HRP20171321T1 - Postupak za pripremanje spojeva triazola - Google Patents
Postupak za pripremanje spojeva triazola Download PDFInfo
- Publication number
- HRP20171321T1 HRP20171321T1 HRP20171321TT HRP20171321T HRP20171321T1 HR P20171321 T1 HRP20171321 T1 HR P20171321T1 HR P20171321T T HRP20171321T T HR P20171321TT HR P20171321 T HRP20171321 T HR P20171321T HR P20171321 T1 HRP20171321 T1 HR P20171321T1
- Authority
- HR
- Croatia
- Prior art keywords
- triazol
- acetate
- ethyl
- methyl
- dimethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 11
- -1 triazole compounds Chemical class 0.000 title claims 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- CHXQIZCRAILOKT-UHFFFAOYSA-N (2-ethyl-1H-triazol-3-yl) acetate Chemical compound C(C)(=O)ON1N(NC=C1)CC CHXQIZCRAILOKT-UHFFFAOYSA-N 0.000 claims 5
- KEVLWCQZLZYRGR-UHFFFAOYSA-N (4-ethyltriazol-1-yl) acetate Chemical compound C(C)(=O)ON1N=NC(=C1)CC KEVLWCQZLZYRGR-UHFFFAOYSA-N 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- JIYBABOHFPTKOU-UHFFFAOYSA-N (2-methyl-1H-triazol-3-yl) acetate Chemical compound C(C)(=O)ON1N(NC=C1)C JIYBABOHFPTKOU-UHFFFAOYSA-N 0.000 claims 4
- XWDNLTCJJYYYCI-UHFFFAOYSA-N (6-morpholin-4-ylpyrimidin-4-yl)hydrazine Chemical compound C1=NC(NN)=CC(N2CCOCC2)=N1 XWDNLTCJJYYYCI-UHFFFAOYSA-N 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 2
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 claims 2
- 229930194542 Keto Natural products 0.000 claims 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 2
- NTIRTFLRBFAPSX-UHFFFAOYSA-N OC1=C(N2N=NC=C2)C=NN1C(N=CN=1)=CC=1N1CCOCC1 Chemical compound OC1=C(N2N=NC=C2)C=NN1C(N=CN=1)=CC=1N1CCOCC1 NTIRTFLRBFAPSX-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- NYXYZCSAJZLFEH-UHFFFAOYSA-N (6-chloropyrimidin-4-yl)hydrazine Chemical compound NNC1=CC(Cl)=NC=N1 NYXYZCSAJZLFEH-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 claims 1
- IJMBOKOTALXLKS-UHFFFAOYSA-N 2-(6-morpholin-4-ylpyrimidin-4-yl)-4-(triazol-1-yl)-1h-pyrazol-3-one Chemical compound O=C1C(N2N=NC=C2)=CNN1C(N=CN=1)=CC=1N1CCOCC1 IJMBOKOTALXLKS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 claims 1
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- VYRQLKYGGSWDNH-UHFFFAOYSA-M sodium;2-(6-morpholin-4-ylpyrimidin-4-yl)-4-(triazol-1-yl)pyrazol-3-olate Chemical compound [Na+].[O-]C1=C(N2N=NC=C2)C=NN1C(N=CN=1)=CC=1N1CCOCC1 VYRQLKYGGSWDNH-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (10)
1. Postupak za pripremanje 1-[6-(morfolin-4-il)pirimidin-4-il]-4-(1H-1,2,3-triazol-1-il)-1H-pirazol-5-ola (I - enol oblik) ili 2-[6-(morfolin-4-il)pirimidin-4-il]-4-(1H-1,2,3-triazol-1-il)-1,2-dihidro-3H-pirazol-3-ona (I - keto oblik), naznačen time da
a) u prvom koraku, 1,2,3-triazol (III) reagira s metil bromoacetatom (IV-Me-Br) ili etil bromoacetatom (IV-Et-Br) u prisutnosti etildiizopropilamina kao baze u otapalu u temperaturnom rasponu od 20 do 80°C da nastanu spojevi metil-1H-1,2,3-triazol-1-il acetat (V-Me) i metil-2H-1,2,3-triazol-1-il acetat (VI-Me) ili spojevi etil-1H-1,2,3-traizol-1-il acetat (V-Et) i etil-2H-1,2,3-triazol-1-il acetat (VI-Et),
b) u drugom koraku, spojevi metil-1H-1,2,3-triazol-1-il acetat (V-Me) i metil-2H-1,2,3-triazol-1-il acetat (VI-Me) ili spojevi etil-1H-1,2,3-traizol-1-il acetat (V-Et) i etil-2H-1,2,3-triazol-1-il acetat (VI-Et), koji su prisutni u međusobnom omjeru od barem 6:1, reagiraju s dimetilformamid dimetil acetalom (XIX-Me) ili dimetilformamid dietil acetalom (XIX-Et) u inertnom otapalu i zatim kristaliziraju hlađenjem otopine ili pomoću destilacije otapala i dodavanjem drugog otapala da nastane metil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Me) ili etil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Et),
i
c) u trećem koraku, metil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Me) ili etil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Et) reagira s 4-(6-hidrazinopirimidin-4-il)morfolinom (XI) u prisutnosti trifluoroctene kiseline u inertnom otapalu i zatim se izolira spoj s formulom (I).
2. Postupak prema zahtjevu 1, naznačen time da, u svrhu dobivanja 1-[6-(morfolin-4-il)pirimidin-4-il]-4-(1H-1,2,3-triazol-1-il)-1H-pirazol-5-ola (I - enol oblik) ili 2-[6-(morfolin-4-il)pirimidin-4-il]-4-(1H-1,2,3-triazol-1-il)-1,2-dihidro-3H-pirazol-3-ona (I - keto oblik), metil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Me) ili etil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Et) reagira s 4-(6-hidrazinopirimidin-4-il)morfolinom (XI) u prisutnosti trifluoroctene kiseline u inertnom otapalu uz naknadno dodavanje trietilamina, te se zatim izolira spoj s formulom (I).
3. Postupak prema zahtjevu 2, naznačen time da se nakon dodavanja trietilamina reakcijska smjesa održava na temperaturi od 20 do 90°C.
4. Postupak prema bilo kojem od zahtjeva 1 do 3, naznačen time da se pročišćavanje nastalog sirovog produkta spoja s formulom (I) provodi korištenjem vode i kiseline uz pH od 4 do 5.5.
5. Postupak prema bilo kojem od zahtjeva 1 do 4, naznačen time da na ovaj način dobiveni spoj s formulom (I), u naknadnom koraku, reagira s natrijevim hidroksidom ili vodenom otopinom natrijevog hidroksida ili natrijevog metoksida ili natrijevog etoksida ili natrijeve soli da nastane natrijev 1-[6-(morfolin-4-il)pirimidin-4-il]-4-(1H-1,2,3-triazol-1-il)-1H-pirazol-5-olat (II).
6. Postupak prema bilo kojem od zahtjeva 1 do 4, naznačen time da se 4-(6-hidrazinopirimidin-4-il)morfolin (XI) priprema pomoću, u prvoj fazi, prvo reakcijom 4,6-dikloropirimidina (VIII) s hidrazin hidratom (XII hidrat) u otapalu, proizvoljno u prisutnosti pomoćne baze, te zagrijavanjem dobivene reakcijske smjese bez izolacije nastalog 4-kloro-6-hidrazinopirimidina (XV) u drugoj fazi nakon dodavanja morfolina (IX) i druge pomoćne baze i zatim se nakon kristalizacije izolira spoj s formulom (XI).
7. Postupak prema zahtjevu 6, naznačen time da se reakcija provodi upotrebom trietilamina ili etildiizopropilamina kao pomoćne baze.
8. Postupak prema jednom od zahtjeva 6 i 7, naznačen time da se reakcija provodi upotrebom natrijevog hidrogenkarbonata, kalijevog hidrogenkarbonata, natrijevog hidroksida ili kalijevog hidroksida kao dodatne pomoćne baze.
9. Postupak prema bilo kojem od zahtjeva 1 do 4, naznačen time da se metil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Me) ili etil (2E/Z)-3-(dimetilamino)-2-(1H-1,2,3-triazol-1-il)akrilat (VII-Et) priprema reakcijom spojeva metil-1H-1,2,3-triazol-1-il acetata (V-Me) i metil-2H-1,2,3-triazol-1-il acetata (VI-Me) ili spojeva etil-1H-1,2,3-traizol-1-il acetata (V-Et) i etil-2H-1,2,3-triazol-1-il acetata (VI-Et), koji su prisutni u međusobnom omjeru od barem 6:1, s dimetilformamid dimetil acetalom (XIX-Me) ili dimetilformamid dietil acetalom (XIX-Et) u inertnom otapalu i zatim kristalizira produkt hlađenjem otopine ili destilacijom otapala i dodavanjem drugog otapala.
10. Postupak prema zahtjevu 9, naznačen time da se spojevi metil-1H-1,2,3-triazol-1-il acetat (V-Me) i metil-2H-1,2,3-triazol-1-il acetat (VI-Me) ili spojevi etil-1H-1,2,3-traizol-1-il acetat (V-Et) i etil-2H-1,2,3-triazol-1-il acetat (VI-Et) dobivaju reakcijom 1,2,3-triazola (III) s metil bromoacetatom (IV-Me-Br) ili etil bromoacetatom (IV-Et-Br) u prisutnosti etildiizopropilamina kao baze u otapalu u temperaturnom rasponu od 20 do 80°C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12167152 | 2012-05-08 | ||
| EP13720943.3A EP2847183B1 (de) | 2012-05-08 | 2013-05-06 | Verfahren zur herstellung von triazol-verbindungen |
| PCT/EP2013/059418 WO2013167552A1 (de) | 2012-05-08 | 2013-05-06 | Verfahren zur herstellung von triazol-verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171321T1 true HRP20171321T1 (hr) | 2017-10-20 |
Family
ID=48325714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171321TT HRP20171321T1 (hr) | 2012-05-08 | 2017-08-31 | Postupak za pripremanje spojeva triazola |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US10301289B2 (hr) |
| EP (1) | EP2847183B1 (hr) |
| JP (1) | JP6149104B2 (hr) |
| KR (1) | KR102086389B1 (hr) |
| CN (1) | CN104411704B (hr) |
| AP (1) | AP2014008089A0 (hr) |
| AU (1) | AU2013258107B2 (hr) |
| BR (1) | BR112014027564B1 (hr) |
| CA (1) | CA2872726C (hr) |
| CL (2) | CL2014003003A1 (hr) |
| CO (1) | CO7121324A2 (hr) |
| CR (1) | CR20140514A (hr) |
| CU (1) | CU20140128A7 (hr) |
| DK (1) | DK2847183T3 (hr) |
| DO (1) | DOP2014000254A (hr) |
| EA (1) | EA027804B1 (hr) |
| ES (1) | ES2641205T3 (hr) |
| HK (1) | HK1208027A1 (hr) |
| HR (1) | HRP20171321T1 (hr) |
| HU (1) | HUE034430T2 (hr) |
| IL (1) | IL235441A (hr) |
| LT (1) | LT2847183T (hr) |
| MX (1) | MX350519B (hr) |
| MY (1) | MY184577A (hr) |
| NZ (1) | NZ701661A (hr) |
| PE (1) | PE20142453A1 (hr) |
| PH (1) | PH12014502482A1 (hr) |
| PL (1) | PL2847183T3 (hr) |
| PT (1) | PT2847183T (hr) |
| RS (1) | RS56255B1 (hr) |
| SG (2) | SG10201609319YA (hr) |
| SI (1) | SI2847183T1 (hr) |
| TN (1) | TN2014000469A1 (hr) |
| UA (1) | UA116349C2 (hr) |
| WO (1) | WO2013167552A1 (hr) |
| ZA (1) | ZA201408571B (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY37222A (es) * | 2016-05-03 | 2017-11-30 | Bayer Pharma AG | PROCEDIMIENTO PARA LA PREPARACIÓN DE DERIVADOS DE 1-FENILO-1,2,4-TRIAZOL SUSTITUIDOS POR 5-HIdroxIalQUILO |
| CN108084099B (zh) * | 2017-12-20 | 2019-01-29 | 天驰药业有限公司 | 一种1,2,3-三氮唑化合物的合成方法 |
| US10702525B1 (en) | 2019-09-04 | 2020-07-07 | United Arab Emirates University | Pyrimidine derivatives as anti-diabetic agents |
| EP3888684A1 (en) | 2020-03-31 | 2021-10-06 | Bayer Animal Health GmbH | Composition having improved voluntary acceptance |
| CN114264752B (zh) * | 2021-12-29 | 2023-08-15 | 北京金城泰尔制药有限公司 | 溴乙酸甲酯的检测方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4572910A (en) * | 1983-03-03 | 1986-02-25 | Riker Laboratories, Inc. | Triazolo[1,5-c]pyrimidines substituted by nitrogen-containing heterocyclic rings |
| DK135184A (da) | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | Triazol(4,3-c)- og triazol(1,5-c)pyrimidiner |
| US4752910A (en) | 1984-10-30 | 1988-06-21 | Prime Computer, Inc. | Method and apparatus for continuous after-imaging |
| UY27813A1 (es) * | 2002-05-31 | 2003-12-31 | Smithkline Beecham Corp | Inhibidores de la peptido-desformilasa |
| AR042052A1 (es) | 2002-11-15 | 2005-06-08 | Vertex Pharma | Diaminotriazoles utiles como inhibidores de proteinquinasas |
| AU2004287849A1 (en) * | 2003-10-30 | 2005-05-19 | Merck Sharp & Dohme Corp. | Aralkyl amines as cannabinoid receptor modulators |
| US7745630B2 (en) | 2003-12-22 | 2010-06-29 | Justin Stephen Bryans | Triazolyl piperidine arginine vasopressin receptor modulators |
| DE102008020113A1 (de) | 2008-04-23 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dihydropyrazolone und ihre Verwendung |
| JP2008539220A (ja) | 2005-04-26 | 2008-11-13 | ファイザー・リミテッド | バソプレシンアンタゴニストとしてのトリアゾール誘導体 |
| WO2006123242A1 (en) | 2005-05-18 | 2006-11-23 | Pfizer Limited | 1, 2, 4 -triazole derivatives as vasopressin antagonists |
| DE102006050516A1 (de) * | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dihydropyrazolone und ihre Verwendung |
| DE102010041236A1 (de) * | 2010-09-23 | 2012-03-29 | Osram Ag | Optoelektronisches Halbleiterbauelement |
| DE102010044131A1 (de) * | 2010-11-18 | 2012-05-24 | Bayer Schering Pharma Aktiengesellschaft | Substituiertes Natrium-1H-pyrazol-5-olat |
-
2013
- 2013-05-06 PE PE2014001942A patent/PE20142453A1/es active IP Right Grant
- 2013-05-06 ES ES13720943.3T patent/ES2641205T3/es active Active
- 2013-05-06 UA UAA201413001A patent/UA116349C2/uk unknown
- 2013-05-06 AU AU2013258107A patent/AU2013258107B2/en active Active
- 2013-05-06 HU HUE13720943A patent/HUE034430T2/en unknown
- 2013-05-06 RS RS20170869A patent/RS56255B1/sr unknown
- 2013-05-06 EA EA201492032A patent/EA027804B1/ru not_active IP Right Cessation
- 2013-05-06 KR KR1020147033989A patent/KR102086389B1/ko active IP Right Grant
- 2013-05-06 JP JP2015510775A patent/JP6149104B2/ja active Active
- 2013-05-06 PT PT137209433T patent/PT2847183T/pt unknown
- 2013-05-06 SG SG10201609319YA patent/SG10201609319YA/en unknown
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