FI56837C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6-staellning substituerade 4,6-dihydro-5h-s-triazolo-/4,3-a/-/1,5/-bensodiazepin-5-oner - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6-staellning substituerade 4,6-dihydro-5h-s-triazolo-/4,3-a/-/1,5/-bensodiazepin-5-oner Download PDFInfo
- Publication number
- FI56837C FI56837C FI1070/74A FI107074A FI56837C FI 56837 C FI56837 C FI 56837C FI 1070/74 A FI1070/74 A FI 1070/74A FI 107074 A FI107074 A FI 107074A FI 56837 C FI56837 C FI 56837C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- substituted
- phenyl
- trifluoromethyl
- triazolo
- Prior art date
Links
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 239000000460 chlorine Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 238000007883 cyanide addition reaction Methods 0.000 claims 1
- 125000001424 substituent group Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 238000010171 animal model Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000001961 anticonvulsive agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 241000906446 Theraps Species 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940125681 anticonvulsant agent Drugs 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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
- 239000000725 suspension Substances 0.000 description 2
- 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 2
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-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
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-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
- KHURWHRZSLXHHI-UHFFFAOYSA-N 6-phenyl-8-(trifluoromethyl)-4H-[1,2,4]triazolo[3,4-d][1,5]benzodiazepin-5-one Chemical compound C=1C(C(F)(F)F)=CC=C(N2C=NN=C2CC2=O)C=1N2C1=CC=CC=C1 KHURWHRZSLXHHI-UHFFFAOYSA-N 0.000 description 1
- 208000024255 Audiogenic seizures Diseases 0.000 description 1
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- -1 N-Methyl-8-nitro-6-phenyl-4,6-dihydro-5H-s-triazolo (4,3-a) (1,5) -benzodiazepin-5-one Chemical compound 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004571 lime Substances 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
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000003557 neuropsychological effect Effects 0.000 description 1
- 238000012346 open field test Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2318673 | 1973-04-13 | ||
| DE2318673A DE2318673A1 (de) | 1973-04-13 | 1973-04-13 | Neue substituierte triazolo-1,5benzodiazepine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56837B FI56837B (fi) | 1979-12-31 |
| FI56837C true FI56837C (fi) | 1980-04-10 |
Family
ID=5877963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1070/74A FI56837C (fi) | 1973-04-13 | 1974-04-09 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6-staellning substituerade 4,6-dihydro-5h-s-triazolo-/4,3-a/-/1,5/-bensodiazepin-5-oner |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5753797B2 (de) |
| AT (1) | AT336025B (de) |
| BE (1) | BE813677A (de) |
| CH (1) | CH591486A5 (de) |
| DE (1) | DE2318673A1 (de) |
| DK (1) | DK136821C (de) |
| ES (1) | ES425216A1 (de) |
| FI (1) | FI56837C (de) |
| FR (1) | FR2225164B1 (de) |
| GB (1) | GB1462095A (de) |
| NL (1) | NL7404884A (de) |
| NO (1) | NO140860C (de) |
| SE (1) | SE419989B (de) |
| SU (1) | SU730307A3 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080323A (en) * | 1977-03-07 | 1978-03-21 | Hoffmann-La Roche Inc. | Imidazo [1,5-a][1,5] benzodiazepines |
| US4118386A (en) * | 1977-04-04 | 1978-10-03 | Hoffmann-La Roche Inc. | Synthesis of imidazo[1,5-a]diazepine-3-carboxylates |
| DE3435972A1 (de) * | 1984-10-01 | 1986-04-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Diazepine enthaltende pharmazeutische zusammensetzungen mit paf-antagonistischer wirkung |
| KR100840852B1 (ko) * | 2004-05-25 | 2008-06-23 | 화이자 프로덕츠 인크. | 테트라아자벤조[ｅ]아줄렌 유도체 및 이의 유사체 |
| BRPI0510273A (pt) | 2004-05-25 | 2007-10-30 | Pfizer Prod Inc | derivados de tetraazabenzo[e]azuleno e análogos destes |
| DE102005061840A1 (de) | 2005-12-23 | 2007-06-28 | Merck Patent Gmbh | Triazolderivate |
| DE102006051796A1 (de) * | 2006-11-03 | 2008-05-08 | Merck Patent Gmbh | Triaza-benzo[e]azulenderivate |
-
1973
- 1973-04-13 DE DE2318673A patent/DE2318673A1/de not_active Withdrawn
-
1974
- 1974-03-26 AT AT248274A patent/AT336025B/de not_active IP Right Cessation
- 1974-04-09 CH CH493674A patent/CH591486A5/xx not_active IP Right Cessation
- 1974-04-09 FI FI1070/74A patent/FI56837C/fi active
- 1974-04-10 NO NO741351A patent/NO140860C/no unknown
- 1974-04-10 ES ES425216A patent/ES425216A1/es not_active Expired
- 1974-04-10 DK DK202474A patent/DK136821C/da not_active IP Right Cessation
- 1974-04-10 NL NL7404884A patent/NL7404884A/xx not_active Application Discontinuation
- 1974-04-10 JP JP49040676A patent/JPS5753797B2/ja not_active Expired
- 1974-04-11 SE SE7405021A patent/SE419989B/xx unknown
- 1974-04-11 SU SU742015007A patent/SU730307A3/ru active
- 1974-04-11 GB GB1633474A patent/GB1462095A/en not_active Expired
- 1974-04-12 BE BE143167A patent/BE813677A/xx not_active IP Right Cessation
- 1974-04-12 FR FR7413023A patent/FR2225164B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7404884A (de) | 1974-10-15 |
| GB1462095A (en) | 1977-01-19 |
| FR2225164A1 (de) | 1974-11-08 |
| ATA248274A (de) | 1976-08-15 |
| JPS5052093A (de) | 1975-05-09 |
| DE2318673A1 (de) | 1974-11-07 |
| AT336025B (de) | 1977-04-12 |
| NO140860B (no) | 1979-08-20 |
| FR2225164B1 (de) | 1977-05-06 |
| FI56837B (fi) | 1979-12-31 |
| SE419989B (sv) | 1981-09-07 |
| BE813677A (fr) | 1974-10-14 |
| NO741351L (no) | 1974-10-15 |
| JPS5753797B2 (de) | 1982-11-15 |
| DK136821B (da) | 1977-11-28 |
| DK136821C (da) | 1978-05-08 |
| SU730307A3 (ru) | 1980-04-25 |
| NO140860C (no) | 1979-11-28 |
| CH591486A5 (de) | 1977-09-30 |
| ES425216A1 (es) | 1976-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Chapleo et al. | Substituted 1, 3, 4-thiadiazoles with anticonvulsant activity. 4. Amidines | |
| FI63234B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 6-enyl-4h-imidazo(1,5-a)(1,4)diazepinfoereningar | |
| US3660423A (en) | 2-(substituted benzyl)methyl-2-imidazolines | |
| FI56837C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6-staellning substituerade 4,6-dihydro-5h-s-triazolo-/4,3-a/-/1,5/-bensodiazepin-5-oner | |
| FI95036C (fi) | Tieno-triatsolo-diatsepiinijohdosten valmistusmenetelmä | |
| CA2037812A1 (fr) | Derives d'imidazo [1,2-c] quinazoline, leur procede de preparation et les compositions pharmaceutiques les renfermant | |
| US5049559A (en) | Thieno-triazolo-diazepine derivatives useful as anti-ischemic agents | |
| FI62308B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 5-ller 6-karboxiderivat av 4,5,6,7-tetrahydro(2,3-c)- och 3,-(-c)pyridiner | |
| Daunis et al. | Heteroaromatic 10-. pi.-electron systems. New s-triazolo-as-triazines with a bridgehead nitrogen atom | |
| Abdel-Rahman et al. | 1, 2, 4-Triazine chemistry part I: orientation of cyclization reactions of functionalized 1, 2, 4-triazine derivatives | |
| FI62314C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara ny 3-((3-alkylisokinol-5-yl)imino)-1,5,10,10a-tetrahydrotia zoo(3,4-b)isokinoliner | |
| FI69058C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara bi(nitrosoureido)polyolderivat | |
| FI84177B (fi) | Foerfarande foer framstaellning av antireumatiskt verkande aroyl-substituerade dihydro-1,4-tiaziner. | |
| FI82465C (fi) | Foerfarande foer framstaellning av nya bensotiazepinderivat. | |
| US4016165A (en) | Triazino benzodiazepines | |
| FI63032C (fi) | Foerfarande foer framstaellning av substituerade 6-fenyl-4h-s-triazolo-(3,4-c)-tieno-(2,3-e)-1,4-diazepiner | |
| FI56385C (fi) | Metod foer framstaellning av bl a som lugnande laekemedel anvaendbara s-triazolo(1,5-a)(1,4)bensodiazepinderivat | |
| CH476753A (de) | Verfahren zur Herstellung von 11-basisch substituierter Dibenzo(b,f)(1,4)thiazepine | |
| CA1053670A (en) | Triazolo-benzodiazepines | |
| AT394563B (de) | Verfahren zur herstellung von thieno-triazolodiazepinderivaten | |
| Conés et al. | Heterocyclic variants of the 1, 5‐benzodiazepine system. V. Derivatives of 2‐(ortho‐R1‐anilino)‐4‐(p‐R2‐phenyl)‐3H‐1, 5‐benzodiazepines | |
| US3822259A (en) | 7-phenyl-1h(1,3)-oxazino(3,2-a)(1,4)benzodiazepine-1,3(2h)-diones | |
| US4356302A (en) | 4H-1,4-Benzothiazine derivatives | |
| FI73203C (fi) | Mellanprodukt foer anvaendning vid framstaellning av terapeutiskt anvaendbara 3,5-diamino-6-fenyl-1,2,4- triazinderivat och foerfarande foer dess framstaellning. | |
| US4399279A (en) | 4H-1,4-Benzothiazine derivatives and intermediates thereto |