GB1396681A - Preparation of nitrophenylpyridines - Google Patents
Preparation of nitrophenylpyridinesInfo
- Publication number
- GB1396681A GB1396681A GB2699273A GB2699273A GB1396681A GB 1396681 A GB1396681 A GB 1396681A GB 2699273 A GB2699273 A GB 2699273A GB 2699273 A GB2699273 A GB 2699273A GB 1396681 A GB1396681 A GB 1396681A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitrophenyl
- alkyl
- pyridine
- pyridyl
- dihydro
- 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
- GEALTJGFPPNOJE-UHFFFAOYSA-N 3-nitro-2-phenylpyridine Chemical class [O-][N+](=O)C1=CC=CN=C1C1=CC=CC=C1 GEALTJGFPPNOJE-UHFFFAOYSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- AFVBDOPDKXFXTN-UHFFFAOYSA-N 4-(3-nitrophenyl)pyridine Chemical class [O-][N+](=O)C1=CC=CC(C=2C=CN=CC=2)=C1 AFVBDOPDKXFXTN-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 abstract 1
- BDSBSHZVSVKIHM-UHFFFAOYSA-N 3-pyridin-4-ylaniline Chemical compound NC1=CC=CC(C=2C=CN=CC=2)=C1 BDSBSHZVSVKIHM-UHFFFAOYSA-N 0.000 abstract 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005695 Ammonium acetate Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 alkyl propiolate Chemical compound 0.000 abstract 1
- 229940043376 ammonium acetate Drugs 0.000 abstract 1
- 235000019257 ammonium acetate Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 abstract 1
- YCVBJXPHYHMMRG-UHFFFAOYSA-N diethyl 2-[(3-pyridin-4-ylanilino)methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNC1=CC=CC(C=2C=CN=CC=2)=C1 YCVBJXPHYHMMRG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- MZESMDMSRBNRBO-UHFFFAOYSA-N ethyl 4-oxo-7-pyridin-4-yl-1h-quinoline-3-carboxylate Chemical compound C=1C=C2C(=O)C(C(=O)OCC)=CNC2=CC=1C1=CC=NC=C1 MZESMDMSRBNRBO-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
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- XBPZXDSZHPDXQU-UHFFFAOYSA-N rosoxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC=C1C1=CC=NC=C1 XBPZXDSZHPDXQU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 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
- C07D213/78—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US262001A US3922278A (en) | 1972-06-12 | 1972-06-12 | 4-(3-Nitrophenyl)-3,5-pyridinedicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1396681A true GB1396681A (en) | 1975-06-04 |
Family
ID=22995774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2699273A Expired GB1396681A (en) | 1972-06-12 | 1973-06-06 | Preparation of nitrophenylpyridines |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3922278A (https=) |
| JP (2) | JPS4961176A (https=) |
| CA (1) | CA999002A (https=) |
| GB (1) | GB1396681A (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088938A1 (de) * | 1982-03-13 | 1983-09-21 | Bayer Ag | Verwendung von Pyridinverbindungen zur Herstellung von Arzneimitteln mit antihypoxischer und Ischämie-protektiver Wirkung |
| EP0179239A3 (en) * | 1984-09-17 | 1986-08-13 | Sterling Drug Inc. | 7-(pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof |
| EP0219934A1 (en) * | 1985-08-10 | 1987-04-29 | Beecham Group Plc | Process for the preparation of aryl-piperidine esters |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2021387535A1 (en) * | 2020-11-30 | 2023-07-06 | George Kanianthara Chandy | POTENT AND SELECTIVE INHIBITORS OF THE CALCIUM-ACTIVATED POTASSIUM CHANNEL, KCa3.1, FOR USE AS PLATFORM THERAPEUTICS |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3441648A (en) * | 1967-02-07 | 1969-04-29 | Smithkline Corp | Compositions and methods for lowering blood pressure with 1,4-dihydropyridines |
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE1813436C3 (de) * | 1968-12-07 | 1979-01-11 | Bayer Ag, 5090 Leverkusen | N-Substituierte 2,6-Dimethyl-l,4dihydropyridine |
-
1972
- 1972-06-12 US US262001A patent/US3922278A/en not_active Expired - Lifetime
-
1973
- 1973-06-06 GB GB2699273A patent/GB1396681A/en not_active Expired
- 1973-06-11 CA CA173,774A patent/CA999002A/en not_active Expired
- 1973-06-12 JP JP48065502A patent/JPS4961176A/ja active Pending
-
1980
- 1980-06-12 JP JP7959580A patent/JPS5659759A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088938A1 (de) * | 1982-03-13 | 1983-09-21 | Bayer Ag | Verwendung von Pyridinverbindungen zur Herstellung von Arzneimitteln mit antihypoxischer und Ischämie-protektiver Wirkung |
| EP0179239A3 (en) * | 1984-09-17 | 1986-08-13 | Sterling Drug Inc. | 7-(pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof |
| EP0219934A1 (en) * | 1985-08-10 | 1987-04-29 | Beecham Group Plc | Process for the preparation of aryl-piperidine esters |
| US4861893A (en) * | 1985-08-10 | 1989-08-29 | Beecham Group Plc. | Chemical process |
Also Published As
| Publication number | Publication date |
|---|---|
| US3922278A (en) | 1975-11-25 |
| JPS4961176A (https=) | 1974-06-13 |
| CA999002A (en) | 1976-10-26 |
| JPS5659759A (en) | 1981-05-23 |
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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 |