ZA200701972B - Phenyl diazepane carboxamides and annelated phenyl piperazine carboxamides containing oxygen and used as dopamine D3 antagonists - Google Patents
Phenyl diazepane carboxamides and annelated phenyl piperazine carboxamides containing oxygen and used as dopamine D3 antagonists Download PDFInfo
- Publication number
- ZA200701972B ZA200701972B ZA200701972A ZA200701972A ZA200701972B ZA 200701972 B ZA200701972 B ZA 200701972B ZA 200701972 A ZA200701972 A ZA 200701972A ZA 200701972 A ZA200701972 A ZA 200701972A ZA 200701972 B ZA200701972 B ZA 200701972B
- Authority
- ZA
- South Africa
- Prior art keywords
- ylcarbamide
- butyl
- piperazine
- benzo
- thiophene
- Prior art date
Links
- 229910052760 oxygen Inorganic materials 0.000 title claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 7
- 239000001301 oxygen Substances 0.000 title claims description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title description 12
- 229960003638 dopamine Drugs 0.000 title description 6
- 239000005557 antagonist Substances 0.000 title description 3
- FKRLWISOOAJICU-UHFFFAOYSA-N n-phenyldiazepane-1-carboxamide Chemical class C1CCCCNN1C(=O)NC1=CC=CC=C1 FKRLWISOOAJICU-UHFFFAOYSA-N 0.000 title 1
- YEQDVKYOHVLZPU-UHFFFAOYSA-N n-phenylpiperazine-1-carboxamide Chemical class C1CNCCN1C(=O)NC1=CC=CC=C1 YEQDVKYOHVLZPU-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000005605 benzo group Chemical group 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 35
- 239000000460 chlorine Substances 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 35
- 239000011737 fluorine Substances 0.000 claims description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000006193 alkinyl group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- -1 cyano, nitro, amino, carboxy, sulfo, sulfamoyl Chemical group 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000006735 deficit Effects 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 4
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 208000031424 hyperprolactinemia Diseases 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 4
- 206010003805 Autism Diseases 0.000 claims description 3
- 208000020706 Autistic disease Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 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 2
- 239000012458 free base Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 5
- 206010046543 Urinary incontinence Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010028813 Nausea Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000016620 Tourette disease Diseases 0.000 claims 2
- 208000026723 Urinary tract disease Diseases 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 230000008693 nausea Effects 0.000 claims 2
- 208000014001 urinary system disease Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 239000003176 neuroleptic agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 29
- 239000003446 ligand Substances 0.000 description 7
- 108050004812 Dopamine receptor Proteins 0.000 description 6
- 102000015554 Dopamine receptor Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000012661 Dyskinesia Diseases 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 230000004770 neurodegeneration Effects 0.000 description 3
- 239000004031 partial agonist Substances 0.000 description 3
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 description 2
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 2
- 125000006852 aliphatic spacer Chemical group 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 description 1
- XXOQJWXDRPURJK-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1-benzoxepine Chemical compound O1CCCCC2=CC=CC=C21 XXOQJWXDRPURJK-UHFFFAOYSA-N 0.000 description 1
- SLQITXDMNLWAEY-UHFFFAOYSA-N 3-phenyl-2-piperazin-1-ylnaphthalene-1-carboxamide Chemical compound C=1C=CC=CC=1C1=CC2=CC=CC=C2C(C(=O)N)=C1N1CCNCC1 SLQITXDMNLWAEY-UHFFFAOYSA-N 0.000 description 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 1
- 206010001540 Akathisia Diseases 0.000 description 1
- 206010008531 Chills Diseases 0.000 description 1
- 208000022497 Cocaine-Related disease Diseases 0.000 description 1
- 101150049660 DRD2 gene Proteins 0.000 description 1
- 102000004073 Dopamine D3 Receptors Human genes 0.000 description 1
- 108090000525 Dopamine D3 Receptors Proteins 0.000 description 1
- 208000014094 Dystonic disease Diseases 0.000 description 1
- 102000017911 HTR1A Human genes 0.000 description 1
- 101150015707 HTR1A gene Proteins 0.000 description 1
- 101000822895 Homo sapiens 5-hydroxytryptamine receptor 1A Proteins 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 101001135571 Mus musculus Tyrosine-protein phosphatase non-receptor type 2 Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 210000004227 basal ganglia Anatomy 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 201000006145 cocaine dependence Diseases 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical group C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 208000010118 dystonia Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000010491 emotional process Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000001095 motoneuron effect Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 230000007121 neuropathological change Effects 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
Classifications
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A61P25/20—Hypnotics; Sedatives
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- External Artificial Organs (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004063797A DE102004063797A1 (de) | 2004-12-30 | 2004-12-30 | Sauerstoffhaltige annelierte Phenylpiperazin- und Phenyldiazepancarboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200701972B true ZA200701972B (en) | 2008-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200701972A ZA200701972B (en) | 2004-12-30 | 2007-01-18 | Phenyl diazepane carboxamides and annelated phenyl piperazine carboxamides containing oxygen and used as dopamine D3 antagonists |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20080194539A1 (fr) |
| EP (1) | EP1761524B1 (fr) |
| JP (1) | JP2008526700A (fr) |
| KR (1) | KR20070102673A (fr) |
| CN (1) | CN101027294A (fr) |
| AU (1) | AU2005324107A1 (fr) |
| BR (1) | BRPI0519485A2 (fr) |
| CA (1) | CA2576332A1 (fr) |
| DE (2) | DE102004063797A1 (fr) |
| DK (1) | DK1761524T3 (fr) |
| EA (1) | EA200701366A1 (fr) |
| ES (1) | ES2297767T3 (fr) |
| HK (1) | HK1100845A1 (fr) |
| HR (1) | HRP20080075T3 (fr) |
| IL (1) | IL180763A0 (fr) |
| MX (1) | MX2007006369A (fr) |
| NO (1) | NO20072587L (fr) |
| PL (1) | PL1761524T3 (fr) |
| PT (1) | PT1761524E (fr) |
| SI (1) | SI1761524T1 (fr) |
| WO (1) | WO2006072430A1 (fr) |
| ZA (1) | ZA200701972B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9227944B2 (en) | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
| WO2010040274A1 (fr) * | 2008-10-10 | 2010-04-15 | 中国人民解放军军事医学科学院毒物药物研究所 | Nouveaux ligands de récepteurs d3 de la dopamine, leurs procédés de préparation et leurs applications |
| UY32481A (es) * | 2009-03-10 | 2010-09-30 | Takeda Pharmaceutical | Derivados de benzofurano |
| ES2729824T3 (es) * | 2011-04-08 | 2019-11-06 | Laurus Labs Ltd | Formas sólidas de compuestos antirretrovirales, procedimiento para la preparación y composición farmacéutica de los mismos |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL90279A (en) * | 1988-05-24 | 1995-03-30 | American Home Prod | History of piperazinyl carboxamide, their preparation and the pharmaceutical preparations containing them |
| CA2004670A1 (fr) * | 1988-12-08 | 1990-06-08 | Jan Hartog | Derives de la piperazine a effet anxiolytique |
| DE4127849A1 (de) * | 1991-08-22 | 1993-02-25 | Merck Patent Gmbh | Benzodioxanderivate |
| DE4333254A1 (de) * | 1993-09-30 | 1995-04-06 | Merck Patent Gmbh | Piperidine und Piperazine |
| EP1007523B9 (fr) * | 1997-07-25 | 2004-09-08 | H. Lundbeck A/S | Derives indole et 2,3-dihydro-indole, leur preparation et utilisation |
| FR2781671A1 (fr) * | 1998-07-28 | 2000-02-04 | Synthelabo | Compositions pharmaceutiques contenant un inhibiteur de la recapture de la serotonine et leur application en therapeutique |
| AR022303A1 (es) * | 1999-01-22 | 2002-09-04 | Lundbeck & Co As H | Derivados de piperidina, tetrahidropiridina y piperazina, su preparacion y utilizacion |
| GB9905010D0 (en) * | 1999-03-04 | 1999-04-28 | Merck Sharp & Dohme | Therapeutic agents |
| ES2188344B1 (es) * | 2000-11-29 | 2004-09-16 | Laboratorios Vita, S.A. | Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos. |
| HUP0103987A3 (en) * | 2001-09-28 | 2004-11-29 | Richter Gedeon Vegyeszet | Phenylpiperazinylalkyl carboxylic acid amid derivatives, process for their preparation, pharmaceutical compositions containing them and their intermediates |
| KR20050075281A (ko) * | 2002-07-04 | 2005-07-20 | 쉬바르츠파르마에이지 | 씨엔에스 질병의 치료를 위한 도파민-디3 리간드로서헤테로아렌 카복스아미드의 용도 |
| US7605259B2 (en) * | 2002-09-14 | 2009-10-20 | University Of North Texas Health Science Center At Fort Worth | Structurally rigid dopamine d3 receptor selective ligands and process for making them |
| DE10259244A1 (de) * | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | N-(Indolethyl-)cycloamin-Verbindungen |
| US20040192730A1 (en) * | 2003-03-13 | 2004-09-30 | Dynogen Pharmaceuticals, Inc. | Methods of using compounds with combined 5-HT1A and SSRI activities as-needed to treat sexual dysfunction |
-
2004
- 2004-12-30 DE DE102004063797A patent/DE102004063797A1/de not_active Ceased
-
2005
- 2005-12-27 PT PT05823871T patent/PT1761524E/pt unknown
- 2005-12-27 MX MX2007006369A patent/MX2007006369A/es not_active Application Discontinuation
- 2005-12-27 AU AU2005324107A patent/AU2005324107A1/en not_active Abandoned
- 2005-12-27 EA EA200701366A patent/EA200701366A1/ru unknown
- 2005-12-27 KR KR1020077014615A patent/KR20070102673A/ko not_active Application Discontinuation
- 2005-12-27 EP EP05823871A patent/EP1761524B1/fr active Active
- 2005-12-27 SI SI200530145T patent/SI1761524T1/sl unknown
- 2005-12-27 DE DE502005002058T patent/DE502005002058D1/de not_active Expired - Fee Related
- 2005-12-27 CA CA002576332A patent/CA2576332A1/fr not_active Abandoned
- 2005-12-27 DK DK05823871T patent/DK1761524T3/da active
- 2005-12-27 BR BRPI0519485-7A patent/BRPI0519485A2/pt not_active Application Discontinuation
- 2005-12-27 ES ES05823871T patent/ES2297767T3/es active Active
- 2005-12-27 PL PL05823871T patent/PL1761524T3/pl unknown
- 2005-12-27 WO PCT/EP2005/014047 patent/WO2006072430A1/fr active IP Right Grant
- 2005-12-27 US US11/794,386 patent/US20080194539A1/en not_active Abandoned
- 2005-12-27 JP JP2007548748A patent/JP2008526700A/ja active Pending
- 2005-12-27 CN CNA2005800324230A patent/CN101027294A/zh active Pending
-
2007
- 2007-01-17 IL IL180763A patent/IL180763A0/en unknown
- 2007-01-18 ZA ZA200701972A patent/ZA200701972B/en unknown
- 2007-05-21 NO NO20072587A patent/NO20072587L/no not_active Application Discontinuation
- 2007-06-05 HK HK07105930A patent/HK1100845A1/xx not_active IP Right Cessation
-
2008
- 2008-02-19 HR HR20080075T patent/HRP20080075T3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20080194539A1 (en) | 2008-08-14 |
| KR20070102673A (ko) | 2007-10-19 |
| DE102004063797A1 (de) | 2006-07-13 |
| HRP20080075T3 (en) | 2008-03-31 |
| HK1100845A1 (en) | 2007-09-28 |
| SI1761524T1 (sl) | 2008-04-30 |
| CN101027294A (zh) | 2007-08-29 |
| DE502005002058D1 (de) | 2008-01-03 |
| EP1761524B1 (fr) | 2007-11-21 |
| EA200701366A1 (ru) | 2008-02-28 |
| PL1761524T3 (pl) | 2008-04-30 |
| AU2005324107A1 (en) | 2006-07-13 |
| CA2576332A1 (fr) | 2006-07-13 |
| IL180763A0 (en) | 2007-06-03 |
| PT1761524E (pt) | 2008-02-21 |
| MX2007006369A (es) | 2007-07-11 |
| JP2008526700A (ja) | 2008-07-24 |
| ES2297767T3 (es) | 2008-05-01 |
| NO20072587L (no) | 2007-05-21 |
| WO2006072430A1 (fr) | 2006-07-13 |
| DK1761524T3 (da) | 2008-04-07 |
| EP1761524A1 (fr) | 2007-03-14 |
| BRPI0519485A2 (pt) | 2009-02-03 |
| AU2005324107A2 (en) | 2006-07-13 |
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