GB1032872A - Aryloxy acetic acid amides and processes for their production - Google Patents
Aryloxy acetic acid amides and processes for their productionInfo
- Publication number
- GB1032872A GB1032872A GB844/65A GB84465A GB1032872A GB 1032872 A GB1032872 A GB 1032872A GB 844/65 A GB844/65 A GB 844/65A GB 84465 A GB84465 A GB 84465A GB 1032872 A GB1032872 A GB 1032872A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- acid
- cinnamic
- compound
- prepared
- 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
- 238000000034 method Methods 0.000 title abstract 3
- -1 Aryloxy acetic acid amides Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229940124326 anaesthetic agent Drugs 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 229940106681 chloroacetic acid Drugs 0.000 abstract 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 abstract 1
- NGSWKAQJJWESNS-UHFFFAOYSA-N cis-para-coumaric acid Natural products OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 238000005809 transesterification reaction Methods 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Abstract
Novel compounds of formula <FORM:1032872/C2/1> where X represents -CH2CH2- or -CH = CH-, and R1, R2, R3 and R4 represent alkyl groups having 1-5 carbon atoms, or R3 and R4 together with the nitrogen, optionally with an oxygen atom as ring member, represent a saturated heterocyclic radical having 5-7 ring members, are prepared (1) by reacting a compound of Formula II <FORM:1032872/C2/2> or a salt thereof with a reactive ester of a hydroxyl compound of formula HO-CH2-CO-NR3R4 in the presence of an acid binding agent, (2) by esterifying an acid of Formula I in which R1 is hydrogen or a reactive functional derivative thereof, (3) by reacting an aryloxy-acetic acid of Formula II in which -OH is replaced by -OCH2COOH, or a reactive functional derivative of such an acid with a compound of formula HNR3R4, (4) by heating an aryloxy-acetic acid as defined in (3) with a carbamoyl chloride of formula Cl-CO-NR3R4, (5) by transesterification of a compound of Formula I in which the alkyl group R1 has fewer carbon atoms than the desired group R1, and (6) for compounds of Formula I in which X represents -CH2CH2-, by reducing the corresponding compound in which X represents -CH = CH-. Therapeutic compositions useful as short-acting anaesthetics and which can be applied intravenously contain as active ingredient compounds of Formula I above. The 4-carbamoylmethoxy-cinnamic and -hydrocinnamic acid starting materials of process (2) may be prepared by reacting a 3-alkoxy-4-hydroxybenzaldehyde in the presence of ethanolic sodium hydroxide with a suitable chloroacetic acid amide, condensing the compounds obtained with malonic acid in pyridine and piperidine, the condensation products then being partially decarboxylated and optionally catalytically hydrogenated. The 3-alkoxy-4-(carboxymethoxy)-cinnamic and -hydrocinnamic acid ester starting materials of processes (3) and (4) may be prepared by etherifying 3-alkoxy-4-hydroxy-cinnamic and hydrocinnamic acid alkyl esters with chloroacetic acid in the presence of ethanolic sodium hydroxide. 3-Methoxy-4-hydroxy-cinnamic and-hydrocinnamic acid esters may be produced by esterification; the hydrocinnamic acid esters may also be prepared by catalytic hydrogenation of the corresponding cinnamic acid esters.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH27864A CH432494A (en) | 1964-01-10 | 1964-01-10 | Process for the preparation of new aryloxyacetic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1032872A true GB1032872A (en) | 1966-06-15 |
Family
ID=4183337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB844/65A Expired GB1032872A (en) | 1964-01-10 | 1965-01-08 | Aryloxy acetic acid amides and processes for their production |
Country Status (7)
| Country | Link |
|---|---|
| AT (3) | AT251568B (en) |
| BE (1) | BE658086A (en) |
| CH (1) | CH432494A (en) |
| ES (3) | ES307982A1 (en) |
| FR (2) | FR1441465A (en) |
| GB (1) | GB1032872A (en) |
| NL (1) | NL6500209A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6887866B2 (en) | 2002-01-25 | 2005-05-03 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| WO2007111276A1 (en) * | 2006-03-24 | 2007-10-04 | Ajinomoto Co., Inc. | Novel ester derivative and use thereof |
| US7790766B2 (en) | 2003-07-23 | 2010-09-07 | Theravance, Inc. | Pharmaceutical compositions of short-acting sedative hypnotic agent |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5274002A (en) * | 1987-04-14 | 1993-12-28 | Warner-Lambert Company | Trisubstituted phenyl analogs having activity for congestive heart failure |
-
1964
- 1964-01-10 CH CH27864A patent/CH432494A/en unknown
-
1965
- 1965-01-08 AT AT134266A patent/AT251568B/en active
- 1965-01-08 AT AT134366A patent/AT251569B/en active
- 1965-01-08 BE BE658086D patent/BE658086A/xx unknown
- 1965-01-08 GB GB844/65A patent/GB1032872A/en not_active Expired
- 1965-01-08 AT AT12265A patent/AT251567B/en active
- 1965-01-08 NL NL6500209A patent/NL6500209A/xx unknown
- 1965-01-09 ES ES0307982A patent/ES307982A1/en not_active Expired
- 1965-01-09 ES ES0307983A patent/ES307983A1/en not_active Expired
- 1965-01-09 FR FR1389A patent/FR1441465A/en not_active Expired
- 1965-01-09 ES ES0307984A patent/ES307984A1/en not_active Expired
- 1965-04-08 FR FR12399A patent/FR4307M/fr not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6887866B2 (en) | 2002-01-25 | 2005-05-03 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| US7015346B2 (en) | 2002-01-25 | 2006-03-21 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| US7514425B2 (en) | 2002-01-25 | 2009-04-07 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| US7939689B2 (en) | 2002-01-25 | 2011-05-10 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| US7790766B2 (en) | 2003-07-23 | 2010-09-07 | Theravance, Inc. | Pharmaceutical compositions of short-acting sedative hypnotic agent |
| US7981931B2 (en) | 2003-07-23 | 2011-07-19 | Theravance, Inc. | Pharmaceutical compositions of short-acting sedative hypnotic agent |
| WO2007111276A1 (en) * | 2006-03-24 | 2007-10-04 | Ajinomoto Co., Inc. | Novel ester derivative and use thereof |
| US8212068B2 (en) | 2006-03-24 | 2012-07-03 | Ajinomoto Co., Inc. | Ester derivative and use thereof |
| US8765809B2 (en) | 2006-03-24 | 2014-07-01 | Ajinomoto Co., Inc. | Ester derivative and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR4307M (en) | 1966-07-25 |
| AT251569B (en) | 1967-01-10 |
| FR1441465A (en) | 1966-06-10 |
| CH432494A (en) | 1967-03-31 |
| AT251568B (en) | 1967-01-10 |
| NL6500209A (en) | 1965-07-12 |
| AT251567B (en) | 1967-01-10 |
| ES307983A1 (en) | 1965-12-16 |
| ES307984A1 (en) | 1965-06-16 |
| ES307982A1 (en) | 1965-06-16 |
| BE658086A (en) | 1965-07-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1032872A (en) | Aryloxy acetic acid amides and processes for their production | |
| GB2008111A (en) | A process for the production of gamma -Chlorocarboxylic Acid Esters | |
| ES8304917A1 (en) | Quaternary N-alkyl-N,N'-polyoxyalkyl-alpha, omega-diaminoalkylene fatty-acid esters, process for their production and their use. | |
| ES421098A1 (en) | Fluoro-substituted thiaxanthene derivatives | |
| ES384946A1 (en) | Novel adamantylurea derivatives and a process for the preparation thereof | |
| GB1031090A (en) | New aryloxyacetic amides, their production and compositions containing same | |
| GB836332A (en) | Novel amino-acid hydrazides and a process for the manufacture of same | |
| GB847779A (en) | 2-(4-biphenylyl)-í¸-hexenoic acid esters thereof | |
| GB893920A (en) | Polycyclic amino compounds and methods for their production | |
| ES321802A1 (en) | Substituted 1,2,3,6-tetrahydro-4-pyridine acetic acid amides | |
| GB800565A (en) | Method of producing n-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides | |
| GB998355A (en) | Phenylalanine derivatives | |
| JPS55141457A (en) | Novel benzylidene derivative | |
| GB820503A (en) | Improvements in or relating to the production of n-substituted 2-hydroxymethyl pyrrolidines | |
| AT216500B (en) | Process for the production of new, basic substituted β - phenylhydracrylic acid or. O-acyl-β-phenyl-hydracrylic acid esters and their salts | |
| GB883733A (en) | Process for the preparation of fatty acid bis (hydroxy-alkyl) amides | |
| GB923895A (en) | New carboxylic acid amides and process for their manufacture | |
| GB833908A (en) | Novel acid hydrazides and a process for the manufacture of same | |
| GB771151A (en) | Method for the preparation of aminoacyl-anilides | |
| GB878068A (en) | Improvements in or relating to the preparation of basic benzilic acid ester derivatives | |
| JPS54125687A (en) | Pirazine derivative and its preparation | |
| ES428254A1 (en) | Procedure for the obtaining of 2-acetoxibenzoatos of n (2-hydroxythyl) amidas of fatty acids. (Machine-translation by Google Translate, not legally binding) | |
| GB840361A (en) | New morpholinoacyl anilides and methods for their preparation | |
| JPS55100383A (en) | Preparation of novel nitrogen-containing polycyclic compound | |
| GB837266A (en) | Aromatic amides of trialkoxybenzoic acids |