SE436748B - Forfarande for framstellning av diazepinderivat - Google Patents

Forfarande for framstellning av diazepinderivat

Info

Publication number: SE436748B
Authority: SE; Sweden
Prior art keywords: formula; mol; benzodiazepine; carboxylic acid; lower alkyl
Prior art date: 1977-04-04

Application number

SE7803743A

Other languages

English (en)

Swedish (sv)

Other versions

SE7803743L (sv

Inventor

A Walser

Original Assignee

Hoffmann La Roche

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.)

1977-04-04

Filing date

1978-04-03

Publication date

1985-01-21

1978-04-03 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1978-10-05 Publication of SE7803743L publication Critical patent/SE7803743L/xx

1985-01-21 Publication of SE436748B publication Critical patent/SE436748B/sv

Links

238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 8
150000004908 diazepines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 18
-1 mono-substituted phenyl Chemical group 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
CFCNTIFLYGKEIO-UHFFFAOYSA-N 2-isocyanoacetic acid Chemical compound OC(=O)C[N+]#[C-] CFCNTIFLYGKEIO-UHFFFAOYSA-N 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
LJGKKJWPDGDDEH-UHFFFAOYSA-N ethyl 1H-1,2-benzodiazepine-3-carboxylate Chemical compound C(C)OC(=O)C1=NNC2=C(C=C1)C=CC=C2 LJGKKJWPDGDDEH-UHFFFAOYSA-N 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
BMGXAZCDDYTVFV-UHFFFAOYSA-N imidazo[4,5-c]diazepine Chemical class C1=CN=NC2=NC=NC2=C1 BMGXAZCDDYTVFV-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 2
240000006890 Erythroxylum coca Species 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
235000008957 cocaer Nutrition 0.000 claims 1
ZPUCINDJVBIVPJ-LJISPDSOSA-N ***e Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
239000000047 product Substances 0.000 description 8
FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 5
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
239000004157 Nitrosyl chloride Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 2
235000019392 nitrosyl chloride Nutrition 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
QQUIWIVTEWQHKA-UHFFFAOYSA-N 3h-1,4-benzodiazepine Chemical compound C1=NCC=NC2=CC=CC=C21 QQUIWIVTEWQHKA-UHFFFAOYSA-N 0.000 description 1
UBSKLVILVGEEON-UHFFFAOYSA-N 5-(2-fluorophenyl)-7-iodo-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(I)C=C12 UBSKLVILVGEEON-UHFFFAOYSA-N 0.000 description 1
KNGIGRDYBQPXKQ-UHFFFAOYSA-N 5-(2-fluorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1F KNGIGRDYBQPXKQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
BQZPYYPRLCXWDC-UHFFFAOYSA-N 8-chloro-4-(nitrosomethylamino)-1-phenyl-3h-1,5-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N=C(NCN=O)CC(=O)N1C1=CC=CC=C1 BQZPYYPRLCXWDC-UHFFFAOYSA-N 0.000 description 1
VMIYHDSEFNYJSL-UHFFFAOYSA-N Bromazepam Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=N1 VMIYHDSEFNYJSL-UHFFFAOYSA-N 0.000 description 1
CQPKTTUYSUFDLF-UHFFFAOYSA-N C12=CC(Cl)=CC=C2N=C(NCN=O)C[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Cl)=CC=C2N=C(NCN=O)C[N+]([O-])=C1C1=CC=CC=C1 CQPKTTUYSUFDLF-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
102100026450 POU domain, class 3, transcription factor 4 Human genes 0.000 description 1
101710133389 POU domain, class 3, transcription factor 4 Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
HAJABMGNYPPULO-UHFFFAOYSA-N acetic acid;isocyanic acid Chemical compound N=C=O.CC(O)=O HAJABMGNYPPULO-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
229940005530 anxiolytics Drugs 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
UVCOILFBWYKHHB-UHFFFAOYSA-N desalkylflurazepam Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 UVCOILFBWYKHHB-UHFFFAOYSA-N 0.000 description 1
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
MOYMDXWTHALRHV-UHFFFAOYSA-N ethyl 1H-1,4-benzodiazepine-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CNC2=CC=CC=C21 MOYMDXWTHALRHV-UHFFFAOYSA-N 0.000 description 1
GMHRKLCGOJTXJY-UHFFFAOYSA-N ethyl 1H-1-benzazepine-3-carboxylate Chemical compound C(C)OC(=O)C1=CNC2=C(C=C1)C=CC=C2 GMHRKLCGOJTXJY-UHFFFAOYSA-N 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
- H01L29/68—Types of semiconductor device ; Multistep manufacturing processes therefor controllable by only the electric current supplied, or only the electric potential applied, to an electrode which does not carry the current to be rectified, amplified or switched
- H01L29/76—Unipolar devices, e.g. field effect transistors
- H01L29/772—Field effect transistors
- H01L29/78—Field effect transistors with field effect produced by an insulated gate
- H01L29/7801—DMOS transistors, i.e. MISFETs with a channel accommodating body or base region adjoining a drain drift region
- H01L29/7802—Vertical DMOS transistors, i.e. VDMOS transistors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Power Engineering (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Neurology (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Microelectronics & Electronic Packaging (AREA)
Pain & Pain Management (AREA)
Computer Hardware Design (AREA)
Physics & Mathematics (AREA)
Ceramic Engineering (AREA)
Condensed Matter Physics & Semiconductors (AREA)
General Physics & Mathematics (AREA)
Physical Education & Sports Medicine (AREA)
Biomedical Technology (AREA)
Orthopedic Medicine & Surgery (AREA)
Neurosurgery (AREA)
Anesthesiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)

SE7803743A 1977-04-04 1978-04-03 Forfarande for framstellning av diazepinderivat SE436748B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/784,187 US4118386A (en)	1977-04-04	1977-04-04	Synthesis of imidazo[1,5-a]diazepine-3-carboxylates

Publications (2)

Publication Number	Publication Date
SE7803743L SE7803743L (sv)	1978-10-05
SE436748B true SE436748B (sv)	1985-01-21

Family

ID=25131618

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7803743A SE436748B (sv)	1977-04-04	1978-04-03	Forfarande for framstellning av diazepinderivat

Country Status (20)

Country	Link
US (1)	US4118386A (it)
JP (1)	JPS53124298A (it)
AT (1)	AT367055B (it)
BE (1)	BE865653A (it)
CA (1)	CA1090333A (it)
CH (1)	CH633799A5 (it)
DE (1)	DE2813549A1 (it)
DK (1)	DK152732C (it)
ES (1)	ES468501A1 (it)
FI (1)	FI63408C (it)
FR (1)	FR2386544A1 (it)
GB (1)	GB1553189A (it)
GR (1)	GR74031B (it)
HU (1)	HU182497B (it)
IT (1)	IT1094314B (it)
LU (1)	LU79363A1 (it)
NL (1)	NL7803585A (it)
NO (1)	NO148455C (it)
PT (1)	PT67865B (it)
SE (1)	SE436748B (it)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4280957A (en) *	1974-09-11	1981-07-28	Hoffmann-La Roche Inc.	Imidazodiazepines and processes therefor
US4226771A (en) *	1979-07-25	1980-10-07	Hoffmann-La Roche Inc.	1,2,5-Oxadiazino[5,4-a][1,4]benzodiazepine derivatives
CA1143728A (en) *	1979-10-04	1983-03-29	Max Gerecke	Imidazodiazepine derivatives
US4238610A (en) *	1979-12-20	1980-12-09	Hoffmann-La Roche Inc.	Intermediates for the production of imidazobenzodiazepines
CA1185602A (en) *	1981-02-27	1985-04-16	Emilio Kyburz	Imidazodiazepines
CA1174673A (en) *	1981-02-27	1984-09-18	Walter Hunkeler	Imidazodiazepines
CA1184175A (en) *	1981-02-27	1985-03-19	Walter Hunkeler	Imidazodiazepines
US4352817A (en) *	1981-02-27	1982-10-05	Hoffmann-La Roche Inc.	Imidazo-diazepines and their use
DK476885D0 (da) *	1985-10-17	1985-10-17	Ferrosan As	Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf
PH30676A (en) *	1986-07-22	1997-09-16	Boehringer Ingelhein Kg	Hetrazepine compounds which have useful pharmaceutical utility
US5317018A (en) *	1992-06-09	1994-05-31	Armin Walser	Benzodiazepines and compositions for treating anxiety and panic disorders, and idiopathic and psychomotor epilepsy
US5670640A (en) *	1996-02-02	1997-09-23	Hoffmann-La Roche Inc.	Process for the manufacture of imidazodiazepine derivatives
GB2328940B (en) *	1997-09-05	1999-12-08	Dong Kook Pharm Co Ltd	A process for preparing benzodiazepine derivatives
AP2006003768A0 (en)	2004-05-25	2006-10-31	Pfizer Prod Inc	TetraazabenzoÄeÜazulene derivatives and analogs tehereof
US7960376B2 (en) *	2007-09-14	2011-06-14	Cara Therapeutics, Inc.	Benzo-fused heterocycles

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2984666A (en) *	1958-06-18	1961-05-16	Rohm & Haas	Condensed heterocyclic nitriles
BE787251A (fr) *	1971-08-04	1973-02-05	Upjohn Co	Nouvelles benzodiazepines et leur preparation
DE2318673A1 (de) *	1973-04-13	1974-11-07	Boehringer Sohn Ingelheim	Neue substituierte triazolo-1,5benzodiazepine
SE7509022L (sv) *	1974-09-09	1976-03-10	Du Pont	Foreningar med analgetisk verkan
US3920687A (en) *	1974-09-09	1975-11-18	American Home Prod	2,3,6,7-tetrahydro-6-phenyl-5h-imidazo(1,2-d)+8 1,4)benzodiazepin-5-ones and diazepines
ZA755418B (en) *	1974-09-11	1977-06-29	Hoffmann La Roche	Diazepine derivatives
IL49161A (en) *	1975-08-07	1982-04-30	Sparamedica Ag	Imidazo(1,5-a)(1,4)-diazepine derivatives,their manufacture and pharmaceutical compositions containing them
AT361486B (de) *	1975-08-07	1981-03-10	Hoffmann La Roche	Verfahren zur herstellung von neuen imidazo(1,5 -a) (1,4)diazepinverbindungen, ihren salzen und optisch aktiven formen
BE839365R (fr) *	1976-03-09	1976-09-09		Derives de diazepine
US4080323A (en) *	1977-03-07	1978-03-21	Hoffmann-La Roche Inc.	Imidazo [1,5-a][1,5] benzodiazepines

1977
- 1977-04-04 US US05/784,187 patent/US4118386A/en not_active Expired - Lifetime
1978
- 1978-03-28 CH CH328878A patent/CH633799A5/de not_active IP Right Cessation
- 1978-03-29 DE DE19782813549 patent/DE2813549A1/de not_active Ceased
- 1978-04-01 HU HU78HO2062A patent/HU182497B/hu unknown
- 1978-04-01 GR GR55858A patent/GR74031B/el unknown
- 1978-04-03 ES ES468501A patent/ES468501A1/es not_active Expired
- 1978-04-03 DK DK147378A patent/DK152732C/da not_active IP Right Cessation
- 1978-04-03 GB GB12929/78A patent/GB1553189A/en not_active Expired
- 1978-04-03 PT PT67865A patent/PT67865B/pt unknown
- 1978-04-03 LU LU79363A patent/LU79363A1/de unknown
- 1978-04-03 FI FI781010A patent/FI63408C/fi not_active IP Right Cessation
- 1978-04-03 CA CA300,285A patent/CA1090333A/en not_active Expired
- 1978-04-03 FR FR7809753A patent/FR2386544A1/fr active Granted
- 1978-04-03 AT AT0232978A patent/AT367055B/de not_active IP Right Cessation
- 1978-04-03 SE SE7803743A patent/SE436748B/sv not_active IP Right Cessation
- 1978-04-03 NO NO781168A patent/NO148455C/no unknown
- 1978-04-04 JP JP3889278A patent/JPS53124298A/ja active Granted
- 1978-04-04 NL NL7803585A patent/NL7803585A/xx not_active Application Discontinuation
- 1978-04-04 IT IT21967/78A patent/IT1094314B/it active
- 1978-04-04 BE BE186532A patent/BE865653A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH633799A5 (de)	1982-12-31
NO148455B (no)	1983-07-04
IT1094314B (it)	1985-07-26
FI781010A (fi)	1978-10-05
SE7803743L (sv)	1978-10-05
PT67865B (en)	1980-04-07
FI63408C (fi)	1983-06-10
FR2386544A1 (fr)	1978-11-03
NL7803585A (nl)	1978-10-06
CA1090333A (en)	1980-11-25
BE865653A (fr)	1978-10-04
LU79363A1 (de)	1979-05-25
NO781168L (no)	1978-10-05
GB1553189A (en)	1979-09-19
JPS6365673B2 (it)	1988-12-16
ES468501A1 (es)	1978-11-16
DK147378A (da)	1978-10-05
FI63408B (fi)	1983-02-28
IT7821967A0 (it)	1978-04-04
DK152732B (da)	1988-05-02
DK152732C (da)	1988-10-03
PT67865A (en)	1978-05-01
HU182497B (en)	1984-01-30
JPS53124298A (en)	1978-10-30
AT367055B (de)	1982-05-25
ATA232978A (de)	1981-10-15
US4118386A (en)	1978-10-03
FR2386544B1 (it)	1980-07-25
NO148455C (no)	1983-10-12
GR74031B (it)	1984-06-06
DE2813549A1 (de)	1978-10-05

Legal Events

Date

Code

Title

Description

1995-01-31

NUG

Patent has lapsed

Ref document number: 7803743-9

Effective date: 19900411

Format of ref document f/p: F

Publication	Publication Date	Title
SE436748B (sv)	1985-01-21	Forfarande for framstellning av diazepinderivat
CA1067491A (en)	1979-12-04	Diazepine derivatives
CH632511A5 (de)	1982-10-15	Verfahren zur herstellung von diazepinderivaten.
US3957783A (en)	1976-05-18	Thieno[2,3-d]pyrimidine derivatives
HU182662B (en)	1984-02-28	Process for producing pyrimido-2-benzodiazepine derivatives
US4201712A (en)	1980-05-06	Process for preparation of 6-aryl-4H-s-triazolo-[3,4-c]-thieno-[2,3-e]-1,4-diazepines
Potts et al.	1980	Reactions of (chlorocarbonyl) phenylketene. Formation of ring-fused 4H-1, 3-thiazinium betaines from heterocyclic thiones
US4116956A (en)	1978-09-26	Benzodiazepine derivatives
Pilli et al.	1983	Reaction of N-(p-tolylsulfonyl) diphenylcyclopropenimine with pyridinium and isoquinolinium ylides
Harrison et al.	1977	Novel fused‐ring derivatives of 2‐methyl‐3‐o‐tolyl‐4 (3H) quinazolone; Quinazolino [3, 2‐a][1, 4] benzodiazepines
Xu et al.	2001	Synthesis of 1, 3, 3a, 5‐tetraaryl‐3a, 4, 5, 6‐tetrahydro‐3H‐1, 2, 4‐triazolo [4, 3‐a][1, 5] benzodiazepines
KR810000782B1 (ko)	1981-07-06	디아제핀 유도체의 제조방법
US4075221A (en)	1978-02-21	Process for preparing triazolobenzodiazepines
CA1327572C (en)	1994-03-08	Imidazodiazepine derivatives
NATSUGARI et al.	1979	Heterocycles. XII. Synthesis of 2-Amino-5-phenyl-1, 4-benzodiazepine 1-Oxides and 2-Amino-6-phenyl-1, 5-benzodiazocine 1-Oxides and Their Reactions with Acylating Agents
Moffett et al.	1979	Central nervous system depressants. 15. 1, 4‐benzodiazepines
Kobayashi	1975	Pyrimidine-Fused 1, 4-Benzodiazepines. Reaction of 1, 4-Benzodiazepines with Formamide–POCl 3
US4335042A (en)	1982-06-15	Process to produce imidazobenzodiazepine intermediates
KR800001104B1 (ko)	1980-10-08	디아제핀 유도체의 제조방법
Potts et al.	1981	Nonclassical heteropentalenes containing the selenodiazole, thiatriazole and selenotriazole ring systems
KR800001105B1 (ko)	1980-10-08	디아제핀 유도체의 제조방법
US3838116A (en)	1974-09-24	Process for preparing 1,4-benzodiazepines
CA1055491A (en)	1979-05-29	Process for the manufacture of benzodiazepine derivatives
HU189631B (en)	1986-07-28	Process for preparing imidazodiazepine derivatives
CA1151645A (en)	1983-08-09	4-aryl-5,6,7,8-tetrahydropyrazolo(3,4-b)- (1,5)diazepine-1h,4h-5,7-diones and medicaments containing same