CA2468010A1 - Benzazepine derivatives and their use as 5-ht ligands - Google Patents
Benzazepine derivatives and their use as 5-ht ligands Download PDFInfo
- Publication number
- CA2468010A1 CA2468010A1 CA002468010A CA2468010A CA2468010A1 CA 2468010 A1 CA2468010 A1 CA 2468010A1 CA 002468010 A CA002468010 A CA 002468010A CA 2468010 A CA2468010 A CA 2468010A CA 2468010 A1 CA2468010 A1 CA 2468010A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- tetrahydro
- benzazepine
- heteroaryl
- heterocycle
- 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
- 239000003446 ligand Substances 0.000 title description 6
- 150000008038 benzoazepines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- -1 piperazino, pyrrolidino, piperidino, morpholino Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 33
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical group C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 21
- 241000124008 Mammalia Species 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 11
- 210000003169 central nervous system Anatomy 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000003745 diagnosis Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- CVNOETPEJAQFJJ-UHFFFAOYSA-N 7-(2,5-dimethylpyrrol-1-yl)-n-[6-(2-methylpyridin-3-yl)oxypyridin-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound CC1=CC=C(C)N1C1=CC=C(CCN(CC2)C(=O)NC=3C=NC(OC=4C(=NC=CC=4)C)=CC=3)C2=C1 CVNOETPEJAQFJJ-UHFFFAOYSA-N 0.000 claims description 3
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- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- JTPPOWSXYXUMSY-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound ClC1=NC=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 JTPPOWSXYXUMSY-UHFFFAOYSA-N 0.000 claims description 3
- DADLXCCWSHYYIK-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=NC(Cl)=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 DADLXCCWSHYYIK-UHFFFAOYSA-N 0.000 claims description 3
- CKFLMEWMMCJTCV-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 CKFLMEWMMCJTCV-UHFFFAOYSA-N 0.000 claims description 3
- AIESVUFSIFALRX-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CC2=CC=CC=C2CCN1C(=O)N[C@@H]1C(CC2)CCN2C1 AIESVUFSIFALRX-KRWDZBQOSA-N 0.000 claims description 3
- AIESVUFSIFALRX-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CC2=CC=CC=C2CCN1C(=O)N[C@H]1C(CC2)CCN2C1 AIESVUFSIFALRX-QGZVFWFLSA-N 0.000 claims description 3
- XPXYUVIUHGNRCC-UHFFFAOYSA-N n-[6-(2,4-dichlorophenoxy)pyridin-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1OC(N=C1)=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 XPXYUVIUHGNRCC-UHFFFAOYSA-N 0.000 claims description 3
- MGIIYGLPOOOIHQ-UHFFFAOYSA-N n-[6-(2-fluorophenoxy)pyridin-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound FC1=CC=CC=C1OC(N=C1)=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 MGIIYGLPOOOIHQ-UHFFFAOYSA-N 0.000 claims description 3
- VTNKLPACAVMLOW-UHFFFAOYSA-N n-[6-(2-propan-2-yloxyphenoxy)pyridin-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound CC(C)OC1=CC=CC=C1OC(N=C1)=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 VTNKLPACAVMLOW-UHFFFAOYSA-N 0.000 claims description 3
- FCWDZCGGDFWTLX-UHFFFAOYSA-N n-[6-(4-chloro-3,5-dimethylphenoxy)pyridin-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound CC1=C(Cl)C(C)=CC(OC=2N=CC(NC(=O)N3CCC4=CC=CC=C4CC3)=CC=2)=C1 FCWDZCGGDFWTLX-UHFFFAOYSA-N 0.000 claims description 3
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- UDIAJTAJODNTHO-UHFFFAOYSA-N n-[6-(4-chlorophenoxy)pyridin-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1OC(N=C1)=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 UDIAJTAJODNTHO-UHFFFAOYSA-N 0.000 claims description 3
- OMRMKCRSFXDCHD-UHFFFAOYSA-N n-[6-(4-methoxyphenoxy)pyridin-3-yl]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1OC(N=C1)=CC=C1NC(=O)N1CCC2=CC=CC=C2CC1 OMRMKCRSFXDCHD-UHFFFAOYSA-N 0.000 claims description 3
- WXMCHJDHHAHRIC-UHFFFAOYSA-N n-piperidin-3-yl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CC2=CC=CC=C2CCN1C(=O)NC1CCCNC1 WXMCHJDHHAHRIC-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000022610 schizoaffective disease Diseases 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 208000020685 sleep-wake disease Diseases 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 208000022170 stress incontinence Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BKDLGMUIXWPYGD-UHFFFAOYSA-N tert-butyllithium Chemical compound [Li]C(C)(C)C BKDLGMUIXWPYGD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 208000016686 tic disease Diseases 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
- 238000011200 topical administration Methods 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0468—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K51/047—Benzodiazepines
-
- 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
- A61P25/22—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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Psychiatry (AREA)
- Optics & Photonics (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33401201P | 2001-11-28 | 2001-11-28 | |
| US60/334,012 | 2001-11-28 | ||
| PCT/US2002/037715 WO2003045940A2 (en) | 2001-11-28 | 2002-11-26 | Benzazepine derivatives and their use as 5-ht ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2468010A1 true CA2468010A1 (en) | 2003-06-05 |
Family
ID=23305178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002468010A Abandoned CA2468010A1 (en) | 2001-11-28 | 2002-11-26 | Benzazepine derivatives and their use as 5-ht ligands |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6861420B2 (enExample) |
| EP (1) | EP1451176A2 (enExample) |
| JP (1) | JP2005535560A (enExample) |
| AU (1) | AU2002346507A1 (enExample) |
| BR (1) | BR0214529A (enExample) |
| CA (1) | CA2468010A1 (enExample) |
| MX (1) | MXPA04005151A (enExample) |
| WO (1) | WO2003045940A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003076426A2 (en) * | 2002-03-04 | 2003-09-18 | Pharmacia & Upjohn Company | Pyridinyloxy derivatives as 5-ht receptor ligands |
| TW200510324A (en) * | 2003-08-11 | 2005-03-16 | Lilly Co Eli | 6-(2,2,2-trifluoroethylamino)-7-chiloro-2, 3, 4, 5-tetrahydro-1h-benzo[d]azepine as a 5-ht2c receptor agonist |
| EP2479168B1 (en) | 2004-02-25 | 2014-04-09 | Eli Lilly And Company | 6-Substituted 2,3,4,5-Tetrahydro-1H-Benzo [d]Azepines as 5-HT2C Receptor Agonists |
| EP1728520A1 (de) * | 2005-05-04 | 2006-12-06 | Charité - Universitätsmedizin Berlin | Verwendung von spezifisch an das Serotonin-Transport-Protein (SERT) bindenden Radiopharmaka zur Herstellung eines Diagnostikums zur Untersuchung von Kopfschmerzerkrankungen |
| WO2006117218A2 (en) * | 2005-05-04 | 2006-11-09 | Charite Universitätsmedizin - Berlin | Serotonin-transport-protein binding radiopharmaceutical for the production of a diagnostic medicament for the diagnosis of headache |
| PT1924560E (pt) * | 2005-09-01 | 2009-10-23 | Lilly Co Eli | 2,3,4,5-tetra-hidro-1h-benzo[d]azepinas como agonistas de receptores 5-ht2c |
| ES2397400T3 (es) | 2005-09-01 | 2013-03-06 | Eli Lilly & Company | 6-arilalquilamino-2,3,4,5-tetrahidro-1H-benzo[D]azepinas como agonistas del receptor 5-HT2C |
| WO2007028132A2 (en) | 2005-09-01 | 2007-03-08 | Eli Lilly And Company | 6-N-LINKED HETEROCYCLE-SUBSTITUTED 2,3,4,5-TETRAHYDRO-1H-BENZO[d]AZEPINES AS 5-HT2C RECEPTOR AGONISTS |
| BRPI0615033A2 (pt) | 2005-09-01 | 2011-04-26 | Lilly Co Eli | composto, composição farmacêutica, e, uso de um composto |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5132311A (en) * | 1990-06-27 | 1992-07-21 | G. D. Searle & Co. | Cyanoquanidine type III antiarrhythmic agents and use |
| GB9612883D0 (en) | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
| GB9612885D0 (en) | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
| AU2001264376A1 (en) * | 2000-06-15 | 2001-12-24 | Chaconne Nsi Co., Ltd. | Urea derivative useful as an anti-cancer agent and process for preparing same |
-
2002
- 2002-11-26 CA CA002468010A patent/CA2468010A1/en not_active Abandoned
- 2002-11-26 MX MXPA04005151A patent/MXPA04005151A/es unknown
- 2002-11-26 BR BRPI0214529-4A patent/BR0214529A/pt not_active IP Right Cessation
- 2002-11-26 EP EP02784572A patent/EP1451176A2/en not_active Withdrawn
- 2002-11-26 US US10/305,408 patent/US6861420B2/en not_active Expired - Fee Related
- 2002-11-26 JP JP2003547390A patent/JP2005535560A/ja not_active Withdrawn
- 2002-11-26 WO PCT/US2002/037715 patent/WO2003045940A2/en not_active Ceased
- 2002-11-26 AU AU2002346507A patent/AU2002346507A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6861420B2 (en) | 2005-03-01 |
| US20030149024A1 (en) | 2003-08-07 |
| WO2003045940A3 (en) | 2003-09-12 |
| MXPA04005151A (es) | 2004-08-11 |
| BR0214529A (pt) | 2006-05-30 |
| JP2005535560A (ja) | 2005-11-24 |
| EP1451176A2 (en) | 2004-09-01 |
| WO2003045940A2 (en) | 2003-06-05 |
| AU2002346507A8 (en) | 2003-06-10 |
| AU2002346507A1 (en) | 2003-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |