CA2506720A1 - New xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions - Google Patents

Info

Publication number

CA2506720A1

CA2506720A1 CA002506720A CA2506720A CA2506720A1 CA 2506720 A1 CA2506720 A1 CA 2506720A1 CA 002506720 A CA002506720 A CA 002506720A CA 2506720 A CA2506720 A CA 2506720A CA 2506720 A1 CA2506720 A1 CA 2506720A1

Authority

CA

Canada

Prior art keywords

group

alkyl

amino

substituted

methyl

Prior art date

2002-11-21

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
• 238000002360 preparation method Methods 0.000 title description 13
• 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title description 2
• 239000000203 mixture Substances 0.000 claims abstract description 32
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 229940002612 prodrug Drugs 0.000 claims abstract description 5
• 239000000651 prodrug Substances 0.000 claims abstract description 5
• -1 nitro, amino Chemical group 0.000 claims description 404
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 67
• 150000001875 compounds Chemical class 0.000 claims description 60
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
• 125000003277 amino group Chemical group 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• 239000000460 chlorine Substances 0.000 claims description 26
• 229910052801 chlorine Inorganic materials 0.000 claims description 26
• 229910052731 fluorine Inorganic materials 0.000 claims description 26
• 150000001721 carbon Chemical group 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 239000011737 fluorine Substances 0.000 claims description 24
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
• 125000001153 fluoro group Chemical group F* 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 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 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
• 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 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
• 125000006239 protecting group Chemical group 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 238000006243 chemical reaction Methods 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 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 8
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 229910052740 iodine Inorganic materials 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
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
• 125000005605 benzo 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
• 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
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 4
• 150000007524 organic acids Chemical class 0.000 claims description 4
• 235000005985 organic acids Nutrition 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
• VUKXQZGSRXXAPO-GOSISDBHSA-N (3-methoxyphenyl)methyl 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]acetate Chemical compound COC1=CC=CC(COC(=O)CN2C(C=3N(CC#CC)C(N4C[C@H](N)CCC4)=NC=3N(C)C2=O)=O)=C1 VUKXQZGSRXXAPO-GOSISDBHSA-N 0.000 claims description 3
• PKHOOQZNCCPPCE-QGZVFWFLSA-N (3-nitrophenyl)methyl 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]acetate Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)OCC1=CC=CC([N+]([O-])=O)=C1 PKHOOQZNCCPPCE-QGZVFWFLSA-N 0.000 claims description 3
• AJQWEUVMERJMEM-UHFFFAOYSA-N 2-[8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-(3-cyanophenyl)acetamide Chemical compound O=C1C=2N(CC#CC)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NC1=CC=CC(C#N)=C1 AJQWEUVMERJMEM-UHFFFAOYSA-N 0.000 claims description 3
• ULWHKPMSQYESJY-UHFFFAOYSA-N 2-[8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-(4-cyanophenyl)acetamide Chemical compound O=C1C=2N(CC#CC)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NC1=CC=C(C#N)C=C1 ULWHKPMSQYESJY-UHFFFAOYSA-N 0.000 claims description 3
• WYVOKGNCONNTOF-QGZVFWFLSA-N 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-(2-methylphenyl)acetamide Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NC1=CC=CC=C1C WYVOKGNCONNTOF-QGZVFWFLSA-N 0.000 claims description 3
• ZXEFZPQBEOGJKR-OAHLLOKOSA-N 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-(2-nitrophenyl)acetamide Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NC1=CC=CC=C1[N+]([O-])=O ZXEFZPQBEOGJKR-OAHLLOKOSA-N 0.000 claims description 3
• MKMKEGODBYOJBS-OAHLLOKOSA-N 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-pyridin-2-ylacetamide Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NC1=CC=CC=N1 MKMKEGODBYOJBS-OAHLLOKOSA-N 0.000 claims description 3
• XRFZJHMDBXXHGI-OAHLLOKOSA-N 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-pyridin-3-ylacetamide Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NC1=CC=CN=C1 XRFZJHMDBXXHGI-OAHLLOKOSA-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
• 150000001412 amines Chemical class 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• VXAJESROSSBINV-UHFFFAOYSA-N n-[(2-aminophenyl)methyl]-2-[8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]acetamide Chemical compound O=C1C=2N(CC#CC)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NCC1=CC=CC=C1N VXAJESROSSBINV-UHFFFAOYSA-N 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
• 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
• UDINXHZIKSBWIE-MRXNPFEDSA-N 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(=O)CN1C(=O)C(N(CC#CC)C(N2C[C@H](N)CCC2)=N2)=C2N(C)C1=O UDINXHZIKSBWIE-MRXNPFEDSA-N 0.000 claims description 2
• AAXBIHLUKLGZGA-GOSISDBHSA-N 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-benzylacetamide Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NCC1=CC=CC=C1 AAXBIHLUKLGZGA-GOSISDBHSA-N 0.000 claims description 2
• WNFMNBUPHOZHQQ-MRXNPFEDSA-N 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]-n-phenylacetamide Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)NC1=CC=CC=C1 WNFMNBUPHOZHQQ-MRXNPFEDSA-N 0.000 claims description 2
• 125000004610 3,4-dihydro-4-oxo-quinazolinyl group Chemical group O=C1NC(=NC2=CC=CC=C12)* 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
• MTLIDTOJEKAJKQ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(2-oxo-3-phenoxypropyl)purine-2,6-dione Chemical compound O=C1C=2N(CC#CC)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CC(=O)COC1=CC=CC=C1 MTLIDTOJEKAJKQ-UHFFFAOYSA-N 0.000 claims description 2
• NPURMCMDCVWIMO-HXUWFJFHSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-1-[2-(3,4-dihydro-1h-isoquinolin-2-yl)-2-oxoethyl]-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC(=O)N3CC4=CC=CC=C4CC3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 NPURMCMDCVWIMO-HXUWFJFHSA-N 0.000 claims description 2
• HXIYTBFSBWDGMW-LJQANCHMSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-1-[2-(3,4-dihydro-2h-quinolin-1-yl)-2-oxoethyl]-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC(=O)N3C4=CC=CC=C4CCC3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 HXIYTBFSBWDGMW-LJQANCHMSA-N 0.000 claims description 2
• 102000055006 Calcitonin Human genes 0.000 claims description 2
• 108060001064 Calcitonin Proteins 0.000 claims description 2
• 208000001132 Osteoporosis Diseases 0.000 claims description 2
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• 206010003246 arthritis Diseases 0.000 claims description 2
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 2
• OOWPFHYABWXYSC-GOSISDBHSA-N benzyl 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]acetate Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)OCC1=CC=CC=C1 OOWPFHYABWXYSC-GOSISDBHSA-N 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
• 229960004015 calcitonin Drugs 0.000 claims description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• BZXABUUYZDJOQF-QGZVFWFLSA-N pyridin-3-ylmethyl 2-[8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-1-yl]acetate Chemical compound O=C1C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N(C)C(=O)N1CC(=O)OCC1=CC=CN=C1 BZXABUUYZDJOQF-QGZVFWFLSA-N 0.000 claims description 2
• 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 2
• 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims description 2
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
• 238000002054 transplantation Methods 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 15
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 13
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 12
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
• 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 3
• 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
• 239000000969 carrier Substances 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• 125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 claims 1
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims 1
• 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims 1
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
• 125000004103 aminoalkyl group Chemical group 0.000 claims 1
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