NL9000627A - Werkwijze ter bereiding van nieuwe thienotriazolo-diazepines. - Google Patents
Werkwijze ter bereiding van nieuwe thienotriazolo-diazepines. Download PDFInfo
- Publication number
- NL9000627A NL9000627A NL9000627A NL9000627A NL9000627A NL 9000627 A NL9000627 A NL 9000627A NL 9000627 A NL9000627 A NL 9000627A NL 9000627 A NL9000627 A NL 9000627A NL 9000627 A NL9000627 A NL 9000627A
- Authority
- NL
- Netherlands
- Prior art keywords
- thieno
- diazepine
- pyrido
- chlorophenyl
- tetrahydro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000003586 protic polar solvent Substances 0.000 claims description 4
- 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 description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 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
- 230000008569 process Effects 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 45
- -1 2-chlorobenzovl Chemical class 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 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 29
- 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 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 206010006482 Bronchospasm Diseases 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000555745 Sciuridae Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 3
- AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 description 2
- MWMKSUVPEKGNPX-UHFFFAOYSA-N 1,4-diazepine-2-thione Chemical compound S=C1C=NC=CC=N1 MWMKSUVPEKGNPX-UHFFFAOYSA-N 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 102000004300 GABA-A Receptors Human genes 0.000 description 2
- 108090000839 GABA-A Receptors Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- SQOJOAFXDQDRGF-MMQTXUMRSA-N ginkgolide-b Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13[C@@H](O)[C@@H]1OC(=O)[C@@H](C)[C@]21O SQOJOAFXDQDRGF-MMQTXUMRSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- GVEAYVLWDAFXET-XGHATYIMSA-N pancuronium Chemical compound C[N+]1([C@@H]2[C@@H](OC(C)=O)C[C@@H]3CC[C@H]4[C@@H]5C[C@@H]([C@@H]([C@]5(CC[C@@H]4[C@@]3(C)C2)C)OC(=O)C)[N+]2(C)CCCCC2)CCCCC1 GVEAYVLWDAFXET-XGHATYIMSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 1
- DSEDVLWGAMXCRK-UHFFFAOYSA-N 14-(2-chlorophenyl)-11-hydrazinyl-N-(4-methoxyphenyl)-8-thia-5,10,13-triazatricyclo[7.5.0.02,7]tetradeca-1(9),2(7),10,13-tetraene-5-carbothioamide Chemical compound ClC1=C(C=CC=C1)C1=NCC(=NC2=C1C1=C(S2)CN(CC1)C(NC1=CC=C(C=C1)OC)=S)NN DSEDVLWGAMXCRK-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
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- CNPGUKSPKFNPRF-UHFFFAOYSA-M C1=CC2=CC=C(C=CC=C3C=C4)C3=C2C4=C1.[OH-].[K+] Chemical compound C1=CC2=CC=C(C=CC=C3C=C4)C3=C2C4=C1.[OH-].[K+] CNPGUKSPKFNPRF-UHFFFAOYSA-M 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108010003541 Platelet Activating Factor Proteins 0.000 description 1
- 230000010799 Receptor Interactions Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000012351 deprotecting agent Substances 0.000 description 1
- 125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940125695 gastrointestinal agent Drugs 0.000 description 1
- 239000004083 gastrointestinal agent Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 230000010807 negative regulation of binding Effects 0.000 description 1
- 210000000056 organ Anatomy 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
- 229960005457 pancuronium Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VKKMDKZVKMTEJG-UHFFFAOYSA-N thieno[2,3-e][1,4]diazepin-2-one Chemical compound O=C1C=NC=C2C=CSC2=N1 VKKMDKZVKMTEJG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9007001A GB2242427B (en) | 1990-03-29 | 1990-03-29 | Preparation of thieno-triazolo-diazepine derivatives |
| GB9007001 | 1990-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL9000627A true NL9000627A (nl) | 1991-10-16 |
Family
ID=10673450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9000627A NL9000627A (nl) | 1990-03-29 | 1990-03-19 | Werkwijze ter bereiding van nieuwe thienotriazolo-diazepines. |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU620230B2 (en, 2012) |
| BE (1) | BE1003697A3 (en, 2012) |
| CH (1) | CH680366A5 (en, 2012) |
| DE (1) | DE4010315C2 (en, 2012) |
| GB (1) | GB2242427B (en, 2012) |
| HK (1) | HK131793A (en, 2012) |
| NL (1) | NL9000627A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8907256D0 (en) * | 1989-03-31 | 1989-05-17 | Rech Et D Applic Scient Scras | New derivatives of hetrazepine as anti-asthmatic anti-allergic and gastro-intestinal protectors |
| FR2791980B1 (fr) | 1999-04-09 | 2001-07-06 | Sod Conseils Rech Applic | Pyrido-thieno-diazepines, leur procede de preparation, et les compositions pharmaceutiques les contenant |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0254245A1 (de) * | 1986-07-22 | 1988-01-27 | Boehringer Ingelheim Kg | Neue Hetrazepine und Verfahren zu ihrer Herstellung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3435973A1 (de) * | 1984-10-01 | 1986-04-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Diazepine enthaltende pharmazeutische zusammensetzungen mit paf-antagonistischer wirkung |
| DE3724031A1 (de) * | 1986-07-22 | 1988-01-28 | Boehringer Ingelheim Kg | Neue hetrazepine und verfahren zu ihrer herstellung |
-
1990
- 1990-03-19 NL NL9000627A patent/NL9000627A/nl active Search and Examination
- 1990-03-27 BE BE9000341A patent/BE1003697A3/fr not_active IP Right Cessation
- 1990-03-29 CH CH104590A patent/CH680366A5/fr not_active IP Right Cessation
- 1990-03-29 GB GB9007001A patent/GB2242427B/en not_active Expired - Fee Related
- 1990-03-30 DE DE19904010315 patent/DE4010315C2/de not_active Expired - Fee Related
- 1990-03-30 AU AU52423/90A patent/AU620230B2/en not_active Ceased
-
1993
- 1993-12-02 HK HK131793A patent/HK131793A/xx not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0254245A1 (de) * | 1986-07-22 | 1988-01-27 | Boehringer Ingelheim Kg | Neue Hetrazepine und Verfahren zu ihrer Herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4010315A1 (de) | 1991-10-02 |
| HK131793A (en) | 1993-12-10 |
| AU620230B2 (en) | 1992-02-13 |
| DE4010315C2 (de) | 2003-08-28 |
| GB2242427A (en) | 1991-10-02 |
| CH680366A5 (en, 2012) | 1992-08-14 |
| BE1003697A3 (fr) | 1992-05-26 |
| GB9007001D0 (en) | 1990-05-30 |
| GB2242427B (en) | 1993-05-12 |
| AU5242390A (en) | 1991-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI64594B (fi) | Foerfarande foer framstaellning av antiallergiska 3-(1h-tetrazol-5-yl)-4-pyrido(1,2-a)pyrimidin-4-onderivat | |
| CA1300148C (en) | 1,3-dihydro-6-(1-hydroxy-2-dimethylaminomethyl-allyl)-7- hydroxy-furo(3,4-c)-pyridine derivatives | |
| NL9000626A (nl) | Derivaten van thieno-triazolo-diazepine, werkwijze ter bereiding ervan en therapeutische samenstellingen, die deze bevatten. | |
| DE4015137C2 (de) | Thieno-triazolo-diazepinderivate, Verfahren ihrer Herstellung und diese enthaltende therapeutische Zusammensetzungen | |
| DK149816B (da) | Analogifremgangsmaade til fremstilling af tetrahydrothieno(3,2-c)pyridinderivater | |
| EP0318682A2 (de) | Tricyclische Thiazolderivate | |
| DE4010361C2 (de) | Sulfonylderivate von Thieno-triazolo-diazepinen, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Zusammensetzungen | |
| FI76810B (fi) | Foerfarande foer framstaellning av farmaceutiskt vaerdefulla tiazolo-tieno-azepin- och tiazolo-tieno-pyridinderivat. | |
| NL9000627A (nl) | Werkwijze ter bereiding van nieuwe thienotriazolo-diazepines. | |
| SU900813A3 (ru) | Способ получени производных тиенопиридина | |
| EP0025643B1 (en) | Oxo-pyrido(1,2-a)thienopyrimidine compounds, processes for their production, and pharmaceutical compositions containing said compounds | |
| CA2013516C (en) | Preparation process of new thieno-triazolo-diazepine | |
| IE900807A1 (en) | Preparation of thieno-triazolo-diazepine derivatives | |
| NO173140B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive tieno-triazolo-diazepin-derivater | |
| AT394562B (de) | Verfahren zur herstellung neuer thieno-triazolodiazepine | |
| FI95035B (fi) | Uusien tieno-triatsolo-diatsepiinien valmistusmenetelmä | |
| DE4015136A1 (de) | Verfahren zur herstellung von thieno-triazolo-diazepinderivaten | |
| FI93120C (fi) | Tieno-triatsolo-diatsepiinijohdosten valmistusmenetelmä | |
| NO173504B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive tieno-triazolo-diazepin-derivater | |
| JPH0686458B2 (ja) | 新規なチェノ‐トリアゾロ‐ジアゼピン誘導体の製造法 | |
| SE507189C3 (sv) | Framstaellningsfoerfarande foer nya tieno-triazolo-diazepin-foereningar | |
| FR2660311A1 (fr) | Procede de preparation des nouveaux derives de la thieno-triazolo-diazepine. | |
| IT9019885A1 (it) | Procedimento di preparazione di nuove tieno-triazolo-diazepine | |
| JPS5811877B2 (ja) | イコウカンカゴウブツ ノ セイゾウホウ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BN | A decision not to publish the application has become irrevocable |