DE2251559C2 - 5,6-Dihydro-pyrrolo[3,4-b]pyridinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen - Google Patents
5,6-Dihydro-pyrrolo[3,4-b]pyridinderivate, Verfahren zu ihrer Herstellung und pharmazeutische ZusammensetzungenInfo
- Publication number
- DE2251559C2 DE2251559C2 DE2251559A DE2251559A DE2251559C2 DE 2251559 C2 DE2251559 C2 DE 2251559C2 DE 2251559 A DE2251559 A DE 2251559A DE 2251559 A DE2251559 A DE 2251559A DE 2251559 C2 DE2251559 C2 DE 2251559C2
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- ecm
- pyrrolo
- pyridine
- 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 7
- SJMNQXLXIIXDDS-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[3,4-b]pyridine Chemical class C1=CC=C2CNCC2=N1 SJMNQXLXIIXDDS-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- -1 alkali metal salt Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000011514 reflex Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 4
- 229960004782 chlordiazepoxide Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- ZRKGTINFVOLLNT-UHFFFAOYSA-N pyrrolo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)NC(=O)C2=N1 ZRKGTINFVOLLNT-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003204 tranquilizing agent Substances 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000002232 neuromuscular Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 210000000457 tarsus Anatomy 0.000 description 2
- 210000002972 tibial nerve Anatomy 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 229940125725 tranquilizer Drugs 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7138045A FR2156488B1 (OSRAM) | 1971-10-22 | 1971-10-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2251559A1 DE2251559A1 (de) | 1973-04-26 |
| DE2251559C2 true DE2251559C2 (de) | 1986-05-22 |
Family
ID=9084771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2251559A Expired DE2251559C2 (de) | 1971-10-22 | 1972-10-20 | 5,6-Dihydro-pyrrolo[3,4-b]pyridinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3853880A (OSRAM) |
| JP (2) | JPS555515B2 (OSRAM) |
| AT (1) | AT317898B (OSRAM) |
| AU (1) | AU468852B2 (OSRAM) |
| BE (1) | BE790408A (OSRAM) |
| CA (1) | CA963471A (OSRAM) |
| CH (2) | CH551429A (OSRAM) |
| DE (1) | DE2251559C2 (OSRAM) |
| DK (1) | DK138690B (OSRAM) |
| FR (1) | FR2156488B1 (OSRAM) |
| GB (1) | GB1361128A (OSRAM) |
| IE (1) | IE37220B1 (OSRAM) |
| NL (1) | NL175916C (OSRAM) |
| SE (1) | SE384026B (OSRAM) |
| ZA (1) | ZA727468B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR208414A1 (es) * | 1974-11-07 | 1976-12-27 | Rhone Poulenc Ind | Procedimiento para obtener nuevos derivados de la((acil-4piperazinil-1)carboniloxi-5 pirrolinona-2) |
| ATE39483T1 (de) * | 1982-04-02 | 1989-01-15 | Takeda Chemical Industries Ltd | Kondensierte pyrrolinon-derivate, und ihre herstellung. |
| GB8610980D0 (en) * | 1986-05-06 | 1986-06-11 | Ici America Inc | Heterocyclic fused tricyclic compounds |
| US4866074A (en) * | 1987-05-08 | 1989-09-12 | Rorer Pharmaceutical Corporation | Naphtheridinone- and pyridooxazinone-pyridone compounds, cardiotonic compositions including same, and their uses |
| DE10042093A1 (de) * | 2000-08-26 | 2002-03-07 | Dresden Arzneimittel | Antikonvulsiv wirkende 6,7-Dihydro-pyrrolo[3,4-d]pyridin-5-one und Verfahren zu deren Darstellung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3100776A (en) * | 1961-06-02 | 1963-08-13 | Mcneilab Inc | Novel 2-r3-3a,4,7a-tetrahydro-4,7-(r1,r2-y)-r4-isoindolines and the corresponding 3a,4,5,6,7,7a-hexahydro compounds |
| US3198798A (en) * | 1962-11-02 | 1965-08-03 | Sterling Drug Inc | Phthalimido- and isoindolinyl-alkylpiperazines and their preparation |
| US3635976A (en) * | 1967-12-20 | 1972-01-18 | Pennwalt Corp | 1 - heterocyclic alkyl-1 2 3 4-tetrahydroquinazolinones and analgesic intermediates thereof |
-
0
- BE BE790408D patent/BE790408A/xx not_active IP Right Cessation
-
1971
- 1971-10-22 FR FR7138045A patent/FR2156488B1/fr not_active Expired
-
1972
- 1972-10-13 NL NLAANVRAGE7213901,A patent/NL175916C/xx not_active IP Right Cessation
- 1972-10-19 GB GB4826772A patent/GB1361128A/en not_active Expired
- 1972-10-19 AU AU47969/72A patent/AU468852B2/en not_active Expired
- 1972-10-19 US US00299167A patent/US3853880A/en not_active Expired - Lifetime
- 1972-10-20 JP JP10458872A patent/JPS555515B2/ja not_active Expired
- 1972-10-20 CH CH1538772A patent/CH551429A/fr not_active IP Right Cessation
- 1972-10-20 IE IE1424/72A patent/IE37220B1/xx unknown
- 1972-10-20 CA CA154,648*7A patent/CA963471A/en not_active Expired
- 1972-10-20 CH CH495574A patent/CH551431A/fr not_active IP Right Cessation
- 1972-10-20 ZA ZA727468A patent/ZA727468B/xx unknown
- 1972-10-20 SE SE7213619A patent/SE384026B/xx unknown
- 1972-10-20 DK DK523272AA patent/DK138690B/da unknown
- 1972-10-20 DE DE2251559A patent/DE2251559C2/de not_active Expired
- 1972-10-23 AT AT903372A patent/AT317898B/de not_active IP Right Cessation
-
1979
- 1979-07-23 JP JP9272779A patent/JPS5522675A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| AU468852B2 (en) | 1976-01-22 |
| NL7213901A (OSRAM) | 1973-04-25 |
| IE37220B1 (en) | 1977-06-08 |
| ZA727468B (en) | 1973-07-25 |
| JPS5522675A (en) | 1980-02-18 |
| CA963471A (en) | 1975-02-25 |
| CH551431A (fr) | 1974-07-15 |
| CH551429A (fr) | 1974-07-15 |
| DK138690C (OSRAM) | 1979-03-26 |
| BE790408A (fr) | 1973-04-20 |
| FR2156488A1 (OSRAM) | 1973-06-01 |
| IE37220L (en) | 1973-04-22 |
| GB1361128A (en) | 1974-07-24 |
| FR2156488B1 (OSRAM) | 1975-11-28 |
| JPS5614111B2 (OSRAM) | 1981-04-02 |
| JPS4849790A (OSRAM) | 1973-07-13 |
| JPS555515B2 (OSRAM) | 1980-02-07 |
| NL175916B (nl) | 1984-08-16 |
| SE384026B (sv) | 1976-04-12 |
| AT317898B (de) | 1974-09-25 |
| DE2251559A1 (de) | 1973-04-26 |
| AU4796972A (en) | 1974-04-26 |
| DK138690B (da) | 1978-10-16 |
| US3853880A (en) | 1974-12-10 |
| NL175916C (nl) | 1985-01-16 |
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