SA04250088A - مركبات كيميائية - Google Patents

Info

Publication number

SA04250088A

SA04250088A SA04250088A SA04250088A SA04250088A SA 04250088 A SA04250088 A SA 04250088A SA 04250088 A SA04250088 A SA 04250088A SA 04250088 A SA04250088 A SA 04250088A SA 04250088 A SA04250088 A SA 04250088A

Authority

SA

Saudi Arabia

Prior art keywords

alkyl

cra

ring

group

alkoxy

Prior art date

2002-11-28

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 298
• 150000002148 esters Chemical class 0.000 claims abstract description 138
• 238000006467 substitution reaction Methods 0.000 claims abstract description 127
• 150000003839 salts Chemical class 0.000 claims abstract description 125
• 239000000203 mixture Substances 0.000 claims abstract description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 97
• 238000000034 method Methods 0.000 claims abstract description 53
• 239000003242 anti bacterial agent Substances 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 358
• -1 cyano, carboxy Chemical group 0.000 claims description 267
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 142
• 125000003545 alkoxy group Chemical group 0.000 claims description 128
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 111
• 125000001424 substituent group Chemical group 0.000 claims description 97
• 239000001257 hydrogen Substances 0.000 claims description 89
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 83
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
• 229910052757 nitrogen Inorganic materials 0.000 claims description 67
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 57
• 125000004429 atom Chemical group 0.000 claims description 55
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
• 229910052799 carbon Inorganic materials 0.000 claims description 49
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 41
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 125000003342 alkenyl group Chemical group 0.000 claims description 35
• 150000001721 carbon Chemical group 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
• BKIKLVNBFSQWGA-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-prop-2-enyl-6h-1,3,4-thiadiazin-2-amine Chemical compound C1=CC(Cl)=CC=C1C1=NN=C(NCC=C)SC1 BKIKLVNBFSQWGA-UHFFFAOYSA-N 0.000 claims description 25
• 238000001727 in vivo Methods 0.000 claims description 25
• 150000003852 triazoles Chemical class 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 238000006243 chemical reaction Methods 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
• 125000001246 bromo group Chemical group Br* 0.000 claims description 18
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• 230000008569 process Effects 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 230000000844 anti-bacterial effect Effects 0.000 claims description 14
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000004122 cyclic group Chemical group 0.000 claims description 13
• 125000004043 oxo group Chemical group O=* 0.000 claims description 13
• 230000004224 protection Effects 0.000 claims description 13
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 12
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 12
• 229920002554 vinyl polymer Polymers 0.000 claims description 11
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 241000894006 Bacteria Species 0.000 claims description 9
• 125000001475 halogen functional group Chemical group 0.000 claims description 9
• TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 claims description 9
• 229910052763 palladium Inorganic materials 0.000 claims description 9
• 241001465754 Metazoa Species 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 7
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
• 235000013343 vitamin Nutrition 0.000 claims description 7
• 239000011782 vitamin Substances 0.000 claims description 7
• 229940088594 vitamin Drugs 0.000 claims description 7
• 229930003231 vitamin Natural products 0.000 claims description 7
• 150000003722 vitamin derivatives Chemical class 0.000 claims description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
• 150000001540 azides Chemical class 0.000 claims description 5
• 125000001589 carboacyl group Chemical group 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 150000002825 nitriles Chemical class 0.000 claims description 5
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 230000000295 complement effect Effects 0.000 claims description 4
• 238000005859 coupling reaction Methods 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 238000006073 displacement reaction Methods 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• 238000009472 formulation Methods 0.000 claims description 4
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
• 210000001699 lower leg Anatomy 0.000 claims description 4
• 230000003647 oxidation Effects 0.000 claims description 4
• 238000007254 oxidation reaction Methods 0.000 claims description 4
• 125000004423 acyloxy group Chemical group 0.000 claims description 3
• 150000001336 alkenes Chemical class 0.000 claims description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 150000001805 chlorine compounds Chemical class 0.000 claims description 3
• RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 claims description 3
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 239000003701 inert diluent Substances 0.000 claims description 3
• 150000002923 oximes Chemical class 0.000 claims description 3
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• 239000000758 substrate Substances 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• 102100033380 Chordin Human genes 0.000 claims description 2
• 241000192125 Firmicutes Species 0.000 claims description 2
• 101000943798 Homo sapiens Chordin Proteins 0.000 claims description 2
• NDGBLTXHLFJWAK-UHFFFAOYSA-N N-p-coumaroyltyramine Natural products Oc1ccc(CCNC(=O)C2=CC(=O)Oc3ccccc23)cc1 NDGBLTXHLFJWAK-UHFFFAOYSA-N 0.000 claims description 2
• 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 150000001413 amino acids Chemical class 0.000 claims description 2
• 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
• 238000006555 catalytic reaction Methods 0.000 claims description 2
• 239000000039 congener Substances 0.000 claims description 2
• 230000001268 conjugating effect Effects 0.000 claims description 2
• 238000006352 cycloaddition reaction Methods 0.000 claims description 2
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
• 239000010437 gem Substances 0.000 claims description 2
• 239000012948 isocyanate Substances 0.000 claims description 2
• 150000002513 isocyanates Chemical class 0.000 claims description 2
• 210000002414 leg Anatomy 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 150000003254 radicals Chemical class 0.000 claims description 2
• 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 2
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
• RXGUTQNKCXHALN-BJMVGYQFSA-N trans-N-p-coumaroyl tyramine Chemical group C1=CC(O)=CC=C1CCNC(=O)\C=C\C1=CC=C(O)C=C1 RXGUTQNKCXHALN-BJMVGYQFSA-N 0.000 claims description 2
• 230000009466 transformation Effects 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
• ZVLQRVVUXPUBIU-UHFFFAOYSA-N (2,2-dimethylhydrazinyl)methanamine Chemical compound NCNN(C)C ZVLQRVVUXPUBIU-UHFFFAOYSA-N 0.000 claims 1
• YXDXXGXWFJCXEB-UHFFFAOYSA-N 2-furonitrile Chemical compound N#CC1=CC=CO1 YXDXXGXWFJCXEB-UHFFFAOYSA-N 0.000 claims 1
• 241001103870 Adia Species 0.000 claims 1
• 241001549627 Havetia Species 0.000 claims 1
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
• 125000000304 alkynyl group Chemical group 0.000 claims 1
• 229910002056 binary alloy Inorganic materials 0.000 claims 1
• 210000004556 brain Anatomy 0.000 claims 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 230000003197 catalytic effect Effects 0.000 claims 1
• 239000004927 clay Substances 0.000 claims 1
• 238000012851 eutrophication Methods 0.000 claims 1
• 150000004678 hydrides Chemical class 0.000 claims 1
• FRQMUZJSZHZSGN-HBNHAYAOSA-N medroxyprogesterone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FRQMUZJSZHZSGN-HBNHAYAOSA-N 0.000 claims 1
• 229960004616 medroxyprogesterone Drugs 0.000 claims 1
• 229910052751 metal Inorganic materials 0.000 claims 1
• 239000002184 metal Substances 0.000 claims 1
• 150000002739 metals Chemical class 0.000 claims 1
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 1
• 230000001681 protective effect Effects 0.000 claims 1
• 239000000376 reactant Substances 0.000 claims 1
• 150000003573 thiols Chemical class 0.000 claims 1
• 229910052731 fluorine Inorganic materials 0.000 abstract description 39
• 125000001425 triazolyl group Chemical group 0.000 abstract description 3
• 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
• 125000003831 tetrazolyl group Chemical group 0.000 abstract description 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 295
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 283
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 196
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
• 239000007787 solid Substances 0.000 description 106
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
• 235000019439 ethyl acetate Nutrition 0.000 description 95
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 92
• 239000000243 solution Substances 0.000 description 86
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
• 239000011541 reaction mixture Substances 0.000 description 61
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 59
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
• 238000005481 NMR spectroscopy Methods 0.000 description 54
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
• 238000005160 1H NMR spectroscopy Methods 0.000 description 49
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
• 239000000741 silica gel Substances 0.000 description 45
• 229910002027 silica gel Inorganic materials 0.000 description 45
• 229960001866 silicon dioxide Drugs 0.000 description 45
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 42
• 239000003921 oil Substances 0.000 description 42
• 235000019198 oils Nutrition 0.000 description 42
• 239000000047 product Substances 0.000 description 39
• 239000011737 fluorine Substances 0.000 description 34
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 33
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
• 229910052938 sodium sulfate Inorganic materials 0.000 description 32
• 235000011152 sodium sulphate Nutrition 0.000 description 32
• 239000000543 intermediate Substances 0.000 description 30
• 239000011575 calcium Substances 0.000 description 27
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 26
• 238000007792 addition Methods 0.000 description 25
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 24
• 229910000027 potassium carbonate Inorganic materials 0.000 description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 22
• 238000003818 flash chromatography Methods 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 21
• 239000012074 organic phase Substances 0.000 description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 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 19
• 239000012044 organic layer Substances 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
• YYXVNWBGVIIBOW-QMMMGPOBSA-N [(3s)-4-hydroxy-3-[(4-oxo-1,5-dihydropyrrolo[3,2-d]pyrimidin-7-yl)methylamino]butyl]phosphonic acid Chemical compound N1=CNC(=O)C2=C1C(CN[C@@H](CCP(O)(O)=O)CO)=CN2 YYXVNWBGVIIBOW-QMMMGPOBSA-N 0.000 description 17
• 125000002252 acyl group Chemical group 0.000 description 17
• 238000004440 column chromatography Methods 0.000 description 16
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 16
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 15
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
• 235000019341 magnesium sulphate Nutrition 0.000 description 15
• 238000002844 melting Methods 0.000 description 15
• 230000008018 melting Effects 0.000 description 15
• 229940002612 prodrug Drugs 0.000 description 15
• 239000000651 prodrug Substances 0.000 description 15
• 239000002253 acid Substances 0.000 description 14
• 238000004587 chromatography analysis Methods 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• 125000001786 isothiazolyl group Chemical group 0.000 description 13
• 239000000463 material Substances 0.000 description 13
• 239000002244 precipitate Substances 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 12
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 239000000126 substance Substances 0.000 description 12
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
• 150000003536 tetrazoles Chemical class 0.000 description 12
• KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 11
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