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KR970707099A - 5-LIPOXYGENASE INHIBITORS (5-LIPOXYGENASE INHIBITORS) - Google Patents

5-LIPOXYGENASE INHIBITORS (5-LIPOXYGENASE INHIBITORS)

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Publication number
KR970707099A
KR970707099A KR1019970702527A KR19970702527A KR970707099A KR 970707099 A KR970707099 A KR 970707099A KR 1019970702527 A KR1019970702527 A KR 1019970702527A KR 19970702527 A KR19970702527 A KR 19970702527A KR 970707099 A KR970707099 A KR 970707099A
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alkyl
halo
compound according
substituted
alkylene
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KR1019970702527A
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KR100239930B1 (en
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로드니 더블유 스티븐스
다카시 마노
가즈나리 나카오
요시유키 오쿠무라
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스피겔 알렌 제이
화이자 인코포레이티드
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Priority claimed from PCT/IB1995/000408 external-priority patent/WO1996011911A1/en
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    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 5-리폭시게나제 효소를 저해하는 능력을 갖는 하기 화학식(Ⅰ)의 신규한 화합물 및 그의 약학적으로 허용되는 염을 제공한다.The present invention provides a novel compound of formula (I) having the ability to inhibit 5-lipoxygenase enzyme and its pharmaceutically acceptable salts.

상기 식에서, Ar1은 이미다졸릴, 피롤릴, 피라졸릴, 1,2,3-트리아졸릴, 1,2,4-트리아졸릴, 인돌릴, 인다졸릴 및 벤즈이미다졸릴로부터 선택된 헤테로사이클 잔기이고, 이는 고리의 질소 원자를 통해 X1에 결합되고, 또한 할로, 하이드록시, 시아노, 아미노, C1-C4알킬 등으로부터 선택된 1개 또는 2개의 치환체로 임의로 치환될 수 있고; X1은 직접 결합 또는 C1-C4알킬렌이고; Ar2는 할로, 하이드록시, 시아노, 아미노 등으로 임의로 치환된 페닐렌이고; X2는 -A-X- 또는 -X-A- (여기서 A는 직접 결합 또는 C1-C4알킬렌이고 X는 옥시, 티오, 설피닐 또는 설포닐이다)이고; Ar3는 할로, 하이드록시, 시아노, 아미노, C1-C4알킬 등으로부터 선택된 1개 또는 2개의 치환체로 임의로 치환된 페닐렌, 피리딜렌, 티에닐렌, 푸릴렌, 옥사조릴렌 또는 티아졸릴렌이고; R1및 R2는 각각 C1-C4알킬이거나, 함께 화학식 -D1-Z-D2-의 그룹(이 그룹은 여기에 결합된 탄소 원자와 함께 3 내지 8개의 원자를 갖는 고리를 형성하고, D1및 D2는 C1-C4알킬렌이고 Z는 직접 결합 또는 옥소, 티오, 설피닐, 설포닐 또는 비닐렌이고, D1및 D2는 C1-C3알킬에 의해 치환될 수 있다)을 형성하고; Y는 CONR3R4, CN, C(R3)=N-OR4, COOR3, COR3또는 CSNR3R4(여기서, R3및 R4는 각각 H 또는 C1-C4알킬이다)이다. 상기 화합물은 포유동물의 염증성 질환, 알레르기 및 심혈관 질환의 치료 및 완화에 유용하고 상기 상태의 치료를 위한 약학 조성물에서 활성 성분으로서 유용하다.Wherein Ar 1 is a heterocycle residue selected from imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl , which is bonded to X 1 through a nitrogen atom of the ring, and halo, hydroxy, cyano, amino, C 1 -C 4 may be optionally substituted with one or two substituents selected from alkyl, and the like; X 1 is a direct bond or C 1 -C 4 alkylene; Ar 2 is phenylene optionally substituted with halo, hydroxy, cyano, amino and the like; X 2 is -AX- or -XA-, wherein A is a direct bond or C 1 -C 4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar 3 is selected from halo, hydroxy, cyano, amino, C 1 -C 4 alkyl such as jo 1 or 2 optionally substituted with substituents phenylene, pyridylene group, thienylene, Fu tolylene selected from, oxazolyl or thiazolyl tolylene ; Wherein R 1 and R 2 are each C 1 -C 4 alkyl or together form a group of the formula -D 1 -ZD 2 -, in which the group together with the carbon atoms bonded thereto form a ring having 3 to 8 atoms, D 1 and D 2 are C 1 -C 4 alkylene and Z is a direct bond or oxo, thio, sulfinyl, sulfonyl or vinylene, and D 1 and D 2 may be substituted by C 1 -C 3 alkyl ); Y is CONR 3 R 4 , CN, C (R 3 ) = N-OR 4 , COOR 3 , COR 3 or CSNR 3 R 4 wherein R 3 and R 4 are each H or C 1 -C 4 alkyl, to be. Such compounds are useful in the treatment and amelioration of inflammatory diseases, allergies and cardiovascular diseases of mammals and are useful as active ingredients in pharmaceutical compositions for the treatment of such conditions.

Description

5-리폭시게나제 저해제(5-LIPOXYGENASE INHIBITORS)5-LIPOXYGENASE INHIBITORS (5-LIPOXYGENASE INHIBITORS)

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (13)

하기 화학식(Ⅰ)의 화합물 및 그의 약학적으로 허용되는 염:Claims 1. Compounds of the formula (I) < EMI ID = 상기 식에서, Ar1은 이미다졸릴, 피롤릴, 피라졸릴, 1,2,3-트리아졸릴, 1,2,4-트리아졸릴, 인돌릴, 인다졸릴 및 벤즈이미다졸릴로 이루어진 그룹으로부터 선택된 헤테로사이클 잔기이고, 이는 고리의 질소 원자를 통해 X1에 결합되고, 또한 할로, 하이드록시, 시아노, 아미노, C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4할로-치환된 알킬, C1-C4할로-치환된 알콕시, C1-C4알킬아미노 및 디(C1-C4)알킬아미노로부터 선택된 1개 또는 2개의 치환체로 임의로 치환될 수 있고; X1은 직접 결합 또는 C1-C4알킬렌이고; Ar2는 할로, 하이드록시, 시아노, 아미노, C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4할로-치환된 알킬 및 C1-C|4할로-치환된 알콕시로부터 선택된 1개 또는 2개의 치환체로 임의로 치환된 페닐렌이고; X2는 -A-X- 또는 -X-A-(여기서, A는 직접 결합 또는 C1-C4알킬렌이고, X는 옥시, 티오, 설피닐 또는 설포닐이다)이고; Ar3는 할로, 하이드록시, 시아노, 아미노, C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4할로-치환된 알킬, C1-C4할로-치환된 알콕시, C1-C4알킬아미노 및 디(C1-C4)알킬아미노로부터 선택된 1개 또는 2개의 치환체로 임의로 치환된 페닐렌, 피리딜렌, 푸릴렌, 옥사졸릴렌 또는 티아졸릴렌이고; R1및 R2는 각각 C1-C|4알킬이거나, 함께 화학식 -D1-Z-D2-의 그룹(이 그룹은 결합된 탄소 원자와 함께 3 내지 8개의 원자를 갖는 고리를 형성하고, D1및 D2는 C1-C4알킬렌이고 Z는 직접 결합 또는 옥시, 티오, 설피닐, 설포닐 또는 비닐렌이고, D1및 D2는 C1-C3알킬에 의해 치환될 수 있다)을 형성하고; Y는 CONR3R4, CN, C(R3)=N-OR4, COOR3, COR3또는 CSNR3R4(여기서, R3및 R4는 각각 H 또는 C1-C4알킬이다)이다.Wherein Ar 1 is selected from the group consisting of imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl the cycle moiety, which is bonded to X 1 through a nitrogen atom of the ring, and halo, hydroxy, cyano, amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, Optionally substituted with one or two substituents selected from C 1 -C 4 halo-substituted alkyl, C 1 -C 4 halo-substituted alkoxy, C 1 -C 4 alkylamino and di (C 1 -C 4 ) alkylamino ≪ / RTI > X 1 is a direct bond or C 1 -C 4 alkylene; Ar 2 is halo, hydroxy, cyano, amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 halo-substituted alkyl and C 1 -C | 4 halo-substituted alkoxy; < RTI ID = 0.0 > R < / RTI > X 2 is -AX- or -XA-, wherein A is a direct bond or C 1 -C 4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar 3 is selected from halo, hydroxy, cyano, amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 halo-substituted alkyl, C 1 -C 4 halo-substituted alkoxy, C 1 -C 4 alkylamino and di (C 1 -C 4) optionally substituted by one or two substituents selected from alkyl, amino phenylene, pyridylene group, Fu tolylene, oxazolyl alkylene or Thiazolyl; R 1 and R 2 are each C 1 -C | 4 alkyl or, with the formula -D 1 -ZD 2 - in the group (the group is bonded to form a ring having from 3 to 8 atoms with the carbon atom, and D 1 and D 2 is a C 1 -C 4 alkylene And Z is a direct bond or oxy, thio, sulfinyl, sulfonyl or vinylene, and D 1 and D 2 may be substituted by C 1 -C 3 alkyl; Y is CONR 3 R 4 , CN, C (R 3 ) = N-OR 4 , COOR 3 , COR 3 or CSNR 3 R 4 wherein R 3 and R 4 are each H or C 1 -C 4 alkyl, to be. 제1항에 있어서, Ar3가 임의로 치환된 페닐렌인 화합물. 3. A compound according to claim 1, wherein Ar < 3 > is optionally substituted phenylene. 제2항에 있어서, Ar2가 1,4-페닐렌이고, Ar3가 1,3-페닐렌 또는 5-플루오로-1,3-페닐렌인 화합물.The compound according to claim 2, wherein Ar 2 is 1,4-phenylene and Ar 3 is 1,3-phenylene or 5-fluoro-1,3-phenylene. 제3항에 있어서, Ar1이 2-알킬이미다졸릴이고, X1이 직접 결합인 화합물.The compound according to claim 3, wherein Ar 1 is 2-alkylimidazolyl and X 1 is a direct bond. 제4항에 있어서, Y가 CONH2또는 CH=N-OCH3인 화합물.The method of claim 4, wherein, Y is CONH 2 or CH = N-OCH 3 A compound. 제5항에 있어서, R1및 R2D1-Z-D2이고, 상기 D1및 D2가 각각 에틸렌이고, Z가 O인 화합물.The compound according to claim 5, wherein R 1 and R 2 D 1 -ZD 2 , wherein D 1 and D 2 are each ethylene and Z is O. 제6항에 있어서, Ar1이 2-메틸이미다졸릴이고, X2가 CH2O인 화합물.The compound according to claim 6, wherein Ar 1 is 2-methylimidazolyl and X 2 is CH 2 O. 제6항에 있어서, Ar1이 2-메틸이미다졸릴이고, X2가 S인 화합물.7. A compound according to claim 6 wherein Ar < 1 > is 2-methylimidazolyl and X < 2 > 제3항에 있어서, Ar1이 피롤릴이고, X1이 CH2이고, X2가 S이고, Y가 CONH2인 화합물.The compound according to claim 3, wherein Ar 1 is pyrrolyl, X 1 is CH 2 , X 2 is S, and Y is CONH 2 . 제1항에 있어서, 하기 화합물로부터 선택된 화합물: 4-[5-플루오로-3-[4-(2-메틸이미다졸-1-일)벤질옥시]페닐]-3,4,5,6-테트라하이드로-2H-피란-4-카복사미드; 4-[3-[4-(2-메틸이미다졸-1-일)페닐티오]페닐]-3,4,5,6-테트라하이드로-2H-피란-4-카복사미드; 4-[3-[4-(피롤-1-일메틸)페닐티오]페닐]-3,4,5,6-테트라하이드로-2H-피란-4-카복사미드; (2SR, 4RS)-2-메틸-4-[3-[4-(2-메틸이다졸-1-일)페닐티오]페닐]-3,4,5,6-테트라하이드로-2H-피란-4-카복사미드; 및 4-메톡시이미노메틸-4-[3-[4-(2-메틸이미다졸-1-일)페닐티오]페닐]-3,4,5,6-테트라하이드로-2H-피란.2. A compound according to claim 1 selected from the group consisting of: 4- [5-fluoro-3- [4- (2-methylimidazol-1-yl) benzyloxy] phenyl] - tetrahydro-2H-pyran-4-carboxamide; 4- [3- [4- (2-methylimidazol-1-yl) phenylthio] phenyl] -3,4,5,6-tetrahydro-2H-pyran-4-carboxamide; 4- [3- [4- (pyrrol-1-ylmethyl) phenylthio] phenyl] -3,4,5,6-tetrahydro-2H-pyran-4-carboxamide; (2SR, 4RS) -2-methyl-4- [3- [4- (2-methylthiazol- 1 -yl) phenylthio] phenyl] -3,4,5,6-tetrahydro- 4-carboxamide; And 4-methoxyiminomethyl-4- [3- [4- (2-methylimidazol-1-yl) phenylthio] phenyl] -3,4,5,6-tetrahydro-2H-pyran. 포유동물의 알레르기성 또는 염증성 상태를 치료하기 위한, 치료효과량의 제1항의 화합물 및 약학적으로 허용되는 담체를 포함하는 약한 조성물.A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier for the treatment of an allergic or inflammatory condition in a mammal. 5-리폭시게나제 저해제를 필요로 하는 포유동물의 의학적 상태를 치료하기 위한, 포유동물에게 치료효과량의 제1항에 따른 화합물을 투여함을 포함하는 방법.The method comprising administering to a mammal a therapeutically effective amount of a compound according to claim 1 for the treatment of a medical condition in a mammal in need of a 5-lipoxygenase inhibitor. 제12항에 있어서, 상기 의학적 상태가 알레르기성 또는 염증성 상태인 방법.13. The method of claim 12, wherein the medical condition is an allergic or inflammatory condition. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019970702527A 1994-10-18 1995-05-29 5-lipoxygenase inhibitors KR100239930B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
WO94/01747 1994-10-18
WOPCT/JP94/01747 1994-10-18
IB9401747 1994-10-18
PCT/IB1995/000408 WO1996011911A1 (en) 1994-10-18 1995-05-29 5-lipoxygenase inhibitors

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