GB2018753A - 5-Substituted picolinic acid derivatives, a process for preparation thereof and an anti-hypertensive composition containing the same - Google Patents
5-Substituted picolinic acid derivatives, a process for preparation thereof and an anti-hypertensive composition containing the sameInfo
- Publication number
- GB2018753A GB2018753A GB7910324A GB7910324A GB2018753A GB 2018753 A GB2018753 A GB 2018753A GB 7910324 A GB7910324 A GB 7910324A GB 7910324 A GB7910324 A GB 7910324A GB 2018753 A GB2018753 A GB 2018753A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- formula
- image
- same
- 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.)
- Granted
Links
- -1 5-Substituted picolinic acid Chemical class 0.000 title abstract 5
- 230000003276 anti-hypertensive effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000004411 aluminium Chemical group 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 125000002431 aminoalkoxy group Chemical group 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000011575 calcium Chemical group 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000011777 magnesium Chemical group 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229940081066 picolinic acid Drugs 0.000 abstract 1
- 239000011591 potassium Chemical group 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Chemical group 0.000 abstract 1
- 229910052708 sodium Inorganic materials 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
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A 5-substituted picolinic acid derivative of the formula (I): <IMAGE> wherein R1 represents a straight or branched chain halogen-substituted alkyl group having 2 to 6 carbon atoms or a substituted phenyl group having the formula <IMAGE> wherein each of R3 and R4, which may be the same or different, represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, an N-alkyl-substituted amino group, an acylamino group, an acetyl group, an acyloxy group, a hydroxy group or a halogen-substituted alkyl group or wherein R3 and R4, when taken together, represent a polymethylene chain; and R2 represents an -OM group wherein M represents hydrogen, sodium, potassium, calcium, aluminium, magnesium, a straight or branched chain or cyclic alkoxy group having 1 to 6 carbon atoms, an aminoalkoxy group, a phenoxy group, a substituted phenoxy group, a 5-indanyloxy group, an acyloxyalkyloxy group having the formula <IMAGE> wherein R5 represents a hydrogen atom or a methyl group and R6 represents a lower alkyl group having 1 to 6 carbon atoms, a phenyl group or a substituted phenyl group, or an amino group represented by the formula <IMAGE> wherein each of R7 and R8, which may be the same or different, represents a hydrogen atom, a lower alkyl group, or a phenyl group. 5-Indanyl ester of 5-alkoxy-picolinic acid represented by the formula (A): <IMAGE> wherein Ra represents an alkyl group having 1 to 6 carbon atoms. The above compounds are useful as anti-hypertensive agents. There is also disclosed a process for preparing such compounds and anti-hypertensive compositions containing the same.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3296778A JPS54125681A (en) | 1978-03-24 | 1978-03-24 | 5-substituted picolinic acid, its preparation, and hypotensive agent containing the same |
| JP3296678A JPS54125680A (en) | 1978-03-24 | 1978-03-24 | 5-alkoxypicolinic acid ester, its preparation, and hypotensive agent containing the same |
| JP8048578A JPS559002A (en) | 1978-07-04 | 1978-07-04 | 5-substituted picolinic acid derivative, its preparation and hypotensive agent containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2018753A true GB2018753A (en) | 1979-10-24 |
| GB2018753B GB2018753B (en) | 1982-08-25 |
Family
ID=27287919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7910324A Expired GB2018753B (en) | 1978-03-24 | 1979-03-23 | 5-substituted picolinic acid derivatives a process for preparation thereof and ananti-hypertensive composition containing the same |
Country Status (9)
| Country | Link |
|---|---|
| CA (1) | CA1115709A (en) |
| CH (1) | CH637941A5 (en) |
| DE (1) | DE2911492C2 (en) |
| ES (1) | ES478918A1 (en) |
| FR (1) | FR2422639A1 (en) |
| GB (1) | GB2018753B (en) |
| IT (1) | IT1115064B (en) |
| NL (1) | NL178251C (en) |
| SE (1) | SE446863B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5344572A (en) * | 1976-09-30 | 1978-04-21 | Meiji Seika Kaisha Ltd | 5-alkoxy-picolic acid, its preparation and hypotensives containing the same |
-
1979
- 1979-03-21 CA CA323,912A patent/CA1115709A/en not_active Expired
- 1979-03-22 CH CH268779A patent/CH637941A5/en not_active IP Right Cessation
- 1979-03-22 IT IT48451/79A patent/IT1115064B/en active
- 1979-03-23 SE SE7902665A patent/SE446863B/en not_active IP Right Cessation
- 1979-03-23 ES ES478918A patent/ES478918A1/en not_active Expired
- 1979-03-23 GB GB7910324A patent/GB2018753B/en not_active Expired
- 1979-03-23 FR FR7907345A patent/FR2422639A1/en active Granted
- 1979-03-23 DE DE2911492A patent/DE2911492C2/en not_active Expired
- 1979-03-23 NL NLAANVRAGE7902306,A patent/NL178251C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1115709A (en) | 1982-01-05 |
| SE7902665L (en) | 1979-09-25 |
| CH637941A5 (en) | 1983-08-31 |
| DE2911492C2 (en) | 1983-05-05 |
| FR2422639B1 (en) | 1983-05-20 |
| FR2422639A1 (en) | 1979-11-09 |
| IT7948451A0 (en) | 1979-03-22 |
| DE2911492A1 (en) | 1979-09-27 |
| NL178251B (en) | 1985-09-16 |
| GB2018753B (en) | 1982-08-25 |
| SE446863B (en) | 1986-10-13 |
| NL178251C (en) | 1986-02-17 |
| NL7902306A (en) | 1979-09-26 |
| ES478918A1 (en) | 1979-12-16 |
| IT1115064B (en) | 1986-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930323 |