IL31715A - Derivatives of 5h-dibenz(b,f)azepine,their preparation and pharmaceutical compositions containing them - Google Patents

Derivatives of 5h-dibenz(b,f)azepine,their preparation and pharmaceutical compositions containing them

Info

Publication number: IL31715A
Authority: IL; Israel
Prior art keywords: dibenz; dihydro; azepine; acid; compound
Prior art date: 1968-02-29

Application number

IL31715A

Other languages

English (en)

Other versions

IL31715A0 (en

Original Assignee

Ciba Geigy Ag

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.)

1968-02-29

Filing date

1969-02-28

Publication date

1972-01-27

1969-02-28 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1969-04-30 Publication of IL31715A0 publication Critical patent/IL31715A0/xx

1972-01-27 Publication of IL31715A publication Critical patent/IL31715A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 2
LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 65
150000003839 salts Chemical class 0.000 claims description 60
-1 carboxylic acid imido ester Chemical class 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 33
238000000034 method Methods 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
150000007529 inorganic bases Chemical class 0.000 claims description 16
150000007530 organic bases Chemical class 0.000 claims description 16
150000001735 carboxylic acids Chemical class 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 12
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 11
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 11
239000002609 medium Substances 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000005907 alkyl ester group Chemical group 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
RNUGOQPIJUMZPY-UHFFFAOYSA-N 2-(11-methyl-5,6-dihydrobenzo[b][1]benzazepin-2-yl)acetic acid Chemical compound CN1C2=C(CCC3=C1C=CC=C3)C=CC(=C2)CC(=O)O RNUGOQPIJUMZPY-UHFFFAOYSA-N 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
230000003301 hydrolyzing effect Effects 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
FSSVULOSAXBENC-UHFFFAOYSA-N C1=C(C=CC=2NC3=C(CCC21)C=CC=C3)CC(=O)O Chemical compound C1=C(C=CC=2NC3=C(CCC21)C=CC=C3)CC(=O)O FSSVULOSAXBENC-UHFFFAOYSA-N 0.000 claims description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
238000006136 alcoholysis reaction Methods 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
CCLBOAZTYCBGSI-UHFFFAOYSA-N 2-(1h-azepin-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC=CN1 CCLBOAZTYCBGSI-UHFFFAOYSA-N 0.000 claims description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
150000001447 alkali salts Chemical class 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
239000001569 carbon dioxide Substances 0.000 claims description 2
229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 207
239000000243 solution Substances 0.000 description 161
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 79
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
238000001704 evaporation Methods 0.000 description 67
239000000203 mixture Substances 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
230000008020 evaporation Effects 0.000 description 64
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 56
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 53
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
239000003921 oil Substances 0.000 description 43
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 35
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
239000012074 organic phase Substances 0.000 description 26
229910000029 sodium carbonate Inorganic materials 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
229960000583 acetic acid Drugs 0.000 description 21
239000007858 starting material Substances 0.000 description 20
239000013078 crystal Substances 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000000155 melt Substances 0.000 description 16
239000003208 petroleum Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
238000001816 cooling Methods 0.000 description 14
238000003756 stirring Methods 0.000 description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
150000002825 nitriles Chemical class 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
238000009835 boiling Methods 0.000 description 11
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 10
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
239000000725 suspension Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012071 phase Substances 0.000 description 9
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 8
239000012346 acetyl chloride Substances 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000013543 active substance Substances 0.000 description 7
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
239000005457 ice water Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
BXNVHVQDJDXNTE-UHFFFAOYSA-N 2-(1h-azepin-3-yl)acetic acid Chemical compound OC(=O)CC1=CNC=CC=C1 BXNVHVQDJDXNTE-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
239000005864 Sulphur Substances 0.000 description 6
239000012670 alkaline solution Substances 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
229960001760 dimethyl sulfoxide Drugs 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
JXBQUFOYEZUECA-UHFFFAOYSA-N 2-(6,11-dihydro-5H-benzo[b][1]benzazepin-2-yl)acetic acid Chemical compound C1=CC(=CC=2NC3=C(CCC21)C=CC=C3)CC(=O)O JXBQUFOYEZUECA-UHFFFAOYSA-N 0.000 description 5
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 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
238000000605 extraction Methods 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000004133 Sodium thiosulphate Substances 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
239000008298 dragée Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
235000019345 sodium thiosulphate Nutrition 0.000 description 4
239000000454 talc Substances 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
150000003556 thioamides Chemical class 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
OWDFWZIDRGMRKV-UHFFFAOYSA-N 11-acetyl-5,6-dihydrobenzo[b][1]benzazepine-2-carboxylic acid Chemical compound C1CC2=CC=C(C(O)=O)C=C2N(C(=O)C)C2=CC=CC=C21 OWDFWZIDRGMRKV-UHFFFAOYSA-N 0.000 description 3
LVSZBSHVNWSRNT-UHFFFAOYSA-N 11-benzyl-3-(bromomethyl)-5,6-dihydrobenzo[b][1]benzazepine Chemical compound BrCC1=CC2=C(N(C3=C(CC2)C=CC=C3)CC3=CC=CC=C3)C=C1 LVSZBSHVNWSRNT-UHFFFAOYSA-N 0.000 description 3
JCFJWZQIUOFCKV-UHFFFAOYSA-N 1h-azepin-3-ylmethanol Chemical compound OCC1=CNC=CC=C1 JCFJWZQIUOFCKV-UHFFFAOYSA-N 0.000 description 3
FOUCGDBLVIXCOZ-UHFFFAOYSA-N 2-(1h-azepin-3-yl)acetonitrile Chemical compound N#CCC1=CNC=CC=C1 FOUCGDBLVIXCOZ-UHFFFAOYSA-N 0.000 description 3
DVQLXCHGEWVGGJ-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine-2-carboxylic acid Chemical class C1CC2=CC=CC=C2NC2=CC(C(=O)O)=CC=C21 DVQLXCHGEWVGGJ-UHFFFAOYSA-N 0.000 description 3
NIUOXYCPIIUVKB-UHFFFAOYSA-N ClC1=CC2=C(CCC3=C(N2C)C=CC(=C3)C=O)C=C1 Chemical compound ClC1=CC2=C(CCC3=C(N2C)C=CC(=C3)C=O)C=C1 NIUOXYCPIIUVKB-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
239000001828 Gelatine Substances 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
235000019759 Maize starch Nutrition 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000005708 Sodium hypochlorite Substances 0.000 description 3
238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000006053 organic reaction Methods 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
NMZOSOMVILZBJL-UHFFFAOYSA-N 1-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C1CC2=CC=C(Cl)C=C2N(C(=O)C)C2=CC=CC=C21 NMZOSOMVILZBJL-UHFFFAOYSA-N 0.000 description 2
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239000000872 buffer Substances 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
229940105305 carbon monoxide Drugs 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
WGVVFCGXXDJXGW-UHFFFAOYSA-N diethyl 2-(11-methyl-5,6-dihydrobenzo[b][1]benzazepin-3-yl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)C1=CC2=C(N(C3=C(CC2)C=CC=C3)C)C=C1)=O WGVVFCGXXDJXGW-UHFFFAOYSA-N 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
RKJMHZBROOPSPU-UHFFFAOYSA-N methyl 1h-azepine-3-carboxylate Chemical compound COC(=O)C1=CNC=CC=C1 RKJMHZBROOPSPU-UHFFFAOYSA-N 0.000 description 1
KABYRJRNHOANDT-UHFFFAOYSA-N methyl 2-(6,11-dihydro-5H-benzo[b][1]benzazepin-2-yl)acetate Chemical compound COC(CC=1C=CC2=C(NC3=C(CC2)C=CC=C3)C1)=O KABYRJRNHOANDT-UHFFFAOYSA-N 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000007655 standard test method Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000037072 sun protection Effects 0.000 description 1
230000008961 swelling Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 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
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
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
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- G—PHYSICS
- G01—MEASURING; TESTING
- G01M—TESTING STATIC OR DYNAMIC BALANCE OF MACHINES OR STRUCTURES; TESTING OF STRUCTURES OR APPARATUS, NOT OTHERWISE PROVIDED FOR
- G01M3/00—Investigating fluid-tightness of structures
- G01M3/02—Investigating fluid-tightness of structures by using fluid or vacuum

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Physics & Mathematics (AREA)
Animal Behavior & Ethology (AREA)
General Physics & Mathematics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Cosmetics (AREA)
Plural Heterocyclic Compounds (AREA)

IL31715A 1968-02-29 1969-02-28 Derivatives of 5h-dibenz(b,f)azepine,their preparation and pharmaceutical compositions containing them IL31715A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH305568A CH501635A (de)	1968-02-29	1968-02-29	Verfahren zur Herstellung von neuen Derivaten des 5H-Dibenz(b,f)azepins

Publications (2)

Publication Number	Publication Date
IL31715A0 IL31715A0 (en)	1969-04-30
IL31715A true IL31715A (en)	1972-01-27

Family

ID=4247593

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL31715A IL31715A (en)	1968-02-29	1969-02-28	Derivatives of 5h-dibenz(b,f)azepine,their preparation and pharmaceutical compositions containing them

Country Status (13)

Country	Link
US (1)	US3624075A (de)
JP (3)	JPS4927876B1 (de)
AT (5)	AT286997B (de)
BE (1)	BE729209A (de)
BR (1)	BR6906750D0 (de)
CH (5)	CH501637A (de)
DE (2)	DE1965988A1 (de)
DK (1)	DK122725B (de)
ES (5)	ES364637A1 (de)
FR (1)	FR2002897A1 (de)
GB (1)	GB1259648A (de)
IL (1)	IL31715A (de)
NL (1)	NL6902779A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4230703A (en) *	1977-04-01	1980-10-28	Teikoku Hormone Mfg. Co., Ltd.	11-Oxodibenz(b,e)azepines
US6468996B1 (en) *	1998-10-21	2002-10-22	Novo Nordisk A/S	Substituted hetero-polycyclic compounds as PPARα and PPARγ activators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH414643A (de) *	1962-12-04	1966-06-15	Geigy Ag J R	Verfahren zur Herstellung von neuen Azepinderivaten

1968
- 1968-02-29 CH CH1281570A patent/CH501637A/de not_active IP Right Cessation
- 1968-02-29 CH CH1281670A patent/CH501638A/de not_active IP Right Cessation
- 1968-02-29 CH CH305568A patent/CH501635A/de not_active IP Right Cessation
- 1968-02-29 CH CH1281770A patent/CH501639A/de not_active IP Right Cessation
- 1968-02-29 CH CH1281870A patent/CH501640A/de not_active IP Right Cessation
1969
- 1969-02-21 DK DK98269AA patent/DK122725B/da unknown
- 1969-02-21 NL NL6902779A patent/NL6902779A/xx unknown
- 1969-02-24 US US801801A patent/US3624075A/en not_active Expired - Lifetime
- 1969-02-27 FR FR6905170A patent/FR2002897A1/fr not_active Withdrawn
- 1969-02-28 AT AT201770A patent/AT286997B/de not_active IP Right Cessation
- 1969-02-28 DE DE19691965988 patent/DE1965988A1/de active Pending
- 1969-02-28 GB GB1259648D patent/GB1259648A/en not_active Expired
- 1969-02-28 IL IL31715A patent/IL31715A/en unknown
- 1969-02-28 ES ES364637A patent/ES364637A1/es not_active Expired
- 1969-02-28 BE BE729209D patent/BE729209A/xx unknown
- 1969-02-28 JP JP44014996A patent/JPS4927876B1/ja active Pending
- 1969-02-28 AT AT02014/70A patent/AT286996B/de not_active IP Right Cessation
- 1969-02-28 DE DE19691910291 patent/DE1910291A1/de active Pending
- 1969-02-28 ES ES364633A patent/ES364633A1/es not_active Expired
- 1969-02-28 AT AT201570A patent/AT287729B/de not_active IP Right Cessation
- 1969-02-28 ES ES364632A patent/ES364632A1/es not_active Expired
- 1969-02-28 AT AT203869A patent/AT286994B/de not_active IP Right Cessation
- 1969-02-28 ES ES364634A patent/ES364634A1/es not_active Expired
- 1969-02-28 ES ES364635A patent/ES364635A1/es not_active Expired
- 1969-02-28 AT AT201670A patent/AT289815B/de not_active IP Right Cessation
- 1969-02-28 BR BR206750/69A patent/BR6906750D0/pt unknown
1971
- 1971-07-02 JP JP46048716A patent/JPS4929196B1/ja active Pending
- 1971-07-02 JP JP46048717A patent/JPS4929197B1/ja active Pending

Also Published As

Publication number	Publication date
AT286996B (de)	1971-01-11
CH501640A (de)	1971-01-15
NL6902779A (de)	1969-09-02
DK122725B (da)	1972-04-04
ES364635A1 (es)	1971-02-01
FR2002897A1 (de)	1969-10-31
JPS4929197B1 (de)	1974-08-01
GB1259648A (de)	1972-01-05
ES364634A1 (es)	1971-02-01
ES364637A1 (es)	1971-02-01
CH501635A (de)	1971-01-15
ES364632A1 (es)	1971-02-01
US3624075A (en)	1971-11-30
CH501638A (de)	1971-01-15
AT286994B (de)	1971-01-11
BE729209A (de)	1969-08-28
JPS4929196B1 (de)	1974-08-01
DE1965988A1 (de)	1970-11-19
IL31715A0 (en)	1969-04-30
CH501639A (de)	1971-01-15
JPS4927876B1 (de)	1974-07-22
AT286997B (de)	1971-01-11
DE1910291A1 (de)	1969-11-06
ES364633A1 (es)	1971-02-01
AT287729B (de)	1971-02-10
BR6906750D0 (pt)	1973-04-19
CH501637A (de)	1971-01-15
AT289815B (de)	1971-05-10

Publication	Publication Date	Title
US3535344A (en)	1970-10-20	3,4-cis-4-aryl-isoflavanes
US4282248A (en)	1981-08-04	Pinene derivatives and pharmaceutical compositions containing the same
US3420851A (en)	1969-01-07	Novel dibenzoxepines
US4194045A (en)	1980-03-18	1-(3,3-Diaryl-3-oxadiazolalkyl)-4-phenyl-4-piperidinomethanols and related compounds
HU188840B (en)	1986-05-28	Process for preparing glycerine derivatives and pharmaceutical compositions containing such compounds as active substances
NO138565B (no)	1978-06-19	Analogifremgangsmaate ved fremstilling av terapeutisk aktive piperazinyl-propyl-1,2,4-triazolinonderivater
NO161619B (no)	1989-05-29	Analogifremgangsmaate for fremstilling av terapeutisk aktive substituerte 5,11-dihydro-6-dibenz(b,e)-azepin-6-on-derivater.
US4072756A (en)	1978-02-07	Tricyclo piperidino ketones and soporific compositions thereof
US3624075A (en)	1971-11-30	Dibenzazepine acetic acid derivatives
US4341781A (en)	1982-07-27	Pyridazopyridazine derivatives
NO750264L (de)	1975-09-01
US4278798A (en)	1981-07-14	1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxonicotinic acid and esters thereof
CA1065871A (en)	1979-11-06	Process for the production of oxygenated azatetracyclic compounds
JPH0256478A (ja)	1990-02-26	２，３，４，５―テトラヒドロ―１―ベンズオキセピン―３，５―ジオン誘導体及びその製法
US4337260A (en)	1982-06-29	Imidazopyridine-spiro-piperidine compounds
GB2027022A (en)	1980-02-13	Pyridoxine derivatives and their use
FI63578C (fi)	1983-07-11	Analogifoerfarande foer framstaellning av nya farmakologiskt verksamma 1,3,4,14b-tetrahydro-2h 10h-pyrazino(1,2-a)pyrrolo(2,1-c)(1,4)bensodiazepiner
US3639598A (en)	1972-02-01	Anti-inflammatory compositions and method
IL28867A (en)	1972-04-27	1-adamantyl and 1-adamantylmethyl carbonates of testosterone and derivatives thereof
US4374261A (en)	1983-02-15	1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxo-nicotinic acid and esters thereof
NZ233058A (en)	1991-05-28	2,8-disubstituted dibenzofuran derivatives and pharmaceutical compositions
US3751436A (en)	1973-08-07	2,3-dihydro-5-(2-methylene-alkanoyl)-benzofuran-2-carboxylic acid alkyl and cycloalkyl esters
US3712946A (en)	1973-01-23	Certain oxy-substituted benzo quinolizinium compounds and their use
US4314063A (en)	1982-02-02	1-Ethyl-1,4,5,6-tetrahydro-6-(2-naphthyl)-4-oxo-nicotinic acid and lower alkyl esters thereof
US4158061A (en)	1979-06-12	2,9-Dioxatricyclo[4,3,1,03,7 ] decane derivatives, processes for their preparation and pharmaceutical compositions thereof