KR20240068583A

KR20240068583A - Lpa 수용체 길항제로서의 트리아졸-피리디닐 치환된 아자시클로헥실 아세트산 화합물

Lpa 수용체 길항제로서의 트리아졸-피리디닐 치환된 아자시클로헥실 아세트산 화합물 Download PDF

Info

Publication number: KR20240068583A
Authority: KR; South Korea
Prior art keywords: compound; alkyl; cycloalkyl; ring; substituted
Prior art date: 2020-08-11

Application number

KR1020237008152A

Other languages

English (en)

Korean (ko)

Inventor

홍지안 장

핑 첸

첸웨이 카이

페이 지앙

페이후아 선

Original Assignee

비바 스타 바이오사이언시스 리미티드

Priority date

2020-08-11

Filing date

2021-10-09

Publication date

2024-05-17

2021-10-09 Application filed by 비바 스타 바이오사이언시스 리미티드 filed Critical 비바 스타 바이오사이언시스 리미티드

2024-05-17 Publication of KR20240068583A publication Critical patent/KR20240068583A/ko

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102000004137 Lysophosphatidic Acid Receptors Human genes 0.000 title abstract description 10
108090000642 Lysophosphatidic Acid Receptors Proteins 0.000 title abstract description 10
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 title abstract 2
239000002464 receptor antagonist Substances 0.000 title 1
229940044551 receptor antagonist Drugs 0.000 title 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
201000010099 disease Diseases 0.000 claims abstract description 27
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
230000008482 dysregulation Effects 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 375
125000000217 alkyl group Chemical group 0.000 claims description 243
229910052739 hydrogen Inorganic materials 0.000 claims description 170
239000001257 hydrogen Substances 0.000 claims description 169
125000003545 alkoxy group Chemical group 0.000 claims description 147
229910052757 nitrogen Inorganic materials 0.000 claims description 122
150000002431 hydrogen Chemical class 0.000 claims description 117
125000000623 heterocyclic group Chemical group 0.000 claims description 108
229910052736 halogen Inorganic materials 0.000 claims description 92
150000002367 halogens Chemical class 0.000 claims description 92
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 83
229910052799 carbon Inorganic materials 0.000 claims description 75
125000005842 heteroatom Chemical group 0.000 claims description 74
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 68
229910052760 oxygen Inorganic materials 0.000 claims description 67
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 62
239000001301 oxygen Chemical group 0.000 claims description 62
229920006395 saturated elastomer Polymers 0.000 claims description 62
238000000034 method Methods 0.000 claims description 57
229910052717 sulfur Chemical group 0.000 claims description 53
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 51
125000004432 carbon atom Chemical group C* 0.000 claims description 51
239000011593 sulfur Chemical group 0.000 claims description 51
125000000753 cycloalkyl group Chemical group 0.000 claims description 45
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 45
150000003839 salts Chemical class 0.000 claims description 43
125000004433 nitrogen atom Chemical group N* 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
125000001072 heteroaryl group Chemical group 0.000 claims description 37
125000006413 ring segment Chemical group 0.000 claims description 36
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 34
125000003118 aryl group Chemical group 0.000 claims description 34
150000001721 carbon Chemical group 0.000 claims description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 24
125000003342 alkenyl group Chemical group 0.000 claims description 22
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
206010016654 Fibrosis Diseases 0.000 claims description 19
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
102100040607 Lysophosphatidic acid receptor 1 Human genes 0.000 claims description 15
230000004761 fibrosis Effects 0.000 claims description 14
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 12
206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 12
125000004043 oxo group Chemical group O=* 0.000 claims description 10
201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 9
208000036971 interstitial lung disease 2 Diseases 0.000 claims description 9
101710149745 Lysophosphatidic acid receptor 1 Proteins 0.000 claims description 8
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
210000004185 liver Anatomy 0.000 claims description 5
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
201000009594 Systemic Scleroderma Diseases 0.000 claims description 4
206010042953 Systemic sclerosis Diseases 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
208000020832 chronic kidney disease Diseases 0.000 claims description 4
208000033679 diabetic kidney disease Diseases 0.000 claims description 4
230000001575 pathological effect Effects 0.000 claims description 4
208000026594 alcoholic fatty liver disease Diseases 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
150000003018 phosphorus compounds Chemical class 0.000 claims 4
230000000747 cardiac effect Effects 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
230000002685 pulmonary effect Effects 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 17
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 abstract description 14
238000002360 preparation method Methods 0.000 abstract description 13
239000003814 drug Substances 0.000 abstract description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 274
239000000203 mixture Substances 0.000 description 266
-1 digluconate Chemical compound 0.000 description 184
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 143
235000019439 ethyl acetate Nutrition 0.000 description 137
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 132
238000000132 electrospray ionisation Methods 0.000 description 130
239000000243 solution Substances 0.000 description 119
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 115
239000011734 sodium Substances 0.000 description 87
239000012267 brine Substances 0.000 description 81
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 81
239000004698 Polyethylene Substances 0.000 description 69
239000007787 solid Substances 0.000 description 67
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
239000012299 nitrogen atmosphere Substances 0.000 description 60
238000003818 flash chromatography Methods 0.000 description 49
239000012044 organic layer Substances 0.000 description 47
238000005481 NMR spectroscopy Methods 0.000 description 46
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 45
235000002639 sodium chloride Nutrition 0.000 description 45
125000001424 substituent group Chemical group 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 40
239000003921 oil Substances 0.000 description 37
235000019198 oils Nutrition 0.000 description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 34
238000003786 synthesis reaction Methods 0.000 description 33
230000015572 biosynthetic process Effects 0.000 description 32
239000000651 prodrug Substances 0.000 description 30
229940002612 prodrug Drugs 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
KORIJXKQGMTQTO-UHFFFAOYSA-N 1h-pyrrol-2-ylmethanol Chemical class OCC1=CC=CN1 KORIJXKQGMTQTO-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000002585 base Substances 0.000 description 24
239000000706 filtrate Substances 0.000 description 23
238000010898 silica gel chromatography Methods 0.000 description 23
150000002148 esters Chemical class 0.000 description 22
230000002829 reductive effect Effects 0.000 description 21
125000004429 atom Chemical group 0.000 description 19
239000000126 substance Substances 0.000 description 19
239000003795 chemical substances by application Substances 0.000 description 18
239000000460 chlorine Substances 0.000 description 17
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 16
150000002168 ethanoic acid esters Chemical class 0.000 description 16
229910052698 phosphorus Inorganic materials 0.000 description 16
239000011574 phosphorus Substances 0.000 description 16
239000012230 colorless oil Substances 0.000 description 15
238000010511 deprotection reaction Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 13
125000005843 halogen group Chemical group 0.000 description 13
ICHCXRMAPXMSOZ-UHFFFAOYSA-N 5-propyl-1h-pyridin-2-one Chemical compound CCCC=1C=CC(=O)NC=1 ICHCXRMAPXMSOZ-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
125000000304 alkynyl group Chemical group 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
WRGQSWVCFNIUNZ-GDCKJWNLSA-N 1-oleoyl-sn-glycerol 3-phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O WRGQSWVCFNIUNZ-GDCKJWNLSA-N 0.000 description 11
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 11
150000001412 amines Chemical class 0.000 description 11
230000008901 benefit Effects 0.000 description 11
238000005516 engineering process Methods 0.000 description 11
239000012453 solvate Substances 0.000 description 11
208000024891 symptom Diseases 0.000 description 11
238000003419 tautomerization reaction Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 10
125000004122 cyclic group Chemical group 0.000 description 10
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 10
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
125000004452 carbocyclyl group Chemical group 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
230000001225 therapeutic effect Effects 0.000 description 9
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 8
229920000858 Cyclodextrin Polymers 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
238000009472 formulation Methods 0.000 description 8
238000001727 in vivo Methods 0.000 description 8
BCDBHIAXYFPJCT-UHFFFAOYSA-N methyl piperidine-3-carboxylate Chemical compound COC(=O)C1CCCNC1 BCDBHIAXYFPJCT-UHFFFAOYSA-N 0.000 description 8
QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 description 7
101000966782 Homo sapiens Lysophosphatidic acid receptor 1 Proteins 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
239000005457 ice water Substances 0.000 description 7
231100000252 nontoxic Toxicity 0.000 description 7
230000003000 nontoxic effect Effects 0.000 description 7
125000003367 polycyclic group Chemical group 0.000 description 7
238000002953 preparative HPLC Methods 0.000 description 7
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
210000001519 tissue Anatomy 0.000 description 7
DKBSTNARGKVRBG-UHFFFAOYSA-N 5-(cyclopropylmethyl)-2h-tetrazole Chemical compound N1=NNN=C1CC1CC1 DKBSTNARGKVRBG-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
230000009466 transformation Effects 0.000 description 6
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
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239000004480 active ingredient Substances 0.000 description 5
239000013543 active substance Substances 0.000 description 5
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125000001188 haloalkyl group Chemical group 0.000 description 5
150000004677 hydrates Chemical class 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
SUGXRJHYTSXVGY-LURJTMIESA-N methyl 2-[(3S)-5,5-difluoropiperidin-3-yl]acetate Chemical compound COC(C[C@@H](C1)CNCC1(F)F)=O SUGXRJHYTSXVGY-LURJTMIESA-N 0.000 description 5
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239000000725 suspension Substances 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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210000004072 lung Anatomy 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
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125000006574 non-aromatic ring group Chemical group 0.000 description 4
238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
150000003536 tetrazoles Chemical class 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
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125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 3
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