DE2328195A1 - Neue 3,6bis-(aminoacylamino)-acridine und verfahren zu ihrer herstellung - Google Patents
Neue 3,6bis-(aminoacylamino)-acridine und verfahren zu ihrer herstellungInfo
- Publication number
- DE2328195A1 DE2328195A1 DE2328195A DE2328195A DE2328195A1 DE 2328195 A1 DE2328195 A1 DE 2328195A1 DE 2328195 A DE2328195 A DE 2328195A DE 2328195 A DE2328195 A DE 2328195A DE 2328195 A1 DE2328195 A1 DE 2328195A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- acridine
- acetylamino
- yield
- general formula
- 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.)
- Pending
Links
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- ZQTINZNRBFWSKA-UHFFFAOYSA-N N-[6-[acetyl-(benzylamino)amino]acridin-3-yl]-N'-benzylacetohydrazide Chemical compound C(C1=CC=CC=C1)NN(C=1C=CC2=CC3=CC=C(C=C3N=C2C1)N(C(C)=O)NCC1=CC=CC=C1)C(C)=O ZQTINZNRBFWSKA-UHFFFAOYSA-N 0.000 description 1
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- ZLUTURLEOSNIIU-UHFFFAOYSA-N N-[6-[acetyl-(propan-2-ylamino)amino]acridin-3-yl]-N'-propan-2-ylacetohydrazide Chemical compound C(C)(C)NN(C=1C=CC2=CC3=CC=C(C=C3N=C2C=1)N(C(C)=O)NC(C)C)C(C)=O ZLUTURLEOSNIIU-UHFFFAOYSA-N 0.000 description 1
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- RUYTZUZGCDTWMP-UHFFFAOYSA-N acridine trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC=CC2=CC3=CC=CC=C3N=C21 RUYTZUZGCDTWMP-UHFFFAOYSA-N 0.000 description 1
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- 239000000783 alginic acid Substances 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
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- 235000011010 calcium phosphates Nutrition 0.000 description 1
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- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
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- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
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- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
- IZCQDRVQVRENLX-UHFFFAOYSA-N dihydrate;trihydrochloride Chemical compound O.O.Cl.Cl.Cl IZCQDRVQVRENLX-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229960001235 gentian violet Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 201000001371 inclusion conjunctivitis Diseases 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 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
- 238000004264 monolayer culture Methods 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
- VLMPDFWYWNSKMD-UHFFFAOYSA-N n-[6-[acetyl(pyrrolidin-1-yl)amino]acridin-3-yl]-n-pyrrolidin-1-ylacetamide Chemical compound C=1C=C2C=C3C=CC(N(N4CCCC4)C(C)=O)=CC3=NC2=CC=1N(C(=O)C)N1CCCC1 VLMPDFWYWNSKMD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 201000000901 ornithosis Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000001885 phytohemagglutinin Effects 0.000 description 1
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229940075065 polyvinyl acetate Drugs 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 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 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 206010044325 trachoma Diseases 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical group COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D219/08—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT487872A AT321920B (de) | 1972-06-07 | 1972-06-07 | Verfahren zur herstellung neuer 3,6-bis-(aminoacylamino)-acridine und ihrer saüreadditionssalze |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2328195A1 true DE2328195A1 (de) | 1974-01-03 |
Family
ID=3569389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2328195A Pending DE2328195A1 (de) | 1972-06-07 | 1973-06-02 | Neue 3,6bis-(aminoacylamino)-acridine und verfahren zu ihrer herstellung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3907804A (enExample) |
| JP (1) | JPS4961178A (enExample) |
| AT (1) | AT321920B (enExample) |
| BE (1) | BE800564A (enExample) |
| CA (1) | CA1001157A (enExample) |
| CH (2) | CH585721A5 (enExample) |
| DE (1) | DE2328195A1 (enExample) |
| ES (2) | ES415607A1 (enExample) |
| FR (1) | FR2187343B1 (enExample) |
| GB (1) | GB1430785A (enExample) |
| IL (1) | IL42435A (enExample) |
| NL (1) | NL7307940A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0780376A1 (de) * | 1995-12-23 | 1997-06-25 | Hoechst Aktiengesellschaft | 2-Acylamino-9-aryl-acridine, Verfahren zu ihrer Herstellung und diese enthaltende lichtempfindliche Gemische |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2704856B1 (fr) * | 1993-05-04 | 1995-08-04 | Pf Medicament | Nouveaux dérivés de la diméthylamino-3 acridine. |
-
1972
- 1972-06-07 AT AT487872A patent/AT321920B/de not_active IP Right Cessation
-
1973
- 1973-06-02 DE DE2328195A patent/DE2328195A1/de active Pending
- 1973-06-04 CH CH1375976A patent/CH585721A5/xx not_active IP Right Cessation
- 1973-06-04 CH CH801373A patent/CH585720A5/xx not_active IP Right Cessation
- 1973-06-04 US US366732A patent/US3907804A/en not_active Expired - Lifetime
- 1973-06-05 JP JP48063291A patent/JPS4961178A/ja active Pending
- 1973-06-05 IL IL42435A patent/IL42435A/en unknown
- 1973-06-06 ES ES415607A patent/ES415607A1/es not_active Expired
- 1973-06-06 GB GB2699573A patent/GB1430785A/en not_active Expired
- 1973-06-06 BE BE131971A patent/BE800564A/xx unknown
- 1973-06-06 CA CA173,379A patent/CA1001157A/en not_active Expired
- 1973-06-07 FR FR7320735A patent/FR2187343B1/fr not_active Expired
- 1973-06-07 NL NL7307940A patent/NL7307940A/xx not_active Application Discontinuation
-
1974
- 1974-03-30 ES ES424801A patent/ES424801A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0780376A1 (de) * | 1995-12-23 | 1997-06-25 | Hoechst Aktiengesellschaft | 2-Acylamino-9-aryl-acridine, Verfahren zu ihrer Herstellung und diese enthaltende lichtempfindliche Gemische |
| US5834157A (en) * | 1995-12-23 | 1998-11-10 | Agfa-Gevaert Ag | 2-acylamino-9-arylacridines, process for their preparation and photosensitive mixtures containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| ES424801A1 (es) | 1976-06-16 |
| FR2187343A1 (enExample) | 1974-01-18 |
| NL7307940A (enExample) | 1973-12-11 |
| BE800564A (fr) | 1973-12-06 |
| JPS4961178A (enExample) | 1974-06-13 |
| CH585721A5 (enExample) | 1977-03-15 |
| US3907804A (en) | 1975-09-23 |
| IL42435A (en) | 1977-04-29 |
| IL42435A0 (en) | 1973-08-29 |
| ES415607A1 (es) | 1976-02-01 |
| FR2187343B1 (enExample) | 1976-07-02 |
| CH585720A5 (enExample) | 1977-03-15 |
| GB1430785A (en) | 1976-04-07 |
| CA1001157A (en) | 1976-12-07 |
| AT321920B (de) | 1975-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |