NO311683B1 - Anvendelse av piperazinderivater - Google Patents
Anvendelse av piperazinderivater Download PDFInfo
- Publication number
- NO311683B1 NO311683B1 NO19970163A NO970163A NO311683B1 NO 311683 B1 NO311683 B1 NO 311683B1 NO 19970163 A NO19970163 A NO 19970163A NO 970163 A NO970163 A NO 970163A NO 311683 B1 NO311683 B1 NO 311683B1
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- het
- pct
- dopamine
- receptor
- Prior art date
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- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract description 8
- 102000004073 Dopamine D3 Receptors Human genes 0.000 abstract description 4
- 108090000525 Dopamine D3 Receptors Proteins 0.000 abstract description 4
- 229960003638 dopamine Drugs 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 101150049660 DRD2 gene Proteins 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
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- 239000012071 phase Substances 0.000 description 3
- 239000007940 sugar coated tablet Substances 0.000 description 3
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 description 2
- JVWMYMOCTWRQCO-UHFFFAOYSA-N 1-(3-chloropropyl)-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCCCl)CC2)=C1 JVWMYMOCTWRQCO-UHFFFAOYSA-N 0.000 description 2
- QBYFAVFZYXDVOB-UHFFFAOYSA-N 1-(5-pyridin-2-ylsulfanylpentyl)-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCCCCSC=3N=CC=CC=3)CC2)=C1 QBYFAVFZYXDVOB-UHFFFAOYSA-N 0.000 description 2
- ISOVIZHXUQXMLY-UHFFFAOYSA-N 2-(5-chloropentylsulfanyl)pyridine Chemical compound ClCCCCCSC1=CC=CC=N1 ISOVIZHXUQXMLY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108050004812 Dopamine receptor Proteins 0.000 description 2
- 102000015554 Dopamine receptor Human genes 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 210000003715 limbic system Anatomy 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
- 239000000018 receptor agonist Substances 0.000 description 2
- 229940044601 receptor agonist Drugs 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000009495 sugar coating Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JOALHNFSPWQSBE-UHFFFAOYSA-N 1-(3-pyridin-2-ylsulfanylpropyl)-4-[2-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC=C1N1CCN(CCCSC=2N=CC=CC=2)CC1 JOALHNFSPWQSBE-UHFFFAOYSA-N 0.000 description 1
- VGRGMHCAPFRIGT-UHFFFAOYSA-N 1-(3-pyridin-2-ylsulfanylpropyl)-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCCSC=3N=CC=CC=3)CC2)=C1 VGRGMHCAPFRIGT-UHFFFAOYSA-N 0.000 description 1
- PHHNNDKXQVKJEP-UHFFFAOYSA-N 1-bromo-5-chloropentane Chemical compound ClCCCCCBr PHHNNDKXQVKJEP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YDJUKXZGPAOCSN-UHFFFAOYSA-N 2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethanamine Chemical compound C1CN(CCN)CCN1C1=CC=CC(C(F)(F)F)=C1 YDJUKXZGPAOCSN-UHFFFAOYSA-N 0.000 description 1
- QHOINBKBMJLHPY-UHFFFAOYSA-N 2-chloroethyl formate Chemical compound ClCCOC=O QHOINBKBMJLHPY-UHFFFAOYSA-N 0.000 description 1
- -1 2-pyridineacetic acid N-hydroxysuccinimide Chemical compound 0.000 description 1
- DBWAVASEYCLVEP-UHFFFAOYSA-N 3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-1-amine Chemical compound C1CN(CCCN)CCN1C1=CC=CC(C(F)(F)F)=C1 DBWAVASEYCLVEP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
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- 238000009505 enteric coating Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- FYUWIEKAVLOHSE-UHFFFAOYSA-N ethenyl acetate;1-ethenylpyrrolidin-2-one Chemical compound CC(=O)OC=C.C=CN1CCCC1=O FYUWIEKAVLOHSE-UHFFFAOYSA-N 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 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
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- 238000012417 linear regression Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- HBJPOHDQQVIBLT-UHFFFAOYSA-N n-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCNC(=O)C=3N=CC=CC=3)CC2)=C1 HBJPOHDQQVIBLT-UHFFFAOYSA-N 0.000 description 1
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- 150000003217 pyrazoles Chemical class 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
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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
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4425146A DE4425146A1 (de) | 1994-07-15 | 1994-07-15 | Verwendung heterocyclischer Verbindungen |
| PCT/EP1995/002782 WO1996002246A1 (fr) | 1994-07-15 | 1995-07-14 | Utilisation de composes heterocycliques comme ligands de la dopamine-d¿3? |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO970163D0 NO970163D0 (no) | 1997-01-14 |
| NO970163L NO970163L (no) | 1997-03-14 |
| NO311683B1 true NO311683B1 (no) | 2002-01-07 |
Family
ID=6523325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19970163A NO311683B1 (no) | 1994-07-15 | 1997-01-14 | Anvendelse av piperazinderivater |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6090807A (fr) |
| EP (1) | EP0771197B1 (fr) |
| JP (1) | JPH10502658A (fr) |
| KR (2) | KR100443850B1 (fr) |
| CN (2) | CN1534023A (fr) |
| AT (1) | ATE236629T1 (fr) |
| AU (1) | AU704839B2 (fr) |
| BG (1) | BG63487B1 (fr) |
| BR (1) | BR9508296A (fr) |
| CA (1) | CA2195242A1 (fr) |
| CZ (1) | CZ293126B6 (fr) |
| DE (2) | DE4425146A1 (fr) |
| DK (1) | DK0771197T3 (fr) |
| ES (1) | ES2196072T3 (fr) |
| FI (1) | FI970148A0 (fr) |
| HU (1) | HUT77608A (fr) |
| MX (1) | MX9700430A (fr) |
| NO (1) | NO311683B1 (fr) |
| NZ (1) | NZ290388A (fr) |
| PT (1) | PT771197E (fr) |
| SI (1) | SI9520084B (fr) |
| WO (1) | WO1996002246A1 (fr) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997003067A1 (fr) * | 1995-07-13 | 1997-01-30 | Knoll Aktiengesellschaft | Derives de piperazine utilises comme agents therapeutiques |
| DE19600934A1 (de) | 1996-01-12 | 1997-07-17 | Basf Ag | Substituierte Aza- und Diazacycloheptan- und Cyclooctanverbindungen und deren Verwendung |
| WO1997043262A1 (fr) * | 1996-05-11 | 1997-11-20 | Smithkline Beecham P.L.C. | Derives de tetrahydroisoquinoleine utilisees en tant que modulateurs des recepteurs de la dopamine d3 |
| DE69704060T2 (de) * | 1996-08-14 | 2001-08-02 | Smithkline Beecham Plc | Tetrahydroisochinolinderivate und ihre pharmazeutische anwendung |
| GB9708694D0 (en) * | 1997-04-30 | 1997-06-18 | Smithkline Beecham Plc | Compounds |
| GB9708805D0 (en) * | 1997-05-01 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
| GB9709303D0 (en) * | 1997-05-09 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
| DE19728996A1 (de) * | 1997-07-07 | 1999-01-14 | Basf Ag | Triazolverbindungen und deren Verwendung |
| TW530054B (en) | 1997-09-24 | 2003-05-01 | Duphar Int Res | New piperazine and piperidine compounds |
| US6632823B1 (en) | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| US6218396B1 (en) * | 1998-02-20 | 2001-04-17 | Orth-Mcneil Pharmaceutical, Inc. | Substituted pyridino arylpiperazines useful in the treatment of benign prostatic hyperplasia |
| GB9810876D0 (en) | 1998-05-20 | 1998-07-22 | Smithkline Beecham Plc | Compounds |
| AR023681A1 (es) | 1998-10-08 | 2002-09-04 | Smithkline Beecham Plc | Derivados de tetrahidrobenzazepinas, composiciones farmaceuticas y el uso de los mismos para la manufactura de un medicamento. |
| EP1970052A2 (fr) | 1999-02-09 | 2008-09-17 | Pfizer Products Inc. | Compositions de médicaments basiques avec une meilleure biodisponibilité |
| GB9923748D0 (en) | 1999-10-07 | 1999-12-08 | Glaxo Group Ltd | Chemical compounds |
| USRE39921E1 (en) | 1999-10-07 | 2007-11-13 | Smithkline Beecham Corporation | Chemical compounds |
| IT1314191B1 (it) * | 1999-10-18 | 2002-12-06 | Recordati Chem Pharm | Derivati isossazolcarbossamidici |
| US6365591B1 (en) | 1999-10-18 | 2002-04-02 | Recordati, S.A., Chemical And Pharmacueticals Company | Isoxazolecarboxamide derivatives |
| EP1272187B1 (fr) * | 2000-03-27 | 2008-07-30 | Abbott GmbH & Co. KG | Ligands du recepteur d3 de la dopamine destines au traitement de la dependance |
| GB0025354D0 (en) * | 2000-10-17 | 2000-11-29 | Glaxo Group Ltd | Chemical compounds |
| GB0117577D0 (en) * | 2001-02-16 | 2001-09-12 | Aventis Pharm Prod Inc | Novel heterocyclic substituted carbonyl derivatives and their use as dopamine D receptor ligands |
| GB0108594D0 (en) * | 2001-04-05 | 2001-05-23 | Glaxo Group Ltd | Chemical compounds |
| HUP0103987A3 (en) * | 2001-09-28 | 2004-11-29 | Richter Gedeon Vegyeszet | Phenylpiperazinylalkyl carboxylic acid amid derivatives, process for their preparation, pharmaceutical compositions containing them and their intermediates |
| GB0203022D0 (en) * | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| EP1472222A1 (fr) * | 2002-02-08 | 2004-11-03 | Glaxo Group Limited | Derives piperidylcarboxamide, et leur utilisation dans le traitement des maladies dont la mediation est assuree par les tachykinines |
| GB0203020D0 (en) * | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| CN1665503A (zh) * | 2002-07-04 | 2005-09-07 | 施瓦茨制药有限公司 | 杂芳烃甲酰胺作为多巴胺－d3配体用于治疗中枢神经系统疾病的用途 |
| DE10232020A1 (de) * | 2002-07-04 | 2004-02-26 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Neurorezeptoraktive Heteroarencarboxamide |
| TW200507841A (en) * | 2003-03-27 | 2005-03-01 | Glaxo Group Ltd | Antibacterial agents |
| DE10315569A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| US20040204422A1 (en) | 2003-04-14 | 2004-10-14 | Abbott Gmbh & Co. Kg. | N-[(Piperazinyl)hetaryl]arylsulfonamide compounds |
| US7320979B2 (en) * | 2003-04-14 | 2008-01-22 | Abbott Gmbh & Co. Kg. | N-[(piperazinyl)hetaryl]arylsulfonamide compounds |
| DE10358004A1 (de) | 2003-12-11 | 2005-07-14 | Abbott Gmbh & Co. Kg | Ketolactam-Verbindungen und ihre Verwendung |
| ATE529114T1 (de) | 2003-12-18 | 2011-11-15 | Abbott Gmbh & Co Kg | Tetrahydrobenzazepine und ihre verwendung in der modulation des dopamin-d3-rezeptors |
| US20050137186A1 (en) | 2003-12-18 | 2005-06-23 | Abbott Gmbh & Co. Kg. | Tetrahydrobenzazepines and their use |
| DE102004027358A1 (de) | 2004-06-04 | 2005-12-29 | Abbott Gmbh & Co. Kg | Pyrimidinverbindungen und ihre Verwendung |
| DE102004027359A1 (de) * | 2004-06-04 | 2005-12-29 | Abbott Gmbh & Co. Kg | Pyridin-2-onverbindungen und deren Verwendung |
| DE602005018366D1 (de) | 2004-08-09 | 2010-01-28 | Abbott Gmbh & Co Kg | Zur behandlung von auf eine modulation des dopamin-d3-rezeptors ansprechende erkrankungen geeignete 4-piperazinylpyrimidinverbindungen |
| JP2008526715A (ja) * | 2005-01-03 | 2008-07-24 | ユニベルシタ デグリ ストゥディ ディ シエナ | 神経精神障害の治療のためのアリールピペラジン誘導体 |
| US7511035B2 (en) * | 2005-01-25 | 2009-03-31 | Glaxo Group Limited | Antibacterial agents |
| PA8802101A1 (es) | 2007-11-02 | 2009-08-26 | Abbott Gmbh & Co Kg | Compuestos de 1,2,4-3,5-diona adecuados para el tratamiento de trastornos que responden a la modulación del receptor de dopamina d3 |
| WO2009095438A1 (fr) * | 2008-02-01 | 2009-08-06 | Neurosearch A/S | Nouveaux dérivés d'arylpipérazine utiles comme modulateurs des récepteurs de la dopamine et de la sérotonine |
| US9227944B2 (en) | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
| WO2010040274A1 (fr) | 2008-10-10 | 2010-04-15 | 中国人民解放军军事医学科学院毒物药物研究所 | Nouveaux ligands de récepteurs d3 de la dopamine, leurs procédés de préparation et leurs applications |
| US8884034B2 (en) | 2009-07-08 | 2014-11-11 | Dermira (Canada), Inc. | TOFA analogs useful in treating dermatological disorders or conditions |
| US8609672B2 (en) | 2010-08-27 | 2013-12-17 | University Of The Pacific | Piperazinylpyrimidine analogues as protein kinase inhibitors |
| WO2012051601A2 (fr) * | 2010-10-14 | 2012-04-19 | Epiomed Therapeutics, Inc. | Composés hétéroarylthio |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| CN102408397B (zh) | 2011-10-19 | 2014-08-20 | 上海贝美医药科技有限公司 | 紫杉烷类衍生物及其制备方法 |
| WO2023144764A1 (fr) | 2022-01-29 | 2023-08-03 | Suven Life Sciences Limited | Composes de benzoisothiazole et de benzoisoxazole pour le traitement de troubles mentaux |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
| DE1620016C3 (de) * | 1966-07-02 | 1979-08-30 | Merck Patent Gmbh, 6100 Darmstadt | 3-{Piperazinoalkyl)-pyrazole und Verfahren zu ihrer Herstellung |
| DE2060816C3 (de) * | 1970-12-10 | 1980-09-04 | Merck Patent Gmbh, 6100 Darmstadt | 4-Phenylpiperidinderivate Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen enthaltend diese Verbindungen |
| DE2110568A1 (de) * | 1971-03-05 | 1972-09-07 | Merck Patent Gmbh | Neue N-Acyl-(piperazinoalkyl)-pyrazole |
| DE2213808A1 (de) * | 1972-03-22 | 1973-09-27 | Merck Patent Gmbh | Verfahren zur herstellung von 3-(piperazinoalkyl)-pyrazolen |
| DE2258033A1 (de) * | 1972-11-27 | 1974-05-30 | Merck Patent Gmbh | Verfahren zur herstellung von pyrazolderivaten |
| DE2513940A1 (de) * | 1975-03-29 | 1976-10-14 | Merck Patent Gmbh | Pharmazeutische zubereitung |
| US4123529A (en) * | 1976-04-23 | 1978-10-31 | Lilly Industries Limited | Phenylpiperazine derivatives |
| US4404382A (en) * | 1980-09-17 | 1983-09-13 | The Upjohn Company | Piperazinyl-substituted imidazoles |
| US5254552A (en) * | 1988-05-24 | 1993-10-19 | American Home Products Corporation | Aryl-and heteroaryl piperazinyl carboxamides having central nervous system activity |
| MX9201991A (es) * | 1991-05-02 | 1992-11-01 | Jonh Wyeth & Brother Limited | Derivados de piperazina y procedimiento para su preparacion. |
| FR2682953B1 (fr) * | 1991-10-23 | 1995-04-21 | Inst Nat Sante Rech Med | Nouveaux derives de naphtamides, leur procede de preparation et leur application dans le domaine therapeutique. |
| SG65570A1 (en) * | 1992-02-25 | 1999-06-22 | Recordati Chem Pharm | Heterobicyclic compounds |
| IT1254469B (it) * | 1992-02-25 | 1995-09-25 | Recordati Chem Pharm | Derivati benzopiranici e benzotiopiranici |
| US5395835A (en) * | 1994-03-24 | 1995-03-07 | Warner-Lambert Company | Naphthalamides as central nervous system agents |
-
1994
- 1994-07-15 DE DE4425146A patent/DE4425146A1/de not_active Ceased
-
1995
- 1995-07-14 MX MX9700430A patent/MX9700430A/es not_active IP Right Cessation
- 1995-07-14 EP EP95926896A patent/EP0771197B1/fr not_active Expired - Lifetime
- 1995-07-14 DK DK95926896T patent/DK0771197T3/da active
- 1995-07-14 KR KR10-2003-7012315A patent/KR100443850B1/ko not_active IP Right Cessation
- 1995-07-14 CN CNA2003101131172A patent/CN1534023A/zh active Pending
- 1995-07-14 DE DE59510635T patent/DE59510635D1/de not_active Expired - Lifetime
- 1995-07-14 PT PT95926896T patent/PT771197E/pt unknown
- 1995-07-14 HU HU9700111A patent/HUT77608A/hu unknown
- 1995-07-14 BR BR9508296A patent/BR9508296A/pt active Search and Examination
- 1995-07-14 CZ CZ199796A patent/CZ293126B6/cs not_active IP Right Cessation
- 1995-07-14 JP JP8504701A patent/JPH10502658A/ja not_active Ceased
- 1995-07-14 SI SI9520084A patent/SI9520084B/sl not_active IP Right Cessation
- 1995-07-14 CN CN95194149A patent/CN1152870A/zh active Pending
- 1995-07-14 NZ NZ290388A patent/NZ290388A/en unknown
- 1995-07-14 KR KR1019970700265A patent/KR970704435A/ko active Search and Examination
- 1995-07-14 AT AT95926896T patent/ATE236629T1/de not_active IP Right Cessation
- 1995-07-14 WO PCT/EP1995/002782 patent/WO1996002246A1/fr active IP Right Grant
- 1995-07-14 US US08/765,181 patent/US6090807A/en not_active Expired - Lifetime
- 1995-07-14 AU AU31114/95A patent/AU704839B2/en not_active Ceased
- 1995-07-14 ES ES95926896T patent/ES2196072T3/es not_active Expired - Lifetime
- 1995-07-14 CA CA002195242A patent/CA2195242A1/fr not_active Abandoned
-
1997
- 1997-01-06 BG BG101112A patent/BG63487B1/bg unknown
- 1997-01-14 NO NO19970163A patent/NO311683B1/no not_active IP Right Cessation
- 1997-01-14 FI FI970148A patent/FI970148A0/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100443850B1 (ko) | 2004-08-11 |
| AU704839B2 (en) | 1999-05-06 |
| BG63487B1 (bg) | 2002-03-29 |
| NO970163L (no) | 1997-03-14 |
| NO970163D0 (no) | 1997-01-14 |
| WO1996002246A1 (fr) | 1996-02-01 |
| CZ9697A3 (en) | 1997-08-13 |
| CN1534023A (zh) | 2004-10-06 |
| SI9520084B (sl) | 2005-02-28 |
| MX9700430A (es) | 1998-05-31 |
| FI970148A (fi) | 1997-01-14 |
| FI970148A0 (fi) | 1997-01-14 |
| DK0771197T3 (da) | 2003-06-23 |
| CN1152870A (zh) | 1997-06-25 |
| EP0771197B1 (fr) | 2003-04-09 |
| DE4425146A1 (de) | 1996-01-18 |
| ES2196072T3 (es) | 2003-12-16 |
| CA2195242A1 (fr) | 1996-02-01 |
| NZ290388A (en) | 2001-04-27 |
| JPH10502658A (ja) | 1998-03-10 |
| ATE236629T1 (de) | 2003-04-15 |
| BG101112A (en) | 1998-04-30 |
| KR970704435A (ko) | 1997-09-06 |
| HUT77608A (hu) | 1998-06-29 |
| SI9520084A (en) | 1997-08-31 |
| PT771197E (pt) | 2003-08-29 |
| US6090807A (en) | 2000-07-18 |
| BR9508296A (pt) | 1998-05-19 |
| AU3111495A (en) | 1996-02-16 |
| EP0771197A1 (fr) | 1997-05-07 |
| DE59510635D1 (de) | 2003-05-15 |
| HU9700111D0 (en) | 1997-02-28 |
| KR20040000412A (ko) | 2004-01-03 |
| CZ293126B6 (cs) | 2004-02-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |