DK141965B - Analogifremgangsmåde til fremstilling af s-triazolo(4,3-a) (1,4)benzodiazepinderivater eller N-oxider eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af s-triazolo(4,3-a) (1,4)benzodiazepinderivater eller N-oxider eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK141965B DK141965B DK169972AA DK169972A DK141965B DK 141965 B DK141965 B DK 141965B DK 169972A A DK169972A A DK 169972AA DK 169972 A DK169972 A DK 169972A DK 141965 B DK141965 B DK 141965B
- Authority
- DK
- Denmark
- Prior art keywords
- chloro
- benzodiazepine
- triazolo
- general formula
- phenyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 5
- LGNWUMGEJQAWQD-UHFFFAOYSA-N 1h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical class N1=CC2=CC=CC=C2N2CN=NC2=C1 LGNWUMGEJQAWQD-UHFFFAOYSA-N 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title description 7
- 150000001204 N-oxides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 150000007522 mineralic acids Chemical class 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- NLGCACTXWVUTOZ-UHFFFAOYSA-N 1-(diethoxymethyl)-1,4-benzodiazepine Chemical compound C(C)OC(N1C=CN=CC2=C1C=CC=C2)OCC NLGCACTXWVUTOZ-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
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- 239000001257 hydrogen Substances 0.000 claims description 4
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- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
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- 238000003756 stirring Methods 0.000 claims description 2
- CFTYPCIFJCQYQI-UHFFFAOYSA-N 8-chloro-1-(diethoxymethyl)-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine;perchloric acid Chemical compound OCl(=O)(=O)=O.C12=CC(Cl)=CC=C2N2C(C(OCC)OCC)=NN=C2CN=C1C1=CC=CC=C1 CFTYPCIFJCQYQI-UHFFFAOYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- 238000007792 addition Methods 0.000 description 12
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- 239000002904 solvent Substances 0.000 description 8
- VWDCSWQCRXYZKN-UHFFFAOYSA-N 2,2-diethoxyacetohydrazide Chemical compound CCOC(OCC)C(=O)NN VWDCSWQCRXYZKN-UHFFFAOYSA-N 0.000 description 7
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- 241000699670 Mus sp. Species 0.000 description 6
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- 229940093915 gynecological organic acid Drugs 0.000 description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000001773 anti-convulsant effect Effects 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 208000007101 Muscle Cramp Diseases 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YOHJKBKLWJAEHF-UHFFFAOYSA-N 7-chloro-2-methylsulfanyl-5-phenyl-3h-1,4-benzodiazepine Chemical compound N=1CC(SC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 YOHJKBKLWJAEHF-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GWSXDWFXNVOIIC-UHFFFAOYSA-N (7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)hydrazine Chemical compound N=1CC(NN)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 GWSXDWFXNVOIIC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LSGVRDCZPXJXLH-UHFFFAOYSA-N 2,2-dimethoxyacetohydrazide Chemical compound COC(OC)C(=O)NN LSGVRDCZPXJXLH-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- WTGRHCXBHHGMEC-UHFFFAOYSA-N 2-methylsulfanyl-5-phenyl-3h-1,4-benzodiazepine Chemical class N=1CC(SC)=NC2=CC=CC=C2C=1C1=CC=CC=C1 WTGRHCXBHHGMEC-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- ZGTBVQNRHXJPFO-UHFFFAOYSA-N 8-chloro-1-(diethoxymethyl)-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(C(OCC)OCC)=NN=C2CN=C1C1=CC=CC=C1 ZGTBVQNRHXJPFO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 125000003282 alkyl amino group Chemical group 0.000 description 2
- ZURUZYHEEMDQBU-UHFFFAOYSA-N alpha-Hydroxyalprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(CO)=NN=C2CN=C1C1=CC=CC=C1 ZURUZYHEEMDQBU-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
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- 229960003965 antiepileptics Drugs 0.000 description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
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- CBKIDHHLDJSTJB-UHFFFAOYSA-N 1,2-benzodiazepine-1-carbaldehyde Chemical compound O=CN1N=CC=CC2=CC=CC=C12 CBKIDHHLDJSTJB-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- ZREYVPMKMCBAHA-UHFFFAOYSA-N 1-(phenylmethoxymethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical class N=1N=C2CN=CC3=CC=CC=C3N2C=1COCC1=CC=CC=C1 ZREYVPMKMCBAHA-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- KYGYCAUNXCVLQM-UHFFFAOYSA-N 2-phenylmethoxyacetohydrazide Chemical compound NNC(=O)COCC1=CC=CC=C1 KYGYCAUNXCVLQM-UHFFFAOYSA-N 0.000 description 1
- JJGOKKJJABVGSE-UHFFFAOYSA-N 4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-ylmethanol Chemical class C1N=CC2=CC=CC=C2N2C(CO)=NN=C21 JJGOKKJJABVGSE-UHFFFAOYSA-N 0.000 description 1
- DXAIBZTWPCDCFJ-UHFFFAOYSA-N 5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound ClC1=CC=CC=C1C1=NCC(=O)NC2=CC=CC=C12 DXAIBZTWPCDCFJ-UHFFFAOYSA-N 0.000 description 1
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- LZANARFQFSEWHV-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione Chemical class C12=CC=CC=C2NC(=S)CN=C1C1=CC=CC=C1 LZANARFQFSEWHV-UHFFFAOYSA-N 0.000 description 1
- MDPJHNGFYGSHME-UHFFFAOYSA-N 5-phenyl-2,3-dihydro-1h-1,4-benzodiazepine Chemical class C12=CC=CC=C2NCCN=C1C1=CC=CC=C1 MDPJHNGFYGSHME-UHFFFAOYSA-N 0.000 description 1
- LVPQJOJIXCTKPS-UHFFFAOYSA-N 6-(2-chlorophenyl)-1-(diethoxymethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC=CC=C2N2C(C(OCC)OCC)=NN=C2CN=C1C1=CC=CC=C1Cl LVPQJOJIXCTKPS-UHFFFAOYSA-N 0.000 description 1
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- MNGCQEMMIWVWSY-UHFFFAOYSA-N 8-chloro-1-(diethoxymethyl)-6-(2-fluorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(C(OCC)OCC)=NN=C2CN=C1C1=CC=CC=C1F MNGCQEMMIWVWSY-UHFFFAOYSA-N 0.000 description 1
- DERAXXGTLFTNJF-UHFFFAOYSA-N 8-chloro-1-(dimethoxymethyl)-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(C(OC)OC)=NN=C2CN=C1C1=CC=CC=C1 DERAXXGTLFTNJF-UHFFFAOYSA-N 0.000 description 1
- PHYRUGZQWLGZLY-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-1-(diethoxymethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(C(OCC)OCC)=NN=C2CN=C1C1=CC=CC=C1Cl PHYRUGZQWLGZLY-UHFFFAOYSA-N 0.000 description 1
- FUZGDDHPTYNOIM-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-1-carbaldehyde Chemical compound C=1C(Cl)=CC=C(N2C(C=O)=NN=C2CN=2)C=1C=2C1=CC=CC=C1Cl FUZGDDHPTYNOIM-UHFFFAOYSA-N 0.000 description 1
- CNXMBTJLZMMNHE-UHFFFAOYSA-N 8-chloro-6-phenyl-1-(phenylmethoxymethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Cl)=CC=C(N23)C=1C(C=1C=CC=CC=1)=NCC3=NN=C2COCC1=CC=CC=C1 CNXMBTJLZMMNHE-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XJQDSZGDDUJVHC-UHFFFAOYSA-N chlorobenzene;ethanol Chemical compound CCO.ClC1=CC=CC=C1 XJQDSZGDDUJVHC-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- XCLBIKIQSCTANZ-UHFFFAOYSA-N ethyl 2,2-diethoxyacetate Chemical compound CCOC(OCC)C(=O)OCC XCLBIKIQSCTANZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH523371 | 1971-04-08 | ||
| CH523371 | 1971-04-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141965B true DK141965B (da) | 1980-07-28 |
| DK141965C DK141965C (enrdf_load_stackoverflow) | 1980-12-08 |
Family
ID=4290168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK169972AA DK141965B (da) | 1971-04-08 | 1972-04-07 | Analogifremgangsmåde til fremstilling af s-triazolo(4,3-a) (1,4)benzodiazepinderivater eller N-oxider eller syreadditionssalte deraf. |
Country Status (24)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH572056A5 (enrdf_load_stackoverflow) * | 1972-11-28 | 1976-01-30 | Ciba Geigy Ag |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987052A (en) * | 1969-03-17 | 1976-10-19 | The Upjohn Company | 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| BE759099A (fr) * | 1969-11-18 | 1971-04-30 | Takeda Chemical Industries Ltd | Procede de fabrication de composes heterocycliques |
| US3681343A (en) * | 1971-05-11 | 1972-08-01 | Upjohn Co | 6-phenyl-s-triazolo{8 4,3-a{9 {8 1,4{9 {0 benzodiazepines |
-
1971
- 1971-04-08 CH CH1212973A patent/CH545302A/de not_active IP Right Cessation
-
1972
- 1972-03-20 ZA ZA721896A patent/ZA721896B/xx unknown
- 1972-03-21 IL IL39051A patent/IL39051A/xx unknown
- 1972-03-27 SE SE7203938A patent/SE413408B/xx unknown
- 1972-03-28 IE IE404/72A patent/IE36231B1/xx unknown
- 1972-03-29 FI FI720882A patent/FI52583C/fi active
- 1972-03-30 US US239780A patent/US3867536A/en not_active Expired - Lifetime
- 1972-03-30 CA CA138,606A patent/CA991639A/en not_active Expired
- 1972-04-01 DE DE19722215939 patent/DE2215939A1/de not_active Withdrawn
- 1972-04-05 GB GB1570272A patent/GB1392327A/en not_active Expired
- 1972-04-06 AU AU40820/72A patent/AU472767B2/en not_active Expired
- 1972-04-06 NO NO1163/72A patent/NO134839C/no unknown
- 1972-04-06 HU HUCI1223A patent/HU165318B/hu unknown
- 1972-04-06 DD DD162097A patent/DD97655A5/xx unknown
- 1972-04-07 PL PL1972154657A patent/PL83566B1/pl unknown
- 1972-04-07 CS CS435A patent/CS178449B2/cs unknown
- 1972-04-07 NL NL7204700A patent/NL7204700A/xx not_active Application Discontinuation
- 1972-04-07 CS CS2330A patent/CS178406B2/cs unknown
- 1972-04-07 AT AT302172A patent/AT317222B/de not_active IP Right Cessation
- 1972-04-07 AR AR241356A patent/AR193382A1/es active
- 1972-04-07 DK DK169972AA patent/DK141965B/da unknown
- 1972-04-07 BE BE781816A patent/BE781816A/xx unknown
- 1972-04-07 CS CS434A patent/CS178448B2/cs unknown
- 1972-04-07 AT AT781173A patent/AT317230B/de not_active IP Right Cessation
- 1972-04-07 FR FR7212299A patent/FR2132767B1/fr not_active Expired
- 1972-04-07 SU SU1771052A patent/SU499808A3/ru active
- 1972-04-08 JP JP3486172A patent/JPS5614671B1/ja active Pending
-
1973
- 1973-03-26 AR AR247234A patent/AR193942A1/es active
- 1973-03-26 AR AR247235A patent/AR194991A1/es active
- 1973-10-23 SU SU1964147A patent/SU482045A3/ru active
- 1973-10-23 SU SU1964148A patent/SU489332A3/ru active
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