NZ552405A - Pyrrolidine containing antiviral compounds - Google Patents

Info

Publication number

NZ552405A

NZ552405A NZ552405A NZ55240505A NZ552405A NZ 552405 A NZ552405 A NZ 552405A NZ 552405 A NZ552405 A NZ 552405A NZ 55240505 A NZ55240505 A NZ 55240505A NZ 552405 A NZ552405 A NZ 552405A

Authority

NZ

New Zealand

Prior art keywords

alkyl

cycloalkyl

optionally substituted

alkenyl

alkynyl

Prior art date

2004-07-16

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 237
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title description 15
• 230000000840 anti-viral effect Effects 0.000 title description 6
• -1 pyrrolidinyl compound Chemical class 0.000 claims abstract description 397
• 239000003814 drug Substances 0.000 claims abstract description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
• 208000005176 Hepatitis C Diseases 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 457
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 187
• 238000000034 method Methods 0.000 claims description 176
• 125000000623 heterocyclic group Chemical group 0.000 claims description 138
• 125000003342 alkenyl group Chemical group 0.000 claims description 134
• 125000000304 alkynyl group Chemical group 0.000 claims description 126
• 125000003118 aryl group Chemical group 0.000 claims description 125
• 229910052736 halogen Inorganic materials 0.000 claims description 119
• 125000001072 heteroaryl group Chemical group 0.000 claims description 114
• 150000002367 halogens Chemical class 0.000 claims description 96
• 229910052757 nitrogen Inorganic materials 0.000 claims description 93
• 229910052760 oxygen Inorganic materials 0.000 claims description 90
• 229910052799 carbon Inorganic materials 0.000 claims description 81
• 229910052717 sulfur Inorganic materials 0.000 claims description 76
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 69
• 150000003839 salts Chemical class 0.000 claims description 59
• 125000003545 alkoxy group Chemical group 0.000 claims description 54
• 125000001188 haloalkyl group Chemical group 0.000 claims description 51
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 48
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 48
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 48
• 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 48
• 125000004104 aryloxy group Chemical group 0.000 claims description 48
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
• 229940124530 sulfonamide Drugs 0.000 claims description 48
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
• 125000004432 carbon atom Chemical group C* 0.000 claims description 43
• 150000001413 amino acids Chemical class 0.000 claims description 41
• 239000012453 solvate Substances 0.000 claims description 28
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 27
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 24
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 24
• 125000003368 amide group Chemical group 0.000 claims description 24
• 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 229940079322 interferon Drugs 0.000 claims description 10
• 102000014150 Interferons Human genes 0.000 claims description 8
• 108010050904 Interferons Proteins 0.000 claims description 8
• 239000002777 nucleoside Substances 0.000 claims description 8
• 229940127073 nucleoside analogue Drugs 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 2
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 2
• 229950003954 isatoribine Drugs 0.000 claims description 2
• 229960000329 ribavirin Drugs 0.000 claims description 2
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 2
• 229950006081 taribavirin Drugs 0.000 claims description 2
• TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 1
• NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 abstract description 65
• 229910052698 phosphorus Inorganic materials 0.000 abstract description 22
• 238000004519 manufacturing process Methods 0.000 abstract description 6
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 3
• 239000011574 phosphorus Substances 0.000 abstract description 3
• 238000006243 chemical reaction Methods 0.000 description 112
• 239000000047 product Substances 0.000 description 105
• 239000000203 mixture Substances 0.000 description 97
• 239000000651 prodrug Substances 0.000 description 71
• 229940002612 prodrug Drugs 0.000 description 71
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 66
• 229940024606 amino acid Drugs 0.000 description 65
• 235000001014 amino acid Nutrition 0.000 description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 60
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 52
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• 238000002360 preparation method Methods 0.000 description 50
• 150000002148 esters Chemical class 0.000 description 49
• 239000004480 active ingredient Substances 0.000 description 46
• 125000005842 heteroatom Chemical group 0.000 description 46
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 44
• 125000006239 protecting group Chemical group 0.000 description 44
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 43
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 239000000543 intermediate Substances 0.000 description 36
• 108090000765 processed proteins & peptides Proteins 0.000 description 36
• 239000002585 base Substances 0.000 description 35
• 239000000243 solution Substances 0.000 description 35
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
• 238000009472 formulation Methods 0.000 description 34
• 125000005843 halogen group Chemical group 0.000 description 34
• 102000004196 processed proteins & peptides Human genes 0.000 description 34
• 239000002253 acid Substances 0.000 description 32
• 150000001412 amines Chemical class 0.000 description 31
• 229920001184 polypeptide Polymers 0.000 description 31
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
• 238000003786 synthesis reaction Methods 0.000 description 29
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• 230000015572 biosynthetic process Effects 0.000 description 27
• 150000001721 carbon Chemical group 0.000 description 27
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 27
• 150000005690 diesters Chemical class 0.000 description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
• 229940079593 drug Drugs 0.000 description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 23
• 125000005213 alkyl heteroaryl group Chemical group 0.000 description 22
• 125000005037 alkyl phenyl group Chemical group 0.000 description 22
• 125000002837 carbocyclic group Chemical group 0.000 description 22
• 239000003153 chemical reaction reagent Substances 0.000 description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 description 22
• 230000000694 effects Effects 0.000 description 21
• 230000002378 acidificating effect Effects 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• 125000004430 oxygen atom Chemical group O* 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 125000004429 atom Chemical group 0.000 description 18
• 210000004027 cell Anatomy 0.000 description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• 229910001868 water Inorganic materials 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• 150000001408 amides Chemical class 0.000 description 17
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
• 238000003776 cleavage reaction Methods 0.000 description 16
• 238000001727 in vivo Methods 0.000 description 16
• 150000003009 phosphonic acids Chemical class 0.000 description 16
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 15
• 229940059260 amidate Drugs 0.000 description 15
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 15
• 239000003795 chemical substances by application Substances 0.000 description 15
• 238000005859 coupling reaction Methods 0.000 description 15
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 150000002440 hydroxy compounds Chemical class 0.000 description 14
• 230000002401 inhibitory effect Effects 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• 230000007017 scission Effects 0.000 description 14
• 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 14
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 13
• 241000282414 Homo sapiens Species 0.000 description 13
• NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 13
• 125000000524 functional group Chemical group 0.000 description 13
• 102000004190 Enzymes Human genes 0.000 description 12
• 108090000790 Enzymes Proteins 0.000 description 12
• 238000006460 hydrolysis reaction Methods 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 239000000546 pharmaceutical excipient Substances 0.000 description 12
• 238000000926 separation method Methods 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
• 125000000539 amino acid group Chemical group 0.000 description 11
• 230000007062 hydrolysis Effects 0.000 description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 11
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 11
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 10
• 235000019439 ethyl acetate Nutrition 0.000 description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
• 239000007788 liquid Substances 0.000 description 10
• 239000002207 metabolite Substances 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000000376 reactant Substances 0.000 description 10
• 239000000523 sample Substances 0.000 description 10
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• 241001465754 Metazoa Species 0.000 description 9
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
• 239000003960 organic solvent Substances 0.000 description 9
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 9
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• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 238000006751 Mitsunobu reaction Methods 0.000 description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
• 239000012620 biological material Substances 0.000 description 8
• 210000004369 blood Anatomy 0.000 description 8
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• 239000007822 coupling agent Substances 0.000 description 8
• 235000014113 dietary fatty acids Nutrition 0.000 description 8
• 125000004185 ester group Chemical group 0.000 description 8
• LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
• 229930195729 fatty acid Natural products 0.000 description 8
• 239000000194 fatty acid Substances 0.000 description 8
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• 238000000338 in vitro Methods 0.000 description 8
• 230000003287 optical effect Effects 0.000 description 8
• 230000001225 therapeutic effect Effects 0.000 description 8
• 238000004679 31P NMR spectroscopy Methods 0.000 description 7
• 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 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
• ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• ROBXZHNBBCHEIQ-BYPYZUCNSA-N ethyl (2s)-2-aminopropanoate Chemical compound CCOC(=O)[C@H](C)N ROBXZHNBBCHEIQ-BYPYZUCNSA-N 0.000 description 7
• 229940093499 ethyl acetate Drugs 0.000 description 7
• 230000006870 function Effects 0.000 description 7
• 125000002883 imidazolyl group Chemical group 0.000 description 7
• 239000004615 ingredient Substances 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 230000003834 intracellular effect Effects 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
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• 102000004169 proteins and genes Human genes 0.000 description 7
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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 125000003158 alcohol group Chemical group 0.000 description 6
• HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 6
• 125000003277 amino group Chemical group 0.000 description 6
• 150000001718 carbodiimides Chemical class 0.000 description 6
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 239000006071 cream Substances 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
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• 210000001035 gastrointestinal tract Anatomy 0.000 description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 239000002243 precursor Substances 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 description 6
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• 230000032258 transport Effects 0.000 description 6
• NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 5
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
• 229910019142 PO4 Inorganic materials 0.000 description 5
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 5
• 238000005804 alkylation reaction Methods 0.000 description 5
• 239000007900 aqueous suspension Substances 0.000 description 5
• 230000037396 body weight Effects 0.000 description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 239000012973 diazabicyclooctane Substances 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 238000006073 displacement reaction Methods 0.000 description 5
• 239000003925 fat Substances 0.000 description 5
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• 235000013355 food flavoring agent Nutrition 0.000 description 5
• 235000003599 food sweetener Nutrition 0.000 description 5
• 239000008187 granular material Substances 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 5
• 230000002163 immunogen Effects 0.000 description 5
• 210000004185 liver Anatomy 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 125000003835 nucleoside group Chemical group 0.000 description 5
• 235000021317 phosphate Nutrition 0.000 description 5
• 239000003495 polar organic solvent Substances 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• 239000003755 preservative agent Substances 0.000 description 5
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