JP2009509961A5 - - Google Patents
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- Publication number
- JP2009509961A5 JP2009509961A5 JP2008532430A JP2008532430A JP2009509961A5 JP 2009509961 A5 JP2009509961 A5 JP 2009509961A5 JP 2008532430 A JP2008532430 A JP 2008532430A JP 2008532430 A JP2008532430 A JP 2008532430A JP 2009509961 A5 JP2009509961 A5 JP 2009509961A5
- Authority
- JP
- Japan
- Prior art keywords
- aminocyclohexyl
- trans
- imidazo
- pyridazine
- diamine
- 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
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 66
- 125000001072 heteroaryl group Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims 29
- 229910052757 nitrogen Inorganic materials 0.000 claims 24
- 125000003342 alkenyl group Chemical group 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 18
- 125000000547 substituted alkyl group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- -1 heterocyclo Chemical group 0.000 claims 12
- 125000006413 ring segment Chemical group 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- ZWBFLQKNWXAVDT-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound N1=C(N)C=C(N)C2=NC=CN21 ZWBFLQKNWXAVDT-UHFFFAOYSA-N 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- OHZBVIJOZXXXCU-VMQLAJLMSA-N N[C@@H]1CC[C@H](CC1)C1(C=C(C=2N(N1)C=CN=2)NC1=C(C=CC=C1F)F)N Chemical compound N[C@@H]1CC[C@H](CC1)C1(C=C(C=2N(N1)C=CN=2)NC1=C(C=CC=C1F)F)N OHZBVIJOZXXXCU-VMQLAJLMSA-N 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 206010063837 Reperfusion injury Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 230000036407 pain Effects 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- OMWMIYWQRVOUME-UHFFFAOYSA-N 6-(3-aminopiperidin-1-yl)-n-(4-ethoxyphenyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C1=CC(OCC)=CC=C1NC1=CC(N2CC(N)CCC2)=NN2C1=NC=C2 OMWMIYWQRVOUME-UHFFFAOYSA-N 0.000 claims 2
- JVLVATQOBJAKQU-UHFFFAOYSA-N 6-(3-aminopropyl)-8-N-(4-ethoxyphenyl)-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound NCCCC1(C=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)N JVLVATQOBJAKQU-UHFFFAOYSA-N 0.000 claims 2
- OTOBTQSDKOUPCV-UHFFFAOYSA-N 6-piperidin-3-yl-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound N1N2C=CN=C2C(N)=CC1(N)C1CCCNC1 OTOBTQSDKOUPCV-UHFFFAOYSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- TYEWIQQSOVFEQB-AQYVVDRMSA-N C1C[C@@H](N)CC[C@@H]1NC1=NN2C=CN=C2C(NC=2C=CC(NC(=O)C=3C(N(C=4C=CC(F)=CC=4)C=CC=3)=O)=CC=2)=C1 Chemical compound C1C[C@@H](N)CC[C@@H]1NC1=NN2C=CN=C2C(NC=2C=CC(NC(=O)C=3C(N(C=4C=CC(F)=CC=4)C=CC=3)=O)=CC=2)=C1 TYEWIQQSOVFEQB-AQYVVDRMSA-N 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- REFZOQLBWLWQJG-STFKQGPRSA-N N[C@@H]1CC[C@H](CC1)C1(C(=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)CC)N Chemical compound N[C@@H]1CC[C@H](CC1)C1(C(=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)CC)N REFZOQLBWLWQJG-STFKQGPRSA-N 0.000 claims 2
- RSUHAJFRFKIXPO-OEVKCDGTSA-N N[C@@H]1CC[C@H](CC1)C1(C(=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)Cl)N Chemical compound N[C@@H]1CC[C@H](CC1)C1(C(=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)Cl)N RSUHAJFRFKIXPO-OEVKCDGTSA-N 0.000 claims 2
- SLLIQXUELFHWMZ-LEWLWEGZSA-N N[C@@H]1CC[C@H](CC1)C1(C(=C(C=2N(N1)C=CN=2)NC1=CC=CC=C1)CC)N Chemical compound N[C@@H]1CC[C@H](CC1)C1(C(=C(C=2N(N1)C=CN=2)NC1=CC=CC=C1)CC)N SLLIQXUELFHWMZ-LEWLWEGZSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011152 Pemphigus Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 230000002917 arthritic effect Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 2
- 150000003053 piperidines Chemical class 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- RRXPOLXIYLTJJF-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-[4-(imidazo[1,2-b]pyridazin-8-ylamino)phenyl]-2-oxopiperidine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=CC(NC=3C4=NC=CN4N=CC=3)=CC=2)CCC1 RRXPOLXIYLTJJF-UHFFFAOYSA-N 0.000 claims 1
- NCDDUQLSGLCJJI-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-[4-(imidazo[1,2-b]pyridazin-8-ylamino)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=CC(NC=3C4=NC=CN4N=CC=3)=CC=2)=CC=C1 NCDDUQLSGLCJJI-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- CZYTUNVGDISHLR-UHFFFAOYSA-N 2-[1-[8-(4-ethoxyanilino)imidazo[1,2-b]pyridazin-6-yl]piperidin-4-yl]ethanol Chemical compound C1=CC(OCC)=CC=C1NC1=CC(N2CCC(CCO)CC2)=NN2C1=NC=C2 CZYTUNVGDISHLR-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- VPXNBUFYFHEGML-UHFFFAOYSA-N 4-[[6-[(4-aminocyclohexyl)amino]-7-methylimidazo[1,2-b]pyridazin-8-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=C(C)C(NC2CCC(N)CC2)=NN2C1=NC=C2 VPXNBUFYFHEGML-UHFFFAOYSA-N 0.000 claims 1
- CVXAFYLGEQSPPQ-UHFFFAOYSA-N 6-(2-aminoethyl)-8-N-(4-ethoxyphenyl)-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound NCCC1(C=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)N CVXAFYLGEQSPPQ-UHFFFAOYSA-N 0.000 claims 1
- CBOWJEIUBPOKHQ-UHFFFAOYSA-N 6-(3-aminocyclopentyl)-8-N-phenyl-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound NC1CC(CC1)C1(C=C(C=2N(N1)C=CN=2)NC1=CC=CC=C1)N CBOWJEIUBPOKHQ-UHFFFAOYSA-N 0.000 claims 1
- IYMHHVRRYYJNOK-UHFFFAOYSA-N 6-(3-aminopyrrolidin-1-yl)-n-(4-ethoxyphenyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C1=CC(OCC)=CC=C1NC1=CC(N2CC(N)CC2)=NN2C1=NC=C2 IYMHHVRRYYJNOK-UHFFFAOYSA-N 0.000 claims 1
- ACQOTGWOTFMBNO-UHFFFAOYSA-N 6-(4-aminobutyl)-8-N-(4-ethoxyphenyl)-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound NCCCCC1(C=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)N ACQOTGWOTFMBNO-UHFFFAOYSA-N 0.000 claims 1
- RFKGSCKPOUQZLM-UHFFFAOYSA-N 6-(furan-2-ylmethyl)-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound O1C(=CC=C1)CC1(C=C(C=2N(N1)C=CN=2)N)N RFKGSCKPOUQZLM-UHFFFAOYSA-N 0.000 claims 1
- IYMHHVRRYYJNOK-ZDUSSCGKSA-N 6-[(3s)-3-aminopyrrolidin-1-yl]-n-(4-ethoxyphenyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C1=CC(OCC)=CC=C1NC1=CC(N2C[C@@H](N)CC2)=NN2C1=NC=C2 IYMHHVRRYYJNOK-ZDUSSCGKSA-N 0.000 claims 1
- SSCCPHFJDLTXMT-UHFFFAOYSA-N 6-[2-(dimethylamino)ethyl]-8-N-(4-ethoxyphenyl)-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound CN(CCC1(C=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)N)C SSCCPHFJDLTXMT-UHFFFAOYSA-N 0.000 claims 1
- BKHBPNBPPLQSBP-UHFFFAOYSA-N 6-[4-[(4-aminocyclohexyl)methyl]cyclohexyl]-8-N-(4-ethoxyphenyl)-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound NC1CCC(CC1)CC1CCC(CC1)C1(C=C(C=2N(N1)C=CN=2)NC1=CC=C(C=C1)OCC)N BKHBPNBPPLQSBP-UHFFFAOYSA-N 0.000 claims 1
- XXTXMMMMXWVDHF-UHFFFAOYSA-N 6-n-(4-aminocyclohexyl)-8-n-(4-ethoxyphenyl)imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound C1=CC(OCC)=CC=C1NC1=CC(NC2CCC(N)CC2)=NN2C1=NC=C2 XXTXMMMMXWVDHF-UHFFFAOYSA-N 0.000 claims 1
- JBYKTGMHTPAFSV-UHFFFAOYSA-N 6-piperidin-4-yl-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound N1CCC(CC1)C1(C=C(C=2N(N1)C=CN=2)N)N JBYKTGMHTPAFSV-UHFFFAOYSA-N 0.000 claims 1
- PKQGGCSCOKKQRM-UHFFFAOYSA-N 6-pyrrolidin-3-yl-5H-imidazo[1,2-b]pyridazine-6,8-diamine Chemical compound N1CC(CC1)C1(C=C(C=2N(N1)C=CN=2)N)N PKQGGCSCOKKQRM-UHFFFAOYSA-N 0.000 claims 1
- UQLOIYALTVZLPF-UHFFFAOYSA-N 7-chloro-n-(4-ethoxyphenyl)-6-piperazin-1-ylimidazo[1,2-b]pyridazin-8-amine Chemical compound C1=CC(OCC)=CC=C1NC1=C(Cl)C(N2CCNCC2)=NN2C1=NC=C2 UQLOIYALTVZLPF-UHFFFAOYSA-N 0.000 claims 1
- PCDZINPUIMLKAY-UHFFFAOYSA-N 8-n-(4-ethoxyphenyl)-6-n-piperidin-3-ylimidazo[1,2-b]pyridazine-6,8-diamine Chemical compound C1=CC(OCC)=CC=C1NC1=CC(NC2CNCCC2)=NN2C1=NC=C2 PCDZINPUIMLKAY-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000036487 Arthropathies Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010055128 Autoimmune neutropenia Diseases 0.000 claims 1
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 241000713704 Bovine immunodeficiency virus Species 0.000 claims 1
- MAJKMMPTHCJHQW-UHFFFAOYSA-N C(=CC)C=1N=C2N(N=C(C=C2N)N)C1 Chemical compound C(=CC)C=1N=C2N(N=C(C=C2N)N)C1 MAJKMMPTHCJHQW-UHFFFAOYSA-N 0.000 claims 1
- PXYNPNJNRUKQGE-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C=1N=C2N(N=C(C=C2N)N)C1 Chemical compound C1(=CC=CC2=CC=CC=C12)C=1N=C2N(N=C(C=C2N)N)C1 PXYNPNJNRUKQGE-UHFFFAOYSA-N 0.000 claims 1
- MVDBIBQEHMDKGF-HDJSIYSDSA-N C1=C(O)C(S(=O)(=O)N(C)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 Chemical compound C1=C(O)C(S(=O)(=O)N(C)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 MVDBIBQEHMDKGF-HDJSIYSDSA-N 0.000 claims 1
- QUKAAEYQRASRQK-JCNLHEQBSA-N C1=CC(C(=O)N(C)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 QUKAAEYQRASRQK-JCNLHEQBSA-N 0.000 claims 1
- FWNWBUROLRVIBF-UAPYVXQJSA-N C1=CC(C(=O)N(CC)CC)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 FWNWBUROLRVIBF-UAPYVXQJSA-N 0.000 claims 1
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- GCLLKMQUUBAPQB-CTYIDZIISA-N C1=CC(NS(=O)(=O)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 GCLLKMQUUBAPQB-CTYIDZIISA-N 0.000 claims 1
- PDEFJRDSURAZNG-KOMQPUFPSA-N C1=CC(OCC)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2C#N Chemical compound C1=CC(OCC)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2C#N PDEFJRDSURAZNG-KOMQPUFPSA-N 0.000 claims 1
- HBJLBRUEPVJVMT-KOMQPUFPSA-N C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 HBJLBRUEPVJVMT-KOMQPUFPSA-N 0.000 claims 1
- HBJLBRUEPVJVMT-FZNQNYSPSA-N C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=CC(N[C@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=CC(N[C@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 HBJLBRUEPVJVMT-FZNQNYSPSA-N 0.000 claims 1
- NGOXSCLNXQYQBC-SAABIXHNSA-N C1=CC(S(=O)(=O)N(CC)CC)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1NC1=CC(N[C@@H]2CC[C@@H](N)CC2)=NN2C1=NC=C2 NGOXSCLNXQYQBC-SAABIXHNSA-N 0.000 claims 1
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|---|---|---|---|
| US71951905P | 2005-09-22 | 2005-09-22 | |
| US60/719,519 | 2005-09-22 | ||
| US11/524,996 US20070078136A1 (en) | 2005-09-22 | 2006-09-21 | Fused heterocyclic compounds useful as kinase modulators |
| US11/524,996 | 2006-09-21 | ||
| PCT/US2006/037056 WO2007038314A2 (en) | 2005-09-22 | 2006-09-22 | Fused heterocyclic compounds useful as kinase modulators |
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| JP2009509961A JP2009509961A (ja) | 2009-03-12 |
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| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| CR20230230A (es) | 2020-11-06 | 2023-07-27 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pdl1 y sales y formas cristalinas del mismo |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| KR20220170766A (ko) * | 2021-06-22 | 2022-12-30 | 주식회사 엘지화학 | 단백질 키나아제 억제제로서의 신규한 화합물 |
| EP4268824A1 (en) * | 2022-04-26 | 2023-11-01 | Manros Therapeutics | Imidazo[2,1-f][1,2,4]triazine derivatives useful as a medicament |
| WO2025199211A1 (en) * | 2024-03-19 | 2025-09-25 | Yale University | Imidazopyridines and imidazopyrimidines, and methods of using same |
| WO2025199359A1 (en) * | 2024-03-21 | 2025-09-25 | The Translational Genomics Research Institute | Methods of modulating cdk7 and flt3 using fused bicyclic compounds |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166851A (en) | 1977-05-16 | 1979-09-04 | Merck & Co., Inc. | Certain imidazo(1,2a)pyridine derivatives |
| CH635587A5 (fr) * | 1978-01-09 | 1983-04-15 | Aron Sa | Derives amines de pyrazolo (1,5-a) s.triazine, therapeutiquement actifs et leurs procedes de preparation. |
| FR2619818B1 (fr) * | 1987-09-01 | 1990-01-12 | Sanofi Sa | Imidazo (1,2-b) pyridazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US5260285A (en) | 1990-12-07 | 1993-11-09 | Merck & Co., Inc. | Substituted imidazopyridazines as angiotensin II antagonists |
| DE4327027A1 (de) | 1993-02-15 | 1994-08-18 | Bayer Ag | Imidazoazine |
| JP3621706B2 (ja) | 1996-08-28 | 2005-02-16 | ファイザー・インク | 置換された６，５―ヘテロ―二環式誘導体 |
| EP1345941A1 (fr) * | 2000-12-20 | 2003-09-24 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Inhibiteurs de kinases dependantes des cylines (cdk) et de la glycogene synthase kinase-3 (gsk-3) |
| FR2850653A1 (fr) * | 2003-02-04 | 2004-08-06 | Univ Pasteur | Derives de pyrazolotriazine, procede de preparation et utilisations |
| US7557110B2 (en) * | 2003-02-28 | 2009-07-07 | Teijin Pharma Limited | Pyrazolo[1,5-A] pyrimidine derivatives |
| DE10356579A1 (de) * | 2003-12-04 | 2005-07-07 | Merck Patent Gmbh | Aminderivate |
| AR047969A1 (es) | 2004-02-25 | 2006-03-15 | Schering Corp | Pirazolotriazinas como inhibidores de quinasa |
| US7537840B2 (en) * | 2004-08-05 | 2009-05-26 | H.B. Licensing & Financing, Inc. | Polyamide adhesive and articles including the same |
| US7557103B2 (en) * | 2005-04-05 | 2009-07-07 | Eli Lilly And Company | Imidazopyridazine compounds |
-
2006
- 2006-09-21 US US11/524,996 patent/US20070078136A1/en not_active Abandoned
- 2006-09-22 CA CA2623369A patent/CA2623369C/en active Active
- 2006-09-22 AU AU2006295439A patent/AU2006295439B2/en not_active Ceased
- 2006-09-22 ES ES06825074T patent/ES2402664T3/es active Active
- 2006-09-22 SI SI200631578T patent/SI1928879T1/sl unknown
- 2006-09-22 EP EP06825074A patent/EP1928879B1/en active Active
- 2006-09-22 BR BRPI0616393A patent/BRPI0616393B8/pt not_active IP Right Cessation
- 2006-09-22 KR KR1020147007661A patent/KR20140058645A/ko not_active Withdrawn
- 2006-09-22 PT PT68250745T patent/PT1928879E/pt unknown
- 2006-09-22 DK DK06825074.5T patent/DK1928879T3/da active
- 2006-09-22 NZ NZ566663A patent/NZ566663A/en not_active IP Right Cessation
- 2006-09-22 HR HRP20130155TT patent/HRP20130155T1/hr unknown
- 2006-09-22 TW TW095135141A patent/TWI441825B/zh not_active IP Right Cessation
- 2006-09-22 GE GEAP200610649A patent/GEP20104943B/en unknown
- 2006-09-22 JP JP2008532430A patent/JP5241498B2/ja not_active Expired - Fee Related
- 2006-09-22 EA EA200800873A patent/EA017632B1/ru not_active IP Right Cessation
- 2006-09-22 KR KR1020087009516A patent/KR101399766B1/ko not_active Expired - Fee Related
- 2006-09-22 WO PCT/US2006/037056 patent/WO2007038314A2/en not_active Ceased
- 2006-09-22 TW TW102124973A patent/TWI478925B/zh not_active IP Right Cessation
- 2006-09-22 PL PL06825074T patent/PL1928879T3/pl unknown
- 2006-09-22 PE PE2006001149A patent/PE20070520A1/es active IP Right Grant
- 2006-09-25 AR ARP060104153A patent/AR055177A1/es active IP Right Grant
-
2008
- 2008-03-10 NO NO20081231A patent/NO20081231L/no not_active Application Discontinuation
- 2008-03-18 IL IL190280A patent/IL190280A/en active IP Right Grant
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2013
- 2013-05-09 CY CY20131100374T patent/CY1114001T1/el unknown
- 2013-06-21 PH PH12013501329A patent/PH12013501329B1/en unknown
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