KR900701771A - 리폭시게나아제 효소를 억제하는 1, 4-디히드로티오나프토퀴논 및 헤테로시클릭 협동 작용물 - Google Patents
리폭시게나아제 효소를 억제하는 1, 4-디히드로티오나프토퀴논 및 헤테로시클릭 협동 작용물Info
- Publication number
- KR900701771A KR900701771A KR1019900701139A KR900701139A KR900701771A KR 900701771 A KR900701771 A KR 900701771A KR 1019900701139 A KR1019900701139 A KR 1019900701139A KR 900701139 A KR900701139 A KR 900701139A KR 900701771 A KR900701771 A KR 900701771A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- alkyl
- phx
- compound
- different
- Prior art date
Links
- 102000003820 Lipoxygenases Human genes 0.000 title 1
- 108090000128 Lipoxygenases Proteins 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 239000001257 hydrogen Substances 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 2
- 235000008206 alpha-amino acids Nutrition 0.000 claims 2
- -1 amino-substituted phenyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 210000003097 mucus Anatomy 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WLXSSZSBDCIIFH-UHFFFAOYSA-N (2-butyl-4-methylsulfanylnaphthalen-1-yl) acetate Chemical compound C1=CC=CC2=C(OC(C)=O)C(CCCC)=CC(SC)=C21 WLXSSZSBDCIIFH-UHFFFAOYSA-N 0.000 claims 1
- INEYZMMVJPCVNZ-UHFFFAOYSA-N (2-butyl-4-methylsulfonylnaphthalen-1-yl) acetate Chemical compound C1=CC=CC2=C(OC(C)=O)C(CCCC)=CC(S(C)(=O)=O)=C21 INEYZMMVJPCVNZ-UHFFFAOYSA-N 0.000 claims 1
- BBGQRICEPNPZFX-UHFFFAOYSA-N (4-methylsulfanyl-2-phenylnaphthalen-1-yl) acetate Chemical compound CC(=O)OC=1C2=CC=CC=C2C(SC)=CC=1C1=CC=CC=C1 BBGQRICEPNPZFX-UHFFFAOYSA-N 0.000 claims 1
- HGPDLCJRHUEAHO-UHFFFAOYSA-N (5-butyl-7-methylsulfanyl-1-benzofuran-4-yl) acetate Chemical compound CCCCC1=CC(SC)=C2OC=CC2=C1OC(C)=O HGPDLCJRHUEAHO-UHFFFAOYSA-N 0.000 claims 1
- WNGOKMSZAQATGE-UHFFFAOYSA-N (5-ethenyl-6-ethoxy-7-methylsulfanyl-1-benzofuran-4-yl) acetate Chemical compound CC(=O)OC1=C(C=C)C(OCC)=C(SC)C2=C1C=CO2 WNGOKMSZAQATGE-UHFFFAOYSA-N 0.000 claims 1
- QXAFPHBUPMNOJD-UHFFFAOYSA-N (7-methylsulfanyl-5-phenyl-1-benzofuran-4-yl) acetate Chemical compound CC(=O)OC=1C=2C=COC=2C(SC)=CC=1C1=CC=CC=C1 QXAFPHBUPMNOJD-UHFFFAOYSA-N 0.000 claims 1
- BVDASCUGKPWRAB-UHFFFAOYSA-N 1-(6-hydroxy-4-methoxy-7-methylsulfanyl-1-benzofuran-5-yl)ethanone Chemical compound COC1=C(C(C)=O)C(O)=C(SC)C2=C1C=CO2 BVDASCUGKPWRAB-UHFFFAOYSA-N 0.000 claims 1
- OZTKPZJXYSIRAG-UHFFFAOYSA-N 5,6-diethyl-7-methoxy-2-methyl-1-benzofuran-4-ol Chemical compound CCC1=C(CC)C(OC)=C2OC(C)=CC2=C1O OZTKPZJXYSIRAG-UHFFFAOYSA-N 0.000 claims 1
- DBHVGPFCSWOXDP-UHFFFAOYSA-N 5-butyl-7-methoxy-2-methyl-1-benzofuran-4-ol Chemical compound CCCCC1=CC(OC)=C2OC(C)=CC2=C1O DBHVGPFCSWOXDP-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/21—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with the sulfur atom of the thio group bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
내용없음
Claims (11)
- 하기 일반식 I의 화합물 또는 약리학적으로 허용가능한 그들의 산 부가염;상기식에서, R1및 R2는같거나 서로 다르며, (a) 수소, (b) (C1-C10)알킬 (C)(C2-C10)알케닐, 또는 (d) PhX(여기서, (PhX)는 (a)(C1-C1) 알킬, (b)클로로, (c)플루오로, (d)브로모, (e)니트로, (f)트리플루오로메틸, 또는 OR4중 1-3으로 치환된 페닐 임)이며; D는 (a) -CH=CH- (b)-N(CH3), (c) -S-, 또는 (d) -O-이고; R3는 (a) CH3-C(O)- (b) 수소 (c) -C(O)-(CR17R18)m-(CH2)n-NR14R15, (d) -C(O)-AA, 또는 (e) -C(O)-PhX-NH2이고; 상기식들에서, m은 1,2,3 또는 4이고; n은 0,1,2,3,4 또는 5이고; -C(O)AA는 임의의 천연살출 알파-아미노산으로 부터 유도된 아실부분이고; R14및 R15는 같거나 다르며; (a) 수소 (b) (C1-C10) 알킬 (c) -C(O)-R|16(d) -C(O)-PhX, 또는 (e) -PhX이고; 단, n이 0일때 R14및 R15는 수소가 아니며; R16은 (C1-C4)알킬이고 R17및 R18은 같거나 서로 다르며; (a) 수소 (b) (C1-C10) 알킬 (c) -CH2-PhX 또는 (d) PhX이고; 단, 각 R17및 R18의 발생은 같거나 서로 다르며; PhX-NH2는 (a) (C1-C4)알킬, (b)클로로, (c)플루오로, (d)브로모, (e)니트로, (f)트리플루오로 메틸, 또는(g)OR4중 1-3으로 부가적으로 치환된 아미노-치환 패닐기이고; R4는 (a) 수소 또는 (b) (C1-C4)알킬이고; W는 (a) OCH3또는 (b) S(O)qY(여기서, q는 0,1 또는 2이고; Y는 (a) (C1-C4)알킬 (b) (C1-C4)알케닐, (c, PhX 임이고; W가 S(O)qY일때 Z은 (a) 수소 또는 (b) (C1-C4)알킬이고; W가 OCH3일때 Z는 (C1-C|4)알킬이며; 단, Z이 수소일때, D는 에틸렌이고, R1및 R3가 수소일때, R2는 패닐이고 W는 SCH또는 SPh 이거나; R1및 R2가 메틸일때, R3는 수소이고 W는 SCH3이거나; R1이 수소일때, R2는 패닐이고, R3는 COCH3이고 W는 SCH3이다.
- 제1항에 있어서, R3가 CH3또는 COCH3인 화합물.
- 제1항에 있어서, R2가 COCH3, C6H5, C2H5, CH=CH2및 C4H9으로 구성된 군중에서 선택되는 화합물.
- 제1항에 있어서, R1이 수소, OH, OC2H5, C2H5, CH|3, CO2C2H5로 구성된 군중에서 선택되는 화합물.
- 제1항에 있어서, D가 산소 또는 CH=CH인 화합물.
- 제1항에 있어서, Z가 수소인 화합물.
- 제1항에 있어서, W가 S(O)qY(여기서 q는 0이고 Y는 CH3임)인 화합물.
- 제1항에 있어서, a)5-에테닐-6-에톡시-7-(메틸티오)-4-벤조푸라놀 아세테이트; b) 1-[6-하드록시-4-메톡시-7-(메틸티오)-5-벤조푸라닐]에타논;c) 5-부틸-7-(메틸티오)-4-벤조푸라놀 아세테이트; d)7-(메틸티오)-5-페닐-4-벤조푸라놀 아세테이트; e)4-(메틸티오)-2-페닐-1-나프탈레놀 아세테이트; f)2-부틸-4-(메틸티오)-1-나프탈레놀 아세테이트; 또는 g) 2-부틸-4-(메틸슬포닐)-1-나프탈레놀 아세테이트인 화합물.
- 제1항에 있어서, W가 OCH3인 화합물.
- 제9항에 있어서, (a) 5,6-디에틸-4-히드록시-7-메톡시-2-메틸 벤조푸란; 또는 (b) 5-n-부틸-4-히드록시-7-메톡시-2-메틸 벤조푸란인 화합물.
- 점액 과다분비를 치료하거나 예방하기에 효과적인 양인 하기 일반식 I의 화합물 또는 약리학적으로 허용가능한 그들의 산 부가염을 환자에게 투여하는 것으로 구성된, 그들이 필요한 환자의 기도내에서의 점액의 과다분비를 치료하거나 예방하는 방법;상기식에서, R1및 R2는 같거나 서로 다르며, (a) 수소 (b) (C1-C10)알킬, 또는 (d) PhX(여기서, (PhX)는 (a)(C1-C4)알킬, (b)클로로, (c)플루오로, (d)플루오로, (d)브로모, (e)니트로, (f)트리플루오로메틸, 또는 OR4중 0-3으로 치환된 페닐 임]이며; D는 (a) -CH=CH- (b) -N(CH3) (c) -S-, 또는 (d) -O-이고; R3는 (a)CH3-(CO)- (b) 수소 (c) -C(O)-(CR17R18)m-(CH2)n-NR|14R15(d) -C(O)-AA, 또는 (e) -C(O)-PhX-NH2이고; 상기식들에서, m은 1,2,3 또는 4이고; n은 0,1,2,3,4 또는 5이고; -C(O)AA는 임의의 천연 생성 알파-아미노산으로 부터 유도된 아실부분이고; R14및 R15는 같거나 서로 다르며; (a) 수소 (C1-C10)알킬 (c) -C(O)-R16, (d)-C(O)-PhX, 또는 (e)-PhX이고; 단, n이 0일때 R14및 R15는 수소가 아니며; R16은 (C1-C4)알킬이고; R17및 R18은 같거나 서로 다르며; (a)수소 (b) (C1-C10)알킬 (c) -CH|2-PhX 또는 (d) PhX이고; 단, 각 R17및 R18의 발생은 같거나 서로 다르며; PhX-NH2는 (a) (C|1-C4) 알킬, (b) 클로로, (c)플루오로, (d)브로모, (e)니트로, (f)트리플루오로메틸, 또는 (g)OR4중1-3으로 부가적으로 치환된 아미노-치환 페닐기이고; R4는(a)수소 또는 (b) (C1-C4) 알킬이고; W는 (a) OCH3또는 (b) S(O)qY (여기서, q는 0,1 또는 2이고; Y는 (a) (C1-C4)알킬 (b) (C1-C4)알케닐, (c)PhX 임)이고; W가 S(O)|qY일때 Z은 (a)수소 또는 (b) (C1-C4) 알킬이고; W가 OCH3일때 Z는 (C1-C4)알킬이고, D가 -CH-CH 일때 Z는 수소이며; 단, D가 -CH-CH 또는 =N(CH3)이고 Z이 수소일때 그리고 D가 0또는 -CH=CH-일때, R3는 COCH3이고, Z는 수소이고, R1및 R2는 모두 에틸 페닐 또는 페닐 및 메틸 또는 에틸에스테르이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25046288A | 1988-09-28 | 1988-09-28 | |
| US07/250,462 | 1988-09-28 | ||
| PCT/US1989/003492 WO1990003374A1 (en) | 1988-09-28 | 1989-08-18 | 1,4-dihydrothionapthoquinone and heterocyclic congeners which inhibit lipoxygenase enzymes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR900701771A true KR900701771A (ko) | 1990-12-04 |
Family
ID=22947853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900701139A KR900701771A (ko) | 1988-09-28 | 1989-08-18 | 리폭시게나아제 효소를 억제하는 1, 4-디히드로티오나프토퀴논 및 헤테로시클릭 협동 작용물 |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR900701771A (ko) |
| AU (1) | AU4203789A (ko) |
| WO (1) | WO1990003374A1 (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EE200100097A (et) | 1998-08-18 | 2002-06-17 | The Regents Of The University Of California | Hingamisteede lima tootmise tõkestamine EGF-R antagonistide manustamise teel |
| US7354894B2 (en) | 1998-08-18 | 2008-04-08 | The Regents Of The University Of California | Preventing airway mucus production by administration of EGF-R antagonists |
| US7226661B2 (en) | 2003-02-03 | 2007-06-05 | Board Of Regents, The University Of Texas System | Synthesis of quinones and phenols on solid support |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6054883A (ja) * | 1983-09-05 | 1985-03-29 | Fuji Photo Film Co Ltd | 記録材料 |
| DE3484867D1 (de) * | 1983-12-14 | 1991-09-05 | Upjohn Co | Substituierte naphthalene, indole, benzofurane und benzothiophene als lypoxygenase-inhibitoren. |
| CA1281325C (en) * | 1984-06-20 | 1991-03-12 | Patrice C. Belanger | Benzofuran derivatives |
| JPS61118289A (ja) * | 1984-11-14 | 1986-06-05 | Kanzaki Paper Mfg Co Ltd | 感熱記録体 |
| US4833164A (en) * | 1985-05-08 | 1989-05-23 | E. I. Du Pont De Nemours And Company | 2-substituted-1-naphthols, pharmaceutical compositions of, and their use as 5-lipoxygenase inhibitors |
-
1989
- 1989-08-18 AU AU42037/89A patent/AU4203789A/en not_active Abandoned
- 1989-08-18 KR KR1019900701139A patent/KR900701771A/ko not_active Application Discontinuation
- 1989-08-18 WO PCT/US1989/003492 patent/WO1990003374A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU4203789A (en) | 1990-04-18 |
| WO1990003374A1 (en) | 1990-04-05 |
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