CA2546591A1 - Use of 3-aza-1-oxa-dibenzo [e,h] azulenes for the manufacture of pharmaceutical formulations for the treatment and prevention of central nervous system diseases and disorders - Google Patents
Use of 3-aza-1-oxa-dibenzo [e,h] azulenes for the manufacture of pharmaceutical formulations for the treatment and prevention of central nervous system diseases and disorders Download PDFInfo
- Publication number
- CA2546591A1 CA2546591A1 CA002546591A CA2546591A CA2546591A1 CA 2546591 A1 CA2546591 A1 CA 2546591A1 CA 002546591 A CA002546591 A CA 002546591A CA 2546591 A CA2546591 A CA 2546591A CA 2546591 A1 CA2546591 A1 CA 2546591A1
- Authority
- CA
- Canada
- Prior art keywords
- aza
- dibenzo
- oxa
- azulen
- thia
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 16
- ACYHNAHLXFLGLX-UHFFFAOYSA-N 3-oxa-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1,5,7,9,11,13,15,17-octaene Chemical class C=1C2=CC=CC=C2C2=NCOC2=C2C=CC=CC2=1 ACYHNAHLXFLGLX-UHFFFAOYSA-N 0.000 title abstract description 8
- 208000015114 central nervous system disease Diseases 0.000 title description 8
- 230000002265 prevention Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 24
- 239000012453 solvate Substances 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 239000002858 neurotransmitter agent Substances 0.000 claims abstract description 16
- 230000000035 biogenic effect Effects 0.000 claims abstract description 13
- 230000001722 neurochemical effect Effects 0.000 claims abstract description 11
- 230000006378 damage Effects 0.000 claims abstract description 10
- 230000006806 disease prevention Effects 0.000 claims abstract description 8
- -1 nitro, hydroxy Chemical group 0.000 claims description 37
- 102000005962 receptors Human genes 0.000 claims description 34
- 108020003175 receptors Proteins 0.000 claims description 34
- 208000035475 disorder Diseases 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 230000027455 binding Effects 0.000 claims description 25
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
- 229960002748 norepinephrine Drugs 0.000 claims description 9
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 9
- 229940076279 serotonin Drugs 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 7
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 208000037765 diseases and disorders Diseases 0.000 claims description 6
- 229960003638 dopamine Drugs 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000009103 reabsorption Effects 0.000 claims description 5
- SETTYMUWWAYTON-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(COCCN(C)C)=N2 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(COCCN(C)C)=N2 SETTYMUWWAYTON-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 208000022821 personality disease Diseases 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 3
- WGBOAEZQOQTZHZ-UHFFFAOYSA-N 2-[(17-chloro-3-oxa-13-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(14),2(6),4,7,9,11,15,17-octaen-4-yl)methoxy]-N,N-dimethylethanamine Chemical compound C12=CC(Cl)=CC=C2SC2=CC=CC=C2C2=C1OC(COCCN(C)C)=N2 WGBOAEZQOQTZHZ-UHFFFAOYSA-N 0.000 claims description 3
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims description 3
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims description 3
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 3
- 101150104779 HTR2A gene Proteins 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- IUAXYZNACGSNPT-UHFFFAOYSA-N 1-oxa-8-thia-3-aza-dibenzo[e,h]azulene Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC=N2 IUAXYZNACGSNPT-UHFFFAOYSA-N 0.000 claims description 2
- XKVAYBPYSJSTDX-UHFFFAOYSA-N 2-[(17-chloro-3,13-dioxa-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(14),2(6),4,7,9,11,15,17-octaen-4-yl)methoxy]-N,N-dimethylethanamine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(COCCN(C)C)=N2 XKVAYBPYSJSTDX-UHFFFAOYSA-N 0.000 claims description 2
- PHLUBDZVEJGYJB-UHFFFAOYSA-N 3-(3,13-dioxa-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-yl)propanoic acid Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(CCC(=O)O)=N2 PHLUBDZVEJGYJB-UHFFFAOYSA-N 0.000 claims description 2
- JLOGGCNGOZFQJM-UHFFFAOYSA-N 9-chloro-4-methyl-3,13-dioxa-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1OC(C)=N2 JLOGGCNGOZFQJM-UHFFFAOYSA-N 0.000 claims description 2
- OEXDCARIKUIQEC-UHFFFAOYSA-N 9-chloro-4-methyl-3-oxa-13-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound C12=CC=CC=C2SC2=CC=C(Cl)C=C2C2=C1OC(C)=N2 OEXDCARIKUIQEC-UHFFFAOYSA-N 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims description 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 2
- CNQYYXWFMOOBPO-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1OC(COCCN(C)C)=N2 Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1OC(COCCN(C)C)=N2 CNQYYXWFMOOBPO-UHFFFAOYSA-N 0.000 claims description 2
- MODZTTFITAUAJC-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(CBr)=N2 Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(CBr)=N2 MODZTTFITAUAJC-UHFFFAOYSA-N 0.000 claims description 2
- YEIMCEIPWDWMLK-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(CCCO)=N2 Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(CCCO)=N2 YEIMCEIPWDWMLK-UHFFFAOYSA-N 0.000 claims description 2
- ZYHMYGYLOUEQKL-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC=N2 Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC=N2 ZYHMYGYLOUEQKL-UHFFFAOYSA-N 0.000 claims description 2
- XUPVCRSJZKNVFF-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(C=O)=N2 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(C=O)=N2 XUPVCRSJZKNVFF-UHFFFAOYSA-N 0.000 claims description 2
- PJJQCUKQSQVIIT-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(CCC(=O)O)=N2 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(CCC(=O)O)=N2 PJJQCUKQSQVIIT-UHFFFAOYSA-N 0.000 claims description 2
- HLLNNUWAYSRDOE-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(CCC(=O)OCC)=N2 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(CCC(=O)OCC)=N2 HLLNNUWAYSRDOE-UHFFFAOYSA-N 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 101150013372 Htr2c gene Proteins 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010061216 Infarction Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000027626 Neurocognitive disease Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
- 206010033664 Panic attack Diseases 0.000 claims description 2
- 206010041235 Snoring Diseases 0.000 claims description 2
- 206010041250 Social phobia Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 230000016571 aggressive behavior Effects 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
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- 210000004556 brain Anatomy 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
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- 150000003573 thiols Chemical class 0.000 claims 5
- CLAFGTRNOXHFEL-UHFFFAOYSA-N 2-(3,13-dioxa-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-ylmethoxy)-N,N-dimethylethanamine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(COCCN(C)C)=N2 CLAFGTRNOXHFEL-UHFFFAOYSA-N 0.000 claims 1
- IGPIGGHOCPHBLE-UHFFFAOYSA-N 3-(3-oxa-13-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-yl)propan-1-ol Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(CCCO)=N2 IGPIGGHOCPHBLE-UHFFFAOYSA-N 0.000 claims 1
- ZKWXTBXIOPZEHK-UHFFFAOYSA-N 3-[(9-chloro-3,13-dioxa-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaen-4-yl)methoxy]-N,N-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1OC(COCCCN(C)C)=N2 ZKWXTBXIOPZEHK-UHFFFAOYSA-N 0.000 claims 1
- IHWOKTCLDSJZFB-UHFFFAOYSA-N 3-[(9-chloro-3-oxa-13-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaen-4-yl)methoxy]-N,N-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2SC2=CC=C(Cl)C=C2C2=C1OC(COCCCN(C)C)=N2 IHWOKTCLDSJZFB-UHFFFAOYSA-N 0.000 claims 1
- OHPVIIKNYXRPSE-UHFFFAOYSA-N 3-oxa-13-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-ylmethanol Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(CO)=N2 OHPVIIKNYXRPSE-UHFFFAOYSA-N 0.000 claims 1
- HKJQMJHSWRBHPX-UHFFFAOYSA-N 4-(bromomethyl)-17-chloro-3,13-dioxa-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(14),2(6),4,7,9,11,15,17-octaene Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(CBr)=N2 HKJQMJHSWRBHPX-UHFFFAOYSA-N 0.000 claims 1
- SSIMPBZEYDOGLE-UHFFFAOYSA-N 4-methyl-3-oxa-13-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaene Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1OC(C)=N2 SSIMPBZEYDOGLE-UHFFFAOYSA-N 0.000 claims 1
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- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Endocrinology (AREA)
- Anesthesiology (AREA)
- Reproductive Health (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20030959A HRP20030959A2 (en, 2012) | 2003-11-21 | 2003-11-21 | |
| HRP20030959A | 2003-11-21 | ||
| PCT/HR2004/000054 WO2005049036A1 (en) | 2003-11-21 | 2004-11-19 | USE OF 3-AZA-1-OXA-DIBENZO [e,h] AZULENES FOR THE MANUFACTURE OF PHARMACEUTICAL FORMULATIONS FOR THE TREATMENT AND PREVENTION OF CENTRAL NERVOUS SYSTEM DISEAS AND DISORDERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2546591A1 true CA2546591A1 (en) | 2005-06-02 |
Family
ID=34611163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002546591A Abandoned CA2546591A1 (en) | 2003-11-21 | 2004-11-19 | Use of 3-aza-1-oxa-dibenzo [e,h] azulenes for the manufacture of pharmaceutical formulations for the treatment and prevention of central nervous system diseases and disorders |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20070111990A1 (en, 2012) |
| EP (1) | EP1684766B1 (en, 2012) |
| JP (1) | JP2007512308A (en, 2012) |
| CN (1) | CN1901918A (en, 2012) |
| AT (1) | ATE365556T1 (en, 2012) |
| CA (1) | CA2546591A1 (en, 2012) |
| DE (1) | DE602004007289T2 (en, 2012) |
| ES (1) | ES2289573T3 (en, 2012) |
| HR (1) | HRP20030959A2 (en, 2012) |
| WO (1) | WO2005049036A1 (en, 2012) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3711489A (en) * | 1971-03-31 | 1973-01-16 | Pfizer | Certain 8,9-dihydro(3,4,7,8)cycloocta(1,2-d)imidazoles |
| NL7605526A (nl) * | 1976-05-24 | 1977-11-28 | Akzo Nv | Nieuwe tetracyclische derivaten. |
| US4198421A (en) * | 1978-11-30 | 1980-04-15 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2-substituted-dibenzo[2,3:6,7]oxepino[4,5-d]imidazoles |
| FR2504140A1 (fr) * | 1981-04-16 | 1982-10-22 | Centre Nat Rech Scient | Nouveaux derives tetracycliques de la dibenzazepine, leur procede de preparation et les compositions pharmaceutiques en renfermant |
| US4666716A (en) * | 1984-09-04 | 1987-05-19 | Richardson-Vicks Inc. | Antidiarrheal compositions and use thereof |
| DK0510068T3 (da) * | 1990-01-11 | 1999-10-25 | Upjohn Co | Nye 6,7,8,9-tetrahydro-3H-benz(e)indol-heterocycler med virkning på centralnervesystemet |
| UA52778C2 (uk) * | 1997-10-10 | 2003-01-15 | Янссен Фармацевтика Н.В. | Галогенозаміщені тетрациклічні похідні тетрагідрофурану, спосіб їх отримання та композиція на їх основі |
| US6015557A (en) * | 1999-02-24 | 2000-01-18 | Tobinick; Edward L. | Tumor necrosis factor antagonists for the treatment of neurological disorders |
| HRP20020304B1 (en) * | 2002-04-10 | 2008-04-30 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | 1-oxa-3-aza-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the production thereof |
-
2003
- 2003-11-21 HR HR20030959A patent/HRP20030959A2/xx not_active Application Discontinuation
-
2004
- 2004-11-19 WO PCT/HR2004/000054 patent/WO2005049036A1/en active IP Right Grant
- 2004-11-19 US US10/595,938 patent/US20070111990A1/en not_active Abandoned
- 2004-11-19 CA CA002546591A patent/CA2546591A1/en not_active Abandoned
- 2004-11-19 CN CNA2004800394544A patent/CN1901918A/zh active Pending
- 2004-11-19 ES ES04798733T patent/ES2289573T3/es not_active Expired - Lifetime
- 2004-11-19 EP EP04798733A patent/EP1684766B1/en not_active Expired - Lifetime
- 2004-11-19 AT AT04798733T patent/ATE365556T1/de not_active IP Right Cessation
- 2004-11-19 JP JP2006540631A patent/JP2007512308A/ja active Pending
- 2004-11-19 DE DE602004007289T patent/DE602004007289T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004007289T2 (de) | 2008-03-06 |
| HRP20030959A2 (en, 2012) | 2005-10-31 |
| WO2005049036A1 (en) | 2005-06-02 |
| ES2289573T3 (es) | 2008-02-01 |
| DE602004007289D1 (de) | 2007-08-09 |
| JP2007512308A (ja) | 2007-05-17 |
| EP1684766A1 (en) | 2006-08-02 |
| EP1684766B1 (en) | 2007-06-27 |
| ATE365556T1 (de) | 2007-07-15 |
| US20070111990A1 (en) | 2007-05-17 |
| HK1098670A1 (en) | 2007-07-27 |
| CN1901918A (zh) | 2007-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |