CA1228071A - ((phenyl-4 piperazinylethyl)-2 anilino)-3 isobenzofuranones, their method of preparation and their use as antihypertensive and antiallergic drugs - Google Patents
((phenyl-4 piperazinylethyl)-2 anilino)-3 isobenzofuranones, their method of preparation and their use as antihypertensive and antiallergic drugsInfo
- Publication number
- CA1228071A CA1228071A CA000432970A CA432970A CA1228071A CA 1228071 A CA1228071 A CA 1228071A CA 000432970 A CA000432970 A CA 000432970A CA 432970 A CA432970 A CA 432970A CA 1228071 A CA1228071 A CA 1228071A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- och3
- protons
- compounds
- 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
- 238000000034 method Methods 0.000 title claims abstract description 23
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical class C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 title abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 230000003276 anti-hypertensive effect Effects 0.000 title description 9
- 239000002220 antihypertensive agent Substances 0.000 title description 3
- 239000000043 antiallergic agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 20
- 206010027654 Allergic conditions Diseases 0.000 abstract description 7
- 206010020772 Hypertension Diseases 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract description 2
- 206010020751 Hypersensitivity Diseases 0.000 abstract 1
- 230000007815 allergy Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 19
- 230000000694 effects Effects 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000004452 microanalysis Methods 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000003266 anti-allergic effect Effects 0.000 description 6
- 230000001387 anti-histamine Effects 0.000 description 6
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 5
- -1 Amine compounds Chemical class 0.000 description 5
- 239000000739 antihistaminic agent Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 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 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 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
- 241000700199 Cavia porcellus Species 0.000 description 3
- 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
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 230000002804 anti-anaphylactic effect Effects 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 description 1
- IURBFWKNFNSBQW-UHFFFAOYSA-N 3-anilino-3h-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)OC1NC1=CC=CC=C1 IURBFWKNFNSBQW-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
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010048768 Dermatosis Diseases 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 208000005279 Status Asthmaticus Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000001705 anti-serotonergic effect Effects 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 229960001140 cyproheptadine Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008196 pharmacological composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 206010040400 serum sickness Diseases 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 |
|---|---|---|---|
| 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 |
| FR82.13.446 | 1982-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1228071A true CA1228071A (en) | 1987-10-13 |
Family
ID=9276532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000432970A Expired CA1228071A (en) | 1982-07-29 | 1983-07-22 | ((phenyl-4 piperazinylethyl)-2 anilino)-3 isobenzofuranones, their method of preparation and their use as antihypertensive and antiallergic drugs |
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 |
| EP0100745B1 (fr) | 1986-02-26 |
| PT77121B (fr) | 1986-01-27 |
| JPS5933277A (ja) | 1984-02-23 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |