CH623563A5 - Process for the preparation of carboxylic acids and carboxylic acid derivatives - Google Patents
Process for the preparation of carboxylic acids and carboxylic acid derivatives Download PDFInfo
- Publication number
- CH623563A5 CH623563A5 CH746576A CH746576A CH623563A5 CH 623563 A5 CH623563 A5 CH 623563A5 CH 746576 A CH746576 A CH 746576A CH 746576 A CH746576 A CH 746576A CH 623563 A5 CH623563 A5 CH 623563A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- group
- sep
- compounds
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 title abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 230000010933 acylation Effects 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- DUCNKBZIKNAQOS-UHFFFAOYSA-N O=[C]C1=CC=CN=C1 Chemical compound O=[C]C1=CC=CN=C1 DUCNKBZIKNAQOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 210000002966 serum Anatomy 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical class O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 238000005915 ammonolysis reaction Methods 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
- 229960001214 clofibrate Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- KFDJHBMMMPHERQ-UHFFFAOYSA-N methyl 2-(n-[2-acetyloxy-3-(4-chlorophenyl)sulfanylpropyl]anilino)acetate Chemical compound C=1C=CC=CC=1N(CC(=O)OC)CC(OC(C)=O)CSC1=CC=C(Cl)C=C1 KFDJHBMMMPHERQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
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)
- 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)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50074015A JPS51149235A (en) | 1975-06-17 | 1975-06-17 | Process for preparation of novel carboxylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623563A5 true CH623563A5 (en) | 1981-06-15 |
Family
ID=13534839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH746576A CH623563A5 (en) | 1975-06-17 | 1976-06-11 | Process for the preparation of carboxylic acids and carboxylic acid derivatives |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS51149235A (es) |
| AT (1) | AT345800B (es) |
| CH (1) | CH623563A5 (es) |
| DD (1) | DD125905A5 (es) |
| ES (1) | ES448933A1 (es) |
| LU (1) | LU75171A1 (es) |
| PT (1) | PT65160B (es) |
-
1975
- 1975-06-17 JP JP50074015A patent/JPS51149235A/ja active Granted
-
1976
- 1976-05-31 PT PT65160A patent/PT65160B/pt unknown
- 1976-06-11 CH CH746576A patent/CH623563A5/de not_active IP Right Cessation
- 1976-06-14 AT AT431876A patent/AT345800B/de not_active IP Right Cessation
- 1976-06-15 LU LU75171A patent/LU75171A1/xx unknown
- 1976-06-16 ES ES448933A patent/ES448933A1/es not_active Expired
- 1976-06-17 DD DD193419A patent/DD125905A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD125905A5 (es) | 1977-06-01 |
| ES448933A1 (es) | 1977-07-01 |
| JPS549184B2 (es) | 1979-04-21 |
| PT65160B (en) | 1977-10-13 |
| JPS51149235A (en) | 1976-12-22 |
| ATA431876A (de) | 1978-02-15 |
| LU75171A1 (es) | 1977-01-26 |
| PT65160A (en) | 1976-06-01 |
| AT345800B (de) | 1978-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1928838A1 (de) | Roentgenkontrastmittel und Verfahren zu ihrer Herstellung | |
| DE3731542A1 (de) | Neue dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6-triiod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel | |
| DE2310031C3 (de) | 1 -Benzyl-1 H-indazol-3-carbonsäuren, -amide und -ester | |
| DE2127734A1 (de) | Neue Nitrofuranderivate und Verfahren zu ihrer Herstellung | |
| DE2446100B2 (de) | Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel | |
| CH623563A5 (en) | Process for the preparation of carboxylic acids and carboxylic acid derivatives | |
| DE1518337A1 (de) | Neue Roentgenkontrastmittel und Verfahren zur Herstellung derselben | |
| DE941193C (de) | Verfahren zur Herstellung von neuen, bisquaternaeren Phosphoniumverbindungen | |
| DE2407016C3 (de) | 2-Alkoxybenzoylaminocarbonsäuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antipyretische Mittel | |
| DE1493513C3 (de) | Sulfamylanthranilsäuren, deren therapeutisch verwendbare Salze, Verfahren zu ihrer Herstellung und diese enthaltenden pharmazeutischen Präparate | |
| AT344335B (de) | Verfahren zur herstellung von neuen derivaten des vitamins d2 bzw. d3 und des epi-vitamins d2 bzw. d3 | |
| DE2167282C2 (de) | Verfahren zur Herstellung der 7-[2-(1H-Tetrazol-1-yl)-acetamido]-3-(2-methyl-1,3,4-thiadiazol-5-yl)-thiomethyl-3-cephem-4-carbonsäure | |
| DE1126880B (de) | Verfahren zur Herstellung von Piperazinderivaten | |
| AT230364B (de) | Verfahren zur Herstellung von 9,10-Dihydroanthracenen und ihren Säureadditionssalzen | |
| DE934170C (de) | Verfahren zur Herstellung von m-Oxyanilinverbindungen | |
| CH622492A5 (es) | ||
| AT242138B (de) | Verfahren zur Herstellung von neuen Estern von quaternären Ammoniumverbindungen | |
| AT211816B (de) | Verfahren zur Herstellung von neuen polyjodierten Benzoylverbindungen | |
| DE938017C (de) | Verfahren zur Herstellung von quaternaeren Ammoniumsalzen von 4-Amino-2-(tert.-amino-alkoxy)-benzoesaeurealkylestern | |
| AT223188B (de) | Verfahren zur Herstellung neuer N,N-disubstituierter Monoaminoalkylamide und ihrer Salze | |
| DE1102747B (de) | Verfahren zur Herstellung von spasmolytisch wirksamen 1-Alkyl-4-acylpiperazinen | |
| DE1018869B (de) | Verfahren zur Herstellung von Aminoalkylpurinderivaten | |
| DE194051C (es) | ||
| AT340587B (de) | Verfahren zur herstellung neuer cephemderivate | |
| AT288413B (de) | Verfahren zur Herstellung neuer basischer Xanthonderivate und ihrer Salze |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |