JP2004143134A

JP2004143134A - Ｊｎｋ阻害剤

Ｊｎｋ阻害剤 Download PDF

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Publication number: JP2004143134A
Authority: JP; Japan
Prior art keywords: group; phenyl; oxo; substituted; compound
Prior art date: 2002-02-13
Legal status : Withdrawn

Application number

JP2003035096A

Other languages

English (en)

Japanese (ja)

Other versions

JP2004143134A5 (enExample

Inventor

Fumio Ito

伊藤　文雄

Hiroyuki Kimura

木村　宏之

Hideki Igata

井形　英樹

Shuji Kitamura

北村　周治

Tomohiro Kawamoto

河本　朋広

Mitsuru Sasaki

佐々木　満

Current Assignee

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date

2002-02-13

Filing date

2003-02-13

Publication date

2004-05-20

2003-02-13 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

2003-02-13 Priority to JP2003035096A priority Critical patent/JP2004143134A/ja

2004-05-20 Publication of JP2004143134A publication Critical patent/JP2004143134A/ja

2006-03-23 Publication of JP2004143134A5 publication Critical patent/JP2004143134A5/ja

Status Withdrawn legal-status Critical Current

Links

239000012825 JNK inhibitor Substances 0.000 title claims description 13
229940118135 JNK inhibitor Drugs 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims abstract description 382
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 123
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 107
150000003839 salts Chemical class 0.000 claims abstract description 85
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 82
125000003277 amino group Chemical group 0.000 claims abstract description 61
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 56
239000003814 drug Substances 0.000 claims abstract description 49
108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 47
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 41
125000002252 acyl group Chemical group 0.000 claims abstract description 38
230000002401 inhibitory effect Effects 0.000 claims abstract description 13
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 11
-1 dimethylcarbamoyl group Chemical group 0.000 claims description 371
238000000034 method Methods 0.000 claims description 147
125000001424 substituent group Chemical group 0.000 claims description 120
125000005843 halogen group Chemical group 0.000 claims description 95
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 83
125000000217 alkyl group Chemical group 0.000 claims description 57
239000003795 chemical substances by application Substances 0.000 claims description 37
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical group C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 31
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
125000003396 thiol group Chemical group [H]S* 0.000 claims description 26
201000010099 disease Diseases 0.000 claims description 24
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 23
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
229910052799 carbon Inorganic materials 0.000 claims description 22
229940079593 drug Drugs 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 21
125000004076 pyridyl group Chemical group 0.000 claims description 20
241000124008 Mammalia Species 0.000 claims description 19
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 17
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
210000002216 heart Anatomy 0.000 claims description 16
201000004624 Dermatitis Diseases 0.000 claims description 15
230000001684 chronic effect Effects 0.000 claims description 15
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
206010007572 Cardiac hypertrophy Diseases 0.000 claims description 12
208000006029 Cardiomegaly Diseases 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
208000010125 myocardial infarction Diseases 0.000 claims description 12
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 12
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 12
229940124597 therapeutic agent Drugs 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
210000000056 organ Anatomy 0.000 claims description 11
238000004393 prognosis Methods 0.000 claims description 11
206010012601 diabetes mellitus Diseases 0.000 claims description 10
208000002551 irritable bowel syndrome Diseases 0.000 claims description 10
DIGCAHURJPAWKR-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 DIGCAHURJPAWKR-UHFFFAOYSA-N 0.000 claims description 10
208000009525 Myocarditis Diseases 0.000 claims description 9
208000006673 asthma Diseases 0.000 claims description 9
208000028867 ischemia Diseases 0.000 claims description 9
230000004770 neurodegeneration Effects 0.000 claims description 9
206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
238000002054 transplantation Methods 0.000 claims description 9
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
208000024827 Alzheimer disease Diseases 0.000 claims description 8
206010007556 Cardiac failure acute Diseases 0.000 claims description 8
206010007558 Cardiac failure chronic Diseases 0.000 claims description 8
208000031229 Cardiomyopathies Diseases 0.000 claims description 8
208000023105 Huntington disease Diseases 0.000 claims description 8
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
206010028980 Neoplasm Diseases 0.000 claims description 8
208000008589 Obesity Diseases 0.000 claims description 8
206010053159 Organ failure Diseases 0.000 claims description 8
208000018737 Parkinson disease Diseases 0.000 claims description 8
208000006011 Stroke Diseases 0.000 claims description 8
206010000891 acute myocardial infarction Diseases 0.000 claims description 8
201000011510 cancer Diseases 0.000 claims description 8
208000026106 cerebrovascular disease Diseases 0.000 claims description 8
210000003734 kidney Anatomy 0.000 claims description 8
201000008383 nephritis Diseases 0.000 claims description 8
208000015122 neurodegenerative disease Diseases 0.000 claims description 8
235000020824 obesity Nutrition 0.000 claims description 8
201000008482 osteoarthritis Diseases 0.000 claims description 8
208000033808 peripheral neuropathy Diseases 0.000 claims description 8
230000000069 prophylactic effect Effects 0.000 claims description 8
230000002792 vascular Effects 0.000 claims description 8
206010003210 Arteriosclerosis Diseases 0.000 claims description 7
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
206010009900 Colitis ulcerative Diseases 0.000 claims description 7
201000003883 Cystic fibrosis Diseases 0.000 claims description 7
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 7
208000032131 Diabetic Neuropathies Diseases 0.000 claims description 7
206010012689 Diabetic retinopathy Diseases 0.000 claims description 7
206010048554 Endothelial dysfunction Diseases 0.000 claims description 7
208000007882 Gastritis Diseases 0.000 claims description 7
201000005569 Gout Diseases 0.000 claims description 7
206010020772 Hypertension Diseases 0.000 claims description 7
206010030216 Oesophagitis Diseases 0.000 claims description 7
201000004681 Psoriasis Diseases 0.000 claims description 7
206010063837 Reperfusion injury Diseases 0.000 claims description 7
206010040070 Septic Shock Diseases 0.000 claims description 7
201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
230000001154 acute effect Effects 0.000 claims description 7
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 7
208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
208000010668 atopic eczema Diseases 0.000 claims description 7
210000004556 brain Anatomy 0.000 claims description 7
206010006451 bronchitis Diseases 0.000 claims description 7
208000033679 diabetic kidney disease Diseases 0.000 claims description 7
230000008694 endothelial dysfunction Effects 0.000 claims description 7
206010015037 epilepsy Diseases 0.000 claims description 7
208000006881 esophagitis Diseases 0.000 claims description 7
208000006454 hepatitis Diseases 0.000 claims description 7
231100000283 hepatitis Toxicity 0.000 claims description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
230000001969 hypertrophic effect Effects 0.000 claims description 7
208000012947 ischemia reperfusion injury Diseases 0.000 claims description 7
208000017169 kidney disease Diseases 0.000 claims description 7
210000004185 liver Anatomy 0.000 claims description 7
201000006417 multiple sclerosis Diseases 0.000 claims description 7
208000037803 restenosis Diseases 0.000 claims description 7
206010018364 Glomerulonephritis Diseases 0.000 claims description 6
238000002399 angioplasty Methods 0.000 claims description 6
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
ZQDJLYKWXSSYRN-UHFFFAOYSA-N methyl 6-bromo-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C3CCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 ZQDJLYKWXSSYRN-UHFFFAOYSA-N 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
208000020431 spinal cord injury Diseases 0.000 claims description 6
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 6
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 5
238000006880 cross-coupling reaction Methods 0.000 claims description 5
UJOQZQKRUNERFC-UHFFFAOYSA-N 4-[4-[(6-bromo-3-methoxycarbonyl-1-oxo-4-phenylisoquinolin-2-yl)methyl]anilino]-4-oxobutanoic acid Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(NC(=O)CCC(O)=O)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 UJOQZQKRUNERFC-UHFFFAOYSA-N 0.000 claims description 4
208000011231 Crohn disease Diseases 0.000 claims description 4
206010052337 Diastolic dysfunction Diseases 0.000 claims description 4
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
206010009887 colitis Diseases 0.000 claims description 4
LLZGJIRKICAIIZ-UHFFFAOYSA-N methyl 6-amino-2-(1,3-benzodioxol-5-ylmethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(N)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 LLZGJIRKICAIIZ-UHFFFAOYSA-N 0.000 claims description 4
NZWURHOBIFNZEW-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[(4-sulfamoylphenyl)methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)S(N)(=O)=O)C(C(=O)OC)=C1C1=CC=CC=C1 NZWURHOBIFNZEW-UHFFFAOYSA-N 0.000 claims description 4
WNTHBRVKPVTIQB-UHFFFAOYSA-N methyl 6-bromo-2-[(4-methylsulfonylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)S(C)(=O)=O)C(C(=O)OC)=C1C1=CC=CC=C1 WNTHBRVKPVTIQB-UHFFFAOYSA-N 0.000 claims description 4
230000003449 preventive effect Effects 0.000 claims description 4
229940002612 prodrug Drugs 0.000 claims description 4
239000000651 prodrug Substances 0.000 claims description 4
FWCBAZYAQITGCU-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-6-bromo-n,n-dimethyl-1-oxo-4-phenylisoquinoline-3-carboxamide Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)N(C)C)=C1C1=CC=CC=C1 FWCBAZYAQITGCU-UHFFFAOYSA-N 0.000 claims description 3
RXLLJFDBOVRCAP-VKAVYKQESA-N 3-[(z)-3-aminobut-2-enoyl]-6-bromo-2-[(4-methylsulfonylphenyl)methyl]-4-phenylisoquinolin-1-one Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)S(C)(=O)=O)C(C(=O)/C=C(N)/C)=C1C1=CC=CC=C1 RXLLJFDBOVRCAP-VKAVYKQESA-N 0.000 claims description 3
FDIFIDMDFPLLFI-PGMHBOJBSA-N 3-[(z)-3-aminopent-2-enoyl]-6-bromo-2-[(4-methylsulfonylphenyl)methyl]-4-phenylisoquinolin-1-one Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)S(C)(=O)=O)C(C(=O)/C=C(N)/CC)=C1C1=CC=CC=C1 FDIFIDMDFPLLFI-PGMHBOJBSA-N 0.000 claims description 3
ITAZALHTZBIKDO-UHFFFAOYSA-N 4-[(6-chloro-1-oxo-4-phenyl-3-propanoylisoquinolin-2-yl)methyl]benzoic acid Chemical compound C12=CC(Cl)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(O)=O)C(C(=O)CC)=C1C1=CC=CC=C1 ITAZALHTZBIKDO-UHFFFAOYSA-N 0.000 claims description 3
UQYHWHSKZWKHSN-UHFFFAOYSA-N 6-bromo-4-phenyl-3-propanoyl-2-[[4-(2h-tetrazol-5-yl)phenyl]methyl]isoquinolin-1-one Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C=2NN=NN=2)C(C(=O)CC)=C1C1=CC=CC=C1 UQYHWHSKZWKHSN-UHFFFAOYSA-N 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
208000027418 Wounds and injury Diseases 0.000 claims description 3
125000005605 benzo group Chemical group 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
230000006378 damage Effects 0.000 claims description 3
230000003205 diastolic effect Effects 0.000 claims description 3
CRIDCYDEDVRDGX-UHFFFAOYSA-N ethyl 6-chloro-2-(methylamino)-4-(4-methylphenyl)-1-oxoisoquinoline-3-carboxylate Chemical compound C12=CC(Cl)=CC=C2C(=O)N(NC)C(C(=O)OCC)=C1C1=CC=C(C)C=C1 CRIDCYDEDVRDGX-UHFFFAOYSA-N 0.000 claims description 3
208000014674 injury Diseases 0.000 claims description 3
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 3
208000037906 ischaemic injury Diseases 0.000 claims description 3
DPBRCSXYSMBYMA-UHFFFAOYSA-N methyl 2-[(1-acetylpiperidin-4-yl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2CCN(CC2)C(C)=O)C(C(=O)OC)=C1C1=CC=CC=C1 DPBRCSXYSMBYMA-UHFFFAOYSA-N 0.000 claims description 3
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 3
IEHGXDDKAMAZDO-UHFFFAOYSA-N methyl 6-bromo-2-(methylamino)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(NC)C(C(=O)OC)=C1C1=CC=CC=C1 IEHGXDDKAMAZDO-UHFFFAOYSA-N 0.000 claims description 3
LENYGJLWTMNGAI-UHFFFAOYSA-N methyl 6-chloro-2-(methylamino)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Cl)=CC=C2C(=O)N(NC)C(C(=O)OC)=C1C1=CC=CC=C1 LENYGJLWTMNGAI-UHFFFAOYSA-N 0.000 claims description 3
UCLSZKKUCRZQTL-UHFFFAOYSA-N methyl 6-fluoro-2-(methylamino)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(F)=CC=C2C(=O)N(NC)C(C(=O)OC)=C1C1=CC=CC=C1 UCLSZKKUCRZQTL-UHFFFAOYSA-N 0.000 claims description 3
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims description 3
KPKZHWXFCVFUOJ-UHFFFAOYSA-N s-pyridin-2-yl 6-bromo-2-[(4-methylsulfonylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carbothioate Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)SC1=CC=CC=N1 KPKZHWXFCVFUOJ-UHFFFAOYSA-N 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
FHSMWKZROYAQGA-UHFFFAOYSA-N 3-amino-2-(1,3-benzodioxol-5-ylmethyl)-6-bromo-4-phenylisoquinolin-1-one Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(N)=C1C1=CC=CC=C1 FHSMWKZROYAQGA-UHFFFAOYSA-N 0.000 claims description 2
230000009091 contractile dysfunction Effects 0.000 claims description 2
ZBCGBIZQNMVMPC-UHFFFAOYSA-N methyl isoquinoline-3-carboxylate Chemical compound C1=CC=C2C=NC(C(=O)OC)=CC2=C1 ZBCGBIZQNMVMPC-UHFFFAOYSA-N 0.000 claims description 2
VXCPIRQRAUFNFS-UHFFFAOYSA-N pyridin-3-ylmethyl 2-(1,3-benzodioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C=1C(Br)=CC=C(C(N(CC=2C=C3OCOC3=CC=2)C=2C(=O)OCC=3C=NC=CC=3)=O)C=1C=2C1=CC=CC=C1 VXCPIRQRAUFNFS-UHFFFAOYSA-N 0.000 claims description 2
230000010410 reperfusion Effects 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims 2
HJYFQTXVPCOFAH-UHFFFAOYSA-N 6-bromo-2-[(4-methylsulfonylphenyl)methyl]-4-phenyl-3-propanoylisoquinolin-1-one Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)S(C)(=O)=O)C(C(=O)CC)=C1C1=CC=CC=C1 HJYFQTXVPCOFAH-UHFFFAOYSA-N 0.000 claims 1
208000020339 Spinal injury Diseases 0.000 claims 1
150000001555 benzenes Chemical group 0.000 claims 1
239000000470 constituent Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 7
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 242
238000005160 1H NMR spectroscopy Methods 0.000 description 154
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
238000006243 chemical reaction Methods 0.000 description 126
239000000243 solution Substances 0.000 description 107
239000000203 mixture Substances 0.000 description 99
239000002904 solvent Substances 0.000 description 94
150000002430 hydrocarbons Chemical group 0.000 description 81
230000002829 reductive effect Effects 0.000 description 75
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
229910001868 water Inorganic materials 0.000 description 63
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
239000004215 Carbon black (E152) Substances 0.000 description 47
229930195733 hydrocarbon Natural products 0.000 description 47
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
239000002253 acid Substances 0.000 description 34
239000013078 crystal Substances 0.000 description 33
239000012044 organic layer Substances 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 31
239000002585 base Substances 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
229910052938 sodium sulfate Inorganic materials 0.000 description 28
235000011152 sodium sulphate Nutrition 0.000 description 28
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
125000003118 aryl group Chemical group 0.000 description 25
238000002360 preparation method Methods 0.000 description 25
238000010898 silica gel chromatography Methods 0.000 description 25
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
229910052794 bromium Inorganic materials 0.000 description 19
125000000753 cycloalkyl group Chemical group 0.000 description 19
239000000284 extract Substances 0.000 description 19
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PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
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RHMQZRGDGZQGRB-UHFFFAOYSA-N methyl 1-oxoisochromene-3-carboxylate Chemical compound C1=CC=C2C(=O)OC(C(=O)OC)=CC2=C1 RHMQZRGDGZQGRB-UHFFFAOYSA-N 0.000 description 1
RGIAGQWDEHVSJU-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-ylmethyl)-1-oxo-4,6-diphenylisoquinoline-3-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 RGIAGQWDEHVSJU-UHFFFAOYSA-N 0.000 description 1
LRVPFNALKHKWSG-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-ylmethyl)-1-oxo-4-phenyl-6-piperidin-1-ylisoquinoline-3-carboxylate Chemical compound C12=CC(N3CCCCC3)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 LRVPFNALKHKWSG-UHFFFAOYSA-N 0.000 description 1
KMFWWZFSPCFYFK-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-ylmethyl)-1-oxo-4-phenyl-6-thiophen-3-ylisoquinoline-3-carboxylate Chemical compound C12=CC(C3=CSC=C3)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 KMFWWZFSPCFYFK-UHFFFAOYSA-N 0.000 description 1
UPMPFDMYKCWRDX-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-ylmethyl)-6-cyano-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(C#N)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 UPMPFDMYKCWRDX-UHFFFAOYSA-N 0.000 description 1
KPVUBLJULYVDBH-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-ylmethyl)-6-morpholin-4-yl-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(N3CCOCC3)=CC=C2C(=O)N(CC=2C=C3OCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 KPVUBLJULYVDBH-UHFFFAOYSA-N 0.000 description 1
DIZIBVCQGYQFNP-UHFFFAOYSA-N methyl 2-(1-benzylpiperidin-4-yl)-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(C2CCN(CC=3C=CC=CC=3)CC2)C(C(=O)OC)=C1C1=CC=CC=C1 DIZIBVCQGYQFNP-UHFFFAOYSA-N 0.000 description 1
KWKYXNULEDEMKS-UHFFFAOYSA-N methyl 2-(1-benzylpyrrolidin-3-yl)-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(C2CN(CC=3C=CC=CC=3)CC2)C(C(=O)OC)=C1C1=CC=CC=C1 KWKYXNULEDEMKS-UHFFFAOYSA-N 0.000 description 1
JDKIBCSMXYUPNH-UHFFFAOYSA-N methyl 2-(1h-benzimidazol-2-ylmethyl)-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(Br)=CC=C2C(=O)N(CC=2NC3=CC=CC=C3N=2)C(C(=O)OC)=C1C1=CC=CC=C1 JDKIBCSMXYUPNH-UHFFFAOYSA-N 0.000 description 1
SFXDMJNMEMGKEA-UHFFFAOYSA-N methyl 2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC=CC=C2C(=O)N(CC=2C=C3CCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 SFXDMJNMEMGKEA-UHFFFAOYSA-N 0.000 description 1
GOMXRMBKFRRKKY-UHFFFAOYSA-N methyl 2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-6-fluoro-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(F)=CC=C2C(=O)N(CC=2C=C3CCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 GOMXRMBKFRRKKY-UHFFFAOYSA-N 0.000 description 1
KBIMBFVFMSWVBR-UHFFFAOYSA-N methyl 2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-6-methyl-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(C)=CC=C2C(=O)N(CC=2C=C3CCOC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 KBIMBFVFMSWVBR-UHFFFAOYSA-N 0.000 description 1
SAXZVSHGILPUPN-UHFFFAOYSA-N methyl 2-[(1-acetylpiperidin-3-yl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2CN(CCC2)C(C)=O)C(C(=O)OC)=C1C1=CC=CC=C1 SAXZVSHGILPUPN-UHFFFAOYSA-N 0.000 description 1
OHVWSYQCBNYIPH-UHFFFAOYSA-N methyl 2-[(3,5-dimethoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC=CC=C2C(=O)N(CC=2C=C(OC)C=C(OC)C=2)C(C(=O)OC)=C1C1=CC=CC=C1 OHVWSYQCBNYIPH-UHFFFAOYSA-N 0.000 description 1
PNKMPBBSMXKLHK-UHFFFAOYSA-N methyl 2-[(3-acetamidophenyl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(NC(C)=O)C=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 PNKMPBBSMXKLHK-UHFFFAOYSA-N 0.000 description 1
SMEYNZUXPIJHBV-UHFFFAOYSA-N methyl 2-[(3-aminophenyl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(N)C=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 SMEYNZUXPIJHBV-UHFFFAOYSA-N 0.000 description 1
CBQPPXLHVKBARM-UHFFFAOYSA-N methyl 2-[(3-benzoylphenyl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(C=CC=2)C(=O)C=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 CBQPPXLHVKBARM-UHFFFAOYSA-N 0.000 description 1
QAMKUCUNPCSENQ-UHFFFAOYSA-N methyl 2-[(4-acetamidophenyl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(NC(C)=O)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 QAMKUCUNPCSENQ-UHFFFAOYSA-N 0.000 description 1
QCTGONDFZARDIP-UHFFFAOYSA-N methyl 2-[(4-aminophenyl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(N)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 QCTGONDFZARDIP-UHFFFAOYSA-N 0.000 description 1
MREGDKHRVBWCJM-UHFFFAOYSA-N methyl 2-[(4-benzoylphenyl)methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 MREGDKHRVBWCJM-UHFFFAOYSA-N 0.000 description 1
CPRGOFXAMJCARC-UHFFFAOYSA-N methyl 2-[[4-(anilinocarbamoyl)phenyl]methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NNC=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 CPRGOFXAMJCARC-UHFFFAOYSA-N 0.000 description 1
PVAOVCSYKMCAOK-UHFFFAOYSA-N methyl 2-[[4-[(2-amino-2-oxoethyl)carbamoyl]phenyl]methyl]-6-bromo-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NCC(N)=O)C(C(=O)OC)=C1C1=CC=CC=C1 PVAOVCSYKMCAOK-UHFFFAOYSA-N 0.000 description 1
KSGMMDKLKBRUDD-UHFFFAOYSA-N methyl 2-acetamido-6-chloro-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Cl)=CC=C2C(=O)N(NC(C)=O)C(C(=O)OC)=C1C1=CC=CC=C1 KSGMMDKLKBRUDD-UHFFFAOYSA-N 0.000 description 1
SAPBUESGEIOEEX-UHFFFAOYSA-N methyl 2-benzyl-6-chloro-1-oxo-4-(trifluoromethylsulfonyloxy)isoquinoline-3-carboxylate Chemical compound COC(=O)C1=C(OS(=O)(=O)C(F)(F)F)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=CC=C1 SAPBUESGEIOEEX-UHFFFAOYSA-N 0.000 description 1
XOJQBAGQVLYFIL-UHFFFAOYSA-N methyl 2-benzyl-6-chloro-4-hydroxy-1-oxoisoquinoline-3-carboxylate Chemical compound COC(=O)C1=C(O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=CC=C1 XOJQBAGQVLYFIL-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
YUHSMQQNPRLEEJ-UHFFFAOYSA-N methyl 3-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CBr)=C1 YUHSMQQNPRLEEJ-UHFFFAOYSA-N 0.000 description 1
AQBJGAUQEJFPKZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1 AQBJGAUQEJFPKZ-UHFFFAOYSA-N 0.000 description 1
GIZCKBSSWNIUMZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=C(CN)C=C1 GIZCKBSSWNIUMZ-UHFFFAOYSA-N 0.000 description 1
QXNBGOCQIUFHQK-UHFFFAOYSA-N methyl 4-[(2-hydroxypropylamino)methyl]benzoate Chemical compound COC(=O)C1=CC=C(CNCC(C)O)C=C1 QXNBGOCQIUFHQK-UHFFFAOYSA-N 0.000 description 1
SIKOJEOBOAEPRA-UHFFFAOYSA-N methyl 6-bromo-1-oxo-2-[(3-phenoxyphenyl)methyl]-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 SIKOJEOBOAEPRA-UHFFFAOYSA-N 0.000 description 1
WOEBPFXZKGLREP-UHFFFAOYSA-N methyl 6-bromo-1-oxo-2-[(4-phenoxyphenyl)methyl]-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 WOEBPFXZKGLREP-UHFFFAOYSA-N 0.000 description 1
NUTYTIOJRXYPDD-UHFFFAOYSA-N methyl 6-bromo-1-oxo-2-phenacyl-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC(=O)C=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 NUTYTIOJRXYPDD-UHFFFAOYSA-N 0.000 description 1
KSVQPLSXCCTHHN-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(1,2,3,4-tetrahydronaphthalen-1-yl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(C2C3=CC=CC=C3CCC2)C(C(=O)OC)=C1C1=CC=CC=C1 KSVQPLSXCCTHHN-UHFFFAOYSA-N 0.000 description 1
ZOFHUXAVTODYBY-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(1,3-thiazol-4-ylmethyl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2N=CSC=2)C(C(=O)OC)=C1C1=CC=CC=C1 ZOFHUXAVTODYBY-UHFFFAOYSA-N 0.000 description 1
TYDYCTBAGNDVCZ-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(1-phenylethyl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(C(C)C=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 TYDYCTBAGNDVCZ-UHFFFAOYSA-N 0.000 description 1
ZENAMHIXXPKHSQ-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(2-phenylethyl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CCC=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 ZENAMHIXXPKHSQ-UHFFFAOYSA-N 0.000 description 1
DOQRPWCYSAVGDC-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(3-phenylpropyl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CCCC=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 DOQRPWCYSAVGDC-UHFFFAOYSA-N 0.000 description 1
SXRVKZRWDONXCF-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(pyridin-2-ylmethyl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2N=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 SXRVKZRWDONXCF-UHFFFAOYSA-N 0.000 description 1
WMKCYQMFZUQSCP-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(pyridin-4-ylmethyl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CN=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 WMKCYQMFZUQSCP-UHFFFAOYSA-N 0.000 description 1
LTRKNDWOOKVGCP-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(quinolin-2-ylmethyl)isoquinoline-3-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(Br)=CC=C2C(=O)N(CC=2N=C3C=CC=CC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 LTRKNDWOOKVGCP-UHFFFAOYSA-N 0.000 description 1
QAEIIIGPVKFYFQ-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-(thiophen-2-ylmethyl)isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2SC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 QAEIIIGPVKFYFQ-UHFFFAOYSA-N 0.000 description 1
BXDVACRTSGSQDW-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[(2-phenylphenyl)methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=CC=2)C=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 BXDVACRTSGSQDW-UHFFFAOYSA-N 0.000 description 1
IZNPQJGRLXTLOD-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[(3,4,5-trimethoxyphenyl)methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(OC)C(OC)=C(OC)C=2)C(C(=O)OC)=C1C1=CC=CC=C1 IZNPQJGRLXTLOD-UHFFFAOYSA-N 0.000 description 1
OMFPAYPHIYOXBG-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[(4-phenylphenyl)methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 OMFPAYPHIYOXBG-UHFFFAOYSA-N 0.000 description 1
KTRJLJHTGMWYJC-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[2-(trifluoromethyl)phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=CC=2)C(F)(F)F)C(C(=O)OC)=C1C1=CC=CC=C1 KTRJLJHTGMWYJC-UHFFFAOYSA-N 0.000 description 1
QACRZFSGBDBHBG-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[3-(trifluoromethyl)phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(C=CC=2)C(F)(F)F)C(C(=O)OC)=C1C1=CC=CC=C1 QACRZFSGBDBHBG-UHFFFAOYSA-N 0.000 description 1
UUNFBBZOPYXAHK-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[4-(2-pyrrolidin-1-ylethylcarbamoyl)phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NCCN2CCCC2)C(C(=O)OC)=C1C1=CC=CC=C1 UUNFBBZOPYXAHK-UHFFFAOYSA-N 0.000 description 1
QEMPVEUPWHFRLV-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[4-(piperidin-1-ylcarbamoyl)phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NN2CCCCC2)C(C(=O)OC)=C1C1=CC=CC=C1 QEMPVEUPWHFRLV-UHFFFAOYSA-N 0.000 description 1
LAFRLWSMAHXMRO-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[4-(pyrrolidin-1-ylcarbamoyl)phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NN2CCCC2)C(C(=O)OC)=C1C1=CC=CC=C1 LAFRLWSMAHXMRO-UHFFFAOYSA-N 0.000 description 1
PTOOXTNIKOSJBL-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[4-(trifluoromethoxy)phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(OC(F)(F)F)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 PTOOXTNIKOSJBL-UHFFFAOYSA-N 0.000 description 1
XSNWTDHIJBCLCQ-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[4-(trifluoromethyl)phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(F)(F)F)C(C(=O)OC)=C1C1=CC=CC=C1 XSNWTDHIJBCLCQ-UHFFFAOYSA-N 0.000 description 1
GGAXGKSVJHVELC-UHFFFAOYSA-N methyl 6-bromo-1-oxo-4-phenyl-2-[[4-[(pyridin-2-ylamino)carbamoyl]phenyl]methyl]isoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NNC=2N=CC=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 GGAXGKSVJHVELC-UHFFFAOYSA-N 0.000 description 1
BKVIKYGQTIAZTH-UHFFFAOYSA-N methyl 6-bromo-2-(2,3-dihydro-1h-inden-1-yl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(C2C3=CC=CC=C3CC2)C(C(=O)OC)=C1C1=CC=CC=C1 BKVIKYGQTIAZTH-UHFFFAOYSA-N 0.000 description 1
DJRKVWXQKLEWAX-UHFFFAOYSA-N methyl 6-bromo-2-(2,3-dihydro-1h-inden-2-yl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(C2CC3=CC=CC=C3C2)C(C(=O)OC)=C1C1=CC=CC=C1 DJRKVWXQKLEWAX-UHFFFAOYSA-N 0.000 description 1
LEBZMADSLZDLBM-UHFFFAOYSA-N methyl 6-bromo-2-(2-methoxy-2-oxo-1-phenylethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound COC(=O)C1=C(C=2C=CC=CC=2)C2=CC(Br)=CC=C2C(=O)N1C(C(=O)OC)C1=CC=CC=C1 LEBZMADSLZDLBM-UHFFFAOYSA-N 0.000 description 1
JUSHXNYASDHRPF-UHFFFAOYSA-N methyl 6-bromo-2-(2-methoxyethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CCOC)C(C(=O)OC)=C1C1=CC=CC=C1 JUSHXNYASDHRPF-UHFFFAOYSA-N 0.000 description 1
APSWQJGGHYCBBK-UHFFFAOYSA-N methyl 6-bromo-2-(cyclohexylmethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2CCCCC2)C(C(=O)OC)=C1C1=CC=CC=C1 APSWQJGGHYCBBK-UHFFFAOYSA-N 0.000 description 1
RTLWAFGLGUYUEM-UHFFFAOYSA-N methyl 6-bromo-2-(cyclopropylmethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2CC2)C(C(=O)OC)=C1C1=CC=CC=C1 RTLWAFGLGUYUEM-UHFFFAOYSA-N 0.000 description 1
TVLHRUOYSWFCQT-UHFFFAOYSA-N methyl 6-bromo-2-(naphthalen-1-ylmethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C3=CC=CC=C3C=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 TVLHRUOYSWFCQT-UHFFFAOYSA-N 0.000 description 1
FVGRUOVFSKCTOC-UHFFFAOYSA-N methyl 6-bromo-2-(naphthalen-2-ylmethyl)-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C3C=CC=CC3=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 FVGRUOVFSKCTOC-UHFFFAOYSA-N 0.000 description 1
SFPPAGMVBOSNBQ-UHFFFAOYSA-N methyl 6-bromo-2-[(1-methylsulfonylpiperidin-4-yl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2CCN(CC2)S(C)(=O)=O)C(C(=O)OC)=C1C1=CC=CC=C1 SFPPAGMVBOSNBQ-UHFFFAOYSA-N 0.000 description 1
RHNORHULDIIOHI-UHFFFAOYSA-N methyl 6-bromo-2-[(2,3-dimethoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=C(OC)C=CC=2)OC)C(C(=O)OC)=C1C1=CC=CC=C1 RHNORHULDIIOHI-UHFFFAOYSA-N 0.000 description 1
XSRNTJAGEDGYPZ-UHFFFAOYSA-N methyl 6-bromo-2-[(2,4-difluorophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC(F)=CC=2)F)C(C(=O)OC)=C1C1=CC=CC=C1 XSRNTJAGEDGYPZ-UHFFFAOYSA-N 0.000 description 1
IFJLZYAKXNMLHK-UHFFFAOYSA-N methyl 6-bromo-2-[(2,4-dimethoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC(OC)=CC=2)OC)C(C(=O)OC)=C1C1=CC=CC=C1 IFJLZYAKXNMLHK-UHFFFAOYSA-N 0.000 description 1
FAGMTZCMBMHTNU-UHFFFAOYSA-N methyl 6-bromo-2-[(2,5-dimethoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=C(OC)C=2)OC)C(C(=O)OC)=C1C1=CC=CC=C1 FAGMTZCMBMHTNU-UHFFFAOYSA-N 0.000 description 1
HZDWBAWIHMRBPE-UHFFFAOYSA-N methyl 6-bromo-2-[(2,6-difluorophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=CC=2F)F)C(C(=O)OC)=C1C1=CC=CC=C1 HZDWBAWIHMRBPE-UHFFFAOYSA-N 0.000 description 1
ONWPZUBYDSAIJE-UHFFFAOYSA-N methyl 6-bromo-2-[(2-chlorophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=CC=2)Cl)C(C(=O)OC)=C1C1=CC=CC=C1 ONWPZUBYDSAIJE-UHFFFAOYSA-N 0.000 description 1
FXSXFGVWHFAMCW-UHFFFAOYSA-N methyl 6-bromo-2-[(2-methoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=CC=2)OC)C(C(=O)OC)=C1C1=CC=CC=C1 FXSXFGVWHFAMCW-UHFFFAOYSA-N 0.000 description 1
UBFTUXBAHQVLIZ-UHFFFAOYSA-N methyl 6-bromo-2-[(2-methylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=CC=2)C)C(C(=O)OC)=C1C1=CC=CC=C1 UBFTUXBAHQVLIZ-UHFFFAOYSA-N 0.000 description 1
QLIBEHHZFDNYEJ-UHFFFAOYSA-N methyl 6-bromo-2-[(2-nitrophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=CC=2)[N+]([O-])=O)C(C(=O)OC)=C1C1=CC=CC=C1 QLIBEHHZFDNYEJ-UHFFFAOYSA-N 0.000 description 1
HNQUOKNJZUBDBS-UHFFFAOYSA-N methyl 6-bromo-2-[(3,4-dichlorophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(Cl)C(Cl)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 HNQUOKNJZUBDBS-UHFFFAOYSA-N 0.000 description 1
VPIJDZKNMOMAOV-UHFFFAOYSA-N methyl 6-bromo-2-[(3,4-dimethoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(OC)C(OC)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 VPIJDZKNMOMAOV-UHFFFAOYSA-N 0.000 description 1
JQOYFPILFRDRTI-UHFFFAOYSA-N methyl 6-bromo-2-[(3,4-dimethylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(C)C(C)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 JQOYFPILFRDRTI-UHFFFAOYSA-N 0.000 description 1
TWWYLRRDAAMWJV-UHFFFAOYSA-N methyl 6-bromo-2-[(3,5-difluorophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(F)C=C(F)C=2)C(C(=O)OC)=C1C1=CC=CC=C1 TWWYLRRDAAMWJV-UHFFFAOYSA-N 0.000 description 1
ODZWJROQIKUBNP-UHFFFAOYSA-N methyl 6-bromo-2-[(3,5-dimethoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(OC)C=C(OC)C=2)C(C(=O)OC)=C1C1=CC=CC=C1 ODZWJROQIKUBNP-UHFFFAOYSA-N 0.000 description 1
XVCPSGOYZBFBJC-UHFFFAOYSA-N methyl 6-bromo-2-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2=C(ON=C2C)C)C(C(=O)OC)=C1C1=CC=CC=C1 XVCPSGOYZBFBJC-UHFFFAOYSA-N 0.000 description 1
HQOLCXPGCFPFLN-UHFFFAOYSA-N methyl 6-bromo-2-[(3-bromophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(Br)C=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 HQOLCXPGCFPFLN-UHFFFAOYSA-N 0.000 description 1
QRRBAPHSDIHEHE-UHFFFAOYSA-N methyl 6-bromo-2-[(3-fluorophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(F)C=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 QRRBAPHSDIHEHE-UHFFFAOYSA-N 0.000 description 1
RIYORDYQDFBEES-UHFFFAOYSA-N methyl 6-bromo-2-[(3-methoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(OC)C=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 RIYORDYQDFBEES-UHFFFAOYSA-N 0.000 description 1
GOCQWZSQAAINTO-UHFFFAOYSA-N methyl 6-bromo-2-[(3-nitrophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=C(C=CC=2)[N+]([O-])=O)C(C(=O)OC)=C1C1=CC=CC=C1 GOCQWZSQAAINTO-UHFFFAOYSA-N 0.000 description 1
YVDLEYJPZHANQT-UHFFFAOYSA-N methyl 6-bromo-2-[(4-cyanophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C#N)C(C(=O)OC)=C1C1=CC=CC=C1 YVDLEYJPZHANQT-UHFFFAOYSA-N 0.000 description 1
QONFRCNRSNHYPV-UHFFFAOYSA-N methyl 6-bromo-2-[(4-fluorophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(F)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 QONFRCNRSNHYPV-UHFFFAOYSA-N 0.000 description 1
XDGGUKJAPTZLOW-UHFFFAOYSA-N methyl 6-bromo-2-[(4-methoxycarbonylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC XDGGUKJAPTZLOW-UHFFFAOYSA-N 0.000 description 1
WCVSMBLDSVHGLZ-UHFFFAOYSA-N methyl 6-bromo-2-[(4-methoxyphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(OC)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 WCVSMBLDSVHGLZ-UHFFFAOYSA-N 0.000 description 1
FJVQXKCWSGLRHH-UHFFFAOYSA-N methyl 6-bromo-2-[(4-methylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(C)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 FJVQXKCWSGLRHH-UHFFFAOYSA-N 0.000 description 1
NTCHPSHOSMCROC-UHFFFAOYSA-N methyl 6-bromo-2-[(4-nitrophenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)[N+]([O-])=O)C(C(=O)OC)=C1C1=CC=CC=C1 NTCHPSHOSMCROC-UHFFFAOYSA-N 0.000 description 1
OISMKMHBMHQLBS-UHFFFAOYSA-N methyl 6-bromo-2-[(4-tert-butylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(C)(C)C)C(C(=O)OC)=C1C1=CC=CC=C1 OISMKMHBMHQLBS-UHFFFAOYSA-N 0.000 description 1
UIDQJYKWPSRKFE-UHFFFAOYSA-N methyl 6-bromo-2-[(5-methylpyrazin-2-yl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2N=CC(C)=NC=2)C(C(=O)OC)=C1C1=CC=CC=C1 UIDQJYKWPSRKFE-UHFFFAOYSA-N 0.000 description 1
OWYYMGIDCGOXMY-UHFFFAOYSA-N methyl 6-bromo-2-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C(=CC=3OCOC=3C=2)Br)C(C(=O)OC)=C1C1=CC=CC=C1 OWYYMGIDCGOXMY-UHFFFAOYSA-N 0.000 description 1
BIRWREOSLQNTNM-UHFFFAOYSA-N methyl 6-bromo-2-[2-(4-chlorophenyl)-2-oxoethyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC(=O)C=2C=CC(Cl)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 BIRWREOSLQNTNM-UHFFFAOYSA-N 0.000 description 1
HCBZANGSBPYDLJ-UHFFFAOYSA-N methyl 6-bromo-2-[2-(4-cyanophenyl)-2-oxoethyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC(=O)C=2C=CC(=CC=2)C#N)C(C(=O)OC)=C1C1=CC=CC=C1 HCBZANGSBPYDLJ-UHFFFAOYSA-N 0.000 description 1
DFCNFIHMAYMTCX-UHFFFAOYSA-N methyl 6-bromo-2-[2-(4-methoxyphenyl)-2-oxoethyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC(=O)C=2C=CC(OC)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 DFCNFIHMAYMTCX-UHFFFAOYSA-N 0.000 description 1
ASZAIGDGEUVDDS-UHFFFAOYSA-N methyl 6-bromo-2-[2-(4-nitrophenyl)-2-oxoethyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC(=O)C=2C=CC(=CC=2)[N+]([O-])=O)C(C(=O)OC)=C1C1=CC=CC=C1 ASZAIGDGEUVDDS-UHFFFAOYSA-N 0.000 description 1
ZXNZKRYCAXDNFB-UHFFFAOYSA-N methyl 6-bromo-2-[[1-(methylcarbamoyl)piperidin-4-yl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1CN(C(=O)NC)CCC1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC ZXNZKRYCAXDNFB-UHFFFAOYSA-N 0.000 description 1
GFHRNOAHLAOBID-UHFFFAOYSA-N methyl 6-bromo-2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-3-yl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2CN(CCC2)C(=O)OC(C)(C)C)C(C(=O)OC)=C1C1=CC=CC=C1 GFHRNOAHLAOBID-UHFFFAOYSA-N 0.000 description 1
DDJLXKIVXJXKCS-UHFFFAOYSA-N methyl 6-bromo-2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)OC)=C1C1=CC=CC=C1 DDJLXKIVXJXKCS-UHFFFAOYSA-N 0.000 description 1
KOUYFUKSAITVCP-UHFFFAOYSA-N methyl 6-bromo-2-[[3-(methylcarbamoylamino)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound CNC(=O)NC1=CC=CC(CN2C(C3=CC=C(Br)C=C3C(C=3C=CC=CC=3)=C2C(=O)OC)=O)=C1 KOUYFUKSAITVCP-UHFFFAOYSA-N 0.000 description 1
GAWJXOGCILIJLO-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(2-hydroxyethylcarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NCCO)C(C(=O)OC)=C1C1=CC=CC=C1 GAWJXOGCILIJLO-UHFFFAOYSA-N 0.000 description 1
VWCIPAFRGTVVQB-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(2-hydroxypropylcarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NCC(C)O)C(C(=O)OC)=C1C1=CC=CC=C1 VWCIPAFRGTVVQB-UHFFFAOYSA-N 0.000 description 1
RXVZVPYGRDZUGN-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(2-methoxyethylcarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)NCCOC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC RXVZVPYGRDZUGN-UHFFFAOYSA-N 0.000 description 1
XQSCTOMYBBLOCT-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(3-methoxypropylcarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)NCCCOC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC XQSCTOMYBBLOCT-UHFFFAOYSA-N 0.000 description 1
GZQWTBWBVYWSTL-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(4-chlorobenzoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)C=2C=CC(Cl)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 GZQWTBWBVYWSTL-UHFFFAOYSA-N 0.000 description 1
PTJQLCHIYAXCKU-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(dimethylaminocarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NN(C)C)C(C(=O)OC)=C1C1=CC=CC=C1 PTJQLCHIYAXCKU-UHFFFAOYSA-N 0.000 description 1
DJXJHLBJOTZRMV-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(dimethylcarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)N(C)C)C(C(=O)OC)=C1C1=CC=CC=C1 DJXJHLBJOTZRMV-UHFFFAOYSA-N 0.000 description 1
XWCIUTKOPBHKSM-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(methoxycarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)NOC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC XWCIUTKOPBHKSM-UHFFFAOYSA-N 0.000 description 1
BOZPMZCDKGCPKP-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(methylcarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)NC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC BOZPMZCDKGCPKP-UHFFFAOYSA-N 0.000 description 1
CIOITXHCVDUNJQ-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(methylcarbamoylamino)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(NC(=O)NC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC CIOITXHCVDUNJQ-UHFFFAOYSA-N 0.000 description 1
RDWCLAUKUOXYHS-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(morpholin-4-ylcarbamoyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NN2CCOCC2)C(C(=O)OC)=C1C1=CC=CC=C1 RDWCLAUKUOXYHS-UHFFFAOYSA-N 0.000 description 1
RRGVTPFCLJPCQS-UHFFFAOYSA-N methyl 6-bromo-2-[[4-(morpholine-4-carbonyl)phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)N2CCOCC2)C(C(=O)OC)=C1C1=CC=CC=C1 RRGVTPFCLJPCQS-UHFFFAOYSA-N 0.000 description 1
DTEGGTVIFZAVBT-UHFFFAOYSA-N methyl 6-bromo-2-[[4-[(4-fluoroanilino)carbamoyl]phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NNC=2C=CC(F)=CC=2)C(C(=O)OC)=C1C1=CC=CC=C1 DTEGGTVIFZAVBT-UHFFFAOYSA-N 0.000 description 1
HVFRJCYJMXBZNP-UHFFFAOYSA-N methyl 6-bromo-2-[[4-[(4-methoxy-4-oxobutyl)carbamoyl]phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)NCCCC(=O)OC)=CC=C1CN1C(=O)C2=CC=C(Br)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC HVFRJCYJMXBZNP-UHFFFAOYSA-N 0.000 description 1
HXZINGOOOJSYNI-UHFFFAOYSA-N methyl 6-bromo-2-[[4-[2-(dimethylamino)ethylcarbamoyl]phenyl]methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CC=2C=CC(=CC=2)C(=O)NCCN(C)C)C(C(=O)OC)=C1C1=CC=CC=C1 HXZINGOOOJSYNI-UHFFFAOYSA-N 0.000 description 1
CTKGDQRCSYADAX-UHFFFAOYSA-N methyl 6-bromo-2-butyl-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C12=CC(Br)=CC=C2C(=O)N(CCCC)C(C(=O)OC)=C1C1=CC=CC=C1 CTKGDQRCSYADAX-UHFFFAOYSA-N 0.000 description 1
DVNLDUWMRKCXLO-UHFFFAOYSA-N methyl 6-chloro-2-[(4-methoxycarbonylphenyl)methyl]-1-oxo-4-(trifluoromethylsulfonyloxy)isoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)C2=CC=C(Cl)C=C2C(OS(=O)(=O)C(F)(F)F)=C1C(=O)OC DVNLDUWMRKCXLO-UHFFFAOYSA-N 0.000 description 1
JBYIUGOGDSVHFA-UHFFFAOYSA-N methyl 6-chloro-2-[(4-methoxycarbonylphenyl)methyl]-1-oxo-4-phenylisoquinoline-3-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)C2=CC=C(Cl)C=C2C(C=2C=CC=CC=2)=C1C(=O)OC JBYIUGOGDSVHFA-UHFFFAOYSA-N 0.000 description 1
JIULVWOZXVZMEL-UHFFFAOYSA-N methyl 6-chloro-2-[(4-methylsulfonylphenyl)methyl]-1-oxo-4-(trifluoromethylsulfonyloxy)isoquinoline-3-carboxylate Chemical compound COC(=O)C1=C(OS(=O)(=O)C(F)(F)F)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(S(C)(=O)=O)C=C1 JIULVWOZXVZMEL-UHFFFAOYSA-N 0.000 description 1
125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
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IYJMSDVSVHDVGT-PEQKVOOWSA-N metildigoxin Chemical compound O1[C@H](C)[C@@H](OC)[C@@H](O)C[C@@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O IYJMSDVSVHDVGT-PEQKVOOWSA-N 0.000 description 1
229960003746 metildigoxin Drugs 0.000 description 1
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
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229960003574 milrinone Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
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125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 1
229960004255 nadolol Drugs 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
230000003955 neuronal function Effects 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007135 neurotoxicity Effects 0.000 description 1
231100000228 neurotoxicity Toxicity 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229960001783 nicardipine Drugs 0.000 description 1
MWMOHAMAKRKDLU-UHFFFAOYSA-N nickel;triethylphosphane Chemical compound [Ni].CCP(CC)CC.CCP(CC)CC MWMOHAMAKRKDLU-UHFFFAOYSA-N 0.000 description 1
KFBKRCXOTTUAFS-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 KFBKRCXOTTUAFS-UHFFFAOYSA-N 0.000 description 1
UYLRKRLDQUXYKB-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UYLRKRLDQUXYKB-UHFFFAOYSA-N 0.000 description 1
KJWGEXJCWCYEMI-UHFFFAOYSA-N nilvadipine Chemical compound COC(=O)C1=C(C#N)N=C(C)C(C(=O)OC(C)C)C1C1=CC=CC(N(=O)=O)=C1 KJWGEXJCWCYEMI-UHFFFAOYSA-N 0.000 description 1
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230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
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239000002736 nonionic surfactant Substances 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229950005421 olprinone Drugs 0.000 description 1
230000033667 organ regeneration Effects 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
229960002739 oxaprozin Drugs 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000003566 oxetanyl group Chemical group 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
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125000004430 oxygen atom Chemical group O* 0.000 description 1
229960005118 oxymorphone Drugs 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
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