HRP20211916T1 - Postupak pripreme [5-(3-klorofenil)-3-hidroksipiridin-2-karbonil)-amino]ocetne kiseline iz 5-((3-klorofenil)-3-klor-piridin-2-il)-nitrila, i postupak pripreme 5-((halofenil)-3-halo-piridin-2-il)-nitril derivata - Google Patents
Postupak pripreme [5-(3-klorofenil)-3-hidroksipiridin-2-karbonil)-amino]ocetne kiseline iz 5-((3-klorofenil)-3-klor-piridin-2-il)-nitrila, i postupak pripreme 5-((halofenil)-3-halo-piridin-2-il)-nitril derivata Download PDFInfo
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- HRP20211916T1 HRP20211916T1 HRP20211916TT HRP20211916T HRP20211916T1 HR P20211916 T1 HRP20211916 T1 HR P20211916T1 HR P20211916T T HRP20211916T T HR P20211916TT HR P20211916 T HRP20211916 T HR P20211916T HR P20211916 T1 HRP20211916 T1 HR P20211916T1
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- Croatia
- Prior art keywords
- chlorophenyl
- image
- cyanopyridine
- hydroxypyridine
- chloro
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 2
- JGRXMPYUTJLTKT-UHFFFAOYSA-N 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid Chemical compound C1=C(O)C(C(=O)NCC(=O)O)=NC=C1C1=CC=CC(Cl)=C1 JGRXMPYUTJLTKT-UHFFFAOYSA-N 0.000 title 1
- 125000005059 halophenyl group Chemical group 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical group [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims 6
- DYUOYBIHGUNMQN-UHFFFAOYSA-N 3-chloro-5-(3-chlorophenyl)pyridine-2-carbonitrile Chemical compound ClC1=CC=CC(C=2C=C(Cl)C(C#N)=NC=2)=C1 DYUOYBIHGUNMQN-UHFFFAOYSA-N 0.000 claims 4
- KMZAXKDGIXGPOF-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-hydroxypyridine-2-carboxylic acid Chemical compound C1=C(O)C(C(=O)O)=NC=C1C1=CC=CC(Cl)=C1 KMZAXKDGIXGPOF-UHFFFAOYSA-N 0.000 claims 4
- LQXLPTXROAPSNP-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-methoxypyridine-2-carbonitrile Chemical compound N1=C(C#N)C(OC)=CC(C=2C=C(Cl)C=CC=2)=C1 LQXLPTXROAPSNP-UHFFFAOYSA-N 0.000 claims 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 235000015320 potassium carbonate Nutrition 0.000 claims 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 3
- YTLGQWBFHNKITM-UHFFFAOYSA-N methyl 2-[[5-(3-chlorophenyl)-3-hydroxypyridin-2-yl]amino]acetate Chemical compound C1=C(O)C(NCC(=O)OC)=NC=C1C1=CC=CC(Cl)=C1 YTLGQWBFHNKITM-UHFFFAOYSA-N 0.000 claims 3
- ATUOLSDAAPMVJJ-UHFFFAOYSA-N 3,5-dichloropyridine-2-carbonitrile Chemical compound ClC1=CN=C(C#N)C(Cl)=C1 ATUOLSDAAPMVJJ-UHFFFAOYSA-N 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims 2
- HGROHYJKYOVLRM-UHFFFAOYSA-N (3-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(Cl)=C1 HGROHYJKYOVLRM-UHFFFAOYSA-N 0.000 claims 1
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 235000010216 calcium carbonate Nutrition 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 235000011116 calcium hydroxide Nutrition 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- -1 substituted aryl boric acid Chemical compound 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
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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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
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- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
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- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
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Claims (10)
1. Postupak za pripremu spoja formule:
[image]
koji se sastoji od:
reakcije supstituirane aril borne kiseline:
[image]
s 3,5-dihalo-2-cijanopiridinom:
[image]
u prisutnosti katalizatora,
pri čemu
prsten A je fenil,
R10 predstavlja od 1 do 5 neovisno odabranih supstitucija za vodik koji je halogen, i
svaki Z je neovisno klor ili brom.
2. Postupak prema zahtjevu 1, naznačen time što je katalizator [1,1’-bis (difenilfosfino)ferocen]dikloro paladij(II).
3. Postupak prema zahtjevu 1, naznačen time što se reakcija provodi u prisutnosti baze.
4. Postupak prema zahtjevu 3, naznačen time što je baza LiOH, NaOH, KOH, Ca(OH)2, Li2CO3, Na2CO3, K2CO3, ili CaCO3.
5. Postupak prema zahtjevu 4, naznačen time što je baza K2CO3.
6. Postupak prema zahtjevu 1, naznačen time što uključuje reakciju (3-klorofenil)borne kiseline:
[image]
s 3,5-dikloro-2-cijanopiridinom:
[image]
u prisutnosti K2CO3, [1,1’-bis (difenilfosfino)ferocen]dikloro paladija(II), u DMF-u na 45 °C da nastane 5-(3-klorofenil)-3-kloro-2-cijanopiridin:
[image]
7. Postupak prema zahtjevu 6, dalje uključuje reakciju 5-(3-klorofenil)-3-kloro-2-cijanopiridina s natrijevim met-oksidom i metanolom pri refluksu da nastane 5-(3-klorofenil)-3-metoksi-2-cijanopiridin:
[image]
reakciju 5-(3-klorofenil)-3-metoksi-2-cijanopiridina s 48% bromovodične kiseline na refluksu da nastane 5-(3-klorofenil)-3-hidroksipiridin-2-karboksilna kiselina.
[image]
8. Postupak prema zahtjevu 7, dalje uključuje reakciju 5-(3-klorofenil)-3-hidroksipiridin-2-karboksilne kiseline s glicin metil esterom:
[image]
u prisutnosti karbonildiimidazola (CDI) i DIPEA u DMSO na sobnoj temperaturi da nastane metil {[5-(3-klorofenil)-3-hidroksipiridin-2-il]amino}acetat:
[image]
9. Postupak prema zahtjevu 8, dalje uključuje reakciju metil {[5-(3-klorofenil)-3-hidroksipiridin-2-il]amino}acetata s natrijevim hidroksidom u THF-u da nastane spoj (5):
[image]
10. Postupak pripreme spoja (5):
[image]
koji se sastoji od:
A. reakcije (3-klorofenil)borne kiseline:
[image]
s 3,5-dikloro-2-cijanopiridinom:
[image]
u prisutnosti [1,1’-bis(difenilfosfino)ferocen]dikloro paladija(II) i K2CO3 u DMF-u na 45 °C da nastane 5-(3-klorofenil)-3-kloro-2-cijanopiridin:
[image]
B. reakcije 5-(3-klorofenil)-3-kloro-2-cijanopiridina s natrijevim metoksidom u metanolu pri refluksu da nastane 5-(3-klorofenil)-3-metoksi-2-cijanopiridin:
[image]
C. reakcije 5-(3-klorofenil)-3-metoksi-2-cijanopiridina s 48% bromovodične kiseline pri refluksu da nastane 5-(3-klorofenil)-3-hidroksipiridin-2-karboksilna kiselina:
[image]
D. reakcije 5-(3-klorofenil)-3-hidroksipiridin-2-karboksilne kiseline s glicin metil esterom:
[image]
u prisutnosti CDI i DIPEA u DMSO na sobnoj temperaturi da nastane metil {[5-(3-klorofenil)-3-hidroksi-ipiridin-2-il]amino}acetat:
[image]
E. reakcije metil {[5-(3-klorofenil)-3-hidroksipiridin-2-il]amino}acetata s natrijevim hidroksidom u THF-u da nastane spoj (5):
[image]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161493536P | 2011-06-06 | 2011-06-06 | |
| EP19214405.3A EP3683209B1 (en) | 2011-06-06 | 2012-06-05 | Process for preparing [(5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl)-amino]acetic acid from 5-((3-chlorophenyl)-3-chloro-pyridin-2-yl)-nitrile, and process for preparing 5-((halophenyl)-3-halo-pyridin-2-yl)-nitrile derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211916T1 true HRP20211916T1 (hr) | 2022-03-18 |
Family
ID=47262177
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211916TT HRP20211916T1 (hr) | 2011-06-06 | 2012-06-05 | Postupak pripreme [5-(3-klorofenil)-3-hidroksipiridin-2-karbonil)-amino]ocetne kiseline iz 5-((3-klorofenil)-3-klor-piridin-2-il)-nitrila, i postupak pripreme 5-((halofenil)-3-halo-piridin-2-il)-nitril derivata |
| HRP20151416T HRP20151416T1 (hr) | 2011-06-06 | 2015-12-23 | Postupak pripreme /(3-hidroksipiridin-2-karbonil)amino//alkanskih kiselina, estera i amida |
| HRP20171740TT HRP20171740T1 (hr) | 2011-06-06 | 2017-11-13 | Derivati 5-((halofenil)-3-hidroksi-piridin-2-yl-karboksilne kiseline kao posrednici za pripravu karbonilamino alkanoinskih kiselina, njihovih estera i amida |
| HRP20200197TT HRP20200197T1 (hr) | 2011-06-06 | 2020-02-06 | 5-((halofenil)-3-halo-piridin-2-il)-nitrilni derivati kao posrednici u pripremi [(5-(halofenila)-3-hidroksipiridin-2-karbonil)-amino]derivata alkanske kiseline |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20151416T HRP20151416T1 (hr) | 2011-06-06 | 2015-12-23 | Postupak pripreme /(3-hidroksipiridin-2-karbonil)amino//alkanskih kiselina, estera i amida |
| HRP20171740TT HRP20171740T1 (hr) | 2011-06-06 | 2017-11-13 | Derivati 5-((halofenil)-3-hidroksi-piridin-2-yl-karboksilne kiseline kao posrednici za pripravu karbonilamino alkanoinskih kiselina, njihovih estera i amida |
| HRP20200197TT HRP20200197T1 (hr) | 2011-06-06 | 2020-02-06 | 5-((halofenil)-3-halo-piridin-2-il)-nitrilni derivati kao posrednici u pripremi [(5-(halofenila)-3-hidroksipiridin-2-karbonil)-amino]derivata alkanske kiseline |
Country Status (24)
| Country | Link |
|---|---|
| US (6) | US9145366B2 (hr) |
| EP (5) | EP3290404B1 (hr) |
| JP (6) | JP6290781B2 (hr) |
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