JP2014530238A5 - - Google Patents
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- Publication number
- JP2014530238A5 JP2014530238A5 JP2014535869A JP2014535869A JP2014530238A5 JP 2014530238 A5 JP2014530238 A5 JP 2014530238A5 JP 2014535869 A JP2014535869 A JP 2014535869A JP 2014535869 A JP2014535869 A JP 2014535869A JP 2014530238 A5 JP2014530238 A5 JP 2014530238A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dec
- ylcarbamoyl
- benzothiazol
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 heterocyclic alkane Chemical class 0.000 claims description 122
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 229910004013 NO 2 Inorganic materials 0.000 claims description 36
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims description 30
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 229910052740 iodine Inorganic materials 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 150000001924 cycloalkanes Chemical class 0.000 claims description 18
- 150000001925 cycloalkenes Chemical class 0.000 claims description 18
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 6
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 201000000050 myeloid neoplasm Diseases 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 206010005003 Bladder cancer Diseases 0.000 claims 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- 101100240521 Caenorhabditis elegans nhr-16 gene Proteins 0.000 claims 3
- 206010008342 Cervix carcinoma Diseases 0.000 claims 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 3
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 3
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 3
- 206010033128 Ovarian cancer Diseases 0.000 claims 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 3
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 206010041067 Small cell lung cancer Diseases 0.000 claims 3
- 208000000277 Splenic Neoplasms Diseases 0.000 claims 3
- 210000001744 T-lymphocyte Anatomy 0.000 claims 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 3
- 210000003719 b-lymphocyte Anatomy 0.000 claims 3
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 3
- 201000006491 bone marrow cancer Diseases 0.000 claims 3
- 201000010881 cervical cancer Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 201000004101 esophageal cancer Diseases 0.000 claims 3
- 201000003444 follicular lymphoma Diseases 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 3
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims 3
- 208000003747 lymphoid leukemia Diseases 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 208000025113 myeloid leukemia Diseases 0.000 claims 3
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 3
- 201000002471 spleen cancer Diseases 0.000 claims 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- WMXKKYYYZPZSJA-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-3,5-dimethylpyrazol-4-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(C)N(CC45CC6CC(CC(C6)C4)C5)N=C3C)=NC2=C1 WMXKKYYYZPZSJA-UHFFFAOYSA-N 0.000 claims 1
- DPXXHOZGVBDFCX-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-cyano-2-methylpyrrol-3-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(C(C#N)=C3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 DPXXHOZGVBDFCX-UHFFFAOYSA-N 0.000 claims 1
- NKMWBPIMEXAUCU-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1C(C2)CC(C3)CC2CC13CN1N=CC(C2=CC=C(N=C2C(O)=O)N2C(C3=C(C(=O)NC=4SC5=CC=CC=C5N=4)C=CC=C3CC2)C)=C1C NKMWBPIMEXAUCU-UHFFFAOYSA-N 0.000 claims 1
- QCQQONWEDCOTBV-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 QCQQONWEDCOTBV-UHFFFAOYSA-N 0.000 claims 1
- XQWAUHSNIXVETH-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-4,4-dimethyl-1,3-dihydroisoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C3=C4CN(CC(C)(C)C4=CC=C3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 XQWAUHSNIXVETH-UHFFFAOYSA-N 0.000 claims 1
- SRYPCRRVZAWVJL-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-([1,3]thiazolo[4,5-b]pyridin-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=N1 SRYPCRRVZAWVJL-UHFFFAOYSA-N 0.000 claims 1
- SYLKGSBVKMSQMT-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-([1,3]thiazolo[4,5-c]pyridin-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound N1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 SYLKGSBVKMSQMT-UHFFFAOYSA-N 0.000 claims 1
- BXSCGJPJCIGHLT-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-([1,3]thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CN=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 BXSCGJPJCIGHLT-UHFFFAOYSA-N 0.000 claims 1
- AGLXJYUZHSHVGW-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-([1,3]thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=NC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 AGLXJYUZHSHVGW-UHFFFAOYSA-N 0.000 claims 1
- IJARDSRRNICYGG-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-(imidazo[1,2-a]pyridin-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=CC2=NC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=CN21 IJARDSRRNICYGG-UHFFFAOYSA-N 0.000 claims 1
- HIDAZKFPIYYHBS-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-(imidazo[1,2-b]pyridazin-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound N1=CC=CC2=NC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5CC(CC(C5)C3)C4)C)=CN21 HIDAZKFPIYYHBS-UHFFFAOYSA-N 0.000 claims 1
- WQOZTYXEAIOXHM-UHFFFAOYSA-N 3-[1-(1-adamantylmethyl)-5-methyltriazol-4-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=N3)CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 WQOZTYXEAIOXHM-UHFFFAOYSA-N 0.000 claims 1
- LEDCZSOKLOQIDL-UHFFFAOYSA-N 3-[1-[2-(1-adamantyl)ethyl]-5-cyano-2-methylpyrrol-3-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(C(C#N)=C3)CCC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 LEDCZSOKLOQIDL-UHFFFAOYSA-N 0.000 claims 1
- IWMMMZGYHDPBMY-UHFFFAOYSA-N 3-[2-(1-adamantylamino)-3-methylpyridin-4-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=CC=NC(NC45CC6CC(CC(C6)C4)C5)=C3C)=NC2=C1 IWMMMZGYHDPBMY-UHFFFAOYSA-N 0.000 claims 1
- CSLZXOVQZOFAEC-UHFFFAOYSA-N 3-[3-(1-adamantylsulfonyl)-2-cyanophenyl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C=3N=C(C(=CC=3)C=3C(=C(C=CC=3)S(=O)(=O)C34CC5CC(CC(C5)C3)C4)C#N)C(=O)O)=NC2=C1 CSLZXOVQZOFAEC-UHFFFAOYSA-N 0.000 claims 1
- MMXDTUDYYBOMAB-UHFFFAOYSA-N 3-[3-[1-adamantylmethyl(methyl)amino]-2-methylphenyl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C=3C=CC=C(C=3C)N(CC34CC5CC(CC(C5)C3)C4)C)=NC2=C1 MMXDTUDYYBOMAB-UHFFFAOYSA-N 0.000 claims 1
- VDXYLGSKAFNVQM-UHFFFAOYSA-N 3-[3-[2-adamantyl(methyl)sulfamoyl]-2-methylphenyl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C=3C=CC=C(C=3C)S(=O)(=O)N(C3C4CC5CC(C4)CC3C5)C)=NC2=C1 VDXYLGSKAFNVQM-UHFFFAOYSA-N 0.000 claims 1
- HJYSWLUWOJOXJI-UHFFFAOYSA-N 3-[3-[adamantane-1-carbonyl(methyl)amino]-2-methylphenyl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C=3C=CC=C(C=3C)N(C(=O)C34CC5CC(CC(C5)C3)C4)C)=NC2=C1 HJYSWLUWOJOXJI-UHFFFAOYSA-N 0.000 claims 1
- CJJMAWPEZKYJAP-UHFFFAOYSA-N 3-hydroxyadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2(O)CC1(C(=O)O)C3 CJJMAWPEZKYJAP-UHFFFAOYSA-N 0.000 claims 1
- SIMWKAPKJBPDFW-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-3-[1-(2-oxatricyclo[3.3.1.13,7]decan-1-ylmethyl)pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C=3N=C(C(=CC=3)C3=CN(CC45OC6CC(CC(C6)C4)C5)N=C3)C(=O)O)=NC2=C1 SIMWKAPKJBPDFW-UHFFFAOYSA-N 0.000 claims 1
- RQLRRVMPMGMPFK-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-3-[5-cyano-2-methyl-1-[(3-methyl-2-oxatricyclo[3.3.1.13,7]decan-1-yl)methyl]pyrrol-3-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(C(C#N)=C3)CC34OC5(C)CC(CC(C5)C3)C4)C)=NC2=C1 RQLRRVMPMGMPFK-UHFFFAOYSA-N 0.000 claims 1
- XGVPFJVDQQIOQE-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-(spiro[3.5]nonan-7-ylmethyl)pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(N2CC3=C(C(=O)NC=4SC5=CC=CC=C5N=4)C=CC=C3CC2)=CC=C1C(=C1)C=NN1CC(CC1)CCC21CCC2 XGVPFJVDQQIOQE-UHFFFAOYSA-N 0.000 claims 1
- DIKNGMWFGWLQSZ-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(3,5,7-trimethyl-1-adamantyl)methyl]pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=CN(N=C3)CC34CC5(C)CC(C3)(C)CC(C5)(C4)C)=NC2=C1 DIKNGMWFGWLQSZ-UHFFFAOYSA-N 0.000 claims 1
- OADAEYHGDXGPOT-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(3,5-dimethyl-1-adamantyl)methyl]-5-methylpyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34CC5(C)CC(C)(CC(C5)C3)C4)C)=NC2=C1 OADAEYHGDXGPOT-UHFFFAOYSA-N 0.000 claims 1
- QPGIGJKUNAAHCG-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(3,5-dimethyl-1-adamantyl)methyl]pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=CN(N=C3)CC34CC5(C)CC(C4)CC(C5)(C3)C)=NC2=C1 QPGIGJKUNAAHCG-UHFFFAOYSA-N 0.000 claims 1
- TTYCXRNLXMYOFM-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(3-methoxy-5,7-dimethyl-1-adamantyl)methyl]-5-methylpyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C=3C=NN(C=3C)CC34CC5(CC(C4)(C)CC(C3)(C5)OC)C)=NC2=C1 TTYCXRNLXMYOFM-UHFFFAOYSA-N 0.000 claims 1
- YBQQRSGYPYSEJQ-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(3-morpholin-4-yl-1-adamantyl)methyl]pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(N2CC3=C(C(=O)NC=4SC5=CC=CC=C5N=4)C=CC=C3CC2)=CC=C1C(=C1)C=NN1CC(C1)(C2)CC(C3)CC1CC32N1CCOCC1 YBQQRSGYPYSEJQ-UHFFFAOYSA-N 0.000 claims 1
- IFRNQHMRUMRVLH-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(3-propan-2-yloxy-1-adamantyl)methyl]pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=CN(N=C3)CC34CC5CC(C4)CC(C3)(C5)OC(C)C)=NC2=C1 IFRNQHMRUMRVLH-UHFFFAOYSA-N 0.000 claims 1
- DYFNZDQOCYJSDS-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(7-methoxyspiro[2.5]octan-7-yl)methyl]-5-methylpyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1C(OC)(CN2C(=C(C=N2)C=2C(=NC(=CC=2)N2CC3=C(C(=O)NC=4SC5=CC=CC=C5N=4)C=CC=C3CC2)C(O)=O)C)CCCC21CC2 DYFNZDQOCYJSDS-UHFFFAOYSA-N 0.000 claims 1
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