DE1292652B - Basisch substituierte Ester trisubstituierter Acrylsaeuren, deren Hydrochloride und Verfahren zu deren Herstellung - Google Patents
Basisch substituierte Ester trisubstituierter Acrylsaeuren, deren Hydrochloride und Verfahren zu deren HerstellungInfo
- Publication number
- DE1292652B DE1292652B DEG46252A DEG0046252A DE1292652B DE 1292652 B DE1292652 B DE 1292652B DE G46252 A DEG46252 A DE G46252A DE G0046252 A DEG0046252 A DE G0046252A DE 1292652 B DE1292652 B DE 1292652B
- Authority
- DE
- Germany
- Prior art keywords
- trisubstituted
- hydrochlorides
- acrylic acids
- general formula
- substituted esters
- 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
- 150000002148 esters Chemical class 0.000 title claims description 11
- 150000001253 acrylic acids Chemical class 0.000 title claims description 9
- 150000003840 hydrochlorides Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- XIGSUQSCEUGZTB-UHFFFAOYSA-N 2-benzhydrylidenebutanoic acid Chemical compound C=1C=CC=CC=1C(=C(C(O)=O)CC)C1=CC=CC=C1 XIGSUQSCEUGZTB-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ATZUFVYCSMUCIF-UHFFFAOYSA-N 2-benzhydrylidenehexanoic acid Chemical compound C=1C=CC=CC=1C(=C(C(O)=O)CCCC)C1=CC=CC=C1 ATZUFVYCSMUCIF-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- -1 amino propyl Chemical group 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000001989 choleretic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DJGAAPFSPWAYTJ-UHFFFAOYSA-M metamizole sodium Chemical compound [Na+].O=C1C(N(CS([O-])(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 DJGAAPFSPWAYTJ-UHFFFAOYSA-M 0.000 description 1
- 210000005037 parasympathetic nerve Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
- C07D295/10—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 doubly bound oxygen or sulphur atoms
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG46252A DE1292652B (de) | 1966-03-08 | 1966-03-08 | Basisch substituierte Ester trisubstituierter Acrylsaeuren, deren Hydrochloride und Verfahren zu deren Herstellung |
| AT177867A AT271454B (de) | 1966-03-08 | 1967-02-23 | Verfahren zur Herstellung von neuen basischen Estern α,β-disubstituierter Zimtsäuren und ihren Salzen |
| ES337592A ES337592A1 (es) | 1966-03-08 | 1967-03-04 | Procedimiento de obtencion de esteres basicamente sustitui-dos a partir de acidos acrilicos trisustituidos, de efecto antiflogistico. |
| BE695052D BE695052A (oth) | 1966-03-08 | 1967-03-06 | |
| NL6703540A NL6703540A (oth) | 1966-03-08 | 1967-03-06 | |
| FR69048367A FR1536213A (fr) | 1966-03-08 | 1967-03-07 | Procédé de préparation d'esters substitués basiques d'acides acryliques trisubstitués |
| CH329167A CH478090A (de) | 1966-03-08 | 1967-03-07 | Verfahren zur Herstellung von Estern trisubstituierter Acrylsäure |
| GB1075667A GB1139994A (en) | 1966-03-08 | 1967-03-07 | Novel acrylic acid derivatives and process for the preparation thereof |
| DK116867A DK114548B (da) | 1966-03-08 | 1967-03-07 | Fremgangsmåde til fremstilling af antiflogistisk virkende salte af basisk substituerede estre af trisubstituerede akrylsyrer. |
| SE317367A SE315881B (oth) | 1966-03-08 | 1967-03-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG46252A DE1292652B (de) | 1966-03-08 | 1966-03-08 | Basisch substituierte Ester trisubstituierter Acrylsaeuren, deren Hydrochloride und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1292652B true DE1292652B (de) | 1969-04-17 |
Family
ID=7127975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG46252A Pending DE1292652B (de) | 1966-03-08 | 1966-03-08 | Basisch substituierte Ester trisubstituierter Acrylsaeuren, deren Hydrochloride und Verfahren zu deren Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT271454B (oth) |
| BE (1) | BE695052A (oth) |
| CH (1) | CH478090A (oth) |
| DE (1) | DE1292652B (oth) |
| DK (1) | DK114548B (oth) |
| ES (1) | ES337592A1 (oth) |
| FR (1) | FR1536213A (oth) |
| GB (1) | GB1139994A (oth) |
| NL (1) | NL6703540A (oth) |
| SE (1) | SE315881B (oth) |
-
1966
- 1966-03-08 DE DEG46252A patent/DE1292652B/de active Pending
-
1967
- 1967-02-23 AT AT177867A patent/AT271454B/de active
- 1967-03-04 ES ES337592A patent/ES337592A1/es not_active Expired
- 1967-03-06 BE BE695052D patent/BE695052A/xx unknown
- 1967-03-06 NL NL6703540A patent/NL6703540A/xx unknown
- 1967-03-07 FR FR69048367A patent/FR1536213A/fr not_active Expired
- 1967-03-07 DK DK116867A patent/DK114548B/da unknown
- 1967-03-07 CH CH329167A patent/CH478090A/de not_active IP Right Cessation
- 1967-03-07 GB GB1075667A patent/GB1139994A/en not_active Expired
- 1967-03-08 SE SE317367A patent/SE315881B/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DK114548B (da) | 1969-07-14 |
| CH478090A (de) | 1969-09-15 |
| BE695052A (oth) | 1967-08-14 |
| AT271454B (de) | 1969-06-10 |
| NL6703540A (oth) | 1967-09-11 |
| SE315881B (oth) | 1969-10-13 |
| FR1536213A (fr) | 1968-08-16 |
| ES337592A1 (es) | 1968-03-01 |
| GB1139994A (en) | 1969-01-15 |
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