FR2531082A1 - Nouvelles ((phenyl-4 piperazinylethyl)-2-anilino)-3 isobenzofurannones, leur methode de preparation et leur application therapeutique - Google Patents
Nouvelles ((phenyl-4 piperazinylethyl)-2-anilino)-3 isobenzofurannones, leur methode de preparation et leur application therapeutique Download PDFInfo
- Publication number
- FR2531082A1 FR2531082A1 FR8213446A FR8213446A FR2531082A1 FR 2531082 A1 FR2531082 A1 FR 2531082A1 FR 8213446 A FR8213446 A FR 8213446A FR 8213446 A FR8213446 A FR 8213446A FR 2531082 A1 FR2531082 A1 FR 2531082A1
- Authority
- FR
- France
- Prior art keywords
- cor
- protons
- ppm
- anilino
- formula
- 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
- 230000001225 therapeutic effect Effects 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 206010020772 Hypertension Diseases 0.000 claims abstract 2
- 231100000252 nontoxic Toxicity 0.000 claims abstract 2
- 230000003000 nontoxic effect Effects 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 230000000172 allergic effect Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000002547 new drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- -1 PHENYL-4 PIPERAZINYLETHYL Chemical class 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 5
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract description 2
- 239000012458 free base Substances 0.000 abstract description 2
- 206010027654 Allergic conditions Diseases 0.000 abstract 1
- HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical class [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000004452 microanalysis Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
- 230000001387 anti-histamine Effects 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
- 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
- 208000003455 anaphylaxis Diseases 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 206010002198 Anaphylactic reaction Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000036783 anaphylactic response Effects 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229940076279 serotonin Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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
- 241000700199 Cavia porcellus Species 0.000 description 2
- 201000004624 Dermatitis Diseases 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
- 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 2
- 230000002804 anti-anaphylactic effect Effects 0.000 description 2
- 230000001705 anti-serotonergic effect Effects 0.000 description 2
- 230000000794 anti-serotonin Effects 0.000 description 2
- 239000003420 antiserotonin agent Substances 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 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 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- XLOCXHGERCHFGM-UHFFFAOYSA-N 4-[2-(4-phenylpiperazin-1-yl)ethyl]aniline Chemical compound C1=CC(N)=CC=C1CCN1CCN(C=2C=CC=CC=2)CC1 XLOCXHGERCHFGM-UHFFFAOYSA-N 0.000 description 1
- XASBQYNRXJJDQH-UHFFFAOYSA-N 4-phenyl-N-(2-piperazin-1-ylethyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NCCN1CCNCC1 XASBQYNRXJJDQH-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
- 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
- 208000003251 Pruritus Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 208000006673 asthma 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
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000009109 curative therapy Methods 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
- 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
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 210000003692 ilium Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration 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
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229960003910 promethazine Drugs 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
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 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
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)
Priority Applications (11)
| 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 |
| EP83450013A EP0100745B1 (fr) | 1982-07-29 | 1983-05-19 | Nouvelles ((phényl-4 pipérazinyléthyl)-2 aniline)-3 isobenzofurannones, leur méthode de préparation et leur application thérapeutique |
| DE8383450013T DE3362265D1 (en) | 1982-07-29 | 1983-05-19 | 3-2-(4-phenylpiperazinyl)-ethyl-anilino)isobenzofuranones, their preparation and their medicinal use |
| MA20054A MA19834A1 (fr) | 1982-07-29 | 1983-07-01 | Nouvelles ( phenyl-4 piperazinylethyl -2 aniline ) 3 isobenzofurannones, leur methode de preparation et leur application therapeutique . |
| ZA834932A ZA834932B (en) | 1982-07-29 | 1983-07-06 | Novel 3-(2-(4-phenylpiperazinylethyl)-anilino)-isobenzofuranones,method for their preparation and their application in therapy |
| ES523919A ES8500257A1 (es) | 1982-07-29 | 1983-07-06 | Procedimiento de obtencion de nuevas benzoiso furanonas y de sus sales de adicion no toxicas. |
| CA000432970A 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 |
| JP58135681A 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 |
| US06/517,653 US4590193A (en) | 1982-07-29 | 1983-07-27 | 3-(2-(4-phenylpiperazinylethyl)anilino)-isobenzofuranones, their method of preparation and their use as antihypertensive and antiallergic drugs |
| PT77121A PT77121B (fr) | 1982-07-29 | 1983-07-28 | Procede pour preparer nouvelles <(phenyl-4 piperazinylethyl)-2 anilide>-3 isobenzofurannones |
| OA58078A OA07511A (fr) | 1982-07-29 | 1983-07-29 | Nouvelle((phényl-4 pipérazinyléthyl)-2 aniline)-3 isobenzofurannones, leur méthode de préparation et leur application thérapeutique. |
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2531082A1 true FR2531082A1 (fr) | 1984-02-03 |
| FR2531082B1 FR2531082B1 (enExample) | 1985-03-08 |
Family
ID=9276532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8213446A Granted FR2531082A1 (fr) | 1982-07-29 | 1982-07-29 | Nouvelles ((phenyl-4 piperazinylethyl)-2-anilino)-3 isobenzofurannones, leur methode de preparation et leur application therapeutique |
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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH398614A (fr) * | 1960-02-02 | 1966-03-15 | May & Baker Ltd | Procédé de préparation de nouveaux dérivés de la pipérazine |
| FR2168931A1 (enExample) * | 1972-01-27 | 1973-09-07 | Cortial |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR30F (fr) * | 1959-10-20 | 1963-04-05 | May & Baker Ltd | Nouvelles pipérazines n-n disusbstituées. |
-
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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH398614A (fr) * | 1960-02-02 | 1966-03-15 | May & Baker Ltd | Procédé de préparation de nouveaux dérivés de la pipérazine |
| FR2168931A1 (enExample) * | 1972-01-27 | 1973-09-07 | Cortial |
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 |
| JPS5933277A (ja) | 1984-02-23 |
| ES8500257A1 (es) | 1984-10-01 |
| OA07511A (fr) | 1985-03-31 |
| FR2531082B1 (enExample) | 1985-03-08 |
| US4590193A (en) | 1986-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2673182A1 (fr) | Piperazines n,n'-disubstituees, leur procede de preparation et leur application en therapeutique. | |
| EP0254627A1 (fr) | Dérivés de la benzhydryloxyéthylpipérazine, procédés d'obtention et compositions pharmaceutiques les contenant | |
| EP0092479B1 (fr) | Polymethylène diamines, n,n'-substituées, leurs procédés de préparation et les compositions pharmaceutiques les renfermant | |
| US3953604A (en) | 1-(2-Substituted-chromonyloxy)-2-hydroxy-3-(substituted phenoxy)propanes | |
| FR2531082A1 (fr) | Nouvelles ((phenyl-4 piperazinylethyl)-2-anilino)-3 isobenzofurannones, leur methode de preparation et leur application therapeutique | |
| EP0079810B1 (fr) | Nouveaux dérivés de la phényl-4 quinazoline actifs sur le système nerveux central | |
| JPS60224686A (ja) | 置換４‐ヒドロキシ‐ベンゾピラン類、その製法および用途 | |
| EP0106776B1 (fr) | Nouvelles amino-2 aminométhyl-5 oxazolines-2 | |
| EP0078757B1 (fr) | Nouvelles imines dérivées de (phényl-4 pipérazinyléthyl)-2 anilines, leur méthode de préparation, ainsi que leur emploi en thérapeutique | |
| EP0078756B1 (fr) | Nouvelles (phényl-4 pipérazinyléthyl)-2 anilines, leur méthode de préparation, ainsi que leur emploi en thérapeutique | |
| EP0259227A1 (fr) | Dérivés de la benzhydryloxyéthyl-pipéridine, procédé d'obtention et compositions pharmaceutiques les contenant | |
| KR910003711B1 (ko) | 2-(n-피롤리디노)-3-이소부톡시-n-치환된 페닐-n-벤질-프로필아민의 제조방법 | |
| WO1982001874A1 (en) | 2-(1,4-benzodoioxan-2-ylalkyl)imidazoles useful as antidepressants | |
| EP0008259A1 (fr) | Nouveaux dérivés de la pipéridylbenzimidazolinone, leurs procédés de préparation et les compositions pharmaceutiques les renfermant | |
| US3970672A (en) | 2,2 Disubstituted-benzodioxoles | |
| CA1263656A (en) | Aryloxycycloalkanolaminoalkylene aryl ketones | |
| US4868315A (en) | Novel aryloxycycloalkanolaminoalkylene aryl ketones | |
| FR2645860A1 (fr) | Nouvelles aryloxymethyl-5 amino-2 oxazolines, syntheses et applications therapeutiques | |
| US3161650A (en) | 2-amino-5-aryloxazoline products | |
| FR2494269A1 (fr) | Nouveaux produits de condensation entre l'acide acetylsalicylique et la piperazine, leur procede de preparation et leur application en therapeutique | |
| SU1416055A3 (ru) | Способ получени сложных эфиров N-замещенной о-аминобензойной кислоты | |
| JPS59500518A (ja) | 新規シアノグアニジン類、その製造法およびこれらを含有する薬理組成物 | |
| FR2504532A1 (fr) | Nouveaux derives heterocycliques du type benzimidazole, indole et purine, leur procede de preparation et leur application en therapeutique | |
| BE893479A (fr) | Nouveaux derives d'amino-2 phenethylamines, leur methode de preparation et leur application therapeutique | |
| EP0022737B1 (fr) | Imines dérivées de l'amino-5 benzodioxole-1,3 utiles comme médicaments et leur préparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |