KR20010024123A - 6-원 고리를 갖는 화합물, 그의 제조 방법 및의약물로서의 용도 - Google Patents
6-원 고리를 갖는 화합물, 그의 제조 방법 및의약물로서의 용도 Download PDFInfo
- Publication number
- KR20010024123A KR20010024123A KR1020007002880A KR20007002880A KR20010024123A KR 20010024123 A KR20010024123 A KR 20010024123A KR 1020007002880 A KR1020007002880 A KR 1020007002880A KR 20007002880 A KR20007002880 A KR 20007002880A KR 20010024123 A KR20010024123 A KR 20010024123A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- group
- groups
- carbon atoms
- independently
- Prior art date
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 569
- 238000000034 method Methods 0.000 title claims abstract description 233
- 230000008569 process Effects 0.000 title description 120
- 238000002360 preparation method Methods 0.000 title description 22
- 239000003814 drug Substances 0.000 title description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 43
- 108010006232 Neuraminidase Proteins 0.000 claims abstract description 40
- 102000005348 Neuraminidase Human genes 0.000 claims abstract description 39
- 230000002378 acidificating effect Effects 0.000 claims abstract description 35
- 230000000694 effects Effects 0.000 claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 160
- 125000004432 carbon atom Chemical group C* 0.000 claims description 92
- 239000002253 acid Substances 0.000 claims description 85
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 55
- 239000002904 solvent Chemical class 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 125000006239 protecting group Chemical group 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 239000002702 enteric coating Substances 0.000 claims description 18
- 238000009505 enteric coating Methods 0.000 claims description 18
- 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 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000004450 alkenylene group Chemical group 0.000 claims description 15
- 125000004419 alkynylene group Chemical group 0.000 claims description 15
- 238000001727 in vivo Methods 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 229910052736 halogen Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 7
- 206010022000 influenza Diseases 0.000 claims description 7
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000003536 tetrazoles Chemical class 0.000 claims description 6
- 239000003223 protective agent Substances 0.000 claims description 4
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229920000642 polymer Polymers 0.000 abstract description 17
- 239000000126 substance Substances 0.000 abstract description 16
- 238000012216 screening Methods 0.000 abstract description 8
- 238000003556 assay Methods 0.000 abstract description 7
- 239000003112 inhibitor Substances 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 2
- 230000000890 antigenic effect Effects 0.000 abstract 1
- -1 sulfonic acid halides Chemical class 0.000 description 333
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
- 235000019441 ethanol Nutrition 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 81
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 79
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000000243 solution Substances 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 229940024606 amino acid Drugs 0.000 description 56
- 235000001014 amino acid Nutrition 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 229910001868 water Inorganic materials 0.000 description 52
- 150000001413 amino acids Chemical class 0.000 description 51
- 108090000765 processed proteins & peptides Proteins 0.000 description 48
- 238000005481 NMR spectroscopy Methods 0.000 description 46
- 102000004196 processed proteins & peptides Human genes 0.000 description 44
- 150000001412 amines Chemical class 0.000 description 43
- 235000019439 ethyl acetate Nutrition 0.000 description 43
- 239000000543 intermediate Substances 0.000 description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
- 229920001184 polypeptide Polymers 0.000 description 40
- 239000002585 base Substances 0.000 description 39
- 150000002148 esters Chemical class 0.000 description 38
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 239000004480 active ingredient Substances 0.000 description 36
- 239000003153 chemical reaction reagent Substances 0.000 description 33
- 238000009472 formulation Methods 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- 239000003377 acid catalyst Substances 0.000 description 27
- 150000001408 amides Chemical class 0.000 description 27
- 150000001540 azides Chemical class 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000003818 flash chromatography Methods 0.000 description 24
- 239000003826 tablet Substances 0.000 description 24
- 238000011282 treatment Methods 0.000 description 24
- 239000012190 activator Substances 0.000 description 22
- 239000012267 brine Substances 0.000 description 22
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 21
- 230000002163 immunogen Effects 0.000 description 21
- 239000000546 pharmaceutical excipient Substances 0.000 description 21
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
- 239000002552 dosage form Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 17
- 239000003638 chemical reducing agent Substances 0.000 description 17
- 229940086542 triethylamine Drugs 0.000 description 17
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 102000004190 Enzymes Human genes 0.000 description 15
- 108090000790 Enzymes Proteins 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- 229940093499 ethyl acetate Drugs 0.000 description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 15
- 230000003213 activating effect Effects 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 150000002009 diols Chemical group 0.000 description 14
- 230000007062 hydrolysis Effects 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 13
- 239000008187 granular material Substances 0.000 description 13
- 239000002207 metabolite Substances 0.000 description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 150000002924 oxiranes Chemical class 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 235000018102 proteins Nutrition 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 125000006413 ring segment Chemical group 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 230000004913 activation Effects 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 239000002775 capsule Substances 0.000 description 11
- 150000001721 carbon Chemical group 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
- 230000000968 intestinal effect Effects 0.000 description 11
- 239000012038 nucleophile Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 101150065749 Churc1 gene Proteins 0.000 description 10
- 102100038239 Protein Churchill Human genes 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 125000000539 amino acid group Chemical group 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 9
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 9
- VHVGFEDTMPYCSX-UHFFFAOYSA-N [1-[[2,2-dimethyl-3-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]propoxy]methyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCC(C)(C)COCN1C=CC(=C[NH+]=O)C=C1 VHVGFEDTMPYCSX-UHFFFAOYSA-N 0.000 description 9
- 238000012377 drug delivery Methods 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 238000007142 ring opening reaction Methods 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 150000003335 secondary amines Chemical class 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 230000009466 transformation Effects 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 239000002168 alkylating agent Substances 0.000 description 8
- 229940100198 alkylating agent Drugs 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- RZRJACCZWZTYJY-UHFFFAOYSA-N tert-butylsulfanyl n,n-dimethylcarbamodithioate Chemical group CN(C)C(=S)SSC(C)(C)C RZRJACCZWZTYJY-UHFFFAOYSA-N 0.000 description 8
- 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 8
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 7
- 102000035195 Peptidases Human genes 0.000 description 7
- 108091005804 Peptidases Proteins 0.000 description 7
- 241000700605 Viruses Species 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 description 7
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 241000712461 unidentified influenza virus Species 0.000 description 7
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000000010 aprotic solvent Substances 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- GDCRSXZBSIRSFR-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCOC(=O)C=C GDCRSXZBSIRSFR-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- PGZUMBJQJWIWGJ-ONAKXNSWSA-N oseltamivir phosphate Chemical compound OP(O)(O)=O.CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 PGZUMBJQJWIWGJ-ONAKXNSWSA-N 0.000 description 6
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 6
- 239000003586 protic polar solvent Substances 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 6
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000009498 subcoating Methods 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 5
- 108090000288 Glycoproteins Proteins 0.000 description 5
- 102000003886 Glycoproteins Human genes 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound 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 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000001409 amidines Chemical class 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- DTXOCJGLLMAFBX-UHFFFAOYSA-N oxo-[[1-[2-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]ethoxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCCOCN1C=CC(=C[NH+]=O)C=C1 DTXOCJGLLMAFBX-UHFFFAOYSA-N 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 229960000329 ribavirin Drugs 0.000 description 5
- 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 description 5
- 150000003460 sulfonic acids Chemical class 0.000 description 5
- 239000011593 sulfur Chemical group 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 5
- 150000000180 1,2-diols Chemical group 0.000 description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 108010016626 Dipeptides Proteins 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 108090000371 Esterases Proteins 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 125000006244 carboxylic acid protecting group Chemical group 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000013270 controlled release Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 4
- 208000037797 influenza A Diseases 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 235000019833 protease Nutrition 0.000 description 4
- 230000002633 protecting effect Effects 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000002911 sialidase inhibitor Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 230000017105 transposition Effects 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- RFABHELHVJVEPO-UHFFFAOYSA-N 1-nitrooctan-3-ol Chemical compound CCCCCC(O)CC[N+]([O-])=O RFABHELHVJVEPO-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
- ZCHHRLHTBGRGOT-SNAWJCMRSA-N 2-Hexen-1-ol Natural products CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 3
- KJTQHXTUICAYHG-UHFFFAOYSA-N 3-methyl-1-nitrobutan-2-ol Chemical compound CC(C)C(O)C[N+]([O-])=O KJTQHXTUICAYHG-UHFFFAOYSA-N 0.000 description 3
- MVFMATZFWFEEKJ-UHFFFAOYSA-N 3-methyl-3-nitrobutan-2-ol Chemical compound CC(O)C(C)(C)[N+]([O-])=O MVFMATZFWFEEKJ-UHFFFAOYSA-N 0.000 description 3
- OFEODFOGZSJOCW-UHFFFAOYSA-N 4-methyl-1-nitropentan-2-ol Chemical compound CC(C)CC(O)C[N+]([O-])=O OFEODFOGZSJOCW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical class CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 3
- 108010006303 Carboxypeptidases Proteins 0.000 description 3
- 102000005367 Carboxypeptidases Human genes 0.000 description 3
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 3
- 229920002785 Croscarmellose sodium Polymers 0.000 description 3
- 229920003134 Eudragit® polymer Polymers 0.000 description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000004473 Threonine Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
- 229960003121 arginine Drugs 0.000 description 3
- ICCBZGUDUOMNOF-UHFFFAOYSA-N azidoamine Chemical compound NN=[N+]=[N-] ICCBZGUDUOMNOF-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 210000001072 colon Anatomy 0.000 description 3
- 229960001681 croscarmellose sodium Drugs 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 230000009260 cross reactivity Effects 0.000 description 3
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000005676 cyclic carbonates Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical class CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 239000004220 glutamic acid Substances 0.000 description 3
- 235000013922 glutamic acid Nutrition 0.000 description 3
- 239000007902 hard capsule Substances 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 3
- 229960000310 isoleucine Drugs 0.000 description 3
- 125000000842 isoxazolyl group Chemical group 0.000 description 3
- 210000003750 lower gastrointestinal tract Anatomy 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 3
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 210000002345 respiratory system Anatomy 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 210000000813 small intestine Anatomy 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 150000003459 sulfonic acid esters Chemical class 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 150000007970 thio esters Chemical class 0.000 description 3
- 125000004149 thio group Chemical group *S* 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 230000005945 translocation Effects 0.000 description 3
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 3
- 229960004799 tryptophan Drugs 0.000 description 3
- 238000007039 two-step reaction Methods 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KLGNQHRPPLDIFC-MRVPVSSYSA-N (2r)-1-fluorooctan-2-ol Chemical compound CCCCCC[C@@H](O)CF KLGNQHRPPLDIFC-MRVPVSSYSA-N 0.000 description 2
- KJTQHXTUICAYHG-YFKPBYRVSA-N (2r)-3-methyl-1-nitrobutan-2-ol Chemical compound CC(C)[C@@H](O)C[N+]([O-])=O KJTQHXTUICAYHG-YFKPBYRVSA-N 0.000 description 2
- MVFMATZFWFEEKJ-SCSAIBSYSA-N (2r)-3-methyl-3-nitrobutan-2-ol Chemical compound C[C@@H](O)C(C)(C)[N+]([O-])=O MVFMATZFWFEEKJ-SCSAIBSYSA-N 0.000 description 2
- WYKTYEIIRULHNQ-SCSAIBSYSA-N (2r)-4-nitrobutan-2-ol Chemical compound C[C@@H](O)CC[N+]([O-])=O WYKTYEIIRULHNQ-SCSAIBSYSA-N 0.000 description 2
- QHSCIWIRXWFIGH-LURJTMIESA-N (2s)-2-amino-2-methylpentanedioic acid Chemical compound OC(=O)[C@](N)(C)CCC(O)=O QHSCIWIRXWFIGH-LURJTMIESA-N 0.000 description 2
- YSAZHINBXCWZTE-SCSAIBSYSA-N (3R)-3-fluorobutan-1-ol Chemical compound C[C@@H](F)CCO YSAZHINBXCWZTE-SCSAIBSYSA-N 0.000 description 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- OTIXUSNHAKOJBX-UHFFFAOYSA-N 1-(aziridin-1-yl)ethanone Chemical compound CC(=O)N1CC1 OTIXUSNHAKOJBX-UHFFFAOYSA-N 0.000 description 2
- GVEMIUUOJFZCOD-UHFFFAOYSA-N 1-fluoro-2-methylpropan-2-ol Chemical compound CC(C)(O)CF GVEMIUUOJFZCOD-UHFFFAOYSA-N 0.000 description 2
- SBUDCAVGUUUDNE-UHFFFAOYSA-N 1-fluoro-3,3-dimethylbutan-2-ol Chemical compound CC(C)(C)C(O)CF SBUDCAVGUUUDNE-UHFFFAOYSA-N 0.000 description 2
- MPGNSGYTEYWFIS-UHFFFAOYSA-N 1-fluorobutan-2-ol Chemical compound CCC(O)CF MPGNSGYTEYWFIS-UHFFFAOYSA-N 0.000 description 2
- KLGNQHRPPLDIFC-UHFFFAOYSA-N 1-fluorooctan-2-ol Chemical compound CCCCCCC(O)CF KLGNQHRPPLDIFC-UHFFFAOYSA-N 0.000 description 2
- FMEFHKJRIGHSLB-UHFFFAOYSA-N 1-nitrobutan-2-ol Chemical compound CCC(O)C[N+]([O-])=O FMEFHKJRIGHSLB-UHFFFAOYSA-N 0.000 description 2
- ZSOIKNVZUIEXAQ-UHFFFAOYSA-N 1-nitrododecan-2-ol Chemical compound CCCCCCCCCCC(O)C[N+]([O-])=O ZSOIKNVZUIEXAQ-UHFFFAOYSA-N 0.000 description 2
- VJCZJBJUAGHLEY-UHFFFAOYSA-N 1-nitroheptan-2-ol Chemical compound CCCCCC(O)C[N+]([O-])=O VJCZJBJUAGHLEY-UHFFFAOYSA-N 0.000 description 2
- UHUZCPVKBAPSSA-UHFFFAOYSA-N 1-nitrooctan-2-ol Chemical compound CCCCCCC(O)C[N+]([O-])=O UHUZCPVKBAPSSA-UHFFFAOYSA-N 0.000 description 2
- ACNMOTQCLBFDMQ-UHFFFAOYSA-N 1-nitropentan-2-ol Chemical compound CCCC(O)C[N+]([O-])=O ACNMOTQCLBFDMQ-UHFFFAOYSA-N 0.000 description 2
- MEGBNFNBKNPNQO-UHFFFAOYSA-N 10-fluorodecan-1-ol Chemical compound OCCCCCCCCCCF MEGBNFNBKNPNQO-UHFFFAOYSA-N 0.000 description 2
- BXNOMEIWVVVPOM-UHFFFAOYSA-N 11-fluoro-2-methylundecan-1-ol Chemical compound OCC(C)CCCCCCCCCF BXNOMEIWVVVPOM-UHFFFAOYSA-N 0.000 description 2
- DWUQJEHGOSZXLO-UHFFFAOYSA-N 11-fluoroundecan-1-ol Chemical compound OCCCCCCCCCCCF DWUQJEHGOSZXLO-UHFFFAOYSA-N 0.000 description 2
- NVMYVARFCPAXNR-UHFFFAOYSA-N 11-fluoroundecan-2-ol Chemical compound CC(O)CCCCCCCCCF NVMYVARFCPAXNR-UHFFFAOYSA-N 0.000 description 2
- PSXISJYLVGWDJC-UHFFFAOYSA-N 11-nitroundecan-1-ol Chemical compound OCCCCCCCCCCC[N+]([O-])=O PSXISJYLVGWDJC-UHFFFAOYSA-N 0.000 description 2
- DRHUCRLKSMPHDB-UHFFFAOYSA-N 12-fluorododecan-1-ol Chemical compound OCCCCCCCCCCCCF DRHUCRLKSMPHDB-UHFFFAOYSA-N 0.000 description 2
- FKLFIROEVCJXIF-UHFFFAOYSA-N 12-nitrododecan-1-ol Chemical compound OCCCCCCCCCCCC[N+]([O-])=O FKLFIROEVCJXIF-UHFFFAOYSA-N 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- AUWDOZOUJWEPBA-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethanol Chemical compound COC1=CC=C(CCO)C=C1 AUWDOZOUJWEPBA-UHFFFAOYSA-N 0.000 description 2
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- LQMAGZIWFASHJM-UHFFFAOYSA-N 2-fluoro-2-methylpentan-3-ol Chemical compound CCC(O)C(C)(C)F LQMAGZIWFASHJM-UHFFFAOYSA-N 0.000 description 2
- VQDNMKWCOYVVJH-UHFFFAOYSA-N 2-fluoro-2-methylpropan-1-ol Chemical compound CC(C)(F)CO VQDNMKWCOYVVJH-UHFFFAOYSA-N 0.000 description 2
- BLYSPQXGKZNMJA-UHFFFAOYSA-N 2-fluorobutan-1-ol Chemical compound CCC(F)CO BLYSPQXGKZNMJA-UHFFFAOYSA-N 0.000 description 2
- SJZQQJOIMGMRKP-UHFFFAOYSA-N 2-fluorodecan-1-ol Chemical compound CCCCCCCCC(F)CO SJZQQJOIMGMRKP-UHFFFAOYSA-N 0.000 description 2
- PYMZAXRFSIFPKK-UHFFFAOYSA-N 2-fluorododecan-1-ol Chemical compound CCCCCCCCCCC(F)CO PYMZAXRFSIFPKK-UHFFFAOYSA-N 0.000 description 2
- PXUHUAWWMDRECM-UHFFFAOYSA-N 2-fluorooctan-1-ol Chemical compound CCCCCCC(F)CO PXUHUAWWMDRECM-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- BFXVQEIWGOVPRX-UHFFFAOYSA-N 2-methyl-1-nitrobutan-2-ol Chemical compound CCC(C)(O)C[N+]([O-])=O BFXVQEIWGOVPRX-UHFFFAOYSA-N 0.000 description 2
- FOOMQHQMUGNBKK-UHFFFAOYSA-N 2-methyl-1-nitropropan-2-ol Chemical compound CC(C)(O)C[N+]([O-])=O FOOMQHQMUGNBKK-UHFFFAOYSA-N 0.000 description 2
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 2
- SEAMRWZKMYUKOI-UHFFFAOYSA-N 2-methyl-2-nitrobutan-1-ol Chemical compound CCC(C)(CO)[N+]([O-])=O SEAMRWZKMYUKOI-UHFFFAOYSA-N 0.000 description 2
- AUTNNBNYALYGCQ-UHFFFAOYSA-N 2-methyl-2-nitrohexan-3-ol Chemical compound CCCC(O)C(C)(C)[N+]([O-])=O AUTNNBNYALYGCQ-UHFFFAOYSA-N 0.000 description 2
- XGIVOZBEDLLCCO-UHFFFAOYSA-N 2-methyl-2-nitropentan-3-ol Chemical compound CCC(O)C(C)(C)[N+]([O-])=O XGIVOZBEDLLCCO-UHFFFAOYSA-N 0.000 description 2
- MVGJRISPEUZYAQ-UHFFFAOYSA-N 2-methyl-2-nitropropan-1-ol Chemical compound OCC(C)(C)[N+]([O-])=O MVGJRISPEUZYAQ-UHFFFAOYSA-N 0.000 description 2
- 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 2
- PQGVSRLIQXRYMV-UHFFFAOYSA-N 2-methyl-3-nitropentan-2-ol Chemical compound CCC([N+]([O-])=O)C(C)(C)O PQGVSRLIQXRYMV-UHFFFAOYSA-N 0.000 description 2
- 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 2
- XYQFGZBXVWWGRK-UHFFFAOYSA-N 2-methyl-4-nitrobutan-2-ol Chemical compound CC(C)(O)CC[N+]([O-])=O XYQFGZBXVWWGRK-UHFFFAOYSA-N 0.000 description 2
- WTRFXBIPCREZQA-UHFFFAOYSA-N 2-methyl-4-nitrohexan-3-ol Chemical compound CCC([N+]([O-])=O)C(O)C(C)C WTRFXBIPCREZQA-UHFFFAOYSA-N 0.000 description 2
- LOCQZPLNYZAZHO-UHFFFAOYSA-N 2-methyl-4-nitropentan-3-ol Chemical compound CC(C)C(O)C(C)[N+]([O-])=O LOCQZPLNYZAZHO-UHFFFAOYSA-N 0.000 description 2
- HGGBYJGRYRWRBE-UHFFFAOYSA-N 2-methyl-5-nitropentan-2-ol Chemical compound CC(C)(O)CCC[N+]([O-])=O HGGBYJGRYRWRBE-UHFFFAOYSA-N 0.000 description 2
- UIKBCINGVAVLOY-UHFFFAOYSA-N 2-nitrododecan-1-ol Chemical compound CCCCCCCCCCC(CO)[N+]([O-])=O UIKBCINGVAVLOY-UHFFFAOYSA-N 0.000 description 2
- BJKHKPOTYLELSH-UHFFFAOYSA-N 2-nitroheptan-3-ol Chemical compound CCCCC(O)C(C)[N+]([O-])=O BJKHKPOTYLELSH-UHFFFAOYSA-N 0.000 description 2
- UCBZLXDOJPRPPV-UHFFFAOYSA-N 2-nitrooctan-1-ol Chemical compound CCCCCCC(CO)[N+]([O-])=O UCBZLXDOJPRPPV-UHFFFAOYSA-N 0.000 description 2
- OYHTVILGINELNJ-UHFFFAOYSA-N 2-nitropentan-1-ol Chemical compound CCCC(CO)[N+]([O-])=O OYHTVILGINELNJ-UHFFFAOYSA-N 0.000 description 2
- UQCZRXRWSNMZEP-UHFFFAOYSA-N 2-nitropentan-3-ol Chemical compound CCC(O)C(C)[N+]([O-])=O UQCZRXRWSNMZEP-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- POPUCNRCMDNMTD-UHFFFAOYSA-N 3,3-dimethyl-1-nitrobutan-2-ol Chemical compound CC(C)(C)C(O)C[N+]([O-])=O POPUCNRCMDNMTD-UHFFFAOYSA-N 0.000 description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- ZISWRXJZUKDIOO-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(CCCO)C=C1OC ZISWRXJZUKDIOO-UHFFFAOYSA-N 0.000 description 2
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
- CFOIQWACFNTMNS-UHFFFAOYSA-N 3-fluoro-2,3-dimethylbutan-2-ol Chemical compound CC(C)(O)C(C)(C)F CFOIQWACFNTMNS-UHFFFAOYSA-N 0.000 description 2
- YSAZHINBXCWZTE-UHFFFAOYSA-N 3-fluorobutan-1-ol Chemical compound CC(F)CCO YSAZHINBXCWZTE-UHFFFAOYSA-N 0.000 description 2
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 2
- VCKPUUFAIGNJHC-UHFFFAOYSA-N 3-hydroxykynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC(O)=C1N VCKPUUFAIGNJHC-UHFFFAOYSA-N 0.000 description 2
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 2
- DMIRKUOHEBAINR-UHFFFAOYSA-N 3-methyl-2-nitrobutan-1-ol Chemical compound CC(C)C(CO)[N+]([O-])=O DMIRKUOHEBAINR-UHFFFAOYSA-N 0.000 description 2
- 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 2
- 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 2
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
- CHOTTWGZEKCPHA-UHFFFAOYSA-N 3-nitro-2-pentanol Chemical compound CCC(C(C)O)[N+]([O-])=O CHOTTWGZEKCPHA-UHFFFAOYSA-N 0.000 description 2
- OJVOGABFNZDOOZ-UHFFFAOYSA-N 3-nitrobutan-2-ol Chemical compound CC(O)C(C)[N+]([O-])=O OJVOGABFNZDOOZ-UHFFFAOYSA-N 0.000 description 2
- CVOIQJVZYQYMBH-UHFFFAOYSA-N 3-nitroheptan-4-ol Chemical compound CCCC(O)C(CC)[N+]([O-])=O CVOIQJVZYQYMBH-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- DUOURUCKSSLFRF-UHFFFAOYSA-N 4-fluoro-4-methylpentan-2-ol Chemical compound CC(O)CC(C)(C)F DUOURUCKSSLFRF-UHFFFAOYSA-N 0.000 description 2
- SHOBGSRUFRALBO-UHFFFAOYSA-N 4-fluorobutan-1-ol Chemical compound OCCCCF SHOBGSRUFRALBO-UHFFFAOYSA-N 0.000 description 2
- PEAJLEGVRQOZNV-UHFFFAOYSA-N 4-fluorobutan-2-ol Chemical compound CC(O)CCF PEAJLEGVRQOZNV-UHFFFAOYSA-N 0.000 description 2
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 2
- DBYMNHYVMTWSLQ-UHFFFAOYSA-N 4-methyl-4-nitropentan-1-ol Chemical compound [O-][N+](=O)C(C)(C)CCCO DBYMNHYVMTWSLQ-UHFFFAOYSA-N 0.000 description 2
- XSOWARLVOQBBOO-UHFFFAOYSA-N 4-nitrobutan-1-ol Chemical compound OCCCC[N+]([O-])=O XSOWARLVOQBBOO-UHFFFAOYSA-N 0.000 description 2
- WYKTYEIIRULHNQ-UHFFFAOYSA-N 4-nitrobutan-2-ol Chemical compound CC(O)CC[N+]([O-])=O WYKTYEIIRULHNQ-UHFFFAOYSA-N 0.000 description 2
- OMUHFGMZLLRVEN-UHFFFAOYSA-N 4-nitroheptan-3-ol Chemical compound CCCC([N+]([O-])=O)C(O)CC OMUHFGMZLLRVEN-UHFFFAOYSA-N 0.000 description 2
- XIXNQTGGBNDDMJ-UHFFFAOYSA-N 4-nitrohexan-3-ol Chemical compound CCC(O)C(CC)[N+]([O-])=O XIXNQTGGBNDDMJ-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 2
- BKAWJIRCKVUVED-UHFFFAOYSA-N 5-(2-hydroxyethyl)-4-methylthiazole Chemical compound CC=1N=CSC=1CCO BKAWJIRCKVUVED-UHFFFAOYSA-N 0.000 description 2
- UEZJJZXNTWFPBP-UHFFFAOYSA-N 5-fluoro-2-methylpentan-2-ol Chemical compound CC(C)(O)CCCF UEZJJZXNTWFPBP-UHFFFAOYSA-N 0.000 description 2
- RCIXPUGUGPXKBZ-UHFFFAOYSA-N 5-fluoropentan-2-ol Chemical compound CC(O)CCCF RCIXPUGUGPXKBZ-UHFFFAOYSA-N 0.000 description 2
- JHAZSFLGWSANGV-UHFFFAOYSA-N 5-methyl-5-nitrohexan-2-ol Chemical compound CC(O)CCC(C)(C)[N+]([O-])=O JHAZSFLGWSANGV-UHFFFAOYSA-N 0.000 description 2
- SEICGYRRALKKBW-UHFFFAOYSA-N 5-nitrooctan-4-ol Chemical compound CCCC(O)C([N+]([O-])=O)CCC SEICGYRRALKKBW-UHFFFAOYSA-N 0.000 description 2
- UISXXYURSRKYST-UHFFFAOYSA-N 5-nitropentan-1-ol Chemical compound OCCCCC[N+]([O-])=O UISXXYURSRKYST-UHFFFAOYSA-N 0.000 description 2
- RITXFFWHWOKLTO-UHFFFAOYSA-N 5-nitropentan-2-ol Chemical compound CC(O)CCC[N+]([O-])=O RITXFFWHWOKLTO-UHFFFAOYSA-N 0.000 description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 2
- JWCOWLWBOYGUPA-UHFFFAOYSA-N 6-fluorohexan-1-ol Chemical compound OCCCCCCF JWCOWLWBOYGUPA-UHFFFAOYSA-N 0.000 description 2
- LIUSQTRCKMJXEP-UHFFFAOYSA-N 6-methyl-6-nitroheptan-2-ol Chemical compound CC(O)CCCC(C)(C)[N+]([O-])=O LIUSQTRCKMJXEP-UHFFFAOYSA-N 0.000 description 2
- SQBSQQUIASSUGB-UHFFFAOYSA-N 6-nitrohexan-1-ol Chemical compound OCCCCCC[N+]([O-])=O SQBSQQUIASSUGB-UHFFFAOYSA-N 0.000 description 2
- BZIZKLZGQRAKFR-UHFFFAOYSA-N 7-fluoroheptan-1-ol Chemical compound OCCCCCCCF BZIZKLZGQRAKFR-UHFFFAOYSA-N 0.000 description 2
- NSQGVCPOJCWINW-UHFFFAOYSA-N 7-nitroheptan-1-ol Chemical compound OCCCCCCC[N+]([O-])=O NSQGVCPOJCWINW-UHFFFAOYSA-N 0.000 description 2
- DGGXBEHZGMUMOU-UHFFFAOYSA-N 8-fluorooctan-1-ol Chemical compound OCCCCCCCCF DGGXBEHZGMUMOU-UHFFFAOYSA-N 0.000 description 2
- NVCMQUWIVFXVRL-UHFFFAOYSA-N 8-nitrooctan-1-ol Chemical compound OCCCCCCCC[N+]([O-])=O NVCMQUWIVFXVRL-UHFFFAOYSA-N 0.000 description 2
- KLHJXURNHSLXLM-UHFFFAOYSA-N 9-fluorononan-1-ol Chemical compound OCCCCCCCCCF KLHJXURNHSLXLM-UHFFFAOYSA-N 0.000 description 2
- SLLKICYJHPXTNM-UHFFFAOYSA-N 9-nitrononan-1-ol Chemical compound OCCCCCCCCC[N+]([O-])=O SLLKICYJHPXTNM-UHFFFAOYSA-N 0.000 description 2
- 102100022749 Aminopeptidase N Human genes 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
- 125000001433 C-terminal amino-acid group Chemical group 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KRCZYMFUWVJCLI-UHFFFAOYSA-N Dihydrocarveol Chemical compound CC1CCC(C(C)=C)CC1O KRCZYMFUWVJCLI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 108010058940 Glutamyl Aminopeptidase Proteins 0.000 description 2
- 102000006485 Glutamyl Aminopeptidase Human genes 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 102000004157 Hydrolases Human genes 0.000 description 2
- 108090000604 Hydrolases Proteins 0.000 description 2
- LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 2
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 125000003047 N-acetyl group Chemical group 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 206010028813 Nausea Diseases 0.000 description 2
- 102000003729 Neprilysin Human genes 0.000 description 2
- 108090000028 Neprilysin Proteins 0.000 description 2
- 229940123424 Neuraminidase inhibitor Drugs 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000003275 alpha amino acid group Chemical group 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 229940059260 amidate Drugs 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 229940125716 antipyretic agent Drugs 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012237 artificial material Substances 0.000 description 2
- 229960001230 asparagine Drugs 0.000 description 2
- 235000009582 asparagine Nutrition 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 description 2
- 150000001541 aziridines Chemical group 0.000 description 2
- 125000004069 aziridinyl group Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 239000012472 biological sample Substances 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 150000005829 chemical entities Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 239000012084 conversion product Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 229940042406 direct acting antivirals neuraminidase inhibitors Drugs 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 239000002662 enteric coated tablet Substances 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 2
- 210000003238 esophagus Anatomy 0.000 description 2
- LUJQXGBDWAGQHS-UHFFFAOYSA-N ethenyl acetate;phthalic acid Chemical compound CC(=O)OC=C.OC(=O)C1=CC=CC=C1C(O)=O LUJQXGBDWAGQHS-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003172 expectorant agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- STJIISDMSMJQQK-UHFFFAOYSA-N furan-3-ylmethanol Chemical compound OCC=1C=COC=1 STJIISDMSMJQQK-UHFFFAOYSA-N 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 229960002743 glutamine Drugs 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 239000001087 glyceryl triacetate Substances 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000007887 hard shell capsule Substances 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 229960002885 histidine Drugs 0.000 description 2
- ZTVZLYBCZNMWCF-UHFFFAOYSA-N homocystine Chemical compound [O-]C(=O)C([NH3+])CCSSCCC([NH3+])C([O-])=O ZTVZLYBCZNMWCF-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 2
- 229960002591 hydroxyproline Drugs 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 238000003018 immunoassay Methods 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 2
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 108010045069 keyhole-limpet hemocyanin Proteins 0.000 description 2
- YGPSJZOEDVAXAB-UHFFFAOYSA-N kynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 2
- 239000011981 lindlar catalyst Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000013563 matrix tablet Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 150000002772 monosaccharides Chemical group 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- BMMXZASTBJBDSZ-UHFFFAOYSA-N n,3-dihydroxybutan-2-imine oxide Chemical compound CC(O)C(C)=[N+](O)[O-] BMMXZASTBJBDSZ-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 230000008693 nausea Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003883 ointment base Substances 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 125000005633 phthalidyl group Chemical group 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920002744 polyvinyl acetate phthalate Polymers 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 229940069328 povidone Drugs 0.000 description 2
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 229960002429 proline Drugs 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 230000001012 protector Effects 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
- 239000007886 soft shell capsule Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000001839 systemic circulation Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VBYPJHLRWKGNAI-UHFFFAOYSA-N tert-butyl aziridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC1 VBYPJHLRWKGNAI-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 2
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
- 229960004441 tyrosine Drugs 0.000 description 2
- 210000002438 upper gastrointestinal tract Anatomy 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 239000004474 valine Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical group N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- WONIGEXYPVIKFS-UHFFFAOYSA-N (+)-cis-Verbenol Natural products CC1=CC(O)C2C(C)(C)C1C2 WONIGEXYPVIKFS-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 description 1
- PIZQWRXTMGASCZ-UHFFFAOYSA-N (1-methylcyclopropyl)methanol Chemical compound OCC1(C)CC1 PIZQWRXTMGASCZ-UHFFFAOYSA-N 0.000 description 1
- HXXJMMLIEYAFOZ-UHFFFAOYSA-N (1-methylpiperidin-2-yl)methanol Chemical compound CN1CCCCC1CO HXXJMMLIEYAFOZ-UHFFFAOYSA-N 0.000 description 1
- UGXQXVDTGJCQHR-UHFFFAOYSA-N (1-methylpiperidin-3-yl)methanol Chemical compound CN1CCCC(CO)C1 UGXQXVDTGJCQHR-UHFFFAOYSA-N 0.000 description 1
- LQYJAVWWKTWWKN-UHFFFAOYSA-N (1-oxidopyridin-1-ium-3-yl)methanol Chemical compound OCC1=CC=C[N+]([O-])=C1 LQYJAVWWKTWWKN-UHFFFAOYSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- BWHYGTUWYAKAGS-MRVPVSSYSA-N (1S)-1-fluorooctan-1-ol Chemical compound F[C@@H](CCCCCCC)O BWHYGTUWYAKAGS-MRVPVSSYSA-N 0.000 description 1
- ZQTYQMYDIHMKQB-DSYKOEDSSA-N (1r,3r,4s)-bicyclo[2.2.1]heptan-3-ol Chemical compound C1C[C@@H]2[C@H](O)C[C@H]1C2 ZQTYQMYDIHMKQB-DSYKOEDSSA-N 0.000 description 1
- NOOLISFMXDJSKH-BBBLOLIVSA-N (1s,2r,5r)-5-methyl-2-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)[C@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-BBBLOLIVSA-N 0.000 description 1
- WONIGEXYPVIKFS-YIZRAAEISA-N (1s,2s,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol Chemical compound CC1=C[C@H](O)[C@@H]2C(C)(C)[C@H]1C2 WONIGEXYPVIKFS-YIZRAAEISA-N 0.000 description 1
- ZQTYQMYDIHMKQB-RRKCRQDMSA-N (1s,3r,4r)-bicyclo[2.2.1]heptan-3-ol Chemical compound C1C[C@H]2[C@H](O)C[C@@H]1C2 ZQTYQMYDIHMKQB-RRKCRQDMSA-N 0.000 description 1
- QEHXDOJPVIHUDO-UHFFFAOYSA-N (2-fluorophenyl)methanol Chemical compound OCC1=CC=CC=C1F QEHXDOJPVIHUDO-UHFFFAOYSA-N 0.000 description 1
- NMGSGTKBIPOQSD-UHFFFAOYSA-N (2-methyl-3-bicyclo[2.2.1]heptanyl)methanol Chemical compound C1CC2C(C)C(CO)C1C2 NMGSGTKBIPOQSD-UHFFFAOYSA-N 0.000 description 1
- SHEINYPABNPRPM-UHFFFAOYSA-N (2-methylcyclopropyl)methanol Chemical compound CC1CC1CO SHEINYPABNPRPM-UHFFFAOYSA-N 0.000 description 1
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- NFAULLMVDVCOQU-SSDOTTSWSA-N (2R)-1-fluoro-2-methylhexan-2-ol Chemical compound CCCC[C@@](C)(O)CF NFAULLMVDVCOQU-SSDOTTSWSA-N 0.000 description 1
- VJCZJBJUAGHLEY-SSDOTTSWSA-N (2R)-1-nitroheptan-2-ol Chemical compound CCCCC[C@@H](O)C[N+]([O-])=O VJCZJBJUAGHLEY-SSDOTTSWSA-N 0.000 description 1
- RITXFFWHWOKLTO-RXMQYKEDSA-N (2R)-5-nitropentan-2-ol Chemical compound C[C@@H](O)CCC[N+]([O-])=O RITXFFWHWOKLTO-RXMQYKEDSA-N 0.000 description 1
- KZTNLLVYRNPCJR-JTQLQIEISA-N (2S)-1-fluorodecan-2-ol Chemical compound CCCCCCCC[C@H](O)CF KZTNLLVYRNPCJR-JTQLQIEISA-N 0.000 description 1
- WRDZSIKOOWXDEE-VIFPVBQESA-N (2S)-1-fluorononan-2-ol Chemical compound CCCCCCC[C@H](O)CF WRDZSIKOOWXDEE-VIFPVBQESA-N 0.000 description 1
- HVFRJUUVTBPXGO-BYPYZUCNSA-N (2S)-2-(7H-purin-2-ylamino)propanoic acid Chemical group C[C@H](Nc1ncc2[nH]cnc2n1)C(O)=O HVFRJUUVTBPXGO-BYPYZUCNSA-N 0.000 description 1
- XJXHGWBUSOZIKC-VIFPVBQESA-N (2S)-2-amino-3-(2-ethoxy-5-nitrophenyl)propanoic acid Chemical group CCOc1ccc(cc1C[C@H](N)C(O)=O)[N+]([O-])=O XJXHGWBUSOZIKC-VIFPVBQESA-N 0.000 description 1
- OKHRYHIXUNLSPK-ZETCQYMHSA-N (2S)-2-fluoro-2-methylhexan-1-ol Chemical compound CCCC[C@](C)(F)CO OKHRYHIXUNLSPK-ZETCQYMHSA-N 0.000 description 1
- BIXPLUJYBHAXHD-RXMQYKEDSA-N (2S)-2-fluoro-3,3-dimethylbutan-1-ol Chemical compound CC(C)(C)[C@H](F)CO BIXPLUJYBHAXHD-RXMQYKEDSA-N 0.000 description 1
- KZTNLLVYRNPCJR-SNVBAGLBSA-N (2r)-1-fluorodecan-2-ol Chemical compound CCCCCCCC[C@@H](O)CF KZTNLLVYRNPCJR-SNVBAGLBSA-N 0.000 description 1
- GRRGZCQZZLXSGF-YFKPBYRVSA-N (2r)-2-fluoro-3-methylbutan-1-ol Chemical compound CC(C)[C@@H](F)CO GRRGZCQZZLXSGF-YFKPBYRVSA-N 0.000 description 1
- ZFNTVJZUVCUSNP-ZCFIWIBFSA-N (2r)-2-fluoro-4-methylpentan-1-ol Chemical compound CC(C)C[C@@H](F)CO ZFNTVJZUVCUSNP-ZCFIWIBFSA-N 0.000 description 1
- LRKCNYYCJZXSHR-SECBINFHSA-N (2r)-2-fluorononan-1-ol Chemical compound CCCCCCC[C@@H](F)CO LRKCNYYCJZXSHR-SECBINFHSA-N 0.000 description 1
- PXUHUAWWMDRECM-MRVPVSSYSA-N (2r)-2-fluorooctan-1-ol Chemical compound CCCCCC[C@@H](F)CO PXUHUAWWMDRECM-MRVPVSSYSA-N 0.000 description 1
- UQCZRXRWSNMZEP-RFZPGFLSSA-N (2r,3r)-2-nitropentan-3-ol Chemical compound CC[C@@H](O)[C@@H](C)[N+]([O-])=O UQCZRXRWSNMZEP-RFZPGFLSSA-N 0.000 description 1
- OJVOGABFNZDOOZ-QWWZWVQMSA-N (2r,3r)-3-nitrobutan-2-ol Chemical compound C[C@@H](O)[C@@H](C)[N+]([O-])=O OJVOGABFNZDOOZ-QWWZWVQMSA-N 0.000 description 1
- CHOTTWGZEKCPHA-RFZPGFLSSA-N (2r,3r)-3-nitropentan-2-ol Chemical compound CC[C@H]([C@@H](C)O)[N+]([O-])=O CHOTTWGZEKCPHA-RFZPGFLSSA-N 0.000 description 1
- OJVOGABFNZDOOZ-IUYQGCFVSA-N (2r,3s)-3-nitrobutan-2-ol Chemical compound C[C@@H](O)[C@H](C)[N+]([O-])=O OJVOGABFNZDOOZ-IUYQGCFVSA-N 0.000 description 1
- CHOTTWGZEKCPHA-UHNVWZDZSA-N (2r,3s)-3-nitropentan-2-ol Chemical compound CC[C@@H]([C@@H](C)O)[N+]([O-])=O CHOTTWGZEKCPHA-UHNVWZDZSA-N 0.000 description 1
- ZVDGZUVHJGGWSG-BKLSDQPFSA-N (2s)-2,5-diamino-4-hydroxypentanoic acid Chemical compound NCC(O)C[C@H](N)C(O)=O ZVDGZUVHJGGWSG-BKLSDQPFSA-N 0.000 description 1
- FJBAOZHBRMLMCP-NSHDSACASA-N (2s)-2-(benzylazaniumyl)-3-methylbutanoate Chemical compound CC(C)[C@@H](C(O)=O)NCC1=CC=CC=C1 FJBAOZHBRMLMCP-NSHDSACASA-N 0.000 description 1
- RLIHXKPTGKETCC-QMMMGPOBSA-N (2s)-2-(benzylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NCC1=CC=CC=C1 RLIHXKPTGKETCC-QMMMGPOBSA-N 0.000 description 1
- IYKLZBIWFXPUCS-VIFPVBQESA-N (2s)-2-(naphthalen-1-ylamino)propanoic acid Chemical compound C1=CC=C2C(N[C@@H](C)C(O)=O)=CC=CC2=C1 IYKLZBIWFXPUCS-VIFPVBQESA-N 0.000 description 1
- CWAYDJFPMMUKOI-YFKPBYRVSA-N (2s)-2-amino-2-methylbutanedioic acid Chemical compound OC(=O)[C@](N)(C)CC(O)=O CWAYDJFPMMUKOI-YFKPBYRVSA-N 0.000 description 1
- CZSQAYAIWDEOSA-QRIDDKLISA-N (2s)-2-amino-3-(1h-indol-3-yl)butanoic acid Chemical compound C1=CC=C2C(C([C@H](N)C(O)=O)C)=CNC2=C1 CZSQAYAIWDEOSA-QRIDDKLISA-N 0.000 description 1
- XAFNUWVLFYOQSL-ZETCQYMHSA-N (2s)-2-amino-3-(2-hydroxy-5-nitrophenyl)propanoic acid Chemical group OC(=O)[C@@H](N)CC1=CC([N+]([O-])=O)=CC=C1O XAFNUWVLFYOQSL-ZETCQYMHSA-N 0.000 description 1
- ONTYPWROJNTIRE-AKGZTFGVSA-N (2s)-2-amino-3-hydroxyhexanoic acid Chemical compound CCCC(O)[C@H](N)C(O)=O ONTYPWROJNTIRE-AKGZTFGVSA-N 0.000 description 1
- LGVJIYCMHMKTPB-BKLSDQPFSA-N (2s)-2-amino-3-hydroxypentanoic acid Chemical compound CCC(O)[C@H](N)C(O)=O LGVJIYCMHMKTPB-BKLSDQPFSA-N 0.000 description 1
- LXRUAYBIUSUULX-NFJMKROFSA-N (2s)-2-amino-3-methylbutanedioic acid Chemical compound OC(=O)C(C)[C@H](N)C(O)=O LXRUAYBIUSUULX-NFJMKROFSA-N 0.000 description 1
- FHJNAFIJPFGZRI-PVPKANODSA-N (2s)-2-amino-3-methylpentanedioic acid Chemical compound OC(=O)CC(C)[C@H](N)C(O)=O FHJNAFIJPFGZRI-PVPKANODSA-N 0.000 description 1
- UXEDFOHTFRNIJS-HTLJXXAVSA-N (2s)-2-amino-3-phenylpentanedioic acid Chemical compound OC(=O)[C@@H](N)C(CC(O)=O)C1=CC=CC=C1 UXEDFOHTFRNIJS-HTLJXXAVSA-N 0.000 description 1
- SBRVJFMQKPUAGQ-BKLSDQPFSA-N (2s)-2-amino-4-hydroxypentanoic acid Chemical compound CC(O)C[C@H](N)C(O)=O SBRVJFMQKPUAGQ-BKLSDQPFSA-N 0.000 description 1
- KLRAETWDWGPFRP-AXDSSHIGSA-N (2s)-2-amino-4-methylsulfanyl-3-phenylbutanoic acid Chemical compound CSCC([C@H](N)C(O)=O)C1=CC=CC=C1 KLRAETWDWGPFRP-AXDSSHIGSA-N 0.000 description 1
- GRRGZCQZZLXSGF-RXMQYKEDSA-N (2s)-2-fluoro-3-methylbutan-1-ol Chemical compound CC(C)[C@H](F)CO GRRGZCQZZLXSGF-RXMQYKEDSA-N 0.000 description 1
- SJZQQJOIMGMRKP-JTQLQIEISA-N (2s)-2-fluorodecan-1-ol Chemical compound CCCCCCCC[C@H](F)CO SJZQQJOIMGMRKP-JTQLQIEISA-N 0.000 description 1
- PYMZAXRFSIFPKK-LBPRGKRZSA-N (2s)-2-fluorododecan-1-ol Chemical compound CCCCCCCCCC[C@H](F)CO PYMZAXRFSIFPKK-LBPRGKRZSA-N 0.000 description 1
- UEBHTEIKXIPNGN-ZETCQYMHSA-N (2s)-2-fluoroheptan-1-ol Chemical compound CCCCC[C@H](F)CO UEBHTEIKXIPNGN-ZETCQYMHSA-N 0.000 description 1
- NVIVQGNQOLBSLT-LURJTMIESA-N (2s)-2-fluorohexan-1-ol Chemical compound CCCC[C@H](F)CO NVIVQGNQOLBSLT-LURJTMIESA-N 0.000 description 1
- LRKCNYYCJZXSHR-VIFPVBQESA-N (2s)-2-fluorononan-1-ol Chemical compound CCCCCCC[C@H](F)CO LRKCNYYCJZXSHR-VIFPVBQESA-N 0.000 description 1
- PXUHUAWWMDRECM-QMMMGPOBSA-N (2s)-2-fluorooctan-1-ol Chemical compound CCCCCC[C@H](F)CO PXUHUAWWMDRECM-QMMMGPOBSA-N 0.000 description 1
- MVFMATZFWFEEKJ-BYPYZUCNSA-N (2s)-3-methyl-3-nitrobutan-2-ol Chemical compound C[C@H](O)C(C)(C)[N+]([O-])=O MVFMATZFWFEEKJ-BYPYZUCNSA-N 0.000 description 1
- RITXFFWHWOKLTO-YFKPBYRVSA-N (2s)-5-nitropentan-2-ol Chemical compound C[C@H](O)CCC[N+]([O-])=O RITXFFWHWOKLTO-YFKPBYRVSA-N 0.000 description 1
- UQCZRXRWSNMZEP-CRCLSJGQSA-N (2s,3r)-2-nitropentan-3-ol Chemical compound CC[C@@H](O)[C@H](C)[N+]([O-])=O UQCZRXRWSNMZEP-CRCLSJGQSA-N 0.000 description 1
- YYLQUHNPNCGKJQ-NHYDCYSISA-N (3R)-3-hydroxy-L-aspartic acid Chemical compound OC(=O)[C@@H](N)[C@@H](O)C(O)=O YYLQUHNPNCGKJQ-NHYDCYSISA-N 0.000 description 1
- DQYNJGWRTSPODI-ZCFIWIBFSA-N (3R)-6-nitrohexan-3-ol Chemical compound CC[C@@H](O)CCC[N+]([O-])=O DQYNJGWRTSPODI-ZCFIWIBFSA-N 0.000 description 1
- BKRMAGHMLGFMJT-YFKPBYRVSA-N (3S)-1-nitropentan-3-ol Chemical compound CC[C@H](O)CC[N+]([O-])=O BKRMAGHMLGFMJT-YFKPBYRVSA-N 0.000 description 1
- FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
- BKRMAGHMLGFMJT-RXMQYKEDSA-N (3r)-1-nitropentan-3-ol Chemical compound CC[C@@H](O)CC[N+]([O-])=O BKRMAGHMLGFMJT-RXMQYKEDSA-N 0.000 description 1
- NOUZIWJKLXBBOH-SSDOTTSWSA-N (3r)-3-fluoroheptan-1-ol Chemical compound CCCC[C@@H](F)CCO NOUZIWJKLXBBOH-SSDOTTSWSA-N 0.000 description 1
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
- NOUZIWJKLXBBOH-ZETCQYMHSA-N (3s)-3-fluoroheptan-1-ol Chemical compound CCCC[C@H](F)CCO NOUZIWJKLXBBOH-ZETCQYMHSA-N 0.000 description 1
- QVKRBXFLYCUYMP-VIFPVBQESA-N (3s)-3-fluorononan-1-ol Chemical compound CCCCCC[C@H](F)CCO QVKRBXFLYCUYMP-VIFPVBQESA-N 0.000 description 1
- DQYNJGWRTSPODI-LURJTMIESA-N (3s)-6-nitrohexan-3-ol Chemical compound CC[C@H](O)CCC[N+]([O-])=O DQYNJGWRTSPODI-LURJTMIESA-N 0.000 description 1
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- DRJIHNSDCCEQLL-QMMMGPOBSA-N (4s)-1-nitrooctan-4-ol Chemical compound CCCC[C@H](O)CCC[N+]([O-])=O DRJIHNSDCCEQLL-QMMMGPOBSA-N 0.000 description 1
- UBHDUFNPQJWPRQ-UHFFFAOYSA-N (5-methyl-1h-imidazol-3-ium-4-yl)methanol;chloride Chemical compound Cl.CC=1NC=NC=1CO UBHDUFNPQJWPRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 1
- UFLHIIWVXFIJGU-ONEGZZNKSA-N (E)-hex-3-en-1-ol Chemical compound CC\C=C\CCO UFLHIIWVXFIJGU-ONEGZZNKSA-N 0.000 description 1
- WRYLYDPHFGVWKC-JTQLQIEISA-N (R)-(-)-p-Menth-1-en-4-ol Natural products CC(C)[C@@]1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-JTQLQIEISA-N 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- MFLYTCSVJYYAOR-UHFFFAOYSA-N (carbamimidoylazaniumyl)formate Chemical compound NC(=N)NC(O)=O MFLYTCSVJYYAOR-UHFFFAOYSA-N 0.000 description 1
- ZOJKRWXDNYZASL-NSCUHMNNSA-N (e)-4-methoxybut-2-enoic acid Chemical compound COC\C=C\C(O)=O ZOJKRWXDNYZASL-NSCUHMNNSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
- YLKHAMLPZAGCGO-UHFFFAOYSA-N 1,1,1-trichloro-3-(4-methoxyphenyl)hepta-2,5-dien-4-one Chemical compound COC1=CC=C(C(=CC(Cl)(Cl)Cl)C(=O)[C-]=CC)C=C1 YLKHAMLPZAGCGO-UHFFFAOYSA-N 0.000 description 1
- XPIJMQVLTXAGME-UHFFFAOYSA-N 1,1-dimethoxycyclohexane Chemical compound COC1(OC)CCCCC1 XPIJMQVLTXAGME-UHFFFAOYSA-N 0.000 description 1
- BDZAWYBXBHTHFM-UHFFFAOYSA-N 1,1-diphenylpropan-2-ol Chemical compound C=1C=CC=CC=1C(C(O)C)C1=CC=CC=C1 BDZAWYBXBHTHFM-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- PVDLUGWWIOGCNH-UHFFFAOYSA-N 1,3-difluoro-2-propanol Chemical compound FCC(O)CF PVDLUGWWIOGCNH-UHFFFAOYSA-N 0.000 description 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 description 1
- ROVATSABYKBNCG-UHFFFAOYSA-N 1-(2-methoxyphenyl)propan-2-ol Chemical compound COC1=CC=CC=C1CC(C)O ROVATSABYKBNCG-UHFFFAOYSA-N 0.000 description 1
- PSDSORRYQPTKSV-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanol Chemical compound CC(O)C1=CC=C(F)C=C1 PSDSORRYQPTKSV-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- FCURFTSXOIATDW-UHFFFAOYSA-N 1-Phenyl-2-pentanol Chemical compound CCCC(O)CC1=CC=CC=C1 FCURFTSXOIATDW-UHFFFAOYSA-N 0.000 description 1
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- BPPZXJZYCOETDA-UHFFFAOYSA-N 1-benzylpiperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC=C1 BPPZXJZYCOETDA-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- LPCWIFPJLFCXRS-UHFFFAOYSA-N 1-ethylcyclopentan-1-ol Chemical compound CCC1(O)CCCC1 LPCWIFPJLFCXRS-UHFFFAOYSA-N 0.000 description 1
- AHOJTPZHHMJMCW-UHFFFAOYSA-N 1-ethylpiperidin-4-ol Chemical compound CCN1CCC(O)CC1 AHOJTPZHHMJMCW-UHFFFAOYSA-N 0.000 description 1
- GJUCEPWSOMEEKT-UHFFFAOYSA-N 1-fluoro-2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(O)CF GJUCEPWSOMEEKT-UHFFFAOYSA-N 0.000 description 1
- KZTNLLVYRNPCJR-UHFFFAOYSA-N 1-fluorodecan-2-ol Chemical compound CCCCCCCCC(O)CF KZTNLLVYRNPCJR-UHFFFAOYSA-N 0.000 description 1
- ANCGAPPEFCPNMP-UHFFFAOYSA-N 1-fluorodecan-5-ol Chemical compound CCCCCC(O)CCCCF ANCGAPPEFCPNMP-UHFFFAOYSA-N 0.000 description 1
- QZGYKAWLZIQCPN-UHFFFAOYSA-N 1-fluorododecan-1-ol Chemical compound CCCCCCCCCCCC(O)F QZGYKAWLZIQCPN-UHFFFAOYSA-N 0.000 description 1
- SIXHNKZQLHNSGP-UHFFFAOYSA-N 1-fluorododecan-2-ol Chemical compound CCCCCCCCCCC(O)CF SIXHNKZQLHNSGP-UHFFFAOYSA-N 0.000 description 1
- RZYULFKPZNCXTB-UHFFFAOYSA-N 1-fluoroheptan-3-ol Chemical compound CCCCC(O)CCF RZYULFKPZNCXTB-UHFFFAOYSA-N 0.000 description 1
- LVOQCSLRNKCYLQ-UHFFFAOYSA-N 1-fluorohexan-3-ol Chemical compound CCCC(O)CCF LVOQCSLRNKCYLQ-UHFFFAOYSA-N 0.000 description 1
- YVRDLTGHVVBLDA-UHFFFAOYSA-N 1-fluorononan-3-ol Chemical compound CCCCCCC(O)CCF YVRDLTGHVVBLDA-UHFFFAOYSA-N 0.000 description 1
- JUXYSVUBIQJRGS-UHFFFAOYSA-N 1-fluoropentan-3-ol Chemical compound CCC(O)CCF JUXYSVUBIQJRGS-UHFFFAOYSA-N 0.000 description 1
- ATPQHBQUXWELOE-UHFFFAOYSA-N 1-hydroxysulfanyl-2,4-dinitrobenzene Chemical compound OSC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O ATPQHBQUXWELOE-UHFFFAOYSA-N 0.000 description 1
- SDTORDSXCYSNTD-UHFFFAOYSA-N 1-methoxy-4-[(4-methoxyphenyl)methoxymethyl]benzene Chemical class C1=CC(OC)=CC=C1COCC1=CC=C(OC)C=C1 SDTORDSXCYSNTD-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- TZGRGOSBCMKZMI-UHFFFAOYSA-N 1-nitrobutan-1-ol Chemical compound CCCC(O)[N+]([O-])=O TZGRGOSBCMKZMI-UHFFFAOYSA-N 0.000 description 1
- NLKHGXNCSZJXRE-UHFFFAOYSA-N 1-nitrodecan-2-ol Chemical compound CCCCCCCCC(O)C[N+]([O-])=O NLKHGXNCSZJXRE-UHFFFAOYSA-N 0.000 description 1
- HFFFAFPPYWBBIR-UHFFFAOYSA-N 1-nitroheptan-4-ol Chemical compound CCCC(O)CCC[N+]([O-])=O HFFFAFPPYWBBIR-UHFFFAOYSA-N 0.000 description 1
- MGGGUUMQEMJSNJ-UHFFFAOYSA-N 1-nitrohexan-2-ol Chemical compound CCCCC(O)C[N+]([O-])=O MGGGUUMQEMJSNJ-UHFFFAOYSA-N 0.000 description 1
- VQBXYLSXCORZGJ-UHFFFAOYSA-N 1-nitrononan-2-ol Chemical compound CCCCCCCC(O)C[N+]([O-])=O VQBXYLSXCORZGJ-UHFFFAOYSA-N 0.000 description 1
- DRJIHNSDCCEQLL-UHFFFAOYSA-N 1-nitrooctan-4-ol Chemical compound CCCCC(O)CCC[N+]([O-])=O DRJIHNSDCCEQLL-UHFFFAOYSA-N 0.000 description 1
- BKRMAGHMLGFMJT-UHFFFAOYSA-N 1-nitropentan-3-ol Chemical compound CCC(O)CC[N+]([O-])=O BKRMAGHMLGFMJT-UHFFFAOYSA-N 0.000 description 1
- WYTRYIUQUDTGSX-UHFFFAOYSA-N 1-phenylpropan-2-ol Chemical compound CC(O)CC1=CC=CC=C1 WYTRYIUQUDTGSX-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VGVSQCOSLXVVHM-UHFFFAOYSA-N 1-tritylaziridine Chemical compound C1CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VGVSQCOSLXVVHM-UHFFFAOYSA-N 0.000 description 1
- OLZUCPDJVBXMFC-UHFFFAOYSA-N 10-fluoro-2-methyldecan-1-ol Chemical compound OCC(C)CCCCCCCCF OLZUCPDJVBXMFC-UHFFFAOYSA-N 0.000 description 1
- ALUAXHOULLAYIV-UHFFFAOYSA-N 11-fluoro-2-methylundecan-2-ol Chemical compound CC(C)(O)CCCCCCCCCF ALUAXHOULLAYIV-UHFFFAOYSA-N 0.000 description 1
- MKJMKQDVRQGWIN-UHFFFAOYSA-N 11-nitroundecan-5-ol Chemical compound CCCCC(O)CCCCCC[N+]([O-])=O MKJMKQDVRQGWIN-UHFFFAOYSA-N 0.000 description 1
- LGEZTMRIZWCDLW-UHFFFAOYSA-N 14-methylpentadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC(C)C LGEZTMRIZWCDLW-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- BLCJBICVQSYOIF-UHFFFAOYSA-N 2,2-diaminobutanoic acid Chemical compound CCC(N)(N)C(O)=O BLCJBICVQSYOIF-UHFFFAOYSA-N 0.000 description 1
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
- FENXWSIHLBOCOU-UHFFFAOYSA-N 2,2-dimethyl-4-nitrononan-3-ol Chemical compound CCCCCC([N+]([O-])=O)C(O)C(C)(C)C FENXWSIHLBOCOU-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- NYLOEXLAXYHOHH-UHFFFAOYSA-N 2,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(CO)C1=CC=CC=C1 NYLOEXLAXYHOHH-UHFFFAOYSA-N 0.000 description 1
- HBOQXIRUPVQLKX-UHFFFAOYSA-N 2,3-di(octadeca-9,12-dienoyloxy)propyl octadeca-9,12-dienoate Chemical compound CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC HBOQXIRUPVQLKX-UHFFFAOYSA-N 0.000 description 1
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
- HKZHQZUAKVJYIZ-UHFFFAOYSA-N 2,3-dimethyl-1-nitrobutan-2-ol Chemical compound CC(C)C(C)(O)C[N+]([O-])=O HKZHQZUAKVJYIZ-UHFFFAOYSA-N 0.000 description 1
- KMUWIXHDMPMULL-UHFFFAOYSA-N 2,3-dimethyl-3-nitrobutan-1-ol Chemical compound OCC(C)C(C)(C)[N+]([O-])=O KMUWIXHDMPMULL-UHFFFAOYSA-N 0.000 description 1
- QAOAMCQLMQIMMW-UHFFFAOYSA-N 2,3-dimethyl-3-nitrobutan-2-ol Chemical compound CC(C)(O)C(C)(C)[N+]([O-])=O QAOAMCQLMQIMMW-UHFFFAOYSA-N 0.000 description 1
- MPERRNLTDKMQTN-UHFFFAOYSA-N 2,4,4-trimethyl-1-nitropentan-2-ol Chemical compound CC(C)(C)CC(C)(O)C[N+]([O-])=O MPERRNLTDKMQTN-UHFFFAOYSA-N 0.000 description 1
- FFFIRKXTFQCCKJ-UHFFFAOYSA-M 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=C(C([O-])=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-M 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- YBRHBMHQQIEOOL-UHFFFAOYSA-N 2,4-dimethylhepta-2,6-dien-1-ol Chemical compound C=CCC(C)C=C(C)CO YBRHBMHQQIEOOL-UHFFFAOYSA-N 0.000 description 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical compound C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 description 1
- FKOHSZUQSFEPKG-UHFFFAOYSA-N 2,5-dimethyl-1-nitrohexan-3-ol Chemical compound CC(C)CC(O)C(C)C[N+]([O-])=O FKOHSZUQSFEPKG-UHFFFAOYSA-N 0.000 description 1
- UHUKFMFXIIXGMX-UHFFFAOYSA-N 2,5-dimethyl-4-nitrohexan-3-ol Chemical compound CC(C)C(O)C(C(C)C)[N+]([O-])=O UHUKFMFXIIXGMX-UHFFFAOYSA-N 0.000 description 1
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
- WUUKSIZJXIORDG-UHFFFAOYSA-N 2,6-dimethyl-6-nitroheptan-2-ol Chemical compound CC(C)(O)CCCC(C)(C)[N+]([O-])=O WUUKSIZJXIORDG-UHFFFAOYSA-N 0.000 description 1
- ZBIDZPHRNBZTLT-UHFFFAOYSA-N 2-(1-adamantyl)ethanol Chemical compound C1C(C2)CC3CC2CC1(CCO)C3 ZBIDZPHRNBZTLT-UHFFFAOYSA-N 0.000 description 1
- PHTPILSMVCRNAS-UHFFFAOYSA-N 2-(1-aminoethyl)-3-methylbutanoic acid Chemical compound CC(C)C(C(C)N)C(O)=O PHTPILSMVCRNAS-UHFFFAOYSA-N 0.000 description 1
- FYVMBPXFPFAECB-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanol Chemical compound CN1CCCC1CCO FYVMBPXFPFAECB-UHFFFAOYSA-N 0.000 description 1
- YURLCYGZYWDCHL-UHFFFAOYSA-N 2-(2,6-dichloro-4-methylphenoxy)acetic acid Chemical compound CC1=CC(Cl)=C(OCC(O)=O)C(Cl)=C1 YURLCYGZYWDCHL-UHFFFAOYSA-N 0.000 description 1
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
- IWNHTCBFRSCBQK-UHFFFAOYSA-N 2-(2-chlorophenyl)ethanol Chemical compound OCCC1=CC=CC=C1Cl IWNHTCBFRSCBQK-UHFFFAOYSA-N 0.000 description 1
- HNIGZVZDWCTFPR-UHFFFAOYSA-N 2-(2-fluorophenyl)ethanol Chemical compound OCCC1=CC=CC=C1F HNIGZVZDWCTFPR-UHFFFAOYSA-N 0.000 description 1
- MWFLUYFYHANMCM-UHFFFAOYSA-N 2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCO)C(=O)C2=C1 MWFLUYFYHANMCM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XLDRDNQLEMMNNH-UHFFFAOYSA-N 2-(2-methoxyphenyl)ethanol Chemical compound COC1=CC=CC=C1CCO XLDRDNQLEMMNNH-UHFFFAOYSA-N 0.000 description 1
- SRQAJMUHZROVHW-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethanol Chemical compound COC1=CC=C(CCO)C=C1OC SRQAJMUHZROVHW-UHFFFAOYSA-N 0.000 description 1
- NDWAVJKRSASRPH-UHFFFAOYSA-N 2-(3-chlorophenyl)ethanol Chemical compound OCCC1=CC=CC(Cl)=C1 NDWAVJKRSASRPH-UHFFFAOYSA-N 0.000 description 1
- UPPGEJSCUZMCMW-UHFFFAOYSA-N 2-(3-methoxyphenyl)ethanol Chemical compound COC1=CC=CC(CCO)=C1 UPPGEJSCUZMCMW-UHFFFAOYSA-N 0.000 description 1
- KWHVBVJDKLSOTB-UHFFFAOYSA-N 2-(3-methylphenyl)ethanol Chemical compound CC1=CC=CC(CCO)=C1 KWHVBVJDKLSOTB-UHFFFAOYSA-N 0.000 description 1
- QYIOGYCRGNHDNK-UHFFFAOYSA-N 2-(4-bromophenoxy)ethanol Chemical compound OCCOC1=CC=C(Br)C=C1 QYIOGYCRGNHDNK-UHFFFAOYSA-N 0.000 description 1
- PMOSJSPFNDUAFY-UHFFFAOYSA-N 2-(4-bromophenyl)ethanol Chemical compound OCCC1=CC=C(Br)C=C1 PMOSJSPFNDUAFY-UHFFFAOYSA-N 0.000 description 1
- KOTCBJVZFVDOCK-UHFFFAOYSA-N 2-(4-chloro-n-methylsulfonylanilino)-n-(4-propan-2-ylphenyl)acetamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)CN(S(C)(=O)=O)C1=CC=C(Cl)C=C1 KOTCBJVZFVDOCK-UHFFFAOYSA-N 0.000 description 1
- HZFRKZWBVUJYDA-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanol Chemical compound OCCC1=CC=C(Cl)C=C1 HZFRKZWBVUJYDA-UHFFFAOYSA-N 0.000 description 1
- XYPMGJKFSRTMFY-UHFFFAOYSA-N 2-(4-ethoxy-3-methoxyphenyl)ethanol Chemical compound CCOC1=CC=C(CCO)C=C1OC XYPMGJKFSRTMFY-UHFFFAOYSA-N 0.000 description 1
- DAVFJRVIVZOKKS-UHFFFAOYSA-N 2-(4-methylphenyl)ethanol Chemical compound CC1=CC=C(CCO)C=C1 DAVFJRVIVZOKKS-UHFFFAOYSA-N 0.000 description 1
- KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 description 1
- PIVJVCRQCUYKNZ-UHFFFAOYSA-N 2-(benzylazaniumyl)-3-phenylpropanoate Chemical compound C=1C=CC=CC=1CNC(C(=O)O)CC1=CC=CC=C1 PIVJVCRQCUYKNZ-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
- XJDGGHYRNCSSGD-UHFFFAOYSA-N 2-(fluoromethyl)-2-methylpentan-1-ol Chemical compound CCCC(C)(CO)CF XJDGGHYRNCSSGD-UHFFFAOYSA-N 0.000 description 1
- FRYOUKNFWFXASU-UHFFFAOYSA-N 2-(methylamino)acetic acid Chemical compound CNCC(O)=O.CNCC(O)=O FRYOUKNFWFXASU-UHFFFAOYSA-N 0.000 description 1
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
- BZAZNULYLRVMSW-UHFFFAOYSA-N 2-Methyl-2-buten-3-ol Natural products CC(C)=C(C)O BZAZNULYLRVMSW-UHFFFAOYSA-N 0.000 description 1
- RNDNSYIPLPAXAZ-UHFFFAOYSA-N 2-Phenyl-1-propanol Chemical compound OCC(C)C1=CC=CC=C1 RNDNSYIPLPAXAZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- QZDDFQLIQRYMBV-UHFFFAOYSA-N 2-[3-nitro-2-(2-nitrophenyl)-4-oxochromen-8-yl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(C=2[N+]([O-])=O)=O)=C1OC=2C1=CC=CC=C1[N+]([O-])=O QZDDFQLIQRYMBV-UHFFFAOYSA-N 0.000 description 1
- CAITYLFVJGDODP-UHFFFAOYSA-N 2-amino-2-butylhexanoic acid Chemical compound CCCCC(N)(C(O)=O)CCCC CAITYLFVJGDODP-UHFFFAOYSA-N 0.000 description 1
- CZHCGMZJLLOYJW-UHFFFAOYSA-N 2-amino-2-propylpentanoic acid Chemical compound CCCC(N)(C(O)=O)CCC CZHCGMZJLLOYJW-UHFFFAOYSA-N 0.000 description 1
- FVNKWWBXNSNIAR-UHFFFAOYSA-N 2-amino-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)propanoic acid Chemical compound OC(=O)C(N)CC1=CNC(S)=N1 FVNKWWBXNSNIAR-UHFFFAOYSA-N 0.000 description 1
- OZTZCRKHTRDKQV-UHFFFAOYSA-N 2-amino-3-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)C(N)C(O)=O OZTZCRKHTRDKQV-UHFFFAOYSA-N 0.000 description 1
- OUBVKSUTYWBLCS-UHFFFAOYSA-N 2-amino-3-methyl-2-propan-2-ylbutanoic acid Chemical compound CC(C)C(N)(C(C)C)C(O)=O OUBVKSUTYWBLCS-UHFFFAOYSA-N 0.000 description 1
- NHHUZNBRAXROKE-UHFFFAOYSA-N 2-amino-4-methyl-2-(2-methylpropyl)pentanoic acid Chemical compound CC(C)CC(N)(C(O)=O)CC(C)C NHHUZNBRAXROKE-UHFFFAOYSA-N 0.000 description 1
- RIXOERQXXDKBPZ-UHFFFAOYSA-N 2-amino-5-hydroxy-2-methylpentanoic acid Chemical compound OC(=O)C(N)(C)CCCO RIXOERQXXDKBPZ-UHFFFAOYSA-N 0.000 description 1
- JUQLUIFNNFIIKC-UHFFFAOYSA-N 2-aminopimelic acid Chemical compound OC(=O)C(N)CCCCC(O)=O JUQLUIFNNFIIKC-UHFFFAOYSA-N 0.000 description 1
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
- WAMWSIDTKSNDCU-UHFFFAOYSA-N 2-azaniumyl-2-cyclohexylacetate Chemical compound OC(=O)C(N)C1CCCCC1 WAMWSIDTKSNDCU-UHFFFAOYSA-N 0.000 description 1
- KWOMLHIFHFWBSB-UHFFFAOYSA-N 2-azaniumyl-2-ethylbutanoate Chemical compound CCC(N)(CC)C(O)=O KWOMLHIFHFWBSB-UHFFFAOYSA-N 0.000 description 1
- ORQXBVXKBGUSBA-UHFFFAOYSA-N 2-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)C(N)CC1CCCCC1 ORQXBVXKBGUSBA-UHFFFAOYSA-N 0.000 description 1
- XHEPANNURIQWRM-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)ethanol Chemical compound ClCC(O)C1=CC=C(Cl)C=C1Cl XHEPANNURIQWRM-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical group CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- XZUFESJDDBOWHJ-UHFFFAOYSA-N 2-ethyl-2-(fluoromethyl)butan-1-ol Chemical compound CCC(CC)(CO)CF XZUFESJDDBOWHJ-UHFFFAOYSA-N 0.000 description 1
- SFAAOBGYWOUHLU-UHFFFAOYSA-N 2-ethylhexyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(CC)CCCC SFAAOBGYWOUHLU-UHFFFAOYSA-N 0.000 description 1
- FNSDYJBAZKKTPR-UHFFFAOYSA-N 2-fluoro-2,3-dimethylbutan-1-ol Chemical compound CC(C)C(C)(F)CO FNSDYJBAZKKTPR-UHFFFAOYSA-N 0.000 description 1
- BFIUZJIVOBAMGC-UHFFFAOYSA-N 2-fluoro-2,5-dimethylnonan-5-ol Chemical compound CCCCC(C)(O)CCC(C)(C)F BFIUZJIVOBAMGC-UHFFFAOYSA-N 0.000 description 1
- YTZUHOYRFWCYAX-UHFFFAOYSA-N 2-fluoro-2,6-dimethylheptan-3-ol Chemical compound CC(C)CCC(O)C(C)(C)F YTZUHOYRFWCYAX-UHFFFAOYSA-N 0.000 description 1
- JTADSDIQROXXJS-UHFFFAOYSA-N 2-fluoro-2-methylbutan-1-ol Chemical compound CCC(C)(F)CO JTADSDIQROXXJS-UHFFFAOYSA-N 0.000 description 1
- UAUZAIOTENQPSA-UHFFFAOYSA-N 2-fluoro-2-methylheptan-1-ol Chemical compound CCCCCC(C)(F)CO UAUZAIOTENQPSA-UHFFFAOYSA-N 0.000 description 1
- KFGKCNVTICEZTA-UHFFFAOYSA-N 2-fluoro-2-methyloctan-1-ol Chemical compound CCCCCCC(C)(F)CO KFGKCNVTICEZTA-UHFFFAOYSA-N 0.000 description 1
- UCLKDKHIDQBUJE-UHFFFAOYSA-N 2-fluoro-2-methylpentan-1-ol Chemical compound CCCC(C)(F)CO UCLKDKHIDQBUJE-UHFFFAOYSA-N 0.000 description 1
- DAHFDQKKODDTCB-UHFFFAOYSA-N 2-fluoro-4-methylheptan-3-ol Chemical compound CCCC(C)C(O)C(C)F DAHFDQKKODDTCB-UHFFFAOYSA-N 0.000 description 1
- ZFNTVJZUVCUSNP-UHFFFAOYSA-N 2-fluoro-4-methylpentan-1-ol Chemical compound CC(C)CC(F)CO ZFNTVJZUVCUSNP-UHFFFAOYSA-N 0.000 description 1
- IZMAVOMSWXQOEU-UHFFFAOYSA-N 2-fluoro-5-methylhexan-1-ol Chemical compound CC(C)CCC(F)CO IZMAVOMSWXQOEU-UHFFFAOYSA-N 0.000 description 1
- MXROEWVKLWYHJD-UHFFFAOYSA-N 2-fluoro-6-methylheptan-1-ol Chemical compound CC(C)CCCC(F)CO MXROEWVKLWYHJD-UHFFFAOYSA-N 0.000 description 1
- UEBHTEIKXIPNGN-UHFFFAOYSA-N 2-fluoroheptan-1-ol Chemical compound CCCCCC(F)CO UEBHTEIKXIPNGN-UHFFFAOYSA-N 0.000 description 1
- NVIVQGNQOLBSLT-UHFFFAOYSA-N 2-fluorohexan-1-ol Chemical compound CCCCC(F)CO NVIVQGNQOLBSLT-UHFFFAOYSA-N 0.000 description 1
- LRKCNYYCJZXSHR-UHFFFAOYSA-N 2-fluorononan-1-ol Chemical compound CCCCCCCC(F)CO LRKCNYYCJZXSHR-UHFFFAOYSA-N 0.000 description 1
- OMAFODCGMXDASL-UHFFFAOYSA-N 2-fluoropentan-1-ol Chemical compound CCCC(F)CO OMAFODCGMXDASL-UHFFFAOYSA-N 0.000 description 1
- GAKWSSRONDZJSX-UHFFFAOYSA-N 2-fluoroundecan-1-ol Chemical compound CCCCCCCCCC(F)CO GAKWSSRONDZJSX-UHFFFAOYSA-N 0.000 description 1
- SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 1
- VAUYGGXCASQWHK-QMMMGPOBSA-N 2-hydroxy-L-tryptophan Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=C(O)NC2=C1 VAUYGGXCASQWHK-QMMMGPOBSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CJNZAXGUTKBIHP-UHFFFAOYSA-M 2-iodobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-M 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- SEJKXTIELBGTBI-UHFFFAOYSA-N 2-methyl-1-nitroheptan-3-ol Chemical compound CCCCC(O)C(C)C[N+]([O-])=O SEJKXTIELBGTBI-UHFFFAOYSA-N 0.000 description 1
- QRZCBWQBMNDFGW-UHFFFAOYSA-N 2-methyl-1-nitrohexan-3-ol Chemical compound CCCC(O)C(C)C[N+]([O-])=O QRZCBWQBMNDFGW-UHFFFAOYSA-N 0.000 description 1
- GOEAVKJNNDQUAO-UHFFFAOYSA-N 2-methyl-1-nitrooctan-3-ol Chemical compound CCCCCC(O)C(C)C[N+]([O-])=O GOEAVKJNNDQUAO-UHFFFAOYSA-N 0.000 description 1
- QDGGABYPSJOCQS-UHFFFAOYSA-N 2-methyl-1-nitropentan-2-ol Chemical compound CCCC(C)(O)C[N+]([O-])=O QDGGABYPSJOCQS-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Substances CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- MHHBWCNPCLJUQT-UHFFFAOYSA-N 2-methyl-2-nitrononan-3-ol Chemical compound CCCCCCC(O)C(C)(C)[N+]([O-])=O MHHBWCNPCLJUQT-UHFFFAOYSA-N 0.000 description 1
- HPHJFUPTSXGPJM-UHFFFAOYSA-N 2-methyl-2-nitroundecan-3-ol Chemical compound CCCCCCCCC(O)C(C)(C)[N+]([O-])=O HPHJFUPTSXGPJM-UHFFFAOYSA-N 0.000 description 1
- NRAHZWWOUFWJGR-UHFFFAOYSA-N 2-methyl-3-nitrobutan-1-ol Chemical compound OCC(C)C(C)[N+]([O-])=O NRAHZWWOUFWJGR-UHFFFAOYSA-N 0.000 description 1
- XOOAQXITNKYJCD-UHFFFAOYSA-N 2-methyl-3-nitrobutan-2-ol Chemical compound [O-][N+](=O)C(C)C(C)(C)O XOOAQXITNKYJCD-UHFFFAOYSA-N 0.000 description 1
- FBVKJVNVZHVMGW-UHFFFAOYSA-N 2-methyl-3-nitropentan-1-ol Chemical compound CCC([N+]([O-])=O)C(C)CO FBVKJVNVZHVMGW-UHFFFAOYSA-N 0.000 description 1
- LJILCIAFGJYJDK-UHFFFAOYSA-N 2-methyl-3-nitropropan-1-ol Chemical compound OCC(C)C[N+]([O-])=O LJILCIAFGJYJDK-UHFFFAOYSA-N 0.000 description 1
- CDUUKBXTEOFITR-BYPYZUCNSA-N 2-methyl-L-serine Chemical compound OC[C@@]([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-BYPYZUCNSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- DXTPFLJTURHQRU-UHFFFAOYSA-N 2-methylbutan-2-yl 2-methoxyacetate Chemical compound CCC(C)(C)OC(=O)COC DXTPFLJTURHQRU-UHFFFAOYSA-N 0.000 description 1
- WBBPRCNXBQTYLF-UHFFFAOYSA-N 2-methylthioethanol Chemical compound CSCCO WBBPRCNXBQTYLF-UHFFFAOYSA-N 0.000 description 1
- RXWNCMHRJCOWDK-UHFFFAOYSA-N 2-naphthalen-1-ylethanol Chemical compound C1=CC=C2C(CCO)=CC=CC2=C1 RXWNCMHRJCOWDK-UHFFFAOYSA-N 0.000 description 1
- VCZANYLMPFRUHG-UHFFFAOYSA-N 2-naphthalen-2-ylethanol Chemical compound C1=CC=CC2=CC(CCO)=CC=C21 VCZANYLMPFRUHG-UHFFFAOYSA-N 0.000 description 1
- MHIHRIPETCJEMQ-UHFFFAOYSA-N 2-nitrobutan-1-ol Chemical compound CCC(CO)[N+]([O-])=O MHIHRIPETCJEMQ-UHFFFAOYSA-N 0.000 description 1
- FSJZGJIIPILZQK-UHFFFAOYSA-N 2-nitrodecan-4-ol Chemical compound CCCCCCC(O)CC(C)[N+]([O-])=O FSJZGJIIPILZQK-UHFFFAOYSA-N 0.000 description 1
- JMWUXGYZNJBRMA-UHFFFAOYSA-N 2-nitrododecan-3-ol Chemical compound CCCCCCCCCC(O)C(C)[N+]([O-])=O JMWUXGYZNJBRMA-UHFFFAOYSA-N 0.000 description 1
- PCFLNKSZNBPQOP-UHFFFAOYSA-N 2-nitrohexan-3-ol Chemical compound CCCC(O)C(C)[N+]([O-])=O PCFLNKSZNBPQOP-UHFFFAOYSA-N 0.000 description 1
- SLKZLAMPKCXMAI-UHFFFAOYSA-N 2-nitrononan-3-ol Chemical compound CCCCCCC(O)C(C)[N+]([O-])=O SLKZLAMPKCXMAI-UHFFFAOYSA-N 0.000 description 1
- PJZKSNPFLKEFHX-UHFFFAOYSA-N 2-nitrooctan-3-ol Chemical compound CCCCCC(O)C(C)[N+]([O-])=O PJZKSNPFLKEFHX-UHFFFAOYSA-N 0.000 description 1
- NCQZFTUKRHTFMX-UHFFFAOYSA-N 2-nitroundecan-3-ol Chemical compound CCCCCCCCC(O)C(C)[N+]([O-])=O NCQZFTUKRHTFMX-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KWWZHCSQVRVQGF-UHFFFAOYSA-N 2-phenylsulfanylethanol Chemical compound OCCSC1=CC=CC=C1 KWWZHCSQVRVQGF-UHFFFAOYSA-N 0.000 description 1
- PTHDBHDZSMGHKF-UHFFFAOYSA-N 2-piperidin-2-ylethanol Chemical compound OCCC1CCCCN1 PTHDBHDZSMGHKF-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- YYPNNBPPDFTQFX-UHFFFAOYSA-N 2-thiophen-3-ylethanol Chemical compound OCCC=1C=CSC=1 YYPNNBPPDFTQFX-UHFFFAOYSA-N 0.000 description 1
- GPVOTFQILZVCFP-UHFFFAOYSA-N 2-trityloxyacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC(=O)O)C1=CC=CC=C1 GPVOTFQILZVCFP-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- PIQXIIHPQBQVTP-UHFFFAOYSA-N 3,3,5,5-tetramethylcyclohexan-1-ol Chemical compound CC1(C)CC(O)CC(C)(C)C1 PIQXIIHPQBQVTP-UHFFFAOYSA-N 0.000 description 1
- CKRVOEVAAZDRMM-UHFFFAOYSA-N 3,3-dimethyl-2-nitrobutan-1-ol Chemical compound CC(C)(C)C(CO)[N+]([O-])=O CKRVOEVAAZDRMM-UHFFFAOYSA-N 0.000 description 1
- IDCXQMVSIIJUEH-UHFFFAOYSA-N 3,3-diphenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(CCO)C1=CC=CC=C1 IDCXQMVSIIJUEH-UHFFFAOYSA-N 0.000 description 1
- ZOHMNVPRSUYGIP-UHFFFAOYSA-N 3,4-dimethyl-1-nitrohexan-2-ol Chemical compound CCC(C)C(C)C(O)C[N+]([O-])=O ZOHMNVPRSUYGIP-UHFFFAOYSA-N 0.000 description 1
- NIIDHUCLROLCBU-UHFFFAOYSA-N 3-(4-methoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(CCCO)C=C1 NIIDHUCLROLCBU-UHFFFAOYSA-N 0.000 description 1
- JKRSQNBRNIYETC-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-ol Chemical compound CN1CCN(CCCO)CC1 JKRSQNBRNIYETC-UHFFFAOYSA-N 0.000 description 1
- SVDVGLLYKJZIIZ-UHFFFAOYSA-N 3-(nitromethyl)heptan-4-ol Chemical compound CCCC(O)C(CC)C[N+]([O-])=O SVDVGLLYKJZIIZ-UHFFFAOYSA-N 0.000 description 1
- YLBJVOGWRMXWET-UHFFFAOYSA-N 3-(nitromethyl)pentan-3-ol Chemical compound CCC(O)(CC)C[N+]([O-])=O YLBJVOGWRMXWET-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- NSPPRYXGGYQMPY-UHFFFAOYSA-N 3-Methylbuten-2-ol-1 Natural products CC(C)C(O)=C NSPPRYXGGYQMPY-UHFFFAOYSA-N 0.000 description 1
- PECYZEOJVXMISF-REOHCLBHSA-N 3-amino-L-alanine Chemical compound [NH3+]C[C@H](N)C([O-])=O PECYZEOJVXMISF-REOHCLBHSA-N 0.000 description 1
- XABCFXXGZPWJQP-UHFFFAOYSA-N 3-aminoadipic acid Chemical compound OC(=O)CC(N)CCC(O)=O XABCFXXGZPWJQP-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- CAZPRAORHCOIHC-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CCl CAZPRAORHCOIHC-UHFFFAOYSA-N 0.000 description 1
- DOANJBQUOFJQHC-UHFFFAOYSA-N 3-chloro-2-(chloromethyl)-2-methylpropan-1-ol Chemical compound OCC(C)(CCl)CCl DOANJBQUOFJQHC-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- IBMXMCXCSPGCDQ-UHFFFAOYSA-N 3-cyclopentylpropan-1-ol Chemical compound OCCCC1CCCC1 IBMXMCXCSPGCDQ-UHFFFAOYSA-N 0.000 description 1
- QQALKLGNPUDVQC-UHFFFAOYSA-N 3-ethyl-2-nitropentan-3-ol Chemical compound CCC(O)(CC)C(C)[N+]([O-])=O QQALKLGNPUDVQC-UHFFFAOYSA-N 0.000 description 1
- FHQGTWJIAUOEEJ-UHFFFAOYSA-N 3-ethyl-4-nitropentan-1-ol Chemical compound OCCC(CC)C(C)[N+]([O-])=O FHQGTWJIAUOEEJ-UHFFFAOYSA-N 0.000 description 1
- KVBBMCNRIZHRMS-UHFFFAOYSA-N 3-fluoro-2-methylbutan-2-ol Chemical compound CC(F)C(C)(C)O KVBBMCNRIZHRMS-UHFFFAOYSA-N 0.000 description 1
- FHKUEBFUICVIIB-UHFFFAOYSA-N 3-fluoro-2-methylpentan-2-ol Chemical compound CCC(F)C(C)(C)O FHKUEBFUICVIIB-UHFFFAOYSA-N 0.000 description 1
- ZLKPVVZVRZPBQM-UHFFFAOYSA-N 3-fluoro-3-methylbutan-2-ol Chemical compound CC(O)C(C)(C)F ZLKPVVZVRZPBQM-UHFFFAOYSA-N 0.000 description 1
- DUVVLMMTTVKUEZ-UHFFFAOYSA-N 3-fluoro-3-methylpentan-1-ol Chemical compound CCC(C)(F)CCO DUVVLMMTTVKUEZ-UHFFFAOYSA-N 0.000 description 1
- QDHRSLFSDGCJFX-UHFFFAOYSA-N 3-fluorobenzyl alcohol Chemical compound OCC1=CC=CC(F)=C1 QDHRSLFSDGCJFX-UHFFFAOYSA-N 0.000 description 1
- KUOMEPXVIPTJJX-UHFFFAOYSA-N 3-fluorobutan-2-ol Chemical compound CC(O)C(C)F KUOMEPXVIPTJJX-UHFFFAOYSA-N 0.000 description 1
- QVKRBXFLYCUYMP-UHFFFAOYSA-N 3-fluorononan-1-ol Chemical compound CCCCCCC(F)CCO QVKRBXFLYCUYMP-UHFFFAOYSA-N 0.000 description 1
- IRHFXWUELYRLLX-UHFFFAOYSA-N 3-fluorononan-2-ol Chemical compound CCCCCCC(F)C(C)O IRHFXWUELYRLLX-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- LKZIEAUIOCGXBY-AOIFVJIMSA-N 3-hydroxy-L-glutamic acid Chemical compound OC(=O)[C@@H](N)C(O)CC(O)=O LKZIEAUIOCGXBY-AOIFVJIMSA-N 0.000 description 1
- ZSJGEQLPOOUWPQ-UHFFFAOYSA-N 3-methyl-1-nitrobutan-1-ol Chemical compound CC(C)CC(O)[N+]([O-])=O ZSJGEQLPOOUWPQ-UHFFFAOYSA-N 0.000 description 1
- BZWWMLNELIGOOV-UHFFFAOYSA-N 3-methyl-3-nitrobutan-1-ol Chemical compound [O-][N+](=O)C(C)(C)CCO BZWWMLNELIGOOV-UHFFFAOYSA-N 0.000 description 1
- IZZUIVNQRYQJNU-UHFFFAOYSA-N 3-methyl-4-nitrobutan-1-ol Chemical compound OCCC(C)C[N+]([O-])=O IZZUIVNQRYQJNU-UHFFFAOYSA-N 0.000 description 1
- RKQUFYHTDOJIOK-UHFFFAOYSA-N 3-methyl-4-nitrobutan-2-ol Chemical compound CC(O)C(C)C[N+]([O-])=O RKQUFYHTDOJIOK-UHFFFAOYSA-N 0.000 description 1
- OYNIAQUIUPRRFP-UHFFFAOYSA-N 3-nitrodecan-4-ol Chemical compound CCCCCCC(O)C(CC)[N+]([O-])=O OYNIAQUIUPRRFP-UHFFFAOYSA-N 0.000 description 1
- ZCXNKFOBXWHRSV-UHFFFAOYSA-N 3-nitrohexan-2-ol Chemical compound CCCC(C(C)O)[N+]([O-])=O ZCXNKFOBXWHRSV-UHFFFAOYSA-N 0.000 description 1
- WLTRWPLDNBAPGP-UHFFFAOYSA-N 3-nitrooctan-2-ol Chemical compound CCCCCC(C(C)O)[N+]([O-])=O WLTRWPLDNBAPGP-UHFFFAOYSA-N 0.000 description 1
- ZRFMODAXLAHRLV-UHFFFAOYSA-N 3-nitropentan-1-ol Chemical compound CCC([N+]([O-])=O)CCO ZRFMODAXLAHRLV-UHFFFAOYSA-N 0.000 description 1
- SQGBBDFDRHDJCJ-UHFFFAOYSA-N 3-phenylbutan-1-ol Chemical compound OCCC(C)C1=CC=CC=C1 SQGBBDFDRHDJCJ-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
- UBARRNXCKBFUEN-UHFFFAOYSA-N 4,5-diphenyl-5h-1,3-oxazol-2-one Chemical compound N=1C(=O)OC(C=2C=CC=CC=2)C=1C1=CC=CC=C1 UBARRNXCKBFUEN-UHFFFAOYSA-N 0.000 description 1
- BZKMQYVECSXZCK-UHFFFAOYSA-N 4,6,6-trimethyl-1-nitroheptan-2-ol Chemical compound CC(C)(C)CC(C)CC(O)C[N+]([O-])=O BZKMQYVECSXZCK-UHFFFAOYSA-N 0.000 description 1
- AJBAYRRIDKXWOE-UHFFFAOYSA-N 4,8-dimethyl-2-nitrononan-1-ol Chemical compound CC(C)CCCC(C)CC(CO)[N+]([O-])=O AJBAYRRIDKXWOE-UHFFFAOYSA-N 0.000 description 1
- CUVGUPIVTLGRGI-UHFFFAOYSA-N 4-(3-phosphonopropyl)piperazine-2-carboxylic acid Chemical compound OC(=O)C1CN(CCCP(O)(O)=O)CCN1 CUVGUPIVTLGRGI-UHFFFAOYSA-N 0.000 description 1
- ONIBHZIXCLTLNO-UHFFFAOYSA-N 4-(4-methoxyphenyl)butan-1-ol Chemical compound COC1=CC=C(CCCCO)C=C1 ONIBHZIXCLTLNO-UHFFFAOYSA-N 0.000 description 1
- MFYJBAQONVFIFC-UHFFFAOYSA-N 4-(4-nitrophenyl)butan-1-ol Chemical compound OCCCCC1=CC=C([N+]([O-])=O)C=C1 MFYJBAQONVFIFC-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- FQPGMQABJNQLLF-UHFFFAOYSA-N 4-aminooxy-2-azaniumylbutanoate Chemical compound NOCCC(N)C(O)=O FQPGMQABJNQLLF-UHFFFAOYSA-N 0.000 description 1
- WAGMYTXJRVPMGW-UHFFFAOYSA-N 4-azidobutanoic acid Chemical compound OC(=O)CCCN=[N+]=[N-] WAGMYTXJRVPMGW-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- NZEBWPHHIQAVOH-UHFFFAOYSA-N 4-cyclohexylbutan-1-ol Chemical compound OCCCCC1CCCCC1 NZEBWPHHIQAVOH-UHFFFAOYSA-N 0.000 description 1
- CBPLISSMCMFSIN-UHFFFAOYSA-N 4-ethyl-2-nitrohexan-3-ol Chemical compound CCC(CC)C(O)C(C)[N+]([O-])=O CBPLISSMCMFSIN-UHFFFAOYSA-N 0.000 description 1
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 1
- XRPIJKJYQDENFB-UHFFFAOYSA-N 4-fluoro-2,2,5,5-tetramethylhexan-3-ol Chemical compound CC(C)(C)C(O)C(F)C(C)(C)C XRPIJKJYQDENFB-UHFFFAOYSA-N 0.000 description 1
- QCLXLDNWWLHSGT-UHFFFAOYSA-N 4-fluoro-3-methylbutan-1-ol Chemical compound FCC(C)CCO QCLXLDNWWLHSGT-UHFFFAOYSA-N 0.000 description 1
- UYJNFDNVJFXENL-UHFFFAOYSA-N 4-fluoro-3-methylpentan-2-ol Chemical compound CC(O)C(C)C(C)F UYJNFDNVJFXENL-UHFFFAOYSA-N 0.000 description 1
- ODBRPUWGTQGUJC-UHFFFAOYSA-N 4-fluorodecan-1-ol Chemical compound CCCCCCC(F)CCCO ODBRPUWGTQGUJC-UHFFFAOYSA-N 0.000 description 1
- JBALFAVSZHYFAI-UHFFFAOYSA-N 4-fluoropentan-2-ol Chemical compound CC(O)CC(C)F JBALFAVSZHYFAI-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- KGUABZAFRKUJIC-UHFFFAOYSA-N 4-hepta-2,4-dien-4-ylpyridine Chemical compound CCC=C(C=CC)C1=CC=NC=C1 KGUABZAFRKUJIC-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- HBDWQSHEVMSFGY-SCQFTWEKSA-N 4-hydroxy-L-glutamic acid Chemical compound OC(=O)[C@@H](N)CC(O)C(O)=O HBDWQSHEVMSFGY-SCQFTWEKSA-N 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- KHKJLJHJTQRHSA-UHFFFAOYSA-N 4-methyl-4-nitropentanoic acid Chemical compound [O-][N+](=O)C(C)(C)CCC(O)=O KHKJLJHJTQRHSA-UHFFFAOYSA-N 0.000 description 1
- RCCMXKJGURLWPB-UHFFFAOYSA-N 4-methyleneglutamic acid Chemical compound OC(=O)C(N)CC(=C)C(O)=O RCCMXKJGURLWPB-UHFFFAOYSA-N 0.000 description 1
- VTVYCMWKOCOBQA-UHFFFAOYSA-N 4-nitrononan-3-ol Chemical compound CCCCCC([N+]([O-])=O)C(O)CC VTVYCMWKOCOBQA-UHFFFAOYSA-N 0.000 description 1
- FLBFJHMJCNKWRH-UHFFFAOYSA-N 4-nitrononan-5-ol Chemical compound CCCCC(O)C([N+]([O-])=O)CCC FLBFJHMJCNKWRH-UHFFFAOYSA-N 0.000 description 1
- JRNRLGRUKBLBRK-UHFFFAOYSA-N 4-nitropentan-1-ol Chemical compound [O-][N+](=O)C(C)CCCO JRNRLGRUKBLBRK-UHFFFAOYSA-N 0.000 description 1
- GTVVZTAFGPQSPC-UHFFFAOYSA-N 4-nitrophenylalanine Chemical compound OC(=O)C(N)CC1=CC=C([N+]([O-])=O)C=C1 GTVVZTAFGPQSPC-UHFFFAOYSA-N 0.000 description 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-M 4-phenylbenzoate Chemical compound C1=CC(C(=O)[O-])=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-M 0.000 description 1
- LDZLXQFDGRCELX-UHFFFAOYSA-N 4-phenylbutan-1-ol Chemical compound OCCCCC1=CC=CC=C1 LDZLXQFDGRCELX-UHFFFAOYSA-N 0.000 description 1
- 125000005986 4-piperidonyl group Chemical group 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- ORKHXTYMCYARRA-UHFFFAOYSA-N 5,5-dimethyl-4-(2-nitroethyl)hexan-1-ol Chemical compound OCCCC(C(C)(C)C)CC[N+]([O-])=O ORKHXTYMCYARRA-UHFFFAOYSA-N 0.000 description 1
- DPZMVZIQRMVBBW-UHFFFAOYSA-N 5-Phenyl-1-pentanol Chemical compound OCCCCCC1=CC=CC=C1 DPZMVZIQRMVBBW-UHFFFAOYSA-N 0.000 description 1
- LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 description 1
- XLHBOQBARWJRAK-UHFFFAOYSA-N 5-fluoro-5-methylhexan-1-ol Chemical compound CC(C)(F)CCCCO XLHBOQBARWJRAK-UHFFFAOYSA-N 0.000 description 1
- XJPCCWCEAMDGKM-UHFFFAOYSA-N 5-fluorohexan-3-ol Chemical compound CCC(O)CC(C)F XJPCCWCEAMDGKM-UHFFFAOYSA-N 0.000 description 1
- FQBZGBYYKHMJFU-UHFFFAOYSA-N 5-fluoropentan-1-ol Chemical compound OCCCCCF FQBZGBYYKHMJFU-UHFFFAOYSA-N 0.000 description 1
- CZWARROQQFCFJB-BYPYZUCNSA-N 5-hydroxy norvaline Chemical compound OC(=O)[C@@H](N)CCCO CZWARROQQFCFJB-BYPYZUCNSA-N 0.000 description 1
- RKEYKDXXZCICFZ-UHFFFAOYSA-N 5-hydroxypipecolic acid Chemical compound OC1CCC(C(O)=O)NC1 RKEYKDXXZCICFZ-UHFFFAOYSA-N 0.000 description 1
- MKVRLWWQPSVRBJ-UHFFFAOYSA-N 5-nitrodecan-2-ol Chemical compound CCCCCC([N+]([O-])=O)CCC(C)O MKVRLWWQPSVRBJ-UHFFFAOYSA-N 0.000 description 1
- OQOFJKJLWUZWHF-UHFFFAOYSA-N 5-nitrohexan-2-ol Chemical compound CC(O)CCC(C)[N+]([O-])=O OQOFJKJLWUZWHF-UHFFFAOYSA-N 0.000 description 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
- HEZIJIXYVAGBBM-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-(2-hydroxybutyl)-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CC(O)CC)N=C1C1=CC=C(Cl)C=C1 HEZIJIXYVAGBBM-UHFFFAOYSA-N 0.000 description 1
- XBBXATPGTYBKKS-UHFFFAOYSA-N 6-fluoro-2,6-dimethylheptan-2-ol Chemical compound CC(C)(O)CCCC(C)(C)F XBBXATPGTYBKKS-UHFFFAOYSA-N 0.000 description 1
- CSALSJNVKGHHCO-UHFFFAOYSA-N 6-fluoro-6-methylheptan-1-ol Chemical compound CC(C)(F)CCCCCO CSALSJNVKGHHCO-UHFFFAOYSA-N 0.000 description 1
- OLUWXTFAPJJWPL-YFKPBYRVSA-N 6-hydroxy-l-norleucine Chemical group OC(=O)[C@@H](N)CCCCO OLUWXTFAPJJWPL-YFKPBYRVSA-N 0.000 description 1
- JEAVIRYCMBDJIU-UHFFFAOYSA-N 6-methyl-1h-pyridin-2-one Chemical compound CC1=CC=CC(O)=N1 JEAVIRYCMBDJIU-UHFFFAOYSA-N 0.000 description 1
- VTARPGIHWUMQPN-UHFFFAOYSA-N 6-nitrohexan-2-ol Chemical compound CC(O)CCCC[N+]([O-])=O VTARPGIHWUMQPN-UHFFFAOYSA-N 0.000 description 1
- DQYNJGWRTSPODI-UHFFFAOYSA-N 6-nitrohexan-3-ol Chemical compound CCC(O)CCC[N+]([O-])=O DQYNJGWRTSPODI-UHFFFAOYSA-N 0.000 description 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 1
- SMEXYHATZFOJJB-UHFFFAOYSA-N 7-fluoroheptan-2-ol Chemical compound CC(O)CCCCCF SMEXYHATZFOJJB-UHFFFAOYSA-N 0.000 description 1
- COQRKPRIDRDOOG-UHFFFAOYSA-N 9-ethylbicyclo[3.3.1]nonan-9-ol Chemical compound C1CCC2CCCC1C2(O)CC COQRKPRIDRDOOG-UHFFFAOYSA-N 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 108010032595 Antibody Binding Sites Proteins 0.000 description 1
- 241000186063 Arthrobacter Species 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- QAOFKYGUSMPWNY-UHFFFAOYSA-N Athidathion Chemical compound CCOP(=S)(OCC)SCN1N=C(OC)SC1=O QAOFKYGUSMPWNY-UHFFFAOYSA-N 0.000 description 1
- 241000711404 Avian avulavirus 1 Species 0.000 description 1
- IADUEWIQBXOCDZ-VKHMYHEASA-N Azetidine-2-carboxylic acid Natural products OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 238000006222 Berchtold homologation reaction Methods 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004358 Butane-1, 3-diol Substances 0.000 description 1
- XYBUDGYYNGYUPX-UHFFFAOYSA-N C(=O)(OC(C)(C)C)N(C(NC(=O)O)=N)C(=O)OC(C)(C)C Chemical compound C(=O)(OC(C)(C)C)N(C(NC(=O)O)=N)C(=O)OC(C)(C)C XYBUDGYYNGYUPX-UHFFFAOYSA-N 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- AXXNGOIFWNTEKL-UHFFFAOYSA-N CC(C)C(CCCC)(O)C[N+](=O)[O-] Chemical compound CC(C)C(CCCC)(O)C[N+](=O)[O-] AXXNGOIFWNTEKL-UHFFFAOYSA-N 0.000 description 1
- ZRVIHIHTDPBEDE-UHFFFAOYSA-N CCOBO Chemical class CCOBO ZRVIHIHTDPBEDE-UHFFFAOYSA-N 0.000 description 1
- 108010049990 CD13 Antigens Proteins 0.000 description 1
- 108010055167 CD59 Antigens Proteins 0.000 description 1
- 102100022002 CD59 glycoprotein Human genes 0.000 description 1
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
- PQRFZVPEJNZXRT-UHFFFAOYSA-N Cannabin Natural products C=1C(OC)=CC(O)=C(C(C=2OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=O)C=1OC=2C1=CC=CC=C1 PQRFZVPEJNZXRT-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- 241000193468 Clostridium perfringens Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- YPWSLBHSMIKTPR-UHFFFAOYSA-N Cystathionine Natural products OC(=O)C(N)CCSSCC(N)C(O)=O YPWSLBHSMIKTPR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 150000008574 D-amino acids Chemical class 0.000 description 1
- ILRYLPWNYFXEMH-UHFFFAOYSA-N D-cystathionine Natural products OC(=O)C(N)CCSCC(N)C(O)=O ILRYLPWNYFXEMH-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 206010017943 Gastrointestinal conditions Diseases 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 1
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 1
- OWXMKDGYPWMGEB-UHFFFAOYSA-N HEPPS Chemical compound OCCN1CCN(CCCS(O)(=O)=O)CC1 OWXMKDGYPWMGEB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- AGPKZVBTJJNPAG-UHNVWZDZSA-N L-allo-Isoleucine Chemical compound CC[C@@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-UHNVWZDZSA-N 0.000 description 1
- CWAYDJFPMMUKOI-UHFFFAOYSA-N L-alpha-methylaspartic acid Natural products OC(=O)C(N)(C)CC(O)=O CWAYDJFPMMUKOI-UHFFFAOYSA-N 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
- ILRYLPWNYFXEMH-WHFBIAKZSA-N L-cystathionine Chemical compound [O-]C(=O)[C@@H]([NH3+])CCSC[C@H]([NH3+])C([O-])=O ILRYLPWNYFXEMH-WHFBIAKZSA-N 0.000 description 1
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 description 1
- XIGSAGMEBXLVJJ-YFKPBYRVSA-N L-homocitrulline Chemical compound NC(=O)NCCCC[C@H]([NH3+])C([O-])=O XIGSAGMEBXLVJJ-YFKPBYRVSA-N 0.000 description 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 1
- 125000000510 L-tryptophano group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[C@@]([H])(C(O[H])=O)N([H])[*])C2=C1[H] 0.000 description 1
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910013684 LiClO 4 Inorganic materials 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 108030004467 Membrane alanyl aminopeptidases Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 description 1
- 241000711386 Mumps virus Species 0.000 description 1
- 241000711408 Murine respirovirus Species 0.000 description 1
- 241000872931 Myoporum sandwicense Species 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- SCIFESDRCALIIM-UHFFFAOYSA-N N-Me-Phenylalanine Natural products CNC(C(O)=O)CC1=CC=CC=C1 SCIFESDRCALIIM-UHFFFAOYSA-N 0.000 description 1
- 229910014299 N-Si Inorganic materials 0.000 description 1
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
- AXDLCFOOGCNDST-UHFFFAOYSA-N N-methyl-DL-tyrosine Natural products CNC(C(O)=O)CC1=CC=C(O)C=C1 AXDLCFOOGCNDST-UHFFFAOYSA-N 0.000 description 1
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 1
- SCIFESDRCALIIM-VIFPVBQESA-N N-methyl-L-phenylalanine Chemical compound C[NH2+][C@H](C([O-])=O)CC1=CC=CC=C1 SCIFESDRCALIIM-VIFPVBQESA-N 0.000 description 1
- AKCRVYNORCOYQT-YFKPBYRVSA-N N-methyl-L-valine Chemical compound CN[C@@H](C(C)C)C(O)=O AKCRVYNORCOYQT-YFKPBYRVSA-N 0.000 description 1
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- RPUGMEHVUNTNCN-UHFFFAOYSA-N NN=CS(=O)(=O)O.C(=O)(OC(C)(C)C)NC(NC(=O)OC(C)(C)C)=S Chemical compound NN=CS(=O)(=O)O.C(=O)(OC(C)(C)C)NC(NC(=O)OC(C)(C)C)=S RPUGMEHVUNTNCN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- BZQFBWGGLXLEPQ-UHFFFAOYSA-N O-phosphoryl-L-serine Natural products OC(=O)C(N)COP(O)(O)=O BZQFBWGGLXLEPQ-UHFFFAOYSA-N 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101150058514 PTGES gene Proteins 0.000 description 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 102000015731 Peptide Hormones Human genes 0.000 description 1
- 108010038988 Peptide Hormones Proteins 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 241000283216 Phocidae Species 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 101100055332 Pseudomonas oleovorans alkN gene Proteins 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- XUHLIQGRKRUKPH-UHFFFAOYSA-N S-allyl-L-cysteine sulfoxide Natural products OC(=O)C(N)CS(=O)CC=C XUHLIQGRKRUKPH-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
- 102100028755 Sialidase-2 Human genes 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 108010034949 Thyroglobulin Proteins 0.000 description 1
- 102000009843 Thyroglobulin Human genes 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 101710162629 Trypsin inhibitor Proteins 0.000 description 1
- 229940122618 Trypsin inhibitor Drugs 0.000 description 1
- 241000607626 Vibrio cholerae Species 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- HVVNJUAVDAZWCB-YFKPBYRVSA-N [(2s)-pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1 HVVNJUAVDAZWCB-YFKPBYRVSA-N 0.000 description 1
- NTCJMVHDZUBYNA-QWRGUYRKSA-N [(4s,5s)-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol Chemical compound O1C(C)=N[C@@H](CO)[C@@H]1C1=CC=CC=C1 NTCJMVHDZUBYNA-QWRGUYRKSA-N 0.000 description 1
- JPVGEFSYKNYYAU-UHFFFAOYSA-N [1-(4-chlorophenyl)cyclopentyl]methanol Chemical compound C=1C=C(Cl)C=CC=1C1(CO)CCCC1 JPVGEFSYKNYYAU-UHFFFAOYSA-N 0.000 description 1
- MZILPZDBVFUXMY-UHFFFAOYSA-N [O-][N+]([S])=O Chemical compound [O-][N+]([S])=O MZILPZDBVFUXMY-UHFFFAOYSA-N 0.000 description 1
- WTZQFPAVRAJTMQ-UHFFFAOYSA-N [O]CC(O)CO Chemical compound [O]CC(O)CO WTZQFPAVRAJTMQ-UHFFFAOYSA-N 0.000 description 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
- 231100000230 acceptable toxicity Toxicity 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 description 1
- 150000004075 acetic anhydrides Chemical class 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- FOWDOWQYRZXQDP-UHFFFAOYSA-N adamantan-2-ol Chemical compound C1C(C2)CC3CC1C(O)C2C3 FOWDOWQYRZXQDP-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003732 agents acting on the eye Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 150000001345 alkine derivatives Chemical group 0.000 description 1
- 125000004848 alkoxyethyl group Chemical group 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005275 alkylenearyl group Chemical group 0.000 description 1
- XUHLIQGRKRUKPH-DYEAUMGKSA-N alliin Chemical compound OC(=O)[C@@H](N)C[S@@](=O)CC=C XUHLIQGRKRUKPH-DYEAUMGKSA-N 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- WNNNWFKQCKFSDK-UHFFFAOYSA-N allylglycine Chemical compound OC(=O)C(N)CC=C WNNNWFKQCKFSDK-UHFFFAOYSA-N 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- CDUUKBXTEOFITR-UHFFFAOYSA-N alpha-methylserine Natural products OCC([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- 230000002862 amidating effect Effects 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000010976 amide bond formation reaction Methods 0.000 description 1
- 125000006242 amine protecting group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 210000001557 animal structure Anatomy 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- OIRYSNYGVAJFEF-UHFFFAOYSA-N azanium;sodium;azide;chloride Chemical compound [NH4+].[Na+].[Cl-].[N-]=[N+]=[N-] OIRYSNYGVAJFEF-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- UGUUDTWORXNLAK-UHFFFAOYSA-N azidoalcohol Chemical compound ON=[N+]=[N-] UGUUDTWORXNLAK-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000013142 basic testing Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- LSNKBVFMXFAUOF-UHFFFAOYSA-N benzyl methanimidate;hydrochloride Chemical compound Cl.N=COCC1=CC=CC=C1 LSNKBVFMXFAUOF-UHFFFAOYSA-N 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- KVPFKMBYCSISTN-UHFFFAOYSA-N benzylsulfanylformic acid Chemical compound OC(=O)SCC1=CC=CC=C1 KVPFKMBYCSISTN-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- CZSQAYAIWDEOSA-UHFFFAOYSA-N beta-Methyltryptophan Natural products C1=CC=C2C(C(C(N)C(O)=O)C)=CNC2=C1 CZSQAYAIWDEOSA-UHFFFAOYSA-N 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- ZAYJDMWJYCTABM-UHFFFAOYSA-N beta-hydroxy leucine Natural products CC(C)C(O)C(N)C(O)=O ZAYJDMWJYCTABM-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- OORRQYZWSVJKSO-UHFFFAOYSA-N bicyclo[4.4.1]undeca-1,3,5,7,9-pentaene Chemical compound C1=CC=C(C2)C=CC=CC2=C1 OORRQYZWSVJKSO-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 102000023732 binding proteins Human genes 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- VYGAQHDGEYQIJU-UHFFFAOYSA-N butanedioic acid;phthalic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O VYGAQHDGEYQIJU-UHFFFAOYSA-N 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000006243 carbonyl protecting group Chemical group 0.000 description 1
- 108010054847 carboxypeptidase P Proteins 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- NFCRBQADEGXVDL-UHFFFAOYSA-M cetylpyridinium chloride monohydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NFCRBQADEGXVDL-UHFFFAOYSA-M 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000012539 chromatography resin Substances 0.000 description 1
- 229960002173 citrulline Drugs 0.000 description 1
- 235000013477 citrulline Nutrition 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 229920001688 coating polymer Polymers 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940126179 compound 72 Drugs 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000004966 cyanoalkyl group Chemical class 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- WPOPOPFNZYPKAV-UHFFFAOYSA-N cyclobutylmethanol Chemical compound OCC1CCC1 WPOPOPFNZYPKAV-UHFFFAOYSA-N 0.000 description 1
- BMCQFFXPECPDPS-UHFFFAOYSA-N cycloheptylmethanol Chemical compound OCC1CCCCCC1 BMCQFFXPECPDPS-UHFFFAOYSA-N 0.000 description 1
- VEIYJWQZNGASMA-UHFFFAOYSA-N cyclohex-3-en-1-ylmethanol Chemical compound OCC1CCC=CC1 VEIYJWQZNGASMA-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 231100000223 dermal penetration Toxicity 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229950006137 dexfosfoserine Drugs 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229940099371 diacetylated monoglycerides Drugs 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229940120124 dichloroacetate Drugs 0.000 description 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
- DAKIDYQCFJQMDF-UHFFFAOYSA-N dichloromethane;pyridine Chemical compound ClCCl.C1=CC=NC=C1 DAKIDYQCFJQMDF-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 229930007024 dihydrocarveol Natural products 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000008387 emulsifying waxe Substances 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 description 1
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 229940066493 expectorants Drugs 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- QEWYKACRFQMRMB-UHFFFAOYSA-M fluoroacetate Chemical compound [O-]C(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-M 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- VTIODUHBZHNXFP-UHFFFAOYSA-N hex-4-en-1-ol Chemical compound CC=CCCCO VTIODUHBZHNXFP-UHFFFAOYSA-N 0.000 description 1
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WFNASTYGEKUMIY-UHFFFAOYSA-N hydron;1h-imidazol-5-ylmethanol;chloride Chemical compound Cl.OCC1=CN=CN1 WFNASTYGEKUMIY-UHFFFAOYSA-N 0.000 description 1
- VLECDMDGMKPUSK-UHFFFAOYSA-N hydron;piperidin-3-ol;chloride Chemical compound Cl.OC1CCCNC1 VLECDMDGMKPUSK-UHFFFAOYSA-N 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012750 in vivo screening Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000004926 indolenyl group Chemical group 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 208000037798 influenza B Diseases 0.000 description 1
- 229940042040 innovative drug Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000012500 ion exchange media Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000004936 isatinoyl group Chemical group N1(C(=O)C(=O)C2=CC=CC=C12)C(=O)* 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 229940078545 isocetyl stearate Drugs 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- GCHPUFAZSONQIV-UHFFFAOYSA-N isovaline Chemical compound CCC(C)(N)C(O)=O GCHPUFAZSONQIV-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
- 239000006101 laboratory sample Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N lauric acid triglyceride Natural products CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- PKAUVIXBZJUYRV-UHFFFAOYSA-N methane;hydroiodide Chemical compound C.I PKAUVIXBZJUYRV-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 1
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 1
- IWVKTOUOPHGZRX-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(=O)C(C)=C IWVKTOUOPHGZRX-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- IQSHMXAZFHORGY-UHFFFAOYSA-N methyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound COC(=O)C=C.CC(=C)C(O)=O IQSHMXAZFHORGY-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- NYEBKUUITGFJAK-UHFFFAOYSA-N methylsulfanylmethanethioic s-acid Chemical compound CSC(O)=S NYEBKUUITGFJAK-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940066491 mucolytics Drugs 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- FZZAGYRGHJYDQH-UHFFFAOYSA-N n,1-dihydroxybutan-2-imine oxide Chemical compound CCC(CO)=[N+](O)[O-] FZZAGYRGHJYDQH-UHFFFAOYSA-N 0.000 description 1
- QPGAAVAFQMNFMS-UHFFFAOYSA-N n,2-dihydroxy-2-methylbutan-1-imine oxide Chemical compound CCC(C)(O)C=[N+](O)[O-] QPGAAVAFQMNFMS-UHFFFAOYSA-N 0.000 description 1
- SNDVBBOFNOWENM-UHFFFAOYSA-N n,2-dihydroxybutan-1-imine oxide Chemical compound CCC(O)C=[N+](O)[O-] SNDVBBOFNOWENM-UHFFFAOYSA-N 0.000 description 1
- LHEGUAPKCRQFSV-UHFFFAOYSA-N n,3-dihydroxy-3-methylbutan-2-imine oxide Chemical compound O[N+]([O-])=C(C)C(C)(C)O LHEGUAPKCRQFSV-UHFFFAOYSA-N 0.000 description 1
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- 229940099459 n-acetylmethionine Drugs 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- CBKFHSNATJJWQK-UHFFFAOYSA-N n-pyridin-3-ylformamide Chemical compound O=CNC1=CC=CN=C1 CBKFHSNATJJWQK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940023490 ophthalmic product Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 102000013415 peroxidase activity proteins Human genes 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000008249 pharmaceutical aerosol Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- DKTXXUNXVCHYDO-UHFFFAOYSA-N phenoxyborinic acid Chemical class OBOC1=CC=CC=C1 DKTXXUNXVCHYDO-UHFFFAOYSA-N 0.000 description 1
- WJCXADMLESSGRI-UHFFFAOYSA-N phenyl selenohypochlorite Chemical compound Cl[Se]C1=CC=CC=C1 WJCXADMLESSGRI-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 150000002993 phenylalanine derivatives Chemical class 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 1
- USRGIUJOYOXOQJ-GBXIJSLDSA-N phosphothreonine Chemical compound OP(=O)(O)O[C@H](C)[C@H](N)C(O)=O USRGIUJOYOXOQJ-GBXIJSLDSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- PRAYXGYYVXRDDW-UHFFFAOYSA-N piperidin-2-ylmethanol Chemical compound OCC1CCCCN1 PRAYXGYYVXRDDW-UHFFFAOYSA-N 0.000 description 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 238000002962 plaque-reduction assay Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 235000004252 protein component Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- UCQFSGCWHRTMGG-UHFFFAOYSA-N pyrazole-1-carboximidamide Chemical compound NC(=N)N1C=CC=N1 UCQFSGCWHRTMGG-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229960000888 rimantadine Drugs 0.000 description 1
- LOFZYSZWOLKUGE-UHFFFAOYSA-N s-benzyl carbamothioate Chemical compound NC(=O)SCC1=CC=CC=C1 LOFZYSZWOLKUGE-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RDZTWEVXRGYCFV-UHFFFAOYSA-M sodium 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonate Chemical compound [Na+].OCCN1CCN(CCS([O-])(=O)=O)CC1 RDZTWEVXRGYCFV-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Chemical compound CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 210000001138 tear Anatomy 0.000 description 1
- VFZKYGKYPMJELO-UHFFFAOYSA-N tert-butyl 2,3,4-trihydroxybutanoate Chemical compound CC(C)(C)OC(=O)C(O)C(O)CO VFZKYGKYPMJELO-UHFFFAOYSA-N 0.000 description 1
- CSOJECDGWHHWRS-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylcarbamothioyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(=S)NC(=O)OC(C)(C)C CSOJECDGWHHWRS-UHFFFAOYSA-N 0.000 description 1
- QFNFDHNZVTWZED-UHFFFAOYSA-N tert-butyl n-[[(2-methylpropan-2-yl)oxycarbonylamino]-pyrazol-1-ylmethylidene]carbamate Chemical compound CC(C)(C)OC(=O)NC(=NC(=O)OC(C)(C)C)N1C=CC=N1 QFNFDHNZVTWZED-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- NPDBDJFLKKQMCM-UHFFFAOYSA-N tert-butylglycine Chemical compound CC(C)(C)C(N)C(O)=O NPDBDJFLKKQMCM-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960002175 thyroglobulin Drugs 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 125000001701 trimethoxybenzyl group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004148 unit process Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- ZAYJDMWJYCTABM-WHFBIAKZSA-N β-hydroxyleucine Chemical compound CC(C)[C@H](O)[C@H](N)C(O)=O ZAYJDMWJYCTABM-WHFBIAKZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/62—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5930897P | 1997-09-17 | 1997-09-17 | |
US93864497A | 1997-09-26 | 1997-09-26 | |
US6019597P | 1997-09-26 | 1997-09-26 | |
US60/059,308 | 1997-09-26 | ||
US60/060,195 | 1997-09-26 | ||
US08/938,644 | 1997-09-26 | ||
PCT/US1998/019355 WO1999014185A1 (en) | 1997-09-17 | 1998-09-15 | Compounds containing six-membered rings, processes for their preparation, and their use as medicaments |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20010024123A true KR20010024123A (ko) | 2001-03-26 |
Family
ID=27369627
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020007002880A Ceased KR20010024123A (ko) | 1997-09-17 | 1998-09-15 | 6-원 고리를 갖는 화합물, 그의 제조 방법 및의약물로서의 용도 |
Country Status (15)
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SI1040094T1 (sl) * | 1997-12-17 | 2009-10-31 | Biocryst Pharm Inc | Substituirane ciklopentanske in ciklopentenske spojine, uporabne kot inhibitorji nevraminidaze |
US6518305B1 (en) | 1998-04-23 | 2003-02-11 | Abbott Laboratories | Five-membered carbocyclic and heterocyclic inhibitors of neuraminidases |
US6455571B1 (en) | 1998-04-23 | 2002-09-24 | Abbott Laboratories | Inhibitors of neuraminidases |
EP1059283B1 (en) * | 1999-06-11 | 2003-05-28 | F. Hoffmann-La Roche Ag | Process for preparing neuraminidase inhibitor ro-64-0796 |
WO2001028981A1 (en) * | 1999-10-19 | 2001-04-26 | Abbott Laboratories | 1-cyclohexene-1-carboxylic acid and 1-cyclohexene-1-carboxylates as neuraminidase inhibitors |
US6593314B1 (en) | 1999-10-19 | 2003-07-15 | Abbott Laboratories | Neuraminidase inhibitors |
JP2001131144A (ja) * | 1999-11-02 | 2001-05-15 | Sagami Chem Res Center | 7−アザビシクロ[4.1.0]ヘプト−3−エン−3−カルボン酸エステル類の製造方法 |
US6403824B2 (en) * | 2000-02-22 | 2002-06-11 | Hoffmann-La Roche Inc. | Process for the preparation for 4,5-diamino shikimic acid derivatives |
AU2001252578A1 (en) * | 2000-04-25 | 2001-11-07 | Sankyo Company Limited | Preventives for influenza |
WO2002092555A1 (fr) * | 2001-05-11 | 2002-11-21 | Sankyo Company, Limited | Derives d'acides sialiques |
US7122684B2 (en) | 2003-03-13 | 2006-10-17 | Roche Colorado Corporation | Process for preparing 1,2-diamino compounds |
BRPI0620737A2 (pt) | 2005-12-28 | 2011-11-22 | Hoffmann La Roche | intermediário de epóxido na sìntese do tamiflu |
US8334319B2 (en) * | 2008-01-04 | 2012-12-18 | Roche Palo Alto Llc | Polymorphic forms of oseltamivir phosphate |
EP2499201B1 (en) * | 2009-11-11 | 2017-05-10 | 3M Innovative Properties Company | Polymeric compositions and method of making and articles thereof |
DE102011117128A1 (de) | 2011-10-28 | 2013-05-02 | Christian-Albrechts-Universität Zu Kiel | Verbindungen zur Therapie der Influenza |
RU2469020C1 (ru) * | 2011-11-08 | 2012-12-10 | Александр Васильевич Иващенко | (3r,4r,5s)-5-амино-4-ациламино-3-(1-этил-пропокси)-циклогекс-1-ен-карбоновые кислоты, их эфиры и способ применения |
CN102659615B (zh) * | 2012-05-09 | 2014-05-07 | 中国药科大学 | 奥司他韦衍生物、其制备方法及其医药用途 |
RU2520836C1 (ru) * | 2013-02-27 | 2014-06-27 | Александр Васильевич Иващенко | (3r,4r,5s)-4-амино-5-(2,2-дифторацетиламино)-3-(1-этилпропокси)-циклогекс-1-енкарбоновая кислота и ее эфиры, способ их получения и применения |
RU2633085C2 (ru) * | 2014-05-20 | 2017-10-11 | Российская Федерация, от имени которой выступает Федеральное государственное казенное учреждение "Войсковая часть 68240" | Противовирусное лекарственное средство в виде капсул и способ его получения |
CN105439884A (zh) * | 2015-10-27 | 2016-03-30 | 沈阳药科大学 | 一种奥司他韦的制备方法 |
CN108047076B (zh) * | 2017-12-26 | 2020-05-08 | 杭州新博思生物医药有限公司 | 一种奥司他韦对映异构体的制备方法 |
CN110194728B (zh) * | 2019-06-19 | 2021-04-30 | 湖南华腾制药有限公司 | 磷酸奥司他韦中间体的连续化合成方法 |
CN114057599A (zh) * | 2020-07-29 | 2022-02-18 | 广州市恒诺康医药科技有限公司 | 神经氨酸酶抑制剂类化合物、其药物组合物及其用途 |
CN116375595A (zh) * | 2023-03-31 | 2023-07-04 | 重庆医药高等专科学校 | 一种磷酸奥司他韦的制备方法及精制方法 |
CN117105801A (zh) * | 2023-07-24 | 2023-11-24 | 四川青木制药有限公司 | 一种奥司他韦及其磷酸盐的制备方法及其中间体 |
CN116666669B (zh) * | 2023-07-25 | 2023-10-03 | 四川大学 | VN负载的Ir团簇及其制备方法与其在催化剂中的用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AP249A (en) * | 1990-04-24 | 1993-03-17 | Biota Scient Management Pty Ltd | Anti-viral compounds. |
WO1992006691A1 (en) * | 1990-10-19 | 1992-04-30 | Biota Scientific Management Pty. Ltd. | Anti-viral compounds that bind the active site of influenza neuramidase and display in vivo activity against orthomyxovirus and paramyxovirus |
SI9620042A (sl) * | 1995-02-27 | 1998-12-31 | Gilead Sciences, Inc. | Novi selektivni inhibitorji virusnih ali bakterijskih neuraminidaz |
US5763483A (en) * | 1995-12-29 | 1998-06-09 | Gilead Sciences, Inc. | Carbocyclic compounds |
ATE215062T1 (de) * | 1996-08-23 | 2002-04-15 | Gilead Sciences Inc | Verfahren zur herstellung von cyclohexen- carboxylatderivate |
-
1998
- 1998-09-15 EP EP98949356A patent/EP1015417A1/en not_active Ceased
- 1998-09-15 JP JP2000511738A patent/JP2001516739A/ja not_active Withdrawn
- 1998-09-15 BR BR9812649-0A patent/BR9812649A/pt not_active Application Discontinuation
- 1998-09-15 NZ NZ502988A patent/NZ502988A/xx not_active IP Right Cessation
- 1998-09-15 CA CA002303323A patent/CA2303323A1/en not_active Abandoned
- 1998-09-15 ID IDW20000543A patent/ID25516A/id unknown
- 1998-09-15 CN CN98809320A patent/CN1272105A/zh active Pending
- 1998-09-15 AU AU95694/98A patent/AU747702B2/en not_active Expired
- 1998-09-15 KR KR1020007002880A patent/KR20010024123A/ko not_active Ceased
- 1998-09-15 WO PCT/US1998/019355 patent/WO1999014185A1/en not_active Application Discontinuation
- 1998-09-15 TR TR2000/00723T patent/TR200000723T2/xx unknown
- 1998-09-15 IL IL13469198A patent/IL134691A0/xx not_active IP Right Cessation
- 1998-09-15 EA EA200000332A patent/EA003989B1/ru not_active IP Right Cessation
- 1998-09-17 IN IN2791DE1998 patent/IN190983B/en unknown
- 1998-09-17 AR ARP980104638A patent/AR013960A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
EA200000332A1 (ru) | 2000-10-30 |
ID25516A (id) | 2000-10-05 |
AU9569498A (en) | 1999-04-05 |
IN190983B (enrdf_load_stackoverflow) | 2003-09-06 |
BR9812649A (pt) | 2000-08-22 |
AR013960A1 (es) | 2001-01-31 |
TR200000723T2 (tr) | 2001-06-21 |
AU747702B2 (en) | 2002-05-16 |
CA2303323A1 (en) | 1999-03-25 |
IL134691A0 (en) | 2001-04-30 |
WO1999014185A1 (en) | 1999-03-25 |
NZ502988A (en) | 2002-08-28 |
CN1272105A (zh) | 2000-11-01 |
EP1015417A1 (en) | 2000-07-05 |
EA003989B1 (ru) | 2003-12-25 |
JP2001516739A (ja) | 2001-10-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100447096B1 (ko) | 바이러스성또는세균성뉴라미니다제의신규한선택적저해제 | |
US5763483A (en) | Carbocyclic compounds | |
KR20010024123A (ko) | 6-원 고리를 갖는 화합물, 그의 제조 방법 및의약물로서의 용도 | |
WO1996026933A9 (en) | Novel selective inhibitors of viral or bacterial neuraminidases | |
US5866601A (en) | Carbocyclic compounds | |
JP2008273948A (ja) | ウイルスまたは細菌ノイラミニダーゼの新規な選択的インヒビター | |
US20040053999A1 (en) | Novel compounds and methods for synthesis and therapy | |
KR20000052702A (ko) | 피페리딘 화합물 | |
US6376674B1 (en) | Piperidine compounds | |
AU2003204079B2 (en) | Novel compounds and methods for synthesis and therapy | |
HK1120494B (en) | Novel compounds and methods for synthesis and therapy | |
HK1115749A (en) | Novel compounds and methods for synthesis and therapy | |
MXPA99003626A (en) | Piperidine compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PA0105 | International application |
Patent event date: 20000317 Patent event code: PA01051R01D Comment text: International Patent Application |
|
PG1501 | Laying open of application | ||
A201 | Request for examination | ||
PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20030909 Comment text: Request for Examination of Application |
|
E902 | Notification of reason for refusal | ||
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20050830 Patent event code: PE09021S01D |
|
E601 | Decision to refuse application | ||
PE0601 | Decision on rejection of patent |
Patent event date: 20060310 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20050830 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |