NO323401B1 - Halogensubstituerte 4-fenyl-piperazinderivater, farmasoytiske sammensetninger inneholdende dem og deres anvendelse. - Google Patents

Halogensubstituerte 4-fenyl-piperazinderivater, farmasoytiske sammensetninger inneholdende dem og deres anvendelse. Download PDF

Info

Publication number: NO323401B1
Authority: NO; Norway
Prior art keywords: halogen; compound according; dihydro; indol; piperazin
Prior art date: 1999-12-30

Application number

NO20023151A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023151L (no

NO20023151D0 (no

Inventor

Jan Kehler

Benny Bang-Andersen

Jakob Felding

Original Assignee

Lundbeck & Co As H

Priority date (The priority date 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 date listed.)

1999-12-30

Filing date

2002-06-28

Publication date

2007-04-23

2002-06-28 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2002-06-28 Publication of NO20023151D0 publication Critical patent/NO20023151D0/no

2002-08-02 Publication of NO20023151L publication Critical patent/NO20023151L/no

2007-04-23 Publication of NO323401B1 publication Critical patent/NO323401B1/no

Links

239000008194 pharmaceutical composition Chemical class 0.000 title claims description 5
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 72
229910052736 halogen Chemical group 0.000 claims abstract description 24
150000002367 halogens Chemical group 0.000 claims abstract description 24
-1 4-phenyl-1-piperazinyl Chemical class 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
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 claims abstract description 3
229910052799 carbon Inorganic materials 0.000 claims abstract description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
201000000980 schizophrenia Diseases 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
229940079593 drug Drugs 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
208000024891 symptom Diseases 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
208000028017 Psychotic disease Diseases 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
208000012661 Dyskinesia Diseases 0.000 claims description 4
208000011688 Generalised anxiety disease Diseases 0.000 claims description 4
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 4
208000019022 Mood disease Diseases 0.000 claims description 4
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
230000016571 aggressive behavior Effects 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
208000029364 generalized anxiety disease Diseases 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
208000019906 panic disease Diseases 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
208000010877 cognitive disease Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 abstract 2
229910052717 sulfur Inorganic materials 0.000 abstract 2
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
238000000034 method Methods 0.000 description 21
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 19
239000000203 mixture Substances 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 16
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 15
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
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125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
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125000000217 alkyl group Chemical group 0.000 description 8
230000000561 anti-psychotic effect Effects 0.000 description 8
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101150049660 DRD2 gene Proteins 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
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230000009467 reduction Effects 0.000 description 7
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
210000004556 brain Anatomy 0.000 description 6
PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
UDQMXYJSNNCRAS-UHFFFAOYSA-N 2,3-dichlorophenylpiperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1Cl UDQMXYJSNNCRAS-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
102000004980 Dopamine D2 Receptors Human genes 0.000 description 4
108090001111 Dopamine D2 Receptors Proteins 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
206010031127 Orthostatic hypotension Diseases 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 4
108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 4
230000008901 benefit Effects 0.000 description 4
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150000002148 esters Chemical class 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
YXBGWRXAUDFJES-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)piperazin-1-yl]-1-(2,3-dihydroindol-1-yl)butan-1-one Chemical compound ClC1=CC=CC(N2CCN(CCCC(=O)N3C4=CC=CC=C4CC3)CC2)=C1 YXBGWRXAUDFJES-UHFFFAOYSA-N 0.000 description 3
102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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125000003118 aryl group Chemical group 0.000 description 3
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239000000018 receptor agonist Substances 0.000 description 3
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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 3
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AZNZRRREZBGIEP-UHFFFAOYSA-N 3-[4-(2,3-dichlorophenyl)piperazin-1-yl]-1-(5-fluoro-2,3-dihydroindol-1-yl)propan-1-one Chemical compound C1CC2=CC(F)=CC=C2N1C(=O)CCN(CC1)CCN1C1=CC=CC(Cl)=C1Cl AZNZRRREZBGIEP-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
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- 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
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Epidemiology (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

NO20023151A 1999-12-30 2002-06-28 Halogensubstituerte 4-fenyl-piperazinderivater, farmasoytiske sammensetninger inneholdende dem og deres anvendelse. NO323401B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA199901887		1999-12-30
PCT/DK2000/000728 WO2001049679A1 (en)	1999-12-30	2000-12-22	4-phenyl-1-piperazinyl, -piperidinyl and -tetrahydropyridyl derivatives

Publications (3)

Publication Number	Publication Date
NO20023151D0 NO20023151D0 (no)	2002-06-28
NO20023151L NO20023151L (no)	2002-08-02
NO323401B1 true NO323401B1 (no)	2007-04-23

Family

ID=8108820

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO20023151A NO323401B1 (no)	1999-12-30	2002-06-28	Halogensubstituerte 4-fenyl-piperazinderivater, farmasoytiske sammensetninger inneholdende dem og deres anvendelse.
NO20065681A NO20065681L (no)	1999-12-30	2006-12-14	4-fenyl-1-piperazinyl, -piperidinyl og -tetrahydropyridylderivater

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO20065681A NO20065681L (no)	1999-12-30	2006-12-14	4-fenyl-1-piperazinyl, -piperidinyl og -tetrahydropyridylderivater

Country Status (32)

Country	Link
US (2)	US7074796B2 (zh)
EP (2)	EP1246817B1 (zh)
JP (1)	JP2003519225A (zh)
KR (2)	KR100792186B1 (zh)
CN (2)	CN1244577C (zh)
AR (1)	AR029461A1 (zh)
AT (2)	ATE269857T1 (zh)
AU (2)	AU783786B2 (zh)
BG (1)	BG106960A (zh)
BR (1)	BR0016953A (zh)
CA (1)	CA2395869C (zh)
CZ (1)	CZ20022603A3 (zh)
DE (2)	DE60011817T2 (zh)
DK (2)	DK1246817T3 (zh)
EA (2)	EA008627B1 (zh)
ES (2)	ES2302992T3 (zh)
HK (1)	HK1055960A1 (zh)
HR (1)	HRP20020567A2 (zh)
HU (1)	HUP0203839A3 (zh)
IL (3)	IL150366A0 (zh)
IS (1)	IS6432A (zh)
MX (1)	MXPA02006590A (zh)
NO (2)	NO323401B1 (zh)
NZ (2)	NZ519740A (zh)
PL (1)	PL355502A1 (zh)
PT (2)	PT1246817E (zh)
SG (1)	SG152900A1 (zh)
SK (1)	SK11072002A3 (zh)
TR (2)	TR200402408T4 (zh)
UA (1)	UA73756C2 (zh)
WO (1)	WO2001049679A1 (zh)
ZA (1)	ZA200205019B (zh)

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FR2831166B1 (fr) *	2001-10-18	2004-02-27	Sanofi Synthelabo	Aralkyl-tetrahydro-pyridines, leur preparation et compositions pharmaceutiques les contenant
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MXPA04006281A (es)	2001-12-28	2004-09-27	Acadia Pharm Inc	Analogos de tetrahidroquinolina como agonistas muscarinicos.
MXPA06007172A (es)	2003-12-23	2006-08-23	Lundbeck & Co As H	Derivados de 2-(1h-indolilsulfanil)-bencilamina como ssri.
DE102004027358A1 (de)	2004-06-04	2005-12-29	Abbott Gmbh & Co. Kg	Pyrimidinverbindungen und ihre Verwendung
AR052308A1 (es)	2004-07-16	2007-03-14	Lundbeck & Co As H	Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto
FR2878524B1 (fr) *	2004-12-01	2007-01-19	Bioprojet Soc Civ Ile	Nouveaux derives d'arylpiperazine
AR054393A1 (es)	2005-06-17	2007-06-20	Lundbeck & Co As H	Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos.
US7629473B2 (en)	2005-06-17	2009-12-08	H. Lundbeck A/S	2-(1H-indolylsulfanyl)-aryl amine derivatives
EP1870405A1 (en) *	2006-06-22	2007-12-26	Bioprojet	Carbonylated (Aza)cyclohexanes as dopamine D3 receptor ligands
US9598401B2 (en)	2013-07-29	2017-03-21	Sunshine Lake Pharma Co., Ltd.	Substituted heteroaryl compounds and methods of use thereof
EP3083589B1 (en)	2013-12-20	2019-12-18	Sunshine Lake Pharma Co., Ltd.	Substituted piperazine compounds and methods of use thereof
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

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FR2635104B1 (fr) *	1988-08-03	1992-04-30	Synthelabo	Derives d'indolone, leur preparation et leur application en therapeutique
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SG47711A1 (en) *	1993-06-28	1998-04-17	American Home Prod	New treatments using phenehylamine derivatives
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2000
- 2000-12-22 EA EA200400641A patent/EA008627B1/ru not_active IP Right Cessation
- 2000-12-22 SK SK1107-2002A patent/SK11072002A3/sk unknown
- 2000-12-22 KR KR1020077000879A patent/KR100792186B1/ko not_active IP Right Cessation
- 2000-12-22 IL IL15036600A patent/IL150366A0/xx active IP Right Grant
- 2000-12-22 ES ES04007739T patent/ES2302992T3/es not_active Expired - Lifetime
- 2000-12-22 EP EP00984931A patent/EP1246817B1/en not_active Expired - Lifetime
- 2000-12-22 HU HU0203839A patent/HUP0203839A3/hu unknown
- 2000-12-22 AT AT00984931T patent/ATE269857T1/de not_active IP Right Cessation
- 2000-12-22 PT PT00984931T patent/PT1246817E/pt unknown
- 2000-12-22 SG SG200405552-1A patent/SG152900A1/en unknown
- 2000-12-22 PL PL00355502A patent/PL355502A1/xx not_active IP Right Cessation
- 2000-12-22 WO PCT/DK2000/000728 patent/WO2001049679A1/en active Application Filing
- 2000-12-22 DK DK00984931T patent/DK1246817T3/da active
- 2000-12-22 EA EA200200729A patent/EA005013B1/ru not_active IP Right Cessation
- 2000-12-22 CN CNB00819145XA patent/CN1244577C/zh not_active Expired - Fee Related
- 2000-12-22 NZ NZ519740A patent/NZ519740A/en unknown
- 2000-12-22 ES ES00984931T patent/ES2223628T3/es not_active Expired - Lifetime
- 2000-12-22 MX MXPA02006590A patent/MXPA02006590A/es active IP Right Grant
- 2000-12-22 CA CA002395869A patent/CA2395869C/en not_active Expired - Fee Related
- 2000-12-22 AU AU21527/01A patent/AU783786B2/en not_active Ceased
- 2000-12-22 EP EP04007739A patent/EP1464641B1/en not_active Expired - Lifetime
- 2000-12-22 CN CNA2005101310970A patent/CN1803784A/zh active Pending
- 2000-12-22 DK DK04007739T patent/DK1464641T3/da active
- 2000-12-22 AT AT04007739T patent/ATE395333T1/de not_active IP Right Cessation
- 2000-12-22 DE DE60011817T patent/DE60011817T2/de not_active Expired - Fee Related
- 2000-12-22 TR TR2004/02408T patent/TR200402408T4/xx unknown
- 2000-12-22 PT PT04007739T patent/PT1464641E/pt unknown
- 2000-12-22 DE DE60038911T patent/DE60038911D1/de not_active Expired - Fee Related
- 2000-12-22 KR KR1020027008576A patent/KR100729536B1/ko not_active IP Right Cessation
- 2000-12-22 BR BR0016953-6A patent/BR0016953A/pt not_active Application Discontinuation
- 2000-12-22 TR TR2002/01690T patent/TR200201690T2/xx unknown
- 2000-12-22 JP JP2001550219A patent/JP2003519225A/ja active Pending
- 2000-12-22 NZ NZ530137A patent/NZ530137A/en unknown
- 2000-12-22 UA UA2002065264A patent/UA73756C2/uk unknown
- 2000-12-22 CZ CZ20022603A patent/CZ20022603A3/cs unknown
- 2000-12-28 AR ARP000106991A patent/AR029461A1/es not_active Application Discontinuation
2002
- 2002-06-19 IS IS6432A patent/IS6432A/is unknown
- 2002-06-21 ZA ZA200205019A patent/ZA200205019B/en unknown
- 2002-06-23 IL IL150366A patent/IL150366A/en not_active IP Right Cessation
- 2002-06-27 US US10/186,339 patent/US7074796B2/en not_active Expired - Fee Related
- 2002-06-28 NO NO20023151A patent/NO323401B1/no unknown
- 2002-07-03 HR HR20020567A patent/HRP20020567A2/hr not_active Application Discontinuation
- 2002-07-26 BG BG106960A patent/BG106960A/bg unknown
2003
- 2003-11-13 HK HK03108252A patent/HK1055960A1/xx unknown
2006
- 2006-03-08 AU AU2006201000A patent/AU2006201000A1/en not_active Abandoned
- 2006-03-15 US US11/377,772 patent/US7223765B2/en not_active Expired - Fee Related
- 2006-12-14 NO NO20065681A patent/NO20065681L/no not_active Application Discontinuation
2007
- 2007-10-25 IL IL186954A patent/IL186954A0/en unknown

Also Published As

Publication number	Publication date
EA008627B1 (ru)	2007-06-29
DK1464641T3 (da)	2008-08-18
DE60038911D1 (de)	2008-06-26
CN1434819A (zh)	2003-08-06
PL355502A1 (en)	2004-05-04
KR100729536B1 (ko)	2007-06-18
BG106960A (bg)	2003-04-30
AR029461A1 (es)	2003-07-02
HUP0203839A3 (en)	2004-07-28
KR100792186B1 (ko)	2008-01-08
NZ530137A (en)	2005-09-30
CA2395869A1 (en)	2001-07-12
BR0016953A (pt)	2003-02-25
PT1246817E (pt)	2004-11-30
HUP0203839A2 (hu)	2003-02-28
DE60011817D1 (de)	2004-07-29
EA005013B1 (ru)	2004-10-28
ES2223628T3 (es)	2005-03-01
ZA200205019B (en)	2003-09-22
JP2003519225A (ja)	2003-06-17
MXPA02006590A (es)	2002-12-13
AU783786B2 (en)	2005-12-08
NO20023151L (no)	2002-08-02
DK1246817T3 (da)	2004-10-18
US7223765B2 (en)	2007-05-29
UA73756C2 (en)	2005-09-15
US7074796B2 (en)	2006-07-11
HRP20020567A2 (en)	2005-04-30
PT1464641E (pt)	2008-07-01
EP1246817B1 (en)	2004-06-23
CA2395869C (en)	2006-07-25
EP1464641B1 (en)	2008-05-14
ATE269857T1 (de)	2004-07-15
CN1803784A (zh)	2006-07-19
EP1464641A1 (en)	2004-10-06
NO20023151D0 (no)	2002-06-28
WO2001049679A1 (en)	2001-07-12
NZ519740A (en)	2004-03-26
SK11072002A3 (sk)	2003-03-04
US20030027832A1 (en)	2003-02-06
NO20065681L (no)	2002-08-02
IL150366A0 (en)	2002-12-01
DE60011817T2 (de)	2005-07-14
EA200400641A1 (ru)	2004-10-28
IL150366A (en)	2008-06-05
SG152900A1 (en)	2009-06-29
US20060148815A1 (en)	2006-07-06
EA200200729A1 (ru)	2002-12-26
KR20020063285A (ko)	2002-08-01
TR200201690T2 (tr)	2002-11-21
ES2302992T3 (es)	2008-08-01
HK1055960A1 (en)	2004-01-30
CN1244577C (zh)	2006-03-08
IL186954A0 (en)	2009-02-11
TR200402408T4 (tr)	2004-12-21
AU2006201000A1 (en)	2006-04-06
AU2152701A (en)	2001-07-16
ATE395333T1 (de)	2008-05-15
KR20070014234A (ko)	2007-01-31
IS6432A (is)	2002-06-19
CZ20022603A3 (cs)	2002-10-16
EP1246817A1 (en)	2002-10-09

Publication	Publication Date	Title
US7223765B2 (en)	2007-05-29	4-phenyl-1-piperazinyl, -piperidinyl and -tetrahydropyridyl derivatives
SK11062002A3 (sk)	2002-12-03	Fenylpiperazínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie
PL199351B1 (pl)	2008-09-30	Związki pochodne fenylopiperazyny, zawierająca je kompozycja farmaceutyczna i ich zastosowanie
NZ519648A (en)	2004-05-28	Indole derivatives useful as 5HT1A receptor agonists
AU2001273881A1 (en)	2002-03-14	Indole derivatives useful for the treatment of CNS disorders
WO2001096328A1 (en)	2001-12-20	Indole derivatives useful for the treatment of cns disorders
NZ540801A (en)	2007-05-31	4-Phenyl-1-piperazinyl, -piperidinyl and -tetrahydropyridyl derivatives
MXPA02012149A (en)	2008-10-03	Indole derivatives useful for the treatment of cns disorders