OA11575A - Fluorophenyl resin compounds. - Google Patents

Info

Publication number

OA11575A

OA11575A OA1200000353A OA1200000353A OA11575A OA 11575 A OA11575 A OA 11575A OA 1200000353 A OA1200000353 A OA 1200000353A OA 1200000353 A OA1200000353 A OA 1200000353A OA 11575 A OA11575 A OA 11575A

Authority

OA

OAPI

Prior art keywords

compound

resin

fluorophenyl

resin compound

formula

Prior art date

1998-06-24

Links

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• 229920005989 resin Polymers 0.000 title claims abstract description 317
• 239000011347 resin Substances 0.000 title claims abstract description 317
• 150000001875 compounds Chemical class 0.000 title claims abstract description 170
• 125000001207 fluorophenyl group Chemical group 0.000 title claims abstract description 138
• -1 carbonates carbamates Chemical class 0.000 claims abstract description 178
• 238000000034 method Methods 0.000 claims abstract description 39
• 150000001408 amides Chemical class 0.000 claims abstract description 28
• 150000001412 amines Chemical class 0.000 claims abstract description 27
• 229940124530 sulfonamide Drugs 0.000 claims abstract description 7
• 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 4
• 125000003118 aryl group Chemical group 0.000 claims description 91
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 86
• 229920005990 polystyrene resin Polymers 0.000 claims description 65
• 125000001931 aliphatic group Chemical group 0.000 claims description 59
• MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 34
• 238000004519 manufacturing process Methods 0.000 claims description 32
• 229910052799 carbon Inorganic materials 0.000 claims description 30
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical group CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 27
• BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 25
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 25
• 238000005859 coupling reaction Methods 0.000 claims description 23
• 239000000126 substance Substances 0.000 claims description 21
• 230000008878 coupling Effects 0.000 claims description 20
• 238000010168 coupling process Methods 0.000 claims description 20
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
• 125000004429 atom Chemical group 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 230000008569 process Effects 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 230000003213 activating effect Effects 0.000 claims description 11
• 239000012038 nucleophile Substances 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 229920003180 amino resin Polymers 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
• 229910006069 SO3H Inorganic materials 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical group OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 6
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 4
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
• 150000003573 thiols Chemical class 0.000 claims description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical group CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
• 239000002841 Lewis acid Substances 0.000 claims description 3
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 150000007517 lewis acids Chemical class 0.000 claims description 3
• RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical group [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 claims description 3
• 229940043349 potassium metabisulfite Drugs 0.000 claims description 3
• 235000010263 potassium metabisulphite Nutrition 0.000 claims description 3
• FJSAJUXIHJIAMD-UHFFFAOYSA-N 2,4-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(F)=C1 FJSAJUXIHJIAMD-UHFFFAOYSA-N 0.000 claims description 2
• JSWRVDNTKPAJLB-UHFFFAOYSA-N 2,4-difluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(F)=C1 JSWRVDNTKPAJLB-UHFFFAOYSA-N 0.000 claims description 2
• 239000002168 alkylating agent Substances 0.000 claims description 2
• 229940100198 alkylating agent Drugs 0.000 claims description 2
• 229910052794 bromium Inorganic materials 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 2
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
• 239000012948 isocyanate Substances 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
• 229940116441 divinylbenzene Drugs 0.000 claims 4
• SBGUYEPUJPATFD-UHFFFAOYSA-N bromo(tripyrrolidin-1-yl)phosphanium Chemical compound C1CCCN1[P+](N1CCCC1)(Br)N1CCCC1 SBGUYEPUJPATFD-UHFFFAOYSA-N 0.000 claims 2
• 150000007522 mineralic acids Chemical class 0.000 claims 2
• 239000003444 phase transfer catalyst Substances 0.000 claims 2
• 229910017711 NHRa Inorganic materials 0.000 claims 1
• 239000004793 Polystyrene Substances 0.000 claims 1
• JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims 1
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
• 229920002223 polystyrene Polymers 0.000 claims 1
• 108090000765 processed proteins & peptides Proteins 0.000 abstract description 29
• 102000004196 processed proteins & peptides Human genes 0.000 abstract description 13
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract description 7
• 238000010532 solid phase synthesis reaction Methods 0.000 abstract description 6
• 150000003456 sulfonamides Chemical class 0.000 abstract description 6
• 150000003673 urethanes Chemical class 0.000 abstract description 3
• 238000002360 preparation method Methods 0.000 abstract 1
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 245
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 98
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
• 238000006243 chemical reaction Methods 0.000 description 60
• 150000002148 esters Chemical class 0.000 description 49
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 39
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
• 239000000203 mixture Substances 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 239000007787 solid Substances 0.000 description 30
• 125000006413 ring segment Chemical group 0.000 description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• 230000015572 biosynthetic process Effects 0.000 description 24
• 238000003776 cleavage reaction Methods 0.000 description 23
• 235000001014 amino acid Nutrition 0.000 description 20
• 229940024606 amino acid Drugs 0.000 description 20
• 239000000243 solution Substances 0.000 description 20
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 19
• 150000001413 amino acids Chemical class 0.000 description 19
• 125000004432 carbon atom Chemical group C* 0.000 description 19
• 150000003254 radicals Chemical class 0.000 description 19
• 239000011541 reaction mixture Substances 0.000 description 19
• 239000003153 chemical reaction reagent Substances 0.000 description 18
• 239000003960 organic solvent Substances 0.000 description 18
• 230000007017 scission Effects 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
• 239000002253 acid Substances 0.000 description 17
• 125000000623 heterocyclic group Chemical group 0.000 description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 15
• 125000006239 protecting group Chemical group 0.000 description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
• 125000003710 aryl alkyl group Chemical group 0.000 description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
• 125000000753 cycloalkyl group Chemical group 0.000 description 13
• 229910052760 oxygen Inorganic materials 0.000 description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• 150000001204 N-oxides Chemical class 0.000 description 12
• 125000005466 alkylenyl group Chemical group 0.000 description 12
• 239000001301 oxygen Substances 0.000 description 12
• GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 12
• HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 11
• UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 11
• 125000004122 cyclic group Chemical group 0.000 description 11
• 125000000392 cycloalkenyl group Chemical group 0.000 description 11
• 238000002156 mixing Methods 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
• 125000000304 alkynyl group Chemical group 0.000 description 10
• 125000004475 heteroaralkyl group Chemical group 0.000 description 10
• 238000011068 loading method Methods 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 9
• 241000534944 Thia Species 0.000 description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 9
• 125000004434 sulfur atom Chemical group 0.000 description 9
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 8
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 8
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 8
• 239000004472 Lysine Substances 0.000 description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
• 125000002252 acyl group Chemical group 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 8
• 125000000524 functional group Chemical group 0.000 description 8
• 235000018977 lysine Nutrition 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• 239000004743 Polypropylene Substances 0.000 description 7
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
• 229920001155 polypropylene Polymers 0.000 description 7
• 239000007790 solid phase Substances 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 125000004350 aryl cycloalkyl group Chemical group 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 6
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
• 238000010647 peptide synthesis reaction Methods 0.000 description 6
• 229920000642 polymer Polymers 0.000 description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 6
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
• 229940125844 compound 46 Drugs 0.000 description 5
• 125000001153 fluoro group Chemical group F* 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
• 125000004414 alkyl thio group Chemical group 0.000 description 4
• 125000002947 alkylene group Chemical group 0.000 description 4
• QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 4
• 125000000539 amino acid group Chemical group 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
• 125000006244 carboxylic acid protecting group Chemical group 0.000 description 4
• 229940125890 compound Ia Drugs 0.000 description 4
• 238000010511 deprotection reaction Methods 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
• 229940073584 methylene chloride Drugs 0.000 description 4
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 4
• ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 3
• FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 3
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 3
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
• NXWTWYULZRDBSA-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1F NXWTWYULZRDBSA-UHFFFAOYSA-N 0.000 description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
• TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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