DE2265242C2 - Verfahren zur Herstellung von tautomeren 4-Phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-thionen - Google Patents
Verfahren zur Herstellung von tautomeren 4-Phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-thionenInfo
- Publication number
- DE2265242C2 DE2265242C2 DE2265242A DE2265242A DE2265242C2 DE 2265242 C2 DE2265242 C2 DE 2265242C2 DE 2265242 A DE2265242 A DE 2265242A DE 2265242 A DE2265242 A DE 2265242A DE 2265242 C2 DE2265242 C2 DE 2265242C2
- Authority
- DE
- Germany
- Prior art keywords
- radical
- benzodiazepine
- phenyl
- dihydro
- preparation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 10
- FXJFEZPRBYYKHS-UHFFFAOYSA-N 4-phenyl-1,3-dihydro-1,5-benzodiazepine-2-thione Chemical class N=1C2=CC=CC=C2NC(=S)CC=1C1=CC=CC=C1 FXJFEZPRBYYKHS-UHFFFAOYSA-N 0.000 title claims description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 28
- YAWQUTFLMSFPNJ-UHFFFAOYSA-N 3-oxo-3-phenylpropanedithioic acid Chemical compound SC(=S)CC(=O)C1=CC=CC=C1 YAWQUTFLMSFPNJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- -1 isopropylthio radical Chemical class 0.000 claims description 6
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 2
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- YNNRCKMSIAYQBO-UHFFFAOYSA-N 1,5-benzodiazepine-2-thione Chemical class S=C1C=CN=C2C=CC=CC2=N1 YNNRCKMSIAYQBO-UHFFFAOYSA-N 0.000 claims 2
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BJGOGAYCISIWBZ-UHFFFAOYSA-N methyl 3-oxo-3-phenylpropanedithioate Chemical compound CSC(=S)CC(=O)C1=CC=CC=C1 BJGOGAYCISIWBZ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QDKZHQGXPVFLHU-UHFFFAOYSA-N 1,5-benzodiazepin-2-one Chemical class O=C1C=CN=C2C=CC=CC2=N1 QDKZHQGXPVFLHU-UHFFFAOYSA-N 0.000 description 2
- IPUHGFGGCDSILY-UHFFFAOYSA-N 3-oxo-3-(4-phenoxyphenyl)propanedithioic acid Chemical class C1=CC(C(=O)CC(=S)S)=CC=C1OC1=CC=CC=C1 IPUHGFGGCDSILY-UHFFFAOYSA-N 0.000 description 2
- SRZDVYZVEYALFB-UHFFFAOYSA-N 4-phenyl-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C2=CC=CC=C2NC(=O)CC=1C1=CC=CC=C1 SRZDVYZVEYALFB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- IXPPXILQIPXFFT-UHFFFAOYSA-N 1,3-dihydro-1,5-benzodiazepine-2-thione Chemical compound N1C(=S)CC=NC2=CC=CC=C21 IXPPXILQIPXFFT-UHFFFAOYSA-N 0.000 description 1
- DJNIFZYQFLFGDT-UHFFFAOYSA-N 1-(4-phenoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC1=CC=CC=C1 DJNIFZYQFLFGDT-UHFFFAOYSA-N 0.000 description 1
- XUDYHODVSUXRPW-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1SC1=CC=CC=C1 XUDYHODVSUXRPW-UHFFFAOYSA-N 0.000 description 1
- RGBFUCJLQSDTME-UHFFFAOYSA-N 3-(4-phenylphenyl)-3-sulfanylidenepropanedithioic acid Chemical compound C1=CC(C(=S)CC(=S)S)=CC=C1C1=CC=CC=C1 RGBFUCJLQSDTME-UHFFFAOYSA-N 0.000 description 1
- UWSMNBPALLFTAQ-UHFFFAOYSA-N 4-phenyl-2,3-dihydro-1h-1,5-benzodiazepine Chemical compound N=1C2=CC=CC=C2NCCC=1C1=CC=CC=C1 UWSMNBPALLFTAQ-UHFFFAOYSA-N 0.000 description 1
- SLPUGTRSHPWDLZ-UHFFFAOYSA-N 5-phenyl-1,4-benzodiazepin-2-one Chemical class C=12C=CC=CC2=NC(=O)C=NC=1C1=CC=CC=C1 SLPUGTRSHPWDLZ-UHFFFAOYSA-N 0.000 description 1
- HEOUXFGHVMLUNY-UHFFFAOYSA-N 5-phenyl-1,4-benzodiazepine-2-thione Chemical class C1(=CC=CC=C1)C=1N=CC(N=C2C1C=CC=C2)=S HEOUXFGHVMLUNY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YYEVFEDGORIPEX-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C(C(=S)S)C1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)(=O)C(C(=S)S)C1=CC=CC=C1 YYEVFEDGORIPEX-UHFFFAOYSA-N 0.000 description 1
- 101100520142 Caenorhabditis elegans pin-2 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003253 viricidal effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3001871 | 1971-10-19 | ||
| IT2450972A IT1045205B (it) | 1972-05-18 | 1972-05-18 | 2 aminoalchiltio 3h i 5 benzodiazepine terapeuticamente attive e procedimento per la loro preparazione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2265242A1 DE2265242A1 (de) | 1977-01-13 |
| DE2265242C2 true DE2265242C2 (de) | 1983-03-10 |
Family
ID=26328517
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2265242A Expired DE2265242C2 (de) | 1971-10-19 | 1972-10-19 | Verfahren zur Herstellung von tautomeren 4-Phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-thionen |
| DE2251154A Expired DE2251154C3 (de) | 1971-10-19 | 1972-10-19 | 2-Aminoalkylthio-4-(p-thiophenyl)-3H-1,5-benzodiazepinderivate, solche enthaltende Arzneimittel und Desinfektionsmittel und Verfahren zu ihrer Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2251154A Expired DE2251154C3 (de) | 1971-10-19 | 1972-10-19 | 2-Aminoalkylthio-4-(p-thiophenyl)-3H-1,5-benzodiazepinderivate, solche enthaltende Arzneimittel und Desinfektionsmittel und Verfahren zu ihrer Herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3933793A (enExample) |
| JP (1) | JPS5616788B2 (enExample) |
| AT (1) | AT321922B (enExample) |
| BE (1) | BE790224A (enExample) |
| CA (1) | CA975770A (enExample) |
| DE (2) | DE2265242C2 (enExample) |
| DK (1) | DK143800C (enExample) |
| ES (1) | ES407722A1 (enExample) |
| FR (1) | FR2157890B1 (enExample) |
| IE (1) | IE37514B1 (enExample) |
| IL (1) | IL40563A (enExample) |
| NL (1) | NL147141B (enExample) |
| NO (1) | NO138113C (enExample) |
| SE (1) | SE393983B (enExample) |
| YU (1) | YU36935B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123430A (en) * | 1977-11-10 | 1978-10-31 | G. D. Searle & Co. | 2-Aryl-4-(1-piperazinyl)-3H-1,5-benzodiazepines |
| JPH0681779U (ja) * | 1993-05-11 | 1994-11-22 | エムエイシイサンコー株式会社 | 状差し |
| CN112812070B (zh) * | 2021-01-30 | 2022-10-21 | 陕西师范大学 | 一种吡啶钯高效催化制备苯二氮卓类化合物的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3296251A (en) * | 1963-02-26 | 1967-01-03 | American Home Prod | 3-mercapto and 3-substituted mercapto-1, 3-dihydro-2h-1, 4-benzodiazepin-2-ones |
| DE1933666A1 (de) * | 1968-08-17 | 1970-09-03 | Egyt Gyogyszervegyeszeti Gyar | Neue 2,3-Dihydro-6,7-benzo-(1,5)-diazepine und Verfahren zur Herstellung derselben |
| US3595858A (en) * | 1969-10-21 | 1971-07-27 | Pfizer | 1h-1,5-benzodiazepinecarboxamide antiinflammatory agents |
| DE2053679A1 (de) * | 1970-11-02 | 1972-05-18 | Neue 2-Alkoxy-(bzw. 2-Alkylmercapto)- |
-
0
- BE BE790224D patent/BE790224A/xx not_active IP Right Cessation
-
1972
- 1972-08-02 JP JP7757372A patent/JPS5616788B2/ja not_active Expired
- 1972-10-04 YU YU2494/72A patent/YU36935B/xx unknown
- 1972-10-06 DK DK493672A patent/DK143800C/da not_active IP Right Cessation
- 1972-10-10 US US05/296,045 patent/US3933793A/en not_active Expired - Lifetime
- 1972-10-12 IL IL40563A patent/IL40563A/en unknown
- 1972-10-13 IE IE1392/72A patent/IE37514B1/xx unknown
- 1972-10-16 AT AT884472A patent/AT321922B/de not_active IP Right Cessation
- 1972-10-17 NL NL727214034A patent/NL147141B/xx not_active IP Right Cessation
- 1972-10-18 SE SE7213420A patent/SE393983B/xx unknown
- 1972-10-18 ES ES407722A patent/ES407722A1/es not_active Expired
- 1972-10-18 NO NO3736/72A patent/NO138113C/no unknown
- 1972-10-18 CA CA154,243A patent/CA975770A/en not_active Expired
- 1972-10-19 DE DE2265242A patent/DE2265242C2/de not_active Expired
- 1972-10-19 FR FR7237114A patent/FR2157890B1/fr not_active Expired
- 1972-10-19 DE DE2251154A patent/DE2251154C3/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| NO138113B (no) | 1978-03-28 |
| FR2157890B1 (enExample) | 1975-10-31 |
| IL40563A (en) | 1976-01-30 |
| DE2265242A1 (de) | 1977-01-13 |
| NO138113C (no) | 1978-07-05 |
| JPS5616788B2 (enExample) | 1981-04-18 |
| YU249472A (en) | 1982-06-18 |
| NL147141B (nl) | 1975-09-15 |
| ES407722A1 (es) | 1976-02-16 |
| DE2251154C3 (de) | 1981-06-25 |
| IE37514L (en) | 1973-04-19 |
| DK143800B (da) | 1981-10-12 |
| US3933793A (en) | 1976-01-20 |
| DE2251154B2 (de) | 1980-10-16 |
| NL7214034A (enExample) | 1973-04-25 |
| DE2251154A1 (de) | 1973-04-26 |
| FR2157890A1 (enExample) | 1973-06-08 |
| IE37514B1 (en) | 1977-08-17 |
| JPS4848487A (enExample) | 1973-07-09 |
| AT321922B (de) | 1975-04-25 |
| BE790224A (fr) | 1973-02-15 |
| SE393983B (sv) | 1977-05-31 |
| CA975770A (en) | 1975-10-07 |
| DK143800C (da) | 1982-03-29 |
| IL40563A0 (en) | 1972-12-29 |
| YU36935B (en) | 1984-08-31 |
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