GB1380095A - Carboxamidobenzoic acids as hypolipemic agents - Google Patents
Carboxamidobenzoic acids as hypolipemic agentsInfo
- Publication number
- GB1380095A GB1380095A GB4999972A GB4999972A GB1380095A GB 1380095 A GB1380095 A GB 1380095A GB 4999972 A GB4999972 A GB 4999972A GB 4999972 A GB4999972 A GB 4999972A GB 1380095 A GB1380095 A GB 1380095A
- Authority
- GB
- United Kingdom
- Prior art keywords
- preparation
- carbomethoxy
- treating
- acid
- compounds
- 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
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title abstract 2
- 239000003524 antilipemic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 abstract 2
- WXVJDWMXAVMQPO-UHFFFAOYSA-N 4-chloro-3-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC(C(O)=O)=CC=C1Cl WXVJDWMXAVMQPO-UHFFFAOYSA-N 0.000 abstract 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- RKTRHMNWVZRZJQ-UHFFFAOYSA-N (4-fluorophenyl)methanethiol Chemical compound FC1=CC=C(CS)C=C1 RKTRHMNWVZRZJQ-UHFFFAOYSA-N 0.000 abstract 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 abstract 1
- SRXFXCKTIGELTI-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C=C1 SRXFXCKTIGELTI-UHFFFAOYSA-N 0.000 abstract 1
- ZVNIXAXNTKOCQU-UHFFFAOYSA-N 3-methoxycarbonyl-4-methylbenzenecarbothioic S-acid Chemical compound C(=O)(OC)C=1C=C(C(=S)O)C=CC1C ZVNIXAXNTKOCQU-UHFFFAOYSA-N 0.000 abstract 1
- MQVAHEBEWAKTBK-UHFFFAOYSA-N 4-amino-3-ethoxycarbonylbenzoic acid Chemical compound CCOC(=O)C1=CC(C(O)=O)=CC=C1N MQVAHEBEWAKTBK-UHFFFAOYSA-N 0.000 abstract 1
- XEOVONVMDYDZRL-UHFFFAOYSA-N 4-amino-3-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC(C(O)=O)=CC=C1N XEOVONVMDYDZRL-UHFFFAOYSA-N 0.000 abstract 1
- JDUYMWSYTIJMJO-UHFFFAOYSA-N 4-hydroxy-3-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC(C(O)=O)=CC=C1O JDUYMWSYTIJMJO-UHFFFAOYSA-N 0.000 abstract 1
- JIWBFQWPLSWTBT-UHFFFAOYSA-N 4-methoxy-3-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC(C(O)=O)=CC=C1OC JIWBFQWPLSWTBT-UHFFFAOYSA-N 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- -1 benzylthio Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 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
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1380095 Carboxamidobenzoic acids PFIZER Inc 30 Oct 1972 [2 Nov 1971] 49999/72 Heading C2C The invention comprises compounds of formula and the pharmaceutically acceptable salts thereof, wherein R 1 and R 2 independently represent H, C 1-4 alkyl, phenylalkyl and substituted phenylalkyl wherein said alkyl contains 1 to 2 carbon atoms and said substituent is F, Cl, Br, -CH 3 or -OCH 3 ; R 1 and R 2 when taken together with the nitrogen to which they are attached form a heterocyclic ring of formula wherein Z is O, S, NH and (CH 2 ) 0-3 , and methyl, benzyl and dimethyl substituted derivatives of said heterocyclic rings; and X is F, Cl, Br, -OCH 3 , -SCH 3 . -S-CH 2 -C 6 H 5 and substituted benzylthio wherein said substituent is selected from F, Cl, Br, -CF 3 , -CH 3 or a -OCH 3 group. These compounds are obtained by the following reaction scheme Preparation of the following intermediate compounds is given: in Preparation A(a), 3 - Carbomethoxy - 4 - chlorobenzoic acid by diazotizing 3-carboethoxy-4-aminobenzoic acid and treating the product compound with CuCl (in Preparation A(b) and A(c) 4-Br-and 4-Flderivatives are prepared); in Preparation A(d), 3-carbomethoxy-4-methoxybenzoic acid prepared by diazotizing 3-carbomethoxy-4-amino-benzoic acid to obtain 3-carbomethoxy-4-hydroxybenzoic acid which is later on treated with CH 3 I (for similar compounds see also Preparation "B"); in Preparation A(e), 3-carbomethoxy-4- methylthiobenzoic acid prepared by treating 3-carbomethoxy-4-chlorobenzoic acid with CH 3 SH (similar other compounds are also mentioned; N,α,dimethyl-p-methoxybenzylamine prepared by treating p-methoxyacetophenone with methyl amine in Preparation C(a); in Preparation C(b), N-ethyl-2-p-chloro-phenylamine is obtained by treating 2-p-chlorophenethylamine with CH 3 CHO, and reducing the product thus obtained with NaBH 4 ; in Preparation D, 4-fluorobenzyl mercaptan is obtained by treating 4-fluorobenzyl chloride with thiourea (preparation of other substituted mercaptans is also mentioned).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19492271A | 1971-11-02 | 1971-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1380095A true GB1380095A (en) | 1975-01-08 |
Family
ID=22719403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4999972A Expired GB1380095A (en) | 1971-11-02 | 1972-10-30 | Carboxamidobenzoic acids as hypolipemic agents |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3725417A (en) |
| JP (1) | JPS5653536B2 (en) |
| BE (1) | BE790859A (en) |
| DE (1) | DE2253748A1 (en) |
| FR (1) | FR2158444B1 (en) |
| GB (1) | GB1380095A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1476633A (en) * | 1973-10-03 | 1977-06-16 | Unilever Ltd | Dentifrice composition |
| DE2639935A1 (en) * | 1976-09-04 | 1978-03-09 | Hoechst Ag | BENZOESAEURS AND METHOD FOR THEIR PRODUCTION |
| JPS6058224B2 (en) * | 1978-07-31 | 1985-12-19 | 旭化成株式会社 | Method for producing metoclopramide |
| US6525078B1 (en) | 2002-06-25 | 2003-02-25 | Cesare Casagrande | Compound for the treatment of atherosclerotic-thrombotic pathological conditions |
| US8084645B2 (en) * | 2003-09-19 | 2011-12-27 | Chugai Seiyaku Kabushiki Kaisha | 4-phenylamino-benzaldoxime derivatives and uses thereof as mitogen-activated protein kinase kinase (MEK) inhibitors |
| TWI361066B (en) * | 2004-07-26 | 2012-04-01 | Chugai Pharmaceutical Co Ltd | 5-substituted-2-phenylamino benzamides as mek inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3268526A (en) * | 1962-09-12 | 1966-08-23 | Monsanto Co | Heterocyclic polyhalobenzamide derivatives |
-
0
- BE BE790859D patent/BE790859A/en not_active IP Right Cessation
-
1971
- 1971-11-02 US US00194922A patent/US3725417A/en not_active Expired - Lifetime
-
1972
- 1972-10-30 GB GB4999972A patent/GB1380095A/en not_active Expired
- 1972-11-02 JP JP10955672A patent/JPS5653536B2/ja not_active Expired
- 1972-11-02 DE DE2253748A patent/DE2253748A1/en active Pending
- 1972-11-02 FR FR7238764A patent/FR2158444B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3725417A (en) | 1973-04-03 |
| BE790859A (en) | 1973-04-30 |
| FR2158444B1 (en) | 1975-10-31 |
| DE2253748A1 (en) | 1973-05-30 |
| FR2158444A1 (en) | 1973-06-15 |
| JPS4861448A (en) | 1973-08-28 |
| JPS5653536B2 (en) | 1981-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |