TW200524590A

TW200524590A - Chemical compounds

Chemical compounds Download PDF

Info

Publication number: TW200524590A
Authority: TW; Taiwan
Prior art keywords: alkyl; hydroxy; formula; compound; group
Prior art date: 2003-08-22

Application number

TW093125218A

Other languages

English (en)

Chinese (zh)

Inventor

Stuart Norman Lile Bennett

Iain Simpson

Paul Robert Owen Whittamore

Original Assignee

Astrazeneca Ab

Priority date

2003-08-22

Filing date

2004-08-20

Publication date

2005-08-01

2004-08-20 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2005-08-01 Publication of TW200524590A publication Critical patent/TW200524590A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 185
125000000217 alkyl group Chemical group 0.000 claims abstract description 475
125000003545 alkoxy group Chemical group 0.000 claims abstract description 109
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 97
150000003839 salts Chemical class 0.000 claims abstract description 76
238000000034 method Methods 0.000 claims abstract description 51
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 36
239000001257 hydrogen Substances 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
239000000651 prodrug Substances 0.000 claims abstract description 21
229940002612 prodrug Drugs 0.000 claims abstract description 21
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 20
238000004519 manufacturing process Methods 0.000 claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
125000001475 halogen functional group Chemical group 0.000 claims abstract 6
-1 nitro, cyano, hydroxy, fluoromethyl Chemical group 0.000 claims description 441
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 152
238000006243 chemical reaction Methods 0.000 claims description 54
150000002148 esters Chemical class 0.000 claims description 47
229910052757 nitrogen Inorganic materials 0.000 claims description 36
150000001412 amines Chemical class 0.000 claims description 33
238000001727 in vivo Methods 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 27
239000007789 gas Chemical group 0.000 claims description 22
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 19
241001465754 Metazoa Species 0.000 claims description 17
125000006239 protecting group Chemical group 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 14
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 13
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 13
150000001335 aliphatic alkanes Chemical group 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 11
235000021419 vinegar Nutrition 0.000 claims description 11
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
239000000052 vinegar Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
241000282412 Homo Species 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 6
208000008589 Obesity Diseases 0.000 claims description 5
235000020824 obesity Nutrition 0.000 claims description 5
208000024891 symptom Diseases 0.000 claims description 5
206010022489 Insulin Resistance Diseases 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
201000001421 hyperglycemia Diseases 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
201000008980 hyperinsulinism Diseases 0.000 claims description 3
208000011580 syndromic disease Diseases 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
206010060378 Hyperinsulinaemia Diseases 0.000 claims description 2
206010061218 Inflammation Diseases 0.000 claims description 2
206010048849 Myocardial haemorrhage Diseases 0.000 claims description 2
229910052736 halogen Chemical group 0.000 claims description 2
230000003451 hyperinsulinaemic effect Effects 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
230000002107 myocardial effect Effects 0.000 claims description 2
241000894007 species Species 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
239000010247 gou-teng Substances 0.000 claims 1
230000023597 hemostasis Effects 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 15
238000011282 treatment Methods 0.000 abstract description 15
230000000694 effects Effects 0.000 abstract description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 6
201000010099 disease Diseases 0.000 abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
230000008569 process Effects 0.000 abstract description 3
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
102000007390 Glycogen Phosphorylase Human genes 0.000 abstract 2
108010046163 Glycogen Phosphorylase Proteins 0.000 abstract 2
125000005549 heteroarylene group Chemical group 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 88
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 56
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
239000000203 mixture Substances 0.000 description 42
238000004949 mass spectrometry Methods 0.000 description 40
125000005843 halogen group Chemical group 0.000 description 34
239000000243 solution Substances 0.000 description 34
235000019439 ethyl acetate Nutrition 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 29
238000005481 NMR spectroscopy Methods 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 25
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 25
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
125000003277 amino group Chemical group 0.000 description 24
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 23
239000000460 chlorine Substances 0.000 description 21
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
125000001424 substituent group Chemical group 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 20
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
150000001241 acetals Chemical class 0.000 description 18
239000008103 glucose Substances 0.000 description 18
229960001031 glucose Drugs 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
229920002527 Glycogen Polymers 0.000 description 17
229940096919 glycogen Drugs 0.000 description 17
239000002904 solvent Substances 0.000 description 17
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 16
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000012267 brine Substances 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
239000003039 volatile agent Substances 0.000 description 15
RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
101000876418 Homo sapiens Laforin Proteins 0.000 description 14
102100035192 Laforin Human genes 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000011737 fluorine Substances 0.000 description 13
229910052731 fluorine Inorganic materials 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000003112 inhibitor Substances 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
125000001153 fluoro group Chemical group F* 0.000 description 11
210000004185 liver Anatomy 0.000 description 11
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
238000003756 stirring Methods 0.000 description 10
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
238000003818 flash chromatography Methods 0.000 description 9
125000004125 inden-2-yl group Chemical group [H]C1=C(*)C([H])([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 9
239000000725 suspension Substances 0.000 description 9
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
150000001721 carbon Chemical group 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
206010012601 diabetes mellitus Diseases 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
239000007859 condensation product Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
UMLZCUKQMIDQJY-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=CN1 UMLZCUKQMIDQJY-UHFFFAOYSA-N 0.000 description 6
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000002585 base Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
229940088598 enzyme Drugs 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
238000009472 formulation Methods 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000003755 preservative agent Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
239000000872 buffer Substances 0.000 description 5
229910052681 coesite Inorganic materials 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
229910052906 cristobalite Inorganic materials 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
239000000796 flavoring agent Substances 0.000 description 5
235000013355 food flavoring agent Nutrition 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 5
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
229910052682 stishovite Inorganic materials 0.000 description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
229910052905 tridymite Inorganic materials 0.000 description 5
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 4
NQKAFZRPXBSHRX-UHFFFAOYSA-N 1H-pyrrole-2-carboximidamide hydrochloride Chemical compound Cl.NC(=N)C1=CC=CN1 NQKAFZRPXBSHRX-UHFFFAOYSA-N 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003086 colorant Substances 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000001715 oxadiazolyl group Chemical group 0.000 description 4
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000002953 preparative HPLC Methods 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
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