DE2309986A1 - N-benzoyl-4-dialkylaminoethoxyanilines - antispasmodics etc - Google Patents
N-benzoyl-4-dialkylaminoethoxyanilines - antispasmodics etcInfo
- Publication number
- DE2309986A1 DE2309986A1 DE19732309986 DE2309986A DE2309986A1 DE 2309986 A1 DE2309986 A1 DE 2309986A1 DE 19732309986 DE19732309986 DE 19732309986 DE 2309986 A DE2309986 A DE 2309986A DE 2309986 A1 DE2309986 A1 DE 2309986A1
- Authority
- DE
- Germany
- Prior art keywords
- benzoyl
- phenylamine
- bromide
- aminophenol
- diethylaminoethoxy
- 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
- 230000002921 anti-spasmodic effect Effects 0.000 title 1
- 229940124575 antispasmodic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 3
- -1 o-Hydroxybenzoyl Chemical group 0.000 claims description 43
- 238000002360 preparation method Methods 0.000 claims description 11
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003839 salts Chemical group 0.000 claims description 5
- ATAGHPWHVMMAOD-UHFFFAOYSA-N 2-ethoxy-n-(4-hydroxyphenyl)benzamide Chemical compound CCOC1=CC=CC=C1C(=O)NC1=CC=C(O)C=C1 ATAGHPWHVMMAOD-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 4
- LFJGGGIWERIGNX-UHFFFAOYSA-N 4-[2-(diethylamino)ethoxy]aniline Chemical compound CCN(CC)CCOC1=CC=C(N)C=C1 LFJGGGIWERIGNX-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- GBAMQUDAURZVCJ-UHFFFAOYSA-N 2-butoxy-N-(4-hydroxyphenyl)benzamide Chemical compound C(CCC)OC1=C(C(=O)NC2=CC=C(C=C2)O)C=CC=C1 GBAMQUDAURZVCJ-UHFFFAOYSA-N 0.000 claims description 2
- BTNKYPPSIYGIJR-UHFFFAOYSA-N 2-heptoxy-N-(4-hydroxyphenyl)benzamide Chemical compound C(CCCCCC)OC1=C(C(=O)NC2=CC=C(C=C2)O)C=CC=C1 BTNKYPPSIYGIJR-UHFFFAOYSA-N 0.000 claims description 2
- CCCVQPGAXZNTIL-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]aniline Chemical compound CN(C)CCOC1=CC=C(N)C=C1 CCCVQPGAXZNTIL-UHFFFAOYSA-N 0.000 claims description 2
- RLFJRJKVZOGWST-UHFFFAOYSA-N N-(4-hydroxyphenyl)-2-(3-phenylpropoxy)benzamide Chemical compound C1(=CC=CC=C1)CCCOC1=C(C(=O)NC2=CC=C(C=C2)O)C=CC=C1 RLFJRJKVZOGWST-UHFFFAOYSA-N 0.000 claims description 2
- RJCAZYQKJIXTPR-UHFFFAOYSA-N N-(4-hydroxyphenyl)-2-octoxybenzamide Chemical compound C(CCCCCCC)OC1=C(C(=O)NC2=CC=C(C=C2)O)C=CC=C1 RJCAZYQKJIXTPR-UHFFFAOYSA-N 0.000 claims description 2
- HBPUEAVDVSSVOZ-UHFFFAOYSA-N N-(4-hydroxyphenyl)-2-propoxybenzamide Chemical compound C(CC)OC1=C(C(=O)NC2=CC=C(C=C2)O)C=CC=C1 HBPUEAVDVSSVOZ-UHFFFAOYSA-N 0.000 claims description 2
- VTONMLBFZQJTOG-UHFFFAOYSA-N N-[4-[2-(diethylamino)ethoxy]phenyl]-2-heptoxybenzamide Chemical compound C(CCCCCC)OC1=C(C(=O)NC2=CC=C(C=C2)OCCN(CC)CC)C=CC=C1 VTONMLBFZQJTOG-UHFFFAOYSA-N 0.000 claims description 2
- KBPWECBBZZNAIE-UHFFFAOYSA-N aniline;hydron;bromide Chemical compound Br.NC1=CC=CC=C1 KBPWECBBZZNAIE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 229940102396 methyl bromide Drugs 0.000 claims description 2
- LXNXWBLKTWRVII-UHFFFAOYSA-N n-(4-hydroxyphenyl)-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=C(O)C=C1 LXNXWBLKTWRVII-UHFFFAOYSA-N 0.000 claims description 2
- JGZQMEPFCLXYBU-UHFFFAOYSA-N n-(4-hydroxyphenyl)-2-phenylmethoxybenzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 JGZQMEPFCLXYBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000006608 n-octyloxy group Chemical group 0.000 claims description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 125000006606 n-butoxy group Chemical group 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
- MDKAAWDKKBFSTK-UHFFFAOYSA-N 2-ethoxybenzoyl chloride Chemical compound CCOC1=CC=CC=C1C(Cl)=O MDKAAWDKKBFSTK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- JBESZWSJUKQSDM-UHFFFAOYSA-N (5-amino-2-hydroxyphenyl)-phenylmethanone Chemical class NC1=CC=C(O)C(C(=O)C=2C=CC=CC=2)=C1 JBESZWSJUKQSDM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
N-(o-Hydroxybenzoyl)-p-(2-dialkylaminoäthoxy)-phenylamine sowie o-substituierte Derivate und quartäre Salze derselben Die Erfindung betrifft N-(o-Hydroxybenzoyl)-p-(2-dialkylaminoäthoxy) -phenylamine sowie o-substituierte Derivate derselben der allgemeinen Formel in der R ein Wasserstoffatom oder eine Alkylgruppe mit 1 bis 8 Kohlenstoffatomen oder eine Arylalkylgruppe wie Benzyl, Phenyläthyl und Phenylpropyl und R1 eine Alkylgruppe mit 1 oder 2 gohlenstoffatomen bedeuten.N- (o-Hydroxybenzoyl) -p- (2-dialkylaminoethoxy) -phenylamines and o-substituted derivatives and quaternary salts thereof. The invention relates to N- (o-hydroxybenzoyl) -p- (2-dialkylaminoethoxy) -phenylamines and o-substituted ones Derivatives thereof of the general formula in which R is a hydrogen atom or an alkyl group with 1 to 8 carbon atoms or an arylalkyl group such as benzyl, phenylethyl and phenylpropyl and R1 is an alkyl group with 1 or 2 carbon atoms.
Die Erfindung betrifft weiterhin quartäre Salze der genannten Phenylamine bzw. der betreffenden genannten Derivate der allgemeinen Formel in der R und R1 wie oben definiert sind und X ein Anion wie Bromid, Chlorid, Jodid oder Sulfat ist.The invention further relates to quaternary salts of the phenylamines mentioned or the respective derivatives mentioned of the general formula in which R and R1 are as defined above and X is an anion such as bromide, chloride, iodide or sulfate.
Die Erfindung betrifft weiterhin N-/ o-Alkyloxy (oder -Arylalkyloxy)]-benzoyl-p-aminophenole. Diese Verbindungen sind Zwischenprodukte zur Herstellung der Verbindungen der allgemeinen Formel (I) und weisen die folgende allgemeine Pormel auf; in der R2 eine Alkylgruppe mit 1 bis 8 Kohlenstoffatomen oder eine Arylalkylgruppe wie Benzyl, Phenyläthyl und Phenylpropyl bedeutet.The invention further relates to N- / o-alkyloxy (or arylalkyloxy)] benzoyl-p-aminophenols. These compounds are intermediates for the preparation of the compounds of the general formula (I) and have the following general formula; in which R2 is an alkyl group with 1 to 8 carbon atoms or an arylalkyl group such as benzyl, phenylethyl and phenylpropyl.
Die Erfindung betrifft weiterhin pharmazeutisch bzw. The invention further relates to pharmaceutical or
therapeutisch verträgliche Additionssalze der Phenylamine der allgemeinen Formel (I) mit anorganischen oder organischen Säuren.therapeutically acceptable addition salts of the general phenylamines Formula (I) with inorganic or organic acids.
Im folgenden wird eine Aufstellung über hergestellte Phenylamine der allgemeinen Formel (I) der Erfindung gegeben. The following is a list of manufactured phenylamines given the general formula (I) of the invention.
1) N-(o-Hydroxybenzoyl)-p-( 2-diäthylaminoäthoxy)-phenylamin (R = H; R1 = C2H5) (Smp. 108 - 110°C).1) N- (o-Hydroxybenzoyl) -p- (2-diethylaminoethoxy) -phenylamine (R = H; R1 = C2H5) (m.p. 108-110 ° C).
2) N-(o-Kethoxybenzoyl)-p-(2-diäthylaminoäthoxy)-phenylPman (R = CH3; R1 = C2H5) (Hydrochlorid, Smp. 132 - 133°C).2) N- (o-Kethoxybenzoyl) -p- (2-diethylaminoethoxy) -phenylPman (R = CH3; R1 = C2H5) (hydrochloride, m.p. 132-133 ° C).
3) N-(o-Äthoxybenzoyl)-p-(2-dimethylaminoäthoxy)-phenylamin (R = C2H5; R1 = CH3) (Smp. 72 - 74°C).3) N- (o-ethoxybenzoyl) -p- (2-dimethylaminoethoxy) -phenylamine (R = C2H5; R1 = CH3) (m.p. 72-74 ° C).
4) B-(o-Äthoxybensoyl)-p-(2-diäthylaminoäth ( = C2R5; R1 - C2H5) (Smp. 48 - 49°C).4) B- (o-ethoxy likewiseyl) -p- (2-diethylaminoeth (= C2R5; R1 - C2H5) (m.p. 48 - 49 ° C).
5) N-g o-(n-Propoxy)-benzoyl 7-p- (2-diäthylaminoäthoxy)-phenylamin (R = nC3H7; R1 = C2H5) (Smp. 63 - 65°C).5) N-g o- (n-propoxy) benzoyl 7-p- (2-diethylaminoethoxy) phenylamine (R = nC3H7; R1 = C2H5) (m.p. 63-65 ° C).
6) N-Co-(n-Butoxy )-benzoyl~7-p-( 2-diäthylaminoäthoxy)-phenylamin (R = nC4Hs; R1 = C2H5) (Smp. 74 - 75°C). 6) N-Co- (n-butoxy) -benzoyl ~ 7-p- (2-diethylaminoethoxy) -phenylamine (R = nC4Hs; R1 = C2H5) (m.p. 74-75 ° C).
7) N-/-o-(n-Amyloxy)-benzoyl 7-p-(2-diäthylaminoäthoxy)-phenylamin (R = nC5H11; R1 = C2H5) (Smp. 54 - 56°C). 7) N - / - o- (n-Amyloxy) benzoyl 7-p- (2-diethylaminoethoxy) phenylamine (R = nC5H11; R1 = C2H5) (m.p. 54-56 ° C).
8) N-[o-(n-Heptyloxy)-benzoyl]-p-(2-diäthylaminoäthoxy)-phenylamin (R = nC7H15; R1 = C2H5) (Smp. 44 - 46°C). 8) N- [o- (n-heptyloxy) benzoyl] -p- (2-diethylaminoethoxy) phenylamine (R = nC7H15; R1 = C2H5) (m.p. 44-46 ° C).
9) N- [o-(n-Octyloxy)-benzoyl]-p-(2-diäthylaminoäthoxy)-phenylamin (R = nC8H17; R1 = C2H5) (Smp. 56 - 58°C). 9) N- [o- (n-Octyloxy) -benzoyl] -p- (2-diethylaminoethoxy) -phenylamine (R = nC8H17; R1 = C2H5) (m.p. 56-58 ° C).
10) N-(o-Benzyloxy-benzoyl)-p-(2-diäthylaminoäthoxy)-phenylamin (R = CH2C6H5; R1 = C2H5) (Smp. 66 - 6800).10) N- (o-Benzyloxy-benzoyl) -p- (2-diethylaminoethoxy) -phenylamine (R = CH2C6H5; R1 = C2H5) (m.p. 66-6800).
11) N-Jo-(ß-Phenyläthoxy)-benzoyl~7-p-(2-diäthylaminoäthoxy)-phenylamin (R = CH2CH2C6H5; R1 = C2H5) (Smp. 98 - 10000).11) N-Jo- (ß-phenylethoxy) -benzoyl ~ 7-p- (2-diethylaminoethoxy) -phenylamine (R = CH2CH2C6H5; R1 = C2H5) (m.p. 98-10,000).
12) N- o-(g-Phenyl-n-propoxy)-benzoyl 7-p-(2-diäthylaminoäthoxy)-phenylamin (R = CH2CH2CH2C6H5; R1 = C2H5) (Smp. 58 - 60°C).12) N- o- (g-Phenyl-n-propoxy) -benzoyl 7-p- (2-diethylaminoethoxy) -phenylamine (R = CH2CH2CH2C6H5; R1 = C2H5) (m.p. 58-60 ° C).
Quartäre Salze gemäß der allgemeinen Formel (II) können die folgenden sein: 13) N-(o-Hydroxybenzoyl)-p-(2-diäthyl-methyl-anunonio-äthoxy) phenylamin-bromid (R = H; R1 = C2H5; X = Br) (Smp. 198 - 200°C). Quaternary salts according to the general formula (II) can include the following be: 13) N- (o-Hydroxybenzoyl) -p- (2-diethyl-methyl-anunonio-ethoxy) phenylamine bromide (R = H; R1 = C2H5; X = Br) (m.p. 198-200 ° C).
14) N-(o-Methoxybenzoyl)-p-(2-diäthyl-methyl-nmmonio-äthoxy)-phenylamin-bromid (R = CH3; R1 = C2H5; X = Br) (Smp. 149 - 15100).14) N- (o-methoxybenzoyl) -p- (2-diethyl-methyl-nmmonio-ethoxy) -phenylamine-bromide (R = CH3; R1 = C2H5; X = Br) (m.p. 149-15100).
15) N-(o-Äthoxybenzoyl)-p-(2-triäthyl-ammonio-äthoxy) phenylamin-bromid (R = C2H5; R1 CH3; X = Br) (Smp. 217 - 219°C).15) N- (o-Ethoxybenzoyl) -p- (2-triethylammonioethoxy) phenylamine bromide (R = C2H5; R1 CH3; X = Br) (m.p. 217-219 ° C).
16) N-(o-Äthoxybenzoyl)-p-(2-diäthyl-methyl-ammonio-äthoxy)-phenylamin-bromid (R = C2H5; R1 = C2H5; X = Br) (Smp. 148 - 149°C).16) N- (o-Ethoxybenzoyl) -p- (2-diethyl-methyl-ammonio-ethoxy) -phenylamine-bromide (R = C2H5; R1 = C2H5; X = Br) (m.p. 148-149 ° C).
17) N-[o-(n-Propoxy)-benzoyl]-p-(2-diäthyl-methyl-ammonioäthoxy)-phenylamin-bromid (R = nC3H7; R1 = C2H5; X = Br) (Smp. 132 - 133°C).17) N- [o- (n-propoxy) -benzoyl] -p- (2-diethyl-methyl-ammonioethoxy) -phenylamine-bromide (R = nC3H7; R1 = C2H5; X = Br) (m.p. 132-133 ° C).
18) N-g o-(n-Butoxy)-benzoyl 7-p-(2-diäthyl-methyl-nmmonioäthoxy)-phenylamin-bromid (R = nC4Hg; R1 = C2H5; X = Br) (Smp. 121 - 123°C).18) N-g o- (n-butoxy) -benzoyl 7-p- (2-diethyl-methyl-nmmonioethoxy) -phenylamine-bromide (R = nC4Hg; R1 = C2H5; X = Br) (m.p. 121-123 ° C).
19) N-[o-(n-Amyloxy)-benzoyl]-p-(2-diäthyl-methyl-ammonioäthoxy)-phenylamin-bromid (R = nC5H11; R1 = C2H5; X = Br) (Smp. 146 - 147°C).19) N- [o- (n-amyloxy) -benzoyl] -p- (2-diethyl-methyl-ammonioethoxy) -phenylamine-bromide (R = nC5H11; R1 = C2H5; X = Br) (m.p. 146-147 ° C).
20) N-[o-(n-Heptyloxy)-benzoyl]-p-(2-diäthyl-methyl-ammonioäthoxy)-phenylamin-bromid (R = nC7H15; R1 = C2H5; X = Br) (Smp. 124 - 125°C).20) N- [o- (n-heptyloxy) -benzoyl] -p- (2-diethyl-methyl-ammonioethoxy) -phenylamine-bromide (R = nC7H15; R1 = C2H5; X = Br) (m.p. 124-125 ° C).
21) N-[o-(n-Octyloxy)-benzoyl]-p-(2-diäthyl-methylammonio-äthoxy)-phenylamin-bromid (R = nC8H17; R1 = C2H5; X = Br) (Smp. 133 - 135°C).21) N- [o- (n-Octyloxy) -benzoyl] -p- (2-diethyl-methylammonio-ethoxy) -phenylamine-bromide (R = nC8H17; R1 = C2H5; X = Br) (m.p. 133-135 ° C).
22) N-(o-Benzyloxy-benzoyl)-p-(2-diäthyl-methyl-ammonioätholcy)-phenylamin-bromid (R = CH2C6H5; R1 = X = Br) (Smp. 161 - 162°C).22) N- (o-Benzyloxy-benzoyl) -p- (2-diethyl-methyl-ammonioethyl) -phenylamine-bromide (R = CH2C6H5; R1 = X = Br) (m.p. 161-162 ° C).
23) N-[o-(ß-Phenyläthoxy)-benzoyl]-p-(2-diäthyl-methylammonio-äthoxy)-phenylamin-bromid (R = CH2CH2C6H5; R1 = C2H5; X = Br) (Smp. 147 - 1500C).23) N- [o- (β-phenylethoxy) -benzoyl] -p- (2-diethyl-methylammonio-ethoxy) -phenylamine-bromide (R = CH2CH2C6H5; R1 = C2H5; X = Br) (m.p. 147-1500C).
24) N-[o-(γ-Phenyl-n-propoxy)-benzoyl]-p-(2-diäthylmethyl-ammonio-äthoxy)-phenylamin-bromid (R = CH2CH2CH2C6H5; R1 = C2H5; X = Br) (Smp. 137 - 140°C).24) N- [o- (γ-phenyl-n-propoxy) -benzoyl] -p- (2-diethylmethyl-ammonio-ethoxy) -phenylamine-bromide (R = CH2CH2CH2C6H5; R1 = C2H5; X = Br) (m.p. 137-140 ° C).
Zwischenprodukte der allgemeinen Formel (III) zur Herstellung der Verbindungen der allgemeinen Formel (I) können die folgenden sein: 25) N-(o-Methoxybenzoyl)-p-aminophenol (R2 = CH3) (Smp. 169 - 170°C). Intermediates of the general formula (III) for the preparation of Compounds of the general formula (I) can be the following: 25) N- (o-methoxybenzoyl) -p-aminophenol (R2 = CH3) (m.p. 169-170 ° C).
26) N-(o-Äthoxybenzoyl)-p-aminophenol (R2 = C2H5) (Smp. 161 - 163°C).26) N- (o-Ethoxybenzoyl) -p-aminophenol (R2 = C2H5) (m.p. 161-163 ° C).
27) N-[o-(n-Propoxy)-benzoyl]-p-aminophenol (R2 = nC3H7) (Smp. 144 - 145°C).27) N- [o- (n-Propoxy) benzoyl] p-aminophenol (R2 = nC3H7) (m.p. 144 - 145 ° C).
28) N-[o-(n-Butoxy)-benzoyl]-p-aminophenol (R2 = nC4Hg) (Smp. 146 - 14800).28) N- [o- (n-Butoxy) -benzoyl] -p-aminophenol (R2 = nC4Hg) (m.p. 146 - 14800).
29) N-[o-(n-Amyloxy)-benzoyl]-p-aminophenol (R2 = nC5H11) (Smp. 129 - 1310C).29) N- [o- (n-Amyloxy) -benzoyl] -p-aminophenol (R2 = nC5H11) (m.p. 129 - 1310C).
30) N-[o-(n-Heptyloxy)-benzoyl]-p-aminophenol (R2 = nC7H15) (Smp. 98 - 10000).30) N- [o- (n-heptyloxy) -benzoyl] -p-aminophenol (R2 = nC7H15) (m.p. 98 - 10000).
31) N-[o-(n-Octyloxy)-benzoyl]-p-aminophenol (R2 = n08H17) (Smp. 104 - 10600).31) N- [o- (n-Octyloxy) -benzoyl] -p-aminophenol (R2 = n08H17) (m.p. 104 - 10600).
32) N-(o-Benzyloxy-benzoyl)-p-aminophenol (R2 = CH2C6H5) (Smp. 174 - 1760C).32) N- (o-Benzyloxy-benzoyl) -p-aminophenol (R2 = CH2C6H5) (m.p. 174 - 1760C).
33) N-[o-(ß-Phenyläthoxy)-benzoyl]-p-aminophenol (R2 = CH2CH2C6H5) (Smp. 156 - 158°C).33) N- [o- (ß-Phenylethoxy) -benzoyl] -p-aminophenol (R2 = CH2CH2C6H5) (M.p. 156-158 ° C).
34) N-[o-(γ-Phenyl-n-propoxy)-benzoyl]-p-aminophenol (R2 = CH2CH2CH2C6H5) (Smp. 124 - 126°C).34) N- [o- (γ-Phenyl-n-propoxy) -benzoyl] -p-aminophenol (R2 = CH2CH2CH2C6H5) (M.p. 124-126 ° C).
Die oben genannten Verbindungen zeigen eine bemerkenswerte pharmakologische Wirksamkeit und können zu verschiedenen therapeutischen Zwecken angewendet werden. The above compounds show a remarkable pharmacological Efficacy and can be used for various therapeutic purposes.
Die Verbindungen gemäß den allgemeinen Formeln (I) und (II) weisen insbesondere spasmolytische wirkungen und gefäßerweiternde Eigenschaften auf. In den Verbindungen, in denen R eine Alkylgruppe ist, ist die spasmolytische Aktivität (Vermögen zum Antagonisieren Bariumchlorid-induzierter Spasmen) proportional zu der Länge der Alkylkette. The compounds according to the general formulas (I) and (II) have in particular spasmolytic effects and vasodilating properties. In the compounds in which R is an alkyl group is spasmolytic activity (Ability to antagonize barium chloride-induced spasms) proportional to the length of the alkyl chain.
Die Verbindungen gemäß der allgemeinen Formel (III), die Zwischenprodukte zur Herstellung der Verbindungen der allgemeinen Formel (I) sind, weisen selbst eine analgetische, antiphlogistische und antipyretische Wirksamkeit auf. The compounds according to the general formula (III), the intermediates for the preparation of the compounds of general formula (I) are themselves an analgesic, anti-inflammatory and antipyretic activity.
Die Erfindung betrifft weiterhin Verfahren zur Herstellung der oben genannten Verbindungen. The invention further relates to methods of making the above named compounds.
Die Verbindungen der allgemeinen Formel (I) können erhalten werden, indem man geeignete Benzoylhalogenide oder geeignete Ester oder Anhydride mit p-(2-Diäthylaminoäthoxy )-phenylamin oder mit p- ( 2-Dimethylaminoäthoxy ) -phenylamin kondensiert oder die geeignet substituierten p-Aminophenole der allgemeinen Formel (III) mit 2-Diäthylaminoäthylhalogeniden oder 2-Dimethylaminoäthylhalogeniden in einem alkalischen Medium veräthert oder indem man ein geeignetes N-Jo-Alkyloxy (oder -Arylalkyloxy)-benzoyl 7-p- ( 2-halogenäthoxy)-phenylamin mit Diäthylamin oder Dimethylamin kondensiert. The compounds of the general formula (I) can be obtained by mixing suitable benzoyl halides or suitable esters or anhydrides with p- (2-diethylaminoethoxy ) -phenylamine or condensed with p- (2-dimethylaminoethoxy) -phenylamine or the suitably substituted p-aminophenols of the general formula (III) with 2-diethylaminoethyl halides or etherified or 2-dimethylaminoethyl halides in an alkaline medium by adding a suitable N-Jo-alkyloxy (or -arylalkyloxy) -benzoyl 7-p- (2-haloethoxy) -phenylamine condensed with diethylamine or dimethylamine.
Die Verbindungen der allgemeinen Formel (II) können erhalten werden, indem man die entsprechenden Verbindungen der allgemeinen Formel (1) in einem Quartärnierungverfahren unter Verwendung von Chlorid, Bromid, Jodid bzw. ethylchlorid, Methylbromid, Methyljodid oder Dimethylsulfat umsetzt. The compounds of the general formula (II) can be obtained by converting the corresponding compounds of general formula (1) in a quaternization process using chloride, bromide, iodide or ethyl chloride, methyl bromide, methyl iodide or dimethyl sulfate.
Die Verbindungen der allgemeinen Formel (III) können hergestellt werden, indem man p-Aminophenol mit geeigneten Benzoylhalogeniden, Estern oder Anhydriden umsetzt. The compounds of the general formula (III) can be prepared by mixing p-aminophenol with suitable benzoyl halides, esters or anhydrides implements.
Im folgenden wird über einige Verfahren zur Herstellung von N-(o-Äthoxybenzoyl)-p-(2-diäthylaminoäthoxy)-phenylRmin (Verbindung 4) und dessen Zwischenprodukt N-(o-Äthoxybenzoyl)-p-aminophenol (Verbindung 26) berichtet. The following describes some processes for the preparation of N- (o-ethoxybenzoyl) -p- (2-diethylaminoethoxy) -phenylRmin (Compound 4) and its intermediate N- (o-ethoxybenzoyl) -p-aminophenol (Compound 26) reported.
Beispiele 1a) und 1b) Herstellung von N- ( o-Äthoxybenzoyl )-p-( 2-diäthylaminoäthoxy)-phenylamin (Verbindung 4).Examples 1a) and 1b) Preparation of N- (o-ethoxybenzoyl) -p- (2-diethylaminoethoxy) phenylamine (Compound 4).
a) Zu 4 g Natriumhydroxid, gelöst in 100 ml Äthanol, werden 25,7 g N-(o-Äthoiybenzoyl)-p-aminophenol (26) gegeben. Die Mischung wird 1 Stunde am Rückfluß erhitzt. Nach dem Abkühlen werden 14,5 g N-Diäthylaminoäthylchlorid zugegeben. Die Mischung wird 6 Stunden lang am Rückfluß gekocht. Das Lösung mittel wird unter vermindertem Druck durch Destillation entfernt. Der RUckstand wird mit wasser aufgearbeitet. Der erhaltene Niederschlag wird filtriert und getrocknet, aus Hexan umkristallisiert und weist einen Schmelzpunkt von 4 - 49°C auf. a) To 4 g of sodium hydroxide dissolved in 100 ml of ethanol, 25.7 g N- (o-Äthoiybenzoyl) -p-aminophenol (26) added. The mixture is 1 hour on Heated to reflux. After cooling, 14.5 g of N-diethylaminoethyl chloride are added. The mixture is refluxed for 6 hours. The solution medium is below removed by distillation under reduced pressure. The arrears will worked up with water. The precipitate obtained is filtered and dried, recrystallized from hexane and has a melting point of 4-49 ° C.
b) Zu 20,8 g p-(2-Diäthylaminoäthoxy)-anilin in 200 ml wasserfreiem Benzol werden tropfenweise langsam und unter Rühren 18,4 g o-Äthoxybenzoylchlorid gegeben. Die Mischung wird 30 Minuten am Rückfluß gekocht. Nach dem Abkühlen wird der erhaltene Niederschlag filtriert, getrocknet und mit 5 einem Natriumhydroxid behandelt. Das erhaltene Produkt wird filtriert, getrocknet, aus Hexan umkristallisiert und weist einen Schmelzpunkt von 48 - 490C auf. b) To 20.8 g of p- (2-diethylaminoethoxy) aniline in 200 ml of anhydrous Benzene are slowly added dropwise and with stirring 18.4 g of o-ethoxybenzoyl chloride given. The mixture is refluxed for 30 minutes. After cooling it will the precipitate obtained is filtered, dried and treated with a sodium hydroxide treated. The product obtained is filtered, dried and recrystallized from hexane and has a melting point of 48 - 490C.
Beispiel 2 Herstellung von N-( o-Äthoxybenzoyl ) -p-aminophenol (Verbindung 26).Example 2 Preparation of N- (o-Ethoxybenzoyl) -p-aminophenol (compound 26).
18,4 g o-Äthoxybenzoylchlorid werden langsam unter Rühren in eine Lösung eingetropft, welche aus 500 ml wasserfreiem Dioxan, 7,9 g wasserfreiem Pyridin und 10,9 g p-Aminophenol besteht. 18.4 g of o-ethoxybenzoyl chloride are slowly stirred into a Dripped solution, which consists of 500 ml of anhydrous dioxane, 7.9 g of anhydrous pyridine and consists of 10.9 grams of p-aminophenol.
Nach Beendigung der Zugabe wird die Mischung 1,5 Stunden auf einem Wasserbad erhitzt. Nach dem Abkühlen wird die Reaktionamischung in verdünnte Salzsäure eingegossen. Der ausgeschiedene Niederschlag wird abfiltriert, mit Wasser gewaschen und mit 5 %igem Natriumhydroxid behandelt. Beim Ansäuern der erhaltenen filtrierten Lösung mit verdünnter Salzsäure scheidet sich ein Niederschlag ab, der aus Äthanol umkristallisiert einen Schmelzpunkt von 161 - 16300 aufweist. After the addition is complete, the mixture is left on for 1.5 hours Heated water bath. After cooling, the reaction mixture is dissolved in dilute hydrochloric acid poured. The deposited precipitate is filtered off and washed with water and treated with 5% sodium hydroxide. Upon acidification of the obtained filtered Solution with dilute hydrochloric acid separates a precipitate, which consists of ethanol recrystallized has a melting point of 161 - 16,300.
Claims (42)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309986 DE2309986A1 (en) | 1973-02-28 | 1973-02-28 | N-benzoyl-4-dialkylaminoethoxyanilines - antispasmodics etc |
| JP3312873A JPS49126643A (en) | 1973-02-28 | 1973-03-24 | |
| BE129408A BE797498A (en) | 1973-02-28 | 1973-03-29 | N- (O-HYDROXYBENZOYL) -P- (2-DIALCOYLAMINOETHOXY) - PHENYL-AMINE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309986 DE2309986A1 (en) | 1973-02-28 | 1973-02-28 | N-benzoyl-4-dialkylaminoethoxyanilines - antispasmodics etc |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2309986A1 true DE2309986A1 (en) | 1974-08-29 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732309986 Pending DE2309986A1 (en) | 1973-02-28 | 1973-02-28 | N-benzoyl-4-dialkylaminoethoxyanilines - antispasmodics etc |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS49126643A (en) |
| BE (1) | BE797498A (en) |
| DE (1) | DE2309986A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002100341A3 (en) * | 2001-06-12 | 2004-07-01 | Wellstat Therapeutics Corp | Compounds for the treatment of metabolic disorders |
-
1973
- 1973-02-28 DE DE19732309986 patent/DE2309986A1/en active Pending
- 1973-03-24 JP JP3312873A patent/JPS49126643A/ja active Pending
- 1973-03-29 BE BE129408A patent/BE797498A/en unknown
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002100341A3 (en) * | 2001-06-12 | 2004-07-01 | Wellstat Therapeutics Corp | Compounds for the treatment of metabolic disorders |
| US6858602B2 (en) | 2001-06-12 | 2005-02-22 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US6916848B2 (en) | 2001-06-12 | 2005-07-12 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US6924314B2 (en) | 2001-06-12 | 2005-08-02 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US6946491B2 (en) | 2001-06-12 | 2005-09-20 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7012071B2 (en) | 2001-06-12 | 2006-03-14 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7041659B2 (en) | 2001-06-12 | 2006-05-09 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7045541B2 (en) | 2001-06-12 | 2006-05-16 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7101910B2 (en) | 2001-06-12 | 2006-09-05 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| CN100344616C (en) * | 2001-06-12 | 2007-10-24 | 维尔斯达医疗公司 | Compounds for the treatment of metabolic disorders |
| US7329782B2 (en) | 2001-06-12 | 2008-02-12 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7547802B2 (en) | 2001-06-12 | 2009-06-16 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7863475B2 (en) | 2001-06-12 | 2011-01-04 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US8487000B2 (en) | 2001-06-12 | 2013-07-16 | Wellstat Therapertics Corporation | Compound for the treatment of metabolic disorders |
| US8552062B2 (en) | 2001-06-12 | 2013-10-08 | Wellstat Therapeutics Corporation | Methods for the treatment of metabolic disorders such as diabetes |
| US8604083B2 (en) | 2001-06-12 | 2013-12-10 | Wellstat Therapeutics Corporation | Method for the treatment of metabolic disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49126643A (en) | 1974-12-04 |
| BE797498A (en) | 1973-07-16 |
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