CA1077964A - 4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compounds - Google Patents
4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compoundsInfo
- Publication number
- CA1077964A CA1077964A CA248,103A CA248103A CA1077964A CA 1077964 A CA1077964 A CA 1077964A CA 248103 A CA248103 A CA 248103A CA 1077964 A CA1077964 A CA 1077964A
- Authority
- CA
- Canada
- Prior art keywords
- oxime
- reaction
- hydrochloride
- aminoethyl
- hydrogen
- 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 title claims abstract description 100
- 230000001430 anti-depressive effect Effects 0.000 title abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000000126 substance Substances 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052801 chlorine Chemical group 0.000 claims abstract description 7
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 6
- 239000000460 chlorine Chemical group 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
- 150000002923 oximes Chemical class 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 38
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 29
- -1 propoxy, propylthio, methoxy Chemical group 0.000 claims description 28
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 22
- YHUXZWQAYFQBPG-UHFFFAOYSA-N 1-(3-chloro-4-nitrophenyl)-5-methoxypentan-1-one Chemical compound COCCCCC(=O)C1=CC=C([N+]([O-])=O)C(Cl)=C1 YHUXZWQAYFQBPG-UHFFFAOYSA-N 0.000 claims description 13
- DPTGZRADVAPUHQ-UHFFFAOYSA-N 1-(4-nitrophenyl)-2-propoxyethanone Chemical compound CCCOCC(=O)C1=CC=C([N+]([O-])=O)C=C1 DPTGZRADVAPUHQ-UHFFFAOYSA-N 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- LQCRSKSCUSXMJH-UHFFFAOYSA-N 1-(4-nitrophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 LQCRSKSCUSXMJH-UHFFFAOYSA-N 0.000 claims description 11
- VAWHTWXBNQFBAJ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.NCCON VAWHTWXBNQFBAJ-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000001530 fumaric acid Substances 0.000 claims description 8
- FMHFXXRKMQWBEP-UHFFFAOYSA-N 1-(3-methyl-4-nitrophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C([N+]([O-])=O)C(C)=C1 FMHFXXRKMQWBEP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Chemical group 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- IVLJDGSFPOBAID-UHFFFAOYSA-N 5-methoxy-1-(4-nitrophenyl)pentan-1-one Chemical compound COCCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 IVLJDGSFPOBAID-UHFFFAOYSA-N 0.000 claims description 5
- PXSLNRQFXCFEAY-UHFFFAOYSA-N 6-methoxy-1-(4-nitrophenyl)hexan-1-one Chemical compound COCCCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 PXSLNRQFXCFEAY-UHFFFAOYSA-N 0.000 claims description 5
- LAAQSOCEYYDGGG-UHFFFAOYSA-N o-(2-aminopropyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CC(N)CON LAAQSOCEYYDGGG-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- AVMPRGQRQKZCHO-UHFFFAOYSA-N 5-(2-methoxyethoxy)-1-(4-nitrophenyl)pentan-1-one Chemical compound COCCOCCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 AVMPRGQRQKZCHO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
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- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- WJQSTKOKOAWURI-UHFFFAOYSA-N CCCCC(=S)C1=CC=C([N+]([O-])=O)C=C1 Chemical compound CCCCC(=S)C1=CC=C([N+]([O-])=O)C=C1 WJQSTKOKOAWURI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003544 oxime group Chemical group 0.000 claims description 3
- ODSCUBSJIFLFPF-UHFFFAOYSA-N 1-(4-aminophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C(N)C=C1 ODSCUBSJIFLFPF-UHFFFAOYSA-N 0.000 claims description 2
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- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 claims description 2
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- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 14
- 239000007858 starting material Substances 0.000 claims 12
- JPXNWSUZNNOPCE-UHFFFAOYSA-N 2-[1-(4-nitrophenyl)pentylideneamino]oxy-n-tritylethanamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(CCCC)=NOCCNC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JPXNWSUZNNOPCE-UHFFFAOYSA-N 0.000 claims 1
- QPXXCHSNRHEJGT-UHFFFAOYSA-N n-[1-(4-nitrophenyl)-2-propoxyethylidene]hydroxylamine Chemical compound CCCOCC(=NO)C1=CC=C([N+]([O-])=O)C=C1 QPXXCHSNRHEJGT-UHFFFAOYSA-N 0.000 claims 1
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- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 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 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/58—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/10—Sulfenic acids; Esters thereof
- C07C313/12—Sulfenic acids; Esters thereof having sulfur atoms of sulfenic groups bound to acyclic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7503307A NL7503307A (nl) | 1975-03-20 | 1975-03-20 | Antidepressieve verbindingen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077964A true CA1077964A (en) | 1980-05-20 |
Family
ID=19823421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,103A Expired CA1077964A (en) | 1975-03-20 | 1976-03-17 | 4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compounds |
Country Status (21)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7256191B2 (en) | 2000-04-24 | 2007-08-14 | Aryx Therapeutics | Materials and methods for the treatment of depression |
| AU5565401A (en) | 2000-04-24 | 2001-11-07 | Aryx Therapeutics | Materials and methods for the treatment of depression |
-
1975
- 1975-03-20 NL NL7503307A patent/NL7503307A/xx not_active Application Discontinuation
-
1976
- 1976-03-08 ZA ZA761386A patent/ZA761386B/xx unknown
- 1976-03-12 DE DE2610302A patent/DE2610302A1/de not_active Withdrawn
- 1976-03-17 PL PL1976188001A patent/PL100612B1/pl unknown
- 1976-03-17 PL PL1976199546A patent/PL100040B1/pl unknown
- 1976-03-17 HU HU76PI00000515A patent/HU171160B/hu unknown
- 1976-03-17 IL IL49236A patent/IL49236A/xx unknown
- 1976-03-17 DD DD7600191890A patent/DD128331A5/xx unknown
- 1976-03-17 AT AT195276A patent/AT340894B/de not_active IP Right Cessation
- 1976-03-17 GB GB10706/76A patent/GB1533063A/en not_active Expired
- 1976-03-17 GR GR50330A patent/GR60051B/el unknown
- 1976-03-17 FI FI760696A patent/FI760696A7/fi not_active Application Discontinuation
- 1976-03-17 DK DK115676A patent/DK115676A/da unknown
- 1976-03-17 SE SE7603344A patent/SE7603344L/xx not_active Application Discontinuation
- 1976-03-17 CA CA248,103A patent/CA1077964A/en not_active Expired
- 1976-03-17 PL PL1976199547A patent/PL101882B1/pl unknown
- 1976-03-18 ES ES446189A patent/ES446189A1/es not_active Expired
- 1976-03-18 BE BE165313A patent/BE839741A/xx unknown
- 1976-03-18 IE IE570/76A patent/IE43826B1/en unknown
- 1976-03-18 AU AU12142/76A patent/AU502701B2/en not_active Expired
- 1976-03-19 FR FR7608015A patent/FR2304332A1/fr active Granted
- 1976-03-19 AR AR262633A patent/AR212811A1/es active
- 1976-03-19 JP JP51029391A patent/JPS51125344A/ja active Pending
- 1976-12-07 AR AR265765A patent/AR213298A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| DD128331A5 (de) | 1977-11-09 |
| ATA195276A (de) | 1977-05-15 |
| GR60051B (en) | 1978-04-04 |
| FR2304332B1 (enrdf_load_html_response) | 1978-12-08 |
| ZA761386B (en) | 1977-10-26 |
| SE7603344L (sv) | 1976-09-21 |
| HU171160B (hu) | 1977-11-28 |
| IE43826L (en) | 1976-09-20 |
| IE43826B1 (en) | 1981-06-03 |
| AT340894B (de) | 1978-01-10 |
| DE2610302A1 (de) | 1976-09-30 |
| IL49236A0 (en) | 1976-05-31 |
| PL100612B1 (pl) | 1978-10-31 |
| IL49236A (en) | 1978-08-31 |
| ES446189A1 (es) | 1977-10-01 |
| FI760696A7 (enrdf_load_html_response) | 1976-09-21 |
| AU1214276A (en) | 1977-09-22 |
| NL7503307A (nl) | 1976-09-22 |
| FR2304332A1 (fr) | 1976-10-15 |
| AU502701B2 (en) | 1979-08-02 |
| AR213298A1 (es) | 1979-01-15 |
| PL100040B1 (pl) | 1978-08-31 |
| PL101882B1 (pl) | 1979-02-28 |
| AR212811A1 (es) | 1978-10-13 |
| GB1533063A (en) | 1978-11-22 |
| DK115676A (da) | 1976-09-21 |
| BE839741A (fr) | 1976-09-20 |
| JPS51125344A (en) | 1976-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |