DE2531677A1 - Neue thieno-4,1-oxazepine und verfahren zu ihrer herstellung - Google Patents
Neue thieno-4,1-oxazepine und verfahren zu ihrer herstellungInfo
- Publication number
- DE2531677A1 DE2531677A1 DE19752531677 DE2531677A DE2531677A1 DE 2531677 A1 DE2531677 A1 DE 2531677A1 DE 19752531677 DE19752531677 DE 19752531677 DE 2531677 A DE2531677 A DE 2531677A DE 2531677 A1 DE2531677 A1 DE 2531677A1
- Authority
- DE
- Germany
- Prior art keywords
- thieno
- general formula
- halogen
- triazolo
- different
- Prior art date
- 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.)
- Pending
Links
- 239000001961 anticonvulsive agent Substances 0.000 title abstract description 3
- 239000002249 anxiolytic agent Substances 0.000 title abstract description 3
- 230000000949 anxiolytic effect Effects 0.000 title abstract description 3
- 229940125681 anticonvulsant agent Drugs 0.000 title abstract 2
- 229940005530 anxiolytics Drugs 0.000 title abstract 2
- -1 thienyl acetamides Chemical class 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical class 0.000 abstract description 5
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000003091 serenic agent Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- LRZCHOZJGIXTRX-UHFFFAOYSA-N (2-aminophenyl)-thiophen-2-ylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CS1 LRZCHOZJGIXTRX-UHFFFAOYSA-N 0.000 description 1
- FXIWBCKGWTXJEJ-UHFFFAOYSA-N 2-chloro-n-[3-(2-chlorobenzoyl)thiophen-2-yl]acetamide Chemical compound S1C=CC(C(=O)C=2C(=CC=CC=2)Cl)=C1NC(=O)CCl FXIWBCKGWTXJEJ-UHFFFAOYSA-N 0.000 description 1
- YAGNKIVRNNJVQI-UHFFFAOYSA-N 2-chloro-n-[3-[(2-chlorophenyl)-hydroxymethyl]thiophen-2-yl]acetamide Chemical compound C=1C=CC=C(Cl)C=1C(O)C=1C=CSC=1NC(=O)CCl YAGNKIVRNNJVQI-UHFFFAOYSA-N 0.000 description 1
- BBBPUTKOKSMZSN-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)thieno[3,2-f][1,4]oxazepine 8-oxide Chemical compound ClC1=CC=CC=C1C1=NC=COC2=C1C=C(Br)S2=O BBBPUTKOKSMZSN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 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 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000002936 tranquilizing effect 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
- C07D495/02—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 two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752531677 DE2531677A1 (de) | 1975-07-16 | 1975-07-16 | Neue thieno-4,1-oxazepine und verfahren zu ihrer herstellung |
| JP50124860A JPS5212189A (en) | 1975-07-16 | 1975-10-16 | Production of novel thienoo 4*11oxezapines |
| AT460276A AT352733B (de) | 1975-07-16 | 1976-06-24 | Verfahren zur herstellung neuer thieno-4,1- oxazepine |
| FI761914A FI64161C (fi) | 1975-07-16 | 1976-07-01 | Nya substituerade 5-fenyl-tieno-(2,3-e)-1,4-oxazepinon-(1)-er som aer mellanprodukter vid framstaellning av farmakologisktvaerdefull 6-fenyl-4h-s-triazolo-(3,4-c)-tieno-(2,3-e)-1, 4-iazepin samt foerfarande foer deras framstaellning |
| RO7686908A RO76083A (ro) | 1975-07-16 | 1976-07-09 | Procedeu de preparare a 6-aril-4h-s-triazolo-/3,4-c/-tieno-/2,3-c/-1,4-diazepine |
| GR51234A GR60819B (en) | 1975-07-16 | 1976-07-10 | Preparation process of 6-aryl-4h-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepins |
| IL50032A IL50032A (en) | 1975-07-16 | 1976-07-13 | Preparation of 6-aryl-4h-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepines and novel intermediates used therefor |
| CH901976A CH627181A5 (en) | 1975-07-16 | 1976-07-14 | Process for the preparation of substituted 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e]-1,4-diazepines |
| LU75384A LU75384A1 (enrdf_load_stackoverflow) | 1975-07-16 | 1976-07-14 | |
| DD193857A DD126744A5 (enrdf_load_stackoverflow) | 1975-07-16 | 1976-07-14 | |
| BG033745A BG25227A3 (en) | 1975-07-16 | 1976-07-14 | A method of obtaining substituted 6-aryl-4h-s-threeazol-(3,4-c)-thiene-(2,3-e)-1,4-diazepines |
| AU15913/76A AU506140B2 (en) | 1975-07-16 | 1976-07-15 | Substituted 6-aryl 4H-S-triazolo-(3,4-C)-thieno-(2,3-E)1, 4-diazapines |
| MX761774U MX4246E (es) | 1975-07-16 | 1976-07-15 | Procedimiento para la preparacion de 6-aril-4h-s-triazolo-(3,4-c)-tieno=(2,3-e)-1,4-diazepinas sustituidas |
| SE7608112A SE421210B (sv) | 1975-07-16 | 1976-07-15 | Nya tieno-4,1-oxazepiner till anvendning som mellanprodukter for framstellning av substituerade tieno-triazolo-1,4-diazepiner och forfarande for framstellning derav |
| PL1976210914A PL111564B1 (en) | 1975-07-16 | 1976-07-15 | Process for preparing novel thieno-4,1-oxazepins |
| PT65374A PT65374B (de) | 1975-07-16 | 1976-07-15 | Verfahren zur herstellung von substituierte 6-aryl-4h-s-triazolo-/3,4-c/-thieno-/2,3-e/-1,4-diazepinen |
| BE168950A BE844170A (fr) | 1975-07-16 | 1976-07-15 | Procede de preparation de 6-aryl-4h-s-triazolo(3,4-c)-thieno-(2,3-e)-1,4-diazepines substituees |
| NLAANVRAGE7607871,A NL186008C (nl) | 1975-07-16 | 1976-07-15 | Werkwijze voor de bereiding van thieno-4,1-oxazepinen. |
| DK321376A DK321376A (da) | 1975-07-16 | 1976-07-15 | Thieno-4,1-oxazepiner og fremgangsmade til deres fremstilling |
| ZA00764212A ZA764212B (en) | 1975-07-16 | 1976-07-15 | Improvements relating to substituted 6-aryl-4h-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepines and intermediates |
| YU1753/76A YU40458B (en) | 1975-07-16 | 1976-07-15 | Process for preparing subst.6-aryl-4h-s-triazolo-(3,4-c)thieno-(2,3-e)-1,4-diazepines |
| CA257,092A CA1077475A (en) | 1975-07-16 | 1976-07-15 | Process for production of substituted 6-aryl-4h-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepines and intermediates |
| NO762473A NO148886C (no) | 1975-07-16 | 1976-07-15 | Nye tieno-4,1-oksazepiner og fremgangsmaate til fremstilling derav. |
| ES449849A ES449849A1 (es) | 1975-07-16 | 1976-07-15 | Procedimiento para la preparacion de 6-aril-4h-s-triazolo- (3,4-c)-tiene-(2,3-e)-1,4-diazepinas sustituidas. |
| GB1478478A GB1550680A (en) | 1975-07-16 | 1976-07-15 | 5-aryl-thieno-(2,3-e)-4,1-oxazepin-2-ones |
| HU70CA00000291A HU172620B (hu) | 1975-07-16 | 1976-07-16 | Sposob poluchenija 6-aril-4h-tieno-skobka-3,2-f-skobka zakryta-s-triazolo-skobka-4,3-a-skobka-1,4-skobka zakryta-diazepinov |
| FR7621836A FR2318165A1 (fr) | 1975-07-16 | 1976-07-16 | Procede de preparation de 6-aryl-4h-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepines substituees |
| IE1583/76A IE43694B1 (en) | 1975-07-16 | 1976-07-16 | Thieno-4,1-oxazepinones |
| US05/783,143 US4201712A (en) | 1975-07-16 | 1977-03-31 | Process for preparation of 6-aryl-4H-s-triazolo-[3,4-c]-thieno-[2,3-e]-1,4-diazepines |
| CH327381A CH630630A5 (en) | 1975-07-16 | 1981-05-19 | Processes for preparing substituted 6-aryl-4H-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepines. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752531677 DE2531677A1 (de) | 1975-07-16 | 1975-07-16 | Neue thieno-4,1-oxazepine und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2531677A1 true DE2531677A1 (de) | 1977-02-03 |
Family
ID=5951593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752531677 Pending DE2531677A1 (de) | 1975-07-16 | 1975-07-16 | Neue thieno-4,1-oxazepine und verfahren zu ihrer herstellung |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5212189A (enrdf_load_stackoverflow) |
| AT (1) | AT352733B (enrdf_load_stackoverflow) |
| BE (1) | BE844170A (enrdf_load_stackoverflow) |
| DE (1) | DE2531677A1 (enrdf_load_stackoverflow) |
| DK (1) | DK321376A (enrdf_load_stackoverflow) |
| FI (1) | FI64161C (enrdf_load_stackoverflow) |
| NO (1) | NO148886C (enrdf_load_stackoverflow) |
| PL (1) | PL111564B1 (enrdf_load_stackoverflow) |
| SE (1) | SE421210B (enrdf_load_stackoverflow) |
| ZA (1) | ZA764212B (enrdf_load_stackoverflow) |
-
1975
- 1975-07-16 DE DE19752531677 patent/DE2531677A1/de active Pending
- 1975-10-16 JP JP50124860A patent/JPS5212189A/ja active Pending
-
1976
- 1976-06-24 AT AT460276A patent/AT352733B/de not_active IP Right Cessation
- 1976-07-01 FI FI761914A patent/FI64161C/fi not_active IP Right Cessation
- 1976-07-15 NO NO762473A patent/NO148886C/no unknown
- 1976-07-15 PL PL1976210914A patent/PL111564B1/pl unknown
- 1976-07-15 ZA ZA00764212A patent/ZA764212B/xx unknown
- 1976-07-15 SE SE7608112A patent/SE421210B/xx not_active IP Right Cessation
- 1976-07-15 DK DK321376A patent/DK321376A/da not_active Application Discontinuation
- 1976-07-15 BE BE168950A patent/BE844170A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE844170A (fr) | 1977-01-17 |
| NO762473L (enrdf_load_stackoverflow) | 1977-01-18 |
| DK321376A (da) | 1977-01-17 |
| ZA764212B (en) | 1978-03-29 |
| PL210914A1 (pl) | 1979-07-30 |
| SE421210B (sv) | 1981-12-07 |
| NO148886C (no) | 1984-01-04 |
| NO148886B (no) | 1983-09-26 |
| FI64161C (fi) | 1983-10-10 |
| JPS5212189A (en) | 1977-01-29 |
| PL111564B1 (en) | 1980-09-30 |
| ATA460276A (de) | 1979-03-15 |
| FI64161B (fi) | 1983-06-30 |
| SE7608112L (sv) | 1977-01-17 |
| FI761914A7 (enrdf_load_stackoverflow) | 1977-01-17 |
| AT352733B (de) | 1979-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2527568A1 (de) | Verfahren zur herstellung von alkyltetracyclinen und neue tetracyclinderivate | |
| DE1817923C3 (de) | Benzophenonderivate und Verfahren zu ihrer Herstellung | |
| DE1266763B (de) | Verfahren zur Herstellung von in 3-Stellung substituierten Indol- und Indazolderivaten | |
| DE2533924C3 (de) | Verfahren zur Herstellung von 6- Aryl-4H-striazolo [3,4-c] thieno [2,3-e] 1,4-diazepinen | |
| DE2531677A1 (de) | Neue thieno-4,1-oxazepine und verfahren zu ihrer herstellung | |
| DE1912941C3 (de) | 1 -Phenyl^-amino-e-methoxypyridaziniumsalze | |
| DE1290143B (de) | 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinderivate | |
| DE1795231C3 (de) | Verfahren zur Herstellung von 5-Aryl-1,2-dihydro -3H-1,4-benzodiazepin-2-on-4-oxyden | |
| AT247339B (de) | Verfahren zur Herstellung von neuen Chinazolon-Verbindungen | |
| DE3729094A1 (de) | 2,5-substituierte cyclohexan-1,4-dione und verfahren zu deren herstellung | |
| DE1221236B (de) | Verfahren zur Herstellung von Tetracyan-1, 4-dithiin | |
| DE1695695C3 (de) | Verfahren zur Herstellung von 2-Aminofuro eckige Klammer auf 2,3-d eckige Klammer zu thiazolen | |
| CH633555A5 (de) | Verfahren zur herstellung von 1-(2-(dialkylamino)aethyl)-6-aryl-4h-s-triazolo(4,3-a)(1,4)benzodiazepinen. | |
| DE2113254C3 (de) | Verfahren zur Herstellung von γ-Piperidinoburyrophenonderivaten | |
| DE2706701A1 (de) | Verfahren zur herstellung von 3- chlor-5-halogenpyridazinen | |
| DE1954808C3 (enrdf_load_stackoverflow) | ||
| DE2531678A1 (de) | Neue thieno- eckige klammer auf 2,3-e eckige klammer zu -triazolo- eckige klammer auf 3,4-c eckige klammer zu -5,6-dihydro-1,4-diazepine und verfahren zu ihrer herstellung | |
| AT257602B (de) | Verfahren zur Herstellung eines N,N'-disubstituierten 4,4'-Dipyridyliumsalzes | |
| AT250578B (de) | Verfahren zur Herstellung von 3-Enoläthern | |
| AT231449B (de) | Verfahren zur Herstellung von substituierten 3, 4-Dihydro-1, 2, 4-benzothiadiazin-1, 1-dioxyden | |
| AT344179B (de) | Verfahren zur herstellung von neuen benzodiazepinderivaten | |
| DE1470071C (de) | Verfahren zur Herstellung von N Halo gen N phenyl amidinen | |
| AT296316B (de) | Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten und deren N-4-Oxyden | |
| AT256856B (de) | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen | |
| DE1178084B (de) | Verfahren zur Herstellung von 2,3,5,6-Tetracyan-1,4-dithiin und von (2,3-Dihydro-1,4-dithiino)-[2,3:3,4]-isothiazol-5,6,5-tricarbonsaeurenitril |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |