JP2014530238A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- HPZBVFMZBPTMQN-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[(8-phenylmethoxycarbonyl-8-azabicyclo[3.2.1]octan-3-yl)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)CC2CCC1N2C(=O)OCC1=CC=CC=C1 HPZBVFMZBPTMQN-UHFFFAOYSA-N 0.000 claims 1
- SSPQPDVKWPJZTO-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[[1-(2-methoxyethyl)cyclooctyl]methyl]-5-methylpyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound N1=CC(C=2C(=NC(=CC=2)N2CC3=C(C(=O)NC=4SC5=CC=CC=C5N=4)C=CC=C3CC2)C(O)=O)=C(C)N1CC1(CCOC)CCCCCCC1 SSPQPDVKWPJZTO-UHFFFAOYSA-N 0.000 claims 1
- LZLAVIXOIZTYNG-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[[2-(2-methoxyethyl)-2-adamantyl]methyl]pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1C(C2)CC3CC1C(CCOC)(CN1N=CC(=C1)C=1C(=NC(=CC=1)N1CC4=C(C(=O)NC=5SC6=CC=CC=C6N=5)C=CC=C4CC1)C(O)=O)C2C3 LZLAVIXOIZTYNG-UHFFFAOYSA-N 0.000 claims 1
- JESAQMQUUABFQK-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[[3-(2-methoxyethoxy)-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)CC34CC5CC(C4)CC(C3)(C5)OCCOC)=NC2=C1 JESAQMQUUABFQK-UHFFFAOYSA-N 0.000 claims 1
- JTYNGEZHTZRUSQ-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[[3-(2-methoxyethoxy)-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)OCCOC)=NC2=C1 JTYNGEZHTZRUSQ-UHFFFAOYSA-N 0.000 claims 1
- ICFZNOOVSQQGNO-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[1-[[3-(2-morpholin-4-ylethoxy)-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)CC1CC32OCCN1CCOCC1 ICFZNOOVSQQGNO-UHFFFAOYSA-N 0.000 claims 1
- IYEQISMDGIDVTP-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[2-[cyclooctyl(methyl)amino]-3-methylpyridin-4-yl]pyridine-2-carboxylic acid Chemical compound N=1C=CC(C=2C(=NC(=CC=2)N2CC3=C(C(=O)NC=4SC5=CC=CC=C5N=4)C=CC=C3CC2)C(O)=O)=C(C)C=1N(C)C1CCCCCCC1 IYEQISMDGIDVTP-UHFFFAOYSA-N 0.000 claims 1
- YLNORSRIFUNEGX-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[5-cyano-1-[(3-methoxy-1-adamantyl)methyl]-2-methylpyrrol-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(C)N(C(=C3)C#N)CC34CC5CC(C4)CC(C3)(C5)OC)=NC2=C1 YLNORSRIFUNEGX-UHFFFAOYSA-N 0.000 claims 1
- DJTYNIOLTRGOJE-UHFFFAOYSA-N 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1h-isoquinolin-2-yl]-3-[5-methyl-1-[[1-(2-methylsulfonylethoxy)cyclooctyl]methyl]pyrazol-4-yl]pyridine-2-carboxylic acid Chemical compound CC1=C(C=2C(=NC(=CC=2)N2CC3=C(C(=O)NC=4SC5=CC=CC=C5N=4)C=CC=C3CC2)C(O)=O)C=NN1CC1(OCCS(C)(=O)=O)CCCCCCC1 DJTYNIOLTRGOJE-UHFFFAOYSA-N 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- XPCVRYRUUUMVTI-UHFFFAOYSA-N 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)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 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)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 XPCVRYRUUUMVTI-UHFFFAOYSA-N 0.000 claims 1
- JTDXSZVTTZNZLD-UHFFFAOYSA-N C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 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)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 JTDXSZVTTZNZLD-UHFFFAOYSA-N 0.000 claims 1
- ZERNGYVDRAHDDL-UHFFFAOYSA-N C1=CC=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=N3)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 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)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 ZERNGYVDRAHDDL-UHFFFAOYSA-N 0.000 claims 1
- HYAXKVJHFGIGOL-UHFFFAOYSA-N C1=CN=C2SC(NC(=O)C=3C=CC=C4CCN(CC4=3)C3=CC=C(C(=N3)C(O)=O)C3=C(N(N=C3)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 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)CC34OC5CC(CC(C5)C3)C4)C)=NC2=C1 HYAXKVJHFGIGOL-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 229910052805 deuterium Inorganic materials 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 230000036210 malignancy Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002912 morpholin-4-ylsulfonyl group Chemical group O1C([H])([H])C([H])([H])N(S(=O)(=O)[*])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 7
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161547162P | 2011-10-14 | 2011-10-14 | |
| US61/547,162 | 2011-10-14 | ||
| CN2012079012 | 2012-07-23 | ||
| CNPCT/CN2012/079012 | 2012-07-23 | ||
| PCT/US2012/059720 WO2013055897A1 (en) | 2011-10-14 | 2012-10-11 | 8 - carbamoyl - 2 - (2,3- di substituted pyrid - 6 - yl) -1,2,3,4 -tetrahydroisoquinoline derivatives as apoptosis - inducing agents for the treatment of cancer and immune and autoimmune diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017082912A Division JP6395893B2 (ja) | 2011-10-14 | 2017-04-19 | 癌ならびに免疫疾患および自己免疫疾患の治療のためのアポトーシス誘発剤としての８−カルバモイル−２−（２，３−ジ置換ピリド−６−イル）−１，２，３，４−テトラヒドロイソキノリン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014530238A JP2014530238A (ja) | 2014-11-17 |
| JP2014530238A5 true JP2014530238A5 (show.php) | 2015-12-03 |
| JP6155270B2 JP6155270B2 (ja) | 2017-06-28 |
Family
ID=47116421
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014535869A Active JP6155270B2 (ja) | 2011-10-14 | 2012-10-11 | 癌ならびに免疫疾患および自己免疫疾患の治療のためのアポトーシス誘発剤としての８−カルバモイル−２−（２，３−ジ置換ピリド−６−イル）−１，２，３，４−テトラヒドロイソキノリン誘導体 |
| JP2017082912A Active JP6395893B2 (ja) | 2011-10-14 | 2017-04-19 | 癌ならびに免疫疾患および自己免疫疾患の治療のためのアポトーシス誘発剤としての８−カルバモイル−２−（２，３−ジ置換ピリド−６−イル）−１，２，３，４−テトラヒドロイソキノリン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017082912A Active JP6395893B2 (ja) | 2011-10-14 | 2017-04-19 | 癌ならびに免疫疾患および自己免疫疾患の治療のためのアポトーシス誘発剤としての８−カルバモイル−２−（２，３−ジ置換ピリド−６−イル）−１，２，３，４−テトラヒドロイソキノリン誘導体 |
Country Status (36)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI561521B (en) | 2011-10-14 | 2016-12-11 | Abbvie Inc | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US8889675B2 (en) | 2011-10-14 | 2014-11-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| CA2970155A1 (en) * | 2014-12-09 | 2016-06-16 | Abbvie Inc. | Bcl-xl inhibitory compounds having low cell permeability and antibody drug conjugates including the same |
| CN111620862A (zh) * | 2014-12-09 | 2020-09-04 | 艾伯维公司 | Bcl-xl抑制性化合物和包括其的抗体药物缀合物 |
| WO2016094505A1 (en) * | 2014-12-09 | 2016-06-16 | Abbvie Inc. | Antibody drug conjugates with cell permeable bcl-xl inhibitors |
| CN104473923B (zh) * | 2014-12-29 | 2016-08-17 | 巩春智 | 一种防治慢性心力衰竭的药物组合物及其应用 |
| WO2016131100A1 (en) * | 2015-02-18 | 2016-08-25 | The Walter And Eliza Hall Institute Of Medical Research | Methods of treating infectious diseases |
| US10195213B2 (en) | 2015-03-13 | 2019-02-05 | Unity Biotechnology, Inc. | Chemical entities that kill senescent cells for use in treating age-related disease |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| CA3027181A1 (en) * | 2016-06-08 | 2017-12-14 | Abbvie Inc. | Anti-egfr antibody drug conjugates |
| EP3468596A2 (en) * | 2016-06-08 | 2019-04-17 | AbbVie Inc. | Anti-cd98 antibodies and antibody drug conjugates |
| JP2019521106A (ja) * | 2016-06-08 | 2019-07-25 | アッヴィ・インコーポレイテッド | 抗ｅｇｆｒ抗体薬物コンジュゲート |
| JP2019522643A (ja) * | 2016-06-08 | 2019-08-15 | アッヴィ・インコーポレイテッド | 抗ｃｄ９８抗体及び抗体薬物コンジュゲート |
| EP3888689A1 (en) * | 2016-06-08 | 2021-10-06 | AbbVie Inc. | Anti-egfr antibody drug conjugates |
| IL300274A (en) | 2016-06-08 | 2023-04-01 | Abbvie Inc | Antibodies against B7–H3 and conjugates of drug and antibody |
| CA3027033A1 (en) * | 2016-06-08 | 2017-12-14 | Abbvie Inc. | Anti-cd98 antibodies and antibody drug conjugates |
| WO2018092064A1 (en) * | 2016-11-18 | 2018-05-24 | Novartis Ag | Combinations of mdm2 inhibitors and bcl-xl inhibitors |
| WO2019000236A1 (en) * | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| TW202002952A (zh) | 2018-03-15 | 2020-01-16 | 美商艾伯維有限公司 | 用於治療胰臟癌之abbv-621與抗癌劑之組合 |
| AR119494A1 (es) * | 2019-07-29 | 2021-12-22 | Servier Lab | DERIVADOS DE 6,7-DIHIDRO-5H-PIRIDO[2,3-c]PIRIDAZIN-8-ILO, COMPOSICIONES FARMACÉUTICAS QUE LOS CONTIENEN Y SUS USOS COMO AGENTES PROAPOPTÓTICOS |
| WO2022115477A1 (en) | 2020-11-24 | 2022-06-02 | Novartis Ag | Bcl-xl inhibitor antibody-drug conjugates and methods of use thereof |
| AR124681A1 (es) | 2021-01-20 | 2023-04-26 | Abbvie Inc | Conjugados anticuerpo-fármaco anti-egfr |
| IL304891A (en) | 2021-02-02 | 2023-10-01 | Servier Lab | Selective Protech BCL-XL compounds and methods of use |
| EP4519272A1 (en) * | 2022-05-06 | 2025-03-12 | Treeline Biosciences, Inc. | Tetrahydroisoquinoline heterobifunctional bcl-xl degraders |
| JP2025517642A (ja) * | 2022-05-06 | 2025-06-10 | ツリーライン バイオサイエンシズ インコーポレイテッド | テトラヒドロイソキノリンヘテロ二官能性ｂｃｌ－ｘｌ分解剤 |
| CA3256012A1 (en) | 2022-05-20 | 2023-11-23 | Les Laboratoires Servier | ANTIBODY-DRUG CONJUGATES, MET INHIBITORS BCL-XL, AND THEIR METHODS OF USE |
| WO2023225320A1 (en) | 2022-05-20 | 2023-11-23 | Novartis Ag | Epha2 bcl-xl inhibitor antibody-drug conjugates and methods of use thereof |
| TW202408588A (zh) | 2022-05-20 | 2024-03-01 | 瑞士商諾華公司 | 抗體-藥物結合物抗腫瘤化合物及其使用方法 |
| EP4538273A1 (en) * | 2022-06-10 | 2025-04-16 | Hitgen Inc. | Compound and use thereof in preparation of bcl-xl inhibitor |
| TW202540185A (zh) | 2023-11-22 | 2025-10-16 | 法商施維雅藥廠 | 抗cd74抗體藥物結合物及其使用方法 |
| WO2025111431A1 (en) | 2023-11-22 | 2025-05-30 | Les Laboratoires Servier | Anti-cd7 antibody-drug conjugates and methods of use thereof |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| AU6964096A (en) | 1995-09-15 | 1997-04-01 | Pharmacia & Upjohn Company | Aminoaryl oxazolidinone n-oxides |
| US20030220234A1 (en) | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| GB9918037D0 (en) | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| YU96502A (sh) * | 2000-06-21 | 2006-01-16 | F. Hoffmann-La Roche Ag. | Derivati benzotiazola |
| AU2003297219A1 (en) | 2002-12-20 | 2004-07-22 | Merck & Co., Inc. | 3-amino-4-phenylbutanoic acid derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes |
| PL1737850T3 (pl) | 2004-04-19 | 2008-02-29 | Symed Labs Ltd | Nowy sposób wytwarzania linezolidu i związków pokrewnych |
| PL1768967T3 (pl) | 2004-07-20 | 2009-09-30 | Symed Labs Ltd | Nowe związki pośrednie do wytwarzania linezolidu oraz związki pokrewne |
| EP1804823A4 (en) | 2004-09-29 | 2010-06-09 | Amr Technology Inc | NEW CYCLOSPORIN ANALOGUE AND ITS PHARMACEUTICAL APPLICATIONS |
| TW200716636A (en) | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| US7514068B2 (en) | 2005-09-14 | 2009-04-07 | Concert Pharmaceuticals Inc. | Biphenyl-pyrazolecarboxamide compounds |
| US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
| AU2008214774A1 (en) | 2007-02-15 | 2008-08-21 | F. Hoffmann-La Roche Ag | 2-aminooxazolines as TAAR1 ligands |
| AU2008242703B2 (en) | 2007-04-19 | 2011-08-18 | Concert Pharmaceuticals Inc. | Deuterated morpholinyl compounds |
| US7531685B2 (en) | 2007-06-01 | 2009-05-12 | Protia, Llc | Deuterium-enriched oxybutynin |
| WO2009035598A1 (en) | 2007-09-10 | 2009-03-19 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
| US20090118238A1 (en) | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
| US20090082471A1 (en) | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched fingolimod |
| US20090088416A1 (en) | 2007-09-26 | 2009-04-02 | Protia, Llc | Deuterium-enriched lapaquistat |
| US20090137457A1 (en) | 2007-10-02 | 2009-05-28 | Concert Pharmaceuticals, Inc. | Pyrimidinedione derivatives |
| US20090105338A1 (en) | 2007-10-18 | 2009-04-23 | Protia, Llc | Deuterium-enriched gabexate mesylate |
| EP2212298B1 (en) | 2007-10-18 | 2013-03-27 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
| CA2703591C (en) | 2007-10-26 | 2013-05-07 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| CA2747170C (en) * | 2008-12-19 | 2017-07-18 | Abbott Laboratories | Tetrahydroisoquinoline derivatives and their uses to treat cancers and autoimmune disorders |
| CN102325531B (zh) * | 2008-12-19 | 2014-04-02 | 健泰科生物技术公司 | 化合物和使用方法 |
| KR20110123657A (ko) * | 2010-05-07 | 2011-11-15 | 에스케이케미칼주식회사 | 피콜린아마이드 및 피리미딘-4-카복사미드 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
| TWI561521B (en) * | 2011-10-14 | 2016-12-11 | Abbvie Inc | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
-
2012
- 2012-10-08 TW TW101137131A patent/TWI571466B/zh not_active IP Right Cessation
- 2012-10-10 UY UY0001034382A patent/UY34382A/es unknown
- 2012-10-11 UA UAA201405089A patent/UA115042C2/uk unknown
- 2012-10-11 SI SI201230730A patent/SI2766361T1/sl unknown
- 2012-10-11 ES ES12780605.7T patent/ES2598877T3/es active Active
- 2012-10-11 SG SG11201401279XA patent/SG11201401279XA/en unknown
- 2012-10-11 MY MYPI2014700867A patent/MY172723A/en unknown
- 2012-10-11 HU HUE12780605A patent/HUE030589T2/en unknown
- 2012-10-11 LT LTEP12780605.7T patent/LT2766361T/lt unknown
- 2012-10-11 CA CA2851364A patent/CA2851364C/en active Active
- 2012-10-11 KR KR1020147012846A patent/KR102019643B1/ko not_active Expired - Fee Related
- 2012-10-11 PE PE2014000506A patent/PE20141282A1/es active IP Right Grant
- 2012-10-11 HR HRP20161319TT patent/HRP20161319T1/hr unknown
- 2012-10-11 JP JP2014535869A patent/JP6155270B2/ja active Active
- 2012-10-11 PT PT127806057T patent/PT2766361T/pt unknown
- 2012-10-11 PH PH1/2014/500729A patent/PH12014500729A1/en unknown
- 2012-10-11 PL PL12780605T patent/PL2766361T3/pl unknown
- 2012-10-11 AU AU2012322698A patent/AU2012322698A1/en not_active Abandoned
- 2012-10-11 DK DK12780605.7T patent/DK2766361T3/en active
- 2012-10-11 ME MEP-2016-227A patent/ME02514B/me unknown
- 2012-10-11 MX MX2014004556A patent/MX356031B/es active IP Right Grant
- 2012-10-11 BR BR112014009053-0A patent/BR112014009053B1/pt not_active IP Right Cessation
- 2012-10-11 RS RS20160954A patent/RS55342B1/sr unknown
- 2012-10-11 WO PCT/US2012/059720 patent/WO2013055897A1/en not_active Ceased
- 2012-10-11 EP EP12780605.7A patent/EP2766361B1/en active Active
- 2012-10-11 RU RU2014119250A patent/RU2625315C2/ru active
- 2012-10-11 CR CR20200097A patent/CR20200097A/es unknown
- 2012-10-12 AR ARP120103811A patent/AR088327A1/es active IP Right Grant
-
2014
- 2014-04-01 IL IL231856A patent/IL231856A/en active IP Right Grant
- 2014-04-08 ZA ZA2014/02556A patent/ZA201402556B/en unknown
- 2014-04-09 DO DO2014000070A patent/DOP2014000070A/es unknown
- 2014-04-10 CL CL2014000905A patent/CL2014000905A1/es unknown
- 2014-04-10 GT GT201400064A patent/GT201400064A/es unknown
- 2014-05-06 CR CR20140205A patent/CR20140205A/es unknown
- 2014-05-07 CO CO14097093A patent/CO6950476A2/es unknown
- 2014-05-08 EC ECIEPI2014357A patent/ECSP14000357A/es unknown
-
2015
- 2015-06-30 PH PH12015501498A patent/PH12015501498B1/en unknown
-
2016
- 2016-10-27 CY CY20161101096T patent/CY1118224T1/el unknown
-
2017
- 2017-04-19 JP JP2017082912A patent/JP6395893B2/ja active Active
- 2017-07-20 AU AU2017206246A patent/AU2017206246B2/en not_active Ceased
-
2019
- 2019-02-01 DO DO2019000022A patent/DOP2019000022A/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014530238A5 (show.php) | ||
| RU2014119250A (ru) | Производные 8-карбамоил-2-(2,3-дизамещенного пирид-6-ил)-1,2,3,4-тетрагидроизохинолина в качестве индуцирующих апоптоз средств для лечения рака и иммунных и аутоиммунных заболеваний | |
| ES2398843T3 (es) | Imidazotriazinas e imidazopirimidinas como inhibidores de la quinasa | |
| CN111386118B (zh) | 作为rsv抑制剂的组合药物剂 | |
| RU2017138100A (ru) | Имидазолонилхинолины и их применение в качестве ингибиторов киназы атм | |
| JP2014530237A5 (show.php) | ||
| RU2017105296A (ru) | Новые соединения | |
| CN112204027A (zh) | Erk 抑制剂及其应用 | |
| RU2012152548A (ru) | Пиридоновые и азапиридоновые соединения и способы применения | |
| BR112020008839A2 (pt) | moduladores da via de estresse integrada | |
| JP2017530960A5 (show.php) | ||
| JP2021502356A5 (show.php) | ||
| HRP20201469T1 (hr) | Derivati tetrahidroizokinolina | |
| US20190241533A1 (en) | Novel compounds and compositions for inhibition of fasn | |
| JP2013523884A5 (show.php) | ||
| RU2013143747A (ru) | Соединения бензоксазепина, селективные в отношении pi3k p110 дельта и способы их применения | |
| JP2010510319A5 (show.php) | ||
| JP2018510857A5 (show.php) | ||
| RU2016124178A (ru) | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет | |
| JP2011509307A5 (show.php) | ||
| JP2013534902A5 (show.php) | ||
| HRP20160539T1 (hr) | Antagonisti trpv4 | |
| JP2019508384A (ja) | ５−置換２−（モルホリン−４−イル）−１，７−ナフチリジン | |
| JP2016507551A5 (show.php) | ||
| PT1966202E (pt) | Pirrolo[2,3-b] pirimidinas e pirrolo[2,3-b]piridinas substituídas com heteroarilo como inibidores de janus quinase |