IE49081B1 - Imidazolylethoxy derivatives of pyridine-5-methanols and quinoline-3-methanols - Google Patents
Imidazolylethoxy derivatives of pyridine-5-methanols and quinoline-3-methanolsInfo
- Publication number
- IE49081B1 IE49081B1 IE1894/79A IE189479A IE49081B1 IE 49081 B1 IE49081 B1 IE 49081B1 IE 1894/79 A IE1894/79 A IE 1894/79A IE 189479 A IE189479 A IE 189479A IE 49081 B1 IE49081 B1 IE 49081B1
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- chloro
- halogen
- hydrogen
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- 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
- C07D213/61—Halogen atoms or nitro radicals
Abstract
Imidazolylethoxy derivatives of pyridin-5-methanols and quinolin-3- methanols having the general formulae: and and their acid addition salts may be used as antifungal and antibacterial agents R<1> to R<10> each is H, alkyl, alkoxy, alkylthio, hydroxy or halogen.
Description
Imidazolylethoxy Derivatives of Pyridin-5-Methanols and
Quinolin-3-Methanols
This invention relates to new 2-(1H-imidazoll-yl) ethoxy derivatives of pyridin-5-methanols, quinolin-3-methanols, and the acid addition salts of these compounds. These new compounds are represented by the following formulae:
The symbols have the following meaning in Formulae I and II and throughout the specification:
R3· to each can be hydrogen, hydroxy, halogen, lower alkoxy, lower alkylthio or lower alkyl.
The term lower alkyl includes straight or branched chain hydrocarbons containing 1 to 7 carbon atoms. Examples include methyl, ethyl, propyl, isopropyl and the like. The term lower alkoxy and lower alkylthio include such lower alkyl groups bonded to an oxygen or sulfur, respectively, e.g., methoxy, ethoxy, propoxy, butoxy, t-butoxy, methylthio, ethylthio, propylthio, butylthio, isobutylthio, etc. In all of these the C^-C^ lower alkyl groups are preferred, and the C^-C2, are especially preferred.
The halogens are the four common halogens, chlorine and bromine being preferred in that order. Preferably, all halogens in a single oompound are the same.
Preferred embodiments of this invention are compounds of formula I and II wherein R1 to R10 can be hydrogen, lower alkyl of 1 to 4 carbon atoms or halogen.
Most preferred embodiments of formula I are where 1 6
R to R is hydrogen, halogen or lower alkyl of 1 to 4 carbon atoms, most especially wherein R^ is hydrogen or C.-C^-alkyl, R2, , r5 and R® each is chlorine, and
R3 is hydrogen.
Preferred embodiments of formula (II) are compounds wherein R1, R^ and R10 each is hydrogen or halogen,
Q Q 6 especially hydrogen; R , R , R , R each is hydrogen or halogen, especially halogen and most especially 5 6 chlorine, and R and R are attached in the 2- and 4position of the phenyl ring, respectively.
The new compounds of formula I are formed by the following series of reactions.
4908 1
A pyridine-5-carboxylic acid ester of the fonnula (III)
is reduced by means of a reducing agent, e.g., a metal hydride such as lithium aluminum hydride or sodium borohydride , to give the alcohol
The alcohol of formula IV is then converted to the halomethyl derivative of the formula (V)
wherein X represents a halogen, preferably chlorine, bromine or iodine, by means of an inorganic acid halide such as thionyl chloride, phosphorus oxy49081 bromide, etc.
The product of formula I is then prepared byreaction of the halo compound of formula V with a substituted 1- (phenyl)-2-(lH-imidazol-l-yl)ethanol of the formula (VI)
The inorganic acid formed during the reaction is neutralized by a base, e.g., alkali metal hydroxide carbonate, amine, alcoholate or other similar agents known in the art.
The compounds of formula III, which are used as starting materials, are produced by the procedures described in C.R. Acad. Sci. Hebd., Sci. Ser. C 275, 1317(1972); Rec.trav.chim. 65, 129(1946); Chem. Ber. 93, 1848(1960). The compounds of formula VI which are used as starting materials are produced by the general method described in J. Med. Chem. 12, 784(1969).
The new compounds of formula II are formed by the following series of reactions.
A quinoline-3-carboxylic acid ester of the formula
4908 1 is reduced by means of a reducing agent, e.g. a metal hydride such as lithium aluminum hydride or sodium borohydride to give the alcohol of the formula
ch2~oh
The alcohol of formula VIII is converted to the halomethyl derivative of the formula
wherein X represents a halogen, preferably chlorine, bromine or iodine, by means of an inorganic acid halide such as thionyl chloride, phosphorus oxybromide, etc.
The product of formula II is then prepared by reaction of the halo compound of formula IX with a substituted 1-(phenyl)-2-(lH-imidazol-l-yl)ethanol of the formula (X)
The inorganic acid formed during the reaction is neutralized by a base, e.g., alkali metal hydroxide, carbonate, amine, alcoholate or other similar bases known in the art.
The compounds of formula VII which are used as starting materials, are produced by the procedures described in Journal of Medicinal Chemistry, Vol. 20, 1001 (1977); ibid., Vol. 16 875 (1973) Tetrahedron Letters, 51, 4545 (1977), etc. The compounds of formula X (which are used as starting materials,are produced by the general methods described in Journal of Medicinal Chemistry, Vol. 12, 784 (1969).
9 0 8 1
The compounds of formulae I and II form salts which are also part of this invention. The salts include acid-addition salts, particularly the nontoxic, physiologically acceptable members. The bases of formulae I and II form salts by reaction with one or more equivalents of any of a variety of the common inorganic and organic acids providing acid addition salts including, for example, hydrohalides (especially hydrochloride and hydrobromide), sulfate, nitrate, borate, phosphate, oxalate, maleate, citrate, acetate, ascorbate, succinate, benzenesulfonate, methanesulfonate, cyclohexanesulfamate and toluenesulfonate. The acid addition salts frequently provide a convenient means for isolating or purifying the product, e.g., by forming and precipitating a salt (which is not necessarily non-toxic) in an appropriate medium in which the salt is insoluble, then after separation of the salt, neutralizing with a base such as barium hydroxide or sodium hydroxide, to obtain the free base of formula I. Other salts may then be formed from the free base by reaction with one or more equivalents of acid containing the desired acid group.
The new compounds of Formula I and II and their salts are useful as anti-fungal and anti-bacterial agents and may be used to combat infections in various mammalian species, such as mice, rats, dogs, guinea pigs and the like, particularly those due to organisms such as Candida albicans, as well as organisms such as Trichomonas vaginalis or Trichophyton mentagrophytes. For example, a compound or mixture of compounds of formula I and II or physiologically acceptable acid addition salt thereof can be administered orally to an infected animal, e.g., to a mouse, in an amount of about 5 to 25 mg. per kg. per day in 2 to 4 divided doses. These may be conventially formulated in a tablet, capsule or elixir containing about 10 to 250 mg. per dosage unit, by compounding the active substance or substances with the conventional excipient, vehicle, binder, preservative, flavor, etc., as called for by accepted pharmaceutical practice. Preferably they are applied topically, e.g., intravaginally in a lotion or in a conventional cream base at a concentration of about 0.01 to 3 percent by weight for a period of about 3 to 7 days, two to four times daily.
The following examples are illustrative of the invention. Temperatures are on the Celsius scale.
Example 1
2,4-Dichloro-5-[[1-(2,4-dichlorophenyl)-2-(lH-imidazol-1yl)ethoxy]methyl]pyridine, hydrochloride (lsl)
a) 2,4-Dichloropyridin-5-methanol
g. of 2,4-Diehloropyridin-5-carboxylic acid, ethyl ester (0.3 mol.) are dissolved in 120 ml. of anhydrous tetrahydrofuran. Nitrogen is passed through the flask and while stirring and cooling to 0°, 7.12 g of lithium aluminum hydride are added in portions in order to keep the reaction temperature in the range of 5 to 10°. Stirring is continued for an additional hours while cooling externally with ice water, and the mixture is allowed to stand overnight. While stirring and cooling the mixture with ice water, there are added 250 ml. of hydrochloric acid (3N) dropwise so that the reaction temperature does not exceed 5 to
8°. Then the acidic solution is evaporated in vacuo to dryness and the residual product is extracted with 500 ml. of chloroform. The chloroform extract is treated with charcoal, filtered and the solvent is distilled off, yielding 37.7 g. of 2,4-dichloropyrio din-5-methanol,m.p. 73-77 .
The salt product, which is the residue after extracting with chloroform is neutralized with sodium hydroxide and the salt mixture is again extracted with chloroform in a Soxhlet apparatus and this yields a second crop of 5.2 g. Total yield 42.9 g. (80%).
After recrystallization from hexane, the 2,4-dichloropyridin-5-methanol melts at 82-85°.
b) 5-Chloromethyl-2,4-dichloropyridine
.2 g. of 2,4-dichloropyridin-5-methanol (0.11 mol.) and 150 ml. of phosphorus oxychloride are refluxed for 19 hours. Then the excess phosphorus oxychloride is removed in vacuo and ice is added to the residue. 5-Chloromethyl-2,4-dichloro30 pyridine is filtered off, washed with water, dried in the desiccator over anc^ reerystallized from hexane; yield 17.95 g. (83%), m.p. 55-56°.
48081
c) 2,4-Dichloro-5-[[1-(2,4-dichlorophenyl)-2(IH-imidazol-l-yl)ethoxy]methyl]pyridine, hydrochloride (1:1)
In a three-necked flask, fitted with stirrer, reflux condenser and gas inlet tube 29.3 g. of sodium hydroxide (0.73 mol.) and 27 ml. of water are introduced. While passing nitrogen through the flask, the solution is cooled to 45° and then 7.71 g. of 1-(2,4-dichlorophenyl)-2-(IH-imidazol-l-yl)ethanol (0.03 mol.) [prepared by the method of J. Med. Chem.
12, 784 (1969)], 0.5 g. of benzyltrimethylammonium chloride and 30 ml. of tetrahydrofuran are added. To the mixture, which is warmed to 50°, 5.9 g. of 5-chloromethyl-2,4-dichloropyridine are added and the mixture is stirred vigorously for two hours at 60°. The filtered biphasic solution is transferred into a separating funnel, the lower aqueous sodium hydroxide is extracted with 10 ml. of tetrahydrofuran. The combined tetrahydrofuran layers are treated with charcoal and dried by means of sodium sulfate. Ether is then added to the tetrahydrofuran extract in order to remove an oily by-product. To the clear solution of the free base alcoholic hydrochloric acid is added dropwise. The precipitated 2,4-dichloro-5[[1- (2,4-dichlorophenyl)-2-(lH-imidazol-l-yl)ethoxy]methyl]pyridine, hydrochloride (3.5 g.) is treated with acetonitrile. A second crop is obtained byremoving the tetrahydrofuran/alcohol mother liquor and treating the residue with acetonitrile (3.5 g.), m.p. 177°. Total yield 7 g. (52%). Recrystallization from acetonitrile elevates the melting point to 181-182°.
4908 1
Example 2
2.4- Dichloro-6-methyl-5-[(1-(2,4-dichlorophenyl)-2(IH-imidazol-l-yl) ethoxy]methy1]pyridine, hydrochloride
By substituting 0.3 ml. of 2,4-dichloro-65 methylpyridin-5-carboxylic acid, ethyl ester for the
2.4- dicnloropyridin-5-carboxylic acid, ethyl ester in the procedure of Example 1, 2,4-dichloro-6-methyl5- [ [1- (2,4-dichlorophenyl) -2- (IH-imidazol-l-yl) ethoxylmethyl]pyridine and its hydrochloride, m.p.
225-260° are obtained, nitrate m.p. 121-122°.
The following additional products of formula C are obtained by the procedure of Exainple 1 by reacting the unsubstituted or substituted l-phenyl-2-(lH-imidazol-l-yl)ethanol of formula A with the unsubstituted or substituted 5-chloromethylpyridine of formula B.
The substituents apply to the respective formulas.
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Example
IS
Example 44
4,6-Dichloro-3-{[1-(2,4-dichlorophenyl)-2-(IH-imidazoll-yl)ethoxy]methyllquinoline, hydrochloride (1:1)
a) 4,6-Dichloroquinoline-3-carboxylic acid, ethyl ester
A mixture of 45.2 g. of 6-chloro-4-hydroxyquinoline-3-carboxylic acid, ethyl ester (0.18 mol.) and 250 ml. of thionyl chloride is refluxed for 20 hours. The excess thionyl chloride is then removed in vacuo, the residue treated with 200 ml. of water and the ester is extracted with ether. After washing the ethereal extract twice with water, it is dried with Na_SO and the solvent distilled off. The 2 4 residual 4,6-dichloroquinoline-3-carboxylic acid, ethyl ester is triturated with petroleum ether (40-60°), filtered and dried. Yield: 45.3 g. (93%); m.p. 87-88°.
b) 4,6-Dichloroquinoline-3-methanol
g. of 4,6-dichloroquinoline-5-carboxylic aaid, ethyl ester (0.1 mol.) are dissolved in 600 ml.
48081 of anhydrous tetrahydrofuran. Nitrogen is passed through the flask and while stirring and cooling to
Q
Q , 2.4 g. of lithium aluminum hydride are added a bit at a time in order to keep the reaction temperao ...
ture at 0 to +5 . Stirring is continued for an additional five hours. Then 2.5 ml. of water,
2.0 ml. of aqueous sodium hydroxide (20%) and again 9 ml. of water are added. The precipitated inorganic salts are filtered off and the solvent is removed by a rotary evaporator. The resulting oil is dissolved in a small quantity of benzene and kept in the refrigerator. The crystallized 4,6-dichloroquinoline-3methanol is filtered off and reerystallized from ethyl acetate; yield: 12.5 g. (55%); m.p 182°.
c) 3-Chloromethy1-4,6-dichloroquinoline
11.4 g. of 4,6-dichloroquinoline-3-methanol (0.05 mol.) are added in portions to 150 ml. of thionyl chloride. The reaction mixture is allowed to stand for 24 hours at room temperature. Then the solution is filtered and the excess thionyl chloride removed by a rotary evaporator. The residue is triturated with water, filtered off, washed again with water and dried in a desiccator over P2°5 t0 obtain 3-chloromethyl-4,6-dichloroquinoline; yield: 11.5 g. (93.5%); m.p. 102-105°.
Recrystallization from cyclohexane does not change the melting point.
d) 4,6-Dichloro-3-((1-(2,4-dichlorophenyl)-2(1H- imidazol-l-yl) ethoxy] methyl I quinoline , hydrochloride (1:1)
In a three necked flask, fitted with stirrer, reflux condenser and gas inlet tube are introduced
14.8 g. of sodium hydroxide (0.37 mol.) and 25 ml. of water. While passing nitrogen through the flask, the solution is cooled to 45° and then are added 3.85 g. of 1-(2,4-dichlorophenyl)-2-(lH-imidazol-15 yl)ethanol (0.015 mol.), [prepared according to
J. Med. Chem., Vol. 12, 784 (1969)], 0.25 g. of benzyltrimethylammonium chloride and 25 ml. of tetrahydrofuran. To the mixture, which is warmed to 50°, a solution of 3.6 g. of 3-chloromethyΙΙΟ 4,6-dichloroquinoline (0.015 mol.) in 10 ml. of tetrahydrofuran is added from a prewarmed dropping funnel within 3 giinutes. The mixture is stirred vigorously for 3 hours at 60° using a water bath. Then the warm mixture is
U transferred into a separating funnel, the lower aqueous sodium hydroxide is extracted with 10 ml. of tetrahydrofuran. The combined tetrahydrofuran layers are dried by means of sodium sulfate, and after the solvent has been removed, the residual oil is
2Q extracted with ether, treated with charcoal and filtered. To the solution of free base are added dropwise ethereal hydrochloric acid. The precipitated 4,6-dichloro-3-[[1-(2,4-dichlorophenyl-2(1H-imidazol-l-yl)ethoxy]methyl]quinoline, hydro,5 chloride is filtered off, dried in the vacuum desiccator and recrystallized from absolute ethanol; yield: 1.9 g. (25%); m.p. 148-150°.
Example 45
4,7-Dichloro-3-[[1-(2,4-dichlorophenyl)-2-(lH-imidazolθ 1-yl)ethoxy]methyl]quinoline, hydrochloride (1:2)
a) 4,7-Dichloroquinoline-3-carboxylic acid, ethyl ester
A mixture of 30 g. of 7-chloro-4-hydroxy48081 quinoline-3-carboxylic acid, ethyl ester, m.p. 299-301°, (0.12 mol.) and 250 ml. of phosphorus oxychloride is refluxed for 4.5 hours. After removing the excess phosphorus oxychloride, the residue is triturated with water and dissolved in ether. The ethereal solution is washed with aqueous sodium carbonate (5%) and water, dried with sodium sulfate and the solvent is removed. The residual 4,7-dichloroquinoline3-carboxylic acid, ethyl ester is triturated with petroleum ether (40-60°), filtered off and dried; yield: 22 g. (68%); m.p. 81-82°.
b) 4,7-Dichloroquinoline-3-methanol
Following the procedure of Example lb, 21 g. of 4,7-dichloroquinoline-3-carboxylic acid, ethyl ester (0.08 mol.) in 500 ml. of anhydrous tetrahydrofuran and 1.9 g. of lithium aluminum hydride yield 8.4 g. (46%) of 4,7-dichloroquinoline-3-methanol; m.p. 144-145° (ethyl acetate).
c) 3-Chloromethy1-4,7-dichloroquinoline
g. of 4,7-dichloroquinoline-3-methanol (0.035 mol.) and 100 ml. of thionyl chloride are reacted according to the procedure of Example lc to obtain 7.1 g. (82.5%) of 3-chloromethyl-4,7o dichloroquinoline; m.p. 106-107 .
d) 4,7-Dichloro-3-[[1-(2,4-dichlorophenyl)-2(1H-imidazol-l-yl)ethoxylmethyl3 quinoline, hydrochloride (1:2)
.2 g. of 1-(2,4-dichlorophenyl)-2-(1Himidazol-l-yl)ethanol (0.02 mol.) dissolved in 45 ml. of anhydrous tetrahydrofuran and 0.8 g. of sodium hydride (55-60% dispersion in mineral oil) are stirred for 4.5 hours at room temperature. After the sodium salt formation is complete, 4.9 g. of 3chloromethyl-4,7-dichloroquinoline (0.02 mol.) dissolved in 25 ml. of anhydrous tetrahydrofuran are added and the mixture is stirred at 50-60° (bath temperature) for 4 hours. Then tetrahydrofuran is removed, the residue treated with water and extracted with ether. The ethereal layer is washed with water and dried with sodium sulfate. Addition of ethereal hydrochloric acid to the ether solution of the base precipitates the hydrochloride salt. For purification the hydrochloride is converted into the free base and again extracted and treated with ethereal hydrochloric acid. Recrystallization from ethyl acetate gives 2.1 g. (20%) of 4,7-dichloro-3-[[1-(2,4-dichlorophenyl) -2- (ΙΗ-imidazol-l-yl)ethoxy]methyl]quinoline, hydrochloride (1:2); m.p. 148-149°.
The following additional products of formula 5 are obtained by the procedure of Example 44 by reacting the unsubstituted or substituted 1-phenyl2-(IH-imidazol-l-yl)ethanol of formula B with the unsubstituted or substituted 3-chloromethylquinoline of formula F. The substituents apply to the respective formulas.
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Claims (25)
1. A compound of the fonnula : lower alkoxy, lower alkylthio, hydroxy or halogen; and acid addition salts thereof.
2. A compound of formula I as in Claim 1 2 4 wherein R and R each is halogen. 10
3. A compound of formula I as in Claim 1 wherein R 5 and each, is halogen.
4. A compound as in Claim 2 wherein each halogen is chlorine.
5. A compound as in Claim 3 wherein each i5 halogen is chlorine.
6. A compound of fonnula I as in Claim 1 wherein R^ to R^ each is hydrogen, lower alkyl of 1 to 4 carbons or halogen.
7. A compound of formula I as in Claim 1 13 2 4 wherein R and R each is hydrogen; R and R each e g is halogen; R 3 is 2-halo; and R is 4-halo; and physiologically acceptable acid addition salts 5 thereof.
8. A compound of formula I as in Claim 1 13 2 4 wherein R and R each is hydrogen; R and R each is chloro; K? is 2-chloro and R® is 4-chloro.
9. A compound of formula I as in Claim 1 1 2 4 3 10. Wherein R is methyl; R and R ate chloro; R is hydrogen; R 5 is 2-chloro; R^ is 4-chloro; and acid addition salts thereof.
10. The hydrochloride acid addition salt of the compound of Claim 8. 15
11. A compound of formula II as in Claim 1 wherein R® is halo.
12. A compound of formula II as in Claim 1 g wherein R is halo.
13. A compound of formula II as in Claim 1 5 5 10 wherein R and R each is halo.
14. A compound as in Claim 13 wherein each halo is chloro.
15. A compound of formula II as in Claim 1 5 6 wherein R is 2-chloro and R is 4-chloro. 25
16. A compound of formula II as in Claim 1 wherein R^ to each is hydrogen, halogen or C^C^-lower alkyl.
17. A compound of formula II as in Claim 1 wherein R^ to β^θ each is hydrogen or halogen. 30
18. A compound of formula II as in Claim 1 wherein R^, R^ and R^ each is hydrogen; and R 2 , 5 6 R and R each is halogen; and acid addition salts thereof.
19. A compound of formula IX as in Claim 1 178 10 2 wherein R , R , R and R each is hydrogen; R 9 5 6 . and R each is chloro; R is 2-chloro; and R is 4-chloro. E>
20. A compound of formula II as in Claim 1 wherein R 1 , R 7 , R 9 and each is hydrogen; R 2 and 8 5 6 R each is chloro; R is 2-chloro; and R is 4-chloro.
21. A compound of the formula wherein R 1 to R^ each is hydrogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxy or halogen; and acid addition salts thereof. is
22. A compound of the formula R wherein R^, R 2 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 each is hydrogen, hydroxy, halogen, lower alkyl, lower alkoxy or lower alkylthio; and acid addition salts thereof.
23. A process for preparing a compound of fonnula I or II, substantially as herein described with reference to any of the Examples.
24. A ccmfjouTiJ ^i?i τηαίο. TetTT xiLen oLltu-ned Lij 5 a process according to claim 23.
25. A pharmaceutical composition comprising a compound according to any of claims 1 to 22 and 24, together with an excipient, vehicle or binder.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/954,730 US4191831A (en) | 1978-10-25 | 1978-10-25 | Imidazolylethoxy derivatives of pyridin-5-methanols |
| US05/954,728 US4202985A (en) | 1978-10-25 | 1978-10-25 | Imidazolylethoxy derivatives of quinoline-3-methanols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE791894L IE791894L (en) | 1980-04-25 |
| IE49081B1 true IE49081B1 (en) | 1985-07-24 |
Family
ID=27130354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1894/79A IE49081B1 (en) | 1978-10-25 | 1979-10-05 | Imidazolylethoxy derivatives of pyridine-5-methanols and quinoline-3-methanols |
Country Status (12)
| Country | Link |
|---|---|
| AU (1) | AU5136879A (en) |
| DE (1) | DE2943151A1 (en) |
| DK (1) | DK448379A (en) |
| FR (1) | FR2439781A1 (en) |
| GB (1) | GB2033384B (en) |
| HU (1) | HU178748B (en) |
| IE (1) | IE49081B1 (en) |
| IT (1) | IT1125592B (en) |
| LU (1) | LU81814A1 (en) |
| NL (1) | NL7907349A (en) |
| NO (1) | NO793411L (en) |
| SE (1) | SE7908820L (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282230A (en) * | 1979-11-15 | 1981-08-04 | E. R. Squibb & Sons, Inc. | Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them |
-
1979
- 1979-09-28 FR FR7924279A patent/FR2439781A1/en not_active Withdrawn
- 1979-10-02 AU AU51368/79A patent/AU5136879A/en not_active Abandoned
- 1979-10-03 NL NL7907349A patent/NL7907349A/en not_active Application Discontinuation
- 1979-10-04 GB GB7934486A patent/GB2033384B/en not_active Expired
- 1979-10-05 IE IE1894/79A patent/IE49081B1/en unknown
- 1979-10-24 IT IT26765/79A patent/IT1125592B/en active
- 1979-10-24 NO NO793411A patent/NO793411L/en unknown
- 1979-10-24 LU LU81814A patent/LU81814A1/en unknown
- 1979-10-24 DK DK448379A patent/DK448379A/en unknown
- 1979-10-24 HU HU79SU1038A patent/HU178748B/en unknown
- 1979-10-24 SE SE7908820A patent/SE7908820L/en not_active Application Discontinuation
- 1979-10-25 DE DE19792943151 patent/DE2943151A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2943151A1 (en) | 1980-05-08 |
| HU178748B (en) | 1982-06-28 |
| GB2033384B (en) | 1982-08-25 |
| NL7907349A (en) | 1980-04-29 |
| IE791894L (en) | 1980-04-25 |
| GB2033384A (en) | 1980-05-21 |
| IT1125592B (en) | 1986-05-14 |
| NO793411L (en) | 1980-04-28 |
| AU5136879A (en) | 1980-05-01 |
| DK448379A (en) | 1980-04-26 |
| FR2439781A1 (en) | 1980-05-23 |
| IT7926765A0 (en) | 1979-10-24 |
| SE7908820L (en) | 1980-04-26 |
| LU81814A1 (en) | 1980-01-25 |
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