NO174507B - Analogifremgangsmaate for fremstilling av terapeutisk aktive substiuerte benzazepiner - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive substiuerte benzazepiner Download PDFInfo
- Publication number
- NO174507B NO174507B NO885096A NO885096A NO174507B NO 174507 B NO174507 B NO 174507B NO 885096 A NO885096 A NO 885096A NO 885096 A NO885096 A NO 885096A NO 174507 B NO174507 B NO 174507B
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- Norway
- Prior art keywords
- methyl
- chloro
- tetrahydro
- formula
- compound
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- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 150000008038 benzoazepines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- -1 1-substituted-2,3,4,5-tetrahydro-1H-3-benzazepines Chemical class 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 89
- 239000000460 chlorine Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- 230000009467 reduction Effects 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000002785 azepinyl group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 230000026030 halogenation Effects 0.000 claims description 3
- 238000005658 halogenation reaction Methods 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- FKWYOTLPGSGDTP-UHFFFAOYSA-N 8-chloro-3-methyl-5-(2,2,2-trifluoroethoxy)-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound FC(F)(F)COC1CN(C)CCC2=CC(Cl)=C(O)C=C21 FKWYOTLPGSGDTP-UHFFFAOYSA-N 0.000 claims description 2
- XVCTVHVYHVASIP-UHFFFAOYSA-N 8-chloro-3-methyl-5-(2-phenylethoxy)-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1OCCC1=CC=CC=C1 XVCTVHVYHVASIP-UHFFFAOYSA-N 0.000 claims description 2
- QIRXFZBPQOTDCU-UHFFFAOYSA-N 8-chloro-3-methyl-5-phenoxy-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1OC1=CC=CC=C1 QIRXFZBPQOTDCU-UHFFFAOYSA-N 0.000 claims description 2
- BWUDJJGJDCRQNH-UHFFFAOYSA-N 8-chloro-3-methyl-5-phenylmethoxy-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1OCC1=CC=CC=C1 BWUDJJGJDCRQNH-UHFFFAOYSA-N 0.000 claims description 2
- GYHGYVBXMMJZRX-UHFFFAOYSA-N 8-chloro-3-methyl-5-phenylsulfanyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1SC1=CC=CC=C1 GYHGYVBXMMJZRX-UHFFFAOYSA-N 0.000 claims description 2
- KMGQNUYJWJFJQG-UHFFFAOYSA-N 8-chloro-3-methyl-5-piperidin-1-yl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1N1CCCCC1 KMGQNUYJWJFJQG-UHFFFAOYSA-N 0.000 claims description 2
- XINWVWPVSCGKJU-UHFFFAOYSA-N 8-chloro-3-methyl-5-pyrrol-1-yl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1N1C=CC=C1 XINWVWPVSCGKJU-UHFFFAOYSA-N 0.000 claims description 2
- YWMDBNUBAGRKLQ-UHFFFAOYSA-N 8-chloro-5-cyclohex-2-en-1-yl-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1C1CCCC=C1 YWMDBNUBAGRKLQ-UHFFFAOYSA-N 0.000 claims description 2
- LTQIAJAFDWMJTE-UHFFFAOYSA-N 8-chloro-5-cyclohexyl-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1C1CCCCC1 LTQIAJAFDWMJTE-UHFFFAOYSA-N 0.000 claims description 2
- QTRSQVRJSMUFNF-UHFFFAOYSA-N 8-chloro-5-cyclohexyloxy-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1OC1CCCCC1 QTRSQVRJSMUFNF-UHFFFAOYSA-N 0.000 claims description 2
- UWJZELKDZCMKAN-UHFFFAOYSA-N 8-chloro-5-ethoxy-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound CCOC1CN(C)CCC2=CC(Cl)=C(O)C=C12 UWJZELKDZCMKAN-UHFFFAOYSA-N 0.000 claims description 2
- ZRNUCTXOLFRDOO-UHFFFAOYSA-N 8-chloro-5-ethoxy-n,n,5-trimethyl-1,2,3,4-tetrahydro-3-benzazepine-7-carboxamide Chemical compound CCOC1(C)CNCCC2=CC(Cl)=C(C(=O)N(C)C)C=C12 ZRNUCTXOLFRDOO-UHFFFAOYSA-N 0.000 claims description 2
- VVFBHNJTTAXEPI-UHFFFAOYSA-N 8-chloro-5-ethylsulfanyl-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound CCSC1CN(C)CCC2=CC(Cl)=C(O)C=C12 VVFBHNJTTAXEPI-UHFFFAOYSA-N 0.000 claims description 2
- MPKFCNPYESGCCE-UHFFFAOYSA-N 8-chloro-5-methoxy-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound COC1CN(C)CCC2=CC(Cl)=C(O)C=C12 MPKFCNPYESGCCE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- SUACDOBINQPHIA-UHFFFAOYSA-N [8-chloro-3-methyl-5-(3-methylbut-2-enyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl] acetate Chemical compound CC(C)=CCC1CN(C)CCC2=CC(Cl)=C(OC(C)=O)C=C21 SUACDOBINQPHIA-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 230000020335 dealkylation Effects 0.000 claims description 2
- 238000006900 dealkylation reaction Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 238000007031 hydroxymethylation reaction Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- RRHPQRCPGVDEPK-UHFFFAOYSA-N (8-chloro-5-cyclohexyl-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl) ethyl carbonate Chemical compound C1N(C)CCC=2C=C(Cl)C(OC(=O)OCC)=CC=2C1C1CCCCC1 RRHPQRCPGVDEPK-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 208000028017 Psychotic disease Diseases 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 230000036407 pain Effects 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
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- 239000000243 solution Substances 0.000 description 58
- 239000000203 mixture Substances 0.000 description 57
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- VIANBEAUACIOKY-UHFFFAOYSA-M sodium;3-ethoxy-3-oxopropanoate Chemical compound [Na+].CCOC(=O)CC([O-])=O VIANBEAUACIOKY-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/24—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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/32—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3213587A | 1987-03-27 | 1987-03-27 | |
| PCT/US1988/000899 WO1988007526A1 (en) | 1987-03-27 | 1988-03-24 | Substituted benzazepines, their preparation and pharmaceutical compositions containing them |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO885096D0 NO885096D0 (no) | 1988-11-15 |
| NO885096L NO885096L (no) | 1988-11-15 |
| NO174507B true NO174507B (no) | 1994-02-07 |
| NO174507C NO174507C (de) | 1994-05-18 |
Family
ID=21863286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO885096A NO174507B (no) | 1987-03-27 | 1988-11-15 | Analogifremgangsmaate for fremstilling av terapeutisk aktive substiuerte benzazepiner |
Country Status (18)
| Country | Link |
|---|---|
| EP (2) | EP0285919B1 (de) |
| JP (1) | JPH0662574B2 (de) |
| KR (1) | KR930011489B1 (de) |
| AT (1) | ATE112766T1 (de) |
| AU (1) | AU619744B2 (de) |
| CA (1) | CA1321195C (de) |
| DE (1) | DE3851769T2 (de) |
| DK (1) | DK165688C (de) |
| FI (1) | FI894566A (de) |
| HU (1) | HU205744B (de) |
| IL (1) | IL85855A (de) |
| MY (1) | MY103357A (de) |
| NO (1) | NO174507B (de) |
| NZ (1) | NZ224038A (de) |
| PH (1) | PH27337A (de) |
| PT (1) | PT87068B (de) |
| WO (1) | WO1988007526A1 (de) |
| ZA (1) | ZA882080B (de) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK107688D0 (da) * | 1988-03-01 | 1988-03-01 | Novo Industri As | Carbaminsyreestere af substituerede 7-hydroxy-2,3,4,5-tetrahydro-1h-3-benzazepiner |
| DK67489D0 (da) * | 1989-02-14 | 1989-02-14 | Novo Industri As | Nye benzazepinderivater |
| US5068326A (en) * | 1989-04-03 | 1991-11-26 | Kung Hank F | Dopamine receptor ligands and imaging agents |
| AU8201591A (en) * | 1990-06-15 | 1992-01-07 | Schering Corporation | 8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substitued benzazepines and pharmaceutical compositions containing them |
| US5374722A (en) * | 1990-09-25 | 1994-12-20 | Schering Corporation | Bridged benzazepines |
| US5241065A (en) * | 1992-02-25 | 1993-08-31 | Schering Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepines having anti-psychotic activity |
| IL153710A0 (en) * | 2000-07-05 | 2003-07-06 | Ortho Mcneil Pharm Inc | Nonpeptide substituted spirobenzoazepines as vasopressin antagonists |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| ATE441417T1 (de) * | 2002-12-20 | 2009-09-15 | Glaxo Group Ltd | Benzoädüazepinderivate für die behandlung von neurologischen krankheiten |
| US7504391B2 (en) | 2003-05-22 | 2009-03-17 | Schering Corporation | Selective D1/D5 receptor antagonists for the treatment of obesity and CNS disorders |
| MXPA05013364A (es) | 2003-06-17 | 2006-03-17 | Arena Pharm Inc | Procedimiento para preparar 3-benzazepinas. |
| AU2012200805B2 (en) * | 2003-06-17 | 2015-01-22 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives useful for the treatment of 5HT2C receptor associated diseases |
| CN101792417A (zh) | 2003-06-17 | 2010-08-04 | 艾尼纳制药公司 | 用于治疗5ht2c受体相关疾病的苯并氮杂卓衍生物 |
| WO2005042491A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| WO2005042490A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| SI1838677T1 (sl) | 2004-12-21 | 2010-01-29 | Arena Pharm Inc | Kristalne oblike (R)-8-kloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzazepin hidroklorida |
| EA015012B1 (ru) | 2004-12-23 | 2011-04-29 | Арена Фармасьютикалз, Инк. | Композиция, содержащая фентермин и избирательный агонист рецептора 5ht, и ее применение |
| SG10201508066VA (en) | 2006-04-03 | 2015-10-29 | Arena Pharm Inc | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
| ES2522587T3 (es) | 2006-12-05 | 2014-11-17 | Arena Pharmaceuticals, Inc. | Procesos para preparar (R)-8-cloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzacepina e intermedios de la misma |
| WO2009111004A1 (en) | 2008-03-04 | 2009-09-11 | Arena Pharmaceuticals, Inc. | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
| EP2443080A2 (de) | 2009-06-18 | 2012-04-25 | Arena Pharmaceuticals, Inc. | Verfahren zur herstellung von 5-ht2c-rezeptoragonisten |
| WO2011153206A1 (en) | 2010-06-02 | 2011-12-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| EP2611782A1 (de) | 2010-09-01 | 2013-07-10 | Arena Pharmaceuticals, Inc. | Lorcaserin-salze mit optisch aktiven säuren |
| EP2611433A2 (de) | 2010-09-01 | 2013-07-10 | Arena Pharmaceuticals, Inc. | Nicht-hygroskopische salze aus 5-ht2c-agonisten |
| KR20180118801A (ko) | 2010-09-01 | 2018-10-31 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 체중 관리에 유용한 5-ｈｔ2ｃ 작동제의 변형-방출 투여 형태 |
| SG188365A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Administration of lorcaserin to individuals with renal impairment |
| KR20190128001A (ko) | 2012-10-09 | 2019-11-13 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 체중 관리 방법 |
| HU230826B1 (hu) | 2014-11-19 | 2018-07-30 | Richter Gedeon Nyrt. | Eljárás benzazepin származékok előállítására |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA974989A (en) * | 1968-03-11 | 1975-09-23 | Wallace And Tiernan Inc. | Process for preparing 1,2,4,5-tetrahydro-3h,3-benzazepines and products obtained thereby |
| DE1934150A1 (de) * | 1968-07-10 | 1970-01-15 | Pennwalt Corp | Neue 1-Alkanoyloxy-1,2,4,5-tetrahydro-3H,3-benzazepine |
| US4988690A (en) * | 1982-06-14 | 1991-01-29 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines and anti-depressant use thereof |
| DK180485D0 (da) * | 1985-04-22 | 1985-04-23 | Novo Industri As | Nitrogenholdige forbindelser |
| US4707483A (en) * | 1985-12-20 | 1987-11-17 | Smithkline Beckman Corporation | 1-phenyl-3-benzazepines and their use for treating gastrointestinal motility disorders |
| GB8807922D0 (en) * | 1988-04-05 | 1988-05-05 | Fujisawa Pharmaceutical Co | Isoquinoline compound & process for preparation thereof |
-
1988
- 1988-03-23 ZA ZA882080A patent/ZA882080B/xx unknown
- 1988-03-23 PH PH36675A patent/PH27337A/en unknown
- 1988-03-24 DE DE3851769T patent/DE3851769T2/de not_active Expired - Fee Related
- 1988-03-24 PT PT87068A patent/PT87068B/pt not_active IP Right Cessation
- 1988-03-24 IL IL85855A patent/IL85855A/xx not_active IP Right Cessation
- 1988-03-24 EP EP88104758A patent/EP0285919B1/de not_active Expired - Lifetime
- 1988-03-24 EP EP88903596A patent/EP0357641A1/de active Pending
- 1988-03-24 MY MYPI88000305A patent/MY103357A/en unknown
- 1988-03-24 AT AT88104758T patent/ATE112766T1/de not_active IP Right Cessation
- 1988-03-24 CA CA000562352A patent/CA1321195C/en not_active Expired - Fee Related
- 1988-03-24 AU AU15964/88A patent/AU619744B2/en not_active Ceased
- 1988-03-24 WO PCT/US1988/000899 patent/WO1988007526A1/en not_active Application Discontinuation
- 1988-03-24 KR KR1019880701534A patent/KR930011489B1/ko not_active IP Right Cessation
- 1988-03-24 HU HU882812A patent/HU205744B/hu not_active IP Right Cessation
- 1988-03-24 JP JP63503399A patent/JPH0662574B2/ja not_active Expired - Lifetime
- 1988-03-25 NZ NZ224038A patent/NZ224038A/xx unknown
- 1988-11-15 NO NO885096A patent/NO174507B/no unknown
- 1988-11-23 DK DK652688A patent/DK165688C/da active
-
1989
- 1989-09-27 FI FI894566A patent/FI894566A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI894566A0 (fi) | 1989-09-27 |
| DK165688C (da) | 1993-05-24 |
| MY103357A (en) | 1993-06-30 |
| IL85855A (en) | 1993-02-21 |
| EP0285919A1 (de) | 1988-10-12 |
| KR890700577A (ko) | 1989-04-25 |
| AU1596488A (en) | 1988-11-02 |
| NO885096D0 (no) | 1988-11-15 |
| FI894566A (fi) | 1989-09-27 |
| EP0357641A1 (de) | 1990-03-14 |
| JPH0662574B2 (ja) | 1994-08-17 |
| PH27337A (en) | 1993-06-08 |
| DE3851769D1 (de) | 1994-11-17 |
| DK652688A (da) | 1988-11-23 |
| DK652688D0 (da) | 1988-11-23 |
| NZ224038A (en) | 1990-10-26 |
| NO174507C (de) | 1994-05-18 |
| PT87068B (pt) | 1992-07-31 |
| ATE112766T1 (de) | 1994-10-15 |
| HUT53882A (en) | 1990-12-28 |
| PT87068A (pt) | 1988-04-01 |
| DE3851769T2 (de) | 1995-03-09 |
| WO1988007526A1 (en) | 1988-10-06 |
| HU205744B (en) | 1992-06-29 |
| DK165688B (da) | 1993-01-04 |
| IL85855A0 (en) | 1988-09-30 |
| KR930011489B1 (ko) | 1993-12-08 |
| NO885096L (no) | 1988-11-15 |
| JPH02502723A (ja) | 1990-08-30 |
| AU619744B2 (en) | 1992-02-06 |
| EP0285919B1 (de) | 1994-10-12 |
| ZA882080B (en) | 1989-04-26 |
| CA1321195C (en) | 1993-08-10 |
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