JPS60146857A - α−ハロ芳香族アミドカルボン酸誘導体及びこの化合物より成る抗アレルギ−剤 - Google Patents
α−ハロ芳香族アミドカルボン酸誘導体及びこの化合物より成る抗アレルギ−剤Info
- Publication number
- JPS60146857A JPS60146857A JP24954883A JP24954883A JPS60146857A JP S60146857 A JPS60146857 A JP S60146857A JP 24954883 A JP24954883 A JP 24954883A JP 24954883 A JP24954883 A JP 24954883A JP S60146857 A JPS60146857 A JP S60146857A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid derivative
- represented
- carboxylic acid
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 16
- 230000003266 anti-allergic effect Effects 0.000 title abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 11
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- -1 amide carboxylic acid derivative Chemical class 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000000043 antiallergic agent Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 18
- 239000002904 solvent Substances 0.000 abstract description 18
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 abstract description 15
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 abstract description 15
- 238000002360 preparation method Methods 0.000 abstract description 13
- 230000002401 inhibitory effect Effects 0.000 abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 238000010438 heat treatment Methods 0.000 abstract description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 20
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- 239000000203 mixture Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000000862 absorption spectrum Methods 0.000 description 13
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
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- 238000002844 melting Methods 0.000 description 10
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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- 230000002140 halogenating effect Effects 0.000 description 5
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 4
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 4
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
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- 238000001914 filtration Methods 0.000 description 3
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RDEYORKJEDLLDB-DQVHGTJVSA-N 5-Hydroperoxyeicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C(\OO)=C\C=C\C(O)=O RDEYORKJEDLLDB-DQVHGTJVSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
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- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- ZUYVAEFYQVUCEP-UHFFFAOYSA-N 2,3-dibromo-3-(3,4-dimethoxyphenyl)propanoic acid Chemical compound COC1=CC=C(C(Br)C(Br)C(O)=O)C=C1OC ZUYVAEFYQVUCEP-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 229940124125 5 Lipoxygenase inhibitor Drugs 0.000 description 1
- KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 1
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- 102100025053 Cell division control protein 45 homolog Human genes 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- 210000004072 lung Anatomy 0.000 description 1
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- VGXVLVNJSSONHX-UHFFFAOYSA-N methyl 2-(propanoylamino)benzoate Chemical compound CCC(=O)NC1=CC=CC=C1C(=O)OC VGXVLVNJSSONHX-UHFFFAOYSA-N 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24954883A JPS60146857A (ja) | 1983-12-30 | 1983-12-30 | α−ハロ芳香族アミドカルボン酸誘導体及びこの化合物より成る抗アレルギ−剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24954883A JPS60146857A (ja) | 1983-12-30 | 1983-12-30 | α−ハロ芳香族アミドカルボン酸誘導体及びこの化合物より成る抗アレルギ−剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60146857A true JPS60146857A (ja) | 1985-08-02 |
| JPH0414102B2 JPH0414102B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-03-11 |
Family
ID=17194625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24954883A Granted JPS60146857A (ja) | 1983-12-30 | 1983-12-30 | α−ハロ芳香族アミドカルボン酸誘導体及びこの化合物より成る抗アレルギ−剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60146857A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4993335A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-01-18 | 1974-09-05 | ||
| JPS50111041A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-15 | 1975-09-01 | ||
| JPS50135046A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-17 | 1975-10-25 | ||
| JPS50135047A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-16 | 1975-10-25 | ||
| JPS50140413A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-18 | 1975-11-11 | ||
| JPS511438A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | |
| JPS5384937A (en) * | 1977-06-29 | 1978-07-26 | Kissei Pharmaceut Co Ltd | Preparation of novel aromatic carboxylic acid amide derivatives |
-
1983
- 1983-12-30 JP JP24954883A patent/JPS60146857A/ja active Granted
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4993335A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-01-18 | 1974-09-05 | ||
| JPS50111041A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-15 | 1975-09-01 | ||
| JPS50135047A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-16 | 1975-10-25 | ||
| JPS50135046A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-17 | 1975-10-25 | ||
| JPS50140413A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-18 | 1975-11-11 | ||
| JPS511438A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | |
| JPS5384937A (en) * | 1977-06-29 | 1978-07-26 | Kissei Pharmaceut Co Ltd | Preparation of novel aromatic carboxylic acid amide derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0414102B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-03-11 |
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