CA2016550A1 - Procede de preparation de derives de thieno-triazolo-diazepine - Google Patents

Procede de preparation de derives de thieno-triazolo-diazepine

Info

Publication number: CA2016550A1
Authority: CA; Canada
Prior art keywords: thieno; diazepine; triazolo; formula; tetrahydro
Prior art date: 1990-05-09
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002016550A

Other languages

English (en)

Inventor

Jacques Pommier

Jean-Pierre Laurent

Andre Esanu

Pierre Braquet

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ipsen Pharma SAS

Original Assignee

Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS

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.)

1990-05-09

Filing date

1990-05-11

Publication date

1991-11-11

1990-05-09 Priority claimed from GB9010402A external-priority patent/GB2243829B/en

1990-05-11 Application filed by Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS filed Critical Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS

1990-05-11 Priority to CA002016550A priority Critical patent/CA2016550A1/fr

1991-11-11 Publication of CA2016550A1 publication Critical patent/CA2016550A1/fr

Status Abandoned legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 35
238000006243 chemical reaction Methods 0.000 claims abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 30
238000010992 reflux Methods 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 3
239000003586 protic polar solvent Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
CCDMBTCSHSROMD-UHFFFAOYSA-N 7h-thieno[3,2-c]diazepine Chemical class C1=CN=NC2=CCSC2=C1 CCDMBTCSHSROMD-UHFFFAOYSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
239000005864 Sulphur Substances 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 20
HNDGEYCCZGRMTN-UHFFFAOYSA-N thieno[3,2-f:4,5-f]bis[1]benzothiophene Chemical compound S1C2=CC=3SC=CC=3C=C2C2=C1C=C(SC=C1)C1=C2 HNDGEYCCZGRMTN-UHFFFAOYSA-N 0.000 description 20
FGNAJWFZOBYZLR-UHFFFAOYSA-N 3h-[1,2,4]triazolo[4,3-a][1,4]diazepine Chemical compound N1=CC=CN2CN=NC2=C1 FGNAJWFZOBYZLR-UHFFFAOYSA-N 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
229960004132 diethyl ether Drugs 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 7
AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
-1 diisopropyl acetate Chemical compound 0.000 description 6
238000005406 washing Methods 0.000 description 6
229940049706 benzodiazepine Drugs 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229940093499 ethyl acetate Drugs 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
FTHCMTYOZSIHJL-UHFFFAOYSA-N 2-propan-2-ylsulfanylacetic acid Chemical compound CC(C)SCC(O)=O FTHCMTYOZSIHJL-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
102000004300 GABA-A Receptors Human genes 0.000 description 2
108090000839 GABA-A Receptors Proteins 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000283977 Oryctolagus Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
238000000034 method Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000010792 warming Methods 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
IXQFVGCPQRXSRU-UHFFFAOYSA-N 1-[9-(2-chlorophenyl)-3-methyl-17-thia-2,4,5,8,14-pentazatetracyclo[8.7.0.02,6.011,16]heptadeca-1(10),3,5,8,11(16)-pentaen-14-yl]-2-(3,4,5-trimethoxyphenyl)sulfanylethanone Chemical compound COC1=C(OC)C(OC)=CC(SCC(=O)N2CC3=C(C4=C(N5C(C)=NN=C5CN=C4C=4C(=CC=CC=4)Cl)S3)CC2)=C1 IXQFVGCPQRXSRU-UHFFFAOYSA-N 0.000 description 1
PCVZUSQAEYZQJW-UHFFFAOYSA-N 1-[9-(2-chlorophenyl)-3-methyl-17-thia-2,4,5,8,14-pentazatetracyclo[8.7.0.02,6.011,16]heptadeca-1(10),3,5,8,11(16)-pentaen-14-yl]-2-(furan-2-ylsulfanyl)ethanethione Chemical compound C1C=2SC=3N4C(C)=NN=C4CN=C(C=4C(=CC=CC=4)Cl)C=3C=2CCN1C(=S)CSC1=CC=CO1 PCVZUSQAEYZQJW-UHFFFAOYSA-N 0.000 description 1
LKSZLTFXQYHHCU-UHFFFAOYSA-N 1-[9-(2-chlorophenyl)-3-methyl-17-thia-2,4,5,8,14-pentazatetracyclo[8.7.0.02,6.011,16]heptadeca-1(10),3,5,8,11(16)-pentaen-14-yl]-2-hexadecylsulfanylethanone Chemical compound C1N(C(=O)CSCCCCCCCCCCCCCCCC)CCC2=C1SC(N1C(C)=NN=C1CN=1)=C2C=1C1=CC=CC=C1Cl LKSZLTFXQYHHCU-UHFFFAOYSA-N 0.000 description 1
SHABTHGARXYERS-UHFFFAOYSA-N 14-(2-chlorophenyl)-5-(2-propan-2-ylsulfanylacetyl)-8-thia-5,10,13-triazatricyclo[7.5.0.02,7]tetradeca-1(9),2(7),13-trien-11-one Chemical compound ClC1=C(C=CC=C1)C1=NCC(NC2=C1C1=C(S2)CN(CC1)C(=O)CSC(C)C)=O SHABTHGARXYERS-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
ZHPHSPQOOZMDHC-UHFFFAOYSA-N 6 -(2-chlorophenyl)- 9-(isopropylthiomethyl-thiocarbonyl)-7,8,9,10-tetrahydro-1-methyl-4h-pyrido [4',3':4,5] thieno [3,2-f] 1,2,4-triazolo [4,3-a] 1,4-diazepine Chemical compound C1N(C(=S)CSC(C)C)CCC2=C1SC(N1C(C)=NN=C1CN=1)=C2C=1C1=CC=CC=C1Cl ZHPHSPQOOZMDHC-UHFFFAOYSA-N 0.000 description 1
OMXRYYPDXHPHQN-UHFFFAOYSA-N 7h-thieno[2,3-e][1,4]diazepine Chemical compound C1=CN=CC2=CCSC2=N1 OMXRYYPDXHPHQN-UHFFFAOYSA-N 0.000 description 1
241001514645 Agonis Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000566113 Branta sandvicensis Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
NZXKDOXHBHYTKP-UHFFFAOYSA-N Metohexital Chemical compound CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O NZXKDOXHBHYTKP-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
LMWOSJZNUGFJJB-UHFFFAOYSA-N O-ethyl 3-methylbutanethioate Chemical compound C(C)OC(CC(C)C)=S LMWOSJZNUGFJJB-UHFFFAOYSA-N 0.000 description 1
230000010799 Receptor Interactions Effects 0.000 description 1
241001247203 Syngnathidae Species 0.000 description 1
241000193803 Therea Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001088 anti-asthma Effects 0.000 description 1
230000002253 anti-ischaemic effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000000924 antiasthmatic agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000010908 decantation Methods 0.000 description 1
125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 description 1
230000000694 effects Effects 0.000 description 1
LUBGFMZTGFXIIN-UHFFFAOYSA-N ethyl 4-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)CC1 LUBGFMZTGFXIIN-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000003550 marker Substances 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000014786 phosphorus Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 1
230000001012 protector Effects 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
LZTYEEBQWUSNDU-UHFFFAOYSA-N thieno[2,3-e][1,4]diazepine-2-thione Chemical compound S=C1C=NC=C2C=CSC2=N1 LZTYEEBQWUSNDU-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CA002016550A 1990-05-09 1990-05-11 Procede de preparation de derives de thieno-triazolo-diazepine Abandoned CA2016550A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002016550A CA2016550A1 (fr)	1990-05-09	1990-05-11	Procede de preparation de derives de thieno-triazolo-diazepine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9010402A GB2243829B (en)	1990-05-09	1990-05-09	Preparation of thieno-triazolo-diazepine derivatives
CA002016550A CA2016550A1 (fr)	1990-05-09	1990-05-11	Procede de preparation de derives de thieno-triazolo-diazepine

Publications (1)

Publication Number	Publication Date
CA2016550A1 true CA2016550A1 (fr)	1991-11-11

Family

ID=25674130

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002016550A Abandoned CA2016550A1 (fr)	1990-05-09	1990-05-11	Procede de preparation de derives de thieno-triazolo-diazepine

Country Status (1)

Country	Link
CA (1)	CA2016550A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111533745A (zh) *	2020-05-20	2020-08-14	成都药明康德新药开发有限公司	叔丁基-3-(氨基甲基)二氢-5h-三唑并二氮杂卓-8(9h)-甲酸基酯制法

1990
- 1990-05-11 CA CA002016550A patent/CA2016550A1/fr not_active Abandoned

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111533745A (zh) *	2020-05-20	2020-08-14	成都药明康德新药开发有限公司	叔丁基-3-(氨基甲基)二氢-5h-三唑并二氮杂卓-8(9h)-甲酸基酯制法

Legal Events

Date	Code	Title	Description
1993-03-29	EEER	Examination request
1999-05-11	FZDE	Discontinued

Publication	Publication Date	Title
CA1238907A (fr)	1988-07-05	1,2,8,8a-tetrahydrocyclopropa¬c\|pyrrolo (3,2-e)-indol-4(5h)-ones et composes apparentes
CA2118171C (fr)	1999-12-28	Derives de la galanthamine, leur mode de preparation et leur utilisation comme medicaments
CA2016551C (fr)	1997-09-09	Derives de thieno-triazolo-diazepine, procede de preparation, et composes therapeutiques contenant lesdits derives
CA2013518C (fr)	2004-02-24	Derives de thieno-triazolo-diazepine, procede de preparation et composes therapeutiques les contenant
Vedachalam et al.	1991	Facile synthesis and nitration of cis-syn-cis-2, 6-dioxodecahydro-1H, 5H-diimidazo [4, 5-b: 4', 5'-e] pyrazine
CA2013519C (fr)	2004-02-24	Derives sulfonyl de thieno-triazolo-diazepine, procede de preparation et composes therapeutiques les contenant
CA2016550A1 (fr)	1991-11-11	Procede de preparation de derives de thieno-triazolo-diazepine
CA2513220A1 (fr)	2004-08-26	Derives de benzamide en tant qu'agonistes d'oxytocine et antagonistes de vasopressine
Esses‐Reiter et al.	1987	On triazoles. X. The reaction of 5‐amino‐1, 2, 4‐triazoles with tetrahydrothiophene β‐keto esters
AU620513B2 (en)	1992-02-20	Preparation process of thieno-triazolo-diazepine derivatives
IE901582A1 (en)	1991-11-06	Preparation of thieno-triazolo-diazepine derivatives
US5098919A (en)	1992-03-24	Pyrrolo(2,1-b)thiazole derivatives
NZ233573A (en)	1991-07-26	Preparation of thieno-triazolo-diazepine derivatives
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Daich et al.	1993	A novel practical synthesis of pyrrolo [1, 2‐a] thieno [2, 3‐e][1, 4] diazepines
NO173504B (no)	1993-09-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive tieno-triazolo-diazepin-derivater
FI93120C (fi)	1995-02-27	Tieno-triatsolo-diatsepiinijohdosten valmistusmenetelmä
Pongó et al.	1994	On triazoles. XXXIII. The reaction of potassium triazolyldithiocarbonates with dihaloalkanes
KR800000047B1 (ko)	1980-01-28	치환된 6-아릴-4H-S-트리아졸로-[3,4c]-티에노-[2,3e]-1,4-디아제핀의 제조방법
KR800001422B1 (ko)	1980-12-05	1-아실피페라진-4-카르복실산의 에스텔의 제조방법
Reiter et al.	1988	On triazoles XVI. The reaction of 5‐amino‐1, 2, 4‐triazoles with β‐and γ‐oxo esters. A novel N‐carbonylation reaction
Belanger et al.	1986	Synthesis of 2, 3, 4, 4a, 9, 9a-hexahydro-3, 9-methano-1 H-indeno [2, 1-c] pyridine and some N-substituted derivatives

CA2016550A1 - Procede de preparation de derives de thieno-triazolo-diazepine - Google Patents

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