TW201343648A

TW201343648A - 作為ｉｇｆ－１ｒ／ｉｒ抑制劑之新５，８－二氫－６ｈ－吡唑并［３，４－ｈ］喹唑啉

作為ｉｇｆ－１ｒ／ｉｒ抑制劑之新５，８－二氫－６ｈ－吡唑并［３，４－ｈ］喹唑啉 Download PDF

Info

Publication number: TW201343648A
Authority: TW; Taiwan
Prior art keywords: group; alkyl; independently; different; compound
Prior art date: 2012-01-23

Application number

TW102102378A

Other languages

English (en)

Chinese (zh)

Inventor

Matthias Treu

Original Assignee

Boehringer Ingelheim Int

Priority date

2012-01-23

Filing date

2013-01-22

Publication date

2013-11-01

2013-01-22 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2013-11-01 Publication of TW201343648A publication Critical patent/TW201343648A/zh

Links

239000003112 inhibitor Substances 0.000 title description 19
LSJANTRUSCVIHS-UHFFFAOYSA-N 6,7-dihydro-5h-pyrazolo[3,4-h]quinazoline Chemical class N1=CN=C2C3=CNN=C3CCC2=C1 LSJANTRUSCVIHS-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 145
229910052799 carbon Inorganic materials 0.000 claims abstract description 66
238000011282 treatment Methods 0.000 claims abstract description 17
239000003814 drug Substances 0.000 claims abstract description 7
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 205
239000001257 hydrogen Substances 0.000 claims description 105
229910052739 hydrogen Inorganic materials 0.000 claims description 105
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 60
229910052736 halogen Inorganic materials 0.000 claims description 58
150000002367 halogens Chemical class 0.000 claims description 58
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 49
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 49
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
125000000623 heterocyclic group Chemical group 0.000 claims description 43
125000000392 cycloalkenyl group Chemical group 0.000 claims description 42
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125000001072 heteroaryl group Chemical group 0.000 claims description 39
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239000000203 mixture Substances 0.000 claims description 24
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
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125000003342 alkenyl group Chemical group 0.000 claims description 15
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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125000003118 aryl group Chemical group 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
238000002474 experimental method Methods 0.000 description 17
238000006467 substitution reaction Methods 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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125000004122 cyclic group Chemical group 0.000 description 14
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150000001412 amines Chemical class 0.000 description 12
239000000047 product Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
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125000004429 atom Chemical group 0.000 description 10
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125000001188 haloalkyl group Chemical group 0.000 description 10
125000001183 hydrocarbyl group Chemical group 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 7
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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235000019439 ethyl acetate Nutrition 0.000 description 6
125000000232 haloalkynyl group Chemical group 0.000 description 6
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
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