US3558641A - Certain pyridyl salicylic acid derivatives - Google Patents
Certain pyridyl salicylic acid derivatives Download PDFInfo
- Publication number
- US3558641A US3558641A US673273A US3558641DA US3558641A US 3558641 A US3558641 A US 3558641A US 673273 A US673273 A US 673273A US 3558641D A US3558641D A US 3558641DA US 3558641 A US3558641 A US 3558641A
- Authority
- US
- United States
- Prior art keywords
- salicylic acid
- acid derivatives
- pyridyl
- heterocyclic
- preparation
- 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 - Lifetime
Links
- -1 pyridyl salicylic acid derivatives Chemical class 0.000 title description 4
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 title description 3
- 238000002360 preparation method Methods 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract description 5
- 230000001760 anti-analgesic effect Effects 0.000 abstract description 4
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 4
- 239000002221 antipyretic Substances 0.000 abstract description 4
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- GJSFZMHGFSKOAK-UHFFFAOYSA-N 2-hydroxy-5-pyridin-3-ylbenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C=NC=CC=2)=C1 GJSFZMHGFSKOAK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- WQTVIWDQIXIEOD-UHFFFAOYSA-N 4-pyridin-3-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=CN=C1 WQTVIWDQIXIEOD-UHFFFAOYSA-N 0.000 description 2
- KNLHNDZBUASBQF-UHFFFAOYSA-N 4-pyrimidin-4-ylphenol Chemical compound Oc1ccc(cc1)-c1ccncn1 KNLHNDZBUASBQF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010018691 Granuloma Diseases 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- LQGUURXDLDOJKX-UHFFFAOYSA-N chembl3245071 Chemical compound C1=C(O)C(C(=O)O)=CC(C=2N=CC=CC=2)=C1 LQGUURXDLDOJKX-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000011872 intimate mixture Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000009772 tissue formation Effects 0.000 description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YJGBYWQLSZIMJL-UHFFFAOYSA-N 2-hydroxy-5-thiophen-2-ylbenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C=2SC=CC=2)=C1 YJGBYWQLSZIMJL-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- VQHMPVXKDCHHSR-UHFFFAOYSA-N 4-pyridin-2-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=N1 VQHMPVXKDCHHSR-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- AFLHTYTXOOJJKV-UHFFFAOYSA-N 4-pyrimidin-4-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=NC=N1 AFLHTYTXOOJJKV-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- RUZWJMSQCFYNAM-UHFFFAOYSA-N 4-thiophen-2-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=CS1 RUZWJMSQCFYNAM-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- HIRQUAFTUYHOAP-UHFFFAOYSA-N chembl3245069 Chemical compound C1=C(O)C(C(=O)O)=CC(C=2N=CN=CC=2)=C1 HIRQUAFTUYHOAP-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003128 pregnanes Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Definitions
- This invention relates to new salicylic acid compounds and processes for producing the same, particularly the 5-(heterocyclic)-salicylic acid derivatives. These compounds are useful in that. they have anti-inflammatory activity and are effective in the prevention and inhibition of edema and granuloma tissue formation. In addition, some of them have a useful degree of ,anti-pyretic and analgesic activity.
- This invention relates to new heterocyclic phenyl conipounds and to processes for producing the same. More specifically, it relates to 5-(heterocyclic)-salicylic acid compounds (2-hydroxy-5-heterocyclic benzoic acids). Still R2 coon wherein:
- hetero atoms are either nitrogen, sulphur, or oxygen;
- this invention relates to compounds having the following general formula:
- 6-membered ring structure containing from 1-3 hetero atoms are 2,3 or 4-pyridyl, 2 or 3-pyrazinyl, 2,4 or 5-pyrimid1yl, 3 or 4-pyridazinyl, s-triazinyl, 3,4 or 6-as-triazinyl (1,2,3-triazinyl; 1,3,5'-triazinyl; 1,2,4-triazinyl).
- S-membered heterocyclic ring structures containing from 1-4 hetero atoms are:
- the R substituent on the heterocyclic nucleus can be in any available position and may be in one or more positions.
- the compounds described above have anti-inflammatory activity and are effective in the prevention and inhibition of edema and granuloma tissue formation.
- some of them have a useful degree of anti-pyretic and analgesic activity.
- they are normally administered orally in tablets or capsules, the optimum dosage depending on the particular compound being used and the type and severity of the condition being treated.
- oral dose levels of preferred compounds in the range of 50 mg. to 10 g. per day are useful in the control of said conditions, depend ing on the activity of the specific compound and the reaction sensitivity of the patient.
- the compounds of the instant invention are generally prepared by a carboxylation reaction wherein the appropriate starting material is reacted with carbon dioxide, preferably in the presence of potassium carbonate.
- the reaction is usually carried out in a pressurized vessel at a wide range of temperatures especially from about 50 C. to 200 C., preferably at about C'. at 800 p.s.i. initial pressure. The pressure can also vary from atmospheric pressure on up.
- the reaction is caried out for a sufficient time to consume the stoichiometric amount of carbon dioxide.
- the desired product can be isolated by extraction with water, the water layer then acidified and the precipitated product recrystallized.
- EXAMPLE 1 Preparation of 5-(2-thienyl)-salicylic acid A mixture of 5 g. of 2-(p-hydroxyphenyl)thiophene and 12 g. of anhydrous potassium carbonate in glass lined bomb is heated under a carbon dioxide atmosphere (800 p.s.i. initial pressure) at 175 C. for 8 hours. The material from the bomb is partitioned between water and methylene chloride, and the aqueous layer is acidified.
- a carbon dioxide atmosphere 800 p.s.i. initial pressure
- the precipitated product is dried and recrystallized from benzene/methanol, using charcoal to remove impurities, to obtain pure -(2-thienyl)-salicylic acid.
- EXAMPIJE 2 Preparation of 5-(2-pyridyl)-salicylic acid An intimate mixture of 8 g. of 2-(p-hydroxyphenyl) pyridine and 20 g. of anhydrous potassium carbonate is subjected to 800 p.s.i. of carbon dioxide in a glass liner in a pressure bomb, and the temperature raised to 200 C. for 6 hours. Maximum pressure during this time is 1,400 p.s.i. After cooling and venting, the contents of the bomb are taken up in 100 ml. of water and filtered. The filtrate is carefully treated with dilute hydrochloric acid until the pH is 7.5. The precipitated dark brown material is filtered and discarded. Upon careful acidification of the filtrate, the desired product precipitates. It is collected by filtration, taken up in dilute potassium bicarbonate solution and re-precipitated by careful neutralization. The product is recrystallized from methanol, yield 3.8 g., M.P. 266267 C.
- EXAMPLE 3 Preparation of 5-(3-pyridyl)-salicylic acid An intimate mixture of 1.6 g. of 3-(p-hydroxyphenyl)- pyridine, and 4 g. of anhydrous potassium carbonate is heated in a carbon dioxide atmosphere as described in the previous example. The 5-(3-pyridyl)-salicylic acid recrystallized from dimethyl formamide weighs 0.52 g., M.P. 263-265 C.
- EXAMPLE 4 Preparation of 2-hydroxy-5-(4-pyrimidyl)-benzoic acid ⁇ A mixture of 5 g. of 4-(p-hydroxyphenyl)pyrimidine (as prepared below) and 12 g. of anhydrous potassium carbonate is heated at 200 C. for 6 hours, under carbon dioxide at an initial pressure of 800 p.s.i. The product is Worked up in the usual way to obtain pure 2-hydroxy- 5-(4'-pyrimidyl)-benzoic acid.
- the mixture is cooled, and is neutralized by the gradual addition of sodium bicarbonate, with the addition of more water if necessary to keep the inorganic salts in solution.
- the crude product is filtered and washed with a little cold water. Recrystallization from benzene/hexane furnishes pure 4-(p-hydroxyphenyl)-pyrimidine.
- R is hydrogen, lower alkyl, lower alkoxy, halogen or haloloweralkyl
- R is hydrogen, lower alkyl, halo, amino, loweralkylamino, diloweralkylamino, hydroxy or lower alkoxy.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67327367A | 1967-10-06 | 1967-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3558641A true US3558641A (en) | 1971-01-26 |
Family
ID=24701969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US673273A Expired - Lifetime US3558641A (en) | 1967-10-06 | 1967-10-06 | Certain pyridyl salicylic acid derivatives |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3558641A (enrdf_load_stackoverflow) |
| BR (1) | BR6802728D0 (enrdf_load_stackoverflow) |
| CH (1) | CH502981A (enrdf_load_stackoverflow) |
| DE (1) | DE1801303A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1585315A (enrdf_load_stackoverflow) |
| GB (1) | GB1214079A (enrdf_load_stackoverflow) |
| NL (1) | NL161759C (enrdf_load_stackoverflow) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676451A (en) * | 1970-06-09 | 1972-07-11 | Merck & Co Inc | Thiazolylsalicylic acids |
| US3682968A (en) * | 1969-06-25 | 1972-08-08 | Merck & Co Inc | Anti-inflammatory salicylic acid derivatives |
| FR2128292A1 (en) * | 1971-03-12 | 1972-10-20 | Berlin Chemie Veb | Imidazole derivs - with hypotensive, mao-inhibitory, anticonvulsant antiinflammatory, choleretic and antiviral activity prepn |
| FR2128285A1 (en) * | 1971-03-11 | 1972-10-20 | Berlin Chemie Veb | Imidazole derivs - with hypotensive mao-inhibitory, anticonvulsant antiinflammatory choleretic and antiviral activity prepn |
| US3860640A (en) * | 1972-04-12 | 1975-01-14 | Nippon Shinyaku Co Ltd | 3-alkoxy-5-substituted phenylacetic acids |
| US3929833A (en) * | 1970-10-30 | 1975-12-30 | Sandoz Ag | Organic compounds |
| US3993763A (en) * | 1969-03-18 | 1976-11-23 | Ciba-Geigy Corporation | Tertiary aminoacids as anti-inflammatory agents |
| US4001420A (en) * | 1968-12-12 | 1977-01-04 | Science Union Et Cie, Societe Francaise De Recherche Medical | Thiazolyl benzoic acid compounds |
| US4111935A (en) * | 1975-01-02 | 1978-09-05 | Smith Kline & French Laboratories Limited | 3-chloro-6-phenylpyridazine compounds |
| US4152341A (en) * | 1975-12-29 | 1979-05-01 | Imperial Chemical Industries Limited | Triaryl or diarylpyridyl methanes |
| US4305950A (en) * | 1978-04-28 | 1981-12-15 | Basf Aktiengesellschaft | Pharmaceutical agent containing amino derivatives of 2-methyl-5-(2-hydroxystyryl)-1,3,4-thiadiazole |
| USRE31467E (en) * | 1975-12-29 | 1983-12-20 | Imperial Chemical Industries Plc | Triaryl or diarylpyridyl methanes |
| EP0195582A1 (en) * | 1985-03-14 | 1986-09-24 | SMITH KLINE DAUELSBERG GmbH | 5-Aminosalicylic acid derivatives of non-steroidal antiinflammatory acids |
| US5541219A (en) * | 1992-03-04 | 1996-07-30 | Rhone-Poulenc Rorer Limited | 1-Alkoxy-2-(alkoxy- or cycloalkoxy-)-4-(cyclothioalkyl- or cyclothioalkenyl-) benzenes as inhibitors of cyclic AMP phosphodiesterase and tumor necrosis factor |
| EP3593803A4 (en) * | 2017-03-10 | 2020-04-08 | Universidad de Granada | COMPOUNDS FOR THE TREATMENT OF DISEASES CAUSED BY THE ACCUMULATION OF OXALATE |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1308028A (en) * | 1970-06-12 | 1973-02-21 | Science Union & Cie | Thiazolylbenzoic acid derivatives and a process for their manufactur |
| US3687971A (en) * | 1970-06-22 | 1972-08-29 | Merck & Co Inc | 4-(pyrrolyl)-salicylic acid derivatives |
| US3865839A (en) * | 1973-03-01 | 1975-02-11 | Hoechst Co American | Thiopyranopyrrolylsalicyclic acids and derivatives thereof |
-
1967
- 1967-10-06 US US673273A patent/US3558641A/en not_active Expired - Lifetime
-
1968
- 1968-09-24 NL NL6813639.A patent/NL161759C/xx not_active IP Right Cessation
- 1968-09-30 BR BR202728/68A patent/BR6802728D0/pt unknown
- 1968-10-01 GB GB46606/68A patent/GB1214079A/en not_active Expired
- 1968-10-04 FR FR1585315D patent/FR1585315A/fr not_active Expired
- 1968-10-04 DE DE19681801303 patent/DE1801303A1/de active Pending
- 1968-10-07 CH CH1494368A patent/CH502981A/de not_active IP Right Cessation
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001420A (en) * | 1968-12-12 | 1977-01-04 | Science Union Et Cie, Societe Francaise De Recherche Medical | Thiazolyl benzoic acid compounds |
| US3993763A (en) * | 1969-03-18 | 1976-11-23 | Ciba-Geigy Corporation | Tertiary aminoacids as anti-inflammatory agents |
| US3682968A (en) * | 1969-06-25 | 1972-08-08 | Merck & Co Inc | Anti-inflammatory salicylic acid derivatives |
| US3676451A (en) * | 1970-06-09 | 1972-07-11 | Merck & Co Inc | Thiazolylsalicylic acids |
| US3929833A (en) * | 1970-10-30 | 1975-12-30 | Sandoz Ag | Organic compounds |
| FR2128285A1 (en) * | 1971-03-11 | 1972-10-20 | Berlin Chemie Veb | Imidazole derivs - with hypotensive mao-inhibitory, anticonvulsant antiinflammatory choleretic and antiviral activity prepn |
| FR2128292A1 (en) * | 1971-03-12 | 1972-10-20 | Berlin Chemie Veb | Imidazole derivs - with hypotensive, mao-inhibitory, anticonvulsant antiinflammatory, choleretic and antiviral activity prepn |
| US3860640A (en) * | 1972-04-12 | 1975-01-14 | Nippon Shinyaku Co Ltd | 3-alkoxy-5-substituted phenylacetic acids |
| US4111935A (en) * | 1975-01-02 | 1978-09-05 | Smith Kline & French Laboratories Limited | 3-chloro-6-phenylpyridazine compounds |
| US4152341A (en) * | 1975-12-29 | 1979-05-01 | Imperial Chemical Industries Limited | Triaryl or diarylpyridyl methanes |
| USRE31467E (en) * | 1975-12-29 | 1983-12-20 | Imperial Chemical Industries Plc | Triaryl or diarylpyridyl methanes |
| US4305950A (en) * | 1978-04-28 | 1981-12-15 | Basf Aktiengesellschaft | Pharmaceutical agent containing amino derivatives of 2-methyl-5-(2-hydroxystyryl)-1,3,4-thiadiazole |
| EP0195582A1 (en) * | 1985-03-14 | 1986-09-24 | SMITH KLINE DAUELSBERG GmbH | 5-Aminosalicylic acid derivatives of non-steroidal antiinflammatory acids |
| US5541219A (en) * | 1992-03-04 | 1996-07-30 | Rhone-Poulenc Rorer Limited | 1-Alkoxy-2-(alkoxy- or cycloalkoxy-)-4-(cyclothioalkyl- or cyclothioalkenyl-) benzenes as inhibitors of cyclic AMP phosphodiesterase and tumor necrosis factor |
| EP3593803A4 (en) * | 2017-03-10 | 2020-04-08 | Universidad de Granada | COMPOUNDS FOR THE TREATMENT OF DISEASES CAUSED BY THE ACCUMULATION OF OXALATE |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6813639A (enrdf_load_stackoverflow) | 1969-04-09 |
| CH502981A (de) | 1971-02-15 |
| DE1801303A1 (de) | 1969-06-19 |
| NL161759C (nl) | 1980-03-17 |
| NL161759B (nl) | 1979-10-15 |
| BR6802728D0 (pt) | 1973-05-10 |
| GB1214079A (en) | 1970-12-02 |
| FR1585315A (enrdf_load_stackoverflow) | 1970-01-16 |
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