FR2515648A1 - Nouvelles (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique - Google Patents
Nouvelles (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique Download PDFInfo
- Publication number
- FR2515648A1 FR2515648A1 FR8120564A FR8120564A FR2515648A1 FR 2515648 A1 FR2515648 A1 FR 2515648A1 FR 8120564 A FR8120564 A FR 8120564A FR 8120564 A FR8120564 A FR 8120564A FR 2515648 A1 FR2515648 A1 FR 2515648A1
- Authority
- FR
- France
- Prior art keywords
- phenyl
- chain
- piperazinylethyl
- products
- preparation
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims abstract description 5
- -1 PHENYL-4 PIPERAZINYLETHYL Chemical class 0.000 title abstract description 8
- 230000001225 therapeutic effect Effects 0.000 title abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 7
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 231100000252 nontoxic Toxicity 0.000 claims abstract 2
- 230000003000 nontoxic effect Effects 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 8
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000002547 new drug Substances 0.000 claims 2
- 206010027654 Allergic conditions Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 abstract description 2
- 239000012458 free base Substances 0.000 abstract description 2
- BLJBDLGFKNXUCB-UHFFFAOYSA-N [2-methyl-2-(nitrooxymethyl)pentyl] nitrate Chemical class [O-][N+](=O)OCC(C)(CCC)CO[N+]([O-])=O BLJBDLGFKNXUCB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229940126601 medicinal product Drugs 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 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 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- 206010033733 Papule Diseases 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 208000003455 anaphylaxis Diseases 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
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FHKIGGSCRYVAMY-UHFFFAOYSA-N 1-(1-bromoethyl)-2-nitrobenzene Chemical compound CC(Br)C1=CC=CC=C1[N+]([O-])=O FHKIGGSCRYVAMY-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 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 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- REYFJDPCWQRWAA-UHFFFAOYSA-N antazoline Chemical compound N=1CCNC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 REYFJDPCWQRWAA-UHFFFAOYSA-N 0.000 description 1
- 229960002469 antazoline Drugs 0.000 description 1
- 230000002804 anti-anaphylactic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000006673 asthma 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
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
- 229960000876 cinnarizine Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 229960001140 cyproheptadine Drugs 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
- 238000010908 decantation Methods 0.000 description 1
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 1
- HCFDWZZGGLSKEP-UHFFFAOYSA-N doxylamine Chemical compound C=1C=CC=NC=1C(C)(OCCN(C)C)C1=CC=CC=C1 HCFDWZZGGLSKEP-UHFFFAOYSA-N 0.000 description 1
- 229960005178 doxylamine Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000003152 motion sickness Diseases 0.000 description 1
- UHNPFYCIROXUQI-UHFFFAOYSA-N n-[2-(4-phenylpiperazin-1-yl)ethyl]aniline Chemical compound C=1C=CC=CC=1NCCN(CC1)CCN1C1=CC=CC=C1 UHNPFYCIROXUQI-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 206010040400 serum sickness Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8120564A FR2515648A1 (fr) | 1981-11-03 | 1981-11-03 | Nouvelles (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique |
| EP82450014A EP0078756B1 (fr) | 1981-11-03 | 1982-10-27 | Nouvelles (phényl-4 pipérazinyléthyl)-2 anilines, leur méthode de préparation, ainsi que leur emploi en thérapeutique |
| DE8282450014T DE3269872D1 (en) | 1981-11-03 | 1982-10-27 | 2-(4-phenyl-piperazinylethyl) anilines, process for their preparation and their use in medicine |
| MA19846A MA19634A1 (fr) | 1981-11-03 | 1982-11-01 | Nouvelles (phenyl -4 piperazinylethyl) -2 aninilines, leur preparation et leur emploi en tant que medicament |
| JP57192340A JPS58126878A (ja) | 1981-11-03 | 1982-11-01 | 新規の（フエニル−４ピペラジニルエチル）−２アニリン、その製法及び治療剤としての使用 |
| CA000414677A CA1210006A (fr) | 1981-11-03 | 1982-11-02 | 2-(4-phenylpiperazinylethyl)anilines |
| PT75775A PT75775B (en) | 1981-11-03 | 1982-11-02 | Process for preparing novel (phenyl-4-piperazinyletyl)-2 anilines |
| ES517096A ES517096A0 (es) | 1981-11-03 | 1982-11-03 | Procedimiento de preparacion de nuevas 2-(4-fenilpiperaziniletil) anilinas, asi como de sus sales de adicion no toxicas. |
| OA57837A OA07244A (fr) | 1981-11-03 | 1982-11-03 | Nouvelles (phényl-4 pipérazinyléthyl)-2 anilines, leur préparation et leur emploi comme médicament. |
| ZA828044A ZA828044B (en) | 1981-11-03 | 1982-11-03 | Novel(phenyl-4 piperazinylethyl)-2 anilines,their preparation and their use in medicaments |
| US06/843,915 US4668681A (en) | 1981-11-03 | 1986-03-21 | 2-(4-Phenylpiperazinylethyl) anilines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8120564A FR2515648A1 (fr) | 1981-11-03 | 1981-11-03 | Nouvelles (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2515648A1 true FR2515648A1 (fr) | 1983-05-06 |
| FR2515648B1 FR2515648B1 (enExample) | 1984-08-24 |
Family
ID=9263640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8120564A Granted FR2515648A1 (fr) | 1981-11-03 | 1981-11-03 | Nouvelles (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4668681A (enExample) |
| EP (1) | EP0078756B1 (enExample) |
| JP (1) | JPS58126878A (enExample) |
| CA (1) | CA1210006A (enExample) |
| DE (1) | DE3269872D1 (enExample) |
| ES (1) | ES517096A0 (enExample) |
| FR (1) | FR2515648A1 (enExample) |
| MA (1) | MA19634A1 (enExample) |
| OA (1) | OA07244A (enExample) |
| PT (1) | PT75775B (enExample) |
| ZA (1) | ZA828044B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8619472D0 (en) * | 1986-08-09 | 1986-09-17 | Pfizer Ltd | Anti-arrhythmia agents |
| US5219855A (en) * | 1988-01-29 | 1993-06-15 | Mitsubishi Kasei Corporation | Anxiolytic drug |
| FR2632641B1 (fr) * | 1988-06-13 | 1990-10-12 | Irceba | ((aryl-4-piperazinyl-1)-2 ethoxy)-3 p-cymene, les derives ortho, meta, para monosubstitues ou disubstitues sur le noyau phenyle dudit produit, le procede de preparation desdits derives, et les medicaments contenant lesdits composes comme principe actif |
Citations (1)
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR78756E (fr) * | 1957-11-22 | 1962-09-07 | Système de sécurité incorporé pour charrue | |
| NL251385A (enExample) * | 1959-12-21 | |||
| GB953005A (en) * | 1961-02-24 | 1964-03-18 | Soc Ind Fab Antibiotiques Sifa | Substituted n-phenylethyl-n-phenyl-piperazines |
| BE620235R (fr) * | 1961-07-14 | 1963-01-14 | May & Baker Ltd | Nouvelles pipérazines N-N disubstituéer |
| US3562277A (en) * | 1967-09-06 | 1971-02-09 | Shulton Inc | Ketonic derivatives of phenyl piperazines |
| DE2325633A1 (de) * | 1973-05-21 | 1974-12-12 | Boehringer Sohn Ingelheim | Piperazinderivate |
| US3981864A (en) * | 1973-09-08 | 1976-09-21 | Eisai Co., Ltd. | 1,3-Benzodioxol derivatives |
| US4094980A (en) * | 1974-09-03 | 1978-06-13 | Boehringer Ingelheim Gmbh | N-[1-(3',4'-methylenedioxy-phenyl)-propyl-(2)]-N'-phenyl-piperazines and salts thereof |
| FR2476644A1 (fr) * | 1980-02-21 | 1981-08-28 | Sarget Lab | Orthoarylydeneaminophenethylamine, leur preparation et leur utilisation therapeutique |
-
1981
- 1981-11-03 FR FR8120564A patent/FR2515648A1/fr active Granted
-
1982
- 1982-10-27 DE DE8282450014T patent/DE3269872D1/de not_active Expired
- 1982-10-27 EP EP82450014A patent/EP0078756B1/fr not_active Expired
- 1982-11-01 MA MA19846A patent/MA19634A1/fr unknown
- 1982-11-01 JP JP57192340A patent/JPS58126878A/ja active Pending
- 1982-11-02 PT PT75775A patent/PT75775B/pt not_active IP Right Cessation
- 1982-11-02 CA CA000414677A patent/CA1210006A/fr not_active Expired
- 1982-11-03 ES ES517096A patent/ES517096A0/es active Granted
- 1982-11-03 OA OA57837A patent/OA07244A/xx unknown
- 1982-11-03 ZA ZA828044A patent/ZA828044B/xx unknown
-
1986
- 1986-03-21 US US06/843,915 patent/US4668681A/en not_active Expired - Fee Related
Patent Citations (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8307777A1 (es) | 1983-08-01 |
| DE3269872D1 (en) | 1986-04-17 |
| EP0078756A1 (fr) | 1983-05-11 |
| PT75775A (en) | 1982-12-01 |
| FR2515648B1 (enExample) | 1984-08-24 |
| EP0078756B1 (fr) | 1986-03-12 |
| CA1210006A (fr) | 1986-08-19 |
| US4668681A (en) | 1987-05-26 |
| PT75775B (en) | 1985-07-26 |
| JPS58126878A (ja) | 1983-07-28 |
| ES517096A0 (es) | 1983-08-01 |
| ZA828044B (en) | 1983-08-31 |
| MA19634A1 (fr) | 1983-07-01 |
| OA07244A (fr) | 1984-04-30 |
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| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |