CS203083B2 - Method of producing novel substituted 6-aryl-4h-o-triazolo/3,4-c/thieno/2,3-e/1,4-diazepines - Google Patents
Method of producing novel substituted 6-aryl-4h-o-triazolo/3,4-c/thieno/2,3-e/1,4-diazepines Download PDFInfo
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- CS203083B2 CS203083B2 CS751284A CS128475A CS203083B2 CS 203083 B2 CS203083 B2 CS 203083B2 CS 751284 A CS751284 A CS 751284A CS 128475 A CS128475 A CS 128475A CS 203083 B2 CS203083 B2 CS 203083B2
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- Czechoslovakia
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- formula
- compound
- group
- acid addition
- physiologically acceptable
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- 150000004911 1,4-diazepines Chemical class 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 239000002253 acid Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 58
- -1 methylmethoxy Chemical group 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- OMXRYYPDXHPHQN-UHFFFAOYSA-N 7h-thieno[2,3-e][1,4]diazepine Chemical class C1=CN=CC2=CCSC2=N1 OMXRYYPDXHPHQN-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229920003064 carboxyethyl cellulose Polymers 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HUYREUUJFLHEDE-UHFFFAOYSA-N cyclohexanecarbohydrazide Chemical compound NNC(=O)C1CCCCC1 HUYREUUJFLHEDE-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- LLGRORFWHFVNIK-UHFFFAOYSA-N oxolane-2-carbohydrazide Chemical compound NNC(=O)C1CCCO1 LLGRORFWHFVNIK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS785955A CS203085B2 (cs) | 1974-07-20 | 1978-09-14 | Způsob výroby nových substituovaných B-aryl-4H-s- -triazolo[3,4-c ] thieno(2,3-e ] -1,4-diazepinů |
| CS785954A CS203084B2 (cs) | 1974-03-02 | 1978-09-19 | Způsob výroby nových substituovaných 6-aryl-4H-s- -triazoloJ 3,4-c) thiono12,3-e ] -1,4-diazepinů |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410030A DE2410030C3 (de) | 1974-03-02 | 1974-03-02 | 8-Brom-6-phenyl-4H-s-triazolo[3,4-c]thieno[2,3-e]1,4-diazepine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
| DE2435041A DE2435041C3 (de) | 1974-07-20 | 1974-07-20 | 8-Substituierte 6-Aryl-4H-s-triazolo [3,4c] thieno [23e] 1,4-diazepine, Verfahren zu ihrer Herstellung, ihre Verwendung in Arzneimitteln und diese enthaltende pharmazeutische Präparate |
| DE19742445430 DE2445430B2 (de) | 1974-07-20 | 1974-09-24 | 1 - substituierte 6-aryl-4h-striazolo eckige klammer auf 3,4c eckige klammer zu thieno-eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| DE2460776A DE2460776C2 (de) | 1974-07-20 | 1974-12-21 | 1-substituierte 6-Aryl-4H-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepine, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate sowie Zwischenprodukte und Verfahren zur Herstellung dieser Zwischenprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203083B2 true CS203083B2 (en) | 1981-02-27 |
Family
ID=27431816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS751284A CS203083B2 (en) | 1974-03-02 | 1975-02-26 | Method of producing novel substituted 6-aryl-4h-o-triazolo/3,4-c/thieno/2,3-e/1,4-diazepines |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4094984A (en, 2012) |
| JP (1) | JPS5930713B2 (en, 2012) |
| AT (1) | AT338799B (en, 2012) |
| BE (1) | BE826179A (en, 2012) |
| BG (3) | BG26392A4 (en, 2012) |
| CA (1) | CA1073904A (en, 2012) |
| CH (1) | CH611900A5 (en, 2012) |
| CS (1) | CS203083B2 (en, 2012) |
| DD (1) | DD120022A5 (en, 2012) |
| DK (1) | DK141876C (en, 2012) |
| ES (2) | ES435223A1 (en, 2012) |
| FI (1) | FI59099C (en, 2012) |
| FR (3) | FR2262525B1 (en, 2012) |
| GB (1) | GB1497527A (en, 2012) |
| IE (1) | IE42737B1 (en, 2012) |
| IL (1) | IL52138A0 (en, 2012) |
| NL (2) | NL163515C (en, 2012) |
| NO (1) | NO140671C (en, 2012) |
| PH (2) | PH15360A (en, 2012) |
| PL (2) | PL99177B1 (en, 2012) |
| RO (3) | RO71261B (en, 2012) |
| SE (1) | SE421794B (en, 2012) |
| SU (2) | SU583758A3 (en, 2012) |
| YU (3) | YU39732B (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT338799B (de) * | 1974-03-02 | 1977-09-12 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer substituierter 6-aryl-4h-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepine und ihrer salze |
| AT358049B (de) * | 1977-01-27 | 1980-08-11 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer 1-substi- tuierter 8-jod-6-phenyl-4h-s-triazolo(3,4c) thieno(2,3e)1,4-diazepine und deren salzen |
| DE2708121A1 (de) * | 1977-02-25 | 1978-09-07 | Boehringer Sohn Ingelheim | Triazolo-thieno-diazepin-l-one, verfahren zu ihrer herstellung und arzneimittel |
| FI63033C (fi) * | 1977-07-21 | 1983-04-11 | Boehringer Sohn Ingelheim | Foerfarande foer framstaellning av anxiolytiska tranquilliserande sedativa och/eller neuroleptiska substituerade 1-piperazinyl-4h-s-triazolo(3,4-c)tieno(2,3-e)-1,4-diazepiner |
| DE2830782A1 (de) * | 1978-07-13 | 1980-01-24 | Boehringer Sohn Ingelheim | Neue substituierte 4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| PH30676A (en) * | 1986-07-22 | 1997-09-16 | Boehringer Ingelhein Kg | Hetrazepine compounds which have useful pharmaceutical utility |
| ES2039408T3 (es) * | 1986-11-17 | 1993-10-01 | Yoshitomi Pharmaceutical Industries, Ltd. | Un procedimiento para preparar un compuesto de tienotriazolodiazepina. |
| US4959361A (en) * | 1987-12-18 | 1990-09-25 | Hoffmann-La Roche Inc. | Triazolo(4,3-A)(1,4)benzodiazepines and thieno (3,2-F)(1,2,4)triazolo(4,3-A)(1,4)diazepine compounds which have useful activity as platelet activating factor (PAF) antagonists |
| DE4010528A1 (de) * | 1990-04-02 | 1991-10-17 | Boehringer Ingelheim Kg | Praeparativ chromatographisches trennverfahren zur herstellung enantiomerenreiner hetrazepine |
| WO1995032963A1 (fr) * | 1994-06-01 | 1995-12-07 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose de thienylazole et compose de thienotriazolodiazepine |
| US5552399A (en) * | 1994-11-02 | 1996-09-03 | Janssen Pharmaceutica N.V. | Substituted tetracyclic azepine derivatives |
| US6348485B1 (en) | 1998-06-09 | 2002-02-19 | Takeda Chemical Industries, Ltd. | Method for treating or preventing sleep disorders |
| US6884886B2 (en) * | 2001-04-04 | 2005-04-26 | Boehringer Ingelheim Pharma Kg | Process for preparing 6-aryl-4H-S-triazolo[3,4-c]-thieno[2,3-e]-1,4-diazepines |
| DE10116378C2 (de) * | 2001-04-04 | 2003-05-28 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von 6-Aryl-4H-s-triazolo[3,4-c]-thieno[2,3-e]-1,4-diazepinen |
| CN106397452A (zh) * | 2016-07-26 | 2017-02-15 | 江苏兢业制药有限公司 | 7‑溴‑5‑(2‑氯苯基)‑1,3‑二氢噻吩并[2,3e]‑1,4‑二氮杂卓‑2‑硫酮的制备方法 |
| JP6843811B2 (ja) | 2018-09-19 | 2021-03-17 | 岬環境プラン株式会社 | 撒積貨物船の船艙壁面清掃装置 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3751426A (en) * | 1971-04-28 | 1973-08-07 | Upjohn Co | 1-substituted-6-phenyl-4h-s-triazolo(4,3-a)(1,6)benzodiazepine compounds |
| US3709899A (en) * | 1971-04-28 | 1973-01-09 | Upjohn Co | 6-phenyl-4h-s-triazolo(4,3-a)(1,4)benzodiazepines and their production |
| US3849934A (en) * | 1971-05-03 | 1974-11-26 | Scm Corp | Alpha-aryl-n-lower alkyl nitrone-containing compositions useful as anti-fungal agents |
| US3856802A (en) * | 1971-05-10 | 1974-12-24 | Upjohn Co | 1,6-DISUBSTITUTED-4H-5-{8 4,3-a{9 BENZODIAZEPINES |
| GB1323277A (en) * | 1971-05-10 | 1973-07-11 | Upjohn Co | Triazolobenzodiazepines |
| US3681343A (en) * | 1971-05-11 | 1972-08-01 | Upjohn Co | 6-phenyl-s-triazolo{8 4,3-a{9 {8 1,4{9 {0 benzodiazepines |
| GB1332766A (en) * | 1971-06-18 | 1973-10-03 | Upjohn Co | Triazolo-benzodiazepines |
| US3904641A (en) * | 1971-06-18 | 1975-09-09 | Yoshitomi Pharmaceutical | Triazolothienodiazepine compounds |
| US3767660A (en) * | 1971-09-13 | 1973-10-23 | Upjohn Co | 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
| GB1377230A (en) * | 1971-09-13 | 1974-12-11 | Upjohn Co | 4h-s-triazolo -4,3-a- 1,4-benzodiazepines |
| GB1387783A (en) * | 1972-08-08 | 1975-03-19 | Yoshitomi Pharmaceutical | Thiophene derivatives, method for their preparation and pharmaceutical composition thereof |
| PH12303A (en) * | 1973-02-08 | 1979-01-16 | Hoffmann La Roche | Thienotriazolodiazepine derivatives |
| AT338799B (de) * | 1974-03-02 | 1977-09-12 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer substituierter 6-aryl-4h-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepine und ihrer salze |
-
1975
- 1975-02-14 AT AT108975A patent/AT338799B/de not_active IP Right Cessation
- 1975-02-25 SU SU7502112490A patent/SU583758A3/ru active
- 1975-02-26 CS CS751284A patent/CS203083B2/cs unknown
- 1975-02-27 IE IE422/75A patent/IE42737B1/en unknown
- 1975-02-27 CH CH251075A patent/CH611900A5/xx not_active IP Right Cessation
- 1975-02-27 YU YU477/75A patent/YU39732B/xx unknown
- 1975-02-28 RO RO90413A patent/RO71261B/ro unknown
- 1975-02-28 RO RO90412A patent/RO71260B/ro unknown
- 1975-02-28 SE SE7502313A patent/SE421794B/xx not_active IP Right Cessation
- 1975-02-28 DK DK80775A patent/DK141876C/da active
- 1975-02-28 NO NO750691A patent/NO140671C/no unknown
- 1975-02-28 BG BG030630A patent/BG26392A4/xx unknown
- 1975-02-28 BE BE153916A patent/BE826179A/xx not_active IP Right Cessation
- 1975-02-28 BG BG029114A patent/BG26390A3/xx unknown
- 1975-02-28 RO RO7581529A patent/RO66909A/ro unknown
- 1975-02-28 NL NL7502391.A patent/NL163515C/xx active Protection Beyond IP Right Term
- 1975-02-28 FR FR7506414A patent/FR2262525B1/fr not_active Expired
- 1975-02-28 DD DD184500A patent/DD120022A5/xx unknown
- 1975-02-28 JP JP50025531A patent/JPS5930713B2/ja not_active Expired
- 1975-02-28 BG BG030629A patent/BG26391A4/xx unknown
- 1975-02-28 FI FI750592A patent/FI59099C/fi not_active IP Right Cessation
- 1975-03-01 ES ES435223A patent/ES435223A1/es not_active Expired
- 1975-03-01 PL PL1975195734A patent/PL99177B1/pl unknown
- 1975-03-01 PL PL1975178420A patent/PL96223B1/pl unknown
- 1975-03-03 PH PH16964A patent/PH15360A/en unknown
- 1975-03-03 GB GB27236/77A patent/GB1497527A/en not_active Expired
- 1975-04-30 ES ES437261A patent/ES437261A1/es not_active Expired
- 1975-08-27 SU SU752167354A patent/SU648104A3/ru active
-
1976
- 1976-01-21 FR FR7601563A patent/FR2287449A1/fr active Granted
-
1977
- 1977-05-20 IL IL52138A patent/IL52138A0/xx unknown
- 1977-09-30 FR FR7729531A patent/FR2361398A1/fr active Granted
- 1977-10-06 US US05/839,792 patent/US4094984A/en not_active Expired - Lifetime
- 1977-11-30 US US05/855,753 patent/US4199588A/en not_active Expired - Lifetime
-
1978
- 1978-10-31 CA CA315,113A patent/CA1073904A/en not_active Expired
-
1980
- 1980-04-23 PH PH23939A patent/PH15120A/en unknown
-
1982
- 1982-05-13 YU YU1025/82A patent/YU39891B/xx unknown
- 1982-05-13 YU YU1024/82A patent/YU39890B/xx unknown
-
1993
- 1993-06-30 NL NL930123C patent/NL930123I1/nl unknown
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