ZA200610345B - Piperazine derivatives of alkyl oxindoles - Google Patents
Piperazine derivatives of alkyl oxindoles Download PDFInfo
- Publication number
- ZA200610345B ZA200610345B ZA200610345A ZA200610345A ZA200610345B ZA 200610345 B ZA200610345 B ZA 200610345B ZA 200610345 A ZA200610345 A ZA 200610345A ZA 200610345 A ZA200610345 A ZA 200610345A ZA 200610345 B ZA200610345 B ZA 200610345B
- Authority
- ZA
- South Africa
- Prior art keywords
- general formula
- alkyl
- acid addition
- carbon atom
- indol
- Prior art date
Links
- 150000005623 oxindoles Chemical class 0.000 title description 2
- 150000004885 piperazines Chemical class 0.000 title description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- -1 ethylene-dioxy Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 210000003169 central nervous system Anatomy 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000013200 Stress disease Diseases 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 230000007423 decrease Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000003340 mental effect Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- AUMIDOIRKJSHQJ-UHFFFAOYSA-N 3-[4-[4-(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]butyl]-5-fluoro-1,3-dihydroindol-2-one Chemical compound O1CCOC2=C1C=C(Cl)C=C2N(CC1)CCN1CCCCC1C(=O)NC2=CC=C(F)C=C21 AUMIDOIRKJSHQJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 13
- 208000008811 Agoraphobia Diseases 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 4
- 208000026139 Memory disease Diseases 0.000 claims 4
- 208000012545 Psychophysiologic disease Diseases 0.000 claims 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims 4
- 206010041250 Social phobia Diseases 0.000 claims 4
- 208000006011 Stroke Diseases 0.000 claims 4
- 208000015114 central nervous system disease Diseases 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 208000029364 generalized anxiety disease Diseases 0.000 claims 4
- 208000019906 panic disease Diseases 0.000 claims 4
- 208000019899 phobic disease Diseases 0.000 claims 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 239000012752 auxiliary agent Substances 0.000 claims 2
- AHJOSYULWRUECL-UHFFFAOYSA-N 3-[4-(4-pyridin-2-ylpiperazin-1-yl)butyl]-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1CCCCN(CC1)CCN1C1=CC=CC=N1 AHJOSYULWRUECL-UHFFFAOYSA-N 0.000 claims 1
- KATJSKRLVCHNNS-UHFFFAOYSA-N 3-[4-[4-(3-methoxyphenyl)piperazin-1-yl]butyl]-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC(N2CCN(CCCCC3C4=CC=CC=C4NC3=O)CC2)=C1 KATJSKRLVCHNNS-UHFFFAOYSA-N 0.000 claims 1
- VPHQTVYHZFPMMW-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]butyl]-1,3-dihydroindol-2-one Chemical compound COC1=CC=C(Cl)C=C1N1CCN(CCCCC2C3=CC=CC=C3NC2=O)CC1 VPHQTVYHZFPMMW-UHFFFAOYSA-N 0.000 claims 1
- SPAMBMCKMBKRGR-UHFFFAOYSA-N 5-fluoro-3-[4-(4-pyridin-2-ylpiperazin-1-yl)butyl]-1,3-dihydroindol-2-one Chemical compound C12=CC(F)=CC=C2NC(=O)C1CCCCN(CC1)CCN1C1=CC=CC=N1 SPAMBMCKMBKRGR-UHFFFAOYSA-N 0.000 claims 1
- XVVMEILIWXETCU-UHFFFAOYSA-N 5-fluoro-3-[4-[4-(3-methoxyphenyl)piperazin-1-yl]butyl]-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC(N2CCN(CCCCC3C4=CC(F)=CC=C4NC3=O)CC2)=C1 XVVMEILIWXETCU-UHFFFAOYSA-N 0.000 claims 1
- NDEQQLAZHRZSEI-UHFFFAOYSA-N 6-fluoro-3-[4-(4-pyridin-2-ylpiperazin-1-yl)butyl]-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC(F)=CC=C2C1CCCCN(CC1)CCN1C1=CC=CC=N1 NDEQQLAZHRZSEI-UHFFFAOYSA-N 0.000 claims 1
- 206010057248 Cell death Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 230000009089 cytolysis Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 230000009898 traumatic memory Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 230000000694 effects Effects 0.000 description 10
- 150000005625 indol-2-ones Chemical class 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 230000006978 adaptation Effects 0.000 description 4
- 239000002249 anxiolytic agent Substances 0.000 description 3
- 230000000949 anxiolytic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010010219 Compulsions Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 208000035755 Psychosomatic disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005530 anxiolytics Drugs 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- 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
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical group C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 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
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 210000000697 sensory organ Anatomy 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction 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
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric 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
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- 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
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0400953A HUP0400953A3 (en) | 2004-05-11 | 2004-05-11 | Piperazine derivatives of alkyl-oxindoles, pharmaceutical compositions containing them, process for producing them and their use |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200610345B true ZA200610345B (en) | 2008-05-28 |
Family
ID=89982207
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200610345A ZA200610345B (en) | 2004-05-11 | 2005-05-11 | Piperazine derivatives of alkyl oxindoles |
Country Status (27)
Country | Link |
---|---|
US (1) | US7910591B2 (de) |
EP (1) | EP1751105B1 (de) |
JP (1) | JP2007537227A (de) |
CN (1) | CN101010296B (de) |
AT (1) | ATE412633T1 (de) |
AU (1) | AU2005240843B2 (de) |
BG (1) | BG109769A (de) |
CA (1) | CA2566096A1 (de) |
CZ (1) | CZ2006779A3 (de) |
DE (1) | DE602005010693D1 (de) |
DK (1) | DK1751105T3 (de) |
EA (1) | EA010789B1 (de) |
ES (1) | ES2319795T3 (de) |
HR (1) | HRP20060420A2 (de) |
HU (1) | HUP0400953A3 (de) |
IL (1) | IL179028A (de) |
MX (1) | MXPA06013068A (de) |
NO (1) | NO20065609L (de) |
NZ (1) | NZ551545A (de) |
PL (2) | PL1751105T3 (de) |
PT (1) | PT1751105E (de) |
RS (1) | RS20060621A (de) |
SI (1) | SI1751105T1 (de) |
SK (1) | SK51102006A3 (de) |
UA (1) | UA84927C2 (de) |
WO (1) | WO2005108364A1 (de) |
ZA (1) | ZA200610345B (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUP0400953A3 (en) * | 2004-05-11 | 2008-02-28 | Egis Gyogyszergyar Nyilvanosan | Piperazine derivatives of alkyl-oxindoles, pharmaceutical compositions containing them, process for producing them and their use |
CN104163813B (zh) * | 2013-05-16 | 2017-02-01 | 广东东阳光药业有限公司 | 取代的吲哚化合物及其使用方法和用途 |
US10316025B2 (en) | 2015-06-03 | 2019-06-11 | Sunshine Lake Pharma Co., Ltd. | Substituted piperazine compounds and methods of use and use thereof |
Family Cites Families (6)
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 |
HUP0400953A3 (en) * | 2004-05-11 | 2008-02-28 | Egis Gyogyszergyar Nyilvanosan | Piperazine derivatives of alkyl-oxindoles, pharmaceutical compositions containing them, process for producing them and their use |
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2004
- 2004-05-11 HU HU0400953A patent/HUP0400953A3/hu unknown
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2005
- 2005-05-11 AT AT05745440T patent/ATE412633T1/de active
- 2005-05-11 US US11/596,465 patent/US7910591B2/en not_active Expired - Fee Related
- 2005-05-11 EA EA200602084A patent/EA010789B1/ru not_active IP Right Cessation
- 2005-05-11 PL PL05745440T patent/PL1751105T3/pl unknown
- 2005-05-11 SK SK5110-2006A patent/SK51102006A3/sk not_active Application Discontinuation
- 2005-05-11 JP JP2007512357A patent/JP2007537227A/ja not_active Ceased
- 2005-05-11 UA UAA200613076A patent/UA84927C2/ru unknown
- 2005-05-11 EP EP05745440A patent/EP1751105B1/de active Active
- 2005-05-11 CN CN2005800148934A patent/CN101010296B/zh not_active Expired - Fee Related
- 2005-05-11 CA CA002566096A patent/CA2566096A1/en not_active Abandoned
- 2005-05-11 AU AU2005240843A patent/AU2005240843B2/en not_active Expired - Fee Related
- 2005-05-11 DE DE602005010693T patent/DE602005010693D1/de active Active
- 2005-05-11 ES ES05745440T patent/ES2319795T3/es active Active
- 2005-05-11 RS RSP-2006/0621A patent/RS20060621A/sr unknown
- 2005-05-11 DK DK05745440T patent/DK1751105T3/da active
- 2005-05-11 PL PL381615A patent/PL381615A1/pl unknown
- 2005-05-11 NZ NZ551545A patent/NZ551545A/en unknown
- 2005-05-11 ZA ZA200610345A patent/ZA200610345B/en unknown
- 2005-05-11 SI SI200530564T patent/SI1751105T1/sl unknown
- 2005-05-11 PT PT05745440T patent/PT1751105E/pt unknown
- 2005-05-11 WO PCT/HU2005/000050 patent/WO2005108364A1/en active Application Filing
- 2005-05-11 CZ CZ20060779A patent/CZ2006779A3/cs unknown
- 2005-05-11 MX MXPA06013068A patent/MXPA06013068A/es active IP Right Grant
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2006
- 2006-11-02 IL IL179028A patent/IL179028A/en not_active IP Right Cessation
- 2006-12-04 HR HR20060420A patent/HRP20060420A2/xx not_active Application Discontinuation
- 2006-12-05 NO NO20065609A patent/NO20065609L/no not_active Application Discontinuation
- 2006-12-11 BG BG109769A patent/BG109769A/bg unknown
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