CA2445923A1 - Arylsulfonamide ethers, and methods of use thereof - Google Patents
Arylsulfonamide ethers, and methods of use thereof Download PDFInfo
- Publication number
- CA2445923A1 CA2445923A1 CA002445923A CA2445923A CA2445923A1 CA 2445923 A1 CA2445923 A1 CA 2445923A1 CA 002445923 A CA002445923 A CA 002445923A CA 2445923 A CA2445923 A CA 2445923A CA 2445923 A1 CA2445923 A1 CA 2445923A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- mmol
- methyl
- ethoxy
- butyl ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 Arylsulfonamide ethers Chemical class 0.000 title claims abstract description 167
- 238000000034 method Methods 0.000 title claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 234
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
- 102000004190 Enzymes Human genes 0.000 claims abstract description 23
- 108090000790 Enzymes Proteins 0.000 claims abstract description 23
- 102000000589 Interleukin-1 Human genes 0.000 claims abstract description 23
- 108010002352 Interleukin-1 Proteins 0.000 claims abstract description 23
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
- 208000004429 Bacillary Dysentery Diseases 0.000 claims abstract description 9
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 9
- 206010040550 Shigella infections Diseases 0.000 claims abstract description 9
- 230000036303 septic shock Effects 0.000 claims abstract description 9
- 201000005113 shigellosis Diseases 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 166
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 35
- 150000007942 carboxylates Chemical class 0.000 claims description 34
- 125000003282 alkyl amino group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 150000001408 amides Chemical class 0.000 claims description 28
- 125000005518 carboxamido group Chemical group 0.000 claims description 27
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000004442 acylamino group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 8
- 102000015696 Interleukins Human genes 0.000 claims description 8
- 108010063738 Interleukins Proteins 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 7
- ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical compound NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 241000283073 Equus caballus Species 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 241000288906 Primates Species 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 241000282465 Canis Species 0.000 claims description 4
- 241000282324 Felis Species 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 abstract description 12
- 208000006011 Stroke Diseases 0.000 abstract description 9
- 230000006378 damage Effects 0.000 abstract description 5
- 208000027418 Wounds and injury Diseases 0.000 abstract description 4
- 208000014674 injury Diseases 0.000 abstract description 4
- 102000005927 Cysteine Proteases Human genes 0.000 abstract description 3
- 108010005843 Cysteine Proteases Proteins 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 346
- 239000000243 solution Substances 0.000 description 177
- 238000006243 chemical reaction Methods 0.000 description 176
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 165
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 160
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 147
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 133
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
- 235000019439 ethyl acetate Nutrition 0.000 description 131
- 239000007787 solid Substances 0.000 description 103
- 239000002904 solvent Substances 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
- 229910001868 water Inorganic materials 0.000 description 82
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 80
- 229940093499 ethyl acetate Drugs 0.000 description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 72
- 238000004458 analytical method Methods 0.000 description 69
- 238000005481 NMR spectroscopy Methods 0.000 description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 65
- 239000011541 reaction mixture Substances 0.000 description 62
- 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 60
- 230000002829 reductive effect Effects 0.000 description 59
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 58
- 239000012267 brine Substances 0.000 description 57
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 52
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 51
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 46
- 230000015572 biosynthetic process Effects 0.000 description 46
- 238000003786 synthesis reaction Methods 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 40
- 238000009472 formulation Methods 0.000 description 38
- 239000000047 product Substances 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- 239000002253 acid Substances 0.000 description 36
- 239000003921 oil Substances 0.000 description 35
- 101150041968 CDC13 gene Proteins 0.000 description 34
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 34
- 239000000377 silicon dioxide Substances 0.000 description 34
- 239000012043 crude product Substances 0.000 description 33
- 239000003153 chemical reaction reagent Substances 0.000 description 32
- 239000000284 extract Substances 0.000 description 32
- 239000006260 foam Substances 0.000 description 32
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 32
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 29
- 150000001299 aldehydes Chemical class 0.000 description 28
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- 238000003818 flash chromatography Methods 0.000 description 26
- 239000012280 lithium aluminium hydride Substances 0.000 description 26
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 22
- 239000002585 base Substances 0.000 description 22
- 230000005764 inhibitory process Effects 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 239000012445 acidic reagent Substances 0.000 description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- 229960004132 diethyl ether Drugs 0.000 description 16
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000007868 Raney catalyst Substances 0.000 description 15
- 229910000564 Raney nickel Inorganic materials 0.000 description 15
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 239000012230 colorless oil Substances 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 238000010790 dilution Methods 0.000 description 12
- 239000012895 dilution Substances 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 239000003638 chemical reducing agent Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910010084 LiAlH4 Inorganic materials 0.000 description 10
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000012467 final product Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 9
- 239000003880 polar aprotic solvent Substances 0.000 description 9
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- CJFSLXUSMNTOJH-UHFFFAOYSA-N 2-quinolin-5-ylethanol Chemical compound C1=CC=C2C(CCO)=CC=CC2=N1 CJFSLXUSMNTOJH-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 239000006071 cream Substances 0.000 description 8
- 239000012954 diazonium Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 239000002516 radical scavenger Substances 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- XLBHXAPKYJTOJQ-UHFFFAOYSA-N 2-phenylmethoxybenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1OCC1=CC=CC=C1 XLBHXAPKYJTOJQ-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- SCVFNOOEMBXGCQ-UHFFFAOYSA-N methyl 4-chlorosulfonyl-3-phenylmethoxybenzoate Chemical compound COC(=O)C1=CC=C(S(Cl)(=O)=O)C(OCC=2C=CC=CC=2)=C1 SCVFNOOEMBXGCQ-UHFFFAOYSA-N 0.000 description 7
- 239000002674 ointment Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 235000019502 Orange oil Nutrition 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 239000011260 aqueous acid Substances 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000006193 diazotization reaction Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
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- WLBPXYYLSJLKFH-HNNXBMFYSA-N tert-butyl (3s)-3-[(4-acetamido-2-hydroxyphenyl)sulfonylamino]-4,4-diethoxybutanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(OCC)OCC)NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1O WLBPXYYLSJLKFH-HNNXBMFYSA-N 0.000 description 1
- NRHCDWWDUALEOU-NSHDSACASA-N tert-butyl (3s)-3-[(4-acetamido-2-hydroxyphenyl)sulfonylamino]-4-amino-4-oxobutanoate Chemical compound CC(=O)NC1=CC=C(S(=O)(=O)N[C@@H](CC(=O)OC(C)(C)C)C(N)=O)C(O)=C1 NRHCDWWDUALEOU-NSHDSACASA-N 0.000 description 1
- QJBFKSLAXSSCIB-FQEVSTJZSA-N tert-butyl (3s)-3-[[2-(2-isoquinolin-4-ylethoxy)phenyl]sulfonylamino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C=O)NS(=O)(=O)C1=CC=CC=C1OCCC1=CN=CC2=CC=CC=C12 QJBFKSLAXSSCIB-FQEVSTJZSA-N 0.000 description 1
- PPGDIVFWERZVFL-FQEVSTJZSA-N tert-butyl (3s)-3-[[4-(dimethylamino)-2-(2-quinolin-5-ylethoxy)phenyl]sulfonylamino]-4-oxobutanoate Chemical compound CN(C)C1=CC=C(S(=O)(=O)N[C@@H](CC(=O)OC(C)(C)C)C=O)C(OCCC=2C3=CC=CN=C3C=CC=2)=C1 PPGDIVFWERZVFL-FQEVSTJZSA-N 0.000 description 1
- IAWUPRXPGFKQNW-NRFANRHFSA-N tert-butyl (3s)-3-[[4-acetamido-2-(2-quinolin-5-ylethoxy)phenyl]sulfonylamino]-3-cyanopropanoate Chemical compound CC(=O)NC1=CC=C(S(=O)(=O)N[C@@H](CC(=O)OC(C)(C)C)C#N)C(OCCC=2C3=CC=CN=C3C=CC=2)=C1 IAWUPRXPGFKQNW-NRFANRHFSA-N 0.000 description 1
- WLMJHMHWWYDODU-QFIPXVFZSA-N tert-butyl (3s)-3-[[4-acetamido-2-(2-quinolin-5-ylethoxy)phenyl]sulfonylamino]-4-amino-4-oxobutanoate Chemical compound CC(=O)NC1=CC=C(S(=O)(=O)N[C@@H](CC(=O)OC(C)(C)C)C(N)=O)C(OCCC=2C3=CC=CN=C3C=CC=2)=C1 WLMJHMHWWYDODU-QFIPXVFZSA-N 0.000 description 1
- AFIJRJGHZPBKPD-INIZCTEOSA-N tert-butyl (3s)-4,4-diethoxy-3-(phenylmethoxycarbonylamino)butanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(OCC)OCC)NC(=O)OCC1=CC=CC=C1 AFIJRJGHZPBKPD-INIZCTEOSA-N 0.000 description 1
- VXVJVFUBAJEVOA-ZDUSSCGKSA-N tert-butyl (3s)-4,4-diethoxy-3-[(2-hydroxyphenyl)sulfonylamino]butanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(OCC)OCC)NS(=O)(=O)C1=CC=CC=C1O VXVJVFUBAJEVOA-ZDUSSCGKSA-N 0.000 description 1
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- AZUXCDPAXAHXCQ-SFHVURJKSA-N tert-butyl (3s)-4-[methoxy(methyl)amino]-3-[(4-nitro-2-phenylmethoxyphenyl)sulfonylamino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(=O)N(C)OC)NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 AZUXCDPAXAHXCQ-SFHVURJKSA-N 0.000 description 1
- NJFCFDZRUCHHEE-MHZLTWQESA-N tert-butyl (3s)-4-[methoxy(methyl)amino]-3-[[2-(2-naphthalen-1-ylethoxy)-4-pyrrolidin-1-ylphenyl]sulfonylamino]-4-oxobutanoate Chemical compound C1=C(OCCC=2C3=CC=CC=C3C=CC=2)C(S(=O)(=O)N[C@@H](CC(=O)OC(C)(C)C)C(=O)N(C)OC)=CC=C1N1CCCC1 NJFCFDZRUCHHEE-MHZLTWQESA-N 0.000 description 1
- WWYDTGAIEAZSKR-QBGQUKIHSA-N tert-butyl (3s)-4-[methoxy(methyl)amino]-3-[[2-[1-(2-methylnaphthalen-1-yl)propan-2-yloxy]phenyl]sulfonylamino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(=O)N(C)OC)NS(=O)(=O)C1=CC=CC=C1OC(C)CC1=C(C)C=CC2=CC=CC=C12 WWYDTGAIEAZSKR-QBGQUKIHSA-N 0.000 description 1
- KPWRDUVESIMHLE-INIZCTEOSA-N tert-butyl (3s)-4-amino-3-[(4-amino-2-phenylmethoxyphenyl)sulfonylamino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(N)=O)NS(=O)(=O)C1=CC=C(N)C=C1OCC1=CC=CC=C1 KPWRDUVESIMHLE-INIZCTEOSA-N 0.000 description 1
- LQWVVPZNNNSFKR-INIZCTEOSA-N tert-butyl (3s)-4-amino-3-[(4-nitro-2-phenylmethoxyphenyl)sulfonylamino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(N)=O)NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 LQWVVPZNNNSFKR-INIZCTEOSA-N 0.000 description 1
- WQRUFMHFJXVZMZ-UHFFFAOYSA-N tert-butyl 2-oxobutanoate Chemical compound CCC(=O)C(=O)OC(C)(C)C WQRUFMHFJXVZMZ-UHFFFAOYSA-N 0.000 description 1
- PUABYKZHEQKVGT-UHFFFAOYSA-N tert-butyl 3-[(4-acetamido-2-hydroxyphenyl)sulfonylamino]-4-[methoxy(methyl)amino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)CC(C(=O)N(C)OC)NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1O PUABYKZHEQKVGT-UHFFFAOYSA-N 0.000 description 1
- POSZVASGEQUDEJ-UHFFFAOYSA-N tert-butyl 3-[[2-[2-[2-[2-(dimethylamino)ethoxy]naphthalen-1-yl]ethoxy]phenyl]sulfonylamino]-4-[methoxy(methyl)amino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)CC(C(=O)N(C)OC)NS(=O)(=O)C1=CC=CC=C1OCCC1=C(OCCN(C)C)C=CC2=CC=CC=C12 POSZVASGEQUDEJ-UHFFFAOYSA-N 0.000 description 1
- YVJFEWNQGLWINZ-UHFFFAOYSA-N tert-butyl 3-[[2-[2-[2-[2-(dimethylamino)ethoxy]naphthalen-1-yl]ethoxy]phenyl]sulfonylamino]-4-oxobutanoate Chemical compound CN(C)CCOC1=CC=C2C=CC=CC2=C1CCOC1=CC=CC=C1S(=O)(=O)NC(CC(=O)OC(C)(C)C)C=O YVJFEWNQGLWINZ-UHFFFAOYSA-N 0.000 description 1
- YSVBQMBWYGRRMH-UHFFFAOYSA-N tert-butyl 3-[[4-(methylcarbamothioylamino)-2-(2-quinolin-5-ylethoxy)phenyl]sulfonylamino]-4-oxobutanoate Chemical compound CNC(=S)NC1=CC=C(S(=O)(=O)NC(CC(=O)OC(C)(C)C)C=O)C(OCCC=2C3=CC=CN=C3C=CC=2)=C1 YSVBQMBWYGRRMH-UHFFFAOYSA-N 0.000 description 1
- ZDTVGNYZMHFNIS-UHFFFAOYSA-N tert-butyl 3-[[4-[2-(dimethylamino)ethylcarbamoyl]-2-hydroxyphenyl]sulfonylamino]-4,4-diethoxybutanoate Chemical compound CC(C)(C)OC(=O)CC(C(OCC)OCC)NS(=O)(=O)C1=CC=C(C(=O)NCCN(C)C)C=C1O ZDTVGNYZMHFNIS-UHFFFAOYSA-N 0.000 description 1
- YPFFPWZOKVRLSU-UHFFFAOYSA-N tert-butyl 3-[[4-acetamido-2-(2-naphthalen-1-ylethoxy)phenyl]sulfonylamino]-4-oxobutanoate Chemical compound CC(=O)NC1=CC=C(S(=O)(=O)NC(CC(=O)OC(C)(C)C)C=O)C(OCCC=2C3=CC=CC=C3C=CC=2)=C1 YPFFPWZOKVRLSU-UHFFFAOYSA-N 0.000 description 1
- ZLTMKXDUNRLOMD-UHFFFAOYSA-N tert-butyl 3-[[4-acetamido-2-(2-quinolin-5-ylethoxy)phenyl]sulfonylamino]-4-[methoxy(methyl)amino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)CC(C(=O)N(C)OC)NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1OCCC1=CC=CC2=NC=CC=C12 ZLTMKXDUNRLOMD-UHFFFAOYSA-N 0.000 description 1
- SPSJSCVGUWVZBA-UHFFFAOYSA-N tert-butyl 3-[[4-amino-2-(2-naphthalen-1-ylethoxy)phenyl]sulfonylamino]-4-[methoxy(methyl)amino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)CC(C(=O)N(C)OC)NS(=O)(=O)C1=CC=C(N)C=C1OCCC1=CC=CC2=CC=CC=C12 SPSJSCVGUWVZBA-UHFFFAOYSA-N 0.000 description 1
- PJEZFSXUSKJJKY-UHFFFAOYSA-N tert-butyl 3-amino-4,4-diethoxybutanoate Chemical compound CCOC(OCC)C(N)CC(=O)OC(C)(C)C PJEZFSXUSKJJKY-UHFFFAOYSA-N 0.000 description 1
- MVCSHSGILZHKEM-UHFFFAOYSA-N tert-butyl 4-(methylamino)-3-[(4-nitro-2-phenylmethoxyphenyl)sulfonylamino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)CC(C(=O)NC)NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 MVCSHSGILZHKEM-UHFFFAOYSA-N 0.000 description 1
- REDHLDAUEDQNTP-UHFFFAOYSA-N tert-butyl 4-[methoxy(methyl)amino]-3-[[2-(2-naphthalen-1-ylethoxy)-4-nitrophenyl]sulfonylamino]-4-oxobutanoate Chemical compound CC(C)(C)OC(=O)CC(C(=O)N(C)OC)NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1OCCC1=CC=CC2=CC=CC=C12 REDHLDAUEDQNTP-UHFFFAOYSA-N 0.000 description 1
- WFPAIHVCLZLRLP-UHFFFAOYSA-N tert-butyl 4-[methoxy(methyl)amino]-4-oxobutanoate Chemical compound CON(C)C(=O)CCC(=O)OC(C)(C)C WFPAIHVCLZLRLP-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/42—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/47—Y being a hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28995001P | 2001-05-10 | 2001-05-10 | |
| US60/289,950 | 2001-05-10 | ||
| PCT/US2002/015002 WO2002089749A2 (en) | 2001-05-10 | 2002-05-10 | Arylsulfonamide ethers, and methods of use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2445923A1 true CA2445923A1 (en) | 2002-11-14 |
Family
ID=23113875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002445923A Abandoned CA2445923A1 (en) | 2001-05-10 | 2002-05-10 | Arylsulfonamide ethers, and methods of use thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6875765B2 (enExample) |
| EP (1) | EP1392280A4 (enExample) |
| JP (1) | JP2005500996A (enExample) |
| AU (1) | AU2002305552A1 (enExample) |
| CA (1) | CA2445923A1 (enExample) |
| MX (1) | MXPA03010179A (enExample) |
| WO (1) | WO2002089749A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8420699B1 (en) | 2002-06-19 | 2013-04-16 | Irvine L. Dubow | Composition and methods of treatment using deionized and ozonated solution |
| US7897642B1 (en) * | 2002-06-19 | 2011-03-01 | Dr. Irvine Dubow | Compositions and methods for dry eye syndrome |
| US20050011464A1 (en) * | 2003-07-14 | 2005-01-20 | The Chinese University Of Hong Kong | Additive composition for feeding aquaculture animals and feed containing the same |
| WO2005117846A2 (en) | 2004-05-27 | 2005-12-15 | Vertex Pharmaceuticals Incorporated | Ice inhibitors for the treatment of autoinflammatory diseases |
| CA2559047A1 (en) | 2004-03-11 | 2005-09-29 | Elan Pharmaceuticals, Inc. | N-substituted benzene sulfonamides |
| US20060128696A1 (en) | 2004-05-15 | 2006-06-15 | Annamaria Vezzani | Treating seizures using ice inhibitors |
| ES2552733T3 (es) | 2007-11-16 | 2015-12-01 | Rigel Pharmaceuticals, Inc. | Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos |
| US8129390B2 (en) | 2007-12-12 | 2012-03-06 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds and methods for using the same |
| US20090185995A1 (en) * | 2008-01-18 | 2009-07-23 | Stacy Vochecowicz | Lubricious, non-tacky personal lubricant |
| US9969751B2 (en) * | 2009-06-10 | 2018-05-15 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds |
| WO2011094426A1 (en) | 2010-01-29 | 2011-08-04 | The United State Of America, As Represented By The Secretary, Department Of Health & Human Services | Caspase inhibitors |
| JP6006908B2 (ja) | 2010-11-05 | 2016-10-12 | ブランダイス ユニバーシティBrandeis University | Ice阻害化合物およびその使用 |
| WO2013080156A1 (en) | 2011-11-30 | 2013-06-06 | Actelion Pharmaceuticals Ltd | 3,7-disubstituted octahydro-2h-pyrido[4,3-e][1,3]oxazin-2-one antibiotics |
| CN109879817B (zh) * | 2019-03-19 | 2020-10-02 | 扬州大学 | 甲基二磺隆的制备方法 |
| CN118191186B (zh) * | 2024-05-16 | 2024-07-23 | 西南林业大学 | 一种水体中磺胺类抗生素的提取方法及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69735230D1 (de) * | 1996-10-11 | 2006-04-20 | Warner Lambert Company Llc Mor | Sulfonamid-substituierte asparaginsäuren als inhibitoren von interleukin-1beta-konvertierenden enzymen |
-
2002
- 2002-05-10 AU AU2002305552A patent/AU2002305552A1/en not_active Abandoned
- 2002-05-10 EP EP02734382A patent/EP1392280A4/en not_active Withdrawn
- 2002-05-10 MX MXPA03010179A patent/MXPA03010179A/es unknown
- 2002-05-10 CA CA002445923A patent/CA2445923A1/en not_active Abandoned
- 2002-05-10 JP JP2002586888A patent/JP2005500996A/ja active Pending
- 2002-05-10 WO PCT/US2002/015002 patent/WO2002089749A2/en not_active Ceased
- 2002-05-10 US US10/143,675 patent/US6875765B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6875765B2 (en) | 2005-04-05 |
| WO2002089749A3 (en) | 2003-02-27 |
| WO2002089749A2 (en) | 2002-11-14 |
| EP1392280A2 (en) | 2004-03-03 |
| MXPA03010179A (es) | 2004-03-16 |
| EP1392280A4 (en) | 2005-11-30 |
| US20030096826A1 (en) | 2003-05-22 |
| AU2002305552A1 (en) | 2002-11-18 |
| JP2005500996A (ja) | 2005-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |