CA1178583A - 1,7-dihydro-pyrrolo ¬3,4-e| ¬1,4|diazepin- 2(1h)-one derivatives - Google Patents
1,7-dihydro-pyrrolo ¬3,4-e| ¬1,4|diazepin- 2(1h)-one derivativesInfo
- Publication number
- CA1178583A CA1178583A CA000404438A CA404438A CA1178583A CA 1178583 A CA1178583 A CA 1178583A CA 000404438 A CA000404438 A CA 000404438A CA 404438 A CA404438 A CA 404438A CA 1178583 A CA1178583 A CA 1178583A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- diazepin
- dihydro
- dimethyl
- process according
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 147
- 239000001257 hydrogen Substances 0.000 claims abstract description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 63
- 230000008569 process Effects 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 41
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 21
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- -1 propy] Chemical group 0.000 claims description 13
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 230000029936 alkylation Effects 0.000 claims description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 6
- JMYGWEDIYIXTFL-UHFFFAOYSA-N n-(4-benzoyl-1,5-dimethylpyrrol-3-yl)-2-iodoacetamide Chemical compound ICC(=O)NC1=CN(C)C(C)=C1C(=O)C1=CC=CC=C1 JMYGWEDIYIXTFL-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- XWQYRPCAJKCGEP-UHFFFAOYSA-N n-[4-(2-chlorobenzoyl)-1,5-dimethylpyrrol-3-yl]-2-iodoacetamide Chemical compound ICC(=O)NC1=CN(C)C(C)=C1C(=O)C1=CC=CC=C1Cl XWQYRPCAJKCGEP-UHFFFAOYSA-N 0.000 claims description 5
- CYPYOGOPKDBEFY-UHFFFAOYSA-N 1-(2-chlorophenyl)butane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1Cl CYPYOGOPKDBEFY-UHFFFAOYSA-N 0.000 claims description 4
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- WOSOKJAXSFXOMF-UHFFFAOYSA-N n-(4-benzoyl-1,5-dimethylpyrrol-3-yl)-2-chloroacetamide Chemical compound ClCC(=O)NC1=CN(C)C(C)=C1C(=O)C1=CC=CC=C1 WOSOKJAXSFXOMF-UHFFFAOYSA-N 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000008707 rearrangement Effects 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims 5
- LTLFICSAXLBXHT-UHFFFAOYSA-N (4-amino-2-methyl-1h-pyrrol-3-yl)-(2-chlorophenyl)methanone Chemical compound N1C=C(N)C(C(=O)C=2C(=CC=CC=2)Cl)=C1C LTLFICSAXLBXHT-UHFFFAOYSA-N 0.000 claims 3
- APPNFPAQYIBGLU-UHFFFAOYSA-N (4-amino-2-methyl-1h-pyrrol-3-yl)-phenylmethanone Chemical compound N1C=C(N)C(C(=O)C=2C=CC=CC=2)=C1C APPNFPAQYIBGLU-UHFFFAOYSA-N 0.000 claims 3
- KGZTZUTZHFJDAW-UHFFFAOYSA-N n-(4-benzoyl-1,5-dimethylpyrrol-3-yl)-2-(hydroxyamino)acetamide Chemical compound ONCC(=O)NC1=CN(C)C(C)=C1C(=O)C1=CC=CC=C1 KGZTZUTZHFJDAW-UHFFFAOYSA-N 0.000 claims 3
- OOMMAGWBUSBHMG-UHFFFAOYSA-N n-(4-benzoyl-5-methyl-1h-pyrrol-3-yl)-2-chloroacetamide Chemical compound N1C=C(NC(=O)CCl)C(C(=O)C=2C=CC=CC=2)=C1C OOMMAGWBUSBHMG-UHFFFAOYSA-N 0.000 claims 3
- 235000011149 sulphuric acid Nutrition 0.000 claims 3
- 239000001117 sulphuric acid Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- JLTRBSRRNXWQTM-UHFFFAOYSA-N n-[4-(2-chlorobenzoyl)-1,5-dimethylpyrrol-3-yl]-2-(hydroxyamino)acetamide Chemical compound ONCC(=O)NC1=CN(C)C(C)=C1C(=O)C1=CC=CC=C1Cl JLTRBSRRNXWQTM-UHFFFAOYSA-N 0.000 claims 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 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- KSCXAYXHAGZJPZ-UHFFFAOYSA-N 4-hydroxy-6,7-dimethyl-5-phenyl-3,5-dihydro-1h-pyrrolo[3,4-e][1,4]diazepin-1-ium-2-one;chloride Chemical compound [Cl-].ON1CC(=O)[NH2+]C2=CN(C)C(C)=C2C1C1=CC=CC=C1 KSCXAYXHAGZJPZ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 239000002249 anxiolytic agent Substances 0.000 abstract description 9
- 230000001773 anti-convulsant effect Effects 0.000 abstract description 8
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 8
- 229960003965 antiepileptics Drugs 0.000 abstract description 8
- 230000000049 anti-anxiety effect Effects 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 230000000949 anxiolytic effect Effects 0.000 description 4
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 4
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- ZDJJKOOESFJHGL-UHFFFAOYSA-N pyrrolo[3,2-c]diazepine Chemical class N1=CC=CC2=NC=CC2=N1 ZDJJKOOESFJHGL-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical class N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical 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)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8117184 | 1981-06-04 | ||
| GB8117184 | 1981-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1178583A true CA1178583A (en) | 1984-11-27 |
Family
ID=10522285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000404438A Expired CA1178583A (en) | 1981-06-04 | 1982-06-03 | 1,7-dihydro-pyrrolo ¬3,4-e| ¬1,4|diazepin- 2(1h)-one derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4402970A (en, 2012) |
| EP (1) | EP0066762B1 (en, 2012) |
| JP (1) | JPS57212184A (en, 2012) |
| AT (1) | ATE16594T1 (en, 2012) |
| AU (1) | AU551695B2 (en, 2012) |
| CA (1) | CA1178583A (en, 2012) |
| DE (1) | DE3267543D1 (en, 2012) |
| DK (1) | DK160307C (en, 2012) |
| ES (1) | ES512811A0 (en, 2012) |
| GR (1) | GR76455B (en, 2012) |
| IE (1) | IE53343B1 (en, 2012) |
| IL (1) | IL65896A (en, 2012) |
| PH (1) | PH18767A (en, 2012) |
| ZA (1) | ZA823701B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4508730A (en) * | 1982-09-08 | 1985-04-02 | Gruppo Lepetit S.P.A. | 1,7-Dihydro-pyrrolo[3,4-e][1,4]diazepin-2(3H)-one derivatives a process for preparing them and their use as anticonvulsant and anti-anxiety agents |
| US4517195A (en) * | 1984-07-02 | 1985-05-14 | Hoechst-Roussel Pharmaceuticals Inc. | Pyrrolo[1,2-b][1,2,5]triazepines and pharmaceutical compositions thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795231C3 (de) * | 1963-05-29 | 1978-07-13 | American Home Products Corp., New York, N.Y. (V.St.A.) | Verfahren zur Herstellung von 5-Aryl-1,2-dihydro -3H-1,4-benzodiazepin-2-on-4-oxyden |
| NL298071A (en, 2012) * | 1963-06-04 | |||
| US3553210A (en) * | 1968-12-16 | 1971-01-05 | Parke Davis & Co | 3-methyl-8-phenylpyrazolo(4,3-e)(1,4)diazepin-5(1h)-one, 7-oxide compounds |
| US3553207A (en) * | 1968-12-16 | 1971-01-05 | Parke Davis & Co | Phenylpyrazolodiazepinone compounds |
| GB1433103A (en) * | 1974-03-20 | 1976-04-22 | Lepetit Spa | Pharmacologically active pyrrolodiazepines |
-
1982
- 1982-05-17 GR GR68184A patent/GR76455B/el unknown
- 1982-05-20 AU AU83870/82A patent/AU551695B2/en not_active Ceased
- 1982-05-22 EP EP82104487A patent/EP0066762B1/en not_active Expired
- 1982-05-22 AT AT82104487T patent/ATE16594T1/de active
- 1982-05-22 DE DE8282104487T patent/DE3267543D1/de not_active Expired
- 1982-05-24 US US06/381,272 patent/US4402970A/en not_active Expired - Fee Related
- 1982-05-27 ZA ZA823701A patent/ZA823701B/xx unknown
- 1982-05-27 IL IL65896A patent/IL65896A/xx unknown
- 1982-05-31 PH PH27383A patent/PH18767A/en unknown
- 1982-06-01 DK DK245182A patent/DK160307C/da not_active IP Right Cessation
- 1982-06-03 CA CA000404438A patent/CA1178583A/en not_active Expired
- 1982-06-03 ES ES512811A patent/ES512811A0/es active Granted
- 1982-06-03 IE IE1336/82A patent/IE53343B1/en not_active IP Right Cessation
- 1982-06-03 JP JP57095597A patent/JPS57212184A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE821336L (en) | 1982-12-04 |
| PH18767A (en) | 1985-09-20 |
| DK245182A (da) | 1982-12-05 |
| DE3267543D1 (de) | 1986-01-02 |
| EP0066762A3 (en) | 1983-04-27 |
| EP0066762A2 (en) | 1982-12-15 |
| DK160307B (da) | 1991-02-25 |
| ES8307809A1 (es) | 1983-08-01 |
| EP0066762B1 (en) | 1985-11-21 |
| GR76455B (en, 2012) | 1984-08-10 |
| AU8387082A (en) | 1982-12-09 |
| ATE16594T1 (de) | 1985-12-15 |
| IL65896A (en) | 1985-08-30 |
| ZA823701B (en) | 1983-03-30 |
| JPS57212184A (en) | 1982-12-27 |
| DK160307C (da) | 1991-07-29 |
| ES512811A0 (es) | 1983-08-01 |
| JPH0378397B2 (en, 2012) | 1991-12-13 |
| AU551695B2 (en) | 1986-05-08 |
| IE53343B1 (en) | 1988-10-26 |
| US4402970A (en) | 1983-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |