IE912031A1 - 8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substituted¹benzazepines and pharmaceutical compositions containing them - Google Patents
8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substituted¹benzazepines and pharmaceutical compositions containing themInfo
- Publication number
- IE912031A1 IE912031A1 IE203191A IE203191A IE912031A1 IE 912031 A1 IE912031 A1 IE 912031A1 IE 203191 A IE203191 A IE 203191A IE 203191 A IE203191 A IE 203191A IE 912031 A1 IE912031 A1 IE 912031A1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- mammal
- dimethyl
- compounds
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 9
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 230000001430 anti-depressive effect Effects 0.000 claims description 7
- 230000036592 analgesia Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000000561 anti-psychotic effect Effects 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- MHMRQHMKGYLQKH-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepin-7-ol Chemical compound C1CNCCC2=CC(O)=CC=C21 MHMRQHMKGYLQKH-UHFFFAOYSA-N 0.000 claims 1
- GLFBQHNVIHPOMD-UHFFFAOYSA-N 5-cyclopentyl-3,8-dimethyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(C)=C(O)C=C2C1C1CCCC1 GLFBQHNVIHPOMD-UHFFFAOYSA-N 0.000 claims 1
- 230000036407 pain Effects 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- -1 5-substituted-2, 3, 4, 5-tetrahydro-1 H-3benzazepines Chemical class 0.000 description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
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- 239000000203 mixture Substances 0.000 description 36
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- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
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- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
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- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery 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
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- 238000005303 weighing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53896590A | 1990-06-15 | 1990-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE912031A1 true IE912031A1 (en) | 1991-12-18 |
Family
ID=24149189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE203191A IE912031A1 (en) | 1990-06-15 | 1991-06-14 | 8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substituted¹benzazepines and pharmaceutical compositions containing them |
Country Status (6)
| Country | Link |
|---|---|
| AU (1) | AU8201591A (pt) |
| IE (1) | IE912031A1 (pt) |
| IL (1) | IL98487A0 (pt) |
| PT (1) | PT97984A (pt) |
| WO (1) | WO1991019698A1 (pt) |
| ZA (1) | ZA914536B (pt) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5241065A (en) * | 1992-02-25 | 1993-08-31 | Schering Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepines having anti-psychotic activity |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| US7696193B2 (en) | 2002-12-20 | 2010-04-13 | Glaxo Group Limited | Benzazepine derivatives for the treatment of neurological disorders |
| EP1636191A2 (en) | 2003-06-17 | 2006-03-22 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives useful for the treatment of 5ht2c receptor associated diseases |
| CN1805938B (zh) | 2003-06-17 | 2010-06-16 | 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 |
| US20080009478A1 (en) * | 2003-10-22 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases |
| NZ555981A (en) | 2004-12-21 | 2011-01-28 | Arena Pharm Inc | Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| EP1833473B1 (en) | 2004-12-23 | 2009-09-09 | Arena Pharmaceuticals, Inc. | 5ht2c receptor modulator compositions and methods of use |
| CA2646044A1 (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 |
| 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 |
| CN102648170A (zh) | 2009-06-18 | 2012-08-22 | 艾尼纳制药公司 | 制备5-ht2c受体激动剂的方法 |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| MX2013002418A (es) | 2010-09-01 | 2013-08-01 | Arena Pharm Inc | Administracion de lorcaserina a individuos con daño renal. |
| SG188361A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Non-hygroscopic salts of 5-ht2c agonists |
| CN103189053A (zh) | 2010-09-01 | 2013-07-03 | 艾尼纳制药公司 | 用于体重控制的5-ht2c激动剂的调节释放剂型 |
| JP2013539470A (ja) | 2010-09-01 | 2013-10-24 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ロルカセリンと光学活性な酸との塩 |
| BR112015007779A2 (pt) | 2012-10-09 | 2017-07-04 | Arena Pharm Inc | célula de fluxo de permeabilidade e sistema de condutância hidráulica |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH27337A (en) * | 1987-03-27 | 1993-06-08 | Schering Corp | Substituted benzazepines their preparation and pharmaceutical compositions containing them |
-
1991
- 1991-06-13 AU AU82015/91A patent/AU8201591A/en not_active Abandoned
- 1991-06-13 IL IL98487A patent/IL98487A0/xx unknown
- 1991-06-13 ZA ZA914536A patent/ZA914536B/xx unknown
- 1991-06-13 WO PCT/US1991/004046 patent/WO1991019698A1/en unknown
- 1991-06-14 PT PT97984A patent/PT97984A/pt not_active Application Discontinuation
- 1991-06-14 IE IE203191A patent/IE912031A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA914536B (en) | 1992-03-25 |
| WO1991019698A1 (en) | 1991-12-26 |
| IL98487A0 (en) | 1992-07-15 |
| AU8201591A (en) | 1992-01-07 |
| PT97984A (pt) | 1992-03-31 |
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