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SI9111647B - Unsaturated hydroxyalkylquinoline acids - Google Patents

Unsaturated hydroxyalkylquinoline acids Download PDF

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SI9111647B
SI9111647B SI9111647A SI9111647A SI9111647B SI 9111647 B SI9111647 B SI 9111647B SI 9111647 A SI9111647 A SI 9111647A SI 9111647 A SI9111647 A SI 9111647A SI 9111647 B SI9111647 B SI 9111647B
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phe
cme2oh
sch2
chetco2h
alkyl
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SI9111647A (en
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L Michel Belley
Serge Leger
Patrick Roy
Yi Bin Xiang
Marc Labelle
Danial Guay
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Merck Frosst Canada Inc
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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
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D215/20—Oxygen atoms
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    • A—HUMAN NECESSITIES
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    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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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
    • C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Claims (6)

1 PATENTNI ZAHTEVKI 1. Spojina s formulo: 5 C^MCR^ZUCR^ni / (Χ^ν R7 / ^
(CRi2)m,Z2B'(CRiR4)p,CR2RiQ2 10 kjer je: R1 je H, halogen, -CF3, -CN, -N02 ali N3; R2 je nižji alkil, nižji alkenil, nižji alkinil, -CF3, -CH2F, -CHF2, 15 CH2CF3, substituiran ali nesubstituiran fenil, substituiran ali nesubstituiran benzil, substituiran ali nesubstituiran 2-fenetil ali dve R2 skupini, ki sta vezani na isti ogljik, da tvorita karbocikličen obroč z do 8 členi; R3 je H ali R2; R4 je halogen, -N02, -CN, -OR3, -SR3, NR3R3, NR3C(0)R7 ali R3; R5je H, halogen, -N02, -N3, -CN, -SR2, -NR3R3, -OR3, nižji alkil ali -C(0)R3; R6 je -(CH2)5-C(R7R7)-(CH2)5-R8 ali -CH2C(0)NR12R12; R7je H ali C1-C4 alkil; R8 je radikal W-R9; 20 2 R9 vsebuje do 20 atomov ogljika in (1) je alkiina skupina ali (2) je alkilkarbonilna skupina organske aciklične ali monociklične karboksilne kisline; R11 je nižji alkil, -C(0)R14, nesubstituiran fenil ali nesubstituiran 5 benzil; R12 je H ali R11; R13 je nižji alkil, nižji alkenil, nižji alkinil, -CF3 ali substituiran ali nesubstituiran fenil, benzil ali 2-fenetil; R14 je H ali R13; 10 R16 je H, C1-C4 alkil ali OH; R17 je nižji alkil, nižji alkenil, nižji alkinil ali substituiran ali nesubstituiran fenil, benzil ali 2-fenetil; R18 je nižji alkil, nižji alkenil, nižji alkinil, -CF3 ali substituiran ali nesubstituiran fenil, benzil ali 2-fenetil; 15 R19 je nižji alkil, nižji alkenil, nižji alkinil, -CF3 ali substituiran al nesubstituiran fenil, benzil ali 2-fenetil; R21 je H ali R17; R22 je R4, CHR7OR3 ali CHR7SR2; m je 0-8; 20 m' je 2 ali 3; n in n' sta neodvisno 0 ali 1; p in p' sta neodvisno 0-8; m+n+p je 1-10, kadar je r enak 1 in je X2 enak 0, S, S(0) ali S(0)2; 3 m+n+p je 0-10, kadar je r enak 1 in je X2 enak CR3R16 m+n+pje 0-10, kadar je r enak 0; m'+n'+p'je 2-10; r in r' sta neodvisno 0 ali 1; 5 s je 0-3; Q1 je -C(0)0R3, 1H (ali 2H)-tetrazol-5-il, -C(0)0R6, -C(0)NHS(0)2R13, -CN, -C(0)NR12R12 NR21S(0)2R13, -NR12C(0)NR12R12, -NR12C(0)R18, -0C(0)NR12R12, -C(0)R19,-S(0)R18, 10 -S(0)2R18, -S(0)2NR12R12, -N02, -NR21C(0)0R17, -C(NR12R12)=NR12; Q2 je OH; W je 0, S ali NR3; X2 in X3 sta neodvisno 0, S, S(0), S(0)2 ali CR3R16, pod pogojem, da 15 je vsaj eden od obeh S ali S02; Y je -CR3=CR3-; Z1 in Z2 sta neodvisno -HET(-R3-R5)-; HETje diradikal benzena, piridina, furana ali tiofena.
2. Spojina po zahtevku 1, kjer je R1 je H, halogen, CF3 ali -CN; R2 je C1-C4 alkil, -CF3, -CHF2i -CH2F ali dve R2 skupini, ki sta vezani na isti ogljik, da tvorita obroč z do 6 ogljiki; 4 R3 je H ali R2; R4 je -OR3, -SR3, NR3R3, NHC(0)CH3ali R3; R5 je H ali halogen; R6 je -(CH2)5-C(R7R7)-(CH2)5-R8 ali -CH2C(0)NRl2R12; 5 R7 je H ali Ci-C4 alkil; R8 je radikal W-R9; R9 vsebuje do 20 atomov ogljika in (1) je alkilna skupina ali (2) je alkilkarbonilna skupina; R11 je nižji alkil, -C(0)R14, nesubstituiran fenil ali nesubstituiran 10 benzil; R12 je H ali R11; R13 je nižji alkil, -CF3 ali substituiran ali nesubstituiran fenil, benzil ali 2-fenetil; R14 je H ali R13; 15 R16 je H, ΟΛ alkil ali OH; R22 je R4, -CH2OR3 ali -CH2SR2; m je 0-4; m' je 2 ali 3; n in n' sta neodvisno 0 ali 1; 20 p in p' sta neodvisno 0-4; m+n+p je 1 -9, kadar je r enak 1 in je X2 enak 0 ali S; m+n+p je 0-9, kadar je r enak 1 in je X2 enak CR3R16; m+n+p je 0-9, kadar je r enak 0; 5 m'+n'+p' je 2-9; r in r' sta neodvisno O ali 1; s je 0-3; Q1 je -C(0)0R3, 1H (ali 2H)-tetrazol-5-il, -C(0)0R6, 5 10 -C(0)NHS(0)2R13, -C(0)NR12R12. -NHS(0)2R13; Q2 je OH; W je O, SaliNH; X2 in X3 sta neodvisno O, S ali CR3R16, pod pogojem, da je vsaj eden od obeh S; Y je (E)-CH=CH-; Z1 in Z2 sta neodvisno -HET(-R3-R5)-; HET je diradikal benzena, piridina, furana ali tiofena.
3. Spojina po zahtevku 1, označena s tem, da je R22 a proti O1 nižji alkil, 15 CF3 ali substituiran ali nesubstituiran fenil.
4. Spojina po zahtevku 1 s formulo la:
6 kjer je R1 je H, halogen, CF3 ali CN; R22 je R3, -CH2OR3 ali -CH2SR2; 5 Q1 je -C(0)0H, 1H (ali 2H)-tetrazol-5-il, -C(0)NHS(0)2R13 -C(0)NR12R12 ali -NHS(0)2R13; m' je 2 ali 3; p' je O ali 1; m+p je 1 do 5. ίο 5. Spojina po zahtevku 4, označena s tem, da je ogljik a proti Q1 nižji substituiran alkil.
6. Spojina po zahtevku 1 s formulo Ib
20 kjer je R1 je H, halogen, CF3 ali CN; R22 je R3, -CH2OR3 ali -CH2SR2; Q1 je -C(0)0H, 1H (ali 2H)-tetrazol-5-il, -C(0)NHS(0)2R13, 7 -C(0)NR12R12 ali -NHS(0)2R13; m je O, 2 ali 3; p je O ali 1, p' je 2 do 4; 5 m+p je 0 do 4.
7. Spojina po zahtevku 1 s formulo Γ
15 kjer so substituente kot sledi: EX. Λ Rl Y A B 2 RS 7-C1 CH=CH s(ch2)2co2h (CH2)2(l,2-phe)C((CH2)z<)0H 3 RS 7—C1 CH=CH s(ch2)2co2h (CH2)2(ii-Cl-l, 2-phe)CMe2QH 5 RS 7-C L CHsCH s(ch2)2co2h (CH2)2(l,2-phe)CMe20H 6 RS 7-Cl CH=CH SCH2CHHeC02H S<CR2)2(l-c-Pen)OH 7 RS 7-C1 CH=CH SCH2(R)CHMeC02H S(CH2)2(1,2-phe)CMe2OH 12 S 7-Cl CH=CH SCH2(S)CHEtC02H (CH2)3(l,2-phe)CMe20H 13 R.S 7-Cl CH*CH S(CH2)2CHMeC02H (CH2)2(l,2-phe)CMe20H 8 εχ. Α R1 Y A B 15 RS 7-C1 CHjpCH SCHjCHMeCOjH (CH2)2(l,2-phe)CMe20H 16 S" 7-Cii CH=CH SCH2(S)CHMeCQ2H (CH2)2(1,2-phe}CHe2OH 17 R 7-C1 CH=CH SCH2(S)CHneC02H (CH2)2(l,2-phe)CMe2OH 1.8. S 7-C1 CH=Cti s(ch2)2co2h S(CH2)2CMe20H 19 S 7-C1 CH=CH SCH2CHMeC02H (CH2)2(1,2-phe)C(CF3)2OB 20 RS 7-C1 CH=CH SCR2CBi1eC02H (CH2)2(1,3-phc)C(CF3)2OH 21 RS 7-C1 CH=CH SCH2'CHMeC02K (CB2)2(l,3-phc)Cile2OH 22 RS 7-C1 CH=CB SCH2CHEtC02H SCH2CMe2CMe2OB 23 RS 7-C1 CH=CH SCHjCHMeCMejOH (CH2)2(l,2-phe)C02H 24 RS 7-C1 CH=CH SCH2CHMeCMe2OH (CH2)2(1,2-phe)CONH2 2'5 RS 7 -C 1 CHcCH SCH2CHMeC02H SCH2(l,2-phe)CMe20R 26 RS 7-C1 CH=CH SCH2CHHeC02H (CH2)2(1,6-phe)CMe2OH 27 RS 7-C1 CH*CH SCH2CHEtC02H (CH2)2(l,2-phe)CMe2OH 28 RS 7-C1 CH=CH SCH2CB(0Me)CO2H (CH2)2(l,2-phe)Ole2OH 29 S 7-C1 CH*CH SCH2(R)CHEtC02H (CH2)2(1,2-phe)CHe2OH 30 RS 7-C1 CH=CH s(ck2)2co2h (CH2)2(1,2-ph*)CH(CF3)OH 31 S 7-C1 CH=CH SCH2(R)CHMeC02H (CH2)2(l,2-phe)CMc20H 32 S 7-C1 CH=C8 SCH2(S)CHEtC02H (CR2)2(l,2-phe)CMe20H 33 RS 7-C1 CH=CH SCH2CHe2C02H (CH2)2(1.2-phe)CHe2OH 42 RS 7-C1 CH=CE SCH2CHMeC02H (CH2)2(l,2-phe)CHe2H«2 64 RS 7-Br C*C SCH2CHEtC02H (CH2)2(l,2-phe)CMe2OH 65 S 7 —C 1 CH=CH sch2cb(ch2ch-ch2)co2h (CH2)2(1,2-phe)CMe2OH 7*6 RS 7-C1 Gtt=CH SCH2CHEtC02H (l,2-phe)CMe20H 77 S 7-C1 CH=CH SCH2CHEtC02H (CH2)2(l,2-phe)C(CH20CH2)0H 128 R 7-C1 CH=CH S(R)CHHcCH2C02H (CH2)2(l,2-phe)CMe20H 129 R 7-C1 CB=CH S(S)CHMe(S)CHMeC02M (CH2)2Cl,2-phe)CMe2OH 130 R 7-C1 CH=CH S(R)CHMe(R)CHMeC02H (CB2)2C1,2-phe)Ct1e2OH 131 R 7-C1 CH=CH SCHEtCH2C02H (CH2)2(1,2-phe)CMe2OH 132 S 7-C1 CB-CB S(CH2)3CHMeOH (CH2)2(l,2-phe)CBEtC02H 134 R 7-C1 CH=CH SCt1e2CH2C02H (CH2)2(l,2-ph*)CMe2OH 135 R 7-C1 CH*CH SCH2CHMeCH2C02H (CH2)2(l,2-phe)CMe2OH 136 R 7-CF3 CH=CH SCH2CMe2CK2C02H (CH2)2(1,2-phe)CMe2OH 138 S 7-C1 CH=CH S(CH2)3CMe2OB (CB2)2(l,2-ph«)(R)CHEtC02H 139 S 7—C1 CH*CR S(CH2)3CMe2OH (CB2)2(l.2-phe)(S)CHEcC02H 160 S 7-C1 CH-CB S(CH2)3CHe20B (CH2)2(6-Cl-l,2-ph»)CHEtC02H 161 S 7-C1 CH=CH S(CH2)3CTIe20H (CH2)2(l,2-phe)CEt2C02H 142 S 7-C1 CH=CH S(CH2)3CHe2OH (CH2)2(1,2-phe)CB2C02H 9 ΕΧ. * R1 y A B Η3 S 7-C1 CH=CH S(CH2)3CMe2OH (CH2)2(l,2-phe)CB(0H)C02H 144 S 7-C1 CH=CH S(CH2)3CMe2OH (CH2)2(l,2-phe)CHEtC02H 1*5 s 7-C1 CH=CH S(CH2)3CMe20H (CH2)2CHMeCH2C02H 146 R 7-C1 CH=CH SCH2Cfle2CH2C02H (CH2)2(l,2-phe)CMe2OH 1*7 S 7-C1 CH=CH StCH^CMejOH (CH2)2(l,2-phe)CHEtC02H 1*8 S 6—C1 CB=CH S(C82)3CMe20H (CH2)2(l,2-phe)C02H 1*9 S 8-C1 CH=CH S(CH2)3CMe2OH (CH2)2(l,2-phe)C02H 150 s 7-F CH=CH S(CH2)3CMc2OH (CH2)2(l,2-phe)CHEtC02H 151 s 7—Br CH=CH S(CH2)3CMe2OH (CH2)2(l,2-phe)CHMeC02H 152 s 7-1 δ 1! X u SCH2C(1,l-c-Pr)CH2C02H (CH2)2(l,2-phe)CMe20H 153 s 7-N02 CH=CH SCH2C(L,l-c-Pr)CH2C02H (CH2)2(L.2-phe)CHe20H 15¾ R 7-N3 CHaCH SCH2C(1,l-c-Pr)CH2C02H (CH2)2(1,2-phe)CHe20H 155 RS 7-C1 CH=CH S(CH2)2CMe2OH (CH2)2CMe2CH2C02H 156 R 7-C1 CH=€H S(1,2-phe)CH2C02H (CH2)2(l,2-phe)C«e20H 157 R 7-C1 CH=CH S(CH2)3CMe2OH (CH2)2(1,2-phe)CHEtC02H 15Θ S 7—C1 CH=CH S(CK2)2CMe20H (CH2)2(l,2-phe)CHEtC02H 15? S 7-C1 CHaCH SfCH2)3CMe(i-Cl-Ph)OH (CH2)2(l,2-phe)CHEtC02H 160 R 7-C1 CH=CH SCH2(1,2-phe)CMe2OH (CH2)2CMe2CH2C02H 161 R 7—C1 CH=CH SCH2(1,l-c-Pr)CH2C02H (CH2)2(l,2-phe)CMczOa 162 R 7-C1 CH=CH sch2(1,1-c-Bu)CH2C02H (CH2)2(l,2-phe)CHe2OH 163 R 7-C1 CHaCH SCH2CMe2CHMeC02H (CH2)2(l,2-phe)Cf1e2OH 16<t S 7-C1 CH=CH SCH2(l,2-phc)CMe2OH (CH2)2C«e2CK2C02H 165 R 7-C1 CH=CH SCHMeCMe2CH2C02R (CH2)2(l,2-phe)O1e20H 166 R 7-C1 CH=CH S(l,l-c-Pr)CH2C02H (CB2)2(l,2-phe)Ctte2OH 167 R 7-C1 CH=CH S(l,l-c-Pr>CHMeC02H (CH2)2(1.2-phe)O1e20H
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IE59889B1 (en) * 1986-02-14 1994-04-20 Merck Frosst Canada Inc 2-substituted quinoline dioic acids
US4851409A (en) * 1986-02-14 1989-07-25 Merck Frosst Canada Inc. 2-substituted quinoline dioic acids and pharmaceutical compositions
JPS62258362A (ja) * 1986-05-02 1987-11-10 Terumo Corp アミド誘導体およびこれを含有する５−リポキシゲナ−ゼ作用阻害剤
EP0271287A3 (en) * 1986-12-11 1990-06-13 Merck Frosst Canada Inc. Quinoline dioic acids and amides
EP0318093A3 (en) * 1987-11-25 1990-12-05 Merck Frosst Canada Inc. Diarylquinoline diacids and their use as medicaments
NZ233752A (en) * 1989-05-24 1993-05-26 Merck Frosst Canada Inc Substituted quinoline derivatives, preparation and pharmaceutical compositions thereof
WO1990015801A1 (en) * 1989-06-22 1990-12-27 Pfizer Inc. Substituted sulfonamides and related compounds in the treatment of asthma, arthritis and related diseases

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HK1027473A1 (en) 2001-01-12
NZ240194A (en) 1995-03-28
HU211294A9 (en) 1995-11-28
YU164791A (sh) 1994-04-05
ES2114882T3 (es) 1998-06-16
EP0480717B1 (en) 1998-04-15
HU913217D0 (en) 1992-01-28
CN1061407A (zh) 1992-05-27
IL117147A0 (en) 1996-06-18
DE69129257D1 (de) 1998-05-20
DE69129257T2 (de) 1998-11-05
KR920008006A (ko) 1992-05-27
LU90284I2 (fr) 1998-11-03
CY2094B1 (en) 2002-04-05
CA2053209C (en) 1998-12-08
HU222344B1 (hu) 2003-06-28
FI914796A0 (fi) 1991-10-11
JPH05105665A (ja) 1993-04-27
IE913609A1 (en) 1992-04-22
AU8579491A (en) 1992-04-16
NL990009I1 (nl) 1999-06-01
PT99213B (pt) 1999-01-29
LV12187B (en) 1999-02-20
NO914004D0 (no) 1991-10-11
IL99726A (en) 1998-02-22
CZ281274B6 (cs) 1996-08-14
IL99726A0 (en) 1992-08-18
LV12187A (lv) 1998-12-20
AU639610B2 (en) 1993-07-29
FI104897B (fi) 2000-04-28
CA2053209A1 (en) 1992-04-13
HRP930751A2 (en) 1995-06-30
EP0480717A1 (en) 1992-04-15
YU48742B (sh) 1999-09-27
HUT61981A (en) 1993-03-29
FI914796L (fi) 1992-04-13
SK279944B6 (sk) 1999-06-11
NL990009I2 (nl) 1999-07-01
CS309591A3 (en) 1992-04-15
HRP930751B1 (en) 2000-06-30
FI20000250A7 (fi) 2000-02-07
PT99213A (pt) 1992-09-30
CN1046711C (zh) 1999-11-24
IL117147A (en) 2000-10-31
DE19875039I2 (de) 2003-05-22
DK0480717T3 (da) 1999-02-08
JP2501385B2 (ja) 1996-05-29
MX9101551A (es) 1992-06-05
KR100227716B1 (ko) 1999-11-01
SI9111647A (en) 1997-12-31
ATE165088T1 (de) 1998-05-15

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