GB1389461A - Pyridine-acetic acid derivatives - Google Patents
Pyridine-acetic acid derivativesInfo
- Publication number
- GB1389461A GB1389461A GB2313172A GB2313172A GB1389461A GB 1389461 A GB1389461 A GB 1389461A GB 2313172 A GB2313172 A GB 2313172A GB 2313172 A GB2313172 A GB 2313172A GB 1389461 A GB1389461 A GB 1389461A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrrol
- reaction
- pyridine
- ethyl
- 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
- BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical class OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 11
- -1 Diethyl α - methyl - α - [6 - (pyrrol - 1 - yl)- pyrid - 3 - yl]malonate Chemical compound 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- KZQUJTWEUSKPAW-UHFFFAOYSA-N 2-(6-pyrrol-1-ylpyridin-3-yl)acetonitrile Chemical compound N#CCC1=CC=C(N=C1)N1C=CC=C1 KZQUJTWEUSKPAW-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- CKUZZJJDLFBRDE-UHFFFAOYSA-N 2-(6-aminopyridin-1-ium-3-yl)acetate Chemical compound NC1=CC=C(CC(O)=O)C=N1 CKUZZJJDLFBRDE-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 abstract 2
- RRLVTAJCJYQUOQ-UHFFFAOYSA-N (6-pyrrol-1-ylpyridin-3-yl)methanol Chemical compound N1(C=CC=C1)C1=CC=C(C=N1)CO RRLVTAJCJYQUOQ-UHFFFAOYSA-N 0.000 abstract 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- FCBNNNVKBVPTQD-UHFFFAOYSA-N 1-[5-(carboxymethyl)pyridin-2-yl]pyrrole-2-carboxylic acid Chemical compound C(=O)(O)C=1N(C=CC1)C1=CC=C(C=N1)CC(=O)O FCBNNNVKBVPTQD-UHFFFAOYSA-N 0.000 abstract 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 abstract 1
- FGPWGABEDLQFRU-UHFFFAOYSA-N 2-(6-pyrrol-1-ylpyridin-3-yl)propanenitrile Chemical compound CC(C#N)C=1C=NC(=CC=1)N1C=CC=C1 FGPWGABEDLQFRU-UHFFFAOYSA-N 0.000 abstract 1
- SDJJQJOGWQGRFO-UHFFFAOYSA-N 2-[6-(2-methoxycarbonylpyrrol-1-yl)pyridin-3-yl]acetic acid Chemical compound COC(=O)C=1N(C=CC1)C1=CC=C(C=N1)CC(=O)O SDJJQJOGWQGRFO-UHFFFAOYSA-N 0.000 abstract 1
- DPAQLBWVPFVTCA-UHFFFAOYSA-N 5-(chloromethyl)-2-pyrrol-1-ylpyridine Chemical compound N1(C=CC=C1)C1=NC=C(C=C1)CCl DPAQLBWVPFVTCA-UHFFFAOYSA-N 0.000 abstract 1
- RXSLHYTZMIUANX-UHFFFAOYSA-N 6-acetamidopyridine-3-carboxylic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=N1 RXSLHYTZMIUANX-UHFFFAOYSA-N 0.000 abstract 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 abstract 1
- AANHOZJYHCPPDQ-UHFFFAOYSA-N N-[5-(cyanomethyl)pyridin-2-yl]acetamide Chemical compound C(C)(=O)NC1=CC=C(C=N1)CC#N AANHOZJYHCPPDQ-UHFFFAOYSA-N 0.000 abstract 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- QLFNUXTWJGXNLH-UHFFFAOYSA-N bis(2-methoxyethoxy)alumane Chemical compound COCCO[AlH]OCCOC QLFNUXTWJGXNLH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- VHNHKYPWFYTCGR-UHFFFAOYSA-N ethyl 2-(6-pyrrol-1-ylpyridin-3-yl)acetate Chemical compound C(C)OC(CC=1C=NC(=CC1)N1C=CC=C1)=O VHNHKYPWFYTCGR-UHFFFAOYSA-N 0.000 abstract 1
- FIKVWPJKNMTBBD-UHFFFAOYSA-N ethyl 6-aminopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(N)N=C1 FIKVWPJKNMTBBD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- YUDUYCUJCQMCCJ-UHFFFAOYSA-N methyl 2,5-dimethoxyoxolane-2-carboxylate Chemical compound COC1CCC(OC)(C(=O)OC)O1 YUDUYCUJCQMCCJ-UHFFFAOYSA-N 0.000 abstract 1
- SGBVTSMREKMKRA-UHFFFAOYSA-N n-[5-(hydroxymethyl)pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=CC=C(CO)C=N1 SGBVTSMREKMKRA-UHFFFAOYSA-N 0.000 abstract 1
- 239000011664 nicotinic acid Substances 0.000 abstract 1
- 235000001968 nicotinic acid Nutrition 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH737571A CH557364A (de) | 1971-05-19 | 1971-05-19 | Verfahren zur herstellung neuer pyridinessigsaeurederivate. |
| CH569372 | 1972-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1389461A true GB1389461A (en) | 1975-04-03 |
Family
ID=25698215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2313172A Expired GB1389461A (en) | 1971-05-19 | 1972-05-17 | Pyridine-acetic acid derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3786044A (enExample) |
| AR (4) | AR198489A1 (enExample) |
| AT (5) | AT326125B (enExample) |
| BE (1) | BE783647A (enExample) |
| CA (1) | CA967161A (enExample) |
| DE (1) | DE2222791A1 (enExample) |
| FR (1) | FR2138158B1 (enExample) |
| GB (1) | GB1389461A (enExample) |
| NL (1) | NL7206754A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE385883B (sv) * | 1972-04-10 | 1976-07-26 | Ciba Geigy Ag | Forfarande for framstellning av nya pyridinkarbonsyraestrar |
| CH578531A5 (enExample) * | 1972-08-16 | 1976-08-13 | Ciba Geigy Ag | |
| IT1192287B (it) * | 1977-11-14 | 1988-03-31 | Fujisawa Pharmaceutical Co | Derivati di acido cefalosporanico ad azione farmaceutica e relativo procedimento di preparazione |
| FR2536748A1 (fr) * | 1982-11-25 | 1984-06-01 | Roussel Uclaf | Nouveaux esters derives d'acides 2,2-dimethyl cyclopropane carboxyliques et d'alcools biaryliques, leur procede de preparation et leur application a la lutte contre les parasites |
| CN112250618B (zh) * | 2020-11-06 | 2023-07-07 | 内蒙古佳瑞米精细化工有限公司 | 一种多氯代吡啶化合物与导热油混合物的分离方法 |
-
1972
- 1972-05-10 DE DE19722222791 patent/DE2222791A1/de active Pending
- 1972-05-15 US US00253615A patent/US3786044A/en not_active Expired - Lifetime
- 1972-05-17 GB GB2313172A patent/GB1389461A/en not_active Expired
- 1972-05-18 AT AT1034873A patent/AT326125B/de not_active IP Right Cessation
- 1972-05-18 AT AT1034773A patent/AT326124B/de not_active IP Right Cessation
- 1972-05-18 CA CA142,459A patent/CA967161A/en not_active Expired
- 1972-05-18 AT AT1034973A patent/ATA1034973A/de unknown
- 1972-05-18 AT AT434472A patent/AT325046B/de not_active IP Right Cessation
- 1972-05-18 BE BE783647A patent/BE783647A/xx unknown
- 1972-05-18 AT AT1034973A patent/AT326126B/de not_active IP Right Cessation
- 1972-05-18 NL NL7206754A patent/NL7206754A/xx unknown
- 1972-05-19 FR FR7218130A patent/FR2138158B1/fr not_active Expired
- 1972-05-19 AR AR242103A patent/AR198489A1/es active
-
1973
- 1973-03-29 AR AR247299A patent/AR198977A1/es active
- 1973-03-29 AR AR247300A patent/AR198978A1/es active
- 1973-03-29 AR AR247298A patent/AR198976A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7206754A (enExample) | 1972-11-21 |
| AR198977A1 (es) | 1974-07-31 |
| US3786044A (en) | 1974-01-15 |
| AT326124B (de) | 1975-11-25 |
| AR198976A1 (es) | 1974-07-31 |
| DE2222791A1 (de) | 1972-12-07 |
| FR2138158B1 (enExample) | 1975-06-20 |
| BE783647A (fr) | 1972-11-20 |
| AR198489A1 (es) | 1974-06-28 |
| ATA1034973A (de) | 1975-02-15 |
| AT326126B (de) | 1975-11-25 |
| CA967161A (en) | 1975-05-06 |
| AR198978A1 (es) | 1974-07-31 |
| AT325046B (de) | 1975-09-25 |
| FR2138158A1 (enExample) | 1972-12-29 |
| ATA1034773A (de) | 1975-02-15 |
| AT326125B (de) | 1975-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |