IL41476A - Picolinic acid derivatives,their manufacture and pharmaceutical compositions containing them - Google Patents
Picolinic acid derivatives,their manufacture and pharmaceutical compositions containing themInfo
- Publication number
- IL41476A IL41476A IL41476A IL4147673A IL41476A IL 41476 A IL41476 A IL 41476A IL 41476 A IL41476 A IL 41476A IL 4147673 A IL4147673 A IL 4147673A IL 41476 A IL41476 A IL 41476A
- Authority
- IL
- Israel
- Prior art keywords
- pyridine
- butyl
- compound
- methoxy
- amino
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims 9
- 238000004519 manufacturing process Methods 0.000 title claims 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 28
- 238000000034 method Methods 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- -1 pyridine compound Chemical class 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 5
- 125000003277 amino group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- QEEGJLSZBDISLG-UHFFFAOYSA-N 5-butyl-4-methoxypyridine-2-carboxylic acid Chemical compound CCCCC1=CN=C(C(O)=O)C=C1OC QEEGJLSZBDISLG-UHFFFAOYSA-N 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 159000000007 calcium salts Chemical class 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- WSRJWHWKBDHVGA-UHFFFAOYSA-N 5-butyl-4,6-dimethoxypyridine-2-carboxylic acid Chemical compound CCCCC1=C(OC)C=C(C(O)=O)N=C1OC WSRJWHWKBDHVGA-UHFFFAOYSA-N 0.000 claims 1
- PKZMJGHIEXFEHC-UHFFFAOYSA-N 5-butyl-4-methoxy-6-piperidin-1-ylpyridine-2-carboxylic acid Chemical compound CCCCC1=C(OC)C=C(C(O)=O)N=C1N1CCCCC1 PKZMJGHIEXFEHC-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000005237 alkyleneamino group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- ZUNWOYXJINYCNJ-UHFFFAOYSA-N methyl 5-butyl-4-chloro-6-oxo-1h-pyridine-2-carboxylate Chemical compound CCCCC1=C(Cl)C=C(C(=O)OC)N=C1O ZUNWOYXJINYCNJ-UHFFFAOYSA-N 0.000 claims 1
- QFAITDVDBDFACQ-UHFFFAOYSA-N methyl 5-butyl-6-chloro-4-piperidin-1-ylpyridine-2-carboxylate Chemical compound CCCCC1=C(Cl)N=C(C(=O)OC)C=C1N1CCCCC1 QFAITDVDBDFACQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Claims (1)
1. WHAT WE CLAIM IS: 1. A pyridine compound of the formula I in which alk is an alkyl group having 4 to 6 carbon atoms, stands for a hydroxy, lower alkoxy, cyclo-lower alkoxy or amino group, R^ and R^, independently of one another stand' for lower alkoxy, hydroxy, amino, mono- or di-lower alkyl-amino or lower alkyleneamino or halogen and one of the symbols and R^ may also represent a hydrogen atom. 2V; A compound of the formula 0 in which R^ stands for a free hydroxyl group, a lower alkoxy group or the amino group, R^ and R^, independently of one another are each lower alkoxy, halogen or hydroxyl and one of the radicals -j and R^ can also be hydrogen, and alk is an alkyl group with 4 or 5 carbon atoms. 3. A compound of the formula 41 76-2 in which one of the symbols and R^ stands for lower alkoxy and the other for hydrogen or lower alkoxy and alk is an alkyl group with 4 or 5 carbon atoms . 4. A comp in which R^ stands for hydroxy, methoxy, ethoxy or free amino, R^ and R^, independently from one another, stand for chlorine, free hydroxyl, methoxy or ethoxy and one of the radicals R^ and R^ can also be hydrogen, and alk is an alkyl group with 4 or 5 carbon atoms. 5. A compound of the formula a in which R^ and R^, independently of one another, stand for methoxy or ethoxy and one of the symbols R-j and R^ may also stand for h dro en and alk n an al l r h r 41476-2 -carboxy-4-methoxy-5-n-butyl-pyridine . -carboxy-4 , 6-dichloro-5-n-butyl-pyridine . -carboxy-4-methoxy-5-n-butyl-6-chloro-pyridine . -carboxy-4-n-propoxy-5-n-buyl-pyridine . -carboxy^4-ethoxy-5-n-butyl-pyridine . -methoxycarbonyl-5-n-butyl-6-methoxy-pyridine . -carboxy-5-n-butyl-6-methoxy-pyridine . -methoxycarbonyl-4-chlord*-5-n-butyl-6-amino-pyridi e -methoxycarbonyl-5-n-butyl-6-amino-pyridine. 1 "' -meth0xycarbonyl-4-methoxy-5-n-butyl-pyridine . -carbamoyl-4-methoxy-5-n-butyl-pyridine. -carboxy-4-methoxy-5-isoamyl-pyridine. -carboxy-4-methoxy-5-n-amyl-pyridine . -methoxycarbonyl-4-piperidino-5-n-butyl-pyridine .. 41476-2- 20. 2-methoxycarbonyl-4-piperidino-5-n-butyl-6-chloro-pyridine . 21. 2-carboxy-4-chloro-5-n-bucyl-6-meChoxy-pyridine. 22. 2-carboxy-4-methoxy-5-n-butyl-6-piperidino-pyridine . 23. 2-carboxy-4,6-dimethoxy-5-n-butyl-pyridine . 24. 2-methoxycarbonyl-4-chloro-5-n-butyl-6-hydroxy-pyridine. 25. A salt of a compound as claimed in any one of claims 1 to 24. 26. An acid addition salt of a compound as claimed in any one of claims 1 to 24. 27. A therapeutically acceptable acid addition salt of a. compound as claimed in any one of claims 1 to 24. 28. A salt with a base of an acid as claimed in any one of claims 1 to 10, 12, 17, 18 and 21 to 23. 29. A therapeutically acceptable salt with :a base of an acid as claimed in any one of claims 1 to 10, 12, 17, 18 and 21 to 23. 30. A therapeutically acceptable metal salt of an acid as claimed in any one of claims 1 to 10, 12, 17, 18 and 21 to 23. 31. A pharmaceutical composition containing a compound as claimed in any one of claims 1 to 24, 27, 29 and 30 in admixture or conjunction with a pharmaceutical excipient. 32. A pharmaceutical composition containing an anti-hyper-tensively acitve aminoacid and a compound as claimed in any one of claims 1 to 24, 27, 29 and 30 in admixture or conjunction with a pharmaceutical excipient. 33. A pharmaceutical composition according to claim 32, containing a compound of the type of a-methyldopa as the anti-hypertensively active aminoacid. Λ 34. A pharmaceutical composition according to claim 33, containing, as the compound of the type of a-methyldopa, an α-amino-a-methyl-fl-hydroxyphenyl-propionic acid, one of its therapeutically acceptable salts or one of its esters. 35. A pharmaceutical composition according to claim 33, containing, as the compound of the type of α-methyldopa, a-amino-a-methyl-fi- (4-hydroxyphenyl) -propionic acid, a-amino-a-methyl-fl- (3 ,4-dihydroxyphenyl) -propionic acid, a therapeutically acceptable salt thereof or a lower alkyl ester thereof, and a compound as claimed in any one of claims 1 to 24, 27 29 and 30. 36. A pharmaceutical composition according to claim 33 containing, a) a-amino-a-methyl-fl- (3, -dihydroxyphenyl) -propionic acid or an alkali metal salt thereof, and b) 2-carbbxy-4-methoxy-5-n-butyl-pyridine or a non-toxic salt thereof. 37. A pharmaceutical composition according to any one of claims 32 to 36, containing 100-200 mg of a-amino-a-methyl-fl-(3, -dihydroxyphenyl) -propionic acid and 50-200 mg of the calcium salt of 2-carboxy-4-methoxy-5-n-butyl-pyridine . ' ;,< 38. A pharmaceutical composition according to any one of claims 32 to 27, containing 150-200 mg of a-amino- -methyl-fi-(3 ,4-dihydroxyphenyl) -propionic acid and 100-200 mg of the calcium salt of 2-carboxy-4-methoxy-5-n-butyl-pyridine . 39. A process for the manufacture of a pyridine compound as claimed in claim 1 or of a salt thereof, characterised in that a compound of the formula wherein alk, R.-, an< ^ave meanings given in claim 1 hydrate thereof, is oxidised and, if desired, in 41476-compounds obtained substituents are introduced, modified or split off within the framework of the definition of the final substances, or compounds obtained are converted into other final substances, and/or racemates obtained are split into the optical antipodes, and/or free compounds obtained are converted into their salts or salts obtained are converted into free compounds or other salts. AO, A process according to claim 39, characterised in that in compounds obtained esterified carboxyl groups, carbamoyl groups or thiocarbamoyl groups are hydrolysed to free carboxyl groups. . :. , 41. Process according to claim 39 or 40, characterised in that in compounds obtained free or esterified carboxyl groups are converted into carbamoyl groups. 42. A process according of any one of claims 3 ;to 41 , characterised in that in compounds obtained free carboxyl groups are esterified. 43. Process according to any one of claims 39 to 42, characterised in that in compounds obtained hydroxyl groups are etherified . 44. Process according to any one of claims 39 to 43, characterised in that in compounds obtained alkoxy groups are converted into hydroxyl groups. . 41476-2 45. Process according to any one of claims 39 to 44, characterised in that in compounds obtained which contain a mono- or di-lower alk lamino group or a lower alkylenamino group, this group is oxidised to a free amino group. 46. A process according to any one of claims 39 to 45, characterised in that in compounds obtained halogen is splitt off by reduction. 47. A process according to any one of claims 39 -to :45, ! characterised in that in compounds obtained halogen is converted into an amino group. 48. A process according to any one of claims 39 to 45 , characterised in that in compounds obtained halogen is ,converted into hydroxyl or alkoxy. 49. A process according to any one of claims 39 to 48, characterised in that in compounds obtained amino groups which posses at least one hydrogen atom are substituted. 50. A process according to any one of claims 39 to 49, characterised in that a compound obtainable as an intermediate product at any stage of the process is used as the starting compound and the missing process steps are carried out, or the process is stopped at any stage or a starting substance is formed under the reaction conditions, or a reactant is employed, if appropriate, in the form of one of its deri-, vatives. 41476-2 51. Process according to claim 50, characterised in that a compound of the formula wherein R^, R4 and alk have the meanings given in claim 1 and X' is methyl, hydroxymethyl, halogenomethyl, vinyl or styryl is oxidised. ' ί =· · .
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH230172A CH570376A5 (en) | 1972-02-17 | 1972-02-17 | |
| CH1354372 | 1972-09-15 | ||
| CH1872972 | 1972-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41476A0 IL41476A0 (en) | 1973-04-30 |
| IL41476A true IL41476A (en) | 1976-06-30 |
Family
ID=27173606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41476A IL41476A (en) | 1972-02-17 | 1973-02-06 | Picolinic acid derivatives,their manufacture and pharmaceutical compositions containing them |
Country Status (9)
| Country | Link |
|---|---|
| AR (3) | AR204708A1 (en) |
| DD (1) | DD104977A5 (en) |
| EG (1) | EG10917A (en) |
| ES (1) | ES411657A1 (en) |
| HU (1) | HU171241B (en) |
| IE (1) | IE37260B1 (en) |
| IL (1) | IL41476A (en) |
| PH (1) | PH10009A (en) |
| RO (1) | RO62813A (en) |
-
1973
- 1973-01-01 AR AR25125873A patent/AR204708A1/en active
- 1973-02-06 IE IE18373A patent/IE37260B1/en unknown
- 1973-02-06 IL IL41476A patent/IL41476A/en unknown
- 1973-02-13 RO RO7382573A patent/RO62813A/en unknown
- 1973-02-13 PH PH14343*A patent/PH10009A/en unknown
- 1973-02-15 EG EG6173A patent/EG10917A/en active
- 1973-02-15 DD DD16893973A patent/DD104977A5/xx unknown
- 1973-02-16 HU HU73CI00001343A patent/HU171241B/en unknown
- 1973-03-15 ES ES411657A patent/ES411657A1/en not_active Expired
- 1973-11-29 AR AR25125773A patent/AR200160A1/en active
-
1974
- 1974-09-24 AR AR25571574A patent/AR202045A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| RO62813A (en) | 1977-11-15 |
| ES411657A1 (en) | 1977-03-01 |
| IE37260L (en) | 1973-08-17 |
| PH10009A (en) | 1976-07-13 |
| HU171241B (en) | 1977-12-28 |
| IE37260B1 (en) | 1977-06-08 |
| DD104977A5 (en) | 1974-04-05 |
| AR200160A1 (en) | 1974-10-24 |
| EG10917A (en) | 1976-08-31 |
| AR204708A1 (en) | 1976-02-27 |
| IL41476A0 (en) | 1973-04-30 |
| AR202045A1 (en) | 1975-05-09 |
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