JP2017501983A5 - - Google Patents
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- Publication number
- JP2017501983A5 JP2017501983A5 JP2016535650A JP2016535650A JP2017501983A5 JP 2017501983 A5 JP2017501983 A5 JP 2017501983A5 JP 2016535650 A JP2016535650 A JP 2016535650A JP 2016535650 A JP2016535650 A JP 2016535650A JP 2017501983 A5 JP2017501983 A5 JP 2017501983A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- dihydroimidazo
- quinazolin
- morpholin
- ylpropoxy
- 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 nitro, hydroxy Chemical group 0.000 claims 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 206010060862 Prostate cancer Diseases 0.000 claims 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 229960003966 nicotinamide Drugs 0.000 claims 5
- 235000005152 nicotinamide Nutrition 0.000 claims 5
- 239000011570 nicotinamide Substances 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 4
- 206010027476 Metastases Diseases 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 150000003857 carboxamides Chemical class 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 201000005202 lung cancer Diseases 0.000 claims 4
- 208000020816 lung neoplasm Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 3
- MWYDSXOGIBMAET-UHFFFAOYSA-N 2-amino-N-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydro-1H-imidazo[1,2-c]quinazolin-5-ylidene]pyrimidine-5-carboxamide Chemical compound NC1=NC=C(C=N1)C(=O)N=C1N=C2C(=C(C=CC2=C2N1CCN2)OCCCN1CCOCC1)OC MWYDSXOGIBMAET-UHFFFAOYSA-N 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- NIQHXSFKSLJILV-UHFFFAOYSA-N NC1N(C=CC=N1)C1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCN2CCOCC2)OC Chemical compound NC1N(C=CC=N1)C1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCN2CCOCC2)OC NIQHXSFKSLJILV-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- PFAXMTRQGWBENF-UHFFFAOYSA-N n-[8-[3-[2-(hydroxymethyl)morpholin-4-yl]propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1CCOC(CO)C1 PFAXMTRQGWBENF-UHFFFAOYSA-N 0.000 claims 3
- 229910052705 radium Inorganic materials 0.000 claims 3
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 230000009401 metastasis Effects 0.000 claims 2
- VOJJBKFDVYAHHS-UHFFFAOYSA-N n-[7-methoxy-8-(2-morpholin-4-ylethoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCN1CCOCC1 VOJJBKFDVYAHHS-UHFFFAOYSA-N 0.000 claims 2
- VLPUKEZMPQNOHW-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C3=C(N=C(C)S3)C)=NC=2C(OC)=C1OCCCN1CCOCC1 VLPUKEZMPQNOHW-UHFFFAOYSA-N 0.000 claims 2
- WCRDAUWROGEPIU-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-6-methylpyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(C)=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 WCRDAUWROGEPIU-UHFFFAOYSA-N 0.000 claims 2
- PTBHOHFIBIMRLB-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 PTBHOHFIBIMRLB-UHFFFAOYSA-N 0.000 claims 2
- MYZQRTALORWOFJ-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 MYZQRTALORWOFJ-UHFFFAOYSA-N 0.000 claims 2
- IGDWQPUGKSBEED-UHFFFAOYSA-N n-[8-[2-(dimethylamino)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound N=1C=2C(OC)=C(OCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C=1SC(C)=NC=1C IGDWQPUGKSBEED-UHFFFAOYSA-N 0.000 claims 2
- WNUPSDDMPRHUPR-UHFFFAOYSA-N n-[8-[2-(dimethylamino)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound N=1C=2C(OC)=C(OCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 WNUPSDDMPRHUPR-UHFFFAOYSA-N 0.000 claims 2
- XYVNDTVSILQGKM-UHFFFAOYSA-N n-[8-[2-(dimethylamino)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamide Chemical compound N=1C=2C(OC)=C(OCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CN=CN=C1 XYVNDTVSILQGKM-UHFFFAOYSA-N 0.000 claims 2
- SBJDLHJPWPQZLP-UHFFFAOYSA-N n-[8-[3-(dimethylamino)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound N=1C=2C(OC)=C(OCCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 SBJDLHJPWPQZLP-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- HCWPIIXVSYCSAN-OIOBTWANSA-N radium-223 Chemical compound [223Ra] HCWPIIXVSYCSAN-OIOBTWANSA-N 0.000 claims 2
- 229960005562 radium-223 Drugs 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 1
- LNMCRSJMLGCLCZ-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3N=C(N)OC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 LNMCRSJMLGCLCZ-UHFFFAOYSA-N 0.000 claims 1
- AQMSKYKATADCTL-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-1,3-oxazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3OC(N)=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 AQMSKYKATADCTL-UHFFFAOYSA-N 0.000 claims 1
- RWCMUSCEPMWINC-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3SC(N)=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 RWCMUSCEPMWINC-UHFFFAOYSA-N 0.000 claims 1
- NFNLEBOQOSHXAE-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C3=C(N=C(N)S3)C)=NC=2C(OC)=C1OCCCN1CCOCC1 NFNLEBOQOSHXAE-UHFFFAOYSA-N 0.000 claims 1
- JVNVQISIPQMGQT-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-4-methylpyrimidine-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C(=NC(N)=NC=3)C)=NC=2C(OC)=C1OCCCN1CCOCC1 JVNVQISIPQMGQT-UHFFFAOYSA-N 0.000 claims 1
- BEMUPKPURPXIOV-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-4-propylpyrimidine-5-carboxamide Chemical compound CCCC1=NC(N)=NC=C1C(=O)NC1=NC2=C(OC)C(OCCCN3CCOCC3)=CC=C2C2=NCCN12 BEMUPKPURPXIOV-UHFFFAOYSA-N 0.000 claims 1
- HTXHYBJJPFAYJF-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-4-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3N=C(N)N=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 HTXHYBJJPFAYJF-UHFFFAOYSA-N 0.000 claims 1
- LTMJJJRJLOZDKC-UHFFFAOYSA-N 2-amino-n-[8-[3-(dimethylamino)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamide Chemical compound N=1C=2C(OC)=C(OCCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CN=C(N)N=C1 LTMJJJRJLOZDKC-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- BMALKTLCGJCSFT-UHFFFAOYSA-N 2-methoxy-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)NC1=NC2=C(OC)C(OCCCN3CCOCC3)=CC=C2C2=NCCN12 BMALKTLCGJCSFT-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- PRGHVANXJBUMMP-UHFFFAOYSA-N 6-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2-methylpyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C(=NC(N)=CC=3)C)=NC=2C(OC)=C1OCCCN1CCOCC1 PRGHVANXJBUMMP-UHFFFAOYSA-N 0.000 claims 1
- YREMFJUNYZTERX-UHFFFAOYSA-N C(C(C)C)(=O)NN1C(N2C(C=3C=CC(=C(C13)OC)OCCCN1CCOCC1)=NCC2)N2CC=CC(=C2)C2N(C)CCC2 Chemical compound C(C(C)C)(=O)NN1C(N2C(C=3C=CC(=C(C13)OC)OCCCN1CCOCC1)=NCC2)N2CC=CC(=C2)C2N(C)CCC2 YREMFJUNYZTERX-UHFFFAOYSA-N 0.000 claims 1
- UTSTWSBQVYVZAL-UHFFFAOYSA-N C1(CCC1)CN1CC(OCC1)CCOC=1C=CC=2C=3N(C(=NC2C1OC)N1CC=CC(=C1)C1N(C)CCC1)CCN3 Chemical compound C1(CCC1)CN1CC(OCC1)CCOC=1C=CC=2C=3N(C(=NC2C1OC)N1CC=CC(=C1)C1N(C)CCC1)CCN3 UTSTWSBQVYVZAL-UHFFFAOYSA-N 0.000 claims 1
- KQVLFZDOTHDTAM-HDICACEKSA-N C[C@@H]1CN(C[C@@H](O1)C)CCCOC=1C=CC=2C=3N(C(=NC=2C=1OC)C1=C(C(=O)N)C=CC(=N1)C)CCN=3 Chemical compound C[C@@H]1CN(C[C@@H](O1)C)CCCOC=1C=CC=2C=3N(C(=NC=2C=1OC)C1=C(C(=O)N)C=CC(=N1)C)CCN=3 KQVLFZDOTHDTAM-HDICACEKSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010027454 Metastases to breast Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 108091007960 PI3Ks Proteins 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 1
- FTPSRPZIUIMGJG-UHFFFAOYSA-N n-[7-methoxy-8-(2-piperidin-1-ylethoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCN1CCCCC1 FTPSRPZIUIMGJG-UHFFFAOYSA-N 0.000 claims 1
- HTWHGWBGGRQZIH-UHFFFAOYSA-N n-[7-methoxy-8-(2-pyrrolidin-1-ylethoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCN1CCCC1 HTWHGWBGGRQZIH-UHFFFAOYSA-N 0.000 claims 1
- KWJLJTBSGLETMV-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2-(methylamino)-1,3-thiazole-4-carboxamide Chemical compound S1C(NC)=NC(C(=O)NC=2N3CCN=C3C3=CC=C(OCCCN4CCOCC4)C(OC)=C3N=2)=C1 KWJLJTBSGLETMV-UHFFFAOYSA-N 0.000 claims 1
- SGKLUDAKPNLYEE-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3N=C(C)SC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 SGKLUDAKPNLYEE-UHFFFAOYSA-N 0.000 claims 1
- ZIDFUBHWWUXLRT-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2-morpholin-4-ylpyrimidine-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(=NC=3)N3CCOCC3)=NC=2C(OC)=C1OCCCN1CCOCC1 ZIDFUBHWWUXLRT-UHFFFAOYSA-N 0.000 claims 1
- JLKWVDHZVRQTKD-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2-pyrrolidin-1-ylpyrimidine-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(=NC=3)N3CCCC3)=NC=2C(OC)=C1OCCCN1CCOCC1 JLKWVDHZVRQTKD-UHFFFAOYSA-N 0.000 claims 1
- WKMOTJBONANCJS-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-6-piperazin-1-ylpyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(=CC=3)N3CCNCC3)=NC=2C(OC)=C1OCCCN1CCOCC1 WKMOTJBONANCJS-UHFFFAOYSA-N 0.000 claims 1
- ZWIHOWYOWLAPOW-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-6-pyrrolidin-1-ylpyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(=CC=3)N3CCCC3)=NC=2C(OC)=C1OCCCN1CCOCC1 ZWIHOWYOWLAPOW-UHFFFAOYSA-N 0.000 claims 1
- HERHMVXJRQROEC-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]furan-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C3=COC=C3)=NC=2C(OC)=C1OCCCN1CCOCC1 HERHMVXJRQROEC-UHFFFAOYSA-N 0.000 claims 1
- VSBKXPZKOULKMN-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrazine-2-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3N=CC=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 VSBKXPZKOULKMN-UHFFFAOYSA-N 0.000 claims 1
- CUZHQMVTVIFZLN-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-4-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=CN=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 CUZHQMVTVIFZLN-UHFFFAOYSA-N 0.000 claims 1
- CCLXFYQHHORRCJ-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-4-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3N=CN=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 CCLXFYQHHORRCJ-UHFFFAOYSA-N 0.000 claims 1
- LCPXEFLYSZVIKX-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]thiophene-2-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3SC=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 LCPXEFLYSZVIKX-UHFFFAOYSA-N 0.000 claims 1
- HAMKTMLNCPASGR-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]thiophene-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C3=CSC=C3)=NC=2C(OC)=C1OCCCN1CCOCC1 HAMKTMLNCPASGR-UHFFFAOYSA-N 0.000 claims 1
- ZHUXRHRQKUDHHC-UHFFFAOYSA-N n-[7-methoxy-8-(3-piperidin-1-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1CCCCC1 ZHUXRHRQKUDHHC-UHFFFAOYSA-N 0.000 claims 1
- IWNNQCNMNDPRNM-UHFFFAOYSA-N n-[7-methoxy-8-(morpholin-2-ylmethoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCC1CNCCO1 IWNNQCNMNDPRNM-UHFFFAOYSA-N 0.000 claims 1
- CLTOGHIOSYMIGR-UHFFFAOYSA-N n-[7-methoxy-8-[(4-methylmorpholin-2-yl)methoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCC1CN(C)CCO1 CLTOGHIOSYMIGR-UHFFFAOYSA-N 0.000 claims 1
- HGFPIMYEUVQSNS-UHFFFAOYSA-N n-[7-methoxy-8-[2-[4-(2-methoxyethyl)morpholin-2-yl]ethoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1N(CCOC)CCOC1CCOC1=CC=C(C=2N(CCN=2)C(NC(=O)C=2C=NC=CC=2)=N2)C2=C1OC HGFPIMYEUVQSNS-UHFFFAOYSA-N 0.000 claims 1
- MBTCIYIPCNTFMO-UHFFFAOYSA-N n-[7-methoxy-8-[3-(3-methylmorpholin-4-yl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1C MBTCIYIPCNTFMO-UHFFFAOYSA-N 0.000 claims 1
- FJLAKZHXRUSKFW-UHFFFAOYSA-N n-[7-methoxy-8-[3-(4-methylpiperazin-1-yl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1CCN(C)CC1 FJLAKZHXRUSKFW-UHFFFAOYSA-N 0.000 claims 1
- PUKCESPXCWGTSN-UHFFFAOYSA-N n-[7-methoxy-8-[3-(methylamino)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound N=1C2=C(OC)C(OCCCNC)=CC=C2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 PUKCESPXCWGTSN-UHFFFAOYSA-N 0.000 claims 1
- GZVXBDSYVFNCFF-UHFFFAOYSA-N n-[7-methoxy-8-[[4-(2-methoxyethyl)morpholin-2-yl]methoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1N(CCOC)CCOC1COC1=CC=C(C=2N(CCN=2)C(NC(=O)C=2C=NC=CC=2)=N2)C2=C1OC GZVXBDSYVFNCFF-UHFFFAOYSA-N 0.000 claims 1
- KUJFQKOTPRLKLL-UHFFFAOYSA-N n-[8-(2-aminoethoxy)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound N=1C=2C(OC)=C(OCCN)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 KUJFQKOTPRLKLL-UHFFFAOYSA-N 0.000 claims 1
- YTWYXKYMMKOBOM-UHFFFAOYSA-N n-[8-(2-hydroxy-3-morpholin-4-ylpropoxy)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCC(O)CN1CCOCC1 YTWYXKYMMKOBOM-UHFFFAOYSA-N 0.000 claims 1
- YYVUROKADZATNZ-UHFFFAOYSA-N n-[8-(3-aminopropoxy)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C=2C(OC)=C(OCCCN)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 YYVUROKADZATNZ-UHFFFAOYSA-N 0.000 claims 1
- XKVDGFQUQVVMRN-UHFFFAOYSA-N n-[8-[(4-ethylmorpholin-2-yl)methoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1N(CC)CCOC1COC1=CC=C(C=2N(CCN=2)C(NC(=O)C=2C=NC=CC=2)=N2)C2=C1OC XKVDGFQUQVVMRN-UHFFFAOYSA-N 0.000 claims 1
- WJTQKNQTKYYWRW-UHFFFAOYSA-N n-[8-[2-(4-ethylmorpholin-2-yl)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1N(CC)CCOC1CCOC1=CC=C(C=2N(CCN=2)C(NC(=O)C=2C=NC=CC=2)=N2)C2=C1OC WJTQKNQTKYYWRW-UHFFFAOYSA-N 0.000 claims 1
- UUMDZEMRXJMVLW-UHFFFAOYSA-N n-[8-[2-(diethylamino)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound N=1C2=C(OC)C(OCCN(CC)CC)=CC=C2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 UUMDZEMRXJMVLW-UHFFFAOYSA-N 0.000 claims 1
- ABYVJGMYXVHJSH-UHFFFAOYSA-N n-[8-[2-(dimethylamino)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-6-methylpyridine-3-carboxamide Chemical compound N=1C=2C(OC)=C(OCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=C(C)N=C1 ABYVJGMYXVHJSH-UHFFFAOYSA-N 0.000 claims 1
- AXWMUMUBHLBJJW-UHFFFAOYSA-N n-[8-[2-[di(propan-2-yl)amino]ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound N=1C=2C(OC)=C(OCCN(C(C)C)C(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 AXWMUMUBHLBJJW-UHFFFAOYSA-N 0.000 claims 1
- AITFHDROVDHPHJ-UHFFFAOYSA-N n-[8-[3-(diethylamino)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound N=1C2=C(OC)C(OCCCN(CC)CC)=CC=C2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 AITFHDROVDHPHJ-UHFFFAOYSA-N 0.000 claims 1
- FYGKNFXODIEWJB-UHFFFAOYSA-N n-[8-[3-(dimethylamino)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound N=1C=2C(OC)=C(OCCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=C[N+]([O-])=C1 FYGKNFXODIEWJB-UHFFFAOYSA-N 0.000 claims 1
- BQDLTRWPXDTWFK-HDICACEKSA-N n-[8-[3-[(2r,6s)-2,6-dimethylmorpholin-4-yl]propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1C[C@H](C)O[C@H](C)C1 BQDLTRWPXDTWFK-HDICACEKSA-N 0.000 claims 1
- LTQFHGCERMMMMZ-IYBDPMFKSA-N n-[8-[3-[(2s,6r)-2,6-dimethylmorpholin-4-yl]propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C3=C(N=C(C)S3)C)=NC=2C(OC)=C1OCCCN1C[C@H](C)O[C@H](C)C1 LTQFHGCERMMMMZ-IYBDPMFKSA-N 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- OBLVPWTUALCMGD-UHFFFAOYSA-N pyridin-1-ium-3-carboxamide;chloride Chemical compound Cl.NC(=O)C1=CC=CN=C1 OBLVPWTUALCMGD-UHFFFAOYSA-N 0.000 claims 1
- WLCIHZQHQBOALC-UHFFFAOYSA-N pyridine-3-carboxamide hydrate hydrochloride Chemical compound O.Cl.C(C1=CN=CC=C1)(=O)N WLCIHZQHQBOALC-UHFFFAOYSA-N 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 0 *C(NC(N1C(c2ccc3OI)=NCC1)=Nc2c3O*)=O Chemical compound *C(NC(N1C(c2ccc3OI)=NCC1)=Nc2c3O*)=O 0.000 description 1
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| EP13195485 | 2013-12-03 | ||
| PCT/EP2014/075886 WO2015082322A1 (en) | 2013-12-03 | 2014-11-28 | COMBINATION of PI3K-INHIBITORS |
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| JP2017501983A JP2017501983A (ja) | 2017-01-19 |
| JP2017501983A5 true JP2017501983A5 (https=) | 2017-12-28 |
| JP6499657B2 JP6499657B2 (ja) | 2019-04-10 |
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| EP (1) | EP3077002B1 (https=) |
| JP (1) | JP6499657B2 (https=) |
| CN (1) | CN105934256B (https=) |
| CA (1) | CA2932221C (https=) |
| WO (1) | WO2015082322A1 (https=) |
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| EP2168583A1 (en) | 2008-09-24 | 2010-03-31 | Bayer Schering Pharma Aktiengesellschaft | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma |
| EP2508525A1 (en) | 2011-04-05 | 2012-10-10 | Bayer Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts |
| MX2015014171A (es) | 2013-04-08 | 2015-12-16 | Bayer Pharma AG | Uso de 2,3-dihidroimidazo[1,2-c]quinazolinas sustituidas. |
| EP3077003A1 (en) | 2013-12-03 | 2016-10-12 | Bayer Pharma Aktiengesellschaft | Combination of pi3k-inhibitors |
| EP3018127A1 (en) | 2014-11-07 | 2016-05-11 | Bayer Pharma Aktiengesellschaft | Synthesis of copanlisib and its dihydrochloride salt |
| JP6867295B2 (ja) | 2015-03-09 | 2021-04-28 | バイエル ファーマ アクチエンゲゼルシャフト | 置換２，３−ジヒドロイミダゾ［１，２−ｃ］キナゾリンを含んでいる組合せ |
| CA3016584A1 (en) | 2016-03-08 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | 2-amino-n-[7-methoxy-2,3-dihydroimidazo-[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamides |
| CN109729716B (zh) * | 2016-09-23 | 2022-03-15 | 拜耳制药股份公司 | Pi3k-抑制剂的组合产品 |
| WO2018129399A1 (en) | 2017-01-05 | 2018-07-12 | Mbc Pharma, Inc. | Drug combination treatments using bone-targeting therapeutics for bone and bone-related disease |
| EP3645005A1 (en) | 2017-06-28 | 2020-05-06 | Bayer Consumer Care AG | Combination of a pi3k-inhibitor with an androgen receptor antagonist |
| JP2024515104A (ja) | 2021-04-20 | 2024-04-04 | テラパワー， エルエルシー | Ａｃ－２２５生成のためのチタニアに基づくジェネレータ |
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| NO310544B1 (no) | 1999-01-04 | 2001-07-23 | Algeta As | Opparbeidelse og anvendelse av radium-223 til fremstilling av preparat samt kit til behandling av kalsifisert vev for palliasjon, benkreft-terapi og/eller overflatebehandling av ben |
| EP1735013B1 (en) | 2004-02-20 | 2012-02-08 | Algeta ASA | Alpha- and beta-emitting hydroxyapatite particles |
| US20070141066A1 (en) * | 2005-12-16 | 2007-06-21 | Genentech, Inc. | Method for Diagnosing, Prognosing and Treating Glioma |
| AR064106A1 (es) * | 2006-12-05 | 2009-03-11 | Bayer Schering Pharma Ag | Derivados de 2,3-dihidroimidazo [1,2-c] quinazolina sustituida utiles para el tratamiento de enfermedades y trastornos hiper-proliferativos asociados con la angiogenesis |
| GB201007354D0 (en) | 2010-04-30 | 2010-06-16 | Algeta Asa | Method |
| GB201007353D0 (en) | 2010-04-30 | 2010-06-16 | Algeta Asa | Method |
| EP2638043B1 (en) | 2010-11-11 | 2017-06-07 | Bayer Intellectual Property GmbH | Arylaminoalcohol-substituted 2,3-dihydroimidazo[1,2-c]quinolines |
| UA113280C2 (xx) | 2010-11-11 | 2017-01-10 | АМІНОСПИРТЗАМІЩЕНІ ПОХІДНІ 2,3-ДИГІДРОІМІДАЗО$1,2-c]ХІНАЗОЛІНУ, ПРИДАТНІ ДЛЯ ЛІКУВАННЯ ГІПЕРПРОЛІФЕРАТИВНИХ ПОРУШЕНЬ І ЗАХВОРЮВАНЬ, ПОВ'ЯЗАНИХ З АНГІОГЕНЕЗОМ | |
| JP6165058B2 (ja) | 2010-11-11 | 2017-07-19 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | アルコキシ−置換２，３−ジヒドロイミダゾ［１，２−ｃ］キナゾリン |
| DE102011079031A1 (de) | 2011-07-12 | 2013-01-17 | Algeta Asa | Flüssigkeitsbehälter |
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2014
- 2014-11-28 WO PCT/EP2014/075886 patent/WO2015082322A1/en not_active Ceased
- 2014-11-28 EP EP14805266.5A patent/EP3077002B1/en active Active
- 2014-11-28 JP JP2016535650A patent/JP6499657B2/ja not_active Expired - Fee Related
- 2014-11-28 CN CN201480074721.5A patent/CN105934256B/zh not_active Expired - Fee Related
- 2014-11-28 US US15/101,638 patent/US10117874B2/en active Active
- 2014-11-28 CA CA2932221A patent/CA2932221C/en active Active
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