FR2515647A1 - Nouvelles imines derivees de (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique - Google Patents
Nouvelles imines derivees de (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique Download PDFInfo
- Publication number
- FR2515647A1 FR2515647A1 FR8120563A FR8120563A FR2515647A1 FR 2515647 A1 FR2515647 A1 FR 2515647A1 FR 8120563 A FR8120563 A FR 8120563A FR 8120563 A FR8120563 A FR 8120563A FR 2515647 A1 FR2515647 A1 FR 2515647A1
- Authority
- FR
- France
- Prior art keywords
- ppm
- phenyl
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- chain
- product
- 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
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- -1 PHENYL-4 PIPERAZINYLETHYL Chemical class 0.000 title abstract description 6
- 150000002466 imines Chemical class 0.000 title abstract description 5
- 230000001225 therapeutic effect Effects 0.000 title abstract 2
- 230000000506 psychotropic effect Effects 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 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 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 239000002547 new drug Substances 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 229910052736 halogen Chemical group 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
- 150000001299 aldehydes Chemical class 0.000 abstract description 4
- 150000001448 anilines Chemical class 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical class F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229920000136 polysorbate Polymers 0.000 description 7
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000003756 stirring Methods 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-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
- 241000700159 Rattus Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- 150000001860 citric acid derivatives Chemical class 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 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
- 241000699670 Mus sp. Species 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 230000002804 anti-anaphylactic effect Effects 0.000 description 2
- 230000001705 anti-serotonergic effect Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 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
- 101100243951 Caenorhabditis elegans pie-1 gene Proteins 0.000 description 1
- 241000700199 Cavia porcellus Species 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
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010042008 Stereotypy Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000556 agonist Substances 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
- 230000008485 antagonism Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 230000015572 biosynthetic process Effects 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
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 201000003152 motion sickness Diseases 0.000 description 1
- 230000037023 motor activity Effects 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
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 206010040400 serum sickness Diseases 0.000 description 1
- 238000001228 spectrum Methods 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
- 238000003786 synthesis reaction Methods 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8120563A FR2515647A1 (fr) | 1981-11-03 | 1981-11-03 | Nouvelles imines derivees de (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique |
| EP82450015A EP0078757B1 (fr) | 1981-11-03 | 1982-10-27 | Nouvelles imines dérivées de (phényl-4 pipérazinyléthyl)-2 anilines, leur méthode de préparation, ainsi que leur emploi en thérapeutique |
| DE8282450015T DE3266055D1 (en) | 1981-11-03 | 1982-10-27 | Imines of 2-(4-phenyl-piperazinylethyl) anilines, process for their preparation and their use in medicine |
| MA19844A MA19632A1 (fr) | 1981-11-03 | 1982-11-01 | Nouvelles imines de (phenyl-4 piperazinylethyl)-2 anilines, leur preparation et leur emploi en tant que medicament |
| JP57192339A JPS58126866A (ja) | 1981-11-03 | 1982-11-01 | （フエニル−４ピペラジニルエチル）−２アニリンより誘導された新規のイミン、その製法及び治療剤としての使用 |
| PT75776A PT75776B (en) | 1981-11-03 | 1982-11-02 | Process for the preparation of new imines derived from (phenyl-4 piperaziniletyl)-2 anilines |
| CA000414678A CA1199917A (fr) | 1981-11-03 | 1982-11-02 | Imines derivees de 2-(4-phenylpiperazinylethyl) anilines |
| OA57836A OA07243A (fr) | 1981-11-03 | 1982-11-03 | Nouvelles imines de (phényl-4 pipérazinyléthyl)-2 anilines leur préparation et leur emploi comme médicament. |
| ZA828043A ZA828043B (en) | 1981-11-03 | 1982-11-03 | Novel amines of(phenyl-4 piperazinylethyl)-2 anilines,their preparation and use in medicaments |
| ES517095A ES517095A0 (es) | 1981-11-03 | 1982-11-03 | Procedimiento de preparacion de nuevas iminas derivadas de 2-(4-fenilpiperaziniletil) anilinas, asi como de sus sales de adicion no toxicas. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8120563A FR2515647A1 (fr) | 1981-11-03 | 1981-11-03 | Nouvelles imines derivees de (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2515647A1 true FR2515647A1 (fr) | 1983-05-06 |
| FR2515647B1 FR2515647B1 (enExample) | 1984-08-24 |
Family
ID=9263639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8120563A Granted FR2515647A1 (fr) | 1981-11-03 | 1981-11-03 | Nouvelles imines derivees de (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0078757B1 (enExample) |
| JP (1) | JPS58126866A (enExample) |
| CA (1) | CA1199917A (enExample) |
| DE (1) | DE3266055D1 (enExample) |
| ES (1) | ES517095A0 (enExample) |
| FR (1) | FR2515647A1 (enExample) |
| MA (1) | MA19632A1 (enExample) |
| OA (1) | OA07243A (enExample) |
| PT (1) | PT75776B (enExample) |
| ZA (1) | ZA828043B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2559481B1 (fr) * | 1984-02-10 | 1988-01-08 | Rhone Poulenc Agrochimie | Nouveaux derives de phenyliminomethyl-3 pyridine, leur preparation et leur utilisation pour la preparation de derives de pyridylacetonitriles utilisables comme antifongiques |
| 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 |
| FR2692264B1 (fr) * | 1992-06-12 | 1994-08-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les contenant. |
| GB2499991A (en) | 2012-03-05 | 2013-09-11 | Solaredge Technologies Ltd | DC link circuit for photovoltaic array |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2476644A1 (fr) * | 1980-02-21 | 1981-08-28 | Sarget Lab | Orthoarylydeneaminophenethylamine, leur preparation et leur utilisation therapeutique |
-
1981
- 1981-11-03 FR FR8120563A patent/FR2515647A1/fr active Granted
-
1982
- 1982-10-27 EP EP82450015A patent/EP0078757B1/fr not_active Expired
- 1982-10-27 DE DE8282450015T patent/DE3266055D1/de not_active Expired
- 1982-11-01 JP JP57192339A patent/JPS58126866A/ja active Pending
- 1982-11-01 MA MA19844A patent/MA19632A1/fr unknown
- 1982-11-02 CA CA000414678A patent/CA1199917A/fr not_active Expired
- 1982-11-02 PT PT75776A patent/PT75776B/pt not_active IP Right Cessation
- 1982-11-03 OA OA57836A patent/OA07243A/xx unknown
- 1982-11-03 ZA ZA828043A patent/ZA828043B/xx unknown
- 1982-11-03 ES ES517095A patent/ES517095A0/es active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2476644A1 (fr) * | 1980-02-21 | 1981-08-28 | Sarget Lab | Orthoarylydeneaminophenethylamine, leur preparation et leur utilisation therapeutique |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0078757A1 (fr) | 1983-05-11 |
| ES8401051A1 (es) | 1983-12-01 |
| CA1199917A (fr) | 1986-01-28 |
| PT75776B (en) | 1985-07-26 |
| DE3266055D1 (en) | 1985-10-10 |
| MA19632A1 (fr) | 1983-07-01 |
| ZA828043B (en) | 1983-08-31 |
| ES517095A0 (es) | 1983-12-01 |
| FR2515647B1 (enExample) | 1984-08-24 |
| PT75776A (en) | 1982-12-01 |
| OA07243A (fr) | 1984-04-30 |
| JPS58126866A (ja) | 1983-07-28 |
| EP0078757B1 (fr) | 1985-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |