HU190854B - Process for production of 3-aril-7-clor-3,4-hydroacridine-1,9-/2h, 10h/-dion - 1-oxims and-1-hydrazon derivates and medicaments containing them - Google Patents
Process for production of 3-aril-7-clor-3,4-hydroacridine-1,9-/2h, 10h/-dion - 1-oxims and-1-hydrazon derivates and medicaments containing them Download PDFInfo
- Publication number
- HU190854B HU190854B HU833500A HU350083A HU190854B HU 190854 B HU190854 B HU 190854B HU 833500 A HU833500 A HU 833500A HU 350083 A HU350083 A HU 350083A HU 190854 B HU190854 B HU 190854B
- Authority
- HU
- Hungary
- Prior art keywords
- chloro
- compound
- formula
- dione
- dihydroacridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 239000003814 drug Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 48
- -1 iminocarbonyl Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- IYPZRUYMFDWKSS-UHFFFAOYSA-N piperazin-1-amine Chemical compound NN1CCNCC1 IYPZRUYMFDWKSS-UHFFFAOYSA-N 0.000 claims description 6
- XAOHWSFGKCJOGT-UHFFFAOYSA-N 2-(4-aminopiperazin-1-yl)ethanol Chemical compound NN1CCN(CCO)CC1 XAOHWSFGKCJOGT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- PZRVZMZUBQJOQW-UHFFFAOYSA-N 7-chloro-3-[4-(trifluoromethyl)phenyl]-2,3,4,10-tetrahydroacridine-1,9-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1C1CC(NC=2C(=CC(Cl)=CC=2)C2=O)=C2C(=O)C1 PZRVZMZUBQJOQW-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- GILZXVOUYJEQSM-UHFFFAOYSA-N 7-chloro-3-(4-chlorophenyl)-2,3,4,10-tetrahydroacridine-1,9-dione Chemical compound C1=CC(Cl)=CC=C1C1CC(NC=2C(=CC(Cl)=CC=2)C2=O)=C2C(=O)C1 GILZXVOUYJEQSM-UHFFFAOYSA-N 0.000 claims 2
- 150000004885 piperazines Chemical group 0.000 claims 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
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- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 description 23
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 150000007857 hydrazones Chemical class 0.000 description 7
- 150000002923 oximes Chemical class 0.000 description 7
- AWHZKKVSUJJVNL-UHFFFAOYSA-N 7-chloro-10-hydroxy-3-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2h-acridine-1,9-dione Chemical compound C1C(=O)C=2C(=O)C3=CC(Cl)=CC=C3N(O)C=2CC1C1=CC=C(C(F)(F)F)C=C1 AWHZKKVSUJJVNL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 229940125782 compound 2 Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
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- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 2
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- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
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- ANNHHDONMUBVSB-UHFFFAOYSA-N n,n-diethyl-2-hydrazinylethanamine Chemical compound CCN(CC)CCNN ANNHHDONMUBVSB-UHFFFAOYSA-N 0.000 description 2
- SUUAFMDPHOXPLM-UHFFFAOYSA-N n-amino-n-(diethylamino)acetamide Chemical compound CCN(CC)N(N)C(C)=O SUUAFMDPHOXPLM-UHFFFAOYSA-N 0.000 description 2
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
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- DJTIANXYHUNHQV-UHFFFAOYSA-N 1,1-dibutylhydrazine Chemical compound CCCCN(N)CCCC DJTIANXYHUNHQV-UHFFFAOYSA-N 0.000 description 1
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- NRYJIKFQAFBQJF-UHFFFAOYSA-N o-(2-morpholin-4-ylethyl)hydroxylamine Chemical compound NOCCN1CCOCC1 NRYJIKFQAFBQJF-UHFFFAOYSA-N 0.000 description 1
- YOUVHXQKCSEVSP-UHFFFAOYSA-N o-(2-piperidin-1-ylethyl)hydroxylamine Chemical compound NOCCN1CCCCC1 YOUVHXQKCSEVSP-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZAMCTDDIJFNXOH-UHFFFAOYSA-N tributylazanium;acetate Chemical compound CC(O)=O.CCCCN(CCCC)CCCC ZAMCTDDIJFNXOH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823237649 DE3237649A1 (de) | 1982-10-11 | 1982-10-11 | 3-aryl-7-chlor-10-hydroxy-3,4-dihydro-acridin-1,9-(2h, 10h)-dion-1-oxime und -1-hydrazonderivate, deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| DE19823247908 DE3247908A1 (de) | 1982-12-24 | 1982-12-24 | 3-aryl-7-chlor-3,4-dihydro-acridin-1,9-(2h,-10h)-dion-1-oxime und -1-hydrazonderivate, deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU190854B true HU190854B (en) | 1986-11-28 |
Family
ID=25805046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU833500A HU190854B (en) | 1982-10-11 | 1983-10-10 | Process for production of 3-aril-7-clor-3,4-hydroacridine-1,9-/2h, 10h/-dion - 1-oxims and-1-hydrazon derivates and medicaments containing them |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4593027A (enExample) |
| EP (1) | EP0106284B1 (enExample) |
| AU (1) | AU561449B2 (enExample) |
| CA (1) | CA1217491A (enExample) |
| DE (1) | DE3372094D1 (enExample) |
| DK (1) | DK465583A (enExample) |
| ES (1) | ES526354A0 (enExample) |
| FI (1) | FI833651A7 (enExample) |
| GR (1) | GR78732B (enExample) |
| HU (1) | HU190854B (enExample) |
| IL (1) | IL69941A (enExample) |
| JO (1) | JO1266B1 (enExample) |
| MA (1) | MA19925A1 (enExample) |
| NO (1) | NO833681L (enExample) |
| NZ (1) | NZ205906A (enExample) |
| PH (1) | PH19108A (enExample) |
| PT (1) | PT77476B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4626540A (en) * | 1983-11-08 | 1986-12-02 | Warner-Lambert Company | Substituted 1-amino-4-nitro-acridinones and methods of treating bacterial infections and leukemia with them |
| IN164921B (enExample) * | 1986-07-22 | 1989-07-08 | Hoechst India | |
| US5180717A (en) * | 1988-08-16 | 1993-01-19 | The Upjohn Company | Bivalent ligands effective for blocking ACAT enzyme for lowering plasma triglycerides and for elevating HDL cholesterol |
| US5182303A (en) * | 1988-12-27 | 1993-01-26 | E. I. Du Pont De Nemours And Company | Substituted semicarbazone arthropodicides |
| US5268388A (en) * | 1988-12-27 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Substituted semicarbazone arthropodicides |
| US5859028A (en) * | 1997-04-28 | 1999-01-12 | Potomax Limited Partnership | Carotenoid synthesis inhibiting herbicides and fatty acid synthesis inhibiting oxime herbicides as anti-Apicomplexa protozoan parasite agents |
| US20090324580A1 (en) * | 2006-03-09 | 2009-12-31 | Cenix Bioscience Gmbh | Use of Inhibitors of Scavenger Receptor Class Proteins for the Treatment of Infectious Diseases |
| CA2673683C (en) | 2007-01-11 | 2014-07-29 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| EP2225226B1 (en) | 2007-12-26 | 2016-08-17 | Critical Outcome Technologies, Inc. | Compounds and their use in a method for treatment of cancer |
| WO2010006438A1 (en) | 2008-07-17 | 2010-01-21 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| CA2794952C (en) | 2010-04-01 | 2018-05-15 | Critical Outcome Technologies Inc. | Compounds and method for treatment of hiv |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2880210A (en) * | 1959-03-31 | Acridine n-oxides | ||
| US3184452A (en) * | 1965-05-18 | New aminoalkoxy compounds and process for theik manufacture | ||
| NL132832C (enExample) * | 1961-05-26 | |||
| US3577558A (en) * | 1968-04-15 | 1971-05-04 | Sterling Drug Inc | 1-aminoalkylamino-4-alkoxymethylthioxanthene derivatives |
| DE1811409A1 (de) * | 1968-11-28 | 1970-06-18 | Bayer Ag | Mittel zur Bekaempfung von Insekten,Milben,Hasenartigen und Nagetieren |
| DE2337474C2 (de) * | 1973-07-24 | 1982-01-21 | Hoechst Ag, 6000 Frankfurt | Chemotherapeutisch wirksame Tetrahydroacridone, Verfahren zu ihrer Herstellung und sie enthaltende Mittel |
| DE2651084A1 (de) * | 1976-11-09 | 1978-12-14 | Hoechst Ag | Basisch substituirte o-(2-hydroxypropyl) -aldoxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE2748333A1 (de) * | 1977-10-28 | 1979-05-03 | Hoechst Ag | Mittel gegen malaria |
| US4178451A (en) * | 1978-07-13 | 1979-12-11 | E. R. Squibb & Sons, Inc. | 3-(Substituted hydrazino)benzisothiazole-1,1-dioxides |
| US4266062A (en) * | 1978-09-18 | 1981-05-05 | Mcneilab, Inc. | (1-Methyl-2-pyridinylidene) derivatives of guanidine |
| US4447427A (en) * | 1979-01-04 | 1984-05-08 | The United States Of America As Represented By The Secretary Of The Army | Method for treating bacterial infections with 2-acetyl- and 2-propionylpyridine thiosemicarbazones |
| US4291034A (en) * | 1980-03-20 | 1981-09-22 | Warner Lambert Company | 7-Chloro-3-substituted aryl-3,4-dihydro-1,9(2H,10H) and 10 hydroxy acridinedioneimines having antimalarial activity |
| US4440771A (en) * | 1982-02-12 | 1984-04-03 | The United States Of America As Represented By The Secretary Of The Army | 2-Acetyl quinoline thiosemicarbazones useful in treatment of gonorrhea, malaria or bacterial infections |
-
1983
- 1983-10-07 EP EP83110035A patent/EP0106284B1/de not_active Expired
- 1983-10-07 FI FI833651A patent/FI833651A7/fi not_active Application Discontinuation
- 1983-10-07 CA CA000438636A patent/CA1217491A/en not_active Expired
- 1983-10-07 DE DE8383110035T patent/DE3372094D1/de not_active Expired
- 1983-10-10 HU HU833500A patent/HU190854B/hu not_active IP Right Cessation
- 1983-10-10 IL IL69941A patent/IL69941A/xx unknown
- 1983-10-10 DK DK465583A patent/DK465583A/da not_active Application Discontinuation
- 1983-10-10 NO NO833681A patent/NO833681L/no unknown
- 1983-10-10 ES ES526354A patent/ES526354A0/es active Granted
- 1983-10-10 NZ NZ205906A patent/NZ205906A/en unknown
- 1983-10-10 GR GR72653A patent/GR78732B/el unknown
- 1983-10-10 MA MA20145A patent/MA19925A1/fr unknown
- 1983-10-10 PT PT77476A patent/PT77476B/pt unknown
- 1983-10-10 PH PH29680A patent/PH19108A/en unknown
- 1983-10-10 AU AU20004/83A patent/AU561449B2/en not_active Ceased
- 1983-10-11 US US06/540,647 patent/US4593027A/en not_active Expired - Fee Related
- 1983-10-11 JO JO19831266A patent/JO1266B1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DK465583D0 (da) | 1983-10-10 |
| ES8405616A1 (es) | 1984-06-16 |
| JO1266B1 (en) | 1985-04-20 |
| CA1217491A (en) | 1987-02-03 |
| AU2000483A (en) | 1984-04-19 |
| EP0106284A1 (de) | 1984-04-25 |
| FI833651A7 (fi) | 1984-04-12 |
| US4593027A (en) | 1986-06-03 |
| NO833681L (no) | 1984-04-12 |
| ES526354A0 (es) | 1984-06-16 |
| MA19925A1 (fr) | 1984-07-01 |
| EP0106284B1 (de) | 1987-06-16 |
| FI833651A0 (fi) | 1983-10-07 |
| DK465583A (da) | 1984-04-12 |
| PH19108A (en) | 1986-01-06 |
| NZ205906A (en) | 1986-06-11 |
| IL69941A (en) | 1988-06-30 |
| GR78732B (enExample) | 1984-10-02 |
| DE3372094D1 (en) | 1987-07-23 |
| PT77476B (de) | 1986-04-16 |
| AU561449B2 (en) | 1987-05-07 |
| IL69941A0 (en) | 1984-01-31 |
| PT77476A (de) | 1983-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |