SG177634A1 - Spirocyclic amide derivatives - Google Patents

Info

Publication number

SG177634A1

SG177634A1 SG2012002358A SG2012002358A SG177634A1 SG 177634 A1 SG177634 A1 SG 177634A1 SG 2012002358 A SG2012002358 A SG 2012002358A SG 2012002358 A SG2012002358 A SG 2012002358A SG 177634 A1 SG177634 A1 SG 177634A1

Authority

SG

Singapore

Prior art keywords

alkyl

optionally substituted

compound

formula

ring

Prior art date

2009-07-31

Links

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• Global Dossier
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• 150000001408 amides Chemical class 0.000 title abstract description 3
• 238000000034 method Methods 0.000 claims abstract description 54
• 238000002360 preparation method Methods 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 230000008569 process Effects 0.000 claims abstract description 12
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 11
• 230000027455 binding Effects 0.000 claims abstract description 6
• 238000004519 manufacturing process Methods 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 301
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 109
• 125000000217 alkyl group Chemical group 0.000 claims description 104
• 125000003118 aryl group Chemical group 0.000 claims description 93
• 239000002904 solvent Substances 0.000 claims description 93
• 150000003839 salts Chemical class 0.000 claims description 65
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 239000001257 hydrogen Substances 0.000 claims description 59
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
• 229910052736 halogen Inorganic materials 0.000 claims description 55
• 150000002367 halogens Chemical class 0.000 claims description 55
• 229910052760 oxygen Inorganic materials 0.000 claims description 51
• 239000000460 chlorine Substances 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 229910052720 vanadium Inorganic materials 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 229910052796 boron Inorganic materials 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 125000006413 ring segment Chemical group 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 239000003638 chemical reducing agent Substances 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
• 150000001721 carbon Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 239000005864 Sulphur Chemical group 0.000 claims description 6
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 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 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 229930192474 thiophene Natural products 0.000 claims description 6
• 239000002671 adjuvant Substances 0.000 claims description 5
• 125000002723 alicyclic group Chemical group 0.000 claims description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 125000001931 aliphatic group Chemical group 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 230000002441 reversible effect Effects 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• 208000027771 Obstructive airways disease Diseases 0.000 claims description 2
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• 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 claims 1
• -1 their use in therapy Substances 0.000 abstract description 125
• 239000000543 intermediate Substances 0.000 abstract description 81
• 102000015005 beta-adrenergic receptor activity proteins Human genes 0.000 abstract 1
• 108040006818 beta-adrenergic receptor activity proteins Proteins 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 329
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 258
• 239000000243 solution Substances 0.000 description 209
• 239000000203 mixture Substances 0.000 description 176
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 175
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 160
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
• 238000005481 NMR spectroscopy Methods 0.000 description 140
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 116
• 235000019439 ethyl acetate Nutrition 0.000 description 109
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 100
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 93
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 82
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 79
• 239000012267 brine Substances 0.000 description 75
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 68
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 63
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 59
• 238000006243 chemical reaction Methods 0.000 description 55
• 239000003921 oil Substances 0.000 description 55
• 235000019198 oils Nutrition 0.000 description 55
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 54
• 239000000377 silicon dioxide Substances 0.000 description 52
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 50
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
• 239000011541 reaction mixture Substances 0.000 description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 42
• 239000000047 product Substances 0.000 description 42
• 230000002829 reductive effect Effects 0.000 description 42
• 239000007787 solid Substances 0.000 description 41
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 39
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 37
• 150000001412 amines Chemical class 0.000 description 36
• 238000004587 chromatography analysis Methods 0.000 description 36
• 239000000725 suspension Substances 0.000 description 35
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 32
• 239000003112 inhibitor Substances 0.000 description 31
• 239000012074 organic phase Substances 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 29
• 229910052938 sodium sulfate Inorganic materials 0.000 description 29
• 235000011152 sodium sulphate Nutrition 0.000 description 29
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 28
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 150000002431 hydrogen Chemical class 0.000 description 27
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 27
• 238000007792 addition Methods 0.000 description 25
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
• 239000012043 crude product Substances 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 23
• 239000003795 chemical substances by application Substances 0.000 description 21
• 238000011282 treatment Methods 0.000 description 20
• 239000003960 organic solvent Substances 0.000 description 19
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• 238000010992 reflux Methods 0.000 description 18
• 239000007821 HATU Substances 0.000 description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
• 125000006239 protecting group Chemical group 0.000 description 17
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 17
• 238000010828 elution Methods 0.000 description 16
• 239000008346 aqueous phase Substances 0.000 description 15
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
• 235000019260 propionic acid Nutrition 0.000 description 15
• 238000010898 silica gel chromatography Methods 0.000 description 15
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 239000005457 ice water Substances 0.000 description 14
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• 239000000284 extract Substances 0.000 description 13
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 13
• 238000005406 washing Methods 0.000 description 13
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
• 235000011114 ammonium hydroxide Nutrition 0.000 description 12
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 12
• 239000010410 layer Substances 0.000 description 12
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 10
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 10
• 230000001154 acute effect Effects 0.000 description 10
• 239000005557 antagonist Substances 0.000 description 10
• 238000013459 approach Methods 0.000 description 10
• MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 10
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
• 229910000024 caesium carbonate Inorganic materials 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• 238000004128 high performance liquid chromatography Methods 0.000 description 10
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
• JOZZAIIGWFLONA-RXMQYKEDSA-N (2r)-3-methylbutan-2-amine Chemical compound CC(C)[C@@H](C)N JOZZAIIGWFLONA-RXMQYKEDSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 230000003213 activating effect Effects 0.000 description 9
• NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
• YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 8
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 239000003054 catalyst Substances 0.000 description 8
• 238000003818 flash chromatography Methods 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 8
• JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 208000035475 disorder Diseases 0.000 description 7
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 7
• 229910003446 platinum oxide Inorganic materials 0.000 description 7
• 229940044551 receptor antagonist Drugs 0.000 description 7
• 239000002464 receptor antagonist Substances 0.000 description 7
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
• 239000003643 water by type Substances 0.000 description 7
• RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
• KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
• 102000004127 Cytokines Human genes 0.000 description 6
• 108090000695 Cytokines Proteins 0.000 description 6
• 239000001828 Gelatine Substances 0.000 description 6
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
• 206010028980 Neoplasm Diseases 0.000 description 6
• 208000002193 Pain Diseases 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 239000000556 agonist Substances 0.000 description 6
• 208000006673 asthma Diseases 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• 229960004132 diethyl ether Drugs 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 229920000159 gelatin Polymers 0.000 description 6
• 235000019322 gelatine Nutrition 0.000 description 6
• 150000004820 halides Chemical class 0.000 description 6
• 239000012035 limiting reagent Substances 0.000 description 6
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 206010039083 rhinitis Diseases 0.000 description 6
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 230000001684 chronic effect Effects 0.000 description 5
• UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• 208000015181 infectious disease Diseases 0.000 description 5
• 150000002617 leukotrienes Chemical class 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 210000004072 lung Anatomy 0.000 description 5
• 238000002953 preparative HPLC Methods 0.000 description 5
• 210000003491 skin Anatomy 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 208000011580 syndromic disease Diseases 0.000 description 5
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