DE60211530T2 - Pyrrolopyrimidine als mittel zur inhibierung von cysteinproteasen - Google Patents

Info

Publication number

DE60211530T2

DE60211530T2 DE60211530T DE60211530T DE60211530T2 DE 60211530 T2 DE60211530 T2 DE 60211530T2 DE 60211530 T DE60211530 T DE 60211530T DE 60211530 T DE60211530 T DE 60211530T DE 60211530 T2 DE60211530 T2 DE 60211530T2

Authority

DE

Germany

Prior art keywords

mmol

lower alkyl

pyrrolo

acoet

heterocyclyl

Prior art date

2001-08-30

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 230000002401 inhibitory effect Effects 0.000 title description 3
• 102000035195 Peptidases Human genes 0.000 title description 2
• 108091005804 Peptidases Proteins 0.000 title description 2
• 239000004365 Protease Substances 0.000 title 1
• 239000010143 cystone Substances 0.000 title 1
• 150000004944 pyrrolopyrimidines Chemical class 0.000 title 1
• -1 R 4 is H Chemical group 0.000 claims description 275
• 150000001875 compounds Chemical class 0.000 claims description 140
• 125000000217 alkyl group Chemical group 0.000 claims description 88
• 238000000034 method Methods 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 24
• 238000002360 preparation method Methods 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 102000004171 Cathepsin K Human genes 0.000 claims description 19
• 108090000625 Cathepsin K Proteins 0.000 claims description 19
• 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 150000002148 esters Chemical class 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• CYJAWBVQRMVFEO-UHFFFAOYSA-N piperazine-2,6-dione Chemical compound O=C1CNCC(=O)N1 CYJAWBVQRMVFEO-UHFFFAOYSA-N 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 239000002243 precursor Substances 0.000 claims description 9
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
• 125000003435 aroyl group Chemical group 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 8
• 229940091173 hydantoin Drugs 0.000 claims description 8
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 238000011321 prophylaxis Methods 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 229910052721 tungsten Inorganic materials 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000003368 amide group Chemical group 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 230000008878 coupling Effects 0.000 claims description 4
• 238000005859 coupling reaction Methods 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 238000007363 ring formation reaction Methods 0.000 claims description 4
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 238000010168 coupling process Methods 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
• 239000004480 active ingredient Substances 0.000 claims description 2
• 125000005251 aryl acyl group Chemical group 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 239000003814 drug Substances 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• 125000003003 spiro group Chemical group 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• 125000005257 alkyl acyl group Chemical group 0.000 claims 1
• 229940079593 drug Drugs 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 348
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 299
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 199
• 239000000203 mixture Substances 0.000 description 158
• 239000000243 solution Substances 0.000 description 137
• 239000011541 reaction mixture Substances 0.000 description 136
• 239000012267 brine Substances 0.000 description 113
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 113
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 102
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 78
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
• 239000000284 extract Substances 0.000 description 69
• 238000010898 silica gel chromatography Methods 0.000 description 66
• 239000012074 organic phase Substances 0.000 description 63
• 239000000047 product Substances 0.000 description 62
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
• 239000007858 starting material Substances 0.000 description 59
• 230000002829 reductive effect Effects 0.000 description 56
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 54
• 239000000741 silica gel Substances 0.000 description 52
• 229910002027 silica gel Inorganic materials 0.000 description 52
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 51
• 235000019341 magnesium sulphate Nutrition 0.000 description 51
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
• 239000012043 crude product Substances 0.000 description 45
• 239000002904 solvent Substances 0.000 description 39
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
• 235000019439 ethyl acetate Nutrition 0.000 description 34
• 229910052938 sodium sulfate Inorganic materials 0.000 description 34
• 235000011152 sodium sulphate Nutrition 0.000 description 34
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 33
• SVNIABUZGXNWNA-UHFFFAOYSA-N 6-(bromomethyl)-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C2N(CC(C)(C)C)C(CBr)=CC2=C1 SVNIABUZGXNWNA-UHFFFAOYSA-N 0.000 description 30
• 238000003756 stirring Methods 0.000 description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 239000012299 nitrogen atmosphere Substances 0.000 description 26
• 229910000027 potassium carbonate Inorganic materials 0.000 description 25
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• 238000004440 column chromatography Methods 0.000 description 21
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 238000004587 chromatography analysis Methods 0.000 description 17
• 238000000746 purification Methods 0.000 description 17
• 239000003480 eluent Substances 0.000 description 16
• 239000007787 solid Substances 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• 238000001704 evaporation Methods 0.000 description 14
• 230000008020 evaporation Effects 0.000 description 14
• 238000001816 cooling Methods 0.000 description 13
• 239000005457 ice water Substances 0.000 description 13
• 0 CC(C1)C(*(C)=CC(*2CC(C)(C)C)=CC(C=*C3C)=C2*=C3C#*)=CC=C1N Chemical compound CC(C1)C(*(C)=CC(*2CC(C)(C)C)=CC(C=*C3C)=C2*=C3C#*)=CC=C1N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 12
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
• 238000011282 treatment Methods 0.000 description 11
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• KZXZPTCXNTWWCS-UHFFFAOYSA-N 5-bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrile Chemical compound CC(C)(C)CNC1=NC(C#N)=NC=C1Br KZXZPTCXNTWWCS-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 238000004128 high performance liquid chromatography Methods 0.000 description 8
• ONNNJLDEPAZHLQ-UHFFFAOYSA-N 6-[(4-aminophenyl)methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CC1=CC=C(N)C=C1 ONNNJLDEPAZHLQ-UHFFFAOYSA-N 0.000 description 7
• 241000124008 Mammalia Species 0.000 description 7
• 208000001132 Osteoporosis Diseases 0.000 description 7
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• 206010028980 Neoplasm Diseases 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 230000005764 inhibitory process Effects 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• 125000004076 pyridyl group Chemical group 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• XQWHIIQIVZJEMR-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-(piperazin-1-ylmethyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCNCC1 XQWHIIQIVZJEMR-UHFFFAOYSA-N 0.000 description 5
• HCJRBZZBADWUJG-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(1-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CN1C(=O)N(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)C(=O)C11CCNCC1 HCJRBZZBADWUJG-UHFFFAOYSA-N 0.000 description 5
• SYHBEDCSCPDPHK-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(4-oxopiperidin-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCC(=O)CC1 SYHBEDCSCPDPHK-UHFFFAOYSA-N 0.000 description 5
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 238000000605 extraction Methods 0.000 description 5
• 150000002466 imines Chemical class 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
• 201000008482 osteoarthritis Diseases 0.000 description 5
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 238000004007 reversed phase HPLC Methods 0.000 description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 description 5
• UDOCGQWNCVEJNF-UHFFFAOYSA-N tert-butyl 4-(2-fluoro-4-hydroxyphenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(O)C=C1F UDOCGQWNCVEJNF-UHFFFAOYSA-N 0.000 description 5
• DPWSMMSNJFCJNW-LLVKDONJSA-N (5r)-1-[(4-chlorophenyl)methyl]-5-propan-2-ylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)[C@@H](C(C)C)N1CC1=CC=C(Cl)C=C1 DPWSMMSNJFCJNW-LLVKDONJSA-N 0.000 description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
• XQRLXUYZKZXSBN-UHFFFAOYSA-N 1-benzyl-4-hydroxypiperidine-4-carbonitrile Chemical compound C1CC(O)(C#N)CCN1CC1=CC=CC=C1 XQRLXUYZKZXSBN-UHFFFAOYSA-N 0.000 description 4
• CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 4
• FUPPPVQJOVHZSX-UHFFFAOYSA-N 1-oxa-8-thia-3-azaspiro[4.5]decane-2,4-dione Chemical compound O1C(=O)NC(=O)C11CCSCC1 FUPPPVQJOVHZSX-UHFFFAOYSA-N 0.000 description 4
• VURIYIYAKMLWMZ-UHFFFAOYSA-N 4-benzylpiperazine-2,6-dione Chemical compound C1C(=O)NC(=O)CN1CC1=CC=CC=C1 VURIYIYAKMLWMZ-UHFFFAOYSA-N 0.000 description 4
• DRETZBXCDQMKEU-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(2,6-dioxopiperazin-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C(=O)CNCC1=O DRETZBXCDQMKEU-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• 229910004298 SiO 2 Inorganic materials 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 125000001931 aliphatic group Chemical group 0.000 description 4
• 125000003282 alkyl amino group Chemical group 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• 239000012298 atmosphere Substances 0.000 description 4
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
• 229910000024 caesium carbonate Inorganic materials 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
• 238000000338 in vitro Methods 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• WFNRSIKLRUTKMJ-UHFFFAOYSA-N n-[4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]phenyl]methanesulfonamide Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CC1=CC=C(NS(C)(=O)=O)C=C1 WFNRSIKLRUTKMJ-UHFFFAOYSA-N 0.000 description 4
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
• RUVRAIGXERUAHV-UHFFFAOYSA-N tert-butyl 3,5-dioxopiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=O)NC(=O)C1 RUVRAIGXERUAHV-UHFFFAOYSA-N 0.000 description 4
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