SK51112006A3 - Piperazínové deriváty - Google Patents
Piperazínové deriváty Download PDFInfo
- Publication number
- SK51112006A3 SK51112006A3 SK5111-2006A SK51112006A SK51112006A3 SK 51112006 A3 SK51112006 A3 SK 51112006A3 SK 51112006 A SK51112006 A SK 51112006A SK 51112006 A3 SK51112006 A3 SK 51112006A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- indol
- pharmaceutically acceptable
- dihydro
- butyl
- Prior art date
Links
- 150000004885 piperazines Chemical class 0.000 title description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 71
- 239000000460 chlorine Substances 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 27
- -1 salts salts Chemical class 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 230000003340 mental effect Effects 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 9
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- 206010020772 Hypertension Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 208000015114 central nervous system disease Diseases 0.000 claims description 6
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- 239000003814 drug Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 239000011230 binding agent Substances 0.000 claims description 3
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- MFCDOBJQHVQNDI-UHFFFAOYSA-N 3-[4-[4-(4-chlorophenyl)piperazin-1-yl]butyl]-5-methyl-1,3-dihydroindol-2-one Chemical compound C12=CC(C)=CC=C2NC(=O)C1CCCCN(CC1)CCN1C1=CC=C(Cl)C=C1 MFCDOBJQHVQNDI-UHFFFAOYSA-N 0.000 claims description 2
- HHJHHEDIWYIBPC-UHFFFAOYSA-N 3-[4-[4-[4-chloro-3-(trifluoromethyl)phenyl]piperazin-1-yl]butyl]-1,3-dihydroindol-2-one Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(N2CCN(CCCCC3C4=CC=CC=C4NC3=O)CC2)=C1 HHJHHEDIWYIBPC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- RISHXOUPXKJKGQ-UHFFFAOYSA-N 3-[4-[4-(3-chlorophenyl)piperazin-1-yl]butyl]-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC(N2CCN(CCCCC3C4=CC=CC=C4NC3=O)CC2)=C1 RISHXOUPXKJKGQ-UHFFFAOYSA-N 0.000 claims 1
- OUNVKVROPYUWPO-UHFFFAOYSA-N 3-[4-[4-(3-chlorophenyl)piperazin-1-yl]butyl]-5-methyl-1,3-dihydroindol-2-one Chemical compound C12=CC(C)=CC=C2NC(=O)C1CCCCN(CC1)CCN1C1=CC=CC(Cl)=C1 OUNVKVROPYUWPO-UHFFFAOYSA-N 0.000 claims 1
- JAOXKCOCADFHNG-UHFFFAOYSA-N 3-[4-[4-(4-chlorophenyl)piperazin-1-yl]butyl]-1,3-dihydroindol-2-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CCCCC2C3=CC=CC=C3NC2=O)CC1 JAOXKCOCADFHNG-UHFFFAOYSA-N 0.000 claims 1
- HTDJOEOPMIBGKQ-UHFFFAOYSA-N 3-[4-[4-(4-chlorophenyl)piperazin-1-yl]butyl]-6-fluoro-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC(F)=CC=C2C1CCCCN(CC1)CCN1C1=CC=C(Cl)C=C1 HTDJOEOPMIBGKQ-UHFFFAOYSA-N 0.000 claims 1
- YNDUSHJSFHOHRB-UHFFFAOYSA-N 3-[4-[4-(4-fluorophenyl)piperazin-1-yl]butyl]-1,3-dihydroindol-2-one Chemical compound C1=CC(F)=CC=C1N1CCN(CCCCC2C3=CC=CC=C3NC2=O)CC1 YNDUSHJSFHOHRB-UHFFFAOYSA-N 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 claims 1
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- 150000005625 indol-2-ones Chemical class 0.000 abstract description 9
- 210000000748 cardiovascular system Anatomy 0.000 abstract 1
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- 238000002844 melting Methods 0.000 description 16
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- IDJPRAFVIQWUTR-UHFFFAOYSA-N 4-(5-fluoro-2-oxo-1,3-dihydroindol-3-yl)butyl methanesulfonate Chemical compound C1=C(F)C=C2C(CCCCOS(=O)(=O)C)C(=O)NC2=C1 IDJPRAFVIQWUTR-UHFFFAOYSA-N 0.000 description 5
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 4
- 230000000949 anxiolytic effect Effects 0.000 description 4
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- UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 4
- 229940076279 serotonin Drugs 0.000 description 4
- MKXFXPRJCBUTLX-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)piperazine Chemical compound C1=C(Cl)C(F)=CC=C1N1CCNCC1 MKXFXPRJCBUTLX-UHFFFAOYSA-N 0.000 description 3
- AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- AJVMAKZWIVVRDR-UHFFFAOYSA-N 4-(6-fluoro-2-oxo-1,3-dihydroindol-3-yl)butyl methanesulfonate Chemical compound FC1=CC=C2C(CCCCOS(=O)(=O)C)C(=O)NC2=C1 AJVMAKZWIVVRDR-UHFFFAOYSA-N 0.000 description 3
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- 229920002472 Starch Polymers 0.000 description 1
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- 230000002490 cerebral effect Effects 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
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- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
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- 229960000913 crospovidone Drugs 0.000 description 1
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- 230000009089 cytolysis Effects 0.000 description 1
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- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 210000005153 frontal cortex Anatomy 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 150000005624 indolones Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 1
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- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
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- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
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- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019624 protein content Nutrition 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 210000000697 sensory organ Anatomy 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/28—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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0400954A HU0400954D0 (en) | 2004-05-11 | 2004-05-11 | Piperazine derivatives of alkyl oxindoles |
| HU0500461A HUP0500461A3 (en) | 2005-05-05 | 2005-05-05 | Pyperazine derivatives of alkyl-oxindoles |
| PCT/HU2005/000048 WO2005108363A1 (en) | 2004-05-11 | 2005-05-10 | Piperazine derivatives of alkyl oxindoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK51112006A3 true SK51112006A3 (sk) | 2007-05-03 |
Family
ID=89985994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK5111-2006A SK51112006A3 (sk) | 2004-05-11 | 2005-05-10 | Piperazínové deriváty |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20070219209A1 (es) |
| EP (1) | EP1751106B1 (es) |
| JP (1) | JP2007537226A (es) |
| KR (1) | KR20070011551A (es) |
| AT (1) | ATE412634T1 (es) |
| AU (1) | AU2005240842B2 (es) |
| BG (1) | BG109768A (es) |
| CA (1) | CA2564009A1 (es) |
| CZ (1) | CZ2006778A3 (es) |
| DE (1) | DE602005010694D1 (es) |
| DK (1) | DK1751106T3 (es) |
| EA (1) | EA011280B1 (es) |
| ES (1) | ES2317241T3 (es) |
| HR (2) | HRP20060401A2 (es) |
| IL (1) | IL178759A0 (es) |
| MX (1) | MXPA06013064A (es) |
| NO (1) | NO20065697L (es) |
| NZ (1) | NZ551542A (es) |
| PL (1) | PL1751106T3 (es) |
| PT (1) | PT1751106E (es) |
| RS (1) | RS20060620A (es) |
| SI (1) | SI1751106T1 (es) |
| SK (1) | SK51112006A3 (es) |
| WO (1) | WO2005108363A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE435204T1 (de) * | 2004-05-11 | 2009-07-15 | Egis Gyogyszergyar Nyrt | 3-(((4-phenyl)-piperazin-1-yl)-alkyl)-3-alkyl-1 3-dihydro-2h-indol-2-on-derivate und verwandte verbindungen zur behandlung von erkrankungen des zentralnervensystems |
| CN106243088B (zh) | 2015-06-03 | 2019-01-04 | 广东东阳光药业有限公司 | 取代的哌嗪化合物及其使用方法和用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452808A (en) * | 1982-12-07 | 1984-06-05 | Smithkline Beckman Corporation | 4-Aminoalkyl-2(3H)-indolones |
| MX173362B (es) * | 1987-03-02 | 1994-02-23 | Pfizer | Compuestos de piperazinil heterociclicos y procedimiento para su preparacion |
| FR2635104B1 (fr) * | 1988-08-03 | 1992-04-30 | Synthelabo | Derives d'indolone, leur preparation et leur application en therapeutique |
| GB8830312D0 (en) * | 1988-12-28 | 1989-02-22 | Lundbeck & Co As H | Heterocyclic compounds |
| WO1998008816A1 (fr) * | 1996-08-26 | 1998-03-05 | Meiji Seika Kaisha, Ltd. | Derives d'indoxyle et psychotropes |
-
2005
- 2005-05-10 RS RSP-2006/0620A patent/RS20060620A/sr unknown
- 2005-05-10 DE DE602005010694T patent/DE602005010694D1/de active Active
- 2005-05-10 AU AU2005240842A patent/AU2005240842B2/en not_active Ceased
- 2005-05-10 ES ES05745442T patent/ES2317241T3/es active Active
- 2005-05-10 JP JP2007512356A patent/JP2007537226A/ja active Pending
- 2005-05-10 AT AT05745442T patent/ATE412634T1/de active
- 2005-05-10 PT PT05745442T patent/PT1751106E/pt unknown
- 2005-05-10 WO PCT/HU2005/000048 patent/WO2005108363A1/en active Application Filing
- 2005-05-10 DK DK05745442T patent/DK1751106T3/da active
- 2005-05-10 PL PL05745442T patent/PL1751106T3/pl unknown
- 2005-05-10 SK SK5111-2006A patent/SK51112006A3/sk not_active Application Discontinuation
- 2005-05-10 NZ NZ551542A patent/NZ551542A/en unknown
- 2005-05-10 MX MXPA06013064A patent/MXPA06013064A/es active IP Right Grant
- 2005-05-10 EP EP05745442A patent/EP1751106B1/en active Active
- 2005-05-10 EA EA200602080A patent/EA011280B1/ru not_active IP Right Cessation
- 2005-05-10 CA CA002564009A patent/CA2564009A1/en not_active Abandoned
- 2005-05-10 US US11/596,466 patent/US20070219209A1/en not_active Abandoned
- 2005-05-10 CZ CZ20060778A patent/CZ2006778A3/cs unknown
- 2005-05-10 KR KR1020067025135A patent/KR20070011551A/ko not_active Application Discontinuation
- 2005-05-10 SI SI200530563T patent/SI1751106T1/sl unknown
-
2006
- 2006-10-19 IL IL178759A patent/IL178759A0/en unknown
- 2006-11-20 HR HR20060401A patent/HRP20060401A2/xx not_active Application Discontinuation
- 2006-12-11 BG BG109768A patent/BG109768A/bg unknown
- 2006-12-11 NO NO20065697A patent/NO20065697L/no not_active Application Discontinuation
-
2009
- 2009-01-29 HR HR20090054T patent/HRP20090054T3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL1751106T3 (pl) | 2009-07-31 |
| EP1751106A1 (en) | 2007-02-14 |
| NO20065697L (no) | 2007-02-02 |
| PT1751106E (pt) | 2009-02-10 |
| DE602005010694D1 (de) | 2008-12-11 |
| ATE412634T1 (de) | 2008-11-15 |
| ES2317241T3 (es) | 2009-04-16 |
| RS20060620A (en) | 2008-09-29 |
| EP1751106B1 (en) | 2008-10-29 |
| KR20070011551A (ko) | 2007-01-24 |
| NZ551542A (en) | 2010-06-25 |
| CZ2006778A3 (cs) | 2007-03-07 |
| HRP20090054T3 (en) | 2009-03-31 |
| EA011280B1 (ru) | 2009-02-27 |
| BG109768A (bg) | 2008-03-31 |
| CA2564009A1 (en) | 2005-11-17 |
| MXPA06013064A (es) | 2007-04-27 |
| DK1751106T3 (da) | 2009-03-09 |
| IL178759A0 (en) | 2007-02-11 |
| HRP20060401A2 (en) | 2007-03-31 |
| US20070219209A1 (en) | 2007-09-20 |
| WO2005108363A1 (en) | 2005-11-17 |
| AU2005240842B2 (en) | 2011-10-06 |
| SI1751106T1 (sl) | 2009-06-30 |
| AU2005240842A1 (en) | 2005-11-17 |
| JP2007537226A (ja) | 2007-12-20 |
| EA200602080A1 (ru) | 2007-04-27 |
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