JPH0318613B2 - - Google Patents
Info
- Publication number
- JPH0318613B2 JPH0318613B2 JP17997682A JP17997682A JPH0318613B2 JP H0318613 B2 JPH0318613 B2 JP H0318613B2 JP 17997682 A JP17997682 A JP 17997682A JP 17997682 A JP17997682 A JP 17997682A JP H0318613 B2 JPH0318613 B2 JP H0318613B2
- Authority
- JP
- Japan
- Prior art keywords
- cis
- dimethoxycinnamoyl
- anthranilic acid
- tranilast
- compound
- 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.)
- Expired
Links
- NZHGWWWHIYHZNX-CSKARUKUSA-N tranilast Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-CSKARUKUSA-N 0.000 claims description 17
- NZHGWWWHIYHZNX-NTMALXAHSA-N 2-[[(z)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1\C=C/C(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-NTMALXAHSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000000043 antiallergic agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 18
- 239000003814 drug Substances 0.000 description 15
- 229940079593 drug Drugs 0.000 description 15
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 14
- 229960005342 tranilast Drugs 0.000 description 12
- 229960001340 histamine Drugs 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000008602 contraction Effects 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 210000003630 histaminocyte Anatomy 0.000 description 3
- 210000003405 ileum Anatomy 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 231100000668 minimum lethal dose Toxicity 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 210000005194 mastoid cells Anatomy 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- -1 3,4-dimethoxycinnamoyl Chemical group 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920002055 compound 48/80 Polymers 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229940018158 hydroxypropylcellulose 5 mg Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940066827 pertussis vaccine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17997682A JPS5970654A (ja) | 1982-10-15 | 1982-10-15 | アントラニル酸誘導体 |
| AU20100/83A AU2010083A (en) | 1982-10-15 | 1983-10-12 | Anthranilic acid derivative |
| IL69956A IL69956A0 (en) | 1982-10-15 | 1983-10-12 | Anthranilic acid derivatives,their production and pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17997682A JPS5970654A (ja) | 1982-10-15 | 1982-10-15 | アントラニル酸誘導体 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11810283A Division JPS5970655A (ja) | 1983-07-01 | 1983-07-01 | アントラニル酸誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5970654A JPS5970654A (ja) | 1984-04-21 |
| JPH0318613B2 true JPH0318613B2 (fr) | 1991-03-13 |
Family
ID=16075272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17997682A Granted JPS5970654A (ja) | 1982-10-15 | 1982-10-15 | アントラニル酸誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5970654A (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4587356A (en) * | 1981-09-01 | 1986-05-06 | Kissei Pharmaceutical Co., Ltd. | Process for the production of nuclear substituted cinnamoylanthranilic acid derivatives |
| JPS60214766A (ja) * | 1984-04-04 | 1985-10-28 | Terumo Corp | アミド誘導体およびこれを有効成分として含有する５−リポキシゲナ−ゼ作用阻害剤 |
| WO1999007670A1 (fr) * | 1997-08-05 | 1999-02-18 | American Home Products Corporation | Analogues d'acide anthranilique |
| CN1273579A (zh) * | 1997-08-05 | 2000-11-15 | 美国家用产品公司 | 氨茴酸类似物 |
| US6127392A (en) * | 1997-08-05 | 2000-10-03 | American Home Products Corporation | Anthranilic acid analogs |
| WO2004017953A1 (fr) * | 2002-08-21 | 2004-03-04 | Kissei Pharmaceutical Co., Ltd. | Composition therapeutique preventive utilisee en cas de fatigue musculaire, d'elongation musculaire et de maladies attribuees a celles-ci |
| JP6108309B2 (ja) | 2011-02-22 | 2017-04-05 | サン パテント トラスト | 動画像符号化方法、動画像符号化装置、動画像復号方法、および、動画像復号装置 |
-
1982
- 1982-10-15 JP JP17997682A patent/JPS5970654A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5970654A (ja) | 1984-04-21 |
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