105548B - Förfarande för framställning av farmaceutiskt aktiva 1,3-dihydro-2H-imidazo(4,5-b)kinolin-2-oner - Google Patents

Förfarande för framställning av farmaceutiskt aktiva 1,3-dihydro-2H-imidazo(4,5-b)kinolin-2-oner Download PDF

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Publication number
FI105548B
FI105548B FI942010A FI942010A FI105548B FI 105548 B FI105548 B FI 105548B FI 942010 A FI942010 A FI 942010A FI 942010 A FI942010 A FI 942010A FI 105548 B FI105548 B FI 105548B
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FI
Finland
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formula
alkyl
optionally substituted
dihydro
amino
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FI942010A
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English (en)
Finnish (fi)
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FI942010A (sv
FI942010A0 (sv
Inventor
Eddy Jean Edgard Freyne
Chaffoy De Courcelles Didie De
Alfons Herman Raeymaekers
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Janssen Pharmaceutica Nv
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Publication of FI942010A0 publication Critical patent/FI942010A0/sv
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Publication of FI105548B publication Critical patent/FI105548B/sv

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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

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

Claims (8)

1. Förfarande för framställning av farmaceutiskt aktiva 1,3-dihydro-2H-imidazo[4,5-b]kinolin-2-oner med 5 formeln (I), farmaceutiskt godtagbara additionssalter därav eller stereokemiska isomerformer därav, X t (I c H V ' iXx väri R är väte, fenyl, som valfritt är substituerad med 15 1-3 substituenter, vilka envar självständigt är valda bland halogen, C^-alkyloxi och C1.6-alkyl; eller R är pyridinyl; X C=X är en radikal med formeln 20 I^C=0 (a) eller X:c=N-0-R1 (b) ; R1 är C^.g-alkyl valfritt substituerad med COOH, COOC-^-alkyl eller CONR3R4, ” 25 R3 är C^-alkyl; R4 är C3.7-cykloalkyl; eller R3 och R4 kan tillsammans med kväveatomen, vid vil-ken de är bundna, bilda en piperazinylring, varvid piperazinylringen valfritt i kväveatomen är substituerad 30 med C1.4-alkyl eller (C3_7-cykloalkyl) -C^-alkyl ; * kännetecknat därav, att man a) cykliserar en mellanprodukt med formeln X 35 'ij> * €Q> NH2 o H 32 105548 väri R och C=X är säsom ovan def inierats, i ett lös-ningsmedel i närvaro av en syra; b) cykliserar en mellanprodukt med formeln l (III) * 1CQ>0 nh2 O h 10 väri R och ^ C=X är säsom ovan definierats, i ett lös-ningsmedel i närvaro av en syra; c) omvandlar föreningarna med formeln (I) tili varandra genom esterhydrolys; och om önskvärt, omvandlar föreningarna med formeln (I) 15 tili saltform genom behandling med en farmaceutiskt god-tagbar syra eller bas, eller omvänt, omvandlar saltformen tili en fri bas eller en fri syra genom behandling med alkali, respektive syra; och/eller framställer stereo-kemiska isomerformer därav. 20
2. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att R är väte; fenyl, som valfritt är substituerad med 1 eller 2 substituenter, vilka envar självständigt är valda bland halogen, C^-alkyloxi eller Cj.g-alkyl; eller R är pyridinyl. 25
3. Förfarande enligt patentkrav 2, känne- t e c k n a t därav, att R är väte; fenyl, som valfritt är substituerad med 1 eller 2 substituenter, vilka envar självständigt är valda bland fluor, klor, brom, metoxi eller metyl; eller R är pyridinyl; och C=X är en 30 radikal med formeln (a) eller (b) , väri R1 är C^-alkyl, ! som valfritt är substituerad med COOH, COOC^-alkyl eller CONR3R4.
4. Förfarande enligt patentkrav 3, känne- ’ t e c k n a t därav, att R är väte eller fenyl, som 35 valfritt är substituerad med 1 eller 2 substituenter, 33 105548 eller metyl, och ^C=X är en radikal med formeln (a) eller (b) ; väri R1 är C1.4-alkyl, som valfritt är substituerad med COOH, COOC2H5, CON(CH3) (c.CgH^) eller 5 5? /—\ —C-N^_^N—CH2—(cCeHu).
5. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer (E) -N-cyklo- 10 hexyl-2-[[[(2,3-dihydro-2-oxo-lH-imidazo[4,5-b]kinolin-7-yl)fenylmetylen]amino]oxi]-N-metylacetamid.
6. Förfarande enligt patentkrav 1, kanne- t e c k n a t därav, att man framställer 7-benzoyl-1,3-dihydro-2H-imidazo[4,5-b]kinolin-2-on. 15
7. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer (E) -1- (cyk-lohexylmetyl)-4-[[[[(2,3-dihydro-2-oxo-lH-imidazo[4,5-b]-kinolin-7-yl)metylen]amino]oxi]acetyl]piperazin.
8. Förfarande enligt patentkrav 1, känne-20 tecknat därav, att man framställer (E) -N-cyk-lohexyl-2-[[[(2,3-dihydro-2-oxo-lH-imidazo[4,5-b]kinolin-7-yl) metylen] amino] oxi] -IJ-nietylacetamid. ♦ *'
FI942010A 1991-10-30 1994-04-29 Förfarande för framställning av farmaceutiskt aktiva 1,3-dihydro-2H-imidazo(4,5-b)kinolin-2-oner FI105548B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US78495591A 1991-10-30 1991-10-30
US78495591 1991-10-30
PCT/EP1992/002496 WO1993009118A1 (en) 1991-10-30 1992-10-27 1,3-dihydro-2h-imidazo(4,5-b)quinolin-2-one derivatives as phosphodiesterase inhibitors
EP9202496 1992-10-27

Publications (3)

Publication Number Publication Date
FI942010A FI942010A (sv) 1994-04-29
FI942010A0 FI942010A0 (sv) 1994-04-29
FI105548B true FI105548B (sv) 2000-09-15

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FI942010A FI105548B (sv) 1991-10-30 1994-04-29 Förfarande för framställning av farmaceutiskt aktiva 1,3-dihydro-2H-imidazo(4,5-b)kinolin-2-oner

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US (3) US5521187A (sv)
EP (2) EP0610372B1 (sv)
JP (1) JP3488922B2 (sv)
KR (1) KR100251895B1 (sv)
CN (1) CN1041726C (sv)
AT (1) ATE131479T1 (sv)
AU (1) AU660337B2 (sv)
CA (1) CA2121230C (sv)
DE (1) DE69206820T2 (sv)
DK (1) DK0610372T3 (sv)
ES (1) ES2083773T3 (sv)
FI (1) FI105548B (sv)
GR (1) GR3018909T3 (sv)
HU (1) HU220608B1 (sv)
IL (1) IL103570A (sv)
MX (1) MX9206258A (sv)
NO (1) NO300976B1 (sv)
NZ (1) NZ244779A (sv)
PH (1) PH31245A (sv)
PL (1) PL170749B1 (sv)
RU (1) RU2127273C1 (sv)
TW (1) TW249234B (sv)
WO (1) WO1993009118A1 (sv)
ZA (1) ZA928373B (sv)

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US5521187A (en) 1996-05-28
NO941497L (no) 1994-04-25
HU220608B1 (hu) 2002-03-28
FI942010A (sv) 1994-04-29
CA2121230C (en) 2003-03-11
EP0610372A1 (en) 1994-08-17
US5516908A (en) 1996-05-14
KR100251895B1 (ko) 2000-09-01
JPH07500599A (ja) 1995-01-19
HUT66453A (en) 1994-11-28
IL103570A (en) 1996-03-31
NO300976B1 (no) 1997-08-25
AU660337B2 (en) 1995-06-22
AU2908392A (en) 1993-06-07
CN1072681A (zh) 1993-06-02
IL103570A0 (en) 1993-03-15
DE69206820T2 (de) 1996-05-15
JP3488922B2 (ja) 2004-01-19
ATE131479T1 (de) 1995-12-15
TW249234B (sv) 1995-06-11
EP0610372B1 (en) 1995-12-13
US5541325A (en) 1996-07-30
FI942010A0 (sv) 1994-04-29
DE69206820D1 (de) 1996-01-25
EP0541153A1 (en) 1993-05-12
NZ244779A (en) 1994-10-26
CA2121230A1 (en) 1993-05-13
GR3018909T3 (en) 1996-05-31
RU2127273C1 (ru) 1999-03-10
NO941497D0 (sv) 1994-04-25
MX9206258A (es) 1993-04-01
WO1993009118A1 (en) 1993-05-13
CN1041726C (zh) 1999-01-20
HU9401245D0 (en) 1994-08-29
ZA928373B (en) 1994-04-29
PL170749B1 (pl) 1997-01-31
DK0610372T3 (da) 1996-01-29
PH31245A (en) 1998-06-18
ES2083773T3 (es) 1996-04-16

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