UA74651C2 - Indole derivatives, a pharmaceutical composition based thereon and use thereof - Google Patents

Indole derivatives, a pharmaceutical composition based thereon and use thereof Download PDF

Info

Publication number: UA74651C2
Authority: UA; Ukraine
Prior art keywords: indol; piperazin; alkyl; disorder; compound
Prior art date: 2001-06-29

Application number

UA20031211983A

Other languages

English (en)

Ukrainian (uk)

Inventor

Einer Knud Moltsen

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.)

2001-06-29

Filing date

2002-06-27

Publication date

2006-01-16

2002-06-27 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2006-01-16 Publication of UA74651C2 publication Critical patent/UA74651C2/uk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000002475 indoles Chemical class 0.000 title description 4
229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 77
208000028017 Psychotic disease Diseases 0.000 claims abstract description 9
208000019906 panic disease Diseases 0.000 claims abstract description 9
208000012902 Nervous system disease Diseases 0.000 claims abstract description 8
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 8
208000019022 Mood disease Diseases 0.000 claims abstract description 7
208000025966 Neurological disease Diseases 0.000 claims abstract description 7
206010041250 Social phobia Diseases 0.000 claims abstract description 7
208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 66
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 27
238000000034 method Methods 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 16
229960003638 dopamine Drugs 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 13
230000005764 inhibitory process Effects 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
208000011688 Generalised anxiety disease Diseases 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 7
208000029364 generalized anxiety disease Diseases 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
208000027559 Appetite disease Diseases 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
230000008485 antagonism Effects 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229940126601 medicinal product Drugs 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 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 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
230000013275 serotonin uptake Effects 0.000 claims description 3
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
208000037765 diseases and disorders Diseases 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
208000017194 Affective disease Diseases 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims 1
230000008517 inhibition of serotonin uptake Effects 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
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GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
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125000001072 heteroaryl group Chemical group 0.000 abstract description 2
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238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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238000012360 testing method Methods 0.000 description 14
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239000000203 mixture Substances 0.000 description 12
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VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
229940079593 drug Drugs 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000005557 antagonist Substances 0.000 description 6
239000003446 ligand Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000004949 mass spectrometry Methods 0.000 description 5
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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208000024827 Alzheimer disease Diseases 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 2
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
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FBCZWQNVHNIQOD-UHFFFAOYSA-N 2-piperazin-1-yl-1h-indole Chemical class C1CNCCN1C1=CC2=CC=CC=C2N1 FBCZWQNVHNIQOD-UHFFFAOYSA-N 0.000 description 1
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206010027599 migraine Diseases 0.000 description 1
125000002950 monocyclic group Chemical group 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
125000001624 naphthyl group Chemical group 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000000926 neurological effect Effects 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
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
239000000952 serotonin receptor agonist Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
238000011064 split stream procedure Methods 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
150000003892 tartrate salts Chemical class 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- C07D401/14—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 three or more hetero rings
- 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
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- 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
- A61P25/20—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
- A61P25/22—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

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

UA20031211983A 2001-06-29 2002-06-27 Indole derivatives, a pharmaceutical composition based thereon and use thereof UA74651C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200101037		2001-06-29
PCT/DK2002/000436 WO2003002552A1 (en)	2001-06-29	2002-06-27	Novel indole derivatives

Publications (1)

Publication Number	Publication Date
UA74651C2 true UA74651C2 (en)	2006-01-16

Family

ID=8160599

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20031211983A UA74651C2 (en)	2001-06-29	2002-06-27	Indole derivatives, a pharmaceutical composition based thereon and use thereof

Country Status (27)

Country	Link
US (1)	US7342015B2 (cs)
EP (1)	EP1399434B1 (cs)
JP (1)	JP2004535448A (cs)
KR (1)	KR20040019027A (cs)
CN (1)	CN100338058C (cs)
AR (1)	AR034658A1 (cs)
AT (1)	ATE304007T1 (cs)
AU (1)	AU2002344950B2 (cs)
BG (1)	BG108538A (cs)
BR (1)	BR0210407A (cs)
CA (1)	CA2451229C (cs)
CZ (1)	CZ2004155A3 (cs)
DE (1)	DE60206043T2 (cs)
DK (1)	DK1399434T3 (cs)
EA (1)	EA006104B1 (cs)
ES (1)	ES2247347T3 (cs)
HU (1)	HUP0400834A2 (cs)
IL (1)	IL158830A0 (cs)
IS (1)	IS2431B (cs)
MX (1)	MXPA03011766A (cs)
NO (1)	NO326513B1 (cs)
NZ (1)	NZ529461A (cs)
PL (1)	PL366520A1 (cs)
SK (1)	SK642004A3 (cs)
UA (1)	UA74651C2 (cs)
WO (1)	WO2003002552A1 (cs)
ZA (1)	ZA200308848B (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2451228A1 (en) *	2001-06-29	2003-01-09	H. Lundbeck A/S	Novel heteroaryl derivatives, their preparation and use
US7635696B2 (en)	2004-11-26	2009-12-22	Janssen Pharmaceutica N.V.	Isoxazoline-indole derivatives with an improved antipsychotic and anxiolytic activity
AR055203A1 (es) *	2005-08-31	2007-08-08	Otsuka Pharma Co Ltd	Derivados de benzotiofeno con propiedades antipsicoticas
JP4785881B2 (ja) *	2007-02-27	2011-10-05	大塚製薬株式会社	医薬
CN116554145B (zh) *	2022-01-29	2025-06-03	江苏恩华药业股份有限公司	芳烷基-4-(1h)吲哚基哌嗪衍生物、其制备方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0900792B1 (en) *	1997-09-02	2003-10-29	Duphar International Research B.V	Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists
AR015036A1 (es)	1998-04-29	2001-04-11	American Home Prod	Derivados de indolilo antisicoticos, composicion farmaceutica que los contiene y su uso para la manufactura de un medicamento
AR027134A1 (es) *	1999-12-30	2003-03-12	Lundbeck & Co As H	Derivados de indol.
CA2451228A1 (en)	2001-06-29	2003-01-09	H. Lundbeck A/S	Novel heteroaryl derivatives, their preparation and use

2002
- 2002-06-27 CN CNB028131878A patent/CN100338058C/zh not_active Expired - Fee Related
- 2002-06-27 ES ES02742850T patent/ES2247347T3/es not_active Expired - Lifetime
- 2002-06-27 PL PL02366520A patent/PL366520A1/xx not_active Application Discontinuation
- 2002-06-27 NZ NZ529461A patent/NZ529461A/en unknown
- 2002-06-27 MX MXPA03011766A patent/MXPA03011766A/es active IP Right Grant
- 2002-06-27 WO PCT/DK2002/000436 patent/WO2003002552A1/en not_active Ceased
- 2002-06-27 EA EA200400104A patent/EA006104B1/ru not_active IP Right Cessation
- 2002-06-27 AT AT02742850T patent/ATE304007T1/de not_active IP Right Cessation
- 2002-06-27 HU HU0400834A patent/HUP0400834A2/hu unknown
- 2002-06-27 US US10/482,762 patent/US7342015B2/en not_active Expired - Fee Related
- 2002-06-27 IL IL15883002A patent/IL158830A0/xx unknown
- 2002-06-27 DE DE60206043T patent/DE60206043T2/de not_active Expired - Fee Related
- 2002-06-27 KR KR10-2003-7017127A patent/KR20040019027A/ko not_active Ceased
- 2002-06-27 JP JP2003508933A patent/JP2004535448A/ja active Pending
- 2002-06-27 SK SK64-2004A patent/SK642004A3/sk unknown
- 2002-06-27 UA UA20031211983A patent/UA74651C2/uk unknown
- 2002-06-27 AU AU2002344950A patent/AU2002344950B2/en not_active Ceased
- 2002-06-27 CA CA002451229A patent/CA2451229C/en not_active Expired - Fee Related
- 2002-06-27 EP EP02742850A patent/EP1399434B1/en not_active Expired - Lifetime
- 2002-06-27 BR BR0210407-5A patent/BR0210407A/pt not_active IP Right Cessation
- 2002-06-27 CZ CZ2004155A patent/CZ2004155A3/cs unknown
- 2002-06-27 DK DK02742850T patent/DK1399434T3/da active
- 2002-06-28 AR ARP020102449A patent/AR034658A1/es unknown
2003
- 2003-11-10 IS IS7022A patent/IS2431B/is unknown
- 2003-11-13 ZA ZA200308848A patent/ZA200308848B/en unknown
- 2003-12-18 NO NO20035672A patent/NO326513B1/no unknown
2004
- 2004-01-21 BG BG108538A patent/BG108538A/bg unknown

Also Published As

Publication number	Publication date
EA006104B1 (ru)	2005-08-25
CA2451229A1 (en)	2003-01-09
ES2247347T3 (es)	2006-03-01
HK1069579A1 (zh)	2005-05-27
EP1399434A1 (en)	2004-03-24
IS2431B (is)	2008-10-15
NZ529461A (en)	2005-09-30
NO20035672D0 (no)	2003-12-18
MXPA03011766A (es)	2004-04-02
KR20040019027A (ko)	2004-03-04
EP1399434B1 (en)	2005-09-07
CN100338058C (zh)	2007-09-19
CA2451229C (en)	2009-02-10
ZA200308848B (en)	2006-02-22
DE60206043D1 (de)	2005-10-13
DK1399434T3 (da)	2005-12-12
SK642004A3 (en)	2004-05-04
US20060258678A1 (en)	2006-11-16
IS7022A (is)	2003-11-10
AU2002344950B2 (en)	2008-04-03
BR0210407A (pt)	2004-08-17
PL366520A1 (en)	2005-02-07
CZ2004155A3 (cs)	2004-07-14
AR034658A1 (es)	2004-03-03
NO20035672L (no)	2003-12-18
US7342015B2 (en)	2008-03-11
NO326513B1 (no)	2008-12-22
JP2004535448A (ja)	2004-11-25
BG108538A (bg)	2005-01-31
DE60206043T2 (de)	2006-06-29
WO2003002552A1 (en)	2003-01-09
CN1529703A (zh)	2004-09-15
EA200400104A1 (ru)	2004-04-29
ATE304007T1 (de)	2005-09-15
HUP0400834A2 (hu)	2004-08-30
IL158830A0 (en)	2004-05-12

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