IL33942A - 1-phenyl-5-amino-1,2,3-triazole-4-carboxylic acid esters,their preparation and pharmaceutical compositions containing them - Google Patents
1-phenyl-5-amino-1,2,3-triazole-4-carboxylic acid esters,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL33942A IL33942A IL33942A IL3394270A IL33942A IL 33942 A IL33942 A IL 33942A IL 33942 A IL33942 A IL 33942A IL 3394270 A IL3394270 A IL 3394270A IL 33942 A IL33942 A IL 33942A
- Authority
- IL
- Israel
- Prior art keywords
- acid ethyl
- ethyl ester
- carboxylic acid
- formula
- triazole
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- RXJQVZQJLCDQOH-UHFFFAOYSA-N 5-amino-1-phenyltriazole-4-carboxylic acid Chemical class NC1=C(C(O)=O)N=NN1C1=CC=CC=C1 RXJQVZQJLCDQOH-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000004494 ethyl ester group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 238000006088 Dimroth rearrangement reaction Methods 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000006187 pill Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- IWYTVJRNVRDBMC-UHFFFAOYSA-N CCOC(C1=NN=NC1(C1=CC(F)=CC=C1)N)=O Chemical compound CCOC(C1=NN=NC1(C1=CC(F)=CC=C1)N)=O IWYTVJRNVRDBMC-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- BTHZSTZVTDQFAB-UHFFFAOYSA-N ethyl 5-amino-1-(4-fluorophenyl)triazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)N=NN1C1=CC=C(F)C=C1 BTHZSTZVTDQFAB-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000013078 crystal Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 230000000507 anthelmentic effect Effects 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- -1 metafluorophenyl azide Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000243653 Tubifex Species 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
acid their preparation pharmaceutical eontainiag them This invention relates to new triazole The invention also relates to a process for preparing compounds of this According to a feature of the present invention there are provided new triazole derivatives having the general formula I wherein A stands for an containing from 1 to 5 carbon and the one from the 1 and R2 stands for hydrogen atom and the other stands for a group having the general formula II fluorine wherein X is a chlorine or atom in or Compounds of similar but wherein 2 always stands for a hydrogen atom and X stands for a hydrogen a or group are known from the literature 2001 These known compounds an antipyretic effect and the derivative has a bacteriostatic effect Suitable representatives of the compounds of formula I are the following derivatives lic acid ethyl lic acid ethyl oxylic acid ethyl acid ethyl lic acid ethyl acid ethyl acid ethyl acid ethyl The new compounds according to the invention can be conveniently prepared by reacting a acid ester of the formula III C COOALk has the same meanings as with a azide of formula wherein has the same meanings as and if the is a acid alkyl in which stands for a hydrogen if this ester is subjected to a rearrangement 183 44 The Dimroth rearrangement is preferably carried out in pyridine5 while The new compounds of formula I possess valuable pharmacological They have an effect which is especially strong in the case of Bnchytraeus albidus and Tubifex The anthelmintic effect of some compounds according to the invention is shown in Table The vermicidal activity was investigated with method in Table 1 Designation of the Minimum concentration for Z 24 acid ethyl este acid ethyl ester acid ester lic acid ethyl lic acid ethyl ester HC1 acil chloride for comparison purposes and having excellent anthelmintic The compounds 2 to 5 show a good anthelmintic effect also in connection with Candida According to a further feature of the present invention there are provided pharmaceutical compositions comprising as active ingredient at least one compound of formula in admixture with suitable pharmaceutical carriers These pharmaceutical compositions can be coated or such as or jectable The compositions can be suitable for rectal or parenteral The carriers can be conventional organic or inorganic such as magnesium polyalkylene magnesium carbonate The pharmaceutical compositions may contain such as disintegrating and watting agents The preparation may comprise in addition to the compound of formula I further therapeutically active compounds as The pharmaceutical compositions of the present invention be prepared by usual methods known per se of the industry by admixing the active ingredient with suitable solid or liquid organic or inorganic tical carriers excipients if wit other therapeutically active The daily dose of the compounds according to the vention for adults amounts from 60 to 400 The invention is further illustrated by the aid of the following which are given for the purpose of illustration only and are not to be construed as limiting the Example 1 g of metafluorophenyl azide and of cyanacetic acid ethyl ester are dissolved in 90 ml of absolute ethanol and in a provided a mixer and a tube containing calcium chloride against the moisture content of a sodium ethylate solution pared from of sodium and 90 of ethanol is dropped to while keeping the temperature below 10 by the aid of outer After finishing the the cooling is ceased and the mixture is stirred for a further hour at room Thereafter the mixture is poured into 1500 of icy The crystals precipitated are washed with water and In this way of acid ethyl ester are obtained with a melting point of After recrys from 220 of colourless crystals weighing 11 are obtained with a melting point of Example 2 8 of acid ethyl ester are dissolved in 24 of pyridine and the solution is boiled under reflux 3 whereafter it is poured into 300 of icy filtered The white crystalline precipitate is washed with cold water and In this way 7 of acid ethyl ester are obtained with a melting point of After crystallizing from acetic 75 of product are obtained a melting point of 139 to 141 Analysis data for 9 ST F ΕΓ Example 3 of acid and of cyanacetic acid ethyl eater are dissolved in 100 ml of absolute and in a flask provided with a mixer and a tube containing calcium chloride against the moisture content of the a sodium ethylate solution pared from of sodium and 50 of added absolute ethanol are to while keeping the temperature external 0 with cooling below 10 After finishing the addition the cooling is ceased and the mixture 13 stirred for a further hour at room then it is poured into filtered 15OO of The crystals precipitated are washed with water and In this way of acid ethyl ester are obtained with a meltin point of to 137 After recrystallizing from 500 of 62 of crystals needles are obtained with a melting poin of 139 Analysis data for P 59 P 7 Example 4 of acid ethyl ester are dissolved in 24 of absolute The solution is boiled for 8 hours under reflux and then poured into 300 of icy The filtered crystalline precipitate formed is washed witk cold water and In this way of lic acid ester are obtained with a melting point of After recrystallizing from of acetic of product are obtained with a melting point of 141 Analysis data for t P N P Example 5 of azide and of cyanacetic acid ethyl ester are dissolved in 100 of absolute and in a provided with a stirrer and a tube containing calcium chloride against the moisture content of the air a sodium ethylate solution prepared from of sodium and ml of ethanol is dropped to while the temperature o below 10 C with outer After the addition is the cooling is the mixture is stirred for further 2 hours at room temperature and then it is poured into 1500 of icy The crystals precipitated filtered are washed with water and In this way of acid ethyl ester are obtained with a melting point of 1fter recrystallizing from 400 of of colourless crystal needles are obtained with a melting point of Analysis data for Cl N ti t Cl Example 6 o of acid ethyl ester are dissolved in 21 of absolute The solution is boiled for 3 hours under reflux and then it is poured into of icy The white filtered crystals obtained are washed with cold water and In this way acid ethyl ester are obtained with a melting point of 15 After recrystallizing from 2 0 of 50 acetic of product is obtained with a melting point of Analysis data for N Example of azide and of cyanacetic acid ethyl ester are dissolved in 100 of absolute and in a flask provided a stirrer and a tube filled with calcium chloride against the moisture of a sodium ethylate solution pared from of sodium and of ethanol is dropped to while keeping the temperature outer cooling below 10 After finishing the addition and ceasing the the mixture is stirred for a further hour at room temperature and then it is poured into filtered 1500 of The crystals precipitated are washed with cold water and In this way of acid ethyl ester are obtained with a melting point of After recrystallizing from of o of colourless crystals are Analysis data for fo 01 Example of acid ethyl ester are dissolved in 24 ml of absolute The solution is boiled under reflux for 8 hours and then it is poured into 300 of icy filtered The white crystals separated are sucked washed with cold water In this way fo of acid ethyl ester are obtained with a melting point of After from of 50 acetic fo of product are obtained with a melting point of 162 Analysis data for fo 01 N insufficientOCRQuality
Claims (12)
1. ETe¾r compound of the general formula I wherein Alk stands for an alkyl group containing from 1 to 5 carbon atoms, and the one from the substituents R 2 and ¾ stands for hydrogen atom and the other stands for a group having the general formula II fluorine wherein X is a chlorine or bromine atom, in m- or p-position,
2. A compound selected from the group consisting of 5-m-fluorophenyl-5-aminotriazole-4-carboxylic acid ethyl ester, 5-m-fluo*^nilino~triazole-4-carboxylic acid ethyl ester, 1-p-fluorophenyl-5-aminotriazole-4-carboxylic acid ethyl ester, 5~P~fluor^.nilino-triazole-4-carboxylie acid ethyl ester, l- -chlo^phenyl-5-aminotriazole—4-carbox lie acid ethyl ester, ^m-chlar/^nilino—triazole~4-carboxylic acid ethyl ester, l-p-chlorophenyl-5~aminotriazole-4- -carboxylic acid ethyl ester and 5_P~chlo^anilino-triazole- -4-carboxylic acid ethyl ester.
3. A process for preparing the new compounds of formula I B½H COO-illk wherein Alk stands for an alkyl-group containing from 1 to 5 carbon atoms, and the one from the substituents Ή1 and H' stands for hydrogen atom and the other stands for a group having the general formula II fluorine wherein X is a chlorine or/bromfpnrc atom in m- or p-position comprising the steps of reacting a cyanacetic acid alkyl ester of formula III ΓΓ - CH2 - GOOAlk (ill) wherein Alk has the same meanings as above, with a halophen azide of formula IV wherein X has the same meanings as above, and if the product is a halophenyl™5~amino-l , »3-triazole-4-carboxylic acid alkyl ester, in which E1 is a hydrogen atom, then, if desired, subjecting this ester to a Dimroth rearrangement. *
4. » A process as claimed in claim 3, in which the reaction between the compounds of formulas ΓΙΧ and IV is carried out in an alcoholic medium at a temperature between -10°C and +40 °C.
5. 5. A process as claimed in claim 3, in which the Dimroth rearrangement is carried out while boiling in a medium containing pyridine.
6. A process as claimed in claim 3» substantially as herein described, with reference to the Examples. ιο
7. Compounds as claimed in claim 1, whenever prepared by a process as claimed in any of claims 3 to 6.
8. Pharmaceutical compositions comprising as active ingredient at least one compound of formula I, in admixture with suitable solid or liquid pharmaceutical carriers and/or 15 excipients .
9. Pharmaceu ical compositions as claimed in claim 8 , in the form of tablets, pills, coated pills, suppositories, capsules, solutions, emulsions, suspensions or injectable preparations. 20
10. Pharmaceutical compositions as claimed in claim 8 or 9, comprising in addition to the compound of formula I at least one further therapeutically active compound.
11. A process for preparing pharmaceutical compositions as claimed in any of claims 8 to 10, comprising admixing one or more compound of formula I and optionally therapeutically active compounds with suitable solid or liquid organic or inorganic pharmaceutical carriers and/or excipients. a
12. Pharmaceutical compositions whenever prepared by y process as claimed in claim 11. nts
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001628 | 1969-02-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33942A0 IL33942A0 (en) | 1970-04-20 |
| IL33942A true IL33942A (en) | 1973-07-30 |
Family
ID=10995291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33942A IL33942A (en) | 1969-02-26 | 1970-02-23 | 1-phenyl-5-amino-1,2,3-triazole-4-carboxylic acid esters,their preparation and pharmaceutical compositions containing them |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT296295B (en) |
| DE (1) | DE2009134A1 (en) |
| DK (1) | DK128497B (en) |
| FR (1) | FR2034567B1 (en) |
| GB (1) | GB1296911A (en) |
| IL (1) | IL33942A (en) |
| NL (1) | NL143928B (en) |
| SE (1) | SE359547B (en) |
| YU (1) | YU33275B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3134842A1 (en) * | 1981-09-03 | 1983-03-17 | Boehringer Ingelheim KG, 6507 Ingelheim | NEW ANILINO-1,2,3-TRIAZOLE DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THEM AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| KR20150087400A (en) | 2012-11-20 | 2015-07-29 | 버텍스 파마슈티칼스 인코포레이티드 | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase |
-
1970
- 1970-02-19 GB GB1296911D patent/GB1296911A/en not_active Expired
- 1970-02-20 DK DK86270AA patent/DK128497B/en unknown
- 1970-02-23 IL IL33942A patent/IL33942A/en unknown
- 1970-02-24 YU YU455/70A patent/YU33275B/en unknown
- 1970-02-24 AT AT170070A patent/AT296295B/en not_active IP Right Cessation
- 1970-02-24 NL NL707002572A patent/NL143928B/en unknown
- 1970-02-25 SE SE02456/70A patent/SE359547B/xx unknown
- 1970-02-26 FR FR7006922A patent/FR2034567B1/fr not_active Expired
- 1970-02-26 DE DE19702009134 patent/DE2009134A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1296911A (en) | 1972-11-22 |
| FR2034567A1 (en) | 1970-12-11 |
| IL33942A0 (en) | 1970-04-20 |
| FR2034567B1 (en) | 1974-07-12 |
| DK128497B (en) | 1974-05-13 |
| SE359547B (en) | 1973-09-03 |
| AT296295B (en) | 1972-02-10 |
| NL7002572A (en) | 1970-08-28 |
| YU45570A (en) | 1976-03-31 |
| DE2009134A1 (en) | 1970-09-10 |
| YU33275B (en) | 1976-08-31 |
| NL143928B (en) | 1974-11-15 |
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