CS213381B2 - Method of making the derivatives of 2,3,4,5-tetrahydro-1h-3-benzapines having in position 6 the substituted mercapto group - Google Patents

Method of making the derivatives of 2,3,4,5-tetrahydro-1h-3-benzapines having in position 6 the substituted mercapto group Download PDF

Info

Publication number: CS213381B2
Authority: CS; Czechoslovakia
Prior art keywords: solution; tetrahydro; methyl; mol; benzazepine
Prior art date: 1978-07-07

Application number

CS794635A

Other languages

Czech (cs)

English (en)

Inventor

Kenneth G Holden

Carl H H Kaiser

Original Assignee

Smithkline Corp

Priority date (The priority date 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 date listed.)

1978-07-07

Filing date

1979-07-02

Publication date

1982-04-09

1979-07-02 Application filed by Smithkline Corp filed Critical Smithkline Corp

1982-04-09 Publication of CS213381B2 publication Critical patent/CS213381B2/cs

Links

125000003396 thiol group Chemical group [H]S* 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title 1
-1 mercapto substituted-2,3,4,5-tetrahydro-1H-3-benzazepines Chemical class 0.000 claims abstract description 38
239000002253 acid Substances 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims description 41
238000000034 method Methods 0.000 claims description 30
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
RSRUDTPYRBLHEO-UHFFFAOYSA-N Benalfocin Chemical compound C1CN(C)CCC2=CC=CC(Cl)=C21 RSRUDTPYRBLHEO-UHFFFAOYSA-N 0.000 abstract description 2
239000000243 solution Substances 0.000 description 192
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 125
239000000203 mixture Substances 0.000 description 125
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 72
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
239000011541 reaction mixture Substances 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
238000003756 stirring Methods 0.000 description 30
239000000284 extract Substances 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
238000002844 melting Methods 0.000 description 26
230000008018 melting Effects 0.000 description 26
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
238000010992 reflux Methods 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
239000007788 liquid Substances 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000005457 ice water Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 13
241001465754 Metazoa Species 0.000 description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 12
239000000725 suspension Substances 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 11
239000012299 nitrogen atmosphere Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 10
239000000908 ammonium hydroxide Substances 0.000 description 10
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
239000012458 free base Substances 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
206010047700 Vomiting Diseases 0.000 description 8
239000012954 diazonium Substances 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
230000008673 vomiting Effects 0.000 description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
150000001989 diazonium salts Chemical class 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
235000010288 sodium nitrite Nutrition 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
102000015554 Dopamine receptor Human genes 0.000 description 6
108050004812 Dopamine receptor Proteins 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 6
230000000903 blocking effect Effects 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000008194 pharmaceutical composition Substances 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
239000003937 drug carrier Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000700159 Rattus Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
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230000000561 anti-psychotic effect Effects 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
230000035939 shock Effects 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
235000021355 Stearic acid Nutrition 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
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OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
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YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
229910000365 copper sulfate Inorganic materials 0.000 description 3
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
230000017858 demethylation Effects 0.000 description 3
238000010520 demethylation reaction Methods 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
239000012467 final product Substances 0.000 description 3
235000019256 formaldehyde Nutrition 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
229930182817 methionine Natural products 0.000 description 3
235000006109 methionine Nutrition 0.000 description 3
238000002156 mixing Methods 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
239000008117 stearic acid Substances 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
MYOAKAGSEUSIMT-UHFFFAOYSA-N 1h-3-benzazepine Chemical compound C1C=NC=CC2=CC=CC=C12 MYOAKAGSEUSIMT-UHFFFAOYSA-N 0.000 description 2
MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical compound N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 description 2
MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical class C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
LBVJZXJAZRXUOT-UHFFFAOYSA-N 3-methyl-6-phenylsulfanyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C=12CCN(C)CCC2=CC=CC=1SC1=CC=CC=C1 LBVJZXJAZRXUOT-UHFFFAOYSA-N 0.000 description 2
XWXULQBTDLGTNR-UHFFFAOYSA-N 3-methyl-6-phenylsulfanyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol Chemical compound C=12CCN(C)CCC2=CC(O)=C(O)C=1SC1=CC=CC=C1 XWXULQBTDLGTNR-UHFFFAOYSA-N 0.000 description 2
YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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230000002378 acidificating effect Effects 0.000 description 2
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230000008485 antagonism Effects 0.000 description 2
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239000011668 ascorbic acid Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000003637 basic solution Substances 0.000 description 2
150000008038 benzoazepines Chemical class 0.000 description 2
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FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
JWGIMPLAVQQCFH-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)-2-(2-fluoro-3,4-dimethoxyphenyl)acetamide Chemical compound COC(OC)CNC(=O)CC1=CC=C(OC)C(OC)=C1F JWGIMPLAVQQCFH-UHFFFAOYSA-N 0.000 description 1
VBBHYFZIAZEXOY-UHFFFAOYSA-N n-(6-chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-9-yl)acetamide Chemical compound C1CN(C)CCC2=C(Cl)C=CC(NC(C)=O)=C21 VBBHYFZIAZEXOY-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000013612 plasmid Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000003340 retarding agent Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
VSGXHZUTTFLSBC-UHFFFAOYSA-N thiophene-3-thiol Chemical compound SC=1C=CSC=1 VSGXHZUTTFLSBC-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 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
- A61P25/20—Hypnotics; Sedatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Anesthesiology (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CS794635A 1978-07-07 1979-07-02 Method of making the derivatives of 2,3,4,5-tetrahydro-1h-3-benzapines having in position 6 the substituted mercapto group CS213381B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US92261378A	1978-07-07	1978-07-07

Publications (1)

Publication Number	Publication Date
CS213381B2 true CS213381B2 (en)	1982-04-09

Family

ID=25447325

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794635A CS213381B2 (en)	1978-07-07	1979-07-02	Method of making the derivatives of 2,3,4,5-tetrahydro-1h-3-benzapines having in position 6 the substituted mercapto group

Country Status (24)

Country	Link
EP (2)	EP0007070B1 (de)
JP (1)	JPS5511584A (de)
AR (1)	AR222828A1 (de)
AU (1)	AU525789B2 (de)
CA (1)	CA1115271A (de)
CS (1)	CS213381B2 (de)
DD (1)	DD147355A5 (de)
DE (1)	DE2964530D1 (de)
DK (1)	DK156001C (de)
ES (3)	ES482282A1 (de)
FI (1)	FI67215C (de)
GR (1)	GR69675B (de)
HU (1)	HU179315B (de)
IE (1)	IE48654B1 (de)
IL (1)	IL57532A (de)
IT (1)	IT1193190B (de)
JO (1)	JO1273B1 (de)
NO (1)	NO152213C (de)
NZ (1)	NZ190745A (de)
PH (1)	PH15754A (de)
PL (1)	PL216908A1 (de)
PT (1)	PT69855A (de)
SU (1)	SU1029827A3 (de)
ZA (1)	ZA792785B (de)

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DE3119874A1 (de)	1981-05-19	1982-12-09	Dr. Karl Thomae Gmbh, 7950 Biberach	"benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel"
US4469634A (en) *	1982-07-29	1984-09-04	Smithkline Beckman Corporation	Allyloxy- and allylthio-2,3,4,5-tetrahydro-1H-3-benzazepines
US4652642A (en) *	1984-08-23	1987-03-24	Smithkline Beckman Corporation	Azidobenzazepines
US4683229A (en) *	1986-03-17	1987-07-28	Smithkline Beckman Corporation	6-halo-9-alkenyleneoxy-3-alkyl-2,3,4,5-tetrahydro-(1H-3)-benzazepines and their use as selective alpha-adrenergic receptor antagonists
US5942250A (en) *	1986-12-23	1999-08-24	Tristrata Technology, Inc.	Compositions and methods for enhancing the topical effects of sunscreen agents
US6384079B1 (en)	1986-12-23	2002-05-07	Tristrata Technology, Incorporated	Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging
GB9119467D0 (en) *	1991-09-12	1991-10-23	Smithkline Beecham Corp	Chemical compounds
GB9708805D0 (en)	1997-05-01	1997-06-25	Smithkline Beecham Plc	Compounds
GB9810876D0 (en)	1998-05-20	1998-07-22	Smithkline Beecham Plc	Compounds
CA2346689A1 (en)	1998-10-08	2000-04-20	Gregor James Macdonald	Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents)
US6953787B2 (en)	2002-04-12	2005-10-11	Arena Pharmaceuticals, Inc.	5HT2C receptor modulators
ATE327234T1 (de) *	2002-10-07	2006-06-15	Glaxo Group Ltd	Sulfonamidderivate als antipsychotische mittel
US8367657B2 (en)	2003-06-17	2013-02-05	Arena Pharmaceuticals, Inc.	Processes for preparing 3-benzazepines
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
CA2556390C (en) *	2004-02-25	2012-10-02	Eli Lilly And Company	6-substituted 2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists
EP2149562A1 (de)	2004-12-21	2010-02-03	Arena Pharmaceuticals, Inc.	Verfahren zur Herstellung des (R)-8-Chlor-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepinhydrochlorid-Hemihydrat
NZ589951A (en)	2004-12-23	2012-11-30	Arena Pharm 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
EP2099743B1 (de)	2006-12-05	2014-08-27	Arena Pharmaceuticals, Inc.	Verfahren zur herstellung von (r)-8-chlor-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin und zwischenprodukten davon
US8822727B2 (en)	2008-03-04	2014-09-02	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
WO2010148207A2 (en)	2009-06-18	2010-12-23	Arena Pharmaceuticals, Inc.	Processes for the preparation of 5-ht2c receptor agonists
WO2011153206A1 (en)	2010-06-02	2011-12-08	Arena Pharmaceuticals, Inc.	Processes for the preparation of 5-ht2c receptor agonists
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
EA201390335A1 (ru)	2010-09-01	2013-09-30	Арена Фармасьютикалз, Инк.	Введение лоркасерина индивидуумам с почечной недостаточностью
KR20130101524A (ko)	2010-09-01	2013-09-13	아레나 파마슈티칼스, 인크.	5-ｈｔ2ｃ 아고니스트의 비-흡습성 염
KR20180118801A (ko)	2010-09-01	2018-10-31	에자이 알앤드디 매니지먼트 가부시키가이샤	체중 관리에 유용한 5-ｈｔ2ｃ 작동제의 변형-방출 투여 형태
RU2674670C1 (ru)	2012-10-09	2018-12-12	Арена Фармасьютикалз, Инк.	Способ коррекции массы тела
CN116655892B (zh) *	2023-05-18	2026-03-31	常州大学	一种交联聚合物有机电极材料及其制备方法与应用

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Publication number	Priority date	Publication date	Assignee	Title
US2520264A (en) *	1947-08-26	1950-08-29	Maltbie Lab Inc	Substituted 3, 1-benz-2, 3, 4, 5-tetrahydroazepines
US3483185A (en) *	1966-08-16	1969-12-09	American Home Prod	N-substituted 2,3,4,5-tetrahydro-1h-3-benzazepines
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
US3671519A (en)	1969-07-14	1972-06-20	American Home Prod	N-substituted 2,3,4,5,-tetrahydro-1h-3-benzazepines
US3716639A (en)	1970-03-11	1973-02-13	Ciba Geigy Corp	Anorexigenic tetrahydrobenzazepines
US3752892A (en)	1970-03-11	1973-08-14	Ciba Geigy Corp	Anorexigenic tetrahydrobenzazepine derivative method and composition thereof
US4111957A (en) *	1977-02-02	1978-09-05	Smithkline Corporation	Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds
US4108989A (en) *	1977-04-01	1978-08-22	Smithkline Corporation	2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones

1979
- 1979-06-05 ZA ZA792785A patent/ZA792785B/xx unknown
- 1979-06-11 IL IL57532A patent/IL57532A/xx unknown
- 1979-06-15 NZ NZ190745A patent/NZ190745A/xx unknown
- 1979-06-28 JP JP8252779A patent/JPS5511584A/ja active Granted
- 1979-07-02 PH PH22728A patent/PH15754A/en unknown
- 1979-07-02 PT PT69855A patent/PT69855A/pt unknown
- 1979-07-02 DK DK278379A patent/DK156001C/da not_active IP Right Cessation
- 1979-07-02 CS CS794635A patent/CS213381B2/cs unknown
- 1979-07-03 GR GR59498A patent/GR69675B/el unknown
- 1979-07-03 CA CA331,022A patent/CA1115271A/en not_active Expired
- 1979-07-03 AU AU48613/79A patent/AU525789B2/en not_active Ceased
- 1979-07-04 EP EP79102279A patent/EP0007070B1/de not_active Expired
- 1979-07-04 EP EP82105188A patent/EP0080012B1/de not_active Expired
- 1979-07-04 DE DE7979102279T patent/DE2964530D1/de not_active Expired
- 1979-07-05 FI FI792125A patent/FI67215C/fi not_active IP Right Cessation
- 1979-07-05 HU HU79SI1705A patent/HU179315B/hu unknown
- 1979-07-06 ES ES482282A patent/ES482282A1/es not_active Expired
- 1979-07-06 AR AR277218A patent/AR222828A1/es active
- 1979-07-06 IT IT24165/79A patent/IT1193190B/it active
- 1979-07-06 PL PL21690879A patent/PL216908A1/xx unknown
- 1979-07-06 SU SU792783746A patent/SU1029827A3/ru active
- 1979-07-06 ES ES482276A patent/ES482276A1/es not_active Expired
- 1979-07-06 ES ES482281A patent/ES482281A1/es not_active Expired
- 1979-07-06 DD DD79214179A patent/DD147355A5/de unknown
- 1979-07-06 NO NO792267A patent/NO152213C/no unknown
- 1979-07-07 JO JO19791273A patent/JO1273B1/en active
- 1979-08-08 IE IE1276/79A patent/IE48654B1/en unknown

Also Published As

Publication number	Publication date
AU525789B2 (en)	1982-12-02
JPS5511584A (en)	1980-01-26
ZA792785B (en)	1980-08-27
IE48654B1 (en)	1985-04-03
IL57532A0 (en)	1979-10-31
EP0080012A1 (de)	1983-06-01
EP0080012B1 (de)	1986-04-09
ES482282A1 (es)	1980-04-01
FI67215B (fi)	1984-10-31
EP0007070A1 (de)	1980-01-23
HU179315B (en)	1982-09-28
SU1029827A3 (ru)	1983-07-15
ES482281A1 (es)	1980-04-01
NO152213C (no)	1985-08-28
FI792125A7 (fi)	1980-01-08
FI67215C (fi)	1985-02-11
CA1115271A (en)	1981-12-29
PL216908A1 (de)	1980-08-11
JPH0153271B2 (de)	1989-11-13
ES482276A1 (es)	1980-04-01
JO1273B1 (en)	1986-11-30
DK156001B (da)	1989-06-12
PT69855A (en)	1979-08-01
DD147355A5 (de)	1981-04-01
EP0007070B1 (de)	1983-01-19
IE791276L (en)	1980-01-07
DK278379A (da)	1980-01-08
NZ190745A (en)	1981-01-23
NO152213B (no)	1985-05-13
PH15754A (en)	1983-03-18
IT7924165A0 (it)	1979-07-06
GR69675B (de)	1982-07-07
AR222828A1 (es)	1981-06-30
IT1193190B (it)	1988-06-02
DE2964530D1 (en)	1983-02-24
IL57532A (en)	1982-08-31
DK156001C (da)	1989-11-06
AU4861379A (en)	1980-02-07
NO792267L (no)	1980-01-08

Publication	Publication Date	Title
EP0007070B1 (de)	1983-01-19	2,3,4,5-Tetrahydro-1H-3-Benzazepine, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen mit Dopamin-Rezeptor-Blocker Aktivität
CA1092107A (en)	1980-12-23	Trisubstituted 1-phenyl-2,3,4,5-tetrahydro-1h-3- benzazepine compounds
US4265890A (en)	1981-05-05	6-Phenyl thio- and 6-cyclohexyl thio-2,3,4,5-tetrahydro-1H-3-benzazepines
US4108989A (en)	1978-08-22	2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones
HU187425B (en)	1986-01-28	Process for producing morphinane derivatives
IE44379B1 (en)	1981-11-04	Thiazolo (3,4-b)isoquinoline derivatives
JPS6154794B2 (de)	1986-11-25
JPS6040422B2 (ja)	1985-09-11	置換１‐アルキルチオフエニル―２，３，４，５―テトラヒドロ―１ｈ―３―ベンズアゼピン化合物
EP0004794B1 (de)	1982-04-28	Benzazepinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
US4206210A (en)	1980-06-03	Alkylthio-7,8-dihdroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines having dopaminergic activity
CA1090334A (en)	1980-11-25	Alkylthio-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro- 1h-3-benzazepines having dopaminergic activity
EP0027348B1 (de)	1984-08-08	7,8-Dihydroxy-1-(sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Zusammensetzungen
EP0127423B1 (de)	1988-02-03	1-(4'-Verzweigte alkylsulfonylphenyl)-6-chloro-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-3-Benzazepine
KR830001501B1 (ko)	1983-08-03	메르캎토 치환-2, 3, 4, 5-테트라히드로-1h-3-벤자제핀류의 제조방법
HU177901B (en)	1982-01-28	Process for preparing 8- and/or 9-substituted 2,3,4,5-tetrahydro-1h-2-benzazepine derivatives
IE48655B1 (en)	1985-04-03	6-chloro-3-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine,its acid addition salts and its use as an intermediate
EP0044709B1 (de)	1984-03-14	Dopaminerg wirkende Benzazepine
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