EA024251B1 - 8-[-3-аминопиперидин-1-ил]ксантины, способ их получения и их применение в качестве лекарственных средств - Google Patents
8-[-3-аминопиперидин-1-ил]ксантины, способ их получения и их применение в качестве лекарственных средств Download PDFInfo
- Publication number
- EA024251B1 EA024251B1 EA201001167A EA201001167A EA024251B1 EA 024251 B1 EA024251 B1 EA 024251B1 EA 201001167 A EA201001167 A EA 201001167A EA 201001167 A EA201001167 A EA 201001167A EA 024251 B1 EA024251 B1 EA 024251B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methyl
- xanthine
- mass spectrum
- tert
- silica gel
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title description 5
- 239000003814 drug Substances 0.000 title description 4
- 230000008569 process Effects 0.000 title description 4
- WNHHLYZOSOUUQW-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3,7-dihydropurine-2,6-dione Chemical class C1C(N)CCCN1C(N1)=NC2=C1C(=O)NC(=O)N2 WNHHLYZOSOUUQW-UHFFFAOYSA-N 0.000 title 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims abstract description 379
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 874
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 789
- -1 4-methyl-2-quinazolinylmethyl Chemical group 0.000 claims description 788
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 669
- 229940075420 xanthine Drugs 0.000 claims description 187
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 181
- 150000001875 compounds Chemical class 0.000 claims description 154
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 113
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 45
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 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 8
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 77
- 150000003839 salts Chemical class 0.000 abstract description 33
- 230000000694 effects Effects 0.000 abstract description 13
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 229940002612 prodrug Drugs 0.000 abstract description 6
- 239000000651 prodrug Substances 0.000 abstract description 6
- 230000000144 pharmacologic effect Effects 0.000 abstract description 4
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 abstract description 3
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 abstract 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 abstract 2
- 238000001819 mass spectrum Methods 0.000 description 552
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 409
- 239000000741 silica gel Substances 0.000 description 409
- 229910002027 silica gel Inorganic materials 0.000 description 409
- 238000006243 chemical reaction Methods 0.000 description 118
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 95
- 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 description 84
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- 239000003208 petroleum Substances 0.000 description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 58
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 53
- 235000011114 ammonium hydroxide Nutrition 0.000 description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 50
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
- 239000000243 solution Substances 0.000 description 48
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 239000000047 product Substances 0.000 description 43
- 239000011541 reaction mixture Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 229910000027 potassium carbonate Inorganic materials 0.000 description 25
- 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 description 23
- 239000003480 eluent Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 239000012071 phase Substances 0.000 description 21
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 20
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 239000012043 crude product Substances 0.000 description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 230000002441 reversible effect Effects 0.000 description 11
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 239000012448 Lithium borohydride Substances 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
- LJSHCUGJRJMUOB-UHFFFAOYSA-N 1-(chloromethyl)-3-(trifluoromethyl)-3,4-dihydroisoquinoline Chemical compound C1=CC=C2C(CCl)=NC(C(F)(F)F)CC2=C1 LJSHCUGJRJMUOB-UHFFFAOYSA-N 0.000 description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- DAXHWZGBXYAIQY-UHFFFAOYSA-N 2-[(8-chloro-1-methyl-2,6-dioxo-3h-purin-7-yl)methyl]benzonitrile Chemical compound C1=2C(=O)N(C)C(=O)NC=2N=C(Cl)N1CC1=CC=CC=C1C#N DAXHWZGBXYAIQY-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000004610 3,4-dihydro-4-oxo-quinazolinyl group Chemical group O=C1NC(=NC2=CC=CC=C12)* 0.000 description 3
- ZVABNIBQTGBRIS-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-[(4-oxo-3h-phthalazin-1-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(=O)NN=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(N)C1 ZVABNIBQTGBRIS-UHFFFAOYSA-N 0.000 description 3
- IGTORBVZKSZOKS-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-(3-methylbut-2-enyl)-1-phenacyl-3h-purine-2,6-dione Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2NC(=O)N1CC(=O)C1=CC=CC=C1 IGTORBVZKSZOKS-UHFFFAOYSA-N 0.000 description 3
- MFXXJJGWXSHSBQ-UHFFFAOYSA-N 8-chloro-3-methyl-7-(3-methylbut-2-enyl)purine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=C(Cl)N2CC=C(C)C MFXXJJGWXSHSBQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241000208202 Linaceae Species 0.000 description 3
- 235000004431 Linum usitatissimum Nutrition 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 239000012131 assay buffer Substances 0.000 description 3
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 3
- YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000002464 receptor antagonist Substances 0.000 description 3
- 229940044551 receptor antagonist Drugs 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
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- UAYUQVIWQVWNBO-UHFFFAOYSA-N tert-butyl 7-[2-[7-but-2-ynyl-3-methyl-8-[3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxopurin-1-yl]acetyl]indole-1-carboxylate Chemical compound N=1C=2N(C)C(=O)N(CC(=O)C=3C=4N(C(=O)OC(C)(C)C)C=CC=4C=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 UAYUQVIWQVWNBO-UHFFFAOYSA-N 0.000 description 1
- ZXOCBYSRQPGCSX-UHFFFAOYSA-N tert-butyl 7-acetylindole-1-carboxylate Chemical compound CC(=O)C1=CC=CC2=C1N(C(=O)OC(C)(C)C)C=C2 ZXOCBYSRQPGCSX-UHFFFAOYSA-N 0.000 description 1
- CRHUPTVRQCUQPW-UHFFFAOYSA-N tert-butyl N-[1-[1-(1,3-benzoxazol-2-ylmethyl)-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3OC4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 CRHUPTVRQCUQPW-UHFFFAOYSA-N 0.000 description 1
- MOCVKWMGQXSVRI-UHFFFAOYSA-N tert-butyl N-[1-[7-but-2-ynyl-3-methyl-1-[(3-methyl-4-oxoquinazolin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N(C(=O)C4=CC=CC=C4N=3)C)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 MOCVKWMGQXSVRI-UHFFFAOYSA-N 0.000 description 1
- ACBRZJMXXPNWSU-UHFFFAOYSA-N tert-butyl n-[1-(7-but-2-ynyl-3-cyclopropyl-2,6-dioxopurin-8-yl)piperidin-3-yl]carbamate Chemical compound O=C1NC(=O)C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1C1CC1 ACBRZJMXXPNWSU-UHFFFAOYSA-N 0.000 description 1
- JUNVOMCTDDZUMJ-UHFFFAOYSA-N tert-butyl n-[1-[1-(1,4-dihydrocinnolin-4-ylmethyl)-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC3C4=CC=CC=C4NN=C3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 JUNVOMCTDDZUMJ-UHFFFAOYSA-N 0.000 description 1
- YGTIPELGJHFPHX-UHFFFAOYSA-N tert-butyl n-[1-[1-(1-benzothiophen-3-ylmethyl)-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4SC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 YGTIPELGJHFPHX-UHFFFAOYSA-N 0.000 description 1
- MSJTYGJIAUBBNE-UHFFFAOYSA-N tert-butyl n-[1-[1-(1h-benzimidazol-2-ylmethyl)-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3NC4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 MSJTYGJIAUBBNE-UHFFFAOYSA-N 0.000 description 1
- QENFSKREOVBEHA-UHFFFAOYSA-N tert-butyl n-[1-[1-(2-cyclohexyl-2-oxoethyl)-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1CCCCC1 QENFSKREOVBEHA-UHFFFAOYSA-N 0.000 description 1
- BHIPZMQUGZFQMJ-UHFFFAOYSA-N tert-butyl n-[1-[1-(3,3-dimethyl-2-oxobutyl)-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC(=O)C(C)(C)C)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 BHIPZMQUGZFQMJ-UHFFFAOYSA-N 0.000 description 1
- UBNXHBMUEWYBEO-UHFFFAOYSA-N tert-butyl n-[1-[1-(cinnolin-4-ylmethyl)-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4N=NC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 UBNXHBMUEWYBEO-UHFFFAOYSA-N 0.000 description 1
- MQGJECLSPFZMLG-UHFFFAOYSA-N tert-butyl n-[1-[1-[(1-benzylbenzimidazol-2-yl)methyl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC1=NC2=CC=CC=C2N1CC1=CC=CC=C1 MQGJECLSPFZMLG-UHFFFAOYSA-N 0.000 description 1
- XCACLHCSWYUXIY-UHFFFAOYSA-N tert-butyl n-[1-[1-[(4-aminoquinazolin-2-yl)methyl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(N)N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 XCACLHCSWYUXIY-UHFFFAOYSA-N 0.000 description 1
- GTEIBIXQCXUNEB-UHFFFAOYSA-N tert-butyl n-[1-[1-[(4-bromo-3-methoxyisoquinolin-1-yl)methyl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=12C=CC=CC2=C(Br)C(OC)=NC=1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 GTEIBIXQCXUNEB-UHFFFAOYSA-N 0.000 description 1
- WFOUXHIOVMYZTP-UHFFFAOYSA-N tert-butyl n-[1-[1-[(5-aminoisoquinolin-1-yl)methyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC(N)=C4C=CN=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 WFOUXHIOVMYZTP-UHFFFAOYSA-N 0.000 description 1
- BKNRGNALQKCBFP-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(1,3-benzodioxol-4-yl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC(=O)C=3C=4OCOC=4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 BKNRGNALQKCBFP-UHFFFAOYSA-N 0.000 description 1
- AMEGIGLDGRAOOW-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2,3-dihydro-1,4-benzodioxin-5-yl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC(=O)C=3C=4OCCOC=4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 AMEGIGLDGRAOOW-UHFFFAOYSA-N 0.000 description 1
- KLLYGXTZIAHRDW-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2,3-dimethoxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=CC(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1OC KLLYGXTZIAHRDW-UHFFFAOYSA-N 0.000 description 1
- HLKSDBJNXDJXMD-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2,6-dimethoxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=CC(OC)=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O HLKSDBJNXDJXMD-UHFFFAOYSA-N 0.000 description 1
- CIKIIRTZGHXTED-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2-acetamidophenyl)-2-oxoethyl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1NC(C)=O CIKIIRTZGHXTED-UHFFFAOYSA-N 0.000 description 1
- BCCLFHKSZGAMGH-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2-amino-3-methoxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=CC(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1N BCCLFHKSZGAMGH-UHFFFAOYSA-N 0.000 description 1
- LHTAXYAKCYGEIT-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2-aminophenyl)-2-oxoethyl]-7-(cyclopenten-1-ylmethyl)-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1CCCC=1CN1C=2C(=O)N(CC(=O)C=3C(=CC=CC=3)N)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 LHTAXYAKCYGEIT-UHFFFAOYSA-N 0.000 description 1
- LFEUCHARDAQECR-VOTSOKGWSA-N tert-butyl n-[1-[1-[2-(2-aminophenyl)-2-oxoethyl]-7-[(e)-but-2-enyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(C/C=C/C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1N LFEUCHARDAQECR-VOTSOKGWSA-N 0.000 description 1
- XYWFRPTZXDEQMC-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2-aminophenyl)-2-oxoethyl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1N XYWFRPTZXDEQMC-UHFFFAOYSA-N 0.000 description 1
- SVCIAUAMLPSGKA-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(3-aminophenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC(N)=C1 SVCIAUAMLPSGKA-UHFFFAOYSA-N 0.000 description 1
- QHYSLXZYAJYAFJ-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(3-hydroxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC(O)=C1 QHYSLXZYAJYAFJ-UHFFFAOYSA-N 0.000 description 1
- DSBRUGDRJWUFPE-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(dimethylamino)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CC(C)=CCN1C=2C(=O)N(CC(=O)N(C)C)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 DSBRUGDRJWUFPE-UHFFFAOYSA-N 0.000 description 1
- PXUXSGRAHCFXTK-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[2-(2-amino-2-oxoethoxy)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1OCC(N)=O PXUXSGRAHCFXTK-UHFFFAOYSA-N 0.000 description 1
- YVGYSCHSVDDVCR-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[2-(2-amino-2-oxoethoxy)phenyl]-2-oxoethyl]-7-but-2-ynyl-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1OCC(N)=O YVGYSCHSVDDVCR-UHFFFAOYSA-N 0.000 description 1
- CQEHOONTOMDVDN-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[2-(cyanomethylamino)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1NCC#N CQEHOONTOMDVDN-UHFFFAOYSA-N 0.000 description 1
- OLVKTQYDNBUFLU-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[2-(dimethylcarbamoyl)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CN(C)C(=O)C1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O OLVKTQYDNBUFLU-UHFFFAOYSA-N 0.000 description 1
- AGSCCEVBVOJAHA-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[2-(ethoxycarbonylcarbamoylamino)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CCOC(=O)NC(=O)NC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O AGSCCEVBVOJAHA-UHFFFAOYSA-N 0.000 description 1
- IQFDXLBPQDSLPF-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[2-(methoxycarbonylamino)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC(=O)NC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O IQFDXLBPQDSLPF-UHFFFAOYSA-N 0.000 description 1
- OGIWERHYAAGQBX-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[3-(2-chloroethylcarbamoylamino)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC(NC(=O)NCCCl)=C1 OGIWERHYAAGQBX-UHFFFAOYSA-N 0.000 description 1
- JZWAANDVSRNUDO-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[3-(dimethylcarbamoyl)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CN(C)C(=O)C1=CC=CC(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1 JZWAANDVSRNUDO-UHFFFAOYSA-N 0.000 description 1
- ATJMLNSSJLTHOF-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyanomethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-1-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(CC#N)C(=O)N1CC(=O)C1=CC=CC=C1 ATJMLNSSJLTHOF-UHFFFAOYSA-N 0.000 description 1
- PDXDKSMSGPXNPL-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyanomethyl)-7-[(2-cyanophenyl)methyl]-1-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)N(C)C(=O)N(CC#N)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 PDXDKSMSGPXNPL-UHFFFAOYSA-N 0.000 description 1
- WAXGXIZMFYWMHY-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-1-[2-[2-[2-(methylamino)-2-oxoethoxy]phenyl]-2-oxoethyl]-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CNC(=O)COC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O WAXGXIZMFYWMHY-UHFFFAOYSA-N 0.000 description 1
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- LDEWQWALLVFFMP-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[(3-methyl-4-oxophthalazin-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(=O)N(C)N=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 LDEWQWALLVFFMP-UHFFFAOYSA-N 0.000 description 1
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- ZGXDAHIEHZUYON-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[(5-nitroisoquinolin-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC(=C4C=CN=3)[N+]([O-])=O)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 ZGXDAHIEHZUYON-UHFFFAOYSA-N 0.000 description 1
- MVCSMSRQEQLNDU-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[2-(2-nitrophenyl)-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1[N+]([O-])=O MVCSMSRQEQLNDU-UHFFFAOYSA-N 0.000 description 1
- ZZGVKHPZAZCPGU-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[2-(3-methyl-2-oxo-1,3-benzoxazol-7-yl)-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC(=O)C=3C=4OC(=O)N(C)C=4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 ZZGVKHPZAZCPGU-UHFFFAOYSA-N 0.000 description 1
- MRKWUHOQTGAYBT-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[2-(3-methylsulfinylphenyl)-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC(S(C)=O)=C1 MRKWUHOQTGAYBT-UHFFFAOYSA-N 0.000 description 1
- XHHMKLPBWRTDMA-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[2-(3-methylsulfonylphenyl)-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC(S(C)(=O)=O)=C1 XHHMKLPBWRTDMA-UHFFFAOYSA-N 0.000 description 1
- UXPRJJXCAJAQKJ-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[2-[2-(2-methylpropanoylamino)phenyl]-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CC(C)C(=O)NC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O UXPRJJXCAJAQKJ-UHFFFAOYSA-N 0.000 description 1
- LCKCBSSZBQWUCY-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[2-[2-(morpholine-4-carbonyl)phenyl]-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1C(=O)N1CCOCC1 LCKCBSSZBQWUCY-UHFFFAOYSA-N 0.000 description 1
- WWGPVNRUXJPEDB-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[2-[3-(morpholine-4-carbonyl)phenyl]-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C(C=1)=CC=CC=1C(=O)N1CCOCC1 WWGPVNRUXJPEDB-UHFFFAOYSA-N 0.000 description 1
- RAAJSNZAJQGURT-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-(1-oxo-1-phenylpropan-2-yl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C=2N=C(N3CC(CCC3)NC(=O)OC(C)(C)C)N(CC=C(C)C)C=2C(=O)N1C(C)C(=O)C1=CC=CC=C1 RAAJSNZAJQGURT-UHFFFAOYSA-N 0.000 description 1
- UOQHAXFRWQZCPE-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-(2-oxo-2-piperidin-1-ylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)N1CCCCC1 UOQHAXFRWQZCPE-UHFFFAOYSA-N 0.000 description 1
- HKRFHNFHWBPSDR-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-(2-oxo-2-pyrrolidin-1-ylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)N1CCCC1 HKRFHNFHWBPSDR-UHFFFAOYSA-N 0.000 description 1
- GUYRUBCPOQQSQG-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(ON=1)=NC=1C1=CC=CC=C1 GUYRUBCPOQQSQG-UHFFFAOYSA-N 0.000 description 1
- IWEJHYUZDNSOEF-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-[(4-oxo-3h-phthalazin-1-yl)methyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(=O)NN=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 IWEJHYUZDNSOEF-UHFFFAOYSA-N 0.000 description 1
- QEFPUNCCUIUVKM-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-[(4-phenylpyridin-2-yl)methyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(N=CC=1)=CC=1C1=CC=CC=C1 QEFPUNCCUIUVKM-UHFFFAOYSA-N 0.000 description 1
- IEQOFOJIXHMSBS-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-[(5-phenylpyridin-2-yl)methyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(N=C1)=CC=C1C1=CC=CC=C1 IEQOFOJIXHMSBS-UHFFFAOYSA-N 0.000 description 1
- KENSGPCARNEVFW-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-[2-oxo-2-[2-(propanoylamino)phenyl]ethyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound CCC(=O)NC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O KENSGPCARNEVFW-UHFFFAOYSA-N 0.000 description 1
- PJHHVDJSPCBOLV-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-[2-oxo-2-[2-oxo-3-(2-trimethylsilylethoxymethyl)-1,3-benzoxazol-7-yl]ethyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC(=O)C=3C=4OC(=O)N(COCC[Si](C)(C)C)C=4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 PJHHVDJSPCBOLV-UHFFFAOYSA-N 0.000 description 1
- NKVHJFSNENYNNZ-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-[[4-oxo-3-(2-trimethylsilylethoxymethyl)phthalazin-1-yl]methyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(=O)N(COCC[Si](C)(C)C)N=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 NKVHJFSNENYNNZ-UHFFFAOYSA-N 0.000 description 1
- TUJAXGOQSUAROV-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)NC(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 TUJAXGOQSUAROV-UHFFFAOYSA-N 0.000 description 1
- KDXZQXUPDBEGDS-FBCYGCLPSA-N tert-butyl n-[1-[3-methyl-7-[(e)-2-methylbut-2-enyl]-2,6-dioxo-1-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC(/C)=C/C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1 KDXZQXUPDBEGDS-FBCYGCLPSA-N 0.000 description 1
- RNMLHWFSQVAKHV-UHFFFAOYSA-N tert-butyl n-[1-[7-(2,3-dimethylbut-2-enyl)-3-methyl-2,6-dioxo-1-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC(C)=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1 RNMLHWFSQVAKHV-UHFFFAOYSA-N 0.000 description 1
- ILMBROFYYKTCIB-UHFFFAOYSA-N tert-butyl n-[1-[7-(2,3-dimethylbut-2-enyl)-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)NC(=O)C=2N(CC(C)=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 ILMBROFYYKTCIB-UHFFFAOYSA-N 0.000 description 1
- COWWHLDTRDXSGM-UHFFFAOYSA-N tert-butyl n-[1-[7-(3-methylbut-2-enyl)-1-[(2-methyl-1-oxoisoquinolin-4-yl)methyl]-2,6-dioxo-3h-purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2NC(=O)N(CC=3C4=CC=CC=C4C(=O)N(C)C=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 COWWHLDTRDXSGM-UHFFFAOYSA-N 0.000 description 1
- PBWLDAVXSGYFFS-UHFFFAOYSA-N tert-butyl n-[1-[7-(3-methylbut-2-enyl)-2,6-dioxo-1-phenacyl-3-(2-trimethylsilylethoxymethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(COCC[Si](C)(C)C)C(=O)N1CC(=O)C1=CC=CC=C1 PBWLDAVXSGYFFS-UHFFFAOYSA-N 0.000 description 1
- KJBYGYWHWGIPPE-UHFFFAOYSA-N tert-butyl n-[1-[7-(3-methylbut-2-enyl)-2,6-dioxo-1-phenacyl-3h-purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2NC(=O)N1CC(=O)C1=CC=CC=C1 KJBYGYWHWGIPPE-UHFFFAOYSA-N 0.000 description 1
- COXNJUOKZZWFPB-UHFFFAOYSA-N tert-butyl n-[1-[7-(3-methylbut-2-enyl)-2,6-dioxo-3-(2-trimethylsilylethoxymethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(COCC[Si](C)(C)C)C(=O)NC(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 COXNJUOKZZWFPB-UHFFFAOYSA-N 0.000 description 1
- BMTYAODFVANLBH-UHFFFAOYSA-N tert-butyl n-[1-[7-(cyclopenten-1-ylmethyl)-1-[2-(2-hydroxyphenyl)-2-oxoethyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1CCCC=1CN1C=2C(=O)N(CC(=O)C=3C(=CC=CC=3)O)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 BMTYAODFVANLBH-UHFFFAOYSA-N 0.000 description 1
- CVYOXNASRFXMTF-UHFFFAOYSA-N tert-butyl n-[1-[7-(cyclopenten-1-ylmethyl)-3-methyl-1-[2-[2-[2-(methylamino)-2-oxoethoxy]phenyl]-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CNC(=O)COC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=2CCCC=2)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O CVYOXNASRFXMTF-UHFFFAOYSA-N 0.000 description 1
- MADGZLZFOMCKJD-UHFFFAOYSA-N tert-butyl n-[1-[7-(cyclopenten-1-ylmethyl)-3-methyl-2,6-dioxo-1-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1CCCC=1CN1C=2C(=O)N(CC(=O)C=3C=CC=CC=3)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 MADGZLZFOMCKJD-UHFFFAOYSA-N 0.000 description 1
- LXRSYECGYLOEDX-UHFFFAOYSA-N tert-butyl n-[1-[7-(furan-2-ylmethyl)-3-methyl-2,6-dioxo-1-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=COC=1CN1C=2C(=O)N(CC(=O)C=3C=CC=CC=3)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 LXRSYECGYLOEDX-UHFFFAOYSA-N 0.000 description 1
- LUZSXJUPOIFKFA-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-bromophenyl)methyl]-1,3-dimethyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(Br)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 LUZSXJUPOIFKFA-UHFFFAOYSA-N 0.000 description 1
- OOPDXQNJSWMYLE-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-chlorophenyl)methyl]-1,3-dimethyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(Cl)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 OOPDXQNJSWMYLE-UHFFFAOYSA-N 0.000 description 1
- QYHDDGPOSXQWDF-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-cyanophenyl)methyl]-1-(2-methoxyethyl)-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)N(CCOC)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 QYHDDGPOSXQWDF-UHFFFAOYSA-N 0.000 description 1
- GJTMDPMSKFSRRV-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-cyanophenyl)methyl]-1-methyl-2,6-dioxo-3-(2-trimethylsilylethoxymethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)N(C)C(=O)N(COCC[Si](C)(C)C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 GJTMDPMSKFSRRV-UHFFFAOYSA-N 0.000 description 1
- SDUBJZNOSOSYCG-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-cyanophenyl)methyl]-1-methyl-2,6-dioxo-3-phenylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound C1=2N=C(N3CC(CCC3)NC(=O)OC(C)(C)C)N(CC=3C(=CC=CC=3)C#N)C=2C(=O)N(C)C(=O)N1C1=CC=CC=C1 SDUBJZNOSOSYCG-UHFFFAOYSA-N 0.000 description 1
- FKFKYSJONJQNNU-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-cyanophenyl)methyl]-1-methyl-2,6-dioxo-3-propan-2-ylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)N(C)C(=O)N(C(C)C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 FKFKYSJONJQNNU-UHFFFAOYSA-N 0.000 description 1
- HPEQQFYYDMGEOD-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-cyanophenyl)methyl]-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C(C)=CC2=CC=CC=C2C=1CN(C(C=1N2CC=3C(=CC=CC=3)C#N)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 HPEQQFYYDMGEOD-UHFFFAOYSA-N 0.000 description 1
- QUNOPHRBRIZZOW-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-cyanophenyl)methyl]-3-methyl-2,6-dioxo-1-(2-phenoxyethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)N(CCOC=3C=CC=CC=3)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 QUNOPHRBRIZZOW-UHFFFAOYSA-N 0.000 description 1
- YCCMMCNGYDYTCM-UHFFFAOYSA-N tert-butyl n-[1-[7-[(2-cyanophenyl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)NC(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 YCCMMCNGYDYTCM-UHFFFAOYSA-N 0.000 description 1
- MLGPARVHAHUUTB-FRKPEAEDSA-N tert-butyl n-[1-[7-[(e)-but-1-enyl]-3-methyl-2,6-dioxo-1-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(/C=C/CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1 MLGPARVHAHUUTB-FRKPEAEDSA-N 0.000 description 1
- PKHQSRYHZPLUKX-VOTSOKGWSA-N tert-butyl n-[1-[7-[(e)-but-2-enyl]-1-[2-(2-hydroxyphenyl)-2-oxoethyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(C/C=C/C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1O PKHQSRYHZPLUKX-VOTSOKGWSA-N 0.000 description 1
- ONPJSYUMODSLHC-BQYQJAHWSA-N tert-butyl n-[1-[7-[(e)-but-2-enyl]-3-methyl-1-[2-[2-[2-(methylamino)-2-oxoethoxy]phenyl]-2-oxoethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CNC(=O)COC1=CC=CC=C1C(=O)CN1C(=O)C(N(C\C=C\C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O ONPJSYUMODSLHC-BQYQJAHWSA-N 0.000 description 1
- UJKIEIPDMMUQFJ-VOTSOKGWSA-N tert-butyl n-[1-[7-[(e)-but-2-enyl]-3-methyl-2,6-dioxo-1-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(C/C=C/C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1 UJKIEIPDMMUQFJ-VOTSOKGWSA-N 0.000 description 1
- BQLYDCHAAWINTJ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-(2-cyanoimino-2-phenylethyl)-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=NC#N)C1=CC=CC=C1 BQLYDCHAAWINTJ-UHFFFAOYSA-N 0.000 description 1
- UVPCRPRNGGKEIL-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-(imidazo[1,2-a]pyridin-2-ylmethyl)-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CN4C=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 UVPCRPRNGGKEIL-UHFFFAOYSA-N 0.000 description 1
- XUMSSVBJYDEDMY-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-(imidazo[1,2-a]pyridin-3-ylmethyl)-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N4C=CC=CC4=NC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 XUMSSVBJYDEDMY-UHFFFAOYSA-N 0.000 description 1
- GTUJIRJFCAIIIS-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-(isoquinolin-1-ylmethyl)-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=CN=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 GTUJIRJFCAIIIS-UHFFFAOYSA-N 0.000 description 1
- BFNNYKRIUWEYBW-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(2-cyano-1-benzofuran-3-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4OC=3C#N)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 BFNNYKRIUWEYBW-UHFFFAOYSA-N 0.000 description 1
- QDAQALIGBUPAKU-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(2-methoxynaphthalen-1-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=C2C=CC=CC2=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 QDAQALIGBUPAKU-UHFFFAOYSA-N 0.000 description 1
- DLAGCJRDJNUMIQ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(2-methyl-1-oxoisoquinolin-4-yl)methyl]-2,6-dioxo-3h-purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2NC(=O)N(CC=3C4=CC=CC=C4C(=O)N(C)C=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 DLAGCJRDJNUMIQ-UHFFFAOYSA-N 0.000 description 1
- PYRDKNIQKOVGAT-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(3,4-dimethyl-5,6,7,8-tetrahydroisoquinolin-1-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C=4CCCCC=4C(C)=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 PYRDKNIQKOVGAT-UHFFFAOYSA-N 0.000 description 1
- GYKIWRBTPQRTIF-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(3-methoxynaphthalen-2-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC2=CC=CC=C2C=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 GYKIWRBTPQRTIF-UHFFFAOYSA-N 0.000 description 1
- LVFJPIWBEHBWDE-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(4-chloro-3-methoxyisoquinolin-1-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=12C=CC=CC2=C(Cl)C(OC)=NC=1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 LVFJPIWBEHBWDE-UHFFFAOYSA-N 0.000 description 1
- MBUSBNKEWWHEPI-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(4-ethoxyquinazolin-2-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C2=CC=CC=C2C(OCC)=NC=1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 MBUSBNKEWWHEPI-UHFFFAOYSA-N 0.000 description 1
- ADOLZOPNKNMYRN-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(4-methoxynaphthalen-1-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C12=CC=CC=C2C(OC)=CC=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 ADOLZOPNKNMYRN-UHFFFAOYSA-N 0.000 description 1
- PKYGRGBHASQKNC-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(5-methoxyisoquinolin-8-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C12=CN=CC=C2C(OC)=CC=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 PKYGRGBHASQKNC-UHFFFAOYSA-N 0.000 description 1
- BOEAQMVGAJBWHB-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(5-methoxyquinolin-8-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C12=NC=CC=C2C(OC)=CC=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 BOEAQMVGAJBWHB-UHFFFAOYSA-N 0.000 description 1
- CTYUBSNJAIPAGC-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[(8-methoxyquinolin-5-yl)methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C12=CC=CN=C2C(OC)=CC=C1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 CTYUBSNJAIPAGC-UHFFFAOYSA-N 0.000 description 1
- DIHJABIPYKBHOZ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[2-(2-methoxyphenyl)-2-oxoethyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC#CC)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O DIHJABIPYKBHOZ-UHFFFAOYSA-N 0.000 description 1
- MQADSMBWBSAEEY-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[2-(3-methoxyphenyl)-2-oxoethyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=CC(C(=O)CN2C(C=3N(CC#CC)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1 MQADSMBWBSAEEY-UHFFFAOYSA-N 0.000 description 1
- DSOCACVNIIQZHK-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[2-[2-(cyanomethoxy)phenyl]-2-oxoethyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1OCC#N DSOCACVNIIQZHK-UHFFFAOYSA-N 0.000 description 1
- IGEXTOXNTIQTSL-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[2-[2-[2-(ethylamino)-2-oxoethoxy]phenyl]-2-oxoethyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CCNC(=O)COC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC#CC)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O IGEXTOXNTIQTSL-UHFFFAOYSA-N 0.000 description 1
- SFALGRMIDSDAKN-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[[1-(2-cyanoethyl)benzimidazol-2-yl]methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N(C4=CC=CC=C4N=3)CCC#N)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 SFALGRMIDSDAKN-UHFFFAOYSA-N 0.000 description 1
- RTAYIAUOXYYZBT-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[[1-(2-cyanopropan-2-yl)isoquinolin-3-yl]methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C(C4=CC=CC=C4C=3)C(C)(C)C#N)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 RTAYIAUOXYYZBT-UHFFFAOYSA-N 0.000 description 1
- XQBXXGRDEXLEIQ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[[2-(2,2-dimethylpropanoyl)-1-benzofuran-3-yl]methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4OC=3C(=O)C(C)(C)C)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 XQBXXGRDEXLEIQ-UHFFFAOYSA-N 0.000 description 1
- WLZOTUYUZMVQBZ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[[4-(dimethylamino)naphthalen-1-yl]methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(N(C)C)=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 WLZOTUYUZMVQBZ-UHFFFAOYSA-N 0.000 description 1
- VYRFENWPHQECHR-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-1-[[4-(dimethylamino)quinazolin-2-yl]methyl]-3-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(N(C)C)N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 VYRFENWPHQECHR-UHFFFAOYSA-N 0.000 description 1
- ATKKEHMAJJJHPQ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-cyclopropyl-1-[(3-methylisoquinolin-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(CC=2C3=CC=CC=C3C=C(C)N=2)C(=O)C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1C1CC1 ATKKEHMAJJJHPQ-UHFFFAOYSA-N 0.000 description 1
- MJVNGTMBPLUGSO-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-cyclopropyl-2,6-dioxo-1-[(4-phenylquinazolin-2-yl)methyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(CC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)C(=O)C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1C1CC1 MJVNGTMBPLUGSO-UHFFFAOYSA-N 0.000 description 1
- XVPQSFBSKCSQJY-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-(1,5-naphthyridin-2-ylmethyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 XVPQSFBSKCSQJY-UHFFFAOYSA-N 0.000 description 1
- JKYKRTFPIVDHRL-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-(1,6-naphthyridin-5-ylmethyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CN=C4C=CN=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 JKYKRTFPIVDHRL-UHFFFAOYSA-N 0.000 description 1
- PUPRDLFDROZSON-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-(1,8-naphthyridin-2-ylmethyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4N=CC=CC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 PUPRDLFDROZSON-UHFFFAOYSA-N 0.000 description 1
- RQFILOOQEZJURH-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-(naphthalen-1-ylmethyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 RQFILOOQEZJURH-UHFFFAOYSA-N 0.000 description 1
- VLBKTTKIPWPSAJ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-(naphthalen-2-ylmethyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C=C4C=CC=CC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 VLBKTTKIPWPSAJ-UHFFFAOYSA-N 0.000 description 1
- ZMSCIIHKSABKIQ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(1-methyl-2-oxoquinolin-4-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4N(C)C(=O)C=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 ZMSCIIHKSABKIQ-UHFFFAOYSA-N 0.000 description 1
- GJIZRDNRGGUOJT-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(1-methyl-2-oxoquinolin-6-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C=C4C=CC(=O)N(C)C4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 GJIZRDNRGGUOJT-UHFFFAOYSA-N 0.000 description 1
- FXYGVSMRJWIPCW-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(1-methylbenzimidazol-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N(C4=CC=CC=C4N=3)C)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 FXYGVSMRJWIPCW-UHFFFAOYSA-N 0.000 description 1
- UBMLACIMYRKLBT-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(1-methylindol-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N(C4=CC=CC=C4C=3)C)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 UBMLACIMYRKLBT-UHFFFAOYSA-N 0.000 description 1
- NCSSPTJFQWDRDC-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(2-methyl-1,3-benzothiazol-6-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C=C4SC(C)=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 NCSSPTJFQWDRDC-UHFFFAOYSA-N 0.000 description 1
- RZNZHYLWLHHWQQ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=CC=3C)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 RZNZHYLWLHHWQQ-UHFFFAOYSA-N 0.000 description 1
- AAMOFATWOXYVIJ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(3-methylisoquinolin-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 AAMOFATWOXYVIJ-UHFFFAOYSA-N 0.000 description 1
- JOMHDULOSAEZBE-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(3-methylquinoxalin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C(=NC4=CC=CC=C4N=3)C)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 JOMHDULOSAEZBE-UHFFFAOYSA-N 0.000 description 1
- QYYOKJZHSMMBRR-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(4-methylisoquinolin-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(C)=CN=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 QYYOKJZHSMMBRR-UHFFFAOYSA-N 0.000 description 1
- KNLNFPZYNXCOQI-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(4-methylphthalazin-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C(C)=NN=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 KNLNFPZYNXCOQI-UHFFFAOYSA-N 0.000 description 1
- IIXXXJZKQFLCDZ-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(4-morpholin-4-ylquinazolin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC#CC)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(N=C1C=CC=CC1=1)=NC=1N1CCOCC1 IIXXXJZKQFLCDZ-UHFFFAOYSA-N 0.000 description 1
- CKBOVGTUPQVUGW-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(5-nitro-1,3-benzoxazol-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3OC4=CC=C(C=C4N=3)[N+]([O-])=O)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 CKBOVGTUPQVUGW-UHFFFAOYSA-N 0.000 description 1
- RECLHFQAJZUBKN-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(5-nitronaphthalen-1-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC(=C4C=CC=3)[N+]([O-])=O)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 RECLHFQAJZUBKN-UHFFFAOYSA-N 0.000 description 1
- LDRFXNKKFSOAGX-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(6-methylimidazo[1,2-a]pyridin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC(C)=CN4C=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 LDRFXNKKFSOAGX-UHFFFAOYSA-N 0.000 description 1
- ITCVLCAEFCLAFH-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[(7-methylimidazo[1,2-a]pyridin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=C(C)C=CN4C=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 ITCVLCAEFCLAFH-UHFFFAOYSA-N 0.000 description 1
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- UACOCVHKKVTLIR-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-1-[[1-[2-(methylamino)-2-oxoethyl]benzimidazol-2-yl]methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C2=CC=CC=C2N(CC(=O)NC)C=1CN(C(C=1N2CC#CC)=O)C(=O)N(C)C=1N=C2N1CCCC(NC(=O)OC(C)(C)C)C1 UACOCVHKKVTLIR-UHFFFAOYSA-N 0.000 description 1
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- XEVVPLVOVUPRPA-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-2,6-dioxo-1-(quinolin-6-ylmethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C=C4C=CC=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 XEVVPLVOVUPRPA-UHFFFAOYSA-N 0.000 description 1
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- CWPSVRFHNHPRGX-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-2,6-dioxo-1-(quinoxalin-2-ylmethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=NC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 CWPSVRFHNHPRGX-UHFFFAOYSA-N 0.000 description 1
- OPSXLEURPQZSTH-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-2,6-dioxo-1-(quinoxalin-6-ylmethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C=C4N=CC=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 OPSXLEURPQZSTH-UHFFFAOYSA-N 0.000 description 1
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- YAGYJECWXXRUFL-UHFFFAOYSA-N tert-butyl n-[1-[7-but-2-ynyl-3-methyl-2,6-dioxo-1-[2-oxo-2-[2-oxo-1,3-bis(2-trimethylsilylethoxymethyl)benzimidazol-4-yl]ethyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC(=O)C=3C=4N(COCC[Si](C)(C)C)C(=O)N(COCC[Si](C)(C)C)C=4C=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 YAGYJECWXXRUFL-UHFFFAOYSA-N 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10238243A DE10238243A1 (de) | 2002-08-21 | 2002-08-21 | 8-[3-Amino-piperidin-1-yl]-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
DE10312353A DE10312353A1 (de) | 2003-03-20 | 2003-03-20 | 8-[3-Amino-piperidin-1-yl]-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
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EA201001167A1 EA201001167A1 (ru) | 2011-02-28 |
EA024251B1 true EA024251B1 (ru) | 2016-08-31 |
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EA201001167A EA024251B1 (ru) | 2002-08-21 | 2003-08-18 | 8-[-3-аминопиперидин-1-ил]ксантины, способ их получения и их применение в качестве лекарственных средств |
EA200702022A EA016166B1 (ru) | 2002-08-21 | 2003-08-18 | 8-[3-аминопиперидин-1-ил]ксантины, способ их получения и их применение в качестве лекарственных средств |
EA200500302A EA010303B1 (ru) | 2002-08-21 | 2003-08-18 | 8-[3-аминопиперидин-1-ил]ксантины, способ их получения и их применение в качестве лекарственных средств |
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EA200702022A EA016166B1 (ru) | 2002-08-21 | 2003-08-18 | 8-[3-аминопиперидин-1-ил]ксантины, способ их получения и их применение в качестве лекарственных средств |
EA200500302A EA010303B1 (ru) | 2002-08-21 | 2003-08-18 | 8-[3-аминопиперидин-1-ил]ксантины, способ их получения и их применение в качестве лекарственных средств |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003101992A1 (en) * | 2002-05-31 | 2003-12-11 | Schering Corporation | Process for preparing xanthine phosphodiesterase v inhibitors and precursors thereof |
GB0215293D0 (en) | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
ATE453644T1 (de) * | 2002-08-21 | 2010-01-15 | Boehringer Ingelheim Pharma | 8-[3-amino-piperidin-1-yl] -xanthine, deren herstellung und deren verwendung als arzneimittel |
US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
US7569574B2 (en) | 2002-08-22 | 2009-08-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Purine derivatives, the preparation thereof and their use as pharmaceutical compositions |
US7495005B2 (en) | 2002-08-22 | 2009-02-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, their preparation and their use in pharmaceutical compositions |
US7482337B2 (en) * | 2002-11-08 | 2009-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
DE10251927A1 (de) * | 2002-11-08 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
DE10254304A1 (de) | 2002-11-21 | 2004-06-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
US7550590B2 (en) | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
EP1620091B1 (en) | 2003-05-05 | 2010-03-31 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
WO2004103993A1 (en) | 2003-05-14 | 2004-12-02 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
US7566707B2 (en) | 2003-06-18 | 2009-07-28 | Boehringer Ingelheim International Gmbh | Imidazopyridazinone and imidazopyridone derivatives, the preparation thereof and their use as pharmaceutical compositions |
US20050070531A1 (en) | 2003-08-13 | 2005-03-31 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
DE10355304A1 (de) | 2003-11-27 | 2005-06-23 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 8-(Piperazin-1-yl)-und 8-([1,4]Diazepan-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
NZ595000A (en) | 2003-12-22 | 2013-03-28 | Gilead Sciences Inc | Imidazo[4,5-c]pyridine derivative for treating viral infections |
DE10360835A1 (de) * | 2003-12-23 | 2005-07-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclische Imidazolverbindungen, deren Herstellung und deren Verwendung als Arzneimittel |
AU2012202850B2 (en) * | 2004-02-18 | 2015-08-20 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthine, the production thereof and the use in the form of a DPP inhibitor |
US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
EP2119717B1 (de) * | 2004-02-18 | 2018-01-17 | Boehringer Ingelheim International GmbH | 8-[3-amino-piperidin-1-yl]-Xanthine, deren Herstellung und deren Verwendung als DPP IV Hemmer |
DE102004009039A1 (de) | 2004-02-23 | 2005-09-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-[3-Amino-piperidin-1-yl]-xanthine, deren Herstellung und Verwendung als Arzneimittel |
US7393847B2 (en) | 2004-03-13 | 2008-07-01 | Boehringer Ingleheim International Gmbh | Imidazopyridazinediones, their preparation and their use as pharmaceutical compositions |
CN102140090A (zh) | 2004-03-15 | 2011-08-03 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
US7439370B2 (en) | 2004-05-10 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Imidazole derivatives, their preparation and their use as intermediates for the preparation of pharmaceutical compositions and pesticides |
DE102004030502A1 (de) | 2004-06-24 | 2006-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazole und Triazole, deren Herstellung und Verwendung als Arzneimittel |
CN101027303A (zh) | 2004-07-27 | 2007-08-29 | 吉里德科学公司 | 咪唑并[4,5-d]嘧啶类、其应用和制备方法 |
DE102004043944A1 (de) | 2004-09-11 | 2006-03-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 8-(3-Amino-piperidin-1-yl)-7-(but-2-inyl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
DE102004044221A1 (de) | 2004-09-14 | 2006-03-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 3-Methyl-7-butinyl-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
DE102004054054A1 (de) * | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
AU2012205240B2 (en) * | 2004-11-05 | 2015-03-26 | Boehringer Ingelheim International Gmbh | Method for producing chiral 8-(3-amino-piperidin-1-yl)-xanthines |
PT1841765E (pt) | 2004-12-21 | 2009-05-14 | Gilead Sciences Inc | Anticorpos para mcp-1 humano |
DOP2006000008A (es) | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
PL1931350T5 (pl) † | 2005-09-14 | 2021-11-15 | Takeda Pharmaceutical Company Limited | Podanie inhibitorów dipeptydylo-peptydazy |
JP5027137B2 (ja) | 2005-09-14 | 2012-09-19 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼ阻害剤の投与 |
KR101368988B1 (ko) | 2005-09-16 | 2014-02-28 | 다케다 야쿠힌 고교 가부시키가이샤 | 디펩티딜 펩티다제 억제제 |
BRPI0620464A2 (pt) * | 2005-12-23 | 2011-11-16 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto, e, método para o tratamento de uma doença |
GB0526291D0 (en) | 2005-12-23 | 2006-02-01 | Prosidion Ltd | Therapeutic method |
TW200803855A (en) * | 2006-02-24 | 2008-01-16 | Kalypsys Inc | Quinolones useful as inducible nitric oxide synthase inhibitors |
WO2007112347A1 (en) | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
PE20071221A1 (es) | 2006-04-11 | 2007-12-14 | Arena Pharm Inc | Agonistas del receptor gpr119 en metodos para aumentar la masa osea y para tratar la osteoporosis y otras afecciones caracterizadas por masa osea baja, y la terapia combinada relacionada a estos agonistas |
EP1852108A1 (en) * | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
BRPI0711558A2 (pt) * | 2006-05-04 | 2011-11-08 | Boeringer Ingelheim Internat Gmbh | polimorfos |
PE20110235A1 (es) * | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
HRP20090078A2 (en) | 2006-07-07 | 2009-06-30 | Gilead Sciences | Novel pyridazine compound and use thereof |
EP2057160A1 (en) | 2006-08-08 | 2009-05-13 | Boehringer Ingelheim International GmbH | Pyrrolo [3, 2 -d]pyrimidines as dpp-iv inhibitors for the treatment of diabetes mellitus |
US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
WO2008055945A1 (en) | 2006-11-09 | 2008-05-15 | Probiodrug Ag | 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one derivatives as inhibitors of glutaminyl cyclase for the treatment of ulcer, cancer and other diseases |
TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
WO2008065141A1 (en) | 2006-11-30 | 2008-06-05 | Probiodrug Ag | Novel inhibitors of glutaminyl cyclase |
US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
US9656991B2 (en) | 2007-04-18 | 2017-05-23 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
PE20090938A1 (es) * | 2007-08-16 | 2009-08-08 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un derivado de benceno sustituido con glucopiranosilo |
UY31291A1 (es) * | 2007-08-16 | 2009-03-31 | Composicion farmacéutica que comprende un derivado de pirazol-0-glucosido | |
EP3542801A1 (en) * | 2007-08-17 | 2019-09-25 | Boehringer Ingelheim International GmbH | Purin derivatives for use in the treatment of fap-related diseases |
PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
EP2146210A1 (en) | 2008-04-07 | 2010-01-20 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditions modulated by PYY |
PE20100156A1 (es) * | 2008-06-03 | 2010-02-23 | Boehringer Ingelheim Int | Tratamiento de nafld |
KR20190016601A (ko) | 2008-08-06 | 2019-02-18 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
AU2009281122C1 (en) * | 2008-08-15 | 2016-04-21 | Boehringer Ingelheim International Gmbh | Purin derivatives for use in the treatment of fab-related diseases |
WO2010029089A2 (en) * | 2008-09-10 | 2010-03-18 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
UY32177A (es) * | 2008-10-16 | 2010-05-31 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con control glucémico insuficiente a pesar de la terapia con fármaco, oral o no, antidiabético |
AU2009331471B2 (en) * | 2008-12-23 | 2015-09-03 | Boehringer Ingelheim International Gmbh | Salt forms of organic compound |
TW201036975A (en) * | 2009-01-07 | 2010-10-16 | Boehringer Ingelheim Int | Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy |
AR075204A1 (es) | 2009-01-29 | 2011-03-16 | Boehringer Ingelheim Int | Inhibidores de dpp-4 y composiciones farmaceuticas que los comprenden, utiles para tratar enfermedades metabolicas en pacientes pediatricos, particularmente diabetes mellitus tipo 2 |
SG173619A1 (en) | 2009-02-13 | 2011-09-29 | Boehringer Ingelheim Int | Pharmaceutical composition comprising a sglt2 inhibitor, a dpp-iv inhibitor and optionally a further antidiabetic agent and uses thereof |
UY32427A (es) * | 2009-02-13 | 2010-09-30 | Boheringer Ingelheim Internat Gmbh | Composicion farmaceutica, forma farmaceutica, procedimiento para su preparacion, metodos de tratamiento y usos de la misma |
AU2010212823B2 (en) | 2009-02-13 | 2016-01-28 | Boehringer Ingelheim International Gmbh | Antidiabetic medications comprising a DPP-4 inhibitor (linagliptin) optionally in combination with other antidiabetics |
AR077642A1 (es) | 2009-07-09 | 2011-09-14 | Arena Pharm Inc | Moduladores del metabolismo y el tratamiento de trastornos relacionados con el mismo |
EA022007B1 (ru) | 2009-09-11 | 2015-10-30 | Пробиодруг Аг | Гетероциклические производные в качестве ингибиторов глутаминилциклазы |
CA2775961C (en) | 2009-09-30 | 2017-11-07 | Boehringer Ingelheim International Gmbh | Method for the preparation of a crystalline form of 1-chloro-4-(beta-d-glucopyranos-1-yl)-2-(4-((s)-tetrahydrofuran-3-yloxy)benzyl)benzene |
HRP20150945T1 (hr) | 2009-09-30 | 2015-10-09 | Boehringer Ingelheim International Gmbh | Postupci za proizvodnju derivata benzil-benzena supstituiranog glukopiranozilom |
EP4209210A1 (en) | 2009-10-02 | 2023-07-12 | Boehringer Ingelheim International GmbH | Pharmaceutical compositions comprising bi-1356 and metformin |
US10610489B2 (en) | 2009-10-02 | 2020-04-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, pharmaceutical dosage form, process for their preparation, methods for treating and uses thereof |
AU2010323068B2 (en) | 2009-11-27 | 2015-09-03 | Boehringer Ingelheim International Gmbh | Treatment of genotyped diabetic patients with DPP-IV inhibitors such as linagliptin |
EP2542549B1 (en) | 2010-03-03 | 2016-05-11 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
ES2481823T3 (es) | 2010-03-10 | 2014-07-31 | Probiodrug Ag | Inhibidores heterocíclicos de glutaminil ciclasa (QC, EC 2.3.2.5) |
EP2547339A1 (en) | 2010-03-18 | 2013-01-23 | Boehringer Ingelheim International GmbH | Combination of a gpr119 agonist and the dpp-iv inhibitor linagliptin for use in the treatment of diabetes and related conditions |
MX2012011631A (es) | 2010-04-06 | 2013-01-18 | Arena Pharm Inc | Moduladores del receptor gpr119 y el tratamiento de trastornos relacionados con el mismo. |
EP2560953B1 (en) | 2010-04-21 | 2016-01-06 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
JP6034781B2 (ja) | 2010-05-05 | 2016-11-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 併用療法 |
CA2795105A1 (en) | 2010-05-05 | 2011-11-10 | Peter Schneider | Pharmaceutical formulations comprising pioglitazone and linagliptin |
PH12012502524A1 (en) * | 2010-06-24 | 2014-02-10 | Boehringer Ingelheim Int | Diabetes therapy |
JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ, インコーポレイテッド | Gpr119レセプターのモジュレーターおよびそれに関連する障害の処置 |
US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
ES2777890T3 (es) * | 2010-11-15 | 2020-08-06 | Boehringer Ingelheim Int | Terapia antidiabética vasoprotectora y cardioprotectora |
US20130035281A1 (en) | 2011-02-09 | 2013-02-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
JP6050264B2 (ja) | 2011-03-16 | 2016-12-21 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 |
WO2012135570A1 (en) | 2011-04-01 | 2012-10-04 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
US20140066369A1 (en) | 2011-04-19 | 2014-03-06 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
US20140038889A1 (en) | 2011-04-22 | 2014-02-06 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
US20140051714A1 (en) | 2011-04-22 | 2014-02-20 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
EP2707368B1 (en) * | 2011-05-10 | 2016-02-03 | Sandoz AG | Polymorph of linagliptin benzoate |
WO2012170702A1 (en) | 2011-06-08 | 2012-12-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
HUE061596T2 (hu) | 2011-07-15 | 2023-07-28 | Boehringer Ingelheim Int | Szubsztituált dimer kinazolin származék, annak elõállítása és alkalmazása az I. és II. típusú cukorbetegség kezelésére szolgáló gyógyszerkészítményekben |
WO2013055910A1 (en) | 2011-10-12 | 2013-04-18 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2013074817A1 (en) | 2011-11-16 | 2013-05-23 | Assia Chemical Industries Ltd. | Solid state forms of linagliptin |
US20130172244A1 (en) | 2011-12-29 | 2013-07-04 | Thomas Klein | Subcutaneous therapeutic use of dpp-4 inhibitor |
CN103254192B (zh) * | 2012-02-15 | 2015-12-02 | 上海医药工业研究院 | 黄嘌呤类化合物、其盐、中间体、制备方法及应用 |
CN103254193B (zh) * | 2012-02-15 | 2015-04-22 | 上海医药工业研究院 | 黄嘌呤类化合物中间体及其制备方法 |
US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
US9879011B2 (en) | 2012-03-12 | 2018-01-30 | Cadila Healthcare Limited | Amorphous form of linagliptin and process for preparation thereof |
US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
CN103373999B (zh) * | 2012-04-28 | 2016-01-13 | 上海医药工业研究院 | 嘌呤类化合物、中间体、制备方法及其应用 |
JP6218811B2 (ja) | 2012-05-14 | 2017-10-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Sirs及び/又は敗血症の治療に用いるdpp−4阻害薬としてのキサンチン誘導体 |
WO2013171167A1 (en) * | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
WO2013174768A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of autoimmune diabetes, particularly lada |
EP2854824A1 (en) | 2012-05-25 | 2015-04-08 | Boehringer Ingelheim International GmbH | Use of keratinocytes as a biologically active substance in the treatment of wounds, such as diabetic wounds, optionally in combination with a dpp-4 inhibitor |
CN103509023B (zh) * | 2012-06-20 | 2014-08-27 | 成都苑东药业有限公司 | 黄嘌呤衍生物 |
CN103509022B (zh) * | 2012-06-20 | 2015-04-01 | 成都苑东药业有限公司 | 黄嘌呤衍生物 |
CA2879003C (en) | 2012-08-13 | 2020-09-22 | Sandoz Ag | Stable pharmaceutical composition containing 8-[(3r)-3-amino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1h-purine-2,6-dione or a pharmaceutically acceptable salt thereof |
WO2014045266A1 (en) | 2012-09-24 | 2014-03-27 | Ulf Eriksson | Treatment of type 2 diabetes and related conditions |
CN103709163B (zh) * | 2012-09-29 | 2016-12-21 | 齐鲁制药有限公司 | 黄嘌呤衍生物、其制备方法及用途 |
UA116217C2 (uk) | 2012-10-09 | 2018-02-26 | Санофі | Пептидна сполука як подвійний агоніст рецепторів glp1-1 та глюкагону |
CN103319483B (zh) | 2012-10-19 | 2016-08-03 | 药源药物化学(上海)有限公司 | 一种利拉列汀重要中间体的制备方法 |
WO2014074668A1 (en) | 2012-11-08 | 2014-05-15 | Arena Pharmaceuticals, Inc. | Modulators of gpr119 and the treatment of disorders related thereto |
WO2014097314A1 (en) * | 2012-12-17 | 2014-06-26 | Mylan Laboratories Ltd | An improved process for the preparation of linagliptin |
JP2016503771A (ja) | 2012-12-21 | 2016-02-08 | サノフイ | エキセンジン−4誘導体 |
CN103936739B (zh) * | 2013-01-23 | 2016-08-31 | 成都苑东生物制药股份有限公司 | 黄嘌呤衍生物 |
CN103936740B (zh) * | 2013-01-23 | 2016-06-29 | 成都苑东生物制药股份有限公司 | 黄嘌呤衍生物 |
CN103936738B (zh) * | 2013-01-23 | 2016-11-23 | 成都苑东生物制药股份有限公司 | 黄嘌呤衍生物 |
CN103936737B (zh) * | 2013-01-23 | 2016-09-14 | 成都苑东生物制药股份有限公司 | 黄嘌呤衍生物 |
HK1218762A1 (zh) | 2013-03-15 | 2017-03-10 | Takeda Pharmaceutical Company Limited | 抗血浆激肽释放酶抗体 |
CN105188706A (zh) | 2013-03-15 | 2015-12-23 | 勃林格殷格翰国际有限公司 | 利格列汀在心脏和肾脏保护性抗糖尿病治疗中的用途 |
US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
PT2981271T (pt) | 2013-04-05 | 2019-02-19 | Boehringer Ingelheim Int | Utilizações terapêuticas de empagliflozina |
HK1213818A1 (zh) | 2013-04-05 | 2016-07-15 | 勃林格殷格翰国际有限公司 | 依帕列净的治疗用途 |
RS63042B1 (sr) | 2013-04-18 | 2022-04-29 | Boehringer Ingelheim Int | Farmaceutske kompozicije, metode lečenja i njihova upotreba |
CA2914791A1 (en) * | 2013-06-14 | 2014-12-18 | Boehringer Ingelheim International Gmbh | Dpp-4 inhibitors for treating diabetes and its complications |
CN104292228B (zh) * | 2013-07-16 | 2016-03-30 | 成都苑东生物制药股份有限公司 | 一种黄嘌呤化合物的多晶型及其制备方法、用途 |
WO2015011609A1 (en) | 2013-07-23 | 2015-01-29 | Ranbaxy Laboratories Limited | Process for the preparation of linagliptin and an intermediate thereof |
CN104418857A (zh) * | 2013-08-22 | 2015-03-18 | 北京蓝丹医药科技有限公司 | 无定型利格列汀及其制备方法 |
TW201609796A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 非醯化之艾塞那肽-4(exendin-4)胜肽類似物 |
EP3080149A1 (en) | 2013-12-13 | 2016-10-19 | Sanofi | Dual glp-1/glucagon receptor agonists |
TW201609795A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 作為雙重glp-1/gip受體促效劑的艾塞那肽-4(exendin-4)胜肽類似物 |
EP3080154B1 (en) | 2013-12-13 | 2018-02-07 | Sanofi | Dual glp-1/gip receptor agonists |
CN104725379A (zh) * | 2013-12-24 | 2015-06-24 | 杭州民生药物研究院有限公司 | 嘌呤酮衍生物及其组合物的制备方法与用途 |
US9526728B2 (en) | 2014-02-28 | 2016-12-27 | Boehringer Ingelheim International Gmbh | Medical use of a DPP-4 inhibitor |
TW201625669A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自艾塞那肽-4(Exendin-4)之肽類雙重GLP-1/升糖素受體促效劑 |
TW201625670A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自exendin-4之雙重glp-1/升糖素受體促效劑 |
TW201625668A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 作為胜肽性雙重glp-1/昇糖素受體激動劑之艾塞那肽-4衍生物 |
US9932381B2 (en) | 2014-06-18 | 2018-04-03 | Sanofi | Exendin-4 derivatives as selective glucagon receptor agonists |
CN104557935B (zh) * | 2015-01-27 | 2016-08-17 | 江苏嘉逸医药有限公司 | 制备(r)-8-(3-氨基哌啶-1-基)-黄嘌呤的提纯方法 |
JP2018507914A (ja) | 2015-03-09 | 2018-03-22 | インテクリン・セラピューティクス・インコーポレイテッド | 非アルコール性脂肪肝疾患および/またはリポジストロフィーの処置のための方法 |
AR105319A1 (es) | 2015-06-05 | 2017-09-27 | Sanofi Sa | Profármacos que comprenden un conjugado agonista dual de glp-1 / glucagón conector ácido hialurónico |
JP6901976B2 (ja) * | 2015-06-25 | 2021-07-14 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | キサンチンをベースとする化合物の調製方法 |
TW201706291A (zh) | 2015-07-10 | 2017-02-16 | 賽諾菲公司 | 作為選擇性肽雙重glp-1/升糖素受體促效劑之新毒蜥外泌肽(exendin-4)衍生物 |
WO2017060398A1 (en) | 2015-10-09 | 2017-04-13 | Hexal Ag | Pharmaceutical composition containing 8-[(3r)-3-amino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[4-methyl-2-quinazolinyl)methyl]-1h-purine-2,6-dione or a pharmaceutically acceptable salt thereof |
EP3156048A1 (en) | 2015-10-13 | 2017-04-19 | Galenicum Health S.L. | Stable pharmaceutical composition of linagliptin in the form of immediate release tablets |
CN105566271B (zh) * | 2015-12-03 | 2019-09-13 | 福建医科大学 | 双黄酮化合物及其制备治疗癌症的药物的用途 |
US10155000B2 (en) | 2016-06-10 | 2018-12-18 | Boehringer Ingelheim International Gmbh | Medical use of pharmaceutical combination or composition |
US20180125813A1 (en) | 2016-11-10 | 2018-05-10 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
US11285180B2 (en) | 2016-12-06 | 2022-03-29 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods of enhancing the potency of incretin-based drugs in subjects in need thereof |
CN110996951A (zh) | 2017-04-03 | 2020-04-10 | 科赫罗斯生物科学股份有限公司 | 治疗进行性核上性麻痹的PPARγ激动剂 |
KR102469957B1 (ko) | 2017-06-30 | 2022-11-24 | 한미약품 주식회사 | 리나글립틴, 메트포르민 및 항산화제를 포함하는, 안정성이 개선된 약제학적 조성물 |
CN107325114B (zh) * | 2017-07-04 | 2019-06-11 | 吉林省爱诺德生物工程有限公司 | 一种头孢洛林酯中间体的制备方法 |
ES2812698T3 (es) | 2017-09-29 | 2021-03-18 | Probiodrug Ag | Inhibidores de glutaminil ciclasa |
KR102500835B1 (ko) | 2017-10-24 | 2023-02-17 | 한미약품 주식회사 | 리나글립틴 및 메트포르민을 포함하는 복합제제 및 그의 제조방법 |
CN108299436B (zh) * | 2018-02-09 | 2020-01-17 | 上海慈瑞医药科技股份有限公司 | 黄嘌呤类化合物及其药物组合物和应用 |
KR102208009B1 (ko) * | 2018-04-26 | 2021-01-28 | 주식회사 경보제약 | 신규한 리나글립틴 염 화합물, 이의 제조 방법 및 신규한 리나글립틴 염 화합물로부터 제조된 리나글립틴 |
KR102647472B1 (ko) | 2018-07-31 | 2024-03-14 | 한미약품 주식회사 | 디펩티딜 펩티다아제-4 억제제 및 메트포르민을 포함하는 경구용 고형 복합제제 및 이의 제조방법 |
HU231374B1 (hu) | 2018-08-06 | 2023-04-28 | Richter Gedeon Nyrt. | Eljárás BOC-Linagliptin előállítására |
CN113543852A (zh) | 2019-03-06 | 2021-10-22 | 第一三共株式会社 | 吡咯并吡唑衍生物 |
CN110305131B (zh) * | 2019-07-03 | 2021-12-31 | 山东百诺医药股份有限公司 | 利格列汀新晶型及其制备方法 |
EP3811930A1 (en) | 2019-10-24 | 2021-04-28 | Authenda Pharmaceuticals AG | Oral gliptin compositions and method for preparation thereof |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0149578A2 (fr) * | 1984-01-17 | 1985-07-24 | Adir | Nouveaux dérivés de la xanthine, leur procédé de préparation et les compositions pharmaceutiques les renfermant |
WO1991007945A1 (fr) * | 1989-11-28 | 1991-06-13 | Lvmh Recherche | Utilisation de xanthines, eventuellement incorporees dans des liposomes, pour favoriser la pigmentation de la peau ou des cheveux |
WO2002002560A2 (en) * | 2000-07-04 | 2002-01-10 | Novo Nordisk A/S | Purine-2,6-diones which are inhibitors of the enzyme dipeptidyl peptidase iv (dpp-iv) |
WO2002068420A1 (de) * | 2001-02-24 | 2002-09-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthinderivate, deren herstellung und deren verwendung als arzneimittel |
WO2003004496A1 (en) * | 2001-07-03 | 2003-01-16 | Novo Nordisk A/S | Dpp-iv-inhibiting purine derivatives for the treatment of diabetes |
WO2003024965A2 (en) * | 2001-09-19 | 2003-03-27 | Novo Nordisk A/S | Heterocyclic compounds that are inhibitors of the enzyme dpp-iv |
WO2003057200A2 (en) * | 2002-01-11 | 2003-07-17 | Novo Nordisk A/S | Compositions comprising inhibitors of dpp-iv and nep enzymes for the treatment of diabetes |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4061753A (en) * | 1976-02-06 | 1977-12-06 | Interx Research Corporation | Treating psoriasis with transient pro-drug forms of xanthine derivatives |
US4968672A (en) * | 1987-01-02 | 1990-11-06 | The United States Of America As Represented By The Department Of Health And Human Services | Adenosine receptor prodrugs |
US5965555A (en) * | 1996-06-07 | 1999-10-12 | Hoechst Aktiengesellschaft | Xanthine compounds having terminally animated alkynol side chains |
DE69830577T2 (de) | 1997-04-15 | 2006-05-04 | Genentech, Inc., South San Francisco | Halo-alkoxycarbonylverbindungen |
DE19828114A1 (de) * | 1998-06-24 | 2000-01-27 | Probiodrug Ges Fuer Arzneim | Produgs instabiler Inhibitoren der Dipeptidyl Peptidase IV |
EP1741445B1 (en) * | 2000-01-21 | 2013-08-14 | Novartis AG | Combinations comprising dipeptidylpeptidase-IV inhibitors and antidiabetic agents |
GB0008694D0 (en) * | 2000-04-07 | 2000-05-31 | Novartis Ag | Organic compounds |
GB0014969D0 (en) * | 2000-06-19 | 2000-08-09 | Smithkline Beecham Plc | Novel method of treatment |
ATE453644T1 (de) * | 2002-08-21 | 2010-01-15 | Boehringer Ingelheim Pharma | 8-[3-amino-piperidin-1-yl] -xanthine, deren herstellung und deren verwendung als arzneimittel |
DE10251927A1 (de) * | 2002-11-08 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0149578A2 (fr) * | 1984-01-17 | 1985-07-24 | Adir | Nouveaux dérivés de la xanthine, leur procédé de préparation et les compositions pharmaceutiques les renfermant |
WO1991007945A1 (fr) * | 1989-11-28 | 1991-06-13 | Lvmh Recherche | Utilisation de xanthines, eventuellement incorporees dans des liposomes, pour favoriser la pigmentation de la peau ou des cheveux |
WO2002002560A2 (en) * | 2000-07-04 | 2002-01-10 | Novo Nordisk A/S | Purine-2,6-diones which are inhibitors of the enzyme dipeptidyl peptidase iv (dpp-iv) |
WO2002068420A1 (de) * | 2001-02-24 | 2002-09-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthinderivate, deren herstellung und deren verwendung als arzneimittel |
WO2003004496A1 (en) * | 2001-07-03 | 2003-01-16 | Novo Nordisk A/S | Dpp-iv-inhibiting purine derivatives for the treatment of diabetes |
WO2003024965A2 (en) * | 2001-09-19 | 2003-03-27 | Novo Nordisk A/S | Heterocyclic compounds that are inhibitors of the enzyme dpp-iv |
WO2003057200A2 (en) * | 2002-01-11 | 2003-07-17 | Novo Nordisk A/S | Compositions comprising inhibitors of dpp-iv and nep enzymes for the treatment of diabetes |
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