HRP20030694A2 - Composition and antiviral activity of substitutedazaindoleoxoacetic piperazine derivatives - Google Patents

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Publication number

HRP20030694A2

HRP20030694A2 HR20030694A HRP20030694A HRP20030694A2 HR P20030694 A2 HRP20030694 A2 HR P20030694A2 HR 20030694 A HR20030694 A HR 20030694A HR P20030694 A HRP20030694 A HR P20030694A HR P20030694 A2 HRP20030694 A2 HR P20030694A2

Authority

HR

Croatia

Prior art keywords

group

alkyl

heteroaryl

aryl

optionally substituted

Prior art date

2001-02-02

Links

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• 230000000840 anti-viral effect Effects 0.000 title claims description 7
• 239000000203 mixture Substances 0.000 title description 42
• 150000004885 piperazines Chemical class 0.000 title description 17
• 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 278
• 238000000034 method Methods 0.000 claims description 225
• 229910052736 halogen Inorganic materials 0.000 claims description 194
• -1 benzo- imidazolyl Chemical group 0.000 claims description 193
• 150000002367 halogens Chemical class 0.000 claims description 190
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 173
• 150000001875 compounds Chemical class 0.000 claims description 170
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 168
• 125000003118 aryl group Chemical group 0.000 claims description 161
• 229910052739 hydrogen Inorganic materials 0.000 claims description 147
• 239000001257 hydrogen Substances 0.000 claims description 131
• 125000001424 substituent group Chemical group 0.000 claims description 123
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 100
• 208000030507 AIDS Diseases 0.000 claims description 74
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 73
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 67
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
• 125000000304 alkynyl group Chemical group 0.000 claims description 59
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 55
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 51
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 50
• 208000031886 HIV Infections Diseases 0.000 claims description 48
• 208000037357 HIV infectious disease Diseases 0.000 claims description 45
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 45
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 36
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 34
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
• 125000001544 thienyl group Chemical group 0.000 claims description 33
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 32
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
• 125000004122 cyclic group Chemical group 0.000 claims description 28
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 25
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• 125000002541 furyl group Chemical group 0.000 claims description 25
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 24
• 238000011282 treatment Methods 0.000 claims description 24
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 23
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
• 125000004104 aryloxy group Chemical group 0.000 claims description 19
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 229910052796 boron Inorganic materials 0.000 claims description 17
• 125000005296 thioaryloxy group Chemical group 0.000 claims description 17
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 15
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 15
• 125000005404 thioheteroaryloxy group Chemical group 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 13
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 13
• 150000003536 tetrazoles Chemical group 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 12
• 125000005190 thiohydroxy group Chemical group 0.000 claims description 12
• 150000003852 triazoles Chemical group 0.000 claims description 12
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 11
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 9
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 9
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 9
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 9
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000005499 phosphonyl group Chemical group 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 7
• 241000700605 Viruses Species 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 125000004306 triazinyl group Chemical group 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 6
• 239000002955 immunomodulating agent Substances 0.000 claims description 6
• 229940121354 immunomodulator Drugs 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 239000011593 sulfur Substances 0.000 claims description 5
• 229910003827 NRaRb Inorganic materials 0.000 claims description 4
• 229960005475 antiinfective agent Drugs 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 208000015181 infectious disease Diseases 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 239000004599 antimicrobial Substances 0.000 claims description 3
• 150000001721 carbon Chemical group 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 229940124530 sulfonamide Drugs 0.000 claims description 3
• 150000003456 sulfonamides Chemical class 0.000 claims description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 45
• 150000002431 hydrogen Chemical class 0.000 claims 13
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 8
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 8
• VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims 7
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 7
• 125000006413 ring segment Chemical group 0.000 claims 7
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 4
• 125000002619 bicyclic group Chemical group 0.000 claims 4
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
• 125000004069 aziridinyl group Chemical group 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 230000002584 immunomodulator Effects 0.000 claims 1
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 1
• 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
• WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims 1
• 125000004001 thioalkyl group Chemical group 0.000 claims 1
• 239000000543 intermediate Substances 0.000 description 237
• 238000006243 chemical reaction Methods 0.000 description 119
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
• 238000002360 preparation method Methods 0.000 description 57
• 238000004128 high performance liquid chromatography Methods 0.000 description 55
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
• 230000015572 biosynthetic process Effects 0.000 description 50
• 230000014759 maintenance of location Effects 0.000 description 49
• 238000004949 mass spectrometry Methods 0.000 description 48
• 239000002904 solvent Substances 0.000 description 48
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• 229910001868 water Inorganic materials 0.000 description 40
• 239000002253 acid Substances 0.000 description 38
• 238000003786 synthesis reaction Methods 0.000 description 38
• 125000000623 heterocyclic group Chemical group 0.000 description 37
• 239000000243 solution Substances 0.000 description 34
• 235000019439 ethyl acetate Nutrition 0.000 description 32
• 150000001299 aldehydes Chemical group 0.000 description 31
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 29
• 238000005859 coupling reaction Methods 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 28
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 27
• 230000008878 coupling Effects 0.000 description 26
• 238000010168 coupling process Methods 0.000 description 26
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
• 150000001412 amines Chemical class 0.000 description 23
• 239000002585 base Substances 0.000 description 23
• 239000003153 chemical reaction reagent Substances 0.000 description 23
• HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 22
• 229960002555 zidovudine Drugs 0.000 description 22
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 20
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 20
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
• 230000009466 transformation Effects 0.000 description 20
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 19
• 239000002244 precipitate Substances 0.000 description 19
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 18
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 18
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 18
• 239000007787 solid Substances 0.000 description 18
• 150000001204 N-oxides Chemical class 0.000 description 17
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• 239000003814 drug Substances 0.000 description 16
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
• 239000000047 product Substances 0.000 description 16
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
• 150000002825 nitriles Chemical class 0.000 description 15
• 239000012044 organic layer Substances 0.000 description 15
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 15
• 238000010898 silica gel chromatography Methods 0.000 description 15
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
• 235000019341 magnesium sulphate Nutrition 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 13
• 229940079593 drug Drugs 0.000 description 13
• 230000003647 oxidation Effects 0.000 description 13
• 238000007254 oxidation reaction Methods 0.000 description 13
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 150000001408 amides Chemical class 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 230000007062 hydrolysis Effects 0.000 description 12
• 238000006460 hydrolysis reaction Methods 0.000 description 12
• 239000003112 inhibitor Substances 0.000 description 12
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 12
• VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 description 12
• 238000000844 transformation Methods 0.000 description 12
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