DE69329252T2 - Verwendung von piperazinderivaten zur behandlung von kognitiven erkrankungen - Google Patents
Verwendung von piperazinderivaten zur behandlung von kognitiven erkrankungenInfo
- Publication number
- DE69329252T2 DE69329252T2 DE69329252T DE69329252T DE69329252T2 DE 69329252 T2 DE69329252 T2 DE 69329252T2 DE 69329252 T DE69329252 T DE 69329252T DE 69329252 T DE69329252 T DE 69329252T DE 69329252 T2 DE69329252 T2 DE 69329252T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- aryl
- cycloalkyl
- formula
- heteroaryl
- 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 - Fee Related
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 5
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 4
- 201000010099 disease Diseases 0.000 title description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 1
- 230000001149 cognitive effect Effects 0.000 title 1
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 28
- -1 nitrogen-containing heteroaryl radical Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000004885 piperazines Chemical class 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- SBPRIAGPYFYCRT-UHFFFAOYSA-N N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl)cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 SBPRIAGPYFYCRT-UHFFFAOYSA-N 0.000 claims description 2
- UMTDAKAAYOXIKU-UHFFFAOYSA-N N-tert-butyl-3-[4-(2-methoxyphenyl)-1-piperazinyl]-2-phenylpropanamide Chemical compound COC1=CC=CC=C1N1CCN(CC(C(=O)NC(C)(C)C)C=2C=CC=CC=2)CC1 UMTDAKAAYOXIKU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 239000000203 mixture Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 7
- 239000002775 capsule Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000969 carrier Substances 0.000 description 4
- 230000007278 cognition impairment Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 208000026139 Memory disease Diseases 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 208000029028 brain injury Diseases 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003278 mimic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ZHZZWIQPCAMTIM-UHFFFAOYSA-N [C]1=CC=CC2=CC=CC=C12 Chemical compound [C]1=CC=CC2=CC=CC=C12 ZHZZWIQPCAMTIM-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000006931 brain damage Effects 0.000 description 1
- 231100000874 brain damage Toxicity 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000020595 eating behavior Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003825 glutamate receptor antagonist Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002913 oxalic acids Chemical class 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000003727 serotonin 1A antagonist Substances 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000024587 synaptic transmission, glutamatergic Effects 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
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006169 tetracyclic group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929223153A GB9223153D0 (en) | 1992-11-05 | 1992-11-05 | Piperazine derivatives |
| PCT/GB1993/002197 WO1994009780A1 (en) | 1992-11-05 | 1993-10-25 | Use of piperazine derivatives for the treatment of cognitive disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69329252D1 DE69329252D1 (de) | 2000-09-21 |
| DE69329252T2 true DE69329252T2 (de) | 2001-03-29 |
Family
ID=10724559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69329252T Expired - Fee Related DE69329252T2 (de) | 1992-11-05 | 1993-10-25 | Verwendung von piperazinderivaten zur behandlung von kognitiven erkrankungen |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5827847A (enExample) |
| EP (1) | EP0877612B1 (enExample) |
| JP (1) | JP3238153B2 (enExample) |
| AT (1) | ATE195422T1 (enExample) |
| AU (1) | AU682155B2 (enExample) |
| CA (1) | CA2148593C (enExample) |
| DE (1) | DE69329252T2 (enExample) |
| DK (1) | DK0877612T3 (enExample) |
| ES (1) | ES2149216T3 (enExample) |
| GB (1) | GB9223153D0 (enExample) |
| GR (1) | GR3034400T3 (enExample) |
| HU (1) | HUT72049A (enExample) |
| LV (1) | LV12734B (enExample) |
| MX (1) | MX9306879A (enExample) |
| PT (1) | PT877612E (enExample) |
| TW (1) | TW252043B (enExample) |
| WO (1) | WO1994009780A1 (enExample) |
| ZA (1) | ZA937827B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0710481A1 (en) * | 1994-11-02 | 1996-05-08 | Duphar International Research B.V | Use of flesinoxan for cognition enhancement |
| US6271234B1 (en) * | 1997-08-01 | 2001-08-07 | Recordati S.A., Chemical And Pharmaceutical Company | 1,4-disubstituted piperazines |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2355502A1 (fr) * | 1976-06-23 | 1978-01-20 | Roussel Uclaf | Application a titre de medicaments d'un derive de la piperazine et de ses sels |
| US4423049A (en) * | 1981-12-28 | 1983-12-27 | Mead Johnson & Company | 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyrimidines |
| GB2222768B (en) * | 1988-06-17 | 1992-01-22 | Nat Res Dev | Analgesic compounds and compositions |
| GB8909209D0 (en) * | 1989-04-22 | 1989-06-07 | Wyeth John & Brother Ltd | Piperazine derivatives |
| US4902687A (en) * | 1989-03-27 | 1990-02-20 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| ES2130116T3 (es) * | 1989-04-22 | 1999-07-01 | Wyeth John & Brother Ltd | Derivados de piperazina. |
| EP0955296A3 (en) * | 1989-04-22 | 2000-01-19 | American Home Products Corporation | Tertiary alkyl functionalized piperazine derivatives |
| EP0398413A1 (en) * | 1989-05-16 | 1990-11-22 | Duphar International Research B.V | "3,4-dehydropiperidine derivatives having psychotropic activity |
| JP3049089B2 (ja) * | 1990-01-11 | 2000-06-05 | ファルマシア・アンド・アップジョン・カンパニー | 新規な中枢作用性の６，７，８，９―テトラヒドロ―３Ｈ―ベンズ［ｅ］インドールヘテロ環式化合物 |
| GB9022820D0 (en) * | 1990-10-19 | 1990-12-05 | Wyeth John & Brother Ltd | Piperazine derivatives |
| DE4039631A1 (de) * | 1990-12-12 | 1992-06-17 | Troponwerke Gmbh & Co Kg | Neuroprotektive kombination |
| AU645681B2 (en) * | 1991-05-02 | 1994-01-20 | John Wyeth & Brother Limited | Piperazine derivatives |
| DE4135551A1 (de) * | 1991-08-31 | 1993-03-04 | Schering Ag | Verwendung von antagonisten oder partiellen agonisten am 5-ht1a-rezeptor zur behandlung und praevention von kognitiven stoerungen |
-
1992
- 1992-11-05 GB GB929223153A patent/GB9223153D0/en active Pending
-
1993
- 1993-10-21 ZA ZA937827A patent/ZA937827B/xx unknown
- 1993-10-25 JP JP51081394A patent/JP3238153B2/ja not_active Expired - Fee Related
- 1993-10-25 PT PT93923615T patent/PT877612E/pt unknown
- 1993-10-25 EP EP93923615A patent/EP0877612B1/en not_active Expired - Lifetime
- 1993-10-25 DK DK93923615T patent/DK0877612T3/da active
- 1993-10-25 US US08/428,093 patent/US5827847A/en not_active Expired - Fee Related
- 1993-10-25 ES ES93923615T patent/ES2149216T3/es not_active Expired - Lifetime
- 1993-10-25 DE DE69329252T patent/DE69329252T2/de not_active Expired - Fee Related
- 1993-10-25 WO PCT/GB1993/002197 patent/WO1994009780A1/en not_active Ceased
- 1993-10-25 AT AT93923615T patent/ATE195422T1/de not_active IP Right Cessation
- 1993-10-25 CA CA002148593A patent/CA2148593C/en not_active Expired - Fee Related
- 1993-10-25 HU HU9501290A patent/HUT72049A/hu unknown
- 1993-10-25 AU AU53421/94A patent/AU682155B2/en not_active Ceased
- 1993-10-26 TW TW082108882A patent/TW252043B/zh active
- 1993-11-04 MX MX9306879A patent/MX9306879A/es not_active IP Right Cessation
-
2000
- 2000-09-13 GR GR20000402090T patent/GR3034400T3/el not_active IP Right Cessation
-
2001
- 2001-07-04 LV LVP-01-102A patent/LV12734B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2149216T3 (es) | 2000-11-01 |
| LV12734A (en) | 2001-10-20 |
| JP3238153B2 (ja) | 2001-12-10 |
| LV12734B (en) | 2002-01-20 |
| CA2148593C (en) | 2005-12-06 |
| HUT72049A (en) | 1996-03-28 |
| AU5342194A (en) | 1994-05-24 |
| DK0877612T3 (da) | 2000-10-09 |
| DE69329252D1 (de) | 2000-09-21 |
| JPH08502743A (ja) | 1996-03-26 |
| CA2148593A1 (en) | 1994-05-11 |
| EP0877612B1 (en) | 2000-08-16 |
| TW252043B (enExample) | 1995-07-21 |
| ATE195422T1 (de) | 2000-09-15 |
| PT877612E (pt) | 2000-11-30 |
| US5827847A (en) | 1998-10-27 |
| EP0877612A1 (en) | 1998-11-18 |
| GR3034400T3 (en) | 2000-12-29 |
| WO1994009780A1 (en) | 1994-05-11 |
| ZA937827B (en) | 1995-04-21 |
| GB9223153D0 (en) | 1992-12-16 |
| AU682155B2 (en) | 1997-09-25 |
| MX9306879A (es) | 1995-01-31 |
| HU9501290D0 (en) | 1995-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |