DE10238477A1 - Neue Purinderivate, deren Herstellung und deren Verwendung als Arzneimittel - Google Patents

Info

Publication number

DE10238477A1

DE10238477A1 DE10238477A DE10238477A DE10238477A1 DE 10238477 A1 DE10238477 A1 DE 10238477A1 DE 10238477 A DE10238477 A DE 10238477A DE 10238477 A DE10238477 A DE 10238477A DE 10238477 A1 DE10238477 A1 DE 10238477A1

Authority

DE

Germany

Prior art keywords

group

alkyl

amino

piperidin

dihydro

Prior art date

2002-08-22

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.)

Withdrawn

Links

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• Global Dossier
• DPMA
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• 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
• 239000003814 drug Substances 0.000 title claims abstract description 8
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims abstract 6
• 229940079593 drug Drugs 0.000 title claims description 3
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 79
• 239000000203 mixture Substances 0.000 claims abstract description 36
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 239000000651 prodrug Substances 0.000 claims abstract description 7
• 229940002612 prodrug Drugs 0.000 claims abstract description 7
• 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
• -1 Pyrrolidin-1-ylcarbonyl Chemical group 0.000 claims description 487
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
• 125000003277 amino group Chemical group 0.000 claims description 54
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 44
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 42
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
• 125000001624 naphthyl group Chemical group 0.000 claims description 39
• 125000004432 carbon atom Chemical group C* 0.000 claims description 30
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 27
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 22
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 239000011737 fluorine Substances 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 19
• 239000000460 chlorine Substances 0.000 claims description 18
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 17
• 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 17
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 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 description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000002541 furyl group Chemical group 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
• 229910052740 iodine Inorganic materials 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 6
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 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 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
• KYDFKPMXUILEAA-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-phenacylpurin-6-one Chemical compound C1C(N)CCCN1C(N1CC=2C=CC=CC=2)=NC2=C1C(=O)N(CC(=O)C=1C=CC=CC=1)C=N2 KYDFKPMXUILEAA-UHFFFAOYSA-N 0.000 claims description 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 5
• 150000003212 purines Chemical class 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 4
• KXEVVOQPEOZACT-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(benzylamino)-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1=CC=CC=C1 KXEVVOQPEOZACT-UHFFFAOYSA-N 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical group O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 claims description 3
• MLEOPWDMSPGAJV-UHFFFAOYSA-N 2-amino-8-(3-aminopiperidin-1-yl)-7-benzyl-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N)=NC=2N=C1N1CCCC(N)C1 MLEOPWDMSPGAJV-UHFFFAOYSA-N 0.000 claims description 3
• KXZCVZCPENDTBZ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-methyl-7-(3-methylbut-2-enyl)-2-(2-phenylethyl)purin-6-one Chemical compound CN1C(=O)C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N=C1CCC1=CC=CC=C1 KXZCVZCPENDTBZ-UHFFFAOYSA-N 0.000 claims description 3
• ZSJQMFQPGXOVJF-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-2-(benzylamino)-1-methyl-7-(3-methylbut-2-enyl)purin-6-one Chemical compound CN1C(=O)C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N=C1NCC1=CC=CC=C1 ZSJQMFQPGXOVJF-UHFFFAOYSA-N 0.000 claims description 3
• LIQQAKDINRZTHI-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-piperidin-1-ylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N3CCCCC3)=NC=2N=C1N1CCCC(N)C1 LIQQAKDINRZTHI-UHFFFAOYSA-N 0.000 claims description 3
• KHCNZQNITHNYGN-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C=NC=2N=C1N1CCCC(N)C1 KHCNZQNITHNYGN-UHFFFAOYSA-N 0.000 claims description 3
• MUJRWAFVKMBLQJ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(dimethylamino)-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N(C)C)=NC=2N=C1N1CCCC(N)C1 MUJRWAFVKMBLQJ-UHFFFAOYSA-N 0.000 claims description 3
• WRFSHVCQKQZCJT-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-[(4-fluorophenyl)methylamino]-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1=CC=C(F)C=C1 WRFSHVCQKQZCJT-UHFFFAOYSA-N 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 150000007524 organic acids Chemical class 0.000 claims description 3
• 235000005985 organic acids Nutrition 0.000 claims description 3
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• LNUIDEMUMXLMOV-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-8-(piperidin-4-ylmethyl)-3h-purin-6-one Chemical compound C=1C=C(F)C=CC=1CN1C=2C(O)=NC=NC=2N=C1CC1CCNCC1 LNUIDEMUMXLMOV-UHFFFAOYSA-N 0.000 claims description 2
• VEJJMWUFHYIMLI-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-8-[(1-methylpiperidin-4-yl)methyl]-3h-purin-6-one Chemical compound C1CN(C)CCC1CC(N1CC=2C=CC(F)=CC=2)=NC2=C1C(=O)NC=N2 VEJJMWUFHYIMLI-UHFFFAOYSA-N 0.000 claims description 2
• VLBIYRJVPOZOET-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-(2-phenylethylamino)purin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCCC1=CC=CC=C1 VLBIYRJVPOZOET-UHFFFAOYSA-N 0.000 claims description 2
• JRQQCSZVFBUCTP-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(cyclohexylmethylamino)-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1CCCCC1 JRQQCSZVFBUCTP-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 2
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• AVDIGJVYTMFEOU-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-1-methyl-2-methylsulfanyl-6-oxopurin-8-yl)piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CCCN(C1)C2=NC3=C(N2CC4=CC=CC=C4)C(=O)N(C(=N3)SC)C AVDIGJVYTMFEOU-UHFFFAOYSA-N 0.000 description 1
• OSWLKUBQCXCVHX-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-1-methyl-2-methylsulfinyl-6-oxopurin-8-yl)piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CCCN(C1)C2=NC3=C(N2CC4=CC=CC=C4)C(=O)N(C(=N3)S(=O)C)C OSWLKUBQCXCVHX-UHFFFAOYSA-N 0.000 description 1
• ZSWPNBVNIXQCOB-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-1-methyl-2-methylsulfonyl-6-oxopurin-8-yl)piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=C(N(C(C=2N1CC1=CC=CC=C1)=O)C)S(=O)(=O)C)=O ZSWPNBVNIXQCOB-UHFFFAOYSA-N 0.000 description 1
• POPCCAKPHCKRSJ-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-1-methyl-6-oxopurin-8-yl)piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CCCN(C1)C2=NC3=C(N2CC4=CC=CC=C4)C(=O)N(C=N3)C POPCCAKPHCKRSJ-UHFFFAOYSA-N 0.000 description 1
• VOELTXXMOPEISP-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-2-benzylsulfanyl-6-oxo-1H-purin-8-yl)piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=C(NC(C=2N1CC1=CC=CC=C1)=O)SCC1=CC=CC=C1)=O VOELTXXMOPEISP-UHFFFAOYSA-N 0.000 description 1
• OXSLBCYWGJJDJU-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-2-methylsulfanyl-6-oxo-1H-purin-8-yl)piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CCCN(C1)C2=NC3=C(N2CC4=CC=CC=C4)C(=O)NC(=N3)SC OXSLBCYWGJJDJU-UHFFFAOYSA-N 0.000 description 1
• DLAWTOCUWGGPMZ-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-6-oxo-1-phenacylpurin-8-yl)piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=CN(C(C=2N1CC1=CC=CC=C1)=O)CC(C1=CC=CC=C1)=O)=O DLAWTOCUWGGPMZ-UHFFFAOYSA-N 0.000 description 1
• QOCWGAXLFOFHOT-UHFFFAOYSA-N tert-butyl N-[1-(7-benzyl-6-oxo-1H-purin-8-yl)piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CCCN(C1)C2=NC3=C(N2CC4=CC=CC=C4)C(=O)NC=N3 QOCWGAXLFOFHOT-UHFFFAOYSA-N 0.000 description 1
• JLADOFPUANBJHO-UHFFFAOYSA-N tert-butyl N-[1-[1-methyl-7-(3-methylbut-1-enyl)-2-methylsulfanyl-6-oxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=C(N(C(C=2N1C=CC(C)C)=O)C)SC)=O JLADOFPUANBJHO-UHFFFAOYSA-N 0.000 description 1
• SCWRHWZTLTZWSQ-UHFFFAOYSA-N tert-butyl N-[1-[1-methyl-7-(3-methylbut-2-enyl)-6-oxo-2-(2-phenylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=C(N(C(C=2N1CC=C(C)C)=O)C)CCC1=CC=CC=C1)=O SCWRHWZTLTZWSQ-UHFFFAOYSA-N 0.000 description 1
• VFKLXKDPJOMWJV-UHFFFAOYSA-N tert-butyl N-[1-[7-benzyl-1-methyl-6-oxo-2-(2-phenylethylamino)purin-8-yl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=C(N(C(C=2N1CC1=CC=CC=C1)=O)C)NCCC1=CC=CC=C1)=O VFKLXKDPJOMWJV-UHFFFAOYSA-N 0.000 description 1
• NTODDGRCXGTIHR-UHFFFAOYSA-N tert-butyl N-[1-[7-benzyl-1-methyl-6-oxo-2-(2-phenylethylsulfanyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=C(N(C(C=2N1CC1=CC=CC=C1)=O)C)SCCC1=CC=CC=C1)=O NTODDGRCXGTIHR-UHFFFAOYSA-N 0.000 description 1
• PNDMOKXSDJRXQJ-UHFFFAOYSA-N tert-butyl N-[1-[7-benzyl-2-methylsulfanyl-6-oxo-1-(2-phenylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CN(CCC1)C1=NC=2N=C(N(C(C=2N1CC1=CC=CC=C1)=O)CCC1=CC=CC=C1)SC)=O PNDMOKXSDJRXQJ-UHFFFAOYSA-N 0.000 description 1
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• 229960005371 tolbutamide Drugs 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 238000002604 ultrasonography Methods 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229960001729 voglibose Drugs 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1