CA3070717A1 - Inhibitors of plasma kallikrein and uses thereof - Google Patents
Inhibitors of plasma kallikrein and uses thereof Download PDFInfo
- Publication number
- CA3070717A1 CA3070717A1 CA3070717A CA3070717A CA3070717A1 CA 3070717 A1 CA3070717 A1 CA 3070717A1 CA 3070717 A CA3070717 A CA 3070717A CA 3070717 A CA3070717 A CA 3070717A CA 3070717 A1 CA3070717 A1 CA 3070717A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- unsubstituted
- amino
- thiazole
- carbonyl
- 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.)
- Pending
Links
- 102000003827 Plasma Kallikrein Human genes 0.000 title claims description 10
- 108090000113 Plasma Kallikrein Proteins 0.000 title claims description 10
- 239000003112 inhibitor Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 221
- 238000000034 method Methods 0.000 claims abstract description 52
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 45
- 230000000694 effects Effects 0.000 claims abstract description 30
- 206010030113 Oedema Diseases 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 247
- -1 2-((2S,4R)-4-amino-1-(cyclohexanecarbonyl)pyrrolidin-2-yl)-N-((S)-6-guanidino-(methylamino)-1-oxohexan-2-yl)thiazole-4-carboxamide Chemical compound 0.000 claims description 206
- 125000003118 aryl group Chemical group 0.000 claims description 113
- 125000001072 heteroaryl group Chemical group 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 239000001257 hydrogen Substances 0.000 claims description 97
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 83
- 125000000623 heterocyclic group Chemical group 0.000 claims description 81
- 229910052757 nitrogen Inorganic materials 0.000 claims description 80
- 125000000304 alkynyl group Chemical group 0.000 claims description 78
- 229910052799 carbon Inorganic materials 0.000 claims description 71
- 125000003342 alkenyl group Chemical group 0.000 claims description 69
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 67
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 67
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 64
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 55
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 54
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
- 229910052717 sulfur Inorganic materials 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 201000010099 disease Diseases 0.000 claims description 38
- 206010019860 Hereditary angioedema Diseases 0.000 claims description 35
- 125000002252 acyl group Chemical group 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- 230000002401 inhibitory effect Effects 0.000 claims description 29
- 125000005549 heteroarylene group Chemical group 0.000 claims description 27
- 230000001404 mediated effect Effects 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims description 20
- 201000011190 diabetic macular edema Diseases 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 208000022873 Ocular disease Diseases 0.000 claims description 5
- VCKGTIQQFDCCCA-WWGRRREGSA-N CNC(=O)[C@H](CCC(N)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCC(N)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 VCKGTIQQFDCCCA-WWGRRREGSA-N 0.000 claims description 4
- PEWLWWZHNVFXPW-AOIWGVFYSA-N N[C@@H]1C[C@H](N(C1)C(=O)OCC1=CC(=CC=C1)Cl)C=1SC=C(N=1)C(N[C@H](C(=O)NC)CCCCNC(=N)N)=O Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)OCC1=CC(=CC=C1)Cl)C=1SC=C(N=1)C(N[C@H](C(=O)NC)CCCCNC(=N)N)=O PEWLWWZHNVFXPW-AOIWGVFYSA-N 0.000 claims description 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 4
- 208000002780 macular degeneration Diseases 0.000 claims description 4
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 210000005260 human cell Anatomy 0.000 claims description 2
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- GJGFBTQCJROWAU-UFKRDZGPSA-N 2-[(2S,4R)-4-amino-1-(5-chloro-3a,7a-dihydro-1,3-benzothiazole-2-carbonyl)pyrrolidin-2-yl]-N-[(2S)-6-(diaminomethylideneamino)-1-(methylamino)-1-oxohexan-2-yl]-1,3-thiazole-4-carboxamide Chemical compound CNC(=O)[C@H](CCCCN=C(N)N)NC(=O)C1=CSC(=N1)[C@@H]2C[C@H](CN2C(=O)C3=NC4C=C(C=CC4S3)Cl)N GJGFBTQCJROWAU-UFKRDZGPSA-N 0.000 claims 2
- BXOSIXVQJVFKRG-URVUXULASA-N C1=C(C=CC2=CC=CC=C12)C(=O)N1[C@@H](C[C@H](C1)N)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound C1=C(C=CC2=CC=CC=C12)C(=O)N1[C@@H](C[C@H](C1)N)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N BXOSIXVQJVFKRG-URVUXULASA-N 0.000 claims 2
- LSDUXDLFSXDPQA-UZLBHIALSA-N CC1=C(CCNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=NC(N)=C1 Chemical compound CC1=C(CCNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=NC(N)=C1 LSDUXDLFSXDPQA-UZLBHIALSA-N 0.000 claims 2
- BSTKXPMFPPOUDP-HXOBKFHXSA-N CC1=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=C2C=CN=C(N)C2=C1 Chemical compound CC1=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=C2C=CN=C(N)C2=C1 BSTKXPMFPPOUDP-HXOBKFHXSA-N 0.000 claims 2
- NIKWDISSLUKVAJ-BEFAXECRSA-N CC1=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=NC(N)=C1 Chemical compound CC1=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=NC(N)=C1 NIKWDISSLUKVAJ-BEFAXECRSA-N 0.000 claims 2
- BPUYBKGHVHAYKC-GJYPPUQNSA-N CN(C)C(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CN(C)C(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 BPUYBKGHVHAYKC-GJYPPUQNSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-RKVPGOIHSA-N CNC(=O)[C@@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-RKVPGOIHSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-IIDMSEBBSA-N CNC(=O)[C@@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-IIDMSEBBSA-N 0.000 claims 2
- DCRZJWUVOAVWGB-MMOPVJDHSA-N CNC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 DCRZJWUVOAVWGB-MMOPVJDHSA-N 0.000 claims 2
- IAAFGUQPPVMZNX-MONBJTKQSA-N CNC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 IAAFGUQPPVMZNX-MONBJTKQSA-N 0.000 claims 2
- YZUIZAHXHMYKIB-XUWXXGDYSA-N CNC(=O)[C@H](CC1=CNC=N1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CC1=CNC=N1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 YZUIZAHXHMYKIB-XUWXXGDYSA-N 0.000 claims 2
- IQKGPQDSABYVQE-VKJFTORMSA-N CNC(=O)[C@H](CCCCN)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCN)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 IQKGPQDSABYVQE-VKJFTORMSA-N 0.000 claims 2
- QREFANRJXDCKQV-UWVAXJGDSA-N CNC(=O)[C@H](CCCCNC(C)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(C)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 QREFANRJXDCKQV-UWVAXJGDSA-N 0.000 claims 2
- KOVNKSCBSLWDLG-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(C=CC2=N1)C(F)(F)F Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(C=CC2=N1)C(F)(F)F KOVNKSCBSLWDLG-VKJFTORMSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-VKJFTORMSA-N 0.000 claims 2
- RIBQIUQETAVSCK-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(I)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(I)C=CC2=N1 RIBQIUQETAVSCK-VKJFTORMSA-N 0.000 claims 2
- HZBXWCRJRXMOSH-ALKREAHSSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(OC)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(OC)C=CC2=N1 HZBXWCRJRXMOSH-ALKREAHSSA-N 0.000 claims 2
- IQXORBRTZBSKJQ-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=CC=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=CC=CC2=N1 IQXORBRTZBSKJQ-VKJFTORMSA-N 0.000 claims 2
- ZMMPESRTVFDXKA-UWVAXJGDSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O ZMMPESRTVFDXKA-UWVAXJGDSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-MPGHIAIKSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-MPGHIAIKSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-RVKKMQEKSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-RVKKMQEKSA-N 0.000 claims 2
- ZMMPESRTVFDXKA-FUHIMQAGSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O ZMMPESRTVFDXKA-FUHIMQAGSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-RLFYNMQTSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-RLFYNMQTSA-N 0.000 claims 2
- KIXZDQAGELDAQB-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 KIXZDQAGELDAQB-VKJFTORMSA-N 0.000 claims 2
- UGKMOJZOTINLEE-KEYYUXOJSA-N CNC(=O)[C@H](CCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 UGKMOJZOTINLEE-KEYYUXOJSA-N 0.000 claims 2
- YUPDPXYEIFAQRA-NQIIRXRSSA-N NCC1=CC=C(CCNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C=C1 Chemical compound NCC1=CC=C(CCNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C=C1 YUPDPXYEIFAQRA-NQIIRXRSSA-N 0.000 claims 2
- FHGGDJNWGJXNMM-XLIONFOSSA-N NCC1=CC=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C=C1 Chemical compound NCC1=CC=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C=C1 FHGGDJNWGJXNMM-XLIONFOSSA-N 0.000 claims 2
- FDABKPHXIICLML-SKDZVZGDSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C(=C2)Cl)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C(=C2)Cl)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N FDABKPHXIICLML-SKDZVZGDSA-N 0.000 claims 2
- CBXMSTBUKVKBJV-AOIWGVFYSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N CBXMSTBUKVKBJV-AOIWGVFYSA-N 0.000 claims 2
- UCKDBXMZROGZMA-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N UCKDBXMZROGZMA-RYRKJORJSA-N 0.000 claims 2
- OZQHKLQLDUISBY-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)C(F)(F)F)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)C(F)(F)F)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N OZQHKLQLDUISBY-RYRKJORJSA-N 0.000 claims 2
- JZEDSUAQAVMEMU-NUJGCVRESA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)Cl)C=1SC=C(N=1)C(=O)N[C@@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)Cl)C=1SC=C(N=1)C(=O)N[C@@H](C(=O)NC)CCCCNC(=N)N JZEDSUAQAVMEMU-NUJGCVRESA-N 0.000 claims 2
- JZEDSUAQAVMEMU-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N JZEDSUAQAVMEMU-RYRKJORJSA-N 0.000 claims 2
- SNRDAMCHFNCWJG-SKDZVZGDSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC=C2Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC=C2Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N SNRDAMCHFNCWJG-SKDZVZGDSA-N 0.000 claims 2
- FKQMDAAKAOWPEB-QRWLVFNGSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=C2C=C(Cl)C=CN2C=N1 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=C2C=C(Cl)C=CN2C=N1 FKQMDAAKAOWPEB-QRWLVFNGSA-N 0.000 claims 2
- UGVFMASJHLZOFK-OFNKIYASSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC2=CC=C(Cl)C=C2C=C1 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC2=CC=C(Cl)C=C2C=C1 UGVFMASJHLZOFK-OFNKIYASSA-N 0.000 claims 2
- ISBGVOZOKHEQDV-APWZRJJASA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C(C=C1)C(N)=N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C(C=C1)C(N)=N ISBGVOZOKHEQDV-APWZRJJASA-N 0.000 claims 2
- SYUKSGXOSHFNNI-UTKZUKDTSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C2C(N)=NC=CC2=C1 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C2C(N)=NC=CC2=C1 SYUKSGXOSHFNNI-UTKZUKDTSA-N 0.000 claims 2
- GPNHMIMNKBPCPE-VLIAUNLRSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=C(Cl)C=C2 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=C(Cl)C=C2 GPNHMIMNKBPCPE-VLIAUNLRSA-N 0.000 claims 2
- ZVVYLCGUZJCAEU-VLIAUNLRSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=CC(Cl)=C2 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=CC(Cl)=C2 ZVVYLCGUZJCAEU-VLIAUNLRSA-N 0.000 claims 2
- VMZMWVBYMSGTPQ-XLIONFOSSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCC1=CC=C(C=C1)C(N)=N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCC1=CC=C(C=C1)C(N)=N VMZMWVBYMSGTPQ-XLIONFOSSA-N 0.000 claims 2
- GFDKMJFZUDZXRK-GCJKJVERSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCC1=CC=C2C(N)=NC=CC2=C1 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCC1=CC=C2C(N)=NC=CC2=C1 GFDKMJFZUDZXRK-GCJKJVERSA-N 0.000 claims 2
- KBCPCNVORWUACK-PBHICJAKSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCCCCNC(N)=N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCCCCNC(N)=N KBCPCNVORWUACK-PBHICJAKSA-N 0.000 claims 2
- YGODCUSSYXRBRZ-KEYYUXOJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)N[C@@H](CCCCNC(N)=N)C(N)=O Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)N[C@@H](CCCCNC(N)=N)C(N)=O YGODCUSSYXRBRZ-KEYYUXOJSA-N 0.000 claims 2
- GEJBSTPNTAGZPN-MMOPVJDHSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N GEJBSTPNTAGZPN-MMOPVJDHSA-N 0.000 claims 2
- JBGMLHNBLWKMJG-LMNJBCLMSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=C(C=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=C(C=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N JBGMLHNBLWKMJG-LMNJBCLMSA-N 0.000 claims 2
- PBOYRHRFMVZNFR-KPFFTGBYSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=CC(=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=CC(=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N PBOYRHRFMVZNFR-KPFFTGBYSA-N 0.000 claims 2
- MBWBDEMKWGRUJD-LJHODMEESA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=CC2=C(SC=C2Cl)C=1)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=CC2=C(SC=C2Cl)C=1)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N MBWBDEMKWGRUJD-LJHODMEESA-N 0.000 claims 2
- MLEJYXYWKYQGTH-LMNJBCLMSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=NC2=CC=C(C=C2C=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=NC2=CC=C(C=C2C=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N MLEJYXYWKYQGTH-LMNJBCLMSA-N 0.000 claims 2
- OMCCBPSINYKNOP-KEYYUXOJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1N=C(N(C=1)C)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1N=C(N(C=1)C)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N OMCCBPSINYKNOP-KEYYUXOJSA-N 0.000 claims 2
- KSHXZRSWQOKILX-IPYPFGDCSA-N N[C@@H]1C[C@H](N(C1)C(C(C)C)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(C(C)C)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N KSHXZRSWQOKILX-IPYPFGDCSA-N 0.000 claims 2
- OCYCSLVKSPDLTL-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(C1=CC=CC=C1)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(C1=CC=CC=C1)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N OCYCSLVKSPDLTL-RYRKJORJSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 147
- 102100035792 Kininogen-1 Human genes 0.000 abstract description 9
- 101800004538 Bradykinin Proteins 0.000 abstract description 8
- 102000012479 Serine Proteases Human genes 0.000 abstract description 3
- 108010022999 Serine Proteases Proteins 0.000 abstract description 3
- 208000037765 diseases and disorders Diseases 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 230000000770 proinflammatory effect Effects 0.000 abstract description 2
- 229940124549 vasodilator Drugs 0.000 abstract description 2
- 239000003071 vasodilator agent Substances 0.000 abstract description 2
- 108010077861 Kininogens Proteins 0.000 abstract 1
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
- PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 description 137
- 125000005842 heteroatom Chemical group 0.000 description 125
- 125000004432 carbon atom Chemical group C* 0.000 description 115
- 239000000243 solution Substances 0.000 description 76
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 75
- 235000002639 sodium chloride Nutrition 0.000 description 75
- 238000003786 synthesis reaction Methods 0.000 description 73
- 230000015572 biosynthetic process Effects 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 58
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 49
- 239000012453 solvate Substances 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 43
- 239000000651 prodrug Substances 0.000 description 43
- 229940002612 prodrug Drugs 0.000 description 43
- 239000007787 solid Substances 0.000 description 42
- 239000013078 crystal Substances 0.000 description 41
- 239000001301 oxygen Substances 0.000 description 39
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000011593 sulfur Substances 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 239000002904 solvent Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 241000282414 Homo sapiens Species 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 241001465754 Metazoa Species 0.000 description 29
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 description 28
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- 125000001424 substituent group Chemical group 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- 239000008177 pharmaceutical agent Substances 0.000 description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 210000001519 tissue Anatomy 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 21
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 20
- 239000003814 drug Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
- 238000011282 treatment Methods 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 239000003208 petroleum Substances 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 150000003384 small molecules Chemical class 0.000 description 16
- 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 16
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 150000004677 hydrates Chemical class 0.000 description 14
- 239000003755 preservative agent Substances 0.000 description 14
- 239000000377 silicon dioxide Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 125000001246 bromo group Chemical group Br* 0.000 description 12
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 12
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
- 239000000546 pharmaceutical excipient Substances 0.000 description 12
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 12
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 12
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 11
- 239000007821 HATU Substances 0.000 description 11
- 229920002472 Starch Polymers 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 125000002346 iodo group Chemical group I* 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- 235000019698 starch Nutrition 0.000 description 11
- 208000024891 symptom Diseases 0.000 description 11
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 10
- 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 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- 235000010216 calcium carbonate Nutrition 0.000 description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229960004756 ethanol Drugs 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 10
- 229940032147 starch Drugs 0.000 description 10
- 239000008107 starch Substances 0.000 description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
- 150000003857 carboxamides Chemical class 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 230000001225 therapeutic effect Effects 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 229960003563 calcium carbonate Drugs 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 7
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 235000010443 alginic acid Nutrition 0.000 description 7
- 229920000615 alginic acid Polymers 0.000 description 7
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 7
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 150000002148 esters Chemical group 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000004007 reversed phase HPLC Methods 0.000 description 7
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 6
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229940126543 compound 14 Drugs 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 230000000069 prophylactic effect Effects 0.000 description 6
- 238000011321 prophylaxis Methods 0.000 description 6
- 125000005551 pyridylene group Chemical group 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 6
- 239000005720 sucrose Substances 0.000 description 6
- 229940124597 therapeutic agent Drugs 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 241000283690 Bos taurus Species 0.000 description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 5
- 241000283707 Capra Species 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- 241000283073 Equus caballus Species 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- 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 5
- 241000282898 Sus scrofa Species 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 239000003701 inert diluent Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 description 5
- 239000006187 pill Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 235000018102 proteins Nutrition 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 239000007909 solid dosage form Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 5
- 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 5
- 239000001993 wax Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 4
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 4
- CYMKPNOSXLFDNC-VFNWGFHPSA-N C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@H](NC1)C=1SC=C(N=1)C(=O)OCC Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@H](NC1)C=1SC=C(N=1)C(=O)OCC CYMKPNOSXLFDNC-VFNWGFHPSA-N 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- 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 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 4
- 239000000783 alginic acid Substances 0.000 description 4
- 229960001126 alginic acid Drugs 0.000 description 4
- 150000004781 alginic acids Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000001099 ammonium carbonate Substances 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 229940050390 benzoate Drugs 0.000 description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 4
- 239000012472 biological sample Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000006172 buffering agent Substances 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 4
- 229940105329 carboxymethylcellulose Drugs 0.000 description 4
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 230000009261 transgenic effect Effects 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- WDWRIVZIPSHUOR-RNFRBKRXSA-N (2r,4r)-4-azaniumyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@H](N)C[C@@H]1C(O)=O WDWRIVZIPSHUOR-RNFRBKRXSA-N 0.000 description 3
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- NNBVAZYHYUBQCU-ZIAGYGMSSA-N 2-o-benzyl 1-o-tert-butyl (2r,4r)-4-azidopyrrolidine-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@H](N=[N+]=[N-])C[C@@H]1C(=O)OCC1=CC=CC=C1 NNBVAZYHYUBQCU-ZIAGYGMSSA-N 0.000 description 3
- BEIPCYKSYYZEJH-UONOGXRCSA-N 2-o-benzyl 1-o-tert-butyl (2r,4s)-4-hydroxypyrrolidine-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](O)C[C@@H]1C(=O)OCC1=CC=CC=C1 BEIPCYKSYYZEJH-UONOGXRCSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- AJEVCBHFXLJUGI-QWHCGFSZSA-N C(C1=CC=CC=C1)(=O)O[C@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=O Chemical compound C(C1=CC=CC=C1)(=O)O[C@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=O AJEVCBHFXLJUGI-QWHCGFSZSA-N 0.000 description 3
- USVLGBPHQHWCFK-QWHCGFSZSA-N C(C1=CC=CC=C1)(=O)O[C@H]1C[C@@H](NC1)C=1SC=C(N=1)C(=O)OCC Chemical compound C(C1=CC=CC=C1)(=O)O[C@H]1C[C@@H](NC1)C=1SC=C(N=1)C(=O)OCC USVLGBPHQHWCFK-QWHCGFSZSA-N 0.000 description 3
- CYMKPNOSXLFDNC-QVKFZJNVSA-N C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@@H](NC1)C=1SC=C(N=1)C(=O)OCC Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@@H](NC1)C=1SC=C(N=1)C(=O)OCC CYMKPNOSXLFDNC-QVKFZJNVSA-N 0.000 description 3
- CCNKYUBKDFOZFX-IUODEOHRSA-N CC(C)(C)OC(=O)N[C@@H]1C[C@@H](N(C1)C(=O)C1=CN2C=CC(Cl)=CC2=N1)C1=NC(=CS1)C(O)=O Chemical compound CC(C)(C)OC(=O)N[C@@H]1C[C@@H](N(C1)C(=O)C1=CN2C=CC(Cl)=CC2=N1)C1=NC(=CS1)C(O)=O CCNKYUBKDFOZFX-IUODEOHRSA-N 0.000 description 3
- ZSCSJFWNJQFETJ-FXAWDEMLSA-N CCOC(=O)C1=CSC(=N1)[C@H]1C[C@@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)OC(=O)C1=CC=CC=C1 Chemical compound CCOC(=O)C1=CSC(=N1)[C@H]1C[C@@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)OC(=O)C1=CC=CC=C1 ZSCSJFWNJQFETJ-FXAWDEMLSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 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 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 description 3
- 229940122601 Esterase inhibitor Drugs 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 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 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- FXVDJTGOAYCFTC-BXKDBHETSA-N N[C@@H]1C[C@@H](N(C1)C(=O)C1=CN2C=CC(Cl)=CC2=N1)C1=NC(=CS1)C(O)=O Chemical compound N[C@@H]1C[C@@H](N(C1)C(=O)C1=CN2C=CC(Cl)=CC2=N1)C1=NC(=CS1)C(O)=O FXVDJTGOAYCFTC-BXKDBHETSA-N 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 241000009328 Perro Species 0.000 description 3
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 208000000208 Wet Macular Degeneration Diseases 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- 235000012216 bentonite Nutrition 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 3
- KVERNDRXLDWSFC-LLVKDONJSA-N benzyl (2r)-2-carbamothioylpyrrolidine-1-carboxylate Chemical compound NC(=S)[C@H]1CCCN1C(=O)OCC1=CC=CC=C1 KVERNDRXLDWSFC-LLVKDONJSA-N 0.000 description 3
- ZCGHEBMEQXMRQL-LLVKDONJSA-N benzyl (2r)-2-carbamoylpyrrolidine-1-carboxylate Chemical compound NC(=O)[C@H]1CCCN1C(=O)OCC1=CC=CC=C1 ZCGHEBMEQXMRQL-LLVKDONJSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 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 3
- 239000011230 binding agent Substances 0.000 description 3
- 229960000074 biopharmaceutical Drugs 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229960004106 citric acid Drugs 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940099112 cornstarch Drugs 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 208000011325 dry age related macular degeneration Diseases 0.000 description 3
- 239000002329 esterase inhibitor Substances 0.000 description 3
- FPKKLJNBKCOWQD-OAHLLOKOSA-N ethyl 2-[(2R)-1-phenylmethoxycarbonylpyrrolidin-2-yl]-1,3-thiazole-4-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)N1[C@H](CCC1)C=1SC=C(N=1)C(=O)OCC FPKKLJNBKCOWQD-OAHLLOKOSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 229940050410 gluconate Drugs 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
- 150000007523 nucleic acids Chemical class 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 230000008685 targeting Effects 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- 238000003419 tautomerization reaction Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 3
- 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 3
- 230000002792 vascular Effects 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- WMSUFWLPZLCIHP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 9h-fluoren-9-ylmethyl carbonate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)ON1C(=O)CCC1=O WMSUFWLPZLCIHP-UHFFFAOYSA-N 0.000 description 2
- UPXRTVAIJMUAQR-QVKFZJNVSA-N (2r,4r)-4-(9h-fluoren-9-ylmethoxycarbonylamino)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1[C@H](C(O)=O)N(C(=O)OC(C)(C)C)C[C@@H]1NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 UPXRTVAIJMUAQR-QVKFZJNVSA-N 0.000 description 2
- HKMZRZUEADSZDQ-DZJWSCHMSA-N (2s)-2-[[(2s,3as,7as)-1-[(3r)-2-[(2s)-2-[[(2s)-2-[[2-[[(2s,4r)-1-[(2s)-1-[(2s)-2-[[(2r)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]acetyl]amino]-3- Chemical compound CC(O)=O.NC(N)=NCCC[C@@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2SC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@H](CC3=CC=CC=C3C2)C(=O)N2[C@@H](C[C@@H]3CCCC[C@@H]32)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C[C@@H](O)C1 HKMZRZUEADSZDQ-DZJWSCHMSA-N 0.000 description 2
- UPXRTVAIJMUAQR-VFNWGFHPSA-N (2s,4r)-4-(9h-fluoren-9-ylmethoxycarbonylamino)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)C[C@@H]1NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 UPXRTVAIJMUAQR-VFNWGFHPSA-N 0.000 description 2
- WTKQMHWYSBWUBE-UHFFFAOYSA-N (3-nitropyridin-2-yl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CN=C1SCl WTKQMHWYSBWUBE-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- GLUABPSZMHYCNO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,2-b]pyrrole Chemical compound N1CCC2NCCC21 GLUABPSZMHYCNO-UHFFFAOYSA-N 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- LDZNCSVWVMBVST-UHFFFAOYSA-N 2-trimethylsilylethyl hydrogen carbonate Chemical compound C[Si](C)(C)CCOC(O)=O LDZNCSVWVMBVST-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- 229940123765 Bradykinin B2 receptor antagonist Drugs 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- XCOSMHNXTKWVNF-BXUZGUMPSA-N C(C)(=O)N[C@@H]1C[C@@H](N(C1)C(=O)C=1N=C2N(C=CC(=C2)Cl)C=1)C=1SC=C(N=1)C(=O)O Chemical compound C(C)(=O)N[C@@H]1C[C@@H](N(C1)C(=O)C=1N=C2N(C=CC(=C2)Cl)C=1)C=1SC=C(N=1)C(=O)O XCOSMHNXTKWVNF-BXUZGUMPSA-N 0.000 description 2
- FJTVNXXFCJXKIC-QWHCGFSZSA-N C(C1=CC=CC=C1)(=O)O[C@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=S Chemical compound C(C1=CC=CC=C1)(=O)O[C@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=S FJTVNXXFCJXKIC-QWHCGFSZSA-N 0.000 description 2
- FGYWXQWBEVECRF-MNNSJKJDSA-N C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@H](N(C1)C(=O)OCC1=CC(=CC=C1)Cl)C=1SC=C(N=1)C(=O)OCC Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@H](N(C1)C(=O)OCC1=CC(=CC=C1)Cl)C=1SC=C(N=1)C(=O)OCC FGYWXQWBEVECRF-MNNSJKJDSA-N 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- KRVPMWSNZXEHCA-CQSZACIVSA-N CCOC(=O)C1=CSC(=N1)[C@H]1CCCN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CCOC(=O)C1=CSC(=N1)[C@H]1CCCN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 KRVPMWSNZXEHCA-CQSZACIVSA-N 0.000 description 2
- YGPIMJDBYSCXKF-PIIWDFAUSA-N CCOC(=O)C1=CSC(=N1)[C@H]1C[C@H](CN1C(=O)C1=CN2C=CC(Cl)=CC2=N1)NC(=O)OCC1C2=CC=CC=C2C2=C1C=CC=C2 Chemical compound CCOC(=O)C1=CSC(=N1)[C@H]1C[C@H](CN1C(=O)C1=CN2C=CC(Cl)=CC2=N1)NC(=O)OCC1C2=CC=CC=C2C2=C1C=CC=C2 YGPIMJDBYSCXKF-PIIWDFAUSA-N 0.000 description 2
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 2
- 101001081555 Homo sapiens Plasma protease C1 inhibitor Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 241000270322 Lepidosauria Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- 240000003183 Manihot esculenta Species 0.000 description 2
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
- BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 description 2
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical class CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- MYFNUOGAHBZRJR-GFCCVEGCSA-N OC(=O)C1=CSC(=N1)[C@H]1CCCN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound OC(=O)C1=CSC(=N1)[C@H]1CCCN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 MYFNUOGAHBZRJR-GFCCVEGCSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 2
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 108010081667 aflibercept Proteins 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229940023476 agar Drugs 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005377 alkyl thioxy group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 2
- 125000005165 aryl thioxy group Chemical group 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 229940009098 aspartate Drugs 0.000 description 2
- 125000002785 azepinyl group Chemical group 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229940075791 berinert Drugs 0.000 description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- IEPBPSSCIZTJIF-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) carbonate Chemical compound ClC(Cl)(Cl)COC(=O)OCC(Cl)(Cl)Cl IEPBPSSCIZTJIF-UHFFFAOYSA-N 0.000 description 2
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003359 bradykinin B2 receptor antagonist Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229960005069 calcium Drugs 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229960002798 cetrimide Drugs 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 2
- NFCRBQADEGXVDL-UHFFFAOYSA-M cetylpyridinium chloride monohydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NFCRBQADEGXVDL-UHFFFAOYSA-M 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229960004926 chlorobutanol Drugs 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 229940088949 cinryze Drugs 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 235000019700 dicalcium phosphate Nutrition 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 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 2
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 108010011867 ecallantide Proteins 0.000 description 2
- 229960001174 ecallantide Drugs 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- JJHURWNVNPTRCK-OGFXRTJISA-N ethyl 2-[(2R)-pyrrolidin-2-yl]-1,3-thiazole-4-carboxylate hydrobromide Chemical compound Br.N1[C@H](CCC1)C=1SC=C(N=1)C(=O)OCC JJHURWNVNPTRCK-OGFXRTJISA-N 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940050762 firazyr Drugs 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000003979 granulating agent Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 125000005378 heteroarylthioxy group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- 102000044507 human SERPING1 Human genes 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- VBGWSQKGUZHFPS-VGMMZINCSA-N kalbitor Chemical compound C([C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]2C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=3C=CC=CC=3)C(=O)N[C@H](C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)NCC(=O)NCC(=O)N[C@H]3CSSC[C@H](NC(=O)[C@@H]4CCCN4C(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CO)NC(=O)[C@H](CC=4NC=NC=4)NC(=O)[C@H](CCSC)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCC(O)=O)CSSC[C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC3=O)CSSC2)C(=O)N[C@@H]([C@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=2NC=NC=2)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N1)[C@@H](C)CC)[C@H](C)O)=O)[C@@H](C)CC)C1=CC=CC=C1 VBGWSQKGUZHFPS-VGMMZINCSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229940001447 lactate Drugs 0.000 description 2
- 229950005287 lanadelumab Drugs 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 210000002751 lymph Anatomy 0.000 description 2
- 229940049920 malate Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 238000013188 needle biopsy Methods 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 235000014571 nuts Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000003585 oxepinyl group Chemical group 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
- 229920001993 poloxamer 188 Polymers 0.000 description 2
- 239000008389 polyethoxylated castor oil Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 235000007686 potassium Nutrition 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 2
- 229940043349 potassium metabisulfite Drugs 0.000 description 2
- 235000010263 potassium metabisulphite Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229960004063 propylene glycol Drugs 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
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 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
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229940083542 sodium Drugs 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 229940001607 sodium bisulfite Drugs 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 235000011083 sodium citrates Nutrition 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 235000011008 sodium phosphates Nutrition 0.000 description 2
- 229920003109 sodium starch glycolate Polymers 0.000 description 2
- 229940079832 sodium starch glycolate Drugs 0.000 description 2
- 239000008109 sodium starch glycolate Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 235000010199 sorbic acid Nutrition 0.000 description 2
- 239000004334 sorbic acid Substances 0.000 description 2
- 229940075582 sorbic acid Drugs 0.000 description 2
- 235000011078 sorbitan tristearate Nutrition 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- FNKPUROILDFTQA-VFNWGFHPSA-N tert-butyl (2S,4R)-2-carbamothioyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-1-carboxylate Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(N)=S FNKPUROILDFTQA-VFNWGFHPSA-N 0.000 description 2
- FSKXQQQRAARGRY-VFNWGFHPSA-N tert-butyl (2S,4R)-2-carbamoyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-1-carboxylate Chemical compound C1[C@@H](C(N)=O)N(C(=O)OC(C)(C)C)C[C@@H]1NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 FSKXQQQRAARGRY-VFNWGFHPSA-N 0.000 description 2
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000003777 thiepinyl group Chemical group 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 125000000464 thioxo group Chemical group S=* 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 125000005558 triazinylene group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- FTVXFBJENACRRL-UHFFFAOYSA-N (1-hydroxypiperidin-2-yl) carbamate Chemical compound NC(=O)OC1CCCCN1O FTVXFBJENACRRL-UHFFFAOYSA-N 0.000 description 1
- KLWCNEYVHPBUNM-UHFFFAOYSA-N (1-methylcyclobutyl) carbamate Chemical compound NC(=O)OC1(C)CCC1 KLWCNEYVHPBUNM-UHFFFAOYSA-N 0.000 description 1
- AKIHTGIGOHBKGE-UHFFFAOYSA-N (1-methylcyclohexyl) carbamate Chemical compound NC(=O)OC1(C)CCCCC1 AKIHTGIGOHBKGE-UHFFFAOYSA-N 0.000 description 1
- QYYZXEPEVBXNNA-QGZVFWFLSA-N (1R)-2-acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-5-methylsulfonyl-1,3-dihydroisoindole-1-carboxamide Chemical compound C(C)(=O)N1[C@H](C2=CC=C(C=C2C1)S(=O)(=O)C)C(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O QYYZXEPEVBXNNA-QGZVFWFLSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- ZLIHDHDAJVINAN-UHFFFAOYSA-N (2,4,6-trimethyl-3-pyridin-2-ylphenyl)methanimine Chemical compound CC1=C(C=N)C(C)=CC(C)=C1C1=CC=CC=N1 ZLIHDHDAJVINAN-UHFFFAOYSA-N 0.000 description 1
- KJOPTLWVYZCJBX-UHFFFAOYSA-N (2,4,6-trimethylphenyl)methyl carbamate Chemical compound CC1=CC(C)=C(COC(N)=O)C(C)=C1 KJOPTLWVYZCJBX-UHFFFAOYSA-N 0.000 description 1
- IUZVXNNZBSTDJT-UHFFFAOYSA-N (2,4,6-tritert-butylphenyl) carbamate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(OC(N)=O)C(C(C)(C)C)=C1 IUZVXNNZBSTDJT-UHFFFAOYSA-N 0.000 description 1
- LZZRHUUMSXNYBI-UHFFFAOYSA-N (2,4-dichlorophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C(Cl)C=C1Cl LZZRHUUMSXNYBI-UHFFFAOYSA-N 0.000 description 1
- LEDMDNAHWYVAPC-UHFFFAOYSA-N (2-carbamoylphenyl)methyl benzoate Chemical compound NC(=O)C1=CC=CC=C1COC(=O)C1=CC=CC=C1 LEDMDNAHWYVAPC-UHFFFAOYSA-N 0.000 description 1
- SWHAGWLVMRLFKO-UHFFFAOYSA-N (2-nitrophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1[N+]([O-])=O SWHAGWLVMRLFKO-UHFFFAOYSA-N 0.000 description 1
- PMIODTBPFKLUMF-UHFFFAOYSA-N (2-nitrophenyl)methyl hydrogen carbonate Chemical compound OC(=O)OCC1=CC=CC=C1[N+]([O-])=O PMIODTBPFKLUMF-UHFFFAOYSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- WDWRIVZIPSHUOR-RQJHMYQMSA-N (2s,4r)-4-azaniumyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@H](N)C[C@H]1C(O)=O WDWRIVZIPSHUOR-RQJHMYQMSA-N 0.000 description 1
- ZTESKPLFUKCHOF-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methyl hydrogen carbonate Chemical compound COC1=CC=C(COC(O)=O)C=C1OC ZTESKPLFUKCHOF-UHFFFAOYSA-N 0.000 description 1
- HIPYHINICCKLGX-UHFFFAOYSA-N (3,5-dimethoxyphenyl)methyl carbamate Chemical compound COC1=CC(COC(N)=O)=CC(OC)=C1 HIPYHINICCKLGX-UHFFFAOYSA-N 0.000 description 1
- ZSRDNPVYGSFUMD-UHFFFAOYSA-N (3-chlorophenyl)methanol Chemical compound OCC1=CC=CC(Cl)=C1 ZSRDNPVYGSFUMD-UHFFFAOYSA-N 0.000 description 1
- YVOBGLMMNWZYCL-UHFFFAOYSA-N (3-nitrophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC([N+]([O-])=O)=C1 YVOBGLMMNWZYCL-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- AWOKSNNHYRGYIA-UHFFFAOYSA-N (4,5-dimethoxy-2-nitrophenyl)methyl carbamate Chemical compound COC1=CC(COC(N)=O)=C([N+]([O-])=O)C=C1OC AWOKSNNHYRGYIA-UHFFFAOYSA-N 0.000 description 1
- XHTUZBFAOYRMHI-UHFFFAOYSA-N (4-bromophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C(Br)C=C1 XHTUZBFAOYRMHI-UHFFFAOYSA-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
- HIIOEWGKFCWTJU-UHFFFAOYSA-N (4-chlorophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C(Cl)C=C1 HIIOEWGKFCWTJU-UHFFFAOYSA-N 0.000 description 1
- NULWVEYYQSYAHP-UHFFFAOYSA-N (4-cyanophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C(C#N)C=C1 NULWVEYYQSYAHP-UHFFFAOYSA-N 0.000 description 1
- IERCGNSLWQVTPC-UHFFFAOYSA-N (4-decoxyphenyl)methyl carbamate Chemical compound CCCCCCCCCCOC1=CC=C(COC(N)=O)C=C1 IERCGNSLWQVTPC-UHFFFAOYSA-N 0.000 description 1
- QXENIPSNYCZWNY-UHFFFAOYSA-N (4-methoxyphenyl)-diphenylmethanamine Chemical compound C1=CC(OC)=CC=C1C(N)(C=1C=CC=CC=1)C1=CC=CC=C1 QXENIPSNYCZWNY-UHFFFAOYSA-N 0.000 description 1
- OKLFHGKWEQKSDZ-UHFFFAOYSA-N (4-methoxyphenyl)methanimine Chemical compound COC1=CC=C(C=N)C=C1 OKLFHGKWEQKSDZ-UHFFFAOYSA-N 0.000 description 1
- SDEOSHAQCMPJIJ-UHFFFAOYSA-N (4-methoxyphenyl)methyl carbamate Chemical compound COC1=CC=C(COC(N)=O)C=C1 SDEOSHAQCMPJIJ-UHFFFAOYSA-N 0.000 description 1
- HZFLPRPFCHEBPQ-UHFFFAOYSA-N (4-methoxyphenyl)methyl hydrogen carbonate Chemical compound COC1=CC=C(COC(O)=O)C=C1 HZFLPRPFCHEBPQ-UHFFFAOYSA-N 0.000 description 1
- WNNZAHBBDIVWBB-UHFFFAOYSA-N (4-methylsulfanylphenyl) carbamate Chemical compound CSC1=CC=C(OC(N)=O)C=C1 WNNZAHBBDIVWBB-UHFFFAOYSA-N 0.000 description 1
- RZTAQRMRWPYVRR-UHFFFAOYSA-N (4-methylsulfinylphenyl)methyl carbamate Chemical compound CS(=O)C1=CC=C(COC(N)=O)C=C1 RZTAQRMRWPYVRR-UHFFFAOYSA-N 0.000 description 1
- LRJOVUGHUMSKFA-UHFFFAOYSA-N (4-nitrophenyl)methanimine Chemical compound [O-][N+](=O)C1=CC=C(C=N)C=C1 LRJOVUGHUMSKFA-UHFFFAOYSA-N 0.000 description 1
- FPBOSUGVPBRYCA-UHFFFAOYSA-N (4-nitrophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 FPBOSUGVPBRYCA-UHFFFAOYSA-N 0.000 description 1
- HQNKOEZESXBYJA-UHFFFAOYSA-N (4-phenyldiazenylphenyl)methyl carbamate Chemical compound C1=CC(COC(=O)N)=CC=C1N=NC1=CC=CC=C1 HQNKOEZESXBYJA-UHFFFAOYSA-N 0.000 description 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 description 1
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 1
- 125000006587 (C5-C10) heteroarylene group Chemical group 0.000 description 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RASLWNGTMHFPIQ-AATRIKPKSA-N (e)-3-(2-nitrophenyl)prop-2-enamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1[N+]([O-])=O RASLWNGTMHFPIQ-AATRIKPKSA-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
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 125000005904 1,2,3,4-tetrahydro-1,6-naphthyridinyl group Chemical group 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
- TTXKLVVJWALEOY-UHFFFAOYSA-N 1,2-benzoxazol-5-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=C2ON=CC2=C1 TTXKLVVJWALEOY-UHFFFAOYSA-N 0.000 description 1
- DTOUUUZOYKYHEP-UHFFFAOYSA-N 1,3-bis(2-ethylhexyl)-5-methyl-1,3-diazinan-5-amine Chemical compound CCCCC(CC)CN1CN(CC(CC)CCCC)CC(C)(N)C1 DTOUUUZOYKYHEP-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 1
- 125000005895 1,4,5,7-tetrahydropyrano[3,4-b]pyrrolyl group Chemical group 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- FJANNOJSTOGZHK-UHFFFAOYSA-N 1-adamantyl carbamate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)N)C3 FJANNOJSTOGZHK-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
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- XIUQHVQLGXTGGN-UHFFFAOYSA-N 1-cyclopropylethyl carbamate Chemical compound NC(=O)OC(C)C1CC1 XIUQHVQLGXTGGN-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JXGVXCZADZNAMJ-UHFFFAOYSA-N 1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005894 1H-benzo[e][1,4]diazepinyl group Chemical group 0.000 description 1
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical class OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 1
- QPLJYAKLSCXZSF-UHFFFAOYSA-N 2,2,2-trichloroethyl carbamate Chemical compound NC(=O)OCC(Cl)(Cl)Cl QPLJYAKLSCXZSF-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical class NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- XNMOEWPBTNQAQB-UHFFFAOYSA-N 2,2,5,7,8-pentamethyl-3,4-dihydrochromene-6-sulfonamide Chemical compound C1CC(C)(C)OC2=C1C(C)=C(S(N)(=O)=O)C(C)=C2C XNMOEWPBTNQAQB-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000005899 2,3-dihydro-1H-pyrrolo[2,3-b]pyridinyl group Chemical group 0.000 description 1
- 125000005900 2,3-dihydrofuro[2,3-b]pyridinyl group Chemical group 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- PXVUDLXXKGSXHH-UHFFFAOYSA-N 2,4,6-trimethoxybenzenesulfonamide Chemical compound COC1=CC(OC)=C(S(N)(=O)=O)C(OC)=C1 PXVUDLXXKGSXHH-UHFFFAOYSA-N 0.000 description 1
- YECJUZIGFPJWGQ-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(S(N)(=O)=O)C(C)=C1 YECJUZIGFPJWGQ-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
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 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
- YJRISODHEYGPEL-UHFFFAOYSA-N 2,6-dimethoxy-4-methylbenzenesulfonamide Chemical compound COC1=CC(C)=CC(OC)=C1S(N)(=O)=O YJRISODHEYGPEL-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
- WGIMXKDCVCTHGW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCCO WGIMXKDCVCTHGW-UHFFFAOYSA-N 0.000 description 1
- DVCVYHFEWYAJCP-UHFFFAOYSA-N 2-(2-nitrophenoxy)acetamide Chemical compound NC(=O)COC1=CC=CC=C1[N+]([O-])=O DVCVYHFEWYAJCP-UHFFFAOYSA-N 0.000 description 1
- MLJSAZNRAKTZKO-UHFFFAOYSA-N 2-(2-nitrophenyl)acetamide Chemical compound NC(=O)CC1=CC=CC=C1[N+]([O-])=O MLJSAZNRAKTZKO-UHFFFAOYSA-N 0.000 description 1
- JTQUNAJHSFYGSN-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonylethyl carbamate Chemical compound CC1=CC=C(S(=O)(=O)CCOC(N)=O)C=C1 JTQUNAJHSFYGSN-UHFFFAOYSA-N 0.000 description 1
- RHTMIQNZSGHFCN-UHFFFAOYSA-N 2-(4-phenyldiazenylphenyl)propan-2-yl carbamate Chemical compound C1=CC(C(C)(OC(N)=O)C)=CC=C1N=NC1=CC=CC=C1 RHTMIQNZSGHFCN-UHFFFAOYSA-N 0.000 description 1
- FGJAPOYTPXTLPY-UHFFFAOYSA-N 2-(benzylideneamino)-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1N=CC1=CC=CC=C1 FGJAPOYTPXTLPY-UHFFFAOYSA-N 0.000 description 1
- TYYAMZMDZWXHHA-UHFFFAOYSA-N 2-(dibromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(Br)Br TYYAMZMDZWXHHA-UHFFFAOYSA-N 0.000 description 1
- JGYNXZIYXGSEJH-UHFFFAOYSA-N 2-(methylsulfanylmethoxymethyl)benzoic acid Chemical compound CSCOCC1=CC=CC=C1C(O)=O JGYNXZIYXGSEJH-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
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- QXQMENSTZKYZCE-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]acetic acid Chemical compound CCC(C)(C)C1=CC=C(OCC(O)=O)C(C(C)(C)CC)=C1 QXQMENSTZKYZCE-UHFFFAOYSA-N 0.000 description 1
- XTRFZKJEMAVUIK-UHFFFAOYSA-N 2-[2,6-dichloro-4-(2,4,4-trimethylpentan-2-yl)phenoxy]acetic acid Chemical compound CC(C)(C)CC(C)(C)C1=CC(Cl)=C(OCC(O)=O)C(Cl)=C1 XTRFZKJEMAVUIK-UHFFFAOYSA-N 0.000 description 1
- UJRMHFPTLFNSTA-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)O)C1=CC=CC=C1 UJRMHFPTLFNSTA-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
- XLMXUUQMSMKFMH-UZRURVBFSA-N 2-hydroxyethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCO XLMXUUQMSMKFMH-UZRURVBFSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 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
- UYCIUCIKUGYNBR-UHFFFAOYSA-N 2-iodoethyl carbamate Chemical compound NC(=O)OCCI UYCIUCIKUGYNBR-UHFFFAOYSA-N 0.000 description 1
- LPUAWADEOBHDIP-UHFFFAOYSA-N 2-methyl-2-(2-nitrophenoxy)propanamide Chemical compound NC(=O)C(C)(C)OC1=CC=CC=C1[N+]([O-])=O LPUAWADEOBHDIP-UHFFFAOYSA-N 0.000 description 1
- OBEJXZIQPCOKSK-UHFFFAOYSA-N 2-methyl-2-(2-phenyldiazenylphenoxy)propanamide Chemical compound NC(=O)C(C)(C)OC1=CC=CC=C1N=NC1=CC=CC=C1 OBEJXZIQPCOKSK-UHFFFAOYSA-N 0.000 description 1
- SDJNOBUNFYNROE-UHFFFAOYSA-N 2-methylbut-3-yn-2-yl carbamate Chemical compound C#CC(C)(C)OC(N)=O SDJNOBUNFYNROE-UHFFFAOYSA-N 0.000 description 1
- AUQKXXDHDKEBEY-UHFFFAOYSA-N 2-methylbutan-2-yl carbamate Chemical compound CCC(C)(C)OC(N)=O AUQKXXDHDKEBEY-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BRUZQRBVNRKLJG-UHFFFAOYSA-N 2-methylpropyl carbamate Chemical compound CC(C)COC(N)=O BRUZQRBVNRKLJG-UHFFFAOYSA-N 0.000 description 1
- OWXVECVXBTWHPP-UHFFFAOYSA-N 2-methylsulfanylethyl carbamate Chemical compound CSCCOC(N)=O OWXVECVXBTWHPP-UHFFFAOYSA-N 0.000 description 1
- IXTODZAWAAKENF-UHFFFAOYSA-N 2-methylsulfonylethyl carbamate Chemical compound CS(=O)(=O)CCOC(N)=O IXTODZAWAAKENF-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical compound NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- MUAUTBNKPSNTFM-UHFFFAOYSA-N 2-phenylethyl carbamate Chemical compound NC(=O)OCCC1=CC=CC=C1 MUAUTBNKPSNTFM-UHFFFAOYSA-N 0.000 description 1
- UCZSGRLQZLKLCQ-UHFFFAOYSA-N 2-phenylpropan-2-yl carbamate Chemical compound NC(=O)OC(C)(C)C1=CC=CC=C1 UCZSGRLQZLKLCQ-UHFFFAOYSA-N 0.000 description 1
- FCOXSVSQGYUZTB-UHFFFAOYSA-N 2-phosphanylethyl carbamate Chemical compound NC(=O)OCCP FCOXSVSQGYUZTB-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- WYECGUSLBPACPT-UHFFFAOYSA-N 2-pyridin-4-ylpropan-2-yl carbamate Chemical compound NC(=O)OC(C)(C)C1=CC=NC=C1 WYECGUSLBPACPT-UHFFFAOYSA-N 0.000 description 1
- XSXPJNJLDYOPTF-UHFFFAOYSA-N 2-trimethylsilylethoxymethanamine Chemical compound C[Si](C)(C)CCOCN XSXPJNJLDYOPTF-UHFFFAOYSA-N 0.000 description 1
- QWYTUBPAXJYCTH-UHFFFAOYSA-N 2-trimethylsilylethyl carbamate Chemical compound C[Si](C)(C)CCOC(N)=O QWYTUBPAXJYCTH-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
- KADQHJDUFKAUEB-UHFFFAOYSA-N 3-(2-nitrophenyl)propanamide Chemical compound NC(=O)CCC1=CC=CC=C1[N+]([O-])=O KADQHJDUFKAUEB-UHFFFAOYSA-N 0.000 description 1
- OEHZEBOCZWCVMK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)propanamide Chemical compound NC(=O)CCC1=CC=C(O)C=C1 OEHZEBOCZWCVMK-UHFFFAOYSA-N 0.000 description 1
- NRZLJLXOGSCRAO-UHFFFAOYSA-N 3-(4-nitrophenyl)prop-2-enyl carbamate Chemical compound NC(=O)OCC=CC1=CC=C([N+]([O-])=O)C=C1 NRZLJLXOGSCRAO-UHFFFAOYSA-N 0.000 description 1
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
- SCLGGNBFBLJQFU-UHFFFAOYSA-N 3-aminopropyl acetate Chemical compound CC(=O)OCCCN SCLGGNBFBLJQFU-UHFFFAOYSA-N 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- VYIBCOSBNVFEIW-UHFFFAOYSA-N 3-phenylpropanamide Chemical class NC(=O)CCC1=CC=CC=C1 VYIBCOSBNVFEIW-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 125000005901 4,5,6,7-tetrahydro-1H-pyrrolo[2,3-b]pyridinyl group Chemical group 0.000 description 1
- 125000005902 4,5,6,7-tetrahydrofuro[3,2-c]pyridinyl group Chemical group 0.000 description 1
- 125000005903 4,5,6,7-tetrahydrothieno[3,2-b]pyridinyl group Chemical group 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- NDRAHSMAGKWWFZ-UHFFFAOYSA-N 4-(methylsulfanylmethoxy)butanoic acid Chemical compound CSCOCCCC(O)=O NDRAHSMAGKWWFZ-UHFFFAOYSA-N 0.000 description 1
- BLEFBWAGWNSEGB-UHFFFAOYSA-N 4-[(4,8-dimethoxynaphthalen-1-yl)methyl]benzenesulfonamide Chemical compound C12=C(OC)C=CC=C2C(OC)=CC=C1CC1=CC=C(S(N)(=O)=O)C=C1 BLEFBWAGWNSEGB-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
- QPSBONMVNZJUMM-UHFFFAOYSA-N 4-chloro-2-methanimidoylphenol Chemical compound OC1=CC=C(Cl)C=C1C=N QPSBONMVNZJUMM-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- XYOXIERJKILWCG-UHFFFAOYSA-N 4-chlorobutanamide Chemical compound NC(=O)CCCCl XYOXIERJKILWCG-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- MSFQEZBRFPAFEX-UHFFFAOYSA-N 4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1 MSFQEZBRFPAFEX-UHFFFAOYSA-N 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
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 1
- LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-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
- 125000005896 5,6-dihydro-4H-furo[3,2-b]pyrrolyl group Chemical group 0.000 description 1
- 125000005898 5,7-dihydro-4H-thieno[2,3-c]pyranyl group Chemical group 0.000 description 1
- 125000005897 6,7-dihydro-5H-furo[3,2-b]pyranyl group Chemical group 0.000 description 1
- YZBKAIKDSQEETA-UHFFFAOYSA-N 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid Chemical compound C1=C(Cl)C=CC2=NC(C(=O)O)=CN21 YZBKAIKDSQEETA-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- BEFUOITXMHRTRQ-UHFFFAOYSA-N 7-chloroimidazo[1,2-a]pyridine-2-carboxylic acid Chemical compound C1=CC(Cl)=CC2=NC(C(=O)O)=CN21 BEFUOITXMHRTRQ-UHFFFAOYSA-N 0.000 description 1
- QXPJDKVEHRKBOE-UHFFFAOYSA-N 9-phenyl-9h-fluoren-1-amine Chemical compound C1=2C(N)=CC=CC=2C2=CC=CC=C2C1C1=CC=CC=C1 QXPJDKVEHRKBOE-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- GDXXYJRQFQZYNL-UHFFFAOYSA-N 9h-fluoren-1-ylmethyl carbamate Chemical compound C1C2=CC=CC=C2C2=C1C(COC(=O)N)=CC=C2 GDXXYJRQFQZYNL-UHFFFAOYSA-N 0.000 description 1
- ZZOKVYOCRSMTSS-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl carbamate Chemical compound C1=CC=C2C(COC(=O)N)C3=CC=CC=C3C2=C1 ZZOKVYOCRSMTSS-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 102100031260 Acyl-coenzyme A thioesterase THEM4 Human genes 0.000 description 1
- 240000006054 Agastache cana Species 0.000 description 1
- 235000006667 Aleurites moluccana Nutrition 0.000 description 1
- 244000136475 Aleurites moluccana Species 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 235000007689 Borago officinalis Nutrition 0.000 description 1
- 240000004355 Borago officinalis Species 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
- FSKXQQQRAARGRY-QVKFZJNVSA-N C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=O Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=O FSKXQQQRAARGRY-QVKFZJNVSA-N 0.000 description 1
- FNKPUROILDFTQA-QVKFZJNVSA-N C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=S Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H]1C[C@@H](N(C1)C(=O)OC(C)(C)C)C(N)=S FNKPUROILDFTQA-QVKFZJNVSA-N 0.000 description 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
- QAJUPJMDSJTHHR-DOTOQJQBSA-N CCOC(=O)C1=CSC(=N1)[C@H]1C[C@@H](CN1C(=O)OC(C)(C)C)OC(=O)C1=CC=CC=C1 Chemical compound CCOC(=O)C1=CSC(=N1)[C@H]1C[C@@H](CN1C(=O)OC(C)(C)C)OC(=O)C1=CC=CC=C1 QAJUPJMDSJTHHR-DOTOQJQBSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001736 Calcium glycerylphosphate Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102000005367 Carboxypeptidases Human genes 0.000 description 1
- 108010006303 Carboxypeptidases Proteins 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000005747 Carum carvi Nutrition 0.000 description 1
- 240000000467 Carum carvi Species 0.000 description 1
- 108010076119 Caseins Proteins 0.000 description 1
- 235000009024 Ceanothus sanguineus Nutrition 0.000 description 1
- PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 235000010919 Copernicia prunifera Nutrition 0.000 description 1
- 244000180278 Copernicia prunifera Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 240000009226 Corylus americana Species 0.000 description 1
- 235000001543 Corylus americana Nutrition 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 229920000858 Cyclodextrin Polymers 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
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-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
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UWTATZPHSA-M D-glycerate Chemical compound OC[C@@H](O)C([O-])=O RBNPOMFGQQGHHO-UWTATZPHSA-M 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000271571 Dromaius novaehollandiae Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- NVTRPRFAWJGJAJ-UHFFFAOYSA-L EDTA monocalcium salt Chemical compound [Ca+2].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O NVTRPRFAWJGJAJ-UHFFFAOYSA-L 0.000 description 1
- QZKRHPLGUJDVAR-UHFFFAOYSA-K EDTA trisodium salt Chemical compound [Na+].[Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O QZKRHPLGUJDVAR-UHFFFAOYSA-K 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010062466 Enzyme Precursors Proteins 0.000 description 1
- 102000010911 Enzyme Precursors Human genes 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 108010071241 Factor XIIa Proteins 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 208000003098 Ganglion Cysts Diseases 0.000 description 1
- 241000206672 Gelidium Species 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
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 108010000487 High-Molecular-Weight Kininogen Proteins 0.000 description 1
- 240000000950 Hippophae rhamnoides Species 0.000 description 1
- 235000003145 Hippophae rhamnoides Nutrition 0.000 description 1
- 101000638510 Homo sapiens Acyl-coenzyme A thioesterase THEM4 Proteins 0.000 description 1
- 241000384508 Hoplostethus atlanticus Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 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
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 235000005590 Larix decidua Nutrition 0.000 description 1
- 244000165082 Lavanda vera Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 241000408747 Lepomis gibbosus Species 0.000 description 1
- 240000003553 Leptospermum scoparium Species 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 241001072282 Limnanthes Species 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000012854 Litsea cubeba Nutrition 0.000 description 1
- 240000002262 Litsea cubeba Species 0.000 description 1
- 235000015459 Lycium barbarum Nutrition 0.000 description 1
- 241000282567 Macaca fascicularis Species 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- 206010025421 Macule Diseases 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 102000001621 Mucoproteins Human genes 0.000 description 1
- 108010093825 Mucoproteins Proteins 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 244000270834 Myristica fragrans Species 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- OVPZYECHDDCGFV-NSHDSACASA-N N[C@H](C(=O)N)CCCCNC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C Chemical compound N[C@H](C(=O)N)CCCCNC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C OVPZYECHDDCGFV-NSHDSACASA-N 0.000 description 1
- 206010029113 Neovascularisation Diseases 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 108091005461 Nucleic proteins Proteins 0.000 description 1
- 102000011931 Nucleoproteins Human genes 0.000 description 1
- 108010061100 Nucleoproteins Proteins 0.000 description 1
- 241000219925 Oenothera Species 0.000 description 1
- 235000004496 Oenothera biennis Nutrition 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 235000014643 Orbignya martiana Nutrition 0.000 description 1
- 244000021150 Orbignya martiana Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- HLCFGWHYROZGBI-JJKGCWMISA-M Potassium gluconate Chemical compound [K+].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O HLCFGWHYROZGBI-JJKGCWMISA-M 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 229910006074 SO2NH2 Inorganic materials 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- 244000044822 Simmondsia californica Species 0.000 description 1
- 235000004433 Simmondsia californica Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 208000005400 Synovial Cyst Diseases 0.000 description 1
- WPMWEFXCIYCJSA-UHFFFAOYSA-N Tetraethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCO WPMWEFXCIYCJSA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 206010067775 Upper airway obstruction Diseases 0.000 description 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 1
- 244000284012 Vetiveria zizanioides Species 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 241001135917 Vitellaria paradoxa Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- CLPYVPMXLNNKLB-UHFFFAOYSA-N [(2-nitrophenyl)-phenylmethyl] carbamate Chemical compound C=1C=CC=C([N+]([O-])=O)C=1C(OC(=O)N)C1=CC=CC=C1 CLPYVPMXLNNKLB-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- LXKLUWFIBVXFGX-QPJJXVBHSA-N [(e)-3-phenylprop-2-enyl] carbamate Chemical compound NC(=O)OC\C=C\C1=CC=CC=C1 LXKLUWFIBVXFGX-QPJJXVBHSA-N 0.000 description 1
- MQLDYIKXBMSDCL-UHFFFAOYSA-N [2,4-bis(methylsulfanyl)phenyl] carbamate Chemical compound CSC1=CC=C(OC(N)=O)C(SC)=C1 MQLDYIKXBMSDCL-UHFFFAOYSA-N 0.000 description 1
- OJUHIDQVEFLXSE-UHFFFAOYSA-N [2-(4-methoxyphenyl)-2-oxoethyl] carbamate Chemical compound COC1=CC=C(C(=O)COC(N)=O)C=C1 OJUHIDQVEFLXSE-UHFFFAOYSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XGKPLOKHSA-N [2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XGKPLOKHSA-N 0.000 description 1
- XSXGGUVGOHDUPF-UHFFFAOYSA-N [4-(carbamoyloxymethyl)phenyl]boronic acid Chemical compound NC(=O)OCC1=CC=C(B(O)O)C=C1 XSXGGUVGOHDUPF-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000005585 adamantoate group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229960002833 aflibercept Drugs 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229940024545 aluminum hydroxide Drugs 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 229960001040 ammonium chloride Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000420 anogeissus latifolia wall. gum Substances 0.000 description 1
- DQEFBVRIBYYPLE-UHFFFAOYSA-N anthracen-9-ylmethyl carbamate Chemical compound C1=CC=C2C(COC(=O)N)=C(C=CC=C3)C3=CC2=C1 DQEFBVRIBYYPLE-UHFFFAOYSA-N 0.000 description 1
- FKFZOFZWJNHJDE-UHFFFAOYSA-N anthracene-9-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N)=C(C=CC=C3)C3=CC2=C1 FKFZOFZWJNHJDE-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000000504 antifibrinolytic agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000000074 antisense oligonucleotide Substances 0.000 description 1
- 238000012230 antisense oligonucleotides Methods 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 208000025261 autosomal dominant disease Diseases 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 235000001053 badasse Nutrition 0.000 description 1
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- DUXANUSOCMOJSI-UHFFFAOYSA-N benzhydryl carbamate Chemical compound C=1C=CC=CC=1C(OC(=O)N)C1=CC=CC=C1 DUXANUSOCMOJSI-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- KVPFKMBYCSISTN-UHFFFAOYSA-N benzylsulfanylformic acid Chemical compound OC(=O)SCC1=CC=CC=C1 KVPFKMBYCSISTN-UHFFFAOYSA-N 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 229940125385 biologic drug Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 238000010352 biotechnological method Methods 0.000 description 1
- 238000001815 biotherapy Methods 0.000 description 1
- UXXXZMDJQLPQPH-UHFFFAOYSA-N bis(2-methylpropyl) carbonate Chemical compound CC(C)COC(=O)OCC(C)C UXXXZMDJQLPQPH-UHFFFAOYSA-N 0.000 description 1
- HROGQYMZWGPHIB-UHFFFAOYSA-N bis(4-methoxyphenyl)methanamine Chemical compound C1=CC(OC)=CC=C1C(N)C1=CC=C(OC)C=C1 HROGQYMZWGPHIB-UHFFFAOYSA-N 0.000 description 1
- ACBQROXDOHKANW-UHFFFAOYSA-N bis(4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACBQROXDOHKANW-UHFFFAOYSA-N 0.000 description 1
- JZUVESQYEHERMD-UHFFFAOYSA-N bis[(4-nitrophenyl)methyl] carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 JZUVESQYEHERMD-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 239000012503 blood component Substances 0.000 description 1
- 239000003152 bradykinin antagonist Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229960003168 bronopol Drugs 0.000 description 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229940067596 butylparaben Drugs 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229960002713 calcium chloride Drugs 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- 229960004256 calcium citrate Drugs 0.000 description 1
- 229960002283 calcium glubionate Drugs 0.000 description 1
- 229940078512 calcium gluceptate Drugs 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 239000004227 calcium gluconate Substances 0.000 description 1
- 235000013927 calcium gluconate Nutrition 0.000 description 1
- 229960004494 calcium gluconate Drugs 0.000 description 1
- UHHRFSOMMCWGSO-UHFFFAOYSA-L calcium glycerophosphate Chemical compound [Ca+2].OCC(CO)OP([O-])([O-])=O UHHRFSOMMCWGSO-UHFFFAOYSA-L 0.000 description 1
- 229940095618 calcium glycerophosphate Drugs 0.000 description 1
- 235000019299 calcium glycerylphosphate Nutrition 0.000 description 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 1
- 239000001527 calcium lactate Substances 0.000 description 1
- 235000011086 calcium lactate Nutrition 0.000 description 1
- 229960002401 calcium lactate Drugs 0.000 description 1
- 229940078480 calcium levulinate Drugs 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- FATUQANACHZLRT-XBQZYUPDSA-L calcium;(2r,3r,4s,5r,6r)-2,3,4,5,6,7-hexahydroxyheptanoate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C([O-])=O FATUQANACHZLRT-XBQZYUPDSA-L 0.000 description 1
- OKRXSXDSNLJCRS-NLOQLBMISA-L calcium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate;(2r,3r,4r,5r)-2,3,5,6-tetrahydroxy-4-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoate;hydrate Chemical compound O.[Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.[O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O OKRXSXDSNLJCRS-NLOQLBMISA-L 0.000 description 1
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 229960000800 cetrimonium bromide Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 229960005443 chloroxylenol Drugs 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000005747 chromanylene group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 229960002303 citric acid monohydrate Drugs 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000019516 cod Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229940013361 cresol Drugs 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-M crotonate Chemical compound C\C=C\C([O-])=O LDHQCZJRKDOVOX-NSCUHMNNSA-M 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- LWABFMLTBBNLTA-UHFFFAOYSA-N cyclobutyl carbamate Chemical compound NC(=O)OC1CCC1 LWABFMLTBBNLTA-UHFFFAOYSA-N 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- NNGAQKAUYDTUQR-UHFFFAOYSA-N cyclohexanimine Chemical compound N=C1CCCCC1 NNGAQKAUYDTUQR-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- AUELWJRRASQDKI-UHFFFAOYSA-N cyclohexyl carbamate Chemical compound NC(=O)OC1CCCCC1 AUELWJRRASQDKI-UHFFFAOYSA-N 0.000 description 1
- NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 229940086555 cyclomethicone Drugs 0.000 description 1
- 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- JMFVWNKPLURQMI-UHFFFAOYSA-N cyclopentyl carbamate Chemical compound NC(=O)OC1CCCC1 JMFVWNKPLURQMI-UHFFFAOYSA-N 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- UWYRVVJXSNXVAI-UHFFFAOYSA-N cyclopropylmethyl carbamate Chemical compound NC(=O)OCC1CC1 UWYRVVJXSNXVAI-UHFFFAOYSA-N 0.000 description 1
- 230000002380 cytological effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 description 1
- 125000005892 decahydro-1,8-naphthyridinyl group Chemical group 0.000 description 1
- 125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 description 1
- 125000005508 decahydronaphthalenyl group Chemical group 0.000 description 1
- 125000005891 decahydronaphthyridinyl group Chemical group 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 1
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 1
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
- CGMRCMMOCQYHAD-UHFFFAOYSA-J dicalcium hydroxide phosphate Chemical compound [OH-].[Ca++].[Ca++].[O-]P([O-])([O-])=O CGMRCMMOCQYHAD-UHFFFAOYSA-J 0.000 description 1
- 229940095079 dicalcium phosphate anhydrous Drugs 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
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005716 dioxanylene group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- SEBARIVPCNBHKO-UHFFFAOYSA-N dipyridin-2-ylmethyl carbamate Chemical compound C=1C=CC=NC=1C(OC(=O)N)C1=CC=CC=N1 SEBARIVPCNBHKO-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000005883 dithianyl group Chemical group 0.000 description 1
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 1
- 229960000878 docusate sodium Drugs 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 229940009662 edetate Drugs 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- UKHLURZCGAUBCQ-SSDOTTSWSA-N ethyl 2-[(2r)-pyrrolidin-2-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC([C@@H]2NCCC2)=N1 UKHLURZCGAUBCQ-SSDOTTSWSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000003722 extracellular fluid Anatomy 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 229940051306 eylea Drugs 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 229940081104 fibrinogen / thrombin Drugs 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- FGIVSGPRGVABAB-UHFFFAOYSA-N fluoren-9-ylmethyl hydrogen carbonate Chemical compound C1=CC=C2C(COC(=O)O)C3=CC=CC=C3C2=C1 FGIVSGPRGVABAB-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- RGEAONPOJJBMHO-UHFFFAOYSA-N furan-2-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=CO1 RGEAONPOJJBMHO-UHFFFAOYSA-N 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 230000009395 genetic defect Effects 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002518 glial effect Effects 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940087559 grape seed Drugs 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229960004198 guanidine Drugs 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 235000019314 gum ghatti Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000004474 heteroalkylene group Chemical group 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229960004867 hexetidine Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- HSNUXDIQZKIQRR-UHFFFAOYSA-N hydroxy-imino-bis(phenylmethoxy)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1COP(=O)(N)OCC1=CC=CC=C1 HSNUXDIQZKIQRR-UHFFFAOYSA-N 0.000 description 1
- QWMUDOFWQWBHFI-UHFFFAOYSA-N hydroxy-imino-diphenoxy-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=O)(N)OC1=CC=CC=C1 QWMUDOFWQWBHFI-UHFFFAOYSA-N 0.000 description 1
- RIGIWEGXTTUCIQ-UHFFFAOYSA-N hydroxy-imino-diphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=O)(N)C1=CC=CC=C1 RIGIWEGXTTUCIQ-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 229940113174 imidurea Drugs 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-M lactobionate Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-M 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
- 235000009606 lavandin Nutrition 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000005772 leucine Nutrition 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229960001078 lithium Drugs 0.000 description 1
- 229940076783 lucentis Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229960000816 magnesium hydroxide Drugs 0.000 description 1
- 229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- IHHCXXGJYBLXTA-LBPRGKRZSA-N methyl (2s)-2-amino-6-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]hexanoate Chemical compound COC(=O)[C@@H](N)CCCCN=C(NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C IHHCXXGJYBLXTA-LBPRGKRZSA-N 0.000 description 1
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 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
- 238000001531 micro-dissection Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 125000005893 naphthalimidyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005889 octahydrochromenyl group Chemical group 0.000 description 1
- 125000005890 octahydroisochromenyl group Chemical group 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000005882 oxadiazolinyl group Chemical group 0.000 description 1
- 125000005565 oxadiazolylene group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005880 oxathiolanyl group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 125000003551 oxepanyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 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 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-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
- PDTFCHSETJBPTR-UHFFFAOYSA-N phenylmercuric nitrate Chemical compound [O-][N+](=O)O[Hg]C1=CC=CC=C1 PDTFCHSETJBPTR-UHFFFAOYSA-N 0.000 description 1
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000008298 phosphoramidates Chemical class 0.000 description 1
- 230000000649 photocoagulation Effects 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 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
- 125000005547 pivalate group Chemical group 0.000 description 1
- 229940044519 poloxamer 188 Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229960004109 potassium acetate Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229960002816 potassium chloride Drugs 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000004224 potassium gluconate Substances 0.000 description 1
- 235000013926 potassium gluconate Nutrition 0.000 description 1
- 229960003189 potassium gluconate Drugs 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 235000020236 pumpkin seed Nutrition 0.000 description 1
- 125000005550 pyrazinylene group Chemical group 0.000 description 1
- RWUGBYOALBYTGU-UHFFFAOYSA-N pyridin-4-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=NC=C1 RWUGBYOALBYTGU-UHFFFAOYSA-N 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960003876 ranibizumab Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 230000004254 retinal expression Effects 0.000 description 1
- 230000004268 retinal thickening Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YBKWIGSMABMNJZ-UHFFFAOYSA-N s-(2,3,4,5,6-pentachlorophenyl)thiohydroxylamine Chemical compound NSC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl YBKWIGSMABMNJZ-UHFFFAOYSA-N 0.000 description 1
- RTKRAORYZUBVGQ-UHFFFAOYSA-N s-(2,4-dinitrophenyl)thiohydroxylamine Chemical compound NSC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RTKRAORYZUBVGQ-UHFFFAOYSA-N 0.000 description 1
- LOVVSIULYJABJF-UHFFFAOYSA-N s-(2-nitrophenyl)thiohydroxylamine Chemical compound NSC1=CC=CC=C1[N+]([O-])=O LOVVSIULYJABJF-UHFFFAOYSA-N 0.000 description 1
- BDEZGPKAMAVGBE-UHFFFAOYSA-N s-(3-nitropyridin-2-yl)thiohydroxylamine Chemical compound NSC1=NC=CC=C1[N+]([O-])=O BDEZGPKAMAVGBE-UHFFFAOYSA-N 0.000 description 1
- DAXSYWBYJZACTA-UHFFFAOYSA-N s-(4-methoxy-2-nitrophenyl)thiohydroxylamine Chemical compound COC1=CC=C(SN)C([N+]([O-])=O)=C1 DAXSYWBYJZACTA-UHFFFAOYSA-N 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
- MAGSSGQAJNNDLU-UHFFFAOYSA-N s-phenylthiohydroxylamine Chemical compound NSC1=CC=CC=C1 MAGSSGQAJNNDLU-UHFFFAOYSA-N 0.000 description 1
- PIDYQAYNSQSDQY-UHFFFAOYSA-N s-tritylthiohydroxylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SN)C1=CC=CC=C1 PIDYQAYNSQSDQY-UHFFFAOYSA-N 0.000 description 1
- BPELEZSCHIEMAE-UHFFFAOYSA-N salicylaldehyde imine Chemical compound OC1=CC=CC=C1C=N BPELEZSCHIEMAE-UHFFFAOYSA-N 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940037001 sodium edetate Drugs 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 210000001082 somatic cell Anatomy 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000008718 systemic inflammatory response Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-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
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 description 1
- 125000005886 tetrahydrobenzothienyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000005710 tetrahydropyranylene group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
- 125000005458 thianyl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 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
- 150000003568 thioethers Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 229960000103 thrombolytic agent 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
- 239000003106 tissue adhesive Substances 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity 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
- 238000000844 transformation Methods 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000005881 triazolinyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 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
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 108010036927 trypsin-like serine protease Proteins 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 210000005167 vascular cell Anatomy 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762541403P | 2017-08-04 | 2017-08-04 | |
| US62/541,403 | 2017-08-04 | ||
| PCT/US2018/045183 WO2019028362A1 (en) | 2017-08-04 | 2018-08-03 | INHIBITORS OF PLASMATIC KALLIKREIN AND USES THEREOF |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3070717A1 true CA3070717A1 (en) | 2019-02-07 |
Family
ID=63209746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3070717A Pending CA3070717A1 (en) | 2017-08-04 | 2018-08-03 | Inhibitors of plasma kallikrein and uses thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US11168083B2 (enExample) |
| EP (2) | EP3661922B1 (enExample) |
| JP (2) | JP7210540B2 (enExample) |
| AU (3) | AU2018311976B2 (enExample) |
| CA (1) | CA3070717A1 (enExample) |
| WO (1) | WO2019028362A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11168083B2 (en) | 2017-08-04 | 2021-11-09 | Takeda Pharmaceutical Company Limited | Inhibitors of Plasma Kallikrein and uses thereof |
| WO2019178129A1 (en) * | 2018-03-13 | 2019-09-19 | Shire Human Genetic Therapies, Inc. | Substituted imidazopyridines as inhibitors of plasma kallikrein and uses thereof |
| PT4031547T (pt) * | 2019-09-18 | 2024-08-27 | Takeda Pharmaceuticals Co | Inibidores de calicreína plasmática e utilizações dos mesmos |
| WO2021055589A1 (en) | 2019-09-18 | 2021-03-25 | Shire Human Genetic Therapies, Inc. | Heteroaryl plasma kallikrein inhibitors |
| CA3167336A1 (en) * | 2020-01-13 | 2021-07-22 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof for treating pediatric hereditary angioedema attack |
| WO2021198534A1 (en) | 2020-04-04 | 2021-10-07 | Oxurion NV | Plasma kallikrein inhibitors for use in the treatment of coronaviral disease |
| WO2023144030A1 (en) | 2022-01-31 | 2023-08-03 | Oxurion NV | Plasma kallikrein inhibitor therapy for anti-vegf sensitization |
| WO2023148016A1 (en) | 2022-02-04 | 2023-08-10 | Oxurion NV | Biomarker for plasma kallikrein inhibitor therapy response |
| WO2024059186A1 (en) * | 2022-09-15 | 2024-03-21 | Takeda Pharmaceutical Company Limited | N-((isoquinolin-6-yl)methyl)-1h-pyrazole-4-carboxamid derivatives as plasma kallikrein inhibitors for the treatment of hereditary angioedema |
| CN116063215A (zh) * | 2023-02-23 | 2023-05-05 | 南京安淮创新药物研究院有限公司 | 一种4-氨基-l-脯氨酸的合成方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA004792B1 (ru) | 1998-06-30 | 2004-08-26 | Пфайзер Продактс Инк. | Непептидные ингибиторы vla-4-зависимого клеточного связывания, полезные в лечении воспалительных, аутоиммунных и респираторных заболеваний |
| CA2634743C (en) * | 2005-12-23 | 2014-07-29 | Zealand Pharma A/S | Modified lysine-mimetic compounds |
| WO2010015090A1 (en) * | 2008-08-07 | 2010-02-11 | Aegera Therapeutics Inc. | Functionalized pyrrolidines and use thereof as iap inhibitors |
| US9079880B2 (en) * | 2010-07-07 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| EP2807157A1 (en) | 2012-01-27 | 2014-12-03 | Novartis AG | 5-membered heteroarylcarboxamide derivatives as plasma kallikrein inhibitors |
| BR112014015582A8 (pt) * | 2012-02-24 | 2017-07-04 | Hoffmann La Roche | compostos antivirais |
| GB201209138D0 (en) * | 2012-05-24 | 2012-07-04 | Ono Pharmaceutical Co | Compounds |
| JP6337750B2 (ja) * | 2013-11-22 | 2018-06-06 | 小野薬品工業株式会社 | 化合物 |
| SG11201706411YA (en) | 2015-02-27 | 2017-09-28 | Verseon Corp | Substituted pyrazole compounds as serine protease inhibitors |
| CN107614532A (zh) * | 2015-03-30 | 2018-01-19 | 戴埃克斯有限公司 | 血浆激肽释放酶抑制剂及其预防遗传性血管性水肿发作的用途 |
| WO2017001936A2 (en) * | 2015-07-01 | 2017-01-05 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| KR102696432B1 (ko) | 2015-10-01 | 2024-08-16 | 바이오크리스트파마슈티컬즈,인코포레이티드 | 인간 혈장 칼리크레인 저해제 |
| US11168083B2 (en) | 2017-08-04 | 2021-11-09 | Takeda Pharmaceutical Company Limited | Inhibitors of Plasma Kallikrein and uses thereof |
| WO2019178129A1 (en) * | 2018-03-13 | 2019-09-19 | Shire Human Genetic Therapies, Inc. | Substituted imidazopyridines as inhibitors of plasma kallikrein and uses thereof |
| PT4031547T (pt) * | 2019-09-18 | 2024-08-27 | Takeda Pharmaceuticals Co | Inibidores de calicreína plasmática e utilizações dos mesmos |
| WO2021055589A1 (en) * | 2019-09-18 | 2021-03-25 | Shire Human Genetic Therapies, Inc. | Heteroaryl plasma kallikrein inhibitors |
| DK4136091T3 (da) * | 2020-04-17 | 2025-08-18 | Takeda Pharmaceuticals Co | Former og sammensætninger af plasmakallikreinhæmmere |
-
2018
- 2018-08-03 US US16/636,518 patent/US11168083B2/en active Active
- 2018-08-03 CA CA3070717A patent/CA3070717A1/en active Pending
- 2018-08-03 JP JP2020505842A patent/JP7210540B2/ja active Active
- 2018-08-03 WO PCT/US2018/045183 patent/WO2019028362A1/en not_active Ceased
- 2018-08-03 EP EP18755681.6A patent/EP3661922B1/en active Active
- 2018-08-03 AU AU2018311976A patent/AU2018311976B2/en active Active
- 2018-08-03 EP EP24203482.5A patent/EP4494698A3/en active Pending
-
2021
- 2021-11-04 US US17/519,013 patent/US11905285B2/en active Active
-
2023
- 2023-01-11 JP JP2023002547A patent/JP7427812B2/ja active Active
- 2023-01-12 AU AU2023200156A patent/AU2023200156B2/en active Active
- 2023-12-20 US US18/390,137 patent/US20240199602A1/en active Pending
-
2025
- 2025-06-26 AU AU2025204840A patent/AU2025204840A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2023040213A (ja) | 2023-03-22 |
| AU2018311976A1 (en) | 2020-02-06 |
| US20240199602A1 (en) | 2024-06-20 |
| JP2020529998A (ja) | 2020-10-15 |
| EP4494698A2 (en) | 2025-01-22 |
| JP7210540B2 (ja) | 2023-01-23 |
| EP4494698A3 (en) | 2025-04-23 |
| AU2023200156B2 (en) | 2025-04-24 |
| AU2025204840A1 (en) | 2025-07-17 |
| AU2018311976B2 (en) | 2022-10-13 |
| EP3661922A1 (en) | 2020-06-10 |
| AU2023200156A1 (en) | 2023-02-09 |
| US11905285B2 (en) | 2024-02-20 |
| JP7427812B2 (ja) | 2024-02-05 |
| US20200239463A1 (en) | 2020-07-30 |
| EP3661922B1 (en) | 2024-10-23 |
| WO2019028362A1 (en) | 2019-02-07 |
| US20220056028A1 (en) | 2022-02-24 |
| US11168083B2 (en) | 2021-11-09 |
| JP2024045291A (ja) | 2024-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11905285B2 (en) | Inhibitors of plasma kallikrein and uses thereof | |
| EP3544970B1 (en) | Inhibitors of interleukin-1 receptor-associated kinases and uses thereof | |
| US20160046661A1 (en) | Ras inhibitors and uses thereof | |
| WO2018085247A1 (en) | Compounds for malt1 degradation | |
| EP3876939A1 (en) | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof | |
| US20220395509A1 (en) | A pyrazolopyrimidine derivative as a hck inhibitor for use in therapy, in particular myd88 mutated diseases | |
| WO2018165385A1 (en) | Inhibitors of malt1 and uses thereof | |
| US11603349B2 (en) | Anti-fibrotic compounds | |
| JP7785108B2 (ja) | 血漿カリクレインの阻害剤およびその使用 | |
| CA3218510A1 (en) | Small molecule modulators of glucocerebrosidase activity and uses thereof | |
| HK40123072A (en) | Inhibitors of plasma kallikrein and uses thereof | |
| HK40029252A (en) | Inhibitors of plasma kallikrein and uses thereof | |
| HK40029252B (en) | Inhibitors of plasma kallikrein and uses thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20220927 |
|
| EEER | Examination request |
Effective date: 20220927 |
|
| EEER | Examination request |
Effective date: 20220927 |