NO320422B1 - Substituerte 2-aryl-3-(heteroaryl)-imidazo[1,2a]pyrimidiner, med dertil horende farmasoytiske preparater samt metoder. - Google Patents
Substituerte 2-aryl-3-(heteroaryl)-imidazo[1,2a]pyrimidiner, med dertil horende farmasoytiske preparater samt metoder. Download PDFInfo
- Publication number
- NO320422B1 NO320422B1 NO20013419A NO20013419A NO320422B1 NO 320422 B1 NO320422 B1 NO 320422B1 NO 20013419 A NO20013419 A NO 20013419A NO 20013419 A NO20013419 A NO 20013419A NO 320422 B1 NO320422 B1 NO 320422B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- imidazo
- amine
- pyrimidin
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 92
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- -1 Br 2 Chemical compound 0.000 claims description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- BOJQXJHNUIWISM-UHFFFAOYSA-N imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C(N)C=CN2C=CN=C21 BOJQXJHNUIWISM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- OUYMDMNELLLCOG-UHFFFAOYSA-N 2-phenyl-3-(2-piperidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=C(N=CC=2)N2CCCCC2)=C1C1=CC=CC=C1 OUYMDMNELLLCOG-UHFFFAOYSA-N 0.000 claims description 2
- CECKFLSHKDGWGQ-UHFFFAOYSA-N 2-phenyl-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=CN=CC=2)=C1C1=CC=CC=C1 CECKFLSHKDGWGQ-UHFFFAOYSA-N 0.000 claims description 2
- YGBTVRUWFYRCNE-UHFFFAOYSA-N 3-(2-methoxypyrimidin-4-yl)-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound COC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 YGBTVRUWFYRCNE-UHFFFAOYSA-N 0.000 claims description 2
- RNWWNLBSAXIAMZ-UHFFFAOYSA-N 3-(2-methylsulfonylpyrimidin-4-yl)-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound CS(=O)(=O)C1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 RNWWNLBSAXIAMZ-UHFFFAOYSA-N 0.000 claims description 2
- YWQVMSDKUMRDSW-UHFFFAOYSA-N 3-pyrimidin-4-yl-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=CN=CC=2)=C1C1=CC=CC(C(F)(F)F)=C1 YWQVMSDKUMRDSW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- QRDAPCMJAOQZSU-KQQUZDAGSA-N (e)-3-[4-[(e)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methylpyrrol-2-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(\C=C\C(=O)NO)N(C)C=C1\C=C\C(=O)C1=CC=CC(F)=C1 QRDAPCMJAOQZSU-KQQUZDAGSA-N 0.000 claims 3
- CYSWUSAYJNCAKA-FYJFLYSWSA-N ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O Chemical compound ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O CYSWUSAYJNCAKA-FYJFLYSWSA-N 0.000 claims 2
- SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 claims 2
- QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- VPMIAOSOTOODMY-KJAPKAAFSA-N (4r)-6-[(e)-2-[6-tert-butyl-4-(4-fluorophenyl)-2-propan-2-ylpyridin-3-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1/C=C/C=1C(C(C)C)=NC(C(C)(C)C)=CC=1C1=CC=C(F)C=C1 VPMIAOSOTOODMY-KJAPKAAFSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- VAVHMEQFYYBAPR-ITWZMISCSA-N (e,3r,5s)-7-[4-(4-fluorophenyl)-1-phenyl-2-propan-2-ylpyrrol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=CN1C1=CC=CC=C1 VAVHMEQFYYBAPR-ITWZMISCSA-N 0.000 claims 1
- KVSJCXDUYDCCHX-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(Cl)=C1 KVSJCXDUYDCCHX-UHFFFAOYSA-N 0.000 claims 1
- YQSFQNMEKQXOET-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(F)=C1 YQSFQNMEKQXOET-UHFFFAOYSA-N 0.000 claims 1
- RFKYUEFCPXYIHY-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=CN=CC=2)=C1C1=CC=C(F)C=C1 RFKYUEFCPXYIHY-UHFFFAOYSA-N 0.000 claims 1
- SXMGPKIFJDLHQD-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-quinolin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C3=CC=CC=C3N=CC=2)=C1C1=CC=C(F)C=C1 SXMGPKIFJDLHQD-UHFFFAOYSA-N 0.000 claims 1
- WYGVFMIQQCLMNX-UHFFFAOYSA-N 3-(2-methylsulfanylpyrimidin-4-yl)-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 WYGVFMIQQCLMNX-UHFFFAOYSA-N 0.000 claims 1
- UGOQPKUREUTQEZ-UHFFFAOYSA-N 3-[2-(benzylamino)pyridin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=C(NCC=3C=CC=CC=3)N=CC=2)=C1C1=CC=C(F)C=C1 UGOQPKUREUTQEZ-UHFFFAOYSA-N 0.000 claims 1
- KKPXTSJLILQNDB-UHFFFAOYSA-N 3-[2-(benzylamino)pyridin-4-yl]-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=C(NCC=3C=CC=CC=3)N=CC=2)=C1C1=CC=CC(C(F)(F)F)=C1 KKPXTSJLILQNDB-UHFFFAOYSA-N 0.000 claims 1
- FYTHWTYFVMCJNL-HNNXBMFYSA-N 3-[2-[[(1s)-1-cyclohexylethyl]amino]pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N([C@@H](C)C1CCCCC1)C(N=1)=NC=CC=1C(N1C=CC(N)=NC1=N1)=C1C1=CC=C(F)C=C1 FYTHWTYFVMCJNL-HNNXBMFYSA-N 0.000 claims 1
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Landscapes
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US16470099P | 1999-11-10 | 1999-11-10 | |
PCT/US2000/029875 WO2001034605A1 (en) | 1999-11-10 | 2000-10-27 | SUBSTITUTED 2-ARYL-3-(HETEROARYL)-IMIDAZO[1,2-a]PYRIMIDINES, AND RELATED PHARMACEUTICAL COMPOSITIONS AND METHODS |
Publications (3)
Publication Number | Publication Date |
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NO20013419D0 NO20013419D0 (no) | 2001-07-10 |
NO20013419L NO20013419L (no) | 2001-08-27 |
NO320422B1 true NO320422B1 (no) | 2005-12-05 |
Family
ID=22595694
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20013419A NO320422B1 (no) | 1999-11-10 | 2001-07-10 | Substituerte 2-aryl-3-(heteroaryl)-imidazo[1,2a]pyrimidiner, med dertil horende farmasoytiske preparater samt metoder. |
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US (1) | US6610697B1 (id) |
EP (1) | EP1140939B1 (id) |
JP (1) | JP2003513977A (id) |
KR (1) | KR20010089805A (id) |
CN (1) | CN1255406C (id) |
AR (1) | AR026410A1 (id) |
AT (1) | ATE288915T1 (id) |
AU (1) | AU784484B2 (id) |
BG (1) | BG65106B1 (id) |
BR (1) | BR0007447A (id) |
CA (1) | CA2361139A1 (id) |
CZ (1) | CZ20012494A3 (id) |
DE (1) | DE60018037T2 (id) |
ES (1) | ES2237470T3 (id) |
HK (1) | HK1043591B (id) |
HU (1) | HUP0200207A3 (id) |
ID (1) | ID29514A (id) |
IL (1) | IL144238A (id) |
MX (1) | MXPA01007019A (id) |
NO (1) | NO320422B1 (id) |
NZ (1) | NZ512957A (id) |
PL (1) | PL348924A1 (id) |
PT (1) | PT1140939E (id) |
RU (1) | RU2264403C2 (id) |
SK (1) | SK9892001A3 (id) |
UA (1) | UA70350C2 (id) |
WO (1) | WO2001034605A1 (id) |
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