OA11071A - 2-(Purin-9-yl)-tetrahydrofuran-3,4-diol derivatives - Google Patents

Info

Publication number

OA11071A

OA11071A OA9900139A OA9900139A OA11071A OA 11071 A OA11071 A OA 11071A OA 9900139 A OA9900139 A OA 9900139A OA 9900139 A OA9900139 A OA 9900139A OA 11071 A OA11071 A OA 11071A

Authority

OA

OAPI

Prior art keywords

tetrahydro

purin

furan

tetrazol

ethylamino

Prior art date

1996-12-24

Links

• Espacenet
• Global Dossier
• Discuss

• YQUJSBYIKMQCIT-UHFFFAOYSA-N 2-purin-9-yloxolane-3,4-diol Chemical class OC1C(O)COC1N1C2=NC=NC=C2N=C1 YQUJSBYIKMQCIT-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 243
• 238000000034 method Methods 0.000 claims abstract description 37
• 230000008569 process Effects 0.000 claims abstract description 27
• 238000011282 treatment Methods 0.000 claims abstract description 17
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 208
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 92
• -1 azetidinyl,azepinyl Chemical group 0.000 claims description 53
• 238000006243 chemical reaction Methods 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 150000002431 hydrogen Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 4
• 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 description 4
• 238000010511 deprotection reaction Methods 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
• 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 3
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
• 125000002393 azetidinyl group Chemical group 0.000 claims description 2
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 150000002009 diols Chemical class 0.000 claims 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
• CDXIYBLQSCIRLM-GGRAJKFRSA-N (2r,3r,4s,5r)-2-[2-[(1-benzylpyrrolidin-3-yl)amino]-6-(2-phenylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4CN(CC=5C=CC=CC=5)CC4)=NC(NCCC=4C=CC=CC=4)=C3N=C2)O)=N1 CDXIYBLQSCIRLM-GGRAJKFRSA-N 0.000 claims 1
• HOXQRVLGKMUTKR-CKXMCULTSA-N (2r,3r,4s,5r)-2-[2-[2-(6-aminopyridin-2-yl)ethylamino]-6-(2,2-diphenylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=C(N)C=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 HOXQRVLGKMUTKR-CKXMCULTSA-N 0.000 claims 1
• CCYUSUQOSHABQD-OVDFTCDZSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCOCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 CCYUSUQOSHABQD-OVDFTCDZSA-N 0.000 claims 1
• VIFOOODREXJSEK-CKXMCULTSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 VIFOOODREXJSEK-CKXMCULTSA-N 0.000 claims 1
• RMVMOEOKCYTKAQ-YRIIQKNPSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(thian-4-ylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4CCSCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 RMVMOEOKCYTKAQ-YRIIQKNPSA-N 0.000 claims 1
• UFGDNNTWISONPP-QPXQOZNCSA-N (2r,3r,4s,5r)-2-[6-(benzylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(C)N=N4)O)C=NC3=C(NCC=3C=CC=CC=3)N=2)=C1 UFGDNNTWISONPP-QPXQOZNCSA-N 0.000 claims 1
• YMDKZQVBDPNYFC-QPXQOZNCSA-N (2r,3r,4s,5r)-2-[6-(cyclopentylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NC4CCCC4)=C3N=C2)O)=N1 YMDKZQVBDPNYFC-QPXQOZNCSA-N 0.000 claims 1
• GYAQEBPUPTYWEJ-CMCWBKRRSA-N (2r,3r,4s,5r)-2-[6-(pentan-3-ylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(2-propan-2-yltetrazol-5-yl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(N=N3)C(C)C)O)C=NC=2C(NC(CC)CC)=NC=1NCCN1CCCCC1 GYAQEBPUPTYWEJ-CMCWBKRRSA-N 0.000 claims 1
• WJKYPZJVAFYKCH-OVBHRPIXSA-N (2r,3r,4s,5r)-2-[6-amino-2-(3-bicyclo[2.2.1]heptanylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4C5CCC(C5)C4)=NC(N)=C3N=C2)O)=N1 WJKYPZJVAFYKCH-OVBHRPIXSA-N 0.000 claims 1
• JYSVYQLWXGLBHN-GRXQJBFDSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(3,4-dimethoxyphenyl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=C(OC)C(OC)=CC=4)=NC(N)=C3N=C2)O)=N1 JYSVYQLWXGLBHN-GRXQJBFDSA-N 0.000 claims 1
• MZLDNNGLLIUFPF-YUKKZQERSA-N CN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NC4CCCC4)=C3N=C2)O)=N1 Chemical compound CN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NC4CCCC4)=C3N=C2)O)=N1 MZLDNNGLLIUFPF-YUKKZQERSA-N 0.000 claims 1
• 241000764238 Isis Species 0.000 claims 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 239000000969 carrier Substances 0.000 claims 1
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
• ULYSABNRLLVZCE-UHFFFAOYSA-N furan-3,4-diol Chemical compound OC1=COC=C1O ULYSABNRLLVZCE-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 86
• 208000027866 inflammatory disease Diseases 0.000 abstract description 3
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• 238000002560 therapeutic procedure Methods 0.000 abstract 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 205
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
• 239000007787 solid Substances 0.000 description 120
• 239000000543 intermediate Substances 0.000 description 113
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
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