TW201105649A - 4-azetidinyl-1-heteroaryl-cyclohexane antagonists of CCR2 - Google Patents

Info

Publication number

TW201105649A

TW201105649A TW099111730A TW99111730A TW201105649A TW 201105649 A TW201105649 A TW 201105649A TW 099111730 A TW099111730 A TW 099111730A TW 99111730 A TW99111730 A TW 99111730A TW 201105649 A TW201105649 A TW 201105649A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

compound

substituted

optionally substituted

Prior art date

2009-04-16

Links

• Espacenet
• Global Dossier
• Discuss

• 102100031151 C-C chemokine receptor type 2 Human genes 0.000 title claims abstract 4
• 101710149815 C-C chemokine receptor type 2 Proteins 0.000 title claims abstract 4
• 239000005557 antagonist Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 274
• 238000000034 method Methods 0.000 claims abstract description 157
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
• 201000010099 disease Diseases 0.000 claims abstract description 44
• 208000006673 asthma Diseases 0.000 claims abstract description 16
• 208000008589 Obesity Diseases 0.000 claims abstract description 9
• 235000020824 obesity Nutrition 0.000 claims abstract description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 6
• -1 S02CH3 Chemical group 0.000 claims description 98
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 238000006243 chemical reaction Methods 0.000 claims description 57
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 56
• 125000004432 carbon atom Chemical group C* 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 43
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 239000012453 solvate Substances 0.000 claims description 28
• 230000005856 abnormality Effects 0.000 claims description 27
• 102100021943 C-C motif chemokine 2 Human genes 0.000 claims description 24
• 101710155857 C-C motif chemokine 2 Proteins 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 22
• 125000004076 pyridyl group Chemical group 0.000 claims description 22
• 208000024891 symptom Diseases 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
• 239000002904 solvent Substances 0.000 claims description 18
• 125000000335 thiazolyl group Chemical group 0.000 claims description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
• 150000004677 hydrates Chemical class 0.000 claims description 17
• 229940002612 prodrug Drugs 0.000 claims description 17
• 239000000651 prodrug Substances 0.000 claims description 17
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 16
• 229910052707 ruthenium Inorganic materials 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 15
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 12
• 150000002923 oximes Chemical class 0.000 claims description 12
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 12
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 11
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 206010061218 Inflammation Diseases 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 10
• 230000004054 inflammatory process Effects 0.000 claims description 10
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
• 206010012601 diabetes mellitus Diseases 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 230000001684 chronic effect Effects 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 210000004072 lung Anatomy 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 6
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 210000004369 blood Anatomy 0.000 claims description 6
• 239000008280 blood Substances 0.000 claims description 6
• 230000014509 gene expression Effects 0.000 claims description 6
• 230000002018 overexpression Effects 0.000 claims description 6
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• 201000009961 allergic asthma Diseases 0.000 claims description 5
• 206010003246 arthritis Diseases 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 208000011231 Crohn disease Diseases 0.000 claims description 4
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
• 206010036790 Productive cough Diseases 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• 208000001647 Renal Insufficiency Diseases 0.000 claims description 4
• 206010038910 Retinitis Diseases 0.000 claims description 4
• 206010052779 Transplant rejections Diseases 0.000 claims description 4
• 201000008937 atopic dermatitis Diseases 0.000 claims description 4
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 239000003638 chemical reducing agent Substances 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
• 230000003176 fibrotic effect Effects 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 208000024794 sputum Diseases 0.000 claims description 4
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
• 208000002249 Diabetes Complications Diseases 0.000 claims description 3
• 206010054044 Diabetic microangiopathy Diseases 0.000 claims description 3
• 208000017604 Hodgkin disease Diseases 0.000 claims description 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 3
• 206010022489 Insulin Resistance Diseases 0.000 claims description 3
• 125000005605 benzo group Chemical group 0.000 claims description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• 201000009101 diabetic angiopathy Diseases 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 230000004968 inflammatory condition Effects 0.000 claims description 3
• 201000006370 kidney failure Diseases 0.000 claims description 3
• 239000000463 material Substances 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 210000003802 sputum Anatomy 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 2
• 206010012655 Diabetic complications Diseases 0.000 claims description 2
• 208000031481 Pathologic Constriction Diseases 0.000 claims description 2
• 201000004681 Psoriasis Diseases 0.000 claims description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
• 206010039491 Sarcoma Diseases 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 230000002757 inflammatory effect Effects 0.000 claims description 2
• 230000000527 lymphocytic effect Effects 0.000 claims description 2
• 201000008383 nephritis Diseases 0.000 claims description 2
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
• 229910052762 osmium Inorganic materials 0.000 claims description 2
• 239000002243 precursor Substances 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 230000036262 stenosis Effects 0.000 claims description 2
• 208000037804 stenosis Diseases 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 201000008827 tuberculosis Diseases 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims 2
• SOYANKPFXHJUCE-UHFFFAOYSA-N 1,4-dioxane-2-carbaldehyde Chemical compound O=CC1COCCO1 SOYANKPFXHJUCE-UHFFFAOYSA-N 0.000 claims 1
• WTMPXTNEZVKUCY-UHFFFAOYSA-N 1h-acridin-2-one Chemical compound C1=CC=C2N=C(C=CC(=O)C3)C3=CC2=C1 WTMPXTNEZVKUCY-UHFFFAOYSA-N 0.000 claims 1
• CJKPKVLFYAXEBS-UHFFFAOYSA-N 2,3,6,7-tetrahydrooxazepine Chemical group C1CC=CCNO1 CJKPKVLFYAXEBS-UHFFFAOYSA-N 0.000 claims 1
• OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 claims 1
• 206010009900 Colitis ulcerative Diseases 0.000 claims 1
• XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims 1
• 208000017442 Retinal disease Diseases 0.000 claims 1
• 206010038923 Retinopathy Diseases 0.000 claims 1
• 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
• NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 claims 1
• 229960001541 benzthiazide Drugs 0.000 claims 1
• 210000004204 blood vessel Anatomy 0.000 claims 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
• 150000004862 dioxolanes Chemical group 0.000 claims 1
• 230000009545 invasion Effects 0.000 claims 1
• 239000008267 milk Substances 0.000 claims 1
• 210000004080 milk Anatomy 0.000 claims 1
• 235000013336 milk Nutrition 0.000 claims 1
• 230000000414 obstructive effect Effects 0.000 claims 1
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
• 239000000049 pigment Substances 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 230000002685 pulmonary effect Effects 0.000 claims 1
• 206010039083 rhinitis Diseases 0.000 claims 1
• 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 1
• ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims 1
• 230000000007 visual effect Effects 0.000 claims 1
• 208000035475 disorder Diseases 0.000 abstract description 5
• 230000000694 effects Effects 0.000 abstract description 4
• 230000002401 inhibitory effect Effects 0.000 abstract description 2
• 208000011580 syndromic disease Diseases 0.000 abstract 2
• 241000124008 Mammalia Species 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 176
• 239000007787 solid Substances 0.000 description 135
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 86
• 235000019439 ethyl acetate Nutrition 0.000 description 78
• 101150041968 CDC13 gene Proteins 0.000 description 68
• 206010057190 Respiratory tract infections Diseases 0.000 description 52
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 51
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 239000000203 mixture Substances 0.000 description 44
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 38
• 239000000243 solution Substances 0.000 description 36
• 239000002585 base Substances 0.000 description 35
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
• 238000006268 reductive amination reaction Methods 0.000 description 28
• 241001465754 Metazoa Species 0.000 description 27
• 150000002576 ketones Chemical class 0.000 description 26
• 239000003960 organic solvent Substances 0.000 description 25
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
• 238000005984 hydrogenation reaction Methods 0.000 description 22
• 238000010511 deprotection reaction Methods 0.000 description 21
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
• 150000001412 amines Chemical class 0.000 description 20
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
• 241000699670 Mus sp. Species 0.000 description 18
• 239000002253 acid Substances 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• 239000012267 brine Substances 0.000 description 14
• 238000001704 evaporation Methods 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 13
• 239000007789 gas Substances 0.000 description 13
• 239000011734 sodium Chemical group 0.000 description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 230000008020 evaporation Effects 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 239000002604 chemokine receptor CCR2 antagonist Substances 0.000 description 9
• 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 9
• 239000003814 drug Substances 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• 239000000052 vinegar Substances 0.000 description 9
• 235000021419 vinegar Nutrition 0.000 description 9
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000003981 vehicle Substances 0.000 description 8
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 7
• 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 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 206010046851 Uveitis Diseases 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 239000001257 hydrogen Substances 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• XBGXGCOLWCMVOI-UHFFFAOYSA-N 3-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(F)(F)F)=C1 XBGXGCOLWCMVOI-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 239000008103 glucose Substances 0.000 description 6
• 210000000265 leukocyte Anatomy 0.000 description 6
• 210000004698 lymphocyte Anatomy 0.000 description 6
• 210000002433 mononuclear leukocyte Anatomy 0.000 description 6
• 238000012746 preparative thin layer chromatography Methods 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• 239000002689 soil Substances 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 5
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 229910002666 PdCl2 Inorganic materials 0.000 description 5
• 229910052786 argon Inorganic materials 0.000 description 5
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
• 230000003399 chemotactic effect Effects 0.000 description 5
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 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 5
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 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 5
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
• HKDVVTLISGIPFE-UHFFFAOYSA-N 2-bromopyridin-3-amine Chemical compound NC1=CC=CN=C1Br HKDVVTLISGIPFE-UHFFFAOYSA-N 0.000 description 4
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 description 4
• 206010039085 Rhinitis allergic Diseases 0.000 description 4
• WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 4
• 230000000172 allergic effect Effects 0.000 description 4
• 201000010105 allergic rhinitis Diseases 0.000 description 4
• 238000004458 analytical method Methods 0.000 description 4
• 208000010668 atopic eczema Diseases 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 239000007822 coupling agent Substances 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 229920001971 elastomer Polymers 0.000 description 4
• 230000000670 limiting effect Effects 0.000 description 4
• 210000002540 macrophage Anatomy 0.000 description 4
• 208000028169 periodontal disease Diseases 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 229910004298 SiO 2 Inorganic materials 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 150000001336 alkenes Chemical class 0.000 description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
• 238000004820 blood count Methods 0.000 description 3
• 210000000481 breast Anatomy 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 230000012292 cell migration Effects 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 210000001072 colon Anatomy 0.000 description 3
• 238000004440 column chromatography Methods 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000010168 coupling process Methods 0.000 description 3
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
• 235000018417 cysteine Nutrition 0.000 description 3
• 230000003205 diastolic effect Effects 0.000 description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
• 239000003480 eluent Substances 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 238000003818 flash chromatography Methods 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 125000001072 heteroaryl group Chemical group 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• 229940088597 hormone Drugs 0.000 description 3
• 239000005556 hormone Substances 0.000 description 3
• 150000003840 hydrochlorides Chemical class 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 208000027866 inflammatory disease Diseases 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007928 intraperitoneal injection Substances 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 208000010125 myocardial infarction Diseases 0.000 description 3
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 239000001301 oxygen Substances 0.000 description 3
• 229910052760 oxygen Inorganic materials 0.000 description 3
• 206010034674 peritonitis Diseases 0.000 description 3
• 230000010410 reperfusion Effects 0.000 description 3
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 235000017557 sodium bicarbonate Nutrition 0.000 description 3
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• 235000017550 sodium carbonate Nutrition 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
• 229940124530 sulfonamide Drugs 0.000 description 3
• 150000003456 sulfonamides Chemical class 0.000 description 3
• 125000004434 sulfur atom Chemical group 0.000 description 3
• 150000003573 thiols Chemical group 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• JCMVPOVHKWWBAU-UHFFFAOYSA-N 1,2-dichlorohydrazine Chemical compound ClNNCl JCMVPOVHKWWBAU-UHFFFAOYSA-N 0.000 description 2
• UBXHHSQITIEELF-UHFFFAOYSA-N 2-(4-oxocyclohexyl)-1h-pyridin-4-one Chemical compound OC1=CC=NC(C2CCC(=O)CC2)=C1 UBXHHSQITIEELF-UHFFFAOYSA-N 0.000 description 2
• WEMPEMXDSUATEK-UHFFFAOYSA-N 2-bromo-6-phenylmethoxypyridine Chemical compound BrC1=CC=CC(OCC=2C=CC=CC=2)=N1 WEMPEMXDSUATEK-UHFFFAOYSA-N 0.000 description 2
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 2
• XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 2
• TXDFHVCFOQGIMV-UHFFFAOYSA-N 3-(4-oxocyclohexyl)-1h-pyridin-2-one Chemical compound OC1=NC=CC=C1C1CCC(=O)CC1 TXDFHVCFOQGIMV-UHFFFAOYSA-N 0.000 description 2
• PLPYFDYELOJEAS-UHFFFAOYSA-N 4-(6-aminopyridin-2-yl)cyclohexan-1-one Chemical compound NC1=CC=CC(C2CCC(=O)CC2)=N1 PLPYFDYELOJEAS-UHFFFAOYSA-N 0.000 description 2
• POTCZKRZTNLCAL-UHFFFAOYSA-N 4-(6-aminopyridin-3-yl)cyclohexan-1-one Chemical compound C1=NC(N)=CC=C1C1CCC(=O)CC1 POTCZKRZTNLCAL-UHFFFAOYSA-N 0.000 description 2
• NZYFNPGQFHMXCL-UHFFFAOYSA-N 4-pyrazin-2-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1=CN=CC=N1 NZYFNPGQFHMXCL-UHFFFAOYSA-N 0.000 description 2
• ZDJUNNCVIDKJAN-UHFFFAOYSA-N 5-iodo-1h-pyridin-2-one Chemical compound OC1=CC=C(I)C=N1 ZDJUNNCVIDKJAN-UHFFFAOYSA-N 0.000 description 2
• YULQWWIKHWORAH-UHFFFAOYSA-N 6-(1,4-dioxaspiro[4.5]decan-8-yl)pyridin-3-amine Chemical compound N1=CC(N)=CC=C1C1CCC2(OCCO2)CC1 YULQWWIKHWORAH-UHFFFAOYSA-N 0.000 description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
• 201000004569 Blindness Diseases 0.000 description 2
• CGZMCXMYRLKFTK-UHFFFAOYSA-N C1C(CN1)NCNC(=O)C2=CC(=CC=C2)C(F)(F)F Chemical compound C1C(CN1)NCNC(=O)C2=CC(=CC=C2)C(F)(F)F CGZMCXMYRLKFTK-UHFFFAOYSA-N 0.000 description 2
• 238000011740 C57BL/6 mouse Methods 0.000 description 2
• RCUKZGKXZGWPCB-UHFFFAOYSA-N CC(C)(S)S(=O)O Chemical compound CC(C)(S)S(=O)O RCUKZGKXZGWPCB-UHFFFAOYSA-N 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• 206010007558 Cardiac failure chronic Diseases 0.000 description 2
• 208000031229 Cardiomyopathies Diseases 0.000 description 2
• 102000019034 Chemokines Human genes 0.000 description 2
• 108010012236 Chemokines Proteins 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 208000010833 Chronic myeloid leukaemia Diseases 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
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• 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 2
• 206010018364 Glomerulonephritis Diseases 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 241000699666 Mus <mouse, genus> Species 0.000 description 2
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
• 229910002651 NO3 Inorganic materials 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 206010036346 Posterior capsule opacification Diseases 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical group C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 239000007983 Tris buffer Substances 0.000 description 2
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
• 102100040247 Tumor necrosis factor Human genes 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• 239000013566 allergen Substances 0.000 description 2
• 125000000539 amino acid group Chemical group 0.000 description 2
• 238000010171 animal model Methods 0.000 description 2
• 125000000129 anionic group Chemical group 0.000 description 2
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
• 239000000427 antigen Substances 0.000 description 2
• 108091007433 antigens Proteins 0.000 description 2
• 102000036639 antigens Human genes 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 150000001543 aryl boronic acids Chemical class 0.000 description 2
• 125000003118 aryl group Chemical group 0.000 description 2
• 150000001502 aryl halides Chemical class 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
• 230000037396 body weight Effects 0.000 description 2
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 229960005286 carbaryl Drugs 0.000 description 2
• CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
• 150000001720 carbohydrates Chemical class 0.000 description 2
• 235000011089 carbon dioxide Nutrition 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
• 125000002091 cationic group Chemical group 0.000 description 2
• 210000003679 cervix uteri Anatomy 0.000 description 2
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
• 229960001231 choline Drugs 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
• 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 235000005911 diet Nutrition 0.000 description 2
• 230000037213 diet Effects 0.000 description 2
• PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• 235000019197 fats Nutrition 0.000 description 2
• 239000012530 fluid Substances 0.000 description 2
• 239000012458 free base Substances 0.000 description 2
• 208000007565 gingivitis Diseases 0.000 description 2
• 235000009200 high fat diet Nutrition 0.000 description 2
• 229960001340 histamine Drugs 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
• 239000003112 inhibitor Substances 0.000 description 2
• 238000007912 intraperitoneal administration Methods 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• 150000002632 lipids Chemical class 0.000 description 2
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
• 230000003211 malignant effect Effects 0.000 description 2
• 210000000713 mesentery Anatomy 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• 230000011987 methylation Effects 0.000 description 2
• 238000007069 methylation reaction Methods 0.000 description 2
• 238000000386 microscopy Methods 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• 210000001616 monocyte Anatomy 0.000 description 2
• 201000000050 myeloid neoplasm Diseases 0.000 description 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• 125000002524 organometallic group Chemical group 0.000 description 2
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
• 201000007407 panuveitis Diseases 0.000 description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
• 201000001245 periodontitis Diseases 0.000 description 2
• 230000019612 pigmentation Effects 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
• 229960004919 procaine Drugs 0.000 description 2
• 210000002307 prostate Anatomy 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• 102000005962 receptors Human genes 0.000 description 2
• 108020003175 receptors Proteins 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• 208000037803 restenosis Diseases 0.000 description 2
• 239000012279 sodium borohydride Substances 0.000 description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 description 2
• VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
• 125000003003 spiro group Chemical group 0.000 description 2
• 238000010186 staining Methods 0.000 description 2
• 210000002784 stomach Anatomy 0.000 description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
• BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
• 229910021653 sulphate ion Inorganic materials 0.000 description 2
• 238000001356 surgical procedure Methods 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• 210000003932 urinary bladder Anatomy 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 229920002554 vinyl polymer Polymers 0.000 description 2
• 208000029257 vision disease Diseases 0.000 description 2
• 230000004393 visual impairment Effects 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
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• RKOUFQLNMRAACI-UHFFFAOYSA-N 1,1,1-trifluoro-2-iodoethane Chemical compound FC(F)(F)CI RKOUFQLNMRAACI-UHFFFAOYSA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• IXADHCVQNVXURI-UHFFFAOYSA-N 1,1-dichlorodecane Chemical compound CCCCCCCCCC(Cl)Cl IXADHCVQNVXURI-UHFFFAOYSA-N 0.000 description 1
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
• VKRKCBWIVLSRBJ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC21OCCO2 VKRKCBWIVLSRBJ-UHFFFAOYSA-N 0.000 description 1
• GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
• MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
• WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
• MOWJSGLSMZHLAU-UHFFFAOYSA-N 1-phenoxybutan-2-one Chemical compound CCC(=O)COC1=CC=CC=C1 MOWJSGLSMZHLAU-UHFFFAOYSA-N 0.000 description 1
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
• BOORVZVIZYSJMU-UHFFFAOYSA-N 1h-pyrazol-5-ylcarbamic acid Chemical compound OC(=O)NC1=CC=NN1 BOORVZVIZYSJMU-UHFFFAOYSA-N 0.000 description 1
• PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
• NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
• ZENKESXKWBIZCV-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxin-6-amine Chemical group O1C(F)(F)OC(F)(F)C2=CC(N)=CC=C21 ZENKESXKWBIZCV-UHFFFAOYSA-N 0.000 description 1
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
• ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
• MSRREIDXJQTTJQ-UHFFFAOYSA-N 2-(1,4-dioxaspiro[4.5]decan-8-yl)-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1C1CCC2(OCCO2)CC1 MSRREIDXJQTTJQ-UHFFFAOYSA-N 0.000 description 1
• ZKAQMNGHKHTZJU-UHFFFAOYSA-N 2-(1,4-dioxaspiro[4.5]decan-8-yl)-1h-pyridin-4-one Chemical compound OC1=CC=NC(C2CCC3(CC2)OCCO3)=C1 ZKAQMNGHKHTZJU-UHFFFAOYSA-N 0.000 description 1
• YPXOGQXZASYMFI-UHFFFAOYSA-N 2-(1,4-dioxaspiro[4.5]decan-8-yl)propanedinitrile Chemical compound C1CC(C(C#N)C#N)CCC21OCCO2 YPXOGQXZASYMFI-UHFFFAOYSA-N 0.000 description 1
• QFOHQSUZJMYQKX-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)-1H-indole Chemical compound BrC=1C=CC(=NC=1)C=1NC2=CC=CC=C2C=1 QFOHQSUZJMYQKX-UHFFFAOYSA-N 0.000 description 1
• BXJCGZLOVAWWEL-UHFFFAOYSA-N 2-(5-iodo-2-oxopyridin-1-yl)acetonitrile Chemical compound IC=1C=CC(=O)N(CC#N)C=1 BXJCGZLOVAWWEL-UHFFFAOYSA-N 0.000 description 1
• FBRJYBGLCHWYOE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(F)(F)F FBRJYBGLCHWYOE-UHFFFAOYSA-N 0.000 description 1
• UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• LACDNSNDJJPCJW-UHFFFAOYSA-N 3-(1,4-dioxaspiro[4.5]decan-8-yl)-1h-pyridin-4-one Chemical compound OC1=CC=NC=C1C1CCC2(OCCO2)CC1 LACDNSNDJJPCJW-UHFFFAOYSA-N 0.000 description 1
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• WHCXCQWDAQWHHW-UHFFFAOYSA-N 4-(4-aminopyridin-3-yl)cyclohexan-1-one Chemical compound NC1=CC=NC=C1C1CCC(=O)CC1 WHCXCQWDAQWHHW-UHFFFAOYSA-N 0.000 description 1
• VCEKBGKNNSAKGE-UHFFFAOYSA-N 4-(6-methoxypyridin-3-yl)cyclohex-3-en-1-one Chemical compound C1=NC(OC)=CC=C1C1=CCC(=O)CC1 VCEKBGKNNSAKGE-UHFFFAOYSA-N 0.000 description 1
• UPUAQYXJZIJKNW-UHFFFAOYSA-N 4-[2-(dimethylamino)pyrimidin-5-yl]cyclohexan-1-one Chemical compound C1=NC(N(C)C)=NC=C1C1CCC(=O)CC1 UPUAQYXJZIJKNW-UHFFFAOYSA-N 0.000 description 1
• DVCMSRCKPVPEPN-UHFFFAOYSA-N 4-[6-(methylamino)pyridin-2-yl]cyclohexan-1-one Chemical compound CNC1=CC=CC(C2CCC(=O)CC2)=N1 DVCMSRCKPVPEPN-UHFFFAOYSA-N 0.000 description 1
• VQZVMRZEBPGSFQ-UHFFFAOYSA-N 4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexan-1-one Chemical compound C1=NC(OC)=CC=C1C1(O)CCC(=O)CC1 VQZVMRZEBPGSFQ-UHFFFAOYSA-N 0.000 description 1
• JWIBTPMTSDSVQR-UHFFFAOYSA-N 4-iodo-2-methoxypyridine Chemical compound COC1=CC(I)=CC=N1 JWIBTPMTSDSVQR-UHFFFAOYSA-N 0.000 description 1
• QIWQJGMBIABGRX-UHFFFAOYSA-N 4-oxocyclohexane-1-carbonitrile Chemical compound O=C1CCC(C#N)CC1 QIWQJGMBIABGRX-UHFFFAOYSA-N 0.000 description 1
• WNXJNZUMRNOKNX-UHFFFAOYSA-N 5-(1,4-dioxaspiro[4.5]decan-8-yl)-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1CCC2(OCCO2)CC1 WNXJNZUMRNOKNX-UHFFFAOYSA-N 0.000 description 1
• SCZORUZPHBSQIP-UHFFFAOYSA-N 5-(1,4-dioxaspiro[4.5]decan-8-yl)-n,n-dimethylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=NC=C1C1CCC2(OCCO2)CC1 SCZORUZPHBSQIP-UHFFFAOYSA-N 0.000 description 1
• MDQXGHBCDCOOSM-UHFFFAOYSA-N 5-bromopyridin-3-amine Chemical compound NC1=CN=CC(Br)=C1 MDQXGHBCDCOOSM-UHFFFAOYSA-N 0.000 description 1
• QTZHDCRKNXCGPV-UHFFFAOYSA-N 5-iodo-2-propan-2-yloxyacridine Chemical compound CC(C)OC1=CC2=C(C=C1)N=C3C(=C2)C=CC=C3I QTZHDCRKNXCGPV-UHFFFAOYSA-N 0.000 description 1
• 101150039504 6 gene Proteins 0.000 description 1
• JXZFNSAICOUNFX-UHFFFAOYSA-N 6-(1,4-dioxaspiro[4.5]decan-8-yl)-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(C2CCC3(CC2)OCCO3)=N1 JXZFNSAICOUNFX-UHFFFAOYSA-N 0.000 description 1
• LLHWSBXZXJXVPL-UHFFFAOYSA-N 6-(2-methylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound CC1=CC=CC=C1C1=NC(N)=NC(N)=N1 LLHWSBXZXJXVPL-UHFFFAOYSA-N 0.000 description 1
• PTEFNEALEPSHLC-UHFFFAOYSA-N 6-bromopyridin-3-ol Chemical compound OC1=CC=C(Br)N=C1 PTEFNEALEPSHLC-UHFFFAOYSA-N 0.000 description 1
• GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
• JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
• 206010027654 Allergic conditions Diseases 0.000 description 1
• 206010002091 Anaesthesia Diseases 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 206010003497 Asphyxia Diseases 0.000 description 1
• 102100022718 Atypical chemokine receptor 2 Human genes 0.000 description 1
• 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
• 208000023275 Autoimmune disease Diseases 0.000 description 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 206010005186 Blindness unilateral Diseases 0.000 description 1
• 208000019838 Blood disease Diseases 0.000 description 1
• 208000031648 Body Weight Changes Diseases 0.000 description 1
• 239000004135 Bone phosphate Substances 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• 244000140786 Brassica hirta Species 0.000 description 1
• 235000011371 Brassica hirta Nutrition 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• QWSZKQFTJKOHFO-UHFFFAOYSA-N C(C1=CC=CC=C1)C1=C(C(=O)N)C=CC=C1C(F)(F)F Chemical compound C(C1=CC=CC=C1)C1=C(C(=O)N)C=CC=C1C(F)(F)F QWSZKQFTJKOHFO-UHFFFAOYSA-N 0.000 description 1
• CMCQZHBZLISNNH-UHFFFAOYSA-N C(CCCCCCCCC)C(C)CC(C)(CCCCCCCCCC)CCCCCCCCCC Chemical group C(CCCCCCCCC)C(C)CC(C)(CCCCCCCCCC)CCCCCCCCCC CMCQZHBZLISNNH-UHFFFAOYSA-N 0.000 description 1
• RYFSOVQANMUFSI-UHFFFAOYSA-N C(CCCCCCCCC)OC1=NC=CC=C1B(O)O Chemical compound C(CCCCCCCCC)OC1=NC=CC=C1B(O)O RYFSOVQANMUFSI-UHFFFAOYSA-N 0.000 description 1
• 102100023702 C-C motif chemokine 13 Human genes 0.000 description 1
• WUWYBBGJBJWBJK-UHFFFAOYSA-N C1CCOC1.CCN(CC)CC.OC(=O)C(F)(F)F Chemical compound C1CCOC1.CCN(CC)CC.OC(=O)C(F)(F)F WUWYBBGJBJWBJK-UHFFFAOYSA-N 0.000 description 1
• NBTIPXWOPCPOQA-UHFFFAOYSA-N CC1=CC(C(CC2)CCC2N(C2)CC2NC(CNC(c2cc(C(F)(F)F)ccc2)=O)=O)=CN(C)C1=O Chemical compound CC1=CC(C(CC2)CCC2N(C2)CC2NC(CNC(c2cc(C(F)(F)F)ccc2)=O)=O)=CN(C)C1=O NBTIPXWOPCPOQA-UHFFFAOYSA-N 0.000 description 1
• ISGFQCCFGVMSRF-UHFFFAOYSA-N CC1=CC(C(CC2)CCC2N(C2)CC2NC(CNC(c2cc(C(F)(F)F)ccc2)=O)=O)=CNC1=O Chemical compound CC1=CC(C(CC2)CCC2N(C2)CC2NC(CNC(c2cc(C(F)(F)F)ccc2)=O)=O)=CNC1=O ISGFQCCFGVMSRF-UHFFFAOYSA-N 0.000 description 1
• AXOAQOSDEFKOTF-UHFFFAOYSA-N CCCCCCCCCCCCCC1=CC(=O)C=CC1=O Chemical compound CCCCCCCCCCCCCC1=CC(=O)C=CC1=O AXOAQOSDEFKOTF-UHFFFAOYSA-N 0.000 description 1
• KSSSNDQYWQTJPB-UHFFFAOYSA-N CCCCCCCCCCOC1=NC=C(C=C1)C2(CCC(=O)CC2)O Chemical compound CCCCCCCCCCOC1=NC=C(C=C1)C2(CCC(=O)CC2)O KSSSNDQYWQTJPB-UHFFFAOYSA-N 0.000 description 1
• GWMKMMXMYQEXMI-UHFFFAOYSA-N CCNCC.F.F.F.S Chemical compound CCNCC.F.F.F.S GWMKMMXMYQEXMI-UHFFFAOYSA-N 0.000 description 1
• 108010017312 CCR2 Receptors Proteins 0.000 description 1
• 102000004497 CCR2 Receptors Human genes 0.000 description 1
• MEMRXUCNUKAUBV-UHFFFAOYSA-N CN(C=CC(C(CC1)CCC1N(C1)CC1NC(CNC(c1cccc(C(F)(F)F)c1)=O)=O)=C1)C1=O Chemical compound CN(C=CC(C(CC1)CCC1N(C1)CC1NC(CNC(c1cccc(C(F)(F)F)c1)=O)=O)=C1)C1=O MEMRXUCNUKAUBV-UHFFFAOYSA-N 0.000 description 1
• UGMMDBWAUPTALK-UHFFFAOYSA-N CN(C=CC=C1C(CC2)CCC2N(C2)CC2NC(CNC(c2cc(C(F)(F)F)ccc2)=O)=O)C1=O Chemical compound CN(C=CC=C1C(CC2)CCC2N(C2)CC2NC(CNC(c2cc(C(F)(F)F)ccc2)=O)=O)C1=O UGMMDBWAUPTALK-UHFFFAOYSA-N 0.000 description 1
• 101100008046 Caenorhabditis elegans cut-2 gene Proteins 0.000 description 1
• 101100504320 Caenorhabditis elegans mcp-1 gene Proteins 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 241000238366 Cephalopoda Species 0.000 description 1
• 229910052684 Cerium Inorganic materials 0.000 description 1
• 102000009410 Chemokine receptor Human genes 0.000 description 1
• 108050000299 Chemokine receptor Proteins 0.000 description 1
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
• 235000001258 Cinchona calisaya Nutrition 0.000 description 1
• 206010010356 Congenital anomaly Diseases 0.000 description 1
• 206010010741 Conjunctivitis Diseases 0.000 description 1
• 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• 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 1
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
• 206010012689 Diabetic retinopathy Diseases 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• 206010058314 Dysplasia Diseases 0.000 description 1
• 102000002322 Egg Proteins Human genes 0.000 description 1
• 108010000912 Egg Proteins Proteins 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• ZAKFGYRAKXPGNH-UHFFFAOYSA-M F[S+](F)F.[F-] Chemical compound F[S+](F)F.[F-] ZAKFGYRAKXPGNH-UHFFFAOYSA-M 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
• 102000012153 HLA-B27 Antigen Human genes 0.000 description 1
• 108010061486 HLA-B27 Antigen Proteins 0.000 description 1
• 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 1
• 101000777599 Homo sapiens C-C chemokine receptor type 2 Proteins 0.000 description 1
• 101000716070 Homo sapiens C-C chemokine receptor type 9 Proteins 0.000 description 1
• 101000897480 Homo sapiens C-C motif chemokine 2 Proteins 0.000 description 1
• 101100382872 Homo sapiens CCL13 gene Proteins 0.000 description 1
• 101000976075 Homo sapiens Insulin Proteins 0.000 description 1
• 101001013648 Homo sapiens Methionine synthase Proteins 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-O Htris Chemical compound OCC([NH3+])(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-O 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 206010020649 Hyperkeratosis Diseases 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
• 108090001007 Interleukin-8 Proteins 0.000 description 1
• 108010063738 Interleukins Proteins 0.000 description 1
• 102000015696 Interleukins Human genes 0.000 description 1
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
• 229930194542 Keto Natural products 0.000 description 1
• 239000005909 Kieselgur Substances 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
• FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 208000019693 Lung disease Diseases 0.000 description 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
• 229940123313 MCP-1 antagonist Drugs 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 108700018351 Major Histocompatibility Complex Proteins 0.000 description 1
• 102000002274 Matrix Metalloproteinases Human genes 0.000 description 1
• 108010000684 Matrix Metalloproteinases Proteins 0.000 description 1
• 206010027468 Metastases to spine Diseases 0.000 description 1
• 229920003091 Methocel™ Polymers 0.000 description 1
• UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
• 208000034578 Multiple myelomas Diseases 0.000 description 1
• 101000777597 Mus musculus C-C chemokine receptor type 2 Proteins 0.000 description 1
• 102000003896 Myeloperoxidases Human genes 0.000 description 1
• 108090000235 Myeloperoxidases Proteins 0.000 description 1
• 208000009525 Myocarditis Diseases 0.000 description 1
• 201000002481 Myositis Diseases 0.000 description 1
• 239000007832 Na2SO4 Substances 0.000 description 1
• VDULJRHAYRRBKK-DRQUAOQDSA-N Nc1n[o]c(N)c1[C@H](CC1)CC[C@H]1N(C1)CC1NC(CNC(c1cc(C(F)(F)F)ccc1)=O)=O Chemical compound Nc1n[o]c(N)c1[C@H](CC1)CC[C@H]1N(C1)CC1NC(CNC(c1cc(C(F)(F)F)ccc1)=O)=O VDULJRHAYRRBKK-DRQUAOQDSA-N 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• YQYPVLSRAKQNJF-UHFFFAOYSA-N O=C(CNC(c1cc(C(F)(F)F)ccc1)=O)NC(C1)CN1C(CC1)CCC1C(N1)=CC=CC1=O Chemical compound O=C(CNC(c1cc(C(F)(F)F)ccc1)=O)NC(C1)CN1C(CC1)CCC1C(N1)=CC=CC1=O YQYPVLSRAKQNJF-UHFFFAOYSA-N 0.000 description 1
• 206010061876 Obstruction Diseases 0.000 description 1
• 241001420836 Ophthalmitis Species 0.000 description 1
• 244000131316 Panax pseudoginseng Species 0.000 description 1
• 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
• 235000003140 Panax quinquefolius Nutrition 0.000 description 1
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 1
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
• 102000015439 Phospholipases Human genes 0.000 description 1
• 108010064785 Phospholipases Proteins 0.000 description 1
• 108091000080 Phosphotransferase Proteins 0.000 description 1
• 102000001253 Protein Kinase Human genes 0.000 description 1
• 239000012980 RPMI-1640 medium Substances 0.000 description 1
• 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
• NNHHMVNDTZNBRG-UHFFFAOYSA-N SSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS Chemical compound SSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS NNHHMVNDTZNBRG-UHFFFAOYSA-N 0.000 description 1
• ALLNCHFLYGZHEC-UHFFFAOYSA-N SSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS Chemical compound SSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS ALLNCHFLYGZHEC-UHFFFAOYSA-N 0.000 description 1
• 206010039424 Salivary hypersecretion Diseases 0.000 description 1
• 208000034189 Sclerosis Diseases 0.000 description 1
• 201000010001 Silicosis Diseases 0.000 description 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 229930182558 Sterol Natural products 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 239000005864 Sulphur Substances 0.000 description 1
• 101000588258 Taenia solium Paramyosin Proteins 0.000 description 1
• 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 1
• 201000005485 Toxoplasmosis Diseases 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
• 206010054094 Tumour necrosis Diseases 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 206010052568 Urticaria chronic Diseases 0.000 description 1
• 206010057469 Vascular stenosis Diseases 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• 206010047571 Visual impairment Diseases 0.000 description 1
• 235000009754 Vitis X bourquina Nutrition 0.000 description 1
• 235000012333 Vitis X labruscana Nutrition 0.000 description 1
• 240000006365 Vitis vinifera Species 0.000 description 1
• 235000014787 Vitis vinifera Nutrition 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• YKNZTUQUXUXTLE-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(C(F)(F)F)=C1 YKNZTUQUXUXTLE-UHFFFAOYSA-N 0.000 description 1
• 210000000683 abdominal cavity Anatomy 0.000 description 1
• PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
• 239000003929 acidic solution Substances 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 150000001447 alkali salts Chemical class 0.000 description 1
• 239000012670 alkaline solution Substances 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 150000008051 alkyl sulfates Chemical class 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 208000002205 allergic conjunctivitis Diseases 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 230000037005 anaesthesia Effects 0.000 description 1
• 230000003444 anaesthetic effect Effects 0.000 description 1
• 210000003423 ankle Anatomy 0.000 description 1
• 125000005577 anthracene group Chemical group 0.000 description 1
• PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
• 150000004056 anthraquinones Chemical class 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 206010003230 arteritis Diseases 0.000 description 1
• 125000001769 aryl amino group Chemical group 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• 208000024998 atopic conjunctivitis Diseases 0.000 description 1
• HEWRTOMNMWSWOD-UHFFFAOYSA-N azetidin-3-yl hydrogen carbonate Chemical compound OC(=O)OC1CNC1 HEWRTOMNMWSWOD-UHFFFAOYSA-N 0.000 description 1
• 125000003943 azolyl group Chemical group 0.000 description 1
• 210000003912 basophilic leucocyte Anatomy 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000005872 benzooxazolyl group Chemical group 0.000 description 1
• RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
• 239000012965 benzophenone Substances 0.000 description 1
• DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 230000002146 bilateral effect Effects 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 238000004166 bioassay Methods 0.000 description 1
• 230000004579 body weight change Effects 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• 239000001273 butane Substances 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229960005069 calcium Drugs 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-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
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 229940095643 calcium hydroxide Drugs 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
• 150000001718 carbodiimides Chemical class 0.000 description 1
• 229910002091 carbon monoxide Inorganic materials 0.000 description 1
• 210000004413 cardiac myocyte Anatomy 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
• 239000002975 chemoattractant Substances 0.000 description 1
• 239000005482 chemotactic factor Substances 0.000 description 1
• 230000035605 chemotaxis Effects 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
• 229940005991 chloric acid Drugs 0.000 description 1
• 210000001612 chondrocyte Anatomy 0.000 description 1
• 208000037976 chronic inflammation Diseases 0.000 description 1
• 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
• 208000024376 chronic urticaria Diseases 0.000 description 1
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Chemical group C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
• 150000001860 citric acid derivatives Chemical class 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
• 229960004126 codeine Drugs 0.000 description 1
• 230000000295 complement effect Effects 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
• 150000001924 cycloalkanes Chemical group 0.000 description 1
• 229940097362 cyclodextrins Drugs 0.000 description 1
• AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 235000013365 dairy product Nutrition 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 239000012024 dehydrating agents‎ Substances 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
• 229960003957 dexamethasone Drugs 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• 150000004985 diamines Chemical class 0.000 description 1
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
• ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• DXVWRJRZCMCNEU-UHFFFAOYSA-N dimercaptoamine Chemical compound SNS DXVWRJRZCMCNEU-UHFFFAOYSA-N 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
• 229960002986 dinoprostone Drugs 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• 125000000597 dioxinyl group Chemical group 0.000 description 1
• IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
• 229960002768 dipyridamole Drugs 0.000 description 1
• 239000002612 dispersion medium Substances 0.000 description 1
• 206010013781 dry mouth Diseases 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 239000000428 dust Substances 0.000 description 1
• 229940009662 edetate Drugs 0.000 description 1
• 210000001671 embryonic stem cell Anatomy 0.000 description 1
• 238000005265 energy consumption Methods 0.000 description 1
• 210000003979 eosinophil Anatomy 0.000 description 1
• 230000002327 eosinophilic effect Effects 0.000 description 1
• 229950000206 estolate Drugs 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• VDDXQSUSMHZCLS-UHFFFAOYSA-N ethenyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC=C VDDXQSUSMHZCLS-UHFFFAOYSA-N 0.000 description 1
• FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 230000006203 ethylation Effects 0.000 description 1
• 238000006200 ethylation reaction Methods 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000004744 fabric Substances 0.000 description 1
• 239000012091 fetal bovine serum Substances 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
• 239000012025 fluorinating agent Substances 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 235000012631 food intake Nutrition 0.000 description 1
• 239000012634 fragment Substances 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 208000024693 gingival disease Diseases 0.000 description 1
• 235000008434 ginseng Nutrition 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 238000007446 glucose tolerance test Methods 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• 229910052737 gold Inorganic materials 0.000 description 1
• 239000010931 gold Substances 0.000 description 1
• 239000001963 growth medium Substances 0.000 description 1
• DXTIKTAIYCJTII-UHFFFAOYSA-N guanidine acetate Chemical compound CC([O-])=O.NC([NH3+])=N DXTIKTAIYCJTII-UHFFFAOYSA-N 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 208000014951 hematologic disease Diseases 0.000 description 1
• 208000018706 hematopoietic system disease Diseases 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 102000046768 human CCL2 Human genes 0.000 description 1
• 102000043994 human CCR2 Human genes 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• DQKGOGJIOHUEGK-UHFFFAOYSA-M hydron;2-hydroxyethyl(trimethyl)azanium;carbonate Chemical class OC([O-])=O.C[N+](C)(C)CCO DQKGOGJIOHUEGK-UHFFFAOYSA-M 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 238000003384 imaging method Methods 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 210000002865 immune cell Anatomy 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 230000028709 inflammatory response Effects 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 102000002467 interleukin receptors Human genes 0.000 description 1
• 108010093036 interleukin receptors Proteins 0.000 description 1
• 229940047122 interleukins Drugs 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 229940001447 lactate Drugs 0.000 description 1
• 150000003893 lactate salts Chemical class 0.000 description 1
• 229940099584 lactobionate Drugs 0.000 description 1
• JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=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-N 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 238000004020 luminiscence type Methods 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
• IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
• 230000005415 magnetization Effects 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 150000002688 maleic acid derivatives Chemical class 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 101150018062 mcp4 gene Proteins 0.000 description 1
• 235000012054 meals Nutrition 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 210000004379 membrane Anatomy 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 229960001428 mercaptopurine Drugs 0.000 description 1
• 210000003584 mesangial cell Anatomy 0.000 description 1
• 238000003328 mesylation reaction Methods 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• GRFNBEZIAWKNCO-UHFFFAOYSA-N mhp Natural products OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 1
• 230000000813 microbial effect Effects 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 238000010232 migration assay Methods 0.000 description 1
• 239000003595 mist Substances 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 238000012544 monitoring process Methods 0.000 description 1
• 210000005087 mononuclear cell Anatomy 0.000 description 1
• 229960005127 montelukast Drugs 0.000 description 1
• 238000010172 mouse model Methods 0.000 description 1
• 210000004877 mucosa Anatomy 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 230000002107 myocardial effect Effects 0.000 description 1
• ONIGMBFFLWOJBC-UHFFFAOYSA-N n-(1,4-dioxaspiro[4.5]decan-8-ylidene)-2-methylpropane-2-sulfinamide Chemical compound C1CC(=NS(=O)C(C)(C)C)CCC21OCCO2 ONIGMBFFLWOJBC-UHFFFAOYSA-N 0.000 description 1
• PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 210000002850 nasal mucosa Anatomy 0.000 description 1
• 239000006199 nebulizer Substances 0.000 description 1
• 208000018309 neoplasm of pericardium Diseases 0.000 description 1
• 210000000440 neutrophil Anatomy 0.000 description 1
• 150000002823 nitrates Chemical class 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• 150000003891 oxalate salts Chemical class 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• 208000010403 panophthalmitis Diseases 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• 238000005192 partition Methods 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 235000019371 penicillin G benzathine Nutrition 0.000 description 1
• 201000010236 pericardium cancer Diseases 0.000 description 1
• 239000003330 peritoneal dialysis fluid Substances 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 102000020233 phosphotransferase Human genes 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical group [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 238000004237 preparative chromatography Methods 0.000 description 1
• 230000000770 proinflammatory effect Effects 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
• XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
• 108060006633 protein kinase Proteins 0.000 description 1
• 235000018102 proteins Nutrition 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 230000001047 pyretic effect Effects 0.000 description 1
• AQIDWPCFDNAMQW-UHFFFAOYSA-N pyridin-3-ol Chemical compound OC1=C=NC=C[CH]1 AQIDWPCFDNAMQW-UHFFFAOYSA-N 0.000 description 1
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 238000005956 quaternization reaction Methods 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• 230000000171 quenching effect Effects 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
• 229960000948 quinine Drugs 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 238000001525 receptor binding assay Methods 0.000 description 1
• 230000007115 recruitment Effects 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 230000008929 regeneration Effects 0.000 description 1
• 238000011069 regeneration method Methods 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 230000000717 retained effect Effects 0.000 description 1
• 238000003757 reverse transcription PCR Methods 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 229910052703 rhodium Inorganic materials 0.000 description 1
• 239000010948 rhodium Substances 0.000 description 1
• 208000007442 rickets Diseases 0.000 description 1
• 238000005096 rolling process Methods 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 210000003296 saliva Anatomy 0.000 description 1
• 208000026451 salivation Diseases 0.000 description 1
• 201000000306 sarcoidosis Diseases 0.000 description 1
• 238000007632 sclerotherapy Methods 0.000 description 1
• 230000001932 seasonal effect Effects 0.000 description 1
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 230000011664 signaling Effects 0.000 description 1
• 229910052709 silver Inorganic materials 0.000 description 1
• 239000004332 silver Substances 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
• CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 229940083542 sodium Drugs 0.000 description 1
• 235000015424 sodium Nutrition 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 229940001593 sodium carbonate Drugs 0.000 description 1
• KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
• 229910001948 sodium oxide Inorganic materials 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 210000000278 spinal cord Anatomy 0.000 description 1
• 210000000952 spleen Anatomy 0.000 description 1
• 201000005671 spondyloarthropathy Diseases 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 150000003432 sterols Chemical class 0.000 description 1
• 235000003702 sterols Nutrition 0.000 description 1
• 239000004575 stone Substances 0.000 description 1
• 239000010907 stover Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 150000003890 succinate salts Chemical class 0.000 description 1
• 239000001384 succinic acid Substances 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 230000020382 suppression by virus of host antigen processing and presentation of peptide antigen via MHC class I Effects 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000001648 tannin Substances 0.000 description 1
• 235000018553 tannin Nutrition 0.000 description 1
• 229920001864 tannin Polymers 0.000 description 1
• 230000008685 targeting Effects 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 150000003892 tartrate salts Chemical class 0.000 description 1
• KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
• WPGLRFGDZJSQGI-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(N)C1 WPGLRFGDZJSQGI-UHFFFAOYSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
• YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 239000003451 thiazide diuretic agent Substances 0.000 description 1
• 238000004809 thin layer chromatography Methods 0.000 description 1
• RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
• ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical class CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
• IKRJDNRUEIWOIB-UHFFFAOYSA-N trifluoromethylhydrazine Chemical compound NNC(F)(F)F IKRJDNRUEIWOIB-UHFFFAOYSA-N 0.000 description 1
• NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 150000003648 triterpenes Chemical group 0.000 description 1
• 230000002485 urinary effect Effects 0.000 description 1
• 210000003556 vascular endothelial cell Anatomy 0.000 description 1
• 210000003462 vein Anatomy 0.000 description 1
• 230000004580 weight loss Effects 0.000 description 1
• 229940075420 xanthine Drugs 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1