IE55404B1 - 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines,a process for preparing the same and their use as medicaments - Google Patents
1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines,a process for preparing the same and their use as medicamentsInfo
- Publication number
- IE55404B1 IE55404B1 IE1384/83A IE138483A IE55404B1 IE 55404 B1 IE55404 B1 IE 55404B1 IE 1384/83 A IE1384/83 A IE 1384/83A IE 138483 A IE138483 A IE 138483A IE 55404 B1 IE55404 B1 IE 55404B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- benzazepine
- tetrahydro
- formula
- oil
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 107
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- -1 alkylene amine Chemical class 0.000 claims abstract description 24
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 19
- 150000004820 halides Chemical class 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- JHWVRHCUFLRKFZ-UHFFFAOYSA-N 2-[5-[4-(trifluoromethyl)phenoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanamine Chemical compound C1N(CCN)CCC2=CC=CC=C2C1OC1=CC=C(C(F)(F)F)C=C1 JHWVRHCUFLRKFZ-UHFFFAOYSA-N 0.000 claims description 3
- MAIIKQNCBVQRBM-UHFFFAOYSA-N 7,8-dimethoxy-5-phenoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNCC1OC1=CC=CC=C1 MAIIKQNCBVQRBM-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000007344 nucleophilic reaction Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- UXKLWPPBHFSCIU-UHFFFAOYSA-N 3-[5-[4-(trifluoromethyl)phenoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]propan-1-amine Chemical compound C1N(CCCN)CCC2=CC=CC=C2C1OC1=CC=C(C(F)(F)F)C=C1 UXKLWPPBHFSCIU-UHFFFAOYSA-N 0.000 claims 1
- ZMOPIHQDPJYYKW-UHFFFAOYSA-N 5-(3-chlorophenoxy)-7,8-dimethoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNCC1OC1=CC=CC(Cl)=C1 ZMOPIHQDPJYYKW-UHFFFAOYSA-N 0.000 claims 1
- VOIFXRDZAJDFPB-UHFFFAOYSA-N 5-(4-methoxyphenoxy)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=CC(OC)=CC=C1OC1C2=CC=CC=C2CCNC1 VOIFXRDZAJDFPB-UHFFFAOYSA-N 0.000 claims 1
- AOHFDDOIDVKIPT-UHFFFAOYSA-N 7,8-dimethoxy-3-methyl-5-[4-(trifluoromethyl)phenoxy]-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C)CC1OC1=CC=C(C(F)(F)F)C=C1 AOHFDDOIDVKIPT-UHFFFAOYSA-N 0.000 claims 1
- ZUGSPVVYXXJHCM-UHFFFAOYSA-N 7,8-dimethoxy-3-methyl-5-phenoxy-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C)CC1OC1=CC=CC=C1 ZUGSPVVYXXJHCM-UHFFFAOYSA-N 0.000 claims 1
- WNBKEEWOYWFAIT-UHFFFAOYSA-N 7,8-dimethoxy-5-(4-methoxyphenoxy)-3-methyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=CC(OC)=CC=C1OC1C2=CC(OC)=C(OC)C=C2CCN(C)C1 WNBKEEWOYWFAIT-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 description 164
- 239000000243 solution Substances 0.000 description 164
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 162
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 144
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 121
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- 239000000203 mixture Substances 0.000 description 75
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 63
- 238000004458 analytical method Methods 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 53
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 229940093499 ethyl acetate Drugs 0.000 description 39
- 235000019439 ethyl acetate Nutrition 0.000 description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- 239000000463 material Substances 0.000 description 34
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- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 239000000725 suspension Substances 0.000 description 30
- 238000003756 stirring Methods 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000000284 extract Substances 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 15
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 14
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 14
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 6
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- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 5
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- DLPAZJHBHBXCIR-UHFFFAOYSA-N 1-[5-[4-(trifluoromethyl)phenoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC2=CC=CC=C2C1OC1=CC=C(C(F)(F)F)C=C1 DLPAZJHBHBXCIR-UHFFFAOYSA-N 0.000 description 3
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- JAMNOLUZQIBPRL-UHFFFAOYSA-N n,n-dimethyl-2-[5-[4-(trifluoromethyl)phenoxy]-3-benzazepin-3-yl]ethanamine;dihydrochloride Chemical compound Cl.Cl.C=1N(CCN(C)C)C=CC2=CC=CC=C2C=1OC1=CC=C(C(F)(F)F)C=C1 JAMNOLUZQIBPRL-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- XIRRHVQGTNESAX-UHFFFAOYSA-N oxalic acid 2-[5-[3-(trifluoromethyl)phenoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanamine Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C1N(CCN)CCC2=CC=CC=C2C1OC1=CC=CC(C(F)(F)F)=C1 XIRRHVQGTNESAX-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 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
- 235000013874 shellac Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 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
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- A61P25/24—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
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/387,916 US4988690A (en) | 1982-06-14 | 1982-06-14 | 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines and anti-depressant use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE831384L IE831384L (en) | 1983-12-14 |
| IE55404B1 true IE55404B1 (en) | 1990-09-12 |
Family
ID=23531838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1384/83A IE55404B1 (en) | 1982-06-14 | 1983-06-13 | 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines,a process for preparing the same and their use as medicaments |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4988690A (enExample) |
| EP (1) | EP0096838B1 (enExample) |
| JP (1) | JPS595165A (enExample) |
| KR (1) | KR900001214B1 (enExample) |
| AT (1) | ATE26263T1 (enExample) |
| AU (1) | AU570920B2 (enExample) |
| CA (1) | CA1214460A (enExample) |
| DE (1) | DE3370621D1 (enExample) |
| DK (1) | DK270983A (enExample) |
| ES (1) | ES8503666A1 (enExample) |
| FI (1) | FI78473C (enExample) |
| GR (1) | GR78291B (enExample) |
| HU (1) | HU190902B (enExample) |
| IE (1) | IE55404B1 (enExample) |
| IL (1) | IL68964A (enExample) |
| PT (1) | PT76864B (enExample) |
| ZA (1) | ZA834309B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5015639A (en) * | 1987-03-27 | 1991-05-14 | Schering Corporation | Substituted benzazepines, their preparation and pharmaceutical compositions containing them |
| ZA882080B (en) * | 1987-03-27 | 1989-04-26 | Schering Corp | Substituted benzazepines,their preparation and pharmaceutical compositions containing them |
| CA1327795C (en) * | 1987-08-14 | 1994-03-15 | Jules Freedman | Antidepressants which are aryloxy inadanamines |
| US5202319A (en) * | 1991-09-23 | 1993-04-13 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 3-amino-2,3,4,5-tetrahydro-1-aryloxy-3-benzazepines |
| US5639482A (en) * | 1993-11-10 | 1997-06-17 | Crary; Ely J. | Composition for control and prevention of diabetic retinopathy |
| US7115766B2 (en) * | 2000-11-30 | 2006-10-03 | Indiana University Research & Technology Corp. | Nucleophilic approach for preparing radiolabeled imaging agents and associated compounds |
| US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| CA2529320C (en) * | 2003-06-17 | 2013-03-05 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives useful for the treatment of 5ht2c receptor associated diseases |
| MXPA05013364A (es) | 2003-06-17 | 2006-03-17 | Arena Pharm Inc | Procedimiento para preparar 3-benzazepinas. |
| US20070275949A1 (en) * | 2003-10-22 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2C Receptor Associated Diseases |
| US20080009478A1 (en) * | 2003-10-22 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases |
| ATE442359T1 (de) | 2004-12-21 | 2009-09-15 | Arena Pharm Inc | Kristalline formen von (r)-8-chlor-1-methyl-2,3,4,5-tetrahydro-1h-3-be zazepinhydrochlorid |
| SG158168A1 (en) | 2004-12-23 | 2010-01-29 | Arena Pharm Inc | 5ht2c receptor modulator compositions and methods of use |
| WO2007120517A2 (en) | 2006-04-03 | 2007-10-25 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
| CA2670285A1 (en) * | 2006-12-05 | 2008-06-12 | Arena Pharmaceuticals, Inc. | Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof |
| AU2008251558B2 (en) * | 2007-05-10 | 2012-12-20 | Albany Molecular Research, Inc. | Aryloxy-and heteroaryloxy-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| CN102015591B (zh) | 2008-03-04 | 2014-01-29 | 艾尼纳制药公司 | 制备与5-ht2c激动剂(r)-8-氯-1-甲基-2，3，4，5-四氢-1h-3-苯并氮杂卓相关的中间体的方法 |
| US8952197B2 (en) | 2009-06-18 | 2015-02-10 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| CA3050049A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| SG10201506896RA (en) | 2010-09-01 | 2015-10-29 | Arena Pharm Inc | Administration of lorcaserin to individuals with renal impairment |
| CA2808904A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-ht2c agonists |
| CA2808909A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Salts of lorcaserin with optically active acids |
| MX2015004532A (es) | 2012-10-09 | 2016-01-20 | Arena Pharm Inc | Metodo de control del peso. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5233687A (en) * | 1975-09-11 | 1977-03-14 | Shionogi & Co Ltd | Process for preparation of 1,5-dihydro-2h-1,4-benzodiazepine-2-on deri vatives |
| JPS5481290A (en) * | 1977-11-17 | 1979-06-28 | Smithkline Corp | Benzazepin compound |
-
1982
- 1982-06-14 US US06/387,916 patent/US4988690A/en not_active Expired - Fee Related
-
1983
- 1983-06-08 AT AT83105610T patent/ATE26263T1/de not_active IP Right Cessation
- 1983-06-08 DE DE8383105610T patent/DE3370621D1/de not_active Expired
- 1983-06-08 EP EP83105610A patent/EP0096838B1/en not_active Expired
- 1983-06-10 FI FI832092A patent/FI78473C/fi not_active IP Right Cessation
- 1983-06-11 KR KR1019830002597A patent/KR900001214B1/ko not_active Expired
- 1983-06-13 ZA ZA834309A patent/ZA834309B/xx unknown
- 1983-06-13 JP JP58104343A patent/JPS595165A/ja active Granted
- 1983-06-13 CA CA000430280A patent/CA1214460A/en not_active Expired
- 1983-06-13 IE IE1384/83A patent/IE55404B1/en unknown
- 1983-06-13 HU HU832096A patent/HU190902B/hu not_active IP Right Cessation
- 1983-06-13 IL IL68964A patent/IL68964A/xx unknown
- 1983-06-13 ES ES523191A patent/ES8503666A1/es not_active Expired
- 1983-06-13 DK DK270983A patent/DK270983A/da not_active Application Discontinuation
- 1983-06-13 GR GR71648A patent/GR78291B/el unknown
- 1983-06-14 AU AU15764/83A patent/AU570920B2/en not_active Ceased
- 1983-06-14 PT PT76864A patent/PT76864B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK270983A (da) | 1983-12-15 |
| AU1576483A (en) | 1983-12-22 |
| FI832092L (fi) | 1983-12-15 |
| FI78473B (fi) | 1989-04-28 |
| HU190902B (en) | 1986-12-28 |
| KR900001214B1 (ko) | 1990-02-28 |
| IE831384L (en) | 1983-12-14 |
| EP0096838B1 (en) | 1987-04-01 |
| ZA834309B (en) | 1984-03-28 |
| ATE26263T1 (de) | 1987-04-15 |
| IL68964A (en) | 1988-03-31 |
| PT76864B (en) | 1986-02-27 |
| US4988690A (en) | 1991-01-29 |
| EP0096838A1 (en) | 1983-12-28 |
| GR78291B (enExample) | 1984-09-26 |
| DE3370621D1 (en) | 1987-05-07 |
| KR840005103A (ko) | 1984-11-03 |
| ES523191A0 (es) | 1985-03-01 |
| ES8503666A1 (es) | 1985-03-01 |
| JPS595165A (ja) | 1984-01-12 |
| CA1214460A (en) | 1986-11-25 |
| PT76864A (en) | 1983-07-01 |
| IL68964A0 (en) | 1983-10-31 |
| FI832092A0 (fi) | 1983-06-10 |
| JPH0365342B2 (enExample) | 1991-10-11 |
| FI78473C (fi) | 1989-08-10 |
| DK270983D0 (da) | 1983-06-13 |
| AU570920B2 (en) | 1988-03-31 |
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