DE2009134A1 - Neue Triazol-Derivate und Verfahren zur Herstellung derselben - Google Patents
Neue Triazol-Derivate und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2009134A1 DE2009134A1 DE19702009134 DE2009134A DE2009134A1 DE 2009134 A1 DE2009134 A1 DE 2009134A1 DE 19702009134 DE19702009134 DE 19702009134 DE 2009134 A DE2009134 A DE 2009134A DE 2009134 A1 DE2009134 A1 DE 2009134A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- ethyl ester
- acid ethyl
- formula
- triazole
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- -1 5-m-Fluoroanilino-triazole-4-carboxylic acid ethyl ester Chemical compound 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000006088 Dimroth rearrangement reaction Methods 0.000 claims description 4
- ZOQWWKJOMSKGRQ-UHFFFAOYSA-N ethyl 5-amino-1-(3-chlorophenyl)triazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)N=NN1C1=CC=CC(Cl)=C1 ZOQWWKJOMSKGRQ-UHFFFAOYSA-N 0.000 claims description 4
- DCJZBLIDDBPKKI-UHFFFAOYSA-N ethyl 5-amino-1-(4-chlorophenyl)triazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)N=NN1C1=CC=C(Cl)C=C1 DCJZBLIDDBPKKI-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 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
- CPAJFCHMLPNQDF-UHFFFAOYSA-N ethyl 5-(3-chloroanilino)-2h-triazole-4-carboxylate Chemical compound CCOC(=O)C1=NNN=C1NC1=CC=CC(Cl)=C1 CPAJFCHMLPNQDF-UHFFFAOYSA-N 0.000 claims description 3
- MEYGIEGWBVQWMK-UHFFFAOYSA-N ethyl 5-(4-chloroanilino)-2h-triazole-4-carboxylate Chemical compound N1N=NC(NC=2C=CC(Cl)=CC=2)=C1C(=O)OCC MEYGIEGWBVQWMK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 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
- 230000000507 anthelmentic effect Effects 0.000 description 4
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 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 3
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NTTKOAYXVOKLEH-UHFFFAOYSA-N 1-azido-3-chlorobenzene Chemical compound ClC1=CC=CC(N=[N+]=[N-])=C1 NTTKOAYXVOKLEH-UHFFFAOYSA-N 0.000 description 1
- MQFLRDDKIIPOFC-UHFFFAOYSA-N 1-azido-3-fluorobenzene Chemical compound FC1=CC=CC(N=[N+]=[N-])=C1 MQFLRDDKIIPOFC-UHFFFAOYSA-N 0.000 description 1
- HZVGOEUGZJFTNN-UHFFFAOYSA-N 1-azido-4-chlorobenzene Chemical compound ClC1=CC=C(N=[N+]=[N-])C=C1 HZVGOEUGZJFTNN-UHFFFAOYSA-N 0.000 description 1
- VHFLTICYUZLEII-UHFFFAOYSA-N 1-azido-4-fluorobenzene Chemical compound FC1=CC=C(N=[N+]=[N-])C=C1 VHFLTICYUZLEII-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000235646 Cyberlindnera jadinii Species 0.000 description 1
- 241000243676 Enchytraeus albidus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000243653 Tubifex Species 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000000338 in vitro Methods 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000000080 wetting agent Substances 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001628 | 1969-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2009134A1 true DE2009134A1 (de) | 1970-09-10 |
Family
ID=10995291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702009134 Pending DE2009134A1 (de) | 1969-02-26 | 1970-02-26 | Neue Triazol-Derivate und Verfahren zur Herstellung derselben |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT296295B (enrdf_load_stackoverflow) |
| DE (1) | DE2009134A1 (enrdf_load_stackoverflow) |
| DK (1) | DK128497B (enrdf_load_stackoverflow) |
| FR (1) | FR2034567B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1296911A (enrdf_load_stackoverflow) |
| IL (1) | IL33942A (enrdf_load_stackoverflow) |
| NL (1) | NL143928B (enrdf_load_stackoverflow) |
| SE (1) | SE359547B (enrdf_load_stackoverflow) |
| YU (1) | YU33275B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9073875B2 (en) | 2012-11-20 | 2015-07-07 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3134842A1 (de) * | 1981-09-03 | 1983-03-17 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue anilino-1,2,3-triazol-derivate, diese enthaltende arzneimittel sowie verfahren zu deren herstellung und deren verwendung |
-
1970
- 1970-02-19 GB GB1296911D patent/GB1296911A/en not_active Expired
- 1970-02-20 DK DK86270AA patent/DK128497B/da unknown
- 1970-02-23 IL IL33942A patent/IL33942A/en unknown
- 1970-02-24 AT AT170070A patent/AT296295B/de not_active IP Right Cessation
- 1970-02-24 YU YU455/70A patent/YU33275B/xx unknown
- 1970-02-24 NL NL707002572A patent/NL143928B/xx unknown
- 1970-02-25 SE SE02456/70A patent/SE359547B/xx unknown
- 1970-02-26 DE DE19702009134 patent/DE2009134A1/de active Pending
- 1970-02-26 FR FR7006922A patent/FR2034567B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9073875B2 (en) | 2012-11-20 | 2015-07-07 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase |
| US9499497B2 (en) | 2012-11-20 | 2016-11-22 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase |
Also Published As
| Publication number | Publication date |
|---|---|
| IL33942A (en) | 1973-07-30 |
| AT296295B (de) | 1972-02-10 |
| YU33275B (en) | 1976-08-31 |
| YU45570A (en) | 1976-03-31 |
| NL7002572A (enrdf_load_stackoverflow) | 1970-08-28 |
| FR2034567A1 (enrdf_load_stackoverflow) | 1970-12-11 |
| NL143928B (nl) | 1974-11-15 |
| DK128497B (da) | 1974-05-13 |
| SE359547B (enrdf_load_stackoverflow) | 1973-09-03 |
| IL33942A0 (en) | 1970-04-20 |
| FR2034567B1 (enrdf_load_stackoverflow) | 1974-07-12 |
| GB1296911A (enrdf_load_stackoverflow) | 1972-11-22 |
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