PH26368A - Carbamic acid esters of benzazepines - Google Patents
Carbamic acid esters of benzazepines Download PDFInfo
- Publication number
- PH26368A PH26368A PH38219A PH38219A PH26368A PH 26368 A PH26368 A PH 26368A PH 38219 A PH38219 A PH 38219A PH 38219 A PH38219 A PH 38219A PH 26368 A PH26368 A PH 26368A
- Authority
- PH
- Philippines
- Prior art keywords
- benzazepine
- methyl
- alkyl
- chloro
- tetrahydro
- Prior art date
Links
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 7
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 6
- 150000008038 benzoazepines Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- -1 CN R<4> is H Chemical class 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- GICIECWTEWJCRE-UHFFFAOYSA-N 3,4,4,7-tetramethyl-2,3-dihydro-1h-naphthalene Chemical compound CC1=CC=C2C(C)(C)C(C)CCC2=C1 GICIECWTEWJCRE-UHFFFAOYSA-N 0.000 claims 1
- YHPSAPRUVAIUKO-UHFFFAOYSA-N 5-methyl-3H-3-benzazepine Chemical compound CC1=CNC=CC2=C1C=CC=C2 YHPSAPRUVAIUKO-UHFFFAOYSA-N 0.000 claims 1
- 229920001817 Agar Polymers 0.000 claims 1
- 244000099147 Ananas comosus Species 0.000 claims 1
- 235000007119 Ananas comosus Nutrition 0.000 claims 1
- 241000272517 Anseriformes Species 0.000 claims 1
- 241001363698 Batis <Aves> Species 0.000 claims 1
- 235000016068 Berberis vulgaris Nutrition 0.000 claims 1
- 241000335053 Beta vulgaris Species 0.000 claims 1
- 102000017914 EDNRA Human genes 0.000 claims 1
- 101150062404 EDNRA gene Proteins 0.000 claims 1
- 240000002390 Pandanus odoratissimus Species 0.000 claims 1
- 235000005311 Pandanus odoratissimus Nutrition 0.000 claims 1
- 208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 239000008272 agar Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 235000005822 corn Nutrition 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- FESBVLZDDCQLFY-UHFFFAOYSA-N sete Chemical compound [Te]=[Se] FESBVLZDDCQLFY-UHFFFAOYSA-N 0.000 claims 1
- 239000000651 prodrug Substances 0.000 abstract description 31
- 229940002612 prodrug Drugs 0.000 abstract description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 125000004122 cyclic group Chemical group 0.000 abstract description 6
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical group C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000002541 furyl group Chemical group 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 abstract description 4
- 125000001544 thienyl group Chemical group 0.000 abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005864 Sulphur Substances 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 125000004193 piperazinyl group Chemical group 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 230000000144 pharmacologic effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000000875 corresponding effect Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000003389 potentiating effect Effects 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical class C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CTPKSRZFJSJGML-UHFFFAOYSA-N sulfiram Chemical compound CCN(CC)C(=S)SC(=S)N(CC)CC CTPKSRZFJSJGML-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 1
- PAMFFHMXFOFAPI-UHFFFAOYSA-N 1h-1-benzazepin-7-ol Chemical compound N1C=CC=CC2=CC(O)=CC=C21 PAMFFHMXFOFAPI-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000304337 Cuminum cyminum Species 0.000 description 1
- 235000007129 Cuminum cyminum Nutrition 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 101100007538 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cpc-1 gene Proteins 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BLWYXBNNBYXPPL-YFKPBYRVSA-N methyl (2s)-pyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1 BLWYXBNNBYXPPL-YFKPBYRVSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK107688A DK107688D0 (da) | 1988-03-01 | 1988-03-01 | Carbaminsyreestere af substituerede 7-hydroxy-2,3,4,5-tetrahydro-1h-3-benzazepiner |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26368A true PH26368A (en) | 1992-06-01 |
Family
ID=8100728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH38219A PH26368A (en) | 1988-03-01 | 1989-02-20 | Carbamic acid esters of benzazepines |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5017571A (de) |
| EP (1) | EP0331130B1 (de) |
| JP (1) | JPH01254679A (de) |
| KR (1) | KR0126473B1 (de) |
| AT (1) | ATE95179T1 (de) |
| AU (1) | AU613716B2 (de) |
| CA (1) | CA1312863C (de) |
| DE (1) | DE68909448T2 (de) |
| DK (1) | DK107688D0 (de) |
| ES (1) | ES2059592T3 (de) |
| FI (1) | FI94955C (de) |
| IE (1) | IE64247B1 (de) |
| IL (1) | IL89207A0 (de) |
| NO (1) | NO173825C (de) |
| NZ (1) | NZ228151A (de) |
| PH (1) | PH26368A (de) |
| PT (1) | PT89887B (de) |
| ZA (1) | ZA891537B (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK67489D0 (da) * | 1989-02-14 | 1989-02-14 | Novo Industri As | Nye benzazepinderivater |
| AU666318B2 (en) * | 1991-06-28 | 1996-02-08 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| US5939412A (en) * | 1992-06-26 | 1999-08-17 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| US5470850A (en) * | 1992-02-24 | 1995-11-28 | Novo Nordisk A/S | 2,3,4,5-tetrahydro-1H-3-benzazepines |
| MA23420A1 (fr) * | 1994-01-07 | 1995-10-01 | Smithkline Beecham Corp | Antagonistes bicycliques de fibrinogene. |
| US6458784B1 (en) | 1994-06-29 | 2002-10-01 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
| US5977101A (en) * | 1995-06-29 | 1999-11-02 | Smithkline Beecham Corporation | Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity |
| US20030125317A1 (en) * | 1996-10-02 | 2003-07-03 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
| US7704993B2 (en) | 2003-06-17 | 2010-04-27 | 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 |
| BRPI0515862A2 (pt) | 2004-12-23 | 2011-10-11 | Arena Pharm Inc | uso de fentermina e agonista seletivo do receptor de 5ht-2c na preparação de composições, composições moduladoras do receptor de 5ht-2c e forma de dosagem unitária compreendendo as mesmas |
| 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 |
| KR20130112848A (ko) | 2010-06-02 | 2013-10-14 | 아레나 파마슈티칼스, 인크. | 5-ｈｔ2ｃ 수용체 아고니스트의 제조 방법 |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| SG188361A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Non-hygroscopic salts of 5-ht2c agonists |
| US8999970B2 (en) | 2010-09-01 | 2015-04-07 | Arena Pharmaceuticals, Inc. | Administration of an anti-obesity compound to individuals with renal impairment |
| EP3485878A1 (de) | 2010-09-01 | 2019-05-22 | Arena Pharmaceuticals, Inc. | Darreichungsformen von 5-ht2c-agonisten, die nützlich für gewichtskontrolle sind |
| CA2886875A1 (en) | 2012-10-09 | 2014-04-17 | Arena Pharmaceuticals, Inc. | Method of weight management |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3393192A (en) * | 1965-04-26 | 1968-07-16 | Schering Corp | Novel benzazepines |
| US3609138A (en) * | 1967-12-22 | 1971-09-28 | Ciba Geigy Corp | 1-aryl-3-benzazepines |
| US4011319A (en) * | 1975-07-02 | 1977-03-08 | Smithkline Corporation | Pharmaceutical compositions and methods involving benzazepine derivatives |
| ZA792044B (en) * | 1978-05-08 | 1980-05-28 | Scherico Ltd | Substituted 1-phenyl-2,3,4,5-tetrahydro-1h-3-benzazepines,process for the preparation thereof,and pharmaceutical compositions containing them |
| US4284555A (en) * | 1979-04-27 | 1981-08-18 | Schering Corporation | 7-Chloro-8(substituted amino carbonyloxy)-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
| US4668685A (en) * | 1984-07-05 | 1987-05-26 | E.I. Du Pont De Nemours And Company | Substituted benzoate ester prodrug derivatives of 3-hydroxymorphinans, which are analgesics or narcotic antagonists |
| DK180485D0 (da) * | 1985-04-22 | 1985-04-23 | Novo Industri As | Nitrogenholdige forbindelser |
| ZA882080B (en) * | 1987-03-27 | 1989-04-26 | Schering Corp | Substituted benzazepines,their preparation and pharmaceutical compositions containing them |
-
1988
- 1988-03-01 DK DK107688A patent/DK107688D0/da not_active Application Discontinuation
-
1989
- 1989-02-07 IL IL89207A patent/IL89207A0/xx not_active IP Right Cessation
- 1989-02-10 IE IE42089A patent/IE64247B1/en not_active IP Right Cessation
- 1989-02-14 CA CA000590992A patent/CA1312863C/en not_active Expired - Fee Related
- 1989-02-20 PH PH38219A patent/PH26368A/en unknown
- 1989-02-22 FI FI890841A patent/FI94955C/fi not_active IP Right Cessation
- 1989-02-25 KR KR1019890002236A patent/KR0126473B1/ko not_active Expired - Fee Related
- 1989-02-27 NZ NZ228151A patent/NZ228151A/xx unknown
- 1989-02-28 DE DE89103531T patent/DE68909448T2/de not_active Expired - Fee Related
- 1989-02-28 NO NO890857A patent/NO173825C/no unknown
- 1989-02-28 ZA ZA891537A patent/ZA891537B/xx unknown
- 1989-02-28 US US07/317,016 patent/US5017571A/en not_active Expired - Fee Related
- 1989-02-28 ES ES89103531T patent/ES2059592T3/es not_active Expired - Lifetime
- 1989-02-28 EP EP89103531A patent/EP0331130B1/de not_active Expired - Lifetime
- 1989-02-28 AT AT89103531T patent/ATE95179T1/de not_active IP Right Cessation
- 1989-03-01 PT PT89887A patent/PT89887B/pt not_active IP Right Cessation
- 1989-03-01 JP JP1046695A patent/JPH01254679A/ja active Pending
- 1989-03-01 AU AU30907/89A patent/AU613716B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA1312863C (en) | 1993-01-19 |
| NZ228151A (en) | 1991-08-27 |
| NO173825B (no) | 1993-11-01 |
| NO890857D0 (no) | 1989-02-28 |
| ZA891537B (en) | 1989-11-29 |
| KR0126473B1 (ko) | 1997-12-24 |
| NO890857L (no) | 1989-09-04 |
| ES2059592T3 (es) | 1994-11-16 |
| ATE95179T1 (de) | 1993-10-15 |
| JPH01254679A (ja) | 1989-10-11 |
| NO173825C (no) | 1994-02-09 |
| IE890420L (en) | 1989-09-01 |
| US5017571A (en) | 1991-05-21 |
| DE68909448T2 (de) | 1994-02-10 |
| EP0331130B1 (de) | 1993-09-29 |
| AU613716B2 (en) | 1991-08-08 |
| KR890014494A (ko) | 1989-10-24 |
| DE68909448D1 (de) | 1993-11-04 |
| AU3090789A (en) | 1989-09-07 |
| FI94955B (fi) | 1995-08-15 |
| FI94955C (fi) | 1995-11-27 |
| EP0331130A1 (de) | 1989-09-06 |
| DK107688D0 (da) | 1988-03-01 |
| FI890841A7 (fi) | 1989-09-02 |
| FI890841A0 (fi) | 1989-02-22 |
| IL89207A0 (en) | 1989-09-10 |
| IE64247B1 (en) | 1995-07-26 |
| PT89887A (pt) | 1989-11-10 |
| PT89887B (pt) | 1994-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0331130B1 (de) | Carbaminsäureester von substituierten 7-Hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepinen | |
| US7528162B2 (en) | 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity | |
| DE69405624T2 (de) | Pharmazeutische Verbindungen | |
| KR100193928B1 (ko) | 피페라진 유도초체 및 이의 제조방법 | |
| Younes et al. | Synthesis and structure–activity relationships of novel arylalkyl 4-benzyl piperazine derivatives as σ site selective ligands | |
| EP0299493A2 (de) | N-[(2-Oxopyrrolidin-1-yl)acetyl]piperazin-Derivate und Arzneimittel gegen senile Dementia | |
| DE69431471T2 (de) | Amidderivate als 5-HT1A-Liganden | |
| PL168617B1 (pl) | Sposób wytwarzania nowych pochodnych 4-pirymidynonów PL PL | |
| CA2281607A1 (en) | Pharmaceutical formulations in dry form for the oral administration of a cyclic quaternary ammonium compound | |
| DE69805033T2 (de) | Tetrazolderivate als LTD4 und H1 Antagonisten | |
| US4851424A (en) | 1-Phenyl-lower alkyl-imidazole 4- or 5-carboxamide compounds which are useful in the treatment of epilepsy | |
| DE4427647A1 (de) | N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung | |
| CA2093771A1 (en) | Piperazine derivatives | |
| AU632362B2 (en) | Nmda antagonists | |
| JP4353684B2 (ja) | １−［１−（ヘテロ）アリール−１−ペルヒドロキシアルキルメチル］−ピペラジン化合物、その製法、薬学的組成物を製造するための該化合物の使用、および該化合物を製造するための出発化合物 | |
| KR100332325B1 (ko) | 이소프로필2-메톡시에틸4-(2-클로로-3-시아노-페닐)-1,4-디히디로-2,6-디메틸-피리딘-3,5-디카르복실레이트 | |
| JP6808088B2 (ja) | 純粋な５−ｈｔ６受容体アンタゴニストとしてのフルオロピペリジン化合物 | |
| EP0124630A1 (de) | Pyrimidin-Thioalkylpyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindung enthaltende Arzneimittel | |
| PL243119B1 (pl) | Rozpuszczalne w wodzie modyfikowane pochodne aminokwasowe nadające się do leczenia chorób o podłożu neurologicznym oraz zaburzeń psychiatrycznych | |
| RU2822464C2 (ru) | Ингибиторы аврора-киназы и их применение | |
| EP2773621B1 (de) | Verfahren zur herstellung einer kristallinen delta-form von ivabradinhydrochlorid | |
| US7173044B2 (en) | Imidazoline derivatives having CB1-antagonistic activity | |
| IE61100B1 (en) | Substituted pyrrolidinones | |
| Alaimo et al. | Synthesis and anti-inflammatory evaluation of 2-(substituted amino) quinolizinium bromides | |
| CA1210001A (en) | Semicarbazides, the preparation and use thereof |