UA73995C2 - Indole derivatives being useful for the treatment of cns disorders,, a pharmaceutical composition and a method for treatment - Google Patents
Indole derivatives being useful for the treatment of cns disorders,, a pharmaceutical composition and a method for treatment Download PDFInfo
- Publication number
- UA73995C2 UA73995C2 UA2003010167A UA2003010167A UA73995C2 UA 73995 C2 UA73995 C2 UA 73995C2 UA 2003010167 A UA2003010167 A UA 2003010167A UA 2003010167 A UA2003010167 A UA 2003010167A UA 73995 C2 UA73995 C2 UA 73995C2
- Authority
- UA
- Ukraine
- Prior art keywords
- indole
- ethyl
- piperidin
- chloro
- methylphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000002475 indoles Chemical class 0.000 title claims description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 14
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 9
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 5
- 206010027599 migraine Diseases 0.000 claims abstract description 5
- 230000007958 sleep Effects 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 124
- -1 cyano, nitro, amino, hydroxy group Chemical group 0.000 claims description 91
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 16
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000000164 antipsychotic agent Substances 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 230000016571 aggressive behavior Effects 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 4
- 208000019906 panic disease Diseases 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims description 3
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000003441 thioacyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 229960003638 dopamine Drugs 0.000 abstract description 22
- 239000003446 ligand Substances 0.000 abstract description 7
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract description 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 abstract description 3
- 208000012902 Nervous system disease Diseases 0.000 abstract description 2
- 208000025966 Neurological disease Diseases 0.000 abstract description 2
- 230000006872 improvement Effects 0.000 abstract description 2
- 208000020016 psychiatric disease Diseases 0.000 abstract description 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- 239000000203 mixture Substances 0.000 description 46
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
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- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
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- 239000004031 partial agonist Substances 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JCSRJKWRJVUXSQ-UHFFFAOYSA-N 2-(2-methyl-5-nitrophenyl)acetic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1CC(O)=O JCSRJKWRJVUXSQ-UHFFFAOYSA-N 0.000 description 4
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 4
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- GDPRTNRLCIICFQ-UHFFFAOYSA-N thiadiazole-5-carbonyl chloride Chemical compound ClC(=O)C1=CN=NS1 GDPRTNRLCIICFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200001123 | 2000-07-21 | ||
| PCT/DK2001/000507 WO2002008223A1 (en) | 2000-07-21 | 2001-07-17 | Indole derivatives useful for the treatment of cns disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73995C2 true UA73995C2 (en) | 2005-10-17 |
Family
ID=8159625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003010167A UA73995C2 (en) | 2000-07-21 | 2001-07-17 | Indole derivatives being useful for the treatment of cns disorders,, a pharmaceutical composition and a method for treatment |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6743809B2 (tr) |
| EP (1) | EP1305307B1 (tr) |
| JP (1) | JP2004504396A (tr) |
| KR (1) | KR100851793B1 (tr) |
| CN (1) | CN1264838C (tr) |
| AR (1) | AR029858A1 (tr) |
| AT (1) | ATE266024T1 (tr) |
| AU (2) | AU8173801A (tr) |
| BG (1) | BG107528A (tr) |
| BR (1) | BR0112998A (tr) |
| CA (1) | CA2416212C (tr) |
| CZ (1) | CZ301114B6 (tr) |
| DE (1) | DE60103162T2 (tr) |
| EA (1) | EA004749B1 (tr) |
| ES (1) | ES2219554T3 (tr) |
| HK (1) | HK1059782A1 (tr) |
| HR (1) | HRP20030015A2 (tr) |
| HU (1) | HUP0302820A3 (tr) |
| IL (2) | IL153605A0 (tr) |
| IS (1) | IS2172B (tr) |
| MX (1) | MXPA02012927A (tr) |
| NO (1) | NO323799B1 (tr) |
| NZ (1) | NZ523436A (tr) |
| PT (1) | PT1305307E (tr) |
| SK (1) | SK286701B6 (tr) |
| TR (1) | TR200401488T4 (tr) |
| UA (1) | UA73995C2 (tr) |
| WO (1) | WO2002008223A1 (tr) |
| ZA (1) | ZA200300287B (tr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004291297B2 (en) | 2003-11-17 | 2011-06-23 | Boehringer Ingelheim International Gmbh | Novel piperidine-substituted indoles- or heteroderivatives thereof |
| TWI391387B (zh) * | 2004-05-12 | 2013-04-01 | Eisai R&D Man Co Ltd | 具有哌啶環之吲哚衍生物 |
| EP1994019B1 (en) | 2005-04-30 | 2011-11-02 | Boehringer Ingelheim International GmbH | Novel piperidin - substituted indoles and their use as ccr-3 modulators |
| EP2079725B1 (en) | 2006-10-27 | 2011-12-14 | Boehringer Ingelheim International GmbH | Piperidyl-propane-thiol ccr3 modulators |
| CN101486654B (zh) * | 2009-03-04 | 2012-10-10 | 西安近代化学研究所 | 2-甲基-3-硝基苯乙酸合成方法 |
| CN110041318B (zh) * | 2018-01-17 | 2022-07-29 | 中国科学院上海药物研究所 | 一类多巴胺d5受体激动剂及其制备和应用 |
| CN110498789B (zh) * | 2018-05-17 | 2022-04-05 | 上海医药工业研究院 | 芳烷哌啶类衍生物及其在多靶点抗抑郁症中的应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2322470A1 (de) * | 1973-05-04 | 1974-11-21 | Boehringer Sohn Ingelheim | Neue indolyl-piperidino-(bzw. 1,2,5,6tetrahydro-pyridyl-)butyrophenone und verfahren zu ihrer herstellung |
| AT332401B (de) * | 1973-11-26 | 1976-09-27 | Roussel Uclaf | Verfahren zur herstellung von neuen (4'-(3''-indolyl)-piperidino)-alkylarylketonderivaten |
| ATE92057T1 (de) * | 1987-08-13 | 1993-08-15 | Glaxo Group Ltd | Indol-derivate. |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| EP0664801A1 (en) * | 1992-08-05 | 1995-08-02 | JOHN WYETH & BROTHER LIMITED | Amide derivatives |
| ATE144773T1 (de) * | 1993-04-22 | 1996-11-15 | Pfizer Res & Dev | Indol-derivate als 5-ht1-ähnliche antagonisten zur behandlung von migräne |
| ES2063700B1 (es) * | 1993-04-28 | 1995-07-16 | Vita Invest Sa | Agente activo sobre el sistema nervioso central, proceso para su preparacion y composiciones farmaceuticas que lo contengan. |
| US5576321A (en) * | 1995-01-17 | 1996-11-19 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| GB9718712D0 (en) * | 1997-09-03 | 1997-11-12 | Merck Sharp & Dohme | Theraputic Agents |
-
2001
- 2001-07-17 MX MXPA02012927A patent/MXPA02012927A/es active IP Right Grant
- 2001-07-17 UA UA2003010167A patent/UA73995C2/uk unknown
- 2001-07-17 HU HU0302820A patent/HUP0302820A3/hu unknown
- 2001-07-17 JP JP2002514129A patent/JP2004504396A/ja active Pending
- 2001-07-17 TR TR2004/01488T patent/TR200401488T4/tr unknown
- 2001-07-17 ES ES01960182T patent/ES2219554T3/es not_active Expired - Lifetime
- 2001-07-17 SK SK203-2003A patent/SK286701B6/sk not_active IP Right Cessation
- 2001-07-17 EA EA200300179A patent/EA004749B1/ru not_active IP Right Cessation
- 2001-07-17 IL IL15360501A patent/IL153605A0/xx unknown
- 2001-07-17 AT AT01960182T patent/ATE266024T1/de not_active IP Right Cessation
- 2001-07-17 EP EP01960182A patent/EP1305307B1/en not_active Expired - Lifetime
- 2001-07-17 BR BR0112998-8A patent/BR0112998A/pt not_active IP Right Cessation
- 2001-07-17 NZ NZ523436A patent/NZ523436A/en unknown
- 2001-07-17 WO PCT/DK2001/000507 patent/WO2002008223A1/en active IP Right Grant
- 2001-07-17 CA CA002416212A patent/CA2416212C/en not_active Expired - Fee Related
- 2001-07-17 AU AU8173801A patent/AU8173801A/xx active Pending
- 2001-07-17 AU AU2001281738A patent/AU2001281738B2/en not_active Ceased
- 2001-07-17 CZ CZ20030196A patent/CZ301114B6/cs not_active IP Right Cessation
- 2001-07-17 DE DE60103162T patent/DE60103162T2/de not_active Expired - Fee Related
- 2001-07-17 PT PT01960182T patent/PT1305307E/pt unknown
- 2001-07-17 CN CNB018151078A patent/CN1264838C/zh not_active Expired - Fee Related
- 2001-07-17 KR KR1020037000850A patent/KR100851793B1/ko not_active IP Right Cessation
- 2001-07-20 AR ARP010103457A patent/AR029858A1/es unknown
-
2002
- 2002-12-23 IS IS6663A patent/IS2172B/is unknown
- 2002-12-24 IL IL153605A patent/IL153605A/en not_active IP Right Cessation
-
2003
- 2003-01-09 HR HR20030015A patent/HRP20030015A2/hr not_active Application Discontinuation
- 2003-01-10 NO NO20030127A patent/NO323799B1/no not_active IP Right Cessation
- 2003-01-10 ZA ZA200300287A patent/ZA200300287B/en unknown
- 2003-01-17 US US10/347,574 patent/US6743809B2/en not_active Expired - Fee Related
- 2003-02-05 BG BG107528A patent/BG107528A/bg unknown
-
2004
- 2004-04-15 HK HK04102653A patent/HK1059782A1/xx not_active IP Right Cessation
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