CA1113464A - 3-hydroxy-1,4-benzodiazepine-2-ones and process for the preparation thereof - Google Patents
3-hydroxy-1,4-benzodiazepine-2-ones and process for the preparation thereofInfo
- Publication number
- CA1113464A CA1113464A CA342,046A CA342046A CA1113464A CA 1113464 A CA1113464 A CA 1113464A CA 342046 A CA342046 A CA 342046A CA 1113464 A CA1113464 A CA 1113464A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- benzodiazepine
- dihydro
- chloro
- phenyl
- 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 abstract description 27
- YSPYFFRTSUIPCB-UHFFFAOYSA-N 1h-1,4-benzodiazepine-2,3-dione Chemical class N1C(=O)C(=O)N=CC2=CC=CC=C21 YSPYFFRTSUIPCB-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 9
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 7
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 claims description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 5
- 150000003112 potassium compounds Chemical class 0.000 claims description 5
- FERBACJQVQVCKH-UHFFFAOYSA-N 3-Hydroxy-N-desalkyl-2-Oxoquazepam Natural products C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1F FERBACJQVQVCKH-UHFFFAOYSA-N 0.000 claims description 4
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 claims description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 2
- GFJFWUYSUSJMKF-UHFFFAOYSA-N 3-(3-hydroxy-7-nitro-2-oxo-5-phenyl-3h-1,4-benzodiazepin-1-yl)propanenitrile Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(CCC#N)C(=O)C(O)N=C1C1=CC=CC=C1 GFJFWUYSUSJMKF-UHFFFAOYSA-N 0.000 claims description 2
- CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 claims description 2
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 claims description 2
- DIWRORZWFLOCLC-UHFFFAOYSA-N Lorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-UHFFFAOYSA-N 0.000 claims description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 235000009518 sodium iodide Nutrition 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- OGGAKRAZPNNKQV-UHFFFAOYSA-N 3-(7-chloro-3-hydroxy-2-oxo-5-phenyl-3h-1,4-benzodiazepin-1-yl)propanenitrile Chemical compound C12=CC(Cl)=CC=C2N(CCC#N)C(=O)C(O)N=C1C1=CC=CC=C1 OGGAKRAZPNNKQV-UHFFFAOYSA-N 0.000 claims 1
- INEPVPAFDASXEE-UHFFFAOYSA-N 3-[5-(2-chlorophenyl)-3-hydroxy-7-nitro-2-oxo-3h-1,4-benzodiazepin-1-yl]propanenitrile Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(CCC#N)C(=O)C(O)N=C1C1=CC=CC=C1Cl INEPVPAFDASXEE-UHFFFAOYSA-N 0.000 claims 1
- GPLVZUVUVARVDC-UHFFFAOYSA-N 3-[5-(2-fluorophenyl)-3-hydroxy-7-nitro-2-oxo-3h-1,4-benzodiazepin-1-yl]propanenitrile Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(CCC#N)C(=O)C(O)N=C1C1=CC=CC=C1F GPLVZUVUVARVDC-UHFFFAOYSA-N 0.000 claims 1
- DXDSXOQEASNCQT-UHFFFAOYSA-N 3-[7-chloro-5-(2-chlorophenyl)-3-hydroxy-2-oxo-3h-1,4-benzodiazepin-1-yl]propanenitrile Chemical compound C12=CC(Cl)=CC=C2N(CCC#N)C(=O)C(O)N=C1C1=CC=CC=C1Cl DXDSXOQEASNCQT-UHFFFAOYSA-N 0.000 claims 1
- WFQPYFHXXXIGLW-UHFFFAOYSA-N 3-hydroxy-7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 WFQPYFHXXXIGLW-UHFFFAOYSA-N 0.000 claims 1
- UHFIFTRHLBAWGY-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-hydroxy-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1F UHFIFTRHLBAWGY-UHFFFAOYSA-N 0.000 claims 1
- CGUAABBXJZGDPW-UHFFFAOYSA-N 7-chloro-3-hydroxy-1-(2-methoxyethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1C(O)C(=O)N(CCOC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 CGUAABBXJZGDPW-UHFFFAOYSA-N 0.000 claims 1
- 229960001040 ammonium chloride Drugs 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 230000001624 sedative effect Effects 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 229960004535 oxazepam Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960004391 lorazepam Drugs 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 238000006972 Polonovski rearrangement reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000007278 cyanoethylation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229940125724 sleeping drug Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- -1 sulfonyloxy group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ATA9031/78 | 1978-12-18 | ||
| AT903178A AT361492B (de) | 1978-12-18 | 1978-12-18 | Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113464A true CA1113464A (en) | 1981-12-01 |
Family
ID=3610590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA342,046A Expired CA1113464A (en) | 1978-12-18 | 1979-12-17 | 3-hydroxy-1,4-benzodiazepine-2-ones and process for the preparation thereof |
Country Status (25)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0264797B1 (en) * | 1986-10-24 | 1996-01-10 | Abbott Laboratories | Benzodiazepines assay, tracers, immunogens and antibodies |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3311612A (en) * | 1967-03-28 | Process for preparing | ||
| US3371085A (en) * | 1959-12-10 | 1968-02-27 | Hoffmann La Roche | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
| BE621819A (cg-RX-API-DMAC7.html) * | 1961-08-29 | |||
| GB1050401A (cg-RX-API-DMAC7.html) * | 1963-02-19 | 1900-01-01 | ||
| NL298071A (cg-RX-API-DMAC7.html) * | 1963-06-04 | |||
| GB1051795A (cg-RX-API-DMAC7.html) * | 1964-02-11 | |||
| FR135F (cg-RX-API-DMAC7.html) * | 1964-08-13 | |||
| NO120269B (cg-RX-API-DMAC7.html) * | 1965-11-02 | 1970-09-28 | Hoffmann La Roche | |
| US3464978A (en) * | 1967-04-21 | 1969-09-02 | Hoffmann La Roche | 1-substituted urea alkyl 1,2-dihydro-1,4-benzodiazepines and benzodiazepin - 2-ones |
| CH574421A5 (en) * | 1969-02-14 | 1976-04-15 | Hoffmann La Roche | Benzodiazepines |
| AT309436B (de) * | 1970-06-23 | 1973-08-27 | Gerot Pharmazeutika | Verfahren zur Herstellung von 3-Hydroxy-1,4-benzodiazepin Derivaten oder deren Salzen |
| US4065451A (en) * | 1971-03-30 | 1977-12-27 | American Home Products | 1,3-Dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts |
| CH573416A5 (cg-RX-API-DMAC7.html) * | 1971-07-30 | 1976-03-15 | Sumitomo Chemical Co | |
| US3801568A (en) * | 1972-02-07 | 1974-04-02 | American Home Prod | Optically active 1,3-dihydro-3-substituted 5-phenyl-2h-1,4-benzodiazepin-2-ones and process for their separation |
| JPS494226A (cg-RX-API-DMAC7.html) * | 1972-04-27 | 1974-01-16 |
-
1978
- 1978-12-18 AT AT903178A patent/AT361492B/de not_active IP Right Cessation
-
1979
- 1979-11-26 NO NO793827A patent/NO151859C/no unknown
- 1979-11-30 DK DK510379A patent/DK154973C/da not_active IP Right Cessation
- 1979-12-05 FR FR7929879A patent/FR2444672A1/fr active Granted
- 1979-12-05 ZA ZA00796600A patent/ZA796600B/xx unknown
- 1979-12-11 AU AU53664/79A patent/AU532331B2/en not_active Expired
- 1979-12-11 NL NLAANVRAGE7908919,A patent/NL187068C/xx not_active IP Right Cessation
- 1979-12-13 DE DE19792950235 patent/DE2950235A1/de active Granted
- 1979-12-13 LU LU81990A patent/LU81990A1/fr unknown
- 1979-12-14 ES ES486895A patent/ES486895A0/es active Granted
- 1979-12-14 BE BE0/198574A patent/BE880632A/fr not_active IP Right Cessation
- 1979-12-14 SE SE7910333A patent/SE440351B/sv not_active IP Right Cessation
- 1979-12-14 FI FI793924A patent/FI67375C/fi not_active IP Right Cessation
- 1979-12-14 GB GB7943107A patent/GB2043630B/en not_active Expired
- 1979-12-17 YU YU3087/79A patent/YU40586B/xx unknown
- 1979-12-17 GR GR60778A patent/GR73901B/el unknown
- 1979-12-17 CA CA342,046A patent/CA1113464A/en not_active Expired
- 1979-12-18 JP JP16367879A patent/JPS5583764A/ja active Granted
- 1979-12-18 IT IT28149/79A patent/IT1193345B/it active
- 1979-12-18 CH CH1123179A patent/CH643248A5/de not_active IP Right Cessation
-
1981
- 1981-05-11 US US06/262,676 patent/US4388313A/en not_active Expired - Lifetime
-
1985
- 1985-02-19 SG SG135/85A patent/SG13585G/en unknown
- 1985-05-02 HK HK333/85A patent/HK33385A/xx not_active IP Right Cessation
-
1986
- 1986-12-30 MY MY20/86A patent/MY8600020A/xx unknown
-
1993
- 1993-07-21 BG BG097977A patent/BG60474B2/bg unknown
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