GB1147295A - Process for the production of bis-quaternary ammonium compounds - Google Patents
Process for the production of bis-quaternary ammonium compoundsInfo
- Publication number
- GB1147295A GB1147295A GB49897/67A GB4989767A GB1147295A GB 1147295 A GB1147295 A GB 1147295A GB 49897/67 A GB49897/67 A GB 49897/67A GB 4989767 A GB4989767 A GB 4989767A GB 1147295 A GB1147295 A GB 1147295A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- formula
- group
- alkyl
- reacting
- 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
- 229940083122 ganglion-blocking antiandrenergic bisquaternary ammonium compound Drugs 0.000 title abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- -1 sulphonamido Chemical group 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000005521 carbonamide group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000013256 coordination polymer Substances 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005549 heteroarylene group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 230000000654 trypanocidal effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,147,295. Bis-quaternary ammonium compounds. FARBENFABRIKEN BAYER A.G. 2 Nov., 1967 [3 Nov., 1966; 24 July, 1967], No. 49897/67. Heading C2C. Novel bis-quaternary ammonium compounds of the formula is a pyridine, quinoline, isoquinoline, indolenine, benzoxazole, benzothiazole, benzimidazole or acridine ring which is unsubstituted or substituted by at least one halogen atom, or an alkyl, aryl, alkoxy, alkylmercapto, nitro, acylamino, carbonamido, carbalkoxy, sulphonamido, alkylsulphone or trifluoromethyl group or groups; R is alkyl; R<SP>1</SP> and R<SP>11</SP>, which may be the same or different, are hydrogen or alkyl; X is the radical of an inorganic or organic acid; Y is a saturated or unsaturated alkylene, arylene, cycloalkylene, aralkylene, hexahydroaralkylene or heteroarylene group which is unsubstituted or substituted by at least one halogen atom or an alkyl, aryl, alkoxy, alkylmercapto, hydroxyalkyl, haloalkyl, nitro, substituted or unsubstituted amino, carbalkoxy, carbonamide, sulphonamide or alkylsulphone group or groups; and n is 0 or 1 are prepared by reacting (a) the corresponding bis-substituted dicarboxylic acid diamide or bis-urea obtained from the appropriate amino-heterocyclic compound and either a compound of the formula CP.OCYCOCP or one of the formula OCN-YNCO with a reactive ester RX; or (b) the corresponding quaternary amino heterocyclic compound with a reactive derivative of a dicarboxylic acid of the formula in which Z is an atom or group reacting with the group N(R<SP>1</SP>)H with the elimination of HZ; or (c) when n is 1 and R<SP>11</SP> is hydrogen, reacting the corresponding quaternary amino-heterocyclic compound with a bis-isocyanate of the formula OCN-Y-NCO; or (d) when n is 1 and R<SP>1</SP> is hydrogen, reacting the corresponding quaternary isocyanato-heterocyclic compound with a diamine of the formula Pharmaceutical compositions, having trypanocidal and/or cytostatic activity, contain at least one of the above novel bis-quaternary ammonium compounds or the active ingredient.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0050597 | 1966-11-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1147295A true GB1147295A (en) | 1969-04-02 |
Family
ID=7103922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49897/67A Expired GB1147295A (en) | 1966-11-03 | 1967-11-02 | Process for the production of bis-quaternary ammonium compounds |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR7220M (en) |
| GB (1) | GB1147295A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5142056A (en) * | 1989-05-23 | 1992-08-25 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| WO2007022258A1 (en) * | 2005-08-17 | 2007-02-22 | Schering Corporation | Novel high affinity thiophene-based and furan-based kinase ligands |
| US7482352B2 (en) | 2001-03-23 | 2009-01-27 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agents |
-
1967
- 1967-11-02 GB GB49897/67A patent/GB1147295A/en not_active Expired
-
1968
- 1968-02-02 FR FR138594A patent/FR7220M/fr not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5142056A (en) * | 1989-05-23 | 1992-08-25 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| US7482352B2 (en) | 2001-03-23 | 2009-01-27 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agents |
| WO2007022258A1 (en) * | 2005-08-17 | 2007-02-22 | Schering Corporation | Novel high affinity thiophene-based and furan-based kinase ligands |
| US7446195B2 (en) | 2005-08-17 | 2008-11-04 | Schering Corporation | High affinity thiophene-based and furan-based kinase ligands |
| JP2009504756A (en) * | 2005-08-17 | 2009-02-05 | シェーリング コーポレイション | Novel high-affinity thiophene-based and furan-based kinase ligands |
Also Published As
| Publication number | Publication date |
|---|---|
| FR7220M (en) | 1969-08-25 |
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