Li, Liansheng et al. published their patent in 2018 |CAS: 1620510-51-1

The Article related to quinazoline preparation g12c mutant kras inhibitor antitumor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.SDS of cas: 1620510-51-1

On November 29, 2018, Li, Liansheng; Feng, Jun; Wu, Tao; Liu, Yuan; Wang, Yi; Ren, Pingda; Liu, Yi published a patent.SDS of cas: 1620510-51-1 The title of the patent was Preparation of substituted quinazolines as covalent inhibitors of KRAS. And the patent contained the following:

The title compounds I [G1 and G2 = (independently) N or CH; L1 = a bond or NR6; L2 = a bond or alkylene; L3 = a bond, O, NR6, S, S(O) or SO2; R1 = unsubstituted naphthyl or optionally substituted quinolinyl when at least one of R31, R32, R41 and R42 is not H; or R1 = II (A1-A4 = (independently) C or N; X = O, S, N, etc.;Y = O, S, N, etc.; Z = O, S, N, etc.; one of R11-R14 is a covalent bond to the carbon attached to R1, and the other of R11-R14 = (independently) H, NH2, CN, etc.; R21-R23 = (independently) H, NH2, CN, etc.; R31 and R32 = (independently) H, OH, NH2, etc.; R41 and R42 = (independently) H, OH, NH2, etc.; R5 = NH2, CN, OH, etc.; R6 = (independently) H or alkyl; m and n = (independently) 1-3; and E = an electrophilic moiety capable of forming a covalent bond with the cysteine residue at position 12 of a KRAS, HRAS or NRAS G12C mutant protein)] or pharmaceutically acceptable salts, isotopic forms, stereoisomers or prodrugs thereof, having activity as inhibitors of G12C mutant KRAS protein, were prepared E.g., a multi-step synthesis of (2R,5S)-III, starting from 2-amino-4-bromo-3-fluorobenzoic acid, was described. Representative compounds I were tested and found to covalently bind to (or modify) KRAS G12C after a ten minute incubation period (data given). Pharmaceutical compositions comprising compounds I, and methods to modulate the activity of G12C mutant KRAS protein for treatment of disorders, such as cancer, were also provided. The experimental process involved the reaction of (R)-(4-Methylmorpholin-3-yl)methanol(cas: 1620510-51-1).SDS of cas: 1620510-51-1

The Article related to quinazoline preparation g12c mutant kras inhibitor antitumor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.SDS of cas: 1620510-51-1

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Guo, Hongli et al. published their patent in 2021 |CAS: 1620510-51-1

The Article related to quinazoline compound preparation kras g12c inhibitor antitumor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of (R)-(4-Methylmorpholin-3-yl)methanol

On March 30, 2021, Guo, Hongli; Chen, Tao; Zhou, Feng; Gao, Daxin; Chen, Dawei published a patent.Reference of (R)-(4-Methylmorpholin-3-yl)methanol The title of the patent was Preparation of quinazoline-based compounds as KRAS G12C inhibitor for treatment and/or alleviation of KRAS G12C-related diseases. And the patent contained the following:

The present invention relates to preparation of quinazoline-based compounds as KRAS G12C inhibitor for treatment and/or alleviation of KRAS G12C-related diseases. In particular, the quinazoline-based compound I (wherein, α and β bonds are single bonds or double bonds, resp.; X = N or CR2; when the β bond is a single bond, Y = C(O) and Z = NR3; when the β bond is a double bond, Y and Z are independently N or CR2; when the α bond is a single bond, W = N and V = CH2 or C(O); when the a bond is a double bond, W = C and V = CR4 or N; U and M are each independently N, C or CH; ring A = Ph, 3-8 membered cycloalkyl, 5-6 membered heteroaryl or 4-8 membered heterocycloalkyl group; the A ring is unsubstituted or optionally substituted). Further, (ring B = 5-10 membered heterocycloalkyl; the B ring is unsubstituted or optionally substituted; R = C6-10 aryl, 5-10 membered heteroaryl or 9-14 membered fused heterocycloalkyl group; said R is unsubstituted or optionally substituted; R1 = C2-4 alkenyl, C2-4 alkynyl or partially unsaturated C4-6 cycloalkyl; said R1 is unsubstituted or optionally substituted; R2 = H, hydroxyl, halogen, cyano, amino etc.; R3 = C3-8 cycloalkyl, 3-8 membered heterocycloalkyl, C6-10 aryl, 5-10 heteroaryl, C3-8 cycloalkyl-C1-4 alkyl etc.; R4 = H, hydroxyl, halogen, C2-6 alkenyl, C2-6 alkynyl, cyano, amino etc.), its isomers, stable isotope derivatives or pharmaceutically acceptable salts were prepared The inventive compound and its composition disclosed can effectively treat diseases related to KRAS G12C, such as cancer. The experimental process involved the reaction of (R)-(4-Methylmorpholin-3-yl)methanol(cas: 1620510-51-1).Reference of (R)-(4-Methylmorpholin-3-yl)methanol

The Article related to quinazoline compound preparation kras g12c inhibitor antitumor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of (R)-(4-Methylmorpholin-3-yl)methanol

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Claremon, David A. et al. published their patent in 2016 |CAS: 386704-04-7

The Article related to piperazine derivative preparation liver receptor lxr modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Application of 386704-04-7

On February 11, 2016, Claremon, David A.; Dong, Chengguo; Fan, Yi; Leftheris, Katerina; Lotesta, Stephen D.; Singh, Suresh B.; Tice, Colin M.; Zhao, Wei; Zheng, Yajun; Zhuang, Linghang published a patent.Application of 386704-04-7 The title of the patent was Preparation of piperazine derivatives as liver X receptor modulators. And the patent contained the following:

Provided are novel compounds of formula I, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are liver X receptor modulators, and which are useful in the treatment of diseases and disorders associated with the liver X receptor. Also provided are the compounds of formula I and pharmaceutical compositions thereof for treating atherosclerosis, cardiovascular disease, Alzheimer’s disease, dermatitis, dyslipidemia, cancer and other diseases or disorders. Title compounds I [Q = alkyl-OC(O), heteroaryl, aryl-alkyl-OC(O), etc.; R1 = alkyl, cycloalkyl, aryl-alkyl, etc.; R2 = H, halo, cyano, etc.; R3 = alkyl, halo-alkyl, cycloalkyl, etc.; R4 = H or alkyl], and their pharmaceutically acceptable salts, are prepared Thus, e.g., II was prepared by reaction of (R)-tert-Bu 2-isopropylpiperazine-1-carboxylate with [3-(methylsulfonyl)phenyl]boronic acid. Compounds of the invention were evaluated for their LXr α/β binding ad agonist activity, e.g., II showed Ki value of 1690 nM and 157 nM on LXRα and LXRβ, resp. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Application of 386704-04-7

The Article related to piperazine derivative preparation liver receptor lxr modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Application of 386704-04-7

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Alcohol – Wikipedia,
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Bernasconi, Giovanni et al. published their patent in 2008 |CAS: 386704-04-7

The Article related to piperazinylacetohydrazide preparation ghrelin receptor modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.SDS of cas: 386704-04-7

On December 11, 2008, Bernasconi, Giovanni; Bromidge, Steven Mark; Carpenter, Andrew James; D’Adamo, Lucilla; Di Fabio, Romano; Guery, Sebastien; Pavone, Francesca; Pozzan, Alfonso; Rinaldi, Marilisa; Sabbatini, Fabio Maria; St-Denis, Yves published a patent.SDS of cas: 386704-04-7 The title of the patent was Preparation of N-phenyl piperidinyl- and piperazinylacetohydrazides as modulators of the ghrelin receptor. And the patent contained the following:

Title compounds [I; R1 = Cl, Br, Me, CF3; X = C, N; R1a = H, alkyl; R2a = H, Me; R2 = alkyl, H, (CH2)n, wherein n = 3, 4 and the terminal C of the chain is bonded to the C atom adjacent to the N bearing the R2 group, such that a fused 6,5 or 6,6-bicyclic ring is formed; Y = (substituted) Ph pyridyl, naphthyl, pyrimidinyl, imidazo[1,2-a]pyridine-6-yl, benzothiophen-2-yl, benzothiophen-5-yl, benzofuran-2-yl, dibenzo[b,d]furan-3-yl, dibenzo[b,d]thiophen-2-yl, dibenzo[b,d]thiophen-4-yl, 1,3-benzodioxol-5-yl, 2,3-dihydro-1,4-benzodioxin-5-yl, 2,3-dihydro-1,4-benzodioxin-6-yl, 2,3-dihydro-1-benzofuran-4-yl, 2,2-difluoro-1,3-benzodiox-4-yl, pyridazinyl, imidazolyl, oxazolyl, pyrazolyl, thiazolyl, triazolyl; when Y = 2,3-dihydro-1,4-benzodioxin-6-yl, R1 ≠ Cl], were prepared Thus, dibenzo[b,d]thien-4-ylboronic acid, glyoxylic acid hydrate, and 1-methylpiperazine were microwaved together in MeCN at 120° for 20 min. to give 53% dibenzo[b,d]thien-4-yl(4-methyl-1-piperazinyl)acetic acid hydrochloride. This was stirred with TBTU, PL-DIPAM, and 3,5-dichlorophenylhydrazine in DMF for 24 h at room temperature to give 31% 2-dibenzo[b,d]thien-4-yl-N’-(3,5-dichlorophenyl)-2-(4-methyl-1-piperazinyl)acetohydrazide formate. The latter and other I showed pIC50 values of >5.5 in the GHSR antagonist BACMAM FLIPR assay. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).SDS of cas: 386704-04-7

The Article related to piperazinylacetohydrazide preparation ghrelin receptor modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.SDS of cas: 386704-04-7

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Alcohol – Wikipedia,
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Lauffer, David J. et al. published their patent in 2019 |CAS: 386704-04-7

The Article related to pteridinone preparation treatment cellular proliferative disorder, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Application of 386704-04-7

On October 24, 2019, Lauffer, David J.; Bemis, Guy; Boyd, Michael; Deininger, David; Deng, Hongbo; Dorsch, Warren; Gu, Wenxin; Hoover, Russell R.; Johnson, Jr., Mac Arthur; Ledeboer, Mark Willem; Ledford, Brian; Maltais, Francois; Penney, Marina; Takemoto, Darin; Waal, Nathan D.; Weng, Tiansheng published a patent.Application of 386704-04-7 The title of the patent was Preparation of pteridinone compounds for the treatment of cellular proliferative disorders. And the patent contained the following:

The invention provides compounds of formula I, or pharmaceutically acceptable salts thereof, pharmaceutical compositions thereof, and methods of use thereof for treating cellular proliferative disorders (e.g., cancer). Compounds of formula I wherein A is (un)saturated 3- to 8-membered carbocyclic ring, indanyl, Ph, (un)saturated 4- to 8-membered monocyclic heterocyclic ring; L is a bond, (un)branched C1-6 hydrocarbyl and (un)branched C1-6 heterohydrocarbyl; R1 is H, (un)substituted C1-4 aliphatic, R’, etc.; R2 and R2′ are independently H, R’, (un)substituted C1-4 aliphatic, etc.; R3 is H, R’, and (un)substituted C1-6 aliphatic; R4 is H, R’, CH2OH, etc.; R5 is H, acyl, CO2H and derivatives, etc.;each R6 is independently halo, CN, NO2, acyl, etc.; R’ is C1-4 deuterioaliph.; X is N and CH; n is 0, 1, 2, 3, 4 and 5; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a general procedure (procedure given). The invention compounds were evaluated for their PLK1 inhibitory activity. From the assay, it was determined that compound II exhibited IC50 value of < 0.3 μM. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Application of 386704-04-7

The Article related to pteridinone preparation treatment cellular proliferative disorder, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Application of 386704-04-7

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Alcohol – Wikipedia,
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Bonnert, Roger et al. published their patent in 2001 |CAS: 72364-46-6

The Article related to pteridine preparation psoriasis chemokine receptor cxcr2 antagonist, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Recommanded Product: 72364-46-6

On August 30, 2001, Bonnert, Roger; Gardiner, Stewart; Hunt, Fraser; Walters, Iain published a patent.Recommanded Product: 72364-46-6 The title of the patent was Preparation of pteridine compounds for the treatment of psoriasis. And the patent contained the following:

The title compounds [I; A = II, III; R1 = (un)substituted cycloalkyl, alkyl, alkenyl, etc.; R2 = H, (un)substituted cycloalkyl, alkyl, etc.; R3 = H, (un)substituted alkyl; NR2R3 = (un)substituted 3-8 membered ring optionally containing one or more atoms selected from O, S, NR8; R8, R18, R19 = H, alkyl, Ph; X = O, S, NR8; Y = CR18R19; Z = CR20; R20 = alkyl, Ph], useful in the treatment of chemokine mediated diseases such as psoriasis, were prepared E.g., a 5-step synthesis of (1R)-IV was given. The compounds I were tested and found to be antagonists of the CXCR2 receptor in human neutrophils. The experimental process involved the reaction of (2-Fluorophenyl)methanethiol(cas: 72364-46-6).Recommanded Product: 72364-46-6

The Article related to pteridine preparation psoriasis chemokine receptor cxcr2 antagonist, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Recommanded Product: 72364-46-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Xia, Guangxin et al. published their patent in 2013 |CAS: 1620510-51-1

The Article related to quinazoline preparation protein tyrosine kinase inhibitor treatment cancer, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Synthetic Route of 1620510-51-1

On January 31, 2013, Xia, Guangxin; Shen, Jingkang; Yu, Yongping; Chen, Wenteng; Zhang, Chunchun; Hao, Yu; Zhang, Jing; Li, Bojun; Liu, Xuejun published a patent.Synthetic Route of 1620510-51-1 The title of the patent was Quinazoline derivatives as protein tyrosine kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer. And the patent contained the following:

Disclosed are quinazoline derivatives of formula I and their pharmaceutical acceptable salts, enantiomers, non-enantiomers, tautomers, racemates, solvates, metabolic precursors, and prodrugs. Also disclosed are a preparation method therefor, an intermediate, a pharmaceutical composition having the quinazoline derivatives, and an application thereof. The quinazoline derivatives of the invention are provided with improved anti-tumor activity. Compounds of formula I wherein R1 is (un)substituted C6-10 aryl, (un)substituted C3-12heteroaryl; R2 is H, halo, OH, amino, C1-6 (halo)alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, etc.; X is halo; R3 and R4 are independently H, C1-6 alkyl, R6R7N-(CH2)1-3-, R6R7N-(CH2)1-2-Y-(CH2)0-4- and Het-W-(CH2)0-2-; R6 and R7 are independently H, C1-6 alkyl, Het-W-(CH2)0-2- and R8-W-(CH2)0-4-; R8 is H, and C1-6 alkyl; Y is O, S and NH and derivatives; Z is NH and derivatives and O; W is NH and derivatives, O and a single bond; Het is 3- to 6-membered heterocyclic ring and 5-membered nitrogen-containing heteroaryl; and their pharmaceutical acceptable salts, enantiomers, non-enantiomers, tautomers, racemates, solvates, metabolic precursors, and prodrugs thereof, are claimed. Compounds of formula I were prepared by using condensation and Wittig olefination as the key steps. All the invention compounds were evaluated for their protein tyrosine kinase inhibitory activity. From the assay, it was determined that example compound II exhibited the IC50 value of 1.3, 75 and 23 nM against EGFR, HER2 and HER4, resp. The experimental process involved the reaction of (R)-(4-Methylmorpholin-3-yl)methanol(cas: 1620510-51-1).Synthetic Route of 1620510-51-1

The Article related to quinazoline preparation protein tyrosine kinase inhibitor treatment cancer, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Synthetic Route of 1620510-51-1

Referemce:
Alcohol – Wikipedia,
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Blagg, Julian et al. published their patent in 2021 |CAS: 55743-13-0

The Article related to heterocyclic benzamide preparation mlh1 pms2 protein inhibitor treatment cancer, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of 2,4,6-Trihydroxy-3-methylbenzaldehyde

On December 9, 2021, Blagg, Julian; Roffey, Jon; Drysdale, Martin; Winship, Paul; Clark, David published a patent.Reference of 2,4,6-Trihydroxy-3-methylbenzaldehyde The title of the patent was Heterocyclic benzamide compounds as MLH1 and/or PMS2 proteins inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer. And the patent contained the following:

The invention relates to heterocyclic benzamide compounds of formula I that target the MLH1 and/or PMS2 proteins that are components of the DNA Mismatch Repair (MMR) process. The invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which MLH1 and/or PMS2 activity is implicated. Compounds of formula I wherein R1 and R3 are independently H,OH, halo, C1-4 alkoxy; provided that as least one of the R1 and R3 is OH; R2 is H, F; R4 is H, halo, C1-6 alkyl, (un)substituted C3-6 cycloalkyl, (un)substituted C3-6 cycloalkyl-C1-2 alkyl, etc.; R6 is C1-6 alkyl, C3-8 cycloalkyl, C3-8 cycloalkyl-C1-2 alkyl, 4- to 7-membered cyclic ring, etc.; R10 is NR11R12; R11 and R12 are taken together with the nitrogen atom attached to form (un)substituted 5- to 7-membered heterocyclic ring fused with 5- to 6-membered monocyclic heteroaryl or with Ph to form 8- to 11-membered bicyclic heteroaryl; and their pharmaceutically acceptable salts, hydrates or solvates as MLH1 and/or PMS2 proteins inhibitors in the treatment of cancer thereof, are claimed. Example compound II was prepared by using amidation and desulfonylation as the key steps. All the invention compounds were evaluated for their MLH1 and/or PMS2 proteins inhibitory activity. The experimental process involved the reaction of 2,4,6-Trihydroxy-3-methylbenzaldehyde(cas: 55743-13-0).Reference of 2,4,6-Trihydroxy-3-methylbenzaldehyde

The Article related to heterocyclic benzamide preparation mlh1 pms2 protein inhibitor treatment cancer, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of 2,4,6-Trihydroxy-3-methylbenzaldehyde

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kane, John L., Jr. et al. published their patent in 2017 |CAS: 386704-04-7

The Article related to colony stimulating factor receptor inhibitors heterocyclic compound preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Formula: C7H6F3NO

On January 26, 2017, Kane, John L., Jr.; Barberis, Claude; Czekaj, Mark; Erdman, Paul; Giese, Barret; Kothe, Michael; Le, Tieu-Binh; Liu, Jinyu; Ma, Liang; Metz, Markus; Patel, Vinod; Scholte, Andrew; Shum, Patrick; Wei, Limli published a patent.Formula: C7H6F3NO The title of the patent was Preparation of nitrogen heterocycles as colony stimulating factor-1 receptor (CSF-1R) inhibitors. And the patent contained the following:

Compounds I [A = (CR1R2)n; M = (CR4R5)m; n is 0, 1, 2, 3, 4 or 5; m is 1, 2, 3 or 4; X1 is C, N or CR7, X2, X3, X4, X5, X6 and X7 are each independently selected from N, NR7 or CR7;]. [Wherein: each R7 is independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, C2-10-alkylnyl, (C1-10-alkyl)NH, (C1-0-alkyl)2N, (C2-10-alkynyl)NH, C(:O), (C1-10-alkyl)-CO2-, (C1-10-alkyl)-CO2H, (C3-10-cycloalkyl)-CO2H, C1-10-alkoxy, R8-(C1-10-alkyl), R8-(C3-10-cycloalkyl), NR8R9, etc.;]. [Wherein: R8 and R9 are each independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, COOH, (C1-10-alkyl)CO2H, etc.; or, R8 and R9 are taken together to form a 3 to 10 member cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring;]. [X8 and X9 are each independently selected from N or C; T1, T2 and T3 is each independently selected from are each independently selected from N or CR10; wherein: each R10 is independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, C2-10-alkylnyl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C2-10-alkynyl)NH, C(:O), (C1-10-alkyl)-CO2-, (C1-10-alkyl)-CO2H, (C3-10-cycloalkyl)-CO2H, C1-10-alkoxy, etc.;]. [Y1 is O, S, NR12 or CR12R13; wherein: R12 is absent or R12 and R13 are each independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, (C1-10-alkyl)CO2H, (C3-10-cycloalkyl)CO2H, C1-10-alkoxy, etc,;]. [R1 together with the carbon to which it is attached to form a carbonyl and R2 is absent; or, R1 and R2 are each independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, C1-10-alkoxy, etc.;]. [R4 is selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, C1-10-alkoxy, etc.; or, R4 and R5 can be taken together with the carbon to which they are attached to form a 3 to 10 member ring;]. [R5 is absent or selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, C1-10-alkoxy, etc.;]. [R6 is selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, C2-10-alkynyl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C2-10-alkynyl)NH, C(:O), etc.;]. [R3 is N or CR16; wherein: R16 is selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, (C1-10-alkyl)-CO2H,(C3-10-cycloalkyl)-CO2H, C1-10-alkoxy, etc.;]. [When m is 1, R16 and R4 are taken together with the carbons to which they are attached to form a compound; wherein the dashed lines represent optional double bonds;] and II [p is 0, 1, 2, 3, 4 or 5; Z = (CZ1)p; Z1 is each independently selected from H, halogen, C1-10-alkyl, C2-9-heteroalkyl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C2-10-alkynyl)NH, C1-10-alkoxy or NH2;]. [Y2 is O, S, NR17, or CR17R18, wherein R17 is absent, or R17 and R18 are each independently selected from H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, etc.;], or the pharmaceutically acceptable salt thereof, are described. Compounds I and II are useful as colony stimulating factor-1 receptor inhibitors (“”CSF-1R inhibitors””). Thus, 4-(1-((2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-1H-benzo[d]imidazol-5-yl)-2-methylbut-3-yn-2-amine (III) was prepared and tested for CSF-1R inhibition [c-FMS IC50 = 0.005 μM; Phospho c-FMS IC50 = 0,053 μM]. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Formula: C7H6F3NO

The Article related to colony stimulating factor receptor inhibitors heterocyclic compound preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Formula: C7H6F3NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kobayashi, Kaori et al. published their patent in 2015 |CAS: 386704-04-7

The Article related to heterocyclic sulfonamide preparation trpa1 antagonist pain digestive inflammatory, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.HPLC of Formula: 386704-04-7

On August 6, 2015, Kobayashi, Kaori; Suzuki, Tamotsu; Kawahira, Mizuki; Fujii, Tomohiro; Sugiki, Masayuki; Ohsumi, Koji; Okuzumi, Tatsuya published a patent.HPLC of Formula: 386704-04-7 The title of the patent was Preparation of heterocyclic sulfonamide derivatives as TRPA1 antagonists for treating pain, digestive diseases, and inflammatory diseases. And the patent contained the following:

The heterocyclic sulfonamide derivatives are represented by formula I [Q = O, S; A = 6-membered aromatic or heterocyclic ring, bicyclic aromatic or heterocyclic ring; A1 = C(Ra), N; A2 = C(Rb), N; A3 = C(Rc), N; A4 = C(Rd), N; Ra-Rd = H, halo, cyano, OH, C1-6 alkyl, etc.; least two of A1-A4 are not N; R1 = H, (un)substituted C1-6 alkyl; R2 = H, (un)substituted C1-6 alkyl or C2-6 alkenyl; R3-R5 = H, C1-6 alkyl; R1 and R2 may form (un)substituted heterocycle; R4 and R5 may form cycloalkane; X = (un)substitued C, (un)substited N, or S-containing Cy; Cy = (un)substituted and hetero-(un)containing saturated or unsaturated cyclic group; R6 = (un)substituted C1-6 alkyl, C2-6 alkenyl, halo, OH, amino, etc.; m = 0-3], excluding II. Thus, Mitsunobu reaction of (2S)-1-(benzofuran-2-ylsulfonyl)-N-[(3-hydroxyphenyl)methyl]pyrrolidine-2-carboxamide (preparation given) and 4-hydroxybenzonitrile (sic) gave (2S)-1-(benzofuran-2-ylsulfonyl)-N-[[3-[(4-cyanophenyl)methoxy]phenyl]methyl]pyrrolidine-2-carboxamide showing human transient receptor potential ankyrin 1 antagonistic activity (IC50) 0.0030 μM. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).HPLC of Formula: 386704-04-7

The Article related to heterocyclic sulfonamide preparation trpa1 antagonist pain digestive inflammatory, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.HPLC of Formula: 386704-04-7

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