GB924961A - Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof - Google Patents
Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereofInfo
- Publication number
- GB924961A GB924961A GB8878/59A GB887859A GB924961A GB 924961 A GB924961 A GB 924961A GB 8878/59 A GB8878/59 A GB 8878/59A GB 887859 A GB887859 A GB 887859A GB 924961 A GB924961 A GB 924961A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- alkoxy
- phenyl ring
- compounds
- benzyl
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 title 1
- -1 hydroxy, formyl Chemical group 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 2
- 239000002168 alkylating agent Substances 0.000 abstract 2
- 229940100198 alkylating agent Drugs 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- QRVRYBJTVILKOK-UHFFFAOYSA-N 1-[4-(2-bromoethoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(OCCBr)C=C1 QRVRYBJTVILKOK-UHFFFAOYSA-N 0.000 abstract 1
- PMVNVIGEOVZRTJ-UHFFFAOYSA-N 1-bromo-2-(2-chloroethoxymethyl)benzene Chemical compound ClCCOCC1=CC=CC=C1Br PMVNVIGEOVZRTJ-UHFFFAOYSA-N 0.000 abstract 1
- LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 abstract 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 abstract 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 abstract 1
- RHPLYFZTWLENEV-UHFFFAOYSA-N 2-[(2-bromophenyl)methoxy]ethanol Chemical compound OCCOCC1=CC=CC=C1Br RHPLYFZTWLENEV-UHFFFAOYSA-N 0.000 abstract 1
- YTZWQUYIRHGHMJ-UHFFFAOYSA-N 3-(1,2-diamino-2-phenylethenyl)benzene-1,2-disulfonic acid Chemical compound NC(=C(C1=C(C(=CC=C1)S(=O)(=O)O)S(=O)(=O)O)N)C1=CC=CC=C1 YTZWQUYIRHGHMJ-UHFFFAOYSA-N 0.000 abstract 1
- UCHDVTOVFHVWOS-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methylsulfanyl]thiophene-2-carboxylic acid Chemical group S1C=CC(SCC=2C=C(Cl)C(Cl)=CC=2)=C1C(=O)O UCHDVTOVFHVWOS-UHFFFAOYSA-N 0.000 abstract 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 abstract 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 206010061217 Infestation Diseases 0.000 abstract 1
- 241000244206 Nematoda Species 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 238000005349 anion exchange Methods 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- QJFJAMTYTQPPMU-UHFFFAOYSA-N benzyl-[2-[2-(4-tert-butylphenoxy)ethoxy]ethyl]-dimethylazanium Chemical compound C(C)(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1 QJFJAMTYTQPPMU-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- PNKGVPLMWAEASD-UHFFFAOYSA-N piperazine-1,4-dicarbodithioic acid Chemical compound SC(=S)N1CCN(C(S)=S)CC1 PNKGVPLMWAEASD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A41—WEARING APPAREL
- A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
- A41D27/00—Details of garments or of their making
- A41D27/02—Linings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/28—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE588558D BE588558A (enrdf_load_stackoverflow) | 1959-03-13 | ||
| FR837356A FR558M (enrdf_load_stackoverflow) | 1959-03-13 | ||
| GB8878/59A GB924961A (en) | 1959-03-13 | 1959-03-13 | Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof |
| ES0256264A ES256264A1 (es) | 1959-03-13 | 1960-03-04 | Un metodo para la preparaciën de compuestos de amonio cuaternario |
| GR600129331A GR29331B (el) | 1959-03-13 | 1960-03-08 | Μεθοδος παρασκευης τεταρτοταγων αμμωνιακων ενωσεων. |
| CH270760A CH422758A (de) | 1959-03-13 | 1960-03-10 | Verfahren zur Herstellung neuer quaternärer Ammoniumverbindungen |
| CH1658665A CH436259A (de) | 1959-03-13 | 1960-03-10 | Verfahren zur Herstellung quaternärer Ammoniumverbindungen |
| NL249341A NL129619C (enrdf_load_stackoverflow) | 1959-03-13 | 1960-03-11 | |
| LU38374D LU38374A1 (enrdf_load_stackoverflow) | 1959-03-13 | 1960-03-11 | |
| FR821114A FR1421206A (fr) | 1959-03-13 | 1960-03-11 | Composés d'ammonium quaternaires, en particulier portant un groupe phénoxyéthylique éventuellement substitué, et leur préparation |
| DK97360A DK104353C (da) | 1959-03-13 | 1960-03-12 | Fremgangsmåde til fremstilling af kvaternære ammoniumforbindelser. |
| DE1960W0027453 DE1238485C2 (de) | 1959-03-13 | 1960-03-14 | Verfahren zur Herstellung von quartaeren Ammoniumsalzen |
| NL6909922A NL6909922A (enrdf_load_stackoverflow) | 1959-03-13 | 1969-06-27 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8878/59A GB924961A (en) | 1959-03-13 | 1959-03-13 | Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof |
| GB887959 | 1959-03-13 | ||
| GB3955859 | 1959-11-20 | ||
| GB3955959 | 1959-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB924961A true GB924961A (en) | 1963-05-01 |
Family
ID=27447685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8878/59A Expired GB924961A (en) | 1959-03-13 | 1959-03-13 | Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE588558A (enrdf_load_stackoverflow) |
| CH (2) | CH436259A (enrdf_load_stackoverflow) |
| DE (1) | DE1238485C2 (enrdf_load_stackoverflow) |
| DK (1) | DK104353C (enrdf_load_stackoverflow) |
| ES (1) | ES256264A1 (enrdf_load_stackoverflow) |
| FR (2) | FR1421206A (enrdf_load_stackoverflow) |
| GB (1) | GB924961A (enrdf_load_stackoverflow) |
| GR (1) | GR29331B (enrdf_load_stackoverflow) |
| LU (1) | LU38374A1 (enrdf_load_stackoverflow) |
| NL (2) | NL129619C (enrdf_load_stackoverflow) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49101519A (enrdf_load_stackoverflow) * | 1973-01-18 | 1974-09-25 | ||
| US3956369A (en) * | 1973-05-18 | 1976-05-11 | Ozeretskovskaya Natalia Nikola | N-β-(2-acetyl-4-chlorophenoxy)-ethyl-N,N-dimethyl-N-benzyl-ammonium-p-chlorobenzene sulphonate, method for preparing same and medicinal preparation based thereon |
| EP0103252A3 (de) * | 1982-09-11 | 1984-10-03 | BASF Aktiengesellschaft | Aryloxyalkylamine, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
| WO1995011238A1 (en) * | 1993-10-22 | 1995-04-27 | Smithkline Beecham Plc | Heterocyclic amines for treating ischaemic strokes |
| WO1995011240A1 (en) * | 1993-10-22 | 1995-04-27 | Smithkline Beecham Plc | Amine derivatives as calcium channel antagonists |
| EP0978512A1 (en) * | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| US7256312B2 (en) | 2002-08-01 | 2007-08-14 | Basf Aktiengesellschaft | Method for producing aminoalkoxy benzylamines and aminoalkoxy benzonitriles as intermediates |
| WO2012040133A3 (en) * | 2010-09-21 | 2012-05-10 | Ge Healthcare Limited | Novel precursors of radiolabelled choline analog compounds |
| JP2023517604A (ja) * | 2020-03-11 | 2023-04-26 | ノシオン セラピューティクス，インコーポレイテッド | 荷電したイオンチャンネル遮断薬および使用方法 |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53144554A (en) * | 1977-04-12 | 1978-12-15 | Nattermann A & Cie | New basic paraabenzoylether |
| DE2913523A1 (de) | 1979-04-04 | 1980-10-23 | Basf Ag | Substituierte alkylammoniumsalze, ihre herstellung und verwendung zur regulierung des pflanzenwachstums |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1117600B (de) * | 1956-03-29 | 1961-11-23 | Wellcome Found | Verfahren zur Herstellung von gegen Nematoden wirksamen quaternaeren Ammoniumsalzen |
-
0
- FR FR837356A patent/FR558M/fr not_active Expired
- BE BE588558D patent/BE588558A/xx unknown
-
1959
- 1959-03-13 GB GB8878/59A patent/GB924961A/en not_active Expired
-
1960
- 1960-03-04 ES ES0256264A patent/ES256264A1/es not_active Expired
- 1960-03-08 GR GR600129331A patent/GR29331B/el unknown
- 1960-03-10 CH CH1658665A patent/CH436259A/de unknown
- 1960-03-10 CH CH270760A patent/CH422758A/de unknown
- 1960-03-11 FR FR821114A patent/FR1421206A/fr not_active Expired
- 1960-03-11 NL NL249341A patent/NL129619C/xx active
- 1960-03-11 LU LU38374D patent/LU38374A1/xx unknown
- 1960-03-12 DK DK97360A patent/DK104353C/da active
- 1960-03-14 DE DE1960W0027453 patent/DE1238485C2/de not_active Expired
-
1969
- 1969-06-27 NL NL6909922A patent/NL6909922A/xx unknown
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49101519A (enrdf_load_stackoverflow) * | 1973-01-18 | 1974-09-25 | ||
| US3956369A (en) * | 1973-05-18 | 1976-05-11 | Ozeretskovskaya Natalia Nikola | N-β-(2-acetyl-4-chlorophenoxy)-ethyl-N,N-dimethyl-N-benzyl-ammonium-p-chlorobenzene sulphonate, method for preparing same and medicinal preparation based thereon |
| EP0103252A3 (de) * | 1982-09-11 | 1984-10-03 | BASF Aktiengesellschaft | Aryloxyalkylamine, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
| WO1995011238A1 (en) * | 1993-10-22 | 1995-04-27 | Smithkline Beecham Plc | Heterocyclic amines for treating ischaemic strokes |
| WO1995011240A1 (en) * | 1993-10-22 | 1995-04-27 | Smithkline Beecham Plc | Amine derivatives as calcium channel antagonists |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| EP0978512A1 (en) * | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
| EP2000462A3 (en) * | 1998-07-29 | 2011-05-04 | Bioprojet | Non-imidazole alkylamines as histamine H3-receptor ligands and their therapeutic applications |
| US7256312B2 (en) | 2002-08-01 | 2007-08-14 | Basf Aktiengesellschaft | Method for producing aminoalkoxy benzylamines and aminoalkoxy benzonitriles as intermediates |
| WO2012040133A3 (en) * | 2010-09-21 | 2012-05-10 | Ge Healthcare Limited | Novel precursors of radiolabelled choline analog compounds |
| JP2013537239A (ja) * | 2010-09-21 | 2013-09-30 | ジーイー・ヘルスケア・リミテッド | 新規前駆体 |
| JP2023517604A (ja) * | 2020-03-11 | 2023-04-26 | ノシオン セラピューティクス，インコーポレイテッド | 荷電したイオンチャンネル遮断薬および使用方法 |
| EP4118070A4 (en) * | 2020-03-11 | 2024-04-10 | Nocion Therapeutics, Inc. | CHARGED ION CHANNEL BLOCKERS AND METHODS OF USE |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
Also Published As
| Publication number | Publication date |
|---|---|
| DK104353C (da) | 1966-05-09 |
| ES256264A1 (es) | 1960-08-16 |
| LU38374A1 (enrdf_load_stackoverflow) | 1960-09-12 |
| DE1238485C2 (de) | 1967-10-26 |
| NL6909922A (enrdf_load_stackoverflow) | 1969-10-27 |
| FR558M (enrdf_load_stackoverflow) | 1961-05-29 |
| CH436259A (de) | 1967-05-31 |
| CH422758A (de) | 1966-10-31 |
| GR29331B (el) | 1965-12-29 |
| FR1421206A (fr) | 1965-12-17 |
| BE588558A (enrdf_load_stackoverflow) | 1960-09-12 |
| NL129619C (enrdf_load_stackoverflow) | 1970-08-18 |
| DE1238485B (de) | 1967-04-13 |
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