Category: 1160936-51-5

On June 19, 2009, O’Shea, Paul D.; Gauvreau, Danny; Gosselin, Francis; Hughes, Greg; Nadeau, Christian; Roy, Amelie; Shultz, C. Scott published an article.COA of Formula: C6H3BrN2O The title of the article was Practical Synthesis of a Potent Bradykinin B1 Antagonist via Enantioselective Hydrogenation of a Pyridyl N-Acyl Enamide. And the article contained the following:

A practical and efficient synthesis of bradykinin B1 antagonist I is described. A convergent strategy was utilized which involved synthesis of three fragments: II, III and IV. Cross coupling of fragments II and III followed by amidation with IV enabled efficient synthesis of I in 19 steps total, a 35% overall yield from com. available 5-bromo-3-nitropyridin-2-ol. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine III and a catalytic enantioselective hydrogenation of N-acyl enamide V to set the stereochem. The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).COA of Formula: C6H3BrN2O

The Article related to fluorodenitration rhodium catalyst stereoselective hydrogenation acyl enamide, bradykinin b 1 antagonist stereoselective preparation, Heterocyclic Compounds (More Than One Hetero Atom): Oxazoles, Isoxazoles and other aspects.COA of Formula: C6H3BrN2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On May 27, 2021, Shen, Chunli; Sun, Guanglong; Wu, Chengde; Chen, Shuhui published a patent.Reference of 5-Bromo-3-hydroxypicolinonitrile The title of the patent was Bicyclic compound used as selective androgen receptor modulator. And the patent contained the following:

Disclosed are a bicyclic compound used as a non-steroidal selective androgen receptor modulator and the use thereof in the preparation of a drug for treating related diseases which are mediated by an androgen receptor. Specifically, the present invention discloses a compound as shown in formula I or a pharmaceutically acceptable salt thereof. The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).Reference of 5-Bromo-3-hydroxypicolinonitrile

The Article related to bicyclic compound preparation androgen receptor modulator treatment disease, Alicyclic Compounds: Bicyclic Compounds, Including Azulenes, Heptalenes, and Pentalenes and other aspects.Reference of 5-Bromo-3-hydroxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 23, 2019, Jung, Won Hyeok published a patent.Name: 5-Bromo-3-hydroxypicolinonitrile The title of the patent was Preparation of phenylacetylene derivatives as inhibitors against interaction between PD-1 and PD-L1. And the patent contained the following:

The invention relates to compounds of formula I or pharmaceutically acceptable salts thereof that are useful for the prevention and treatment of cancer or autoimmune disease as inhibitors against interaction between programmed death 1 (PD-1) and programmed death-ligand 1 (PD-L1). Compounds of formula I wherein X1=X2 is N=C-R11, R11-C=N, N=N, or C=C; R1 is (CH)n-CO2H, O-R9, CO-(NH-R9), CO-R9, NH-R9, N(R9)2, N(R9)(R10), etc.; n is 0-4; R2 is H, halo, alkyl, cyano, hydroxy, amino, CO-alkyl, O-alkyl, O-(CH2)m-heteroaryl, O-(CH2)m-cycloalkyl, O-(CH2)m-heterocyclyl, NH-alkyl, etc.; m is 0-4; R3, R6, R7, R8, and R11 are independently H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, etc.; R4 is H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, CO-alkyl, etc.; R5 is (un)substituted (hetero)aryl, (un)substituted cycloalkyl, or (un)substituted heterocyclyl; R9 and R10 are independently (un)substituted alkyl; are claimed. Example compound II was prepared via Sonogashira coupling reaction of Me 6-ethynylpyridazine-3-carboxylate with 3-bromo-2-methyl-[1,1′-biphenyl], followed by Dibal-H reduction, reductive amination with Me glycinate hydrochloride, and basic hydrolysis. The invention compounds were evaluated for the inhibitory activity against interaction between PD-1 and PD-L1 (biol. activity given). The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).Name: 5-Bromo-3-hydroxypicolinonitrile

The Article related to phenylacetylene derivative preparation pd1 pdl1 inhibition cancer autoimmune disease, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Name: 5-Bromo-3-hydroxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 18, 2019, Jung, Won-Hyuk published a patent.Application of 1160936-51-5 The title of the patent was Preparation of phenylacetylene derivatives as inhibitors against interaction between PD-1 and PD-L1. And the patent contained the following:

The invention relates to compounds of formula I or pharmaceutically acceptable salts thereof that are useful for the prevention and treatment of cancer or autoimmune disease as inhibitors against interaction between programmed death 1 (PD-1) and programmed death-ligand 1 (PD-L1). Compounds of formula I wherein X1=X2 is N=C-R11, R11-C=N, N=N, or C=C; R1 is (CH)n-CO2H, O-R9, CO-(NH-R9), CO-R9, NH-R9, N(R9)2, N(R9)(R10), etc.; n is 0-4; R2 is H, halo, alkyl, cyano, hydroxy, amino, CO-alkyl, O-alkyl, O-(CH2)m-heteroaryl, O-(CH2)m-cycloalkyl, O-(CH2)m-heterocyclyl, NH-alkyl, etc.; m is 0-4; R3, R6, R7, R8, and R11 are independently H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, etc.; R4 is H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, CO-alkyl, etc.; R5 is (un)substituted (hetero)aryl, (un)substituted cycloalkyl, or (un)substituted heterocyclyl; R9 and R10 are independently (un)substituted alkyl; are claimed. Example compound II was prepared via Sonogashira coupling reaction of Me 6-ethynylpyridazine-3-carboxylate with 3-bromo-2-methyl-[1,1′-biphenyl], followed by Dibal-H reduction, reductive amination with Me glycinate hydrochloride, and basic hydrolysis. The invention compounds were evaluated for the inhibitory activity against interaction between PD-1 and PD-L1 (biol. activity given). The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).Application of 1160936-51-5

The Article related to phenylacetylene derivative preparation pd1 pdl1 inhibition cancer autoimmune disease, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Application of 1160936-51-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 23, 2019, Jung, Won Hyeok published a patent.Name: 5-Bromo-3-hydroxypicolinonitrile The title of the patent was Preparation of phenylacetylene derivatives as inhibitors against interaction between PD-1 and PD-L1. And the patent contained the following:

The invention relates to compounds of formula I or pharmaceutically acceptable salts thereof that are useful for the prevention and treatment of cancer or autoimmune disease as inhibitors against interaction between programmed death 1 (PD-1) and programmed death-ligand 1 (PD-L1). Compounds of formula I wherein X1=X2 is N=C-R11, R11-C=N, N=N, or C=C; R1 is (CH)n-CO2H, O-R9, CO-(NH-R9), CO-R9, NH-R9, N(R9)2, N(R9)(R10), etc.; n is 0-4; R2 is H, halo, alkyl, cyano, hydroxy, amino, CO-alkyl, O-alkyl, O-(CH2)m-heteroaryl, O-(CH2)m-cycloalkyl, O-(CH2)m-heterocyclyl, NH-alkyl, etc.; m is 0-4; R3, R6, R7, R8, and R11 are independently H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, etc.; R4 is H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, CO-alkyl, etc.; R5 is (un)substituted (hetero)aryl, (un)substituted cycloalkyl, or (un)substituted heterocyclyl; R9 and R10 are independently (un)substituted alkyl; are claimed. Example compound II was prepared via Sonogashira coupling reaction of Me 6-ethynylpyridazine-3-carboxylate with 3-bromo-2-methyl-[1,1′-biphenyl], followed by Dibal-H reduction, reductive amination with Me glycinate hydrochloride, and basic hydrolysis. The invention compounds were evaluated for the inhibitory activity against interaction between PD-1 and PD-L1 (biol. activity given). The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).Name: 5-Bromo-3-hydroxypicolinonitrile

The Article related to phenylacetylene derivative preparation pd1 pdl1 inhibition cancer autoimmune disease, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Name: 5-Bromo-3-hydroxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 18, 2019, Jung, Won-Hyuk published a patent.Application of 1160936-51-5 The title of the patent was Preparation of phenylacetylene derivatives as inhibitors against interaction between PD-1 and PD-L1. And the patent contained the following:

The invention relates to compounds of formula I or pharmaceutically acceptable salts thereof that are useful for the prevention and treatment of cancer or autoimmune disease as inhibitors against interaction between programmed death 1 (PD-1) and programmed death-ligand 1 (PD-L1). Compounds of formula I wherein X1=X2 is N=C-R11, R11-C=N, N=N, or C=C; R1 is (CH)n-CO2H, O-R9, CO-(NH-R9), CO-R9, NH-R9, N(R9)2, N(R9)(R10), etc.; n is 0-4; R2 is H, halo, alkyl, cyano, hydroxy, amino, CO-alkyl, O-alkyl, O-(CH2)m-heteroaryl, O-(CH2)m-cycloalkyl, O-(CH2)m-heterocyclyl, NH-alkyl, etc.; m is 0-4; R3, R6, R7, R8, and R11 are independently H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, etc.; R4 is H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, CO-alkyl, etc.; R5 is (un)substituted (hetero)aryl, (un)substituted cycloalkyl, or (un)substituted heterocyclyl; R9 and R10 are independently (un)substituted alkyl; are claimed. Example compound II was prepared via Sonogashira coupling reaction of Me 6-ethynylpyridazine-3-carboxylate with 3-bromo-2-methyl-[1,1′-biphenyl], followed by Dibal-H reduction, reductive amination with Me glycinate hydrochloride, and basic hydrolysis. The invention compounds were evaluated for the inhibitory activity against interaction between PD-1 and PD-L1 (biol. activity given). The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).Application of 1160936-51-5

The Article related to phenylacetylene derivative preparation pd1 pdl1 inhibition cancer autoimmune disease, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Application of 1160936-51-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts