JPS5933277A - ３−（２−（４−フエニルピペラジニルエチル）アニリノ）イソベンゾフラノン、その製法及び治療剤としての使用 - Google Patents
３−（２−（４−フエニルピペラジニルエチル）アニリノ）イソベンゾフラノン、その製法及び治療剤としての使用Info
- Publication number
- JPS5933277A JPS5933277A JP58135681A JP13568183A JPS5933277A JP S5933277 A JPS5933277 A JP S5933277A JP 58135681 A JP58135681 A JP 58135681A JP 13568183 A JP13568183 A JP 13568183A JP S5933277 A JPS5933277 A JP S5933277A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- protons
- product
- compound
- anilino
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- WNKNIXLLQAOGBI-UHFFFAOYSA-N 3-[2-[2-(4-phenylpiperazin-1-yl)ethyl]anilino]-3h-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)OC1NC1=CC=CC=C1CCN(CC1)CCN1C1=CC=CC=C1 WNKNIXLLQAOGBI-UHFFFAOYSA-N 0.000 title description 2
- 238000002560 therapeutic procedure Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 238000004454 trace mineral analysis Methods 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 2-(phenylpiperazinylethyl)anilinoisobenzofuranone Chemical compound 0.000 description 2
- JCELPPMEPCQJEB-UHFFFAOYSA-N 2-[2-(4-phenylpiperazin-1-yl)ethyl]aniline Chemical compound NC1=CC=CC=C1CCN1CCN(C=2C=CC=CC=2)CC1 JCELPPMEPCQJEB-UHFFFAOYSA-N 0.000 description 2
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- 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 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 230000002804 anti-anaphylactic effect Effects 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000001705 anti-serotonergic effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- GSXSOFKYQADGGS-UHFFFAOYSA-N 2-[2-(4-fluoropiperazin-1-yl)-2-phenylethyl]aniline Chemical compound NC1=CC=CC=C1CC(C=1C=CC=CC=1)N1CCN(F)CC1 GSXSOFKYQADGGS-UHFFFAOYSA-N 0.000 description 1
- WPOZDEAUSCPSGF-UHFFFAOYSA-N 2-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]aniline Chemical compound CC1=CC=CC=C1N1CCN(CCC=2C(=CC=CC=2)N)CC1 WPOZDEAUSCPSGF-UHFFFAOYSA-N 0.000 description 1
- HVXXOIGTXJOVON-UHFFFAOYSA-N 6-formyl-2,3-dimethoxybenzoic acid Chemical compound COC1=CC=C(C=O)C(C(O)=O)=C1OC HVXXOIGTXJOVON-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 101100366130 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD6 gene Proteins 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 201000005505 Measles Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003326 anti-histaminergic effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical class C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229920002055 compound 48/80 Polymers 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 201000003152 motion sickness Diseases 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000035485 pulse pressure Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 206010040400 serum sickness Diseases 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 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
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/90—Benzo [c] furans; Hydrogenated benzo [c] furans with an oxygen atom in position 1 and a nitrogen atom in position 3, or vice versa
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8213446 | 1982-07-29 | ||
| FR8213446A FR2531082A1 (fr) | 1982-07-29 | 1982-07-29 | Nouvelles ((phenyl-4 piperazinylethyl)-2-anilino)-3 isobenzofurannones, leur methode de preparation et leur application therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5933277A true JPS5933277A (ja) | 1984-02-23 |
Family
ID=9276532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58135681A Pending JPS5933277A (ja) | 1982-07-29 | 1983-07-25 | ３−（２−（４−フエニルピペラジニルエチル）アニリノ）イソベンゾフラノン、その製法及び治療剤としての使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4590193A (enExample) |
| EP (1) | EP0100745B1 (enExample) |
| JP (1) | JPS5933277A (enExample) |
| CA (1) | CA1228071A (enExample) |
| DE (1) | DE3362265D1 (enExample) |
| ES (1) | ES8500257A1 (enExample) |
| FR (1) | FR2531082A1 (enExample) |
| MA (1) | MA19834A1 (enExample) |
| OA (1) | OA07511A (enExample) |
| PT (1) | PT77121B (enExample) |
| ZA (1) | ZA834932B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5219855A (en) * | 1988-01-29 | 1993-06-15 | Mitsubishi Kasei Corporation | Anxiolytic drug |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR30F (fr) * | 1959-10-20 | 1963-04-05 | May & Baker Ltd | Nouvelles pipérazines n-n disusbstituées. |
| GB971041A (en) * | 1960-02-02 | 1964-09-30 | May & Baker Ltd | New phenylpiperazine compounds |
| BE794081A (fr) * | 1972-01-27 | 1973-05-16 | Cortial | Nouveaux produits de reaction entre une amine primaire et un aldehyde |
-
1982
- 1982-07-29 FR FR8213446A patent/FR2531082A1/fr active Granted
-
1983
- 1983-05-19 EP EP83450013A patent/EP0100745B1/fr not_active Expired
- 1983-05-19 DE DE8383450013T patent/DE3362265D1/de not_active Expired
- 1983-07-01 MA MA20054A patent/MA19834A1/fr unknown
- 1983-07-06 ES ES523919A patent/ES8500257A1/es not_active Expired
- 1983-07-06 ZA ZA834932A patent/ZA834932B/xx unknown
- 1983-07-22 CA CA000432970A patent/CA1228071A/en not_active Expired
- 1983-07-25 JP JP58135681A patent/JPS5933277A/ja active Pending
- 1983-07-27 US US06/517,653 patent/US4590193A/en not_active Expired - Fee Related
- 1983-07-28 PT PT77121A patent/PT77121B/pt not_active IP Right Cessation
- 1983-07-29 OA OA58078A patent/OA07511A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0100745A1 (fr) | 1984-02-15 |
| MA19834A1 (fr) | 1984-04-01 |
| ES523919A0 (es) | 1984-10-01 |
| ZA834932B (en) | 1984-04-25 |
| DE3362265D1 (en) | 1986-04-03 |
| PT77121A (fr) | 1983-08-01 |
| CA1228071A (en) | 1987-10-13 |
| EP0100745B1 (fr) | 1986-02-26 |
| PT77121B (fr) | 1986-01-27 |
| ES8500257A1 (es) | 1984-10-01 |
| FR2531082A1 (fr) | 1984-02-03 |
| OA07511A (fr) | 1985-03-31 |
| FR2531082B1 (enExample) | 1985-03-08 |
| US4590193A (en) | 1986-05-20 |
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