CA2394037C - Nouveaux derives de benzene sulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents
Nouveaux derives de benzene sulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Download PDFInfo
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- CA2394037C CA2394037C CA002394037A CA2394037A CA2394037C CA 2394037 C CA2394037 C CA 2394037C CA 002394037 A CA002394037 A CA 002394037A CA 2394037 A CA2394037 A CA 2394037A CA 2394037 C CA2394037 C CA 2394037C
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- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000008331 benzenesulfonamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- -1 arylcarbonylalkyl Chemical group 0.000 claims abstract description 36
- 125000005843 halogen group Chemical group 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 10
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract description 8
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 8
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 8
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims abstract description 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims abstract description 8
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
- 208000006673 asthma Diseases 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 6
- 208000037997 venous disease Diseases 0.000 claims abstract description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims abstract description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 5
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims abstract description 5
- 125000005368 heteroarylthio group Chemical group 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 5
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 5
- 208000014181 Bronchial disease Diseases 0.000 claims description 5
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- 208000003782 Raynaud disease Diseases 0.000 claims description 5
- 208000012322 Raynaud phenomenon Diseases 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- 239000002464 receptor antagonist Substances 0.000 claims description 3
- 229940044551 receptor antagonist Drugs 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- RWMLYDOJPQMAMS-UHFFFAOYSA-N 3-[3-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-5-[2-[(4-chlorophenyl)sulfonylamino]ethyl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(CCN3CCN(CC3)C=3C4=CC=CC=C4SN=3)C2=CC=1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 RWMLYDOJPQMAMS-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 206010061216 Infarction Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001735 carboxylic acids Chemical group 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 abstract 1
- 239000000047 product Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 238000004452 microanalysis Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XGLLXYJZWWJEGV-UHFFFAOYSA-N (4-fluorophenyl)-piperidin-4-ylmethanone;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1=CC(F)=CC=C1C(=O)C1CCNCC1 XGLLXYJZWWJEGV-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 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 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KRDOFMHJLWKXIU-UHFFFAOYSA-N ID11614 Chemical compound C1CNCCN1C1=NSC2=CC=CC=C12 KRDOFMHJLWKXIU-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 101150100032 Tbxa2r gene Proteins 0.000 description 1
- 108090000300 Thromboxane Receptors Proteins 0.000 description 1
- 102000003938 Thromboxane Receptors Human genes 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PPDJNZTUDFPAHX-UHFFFAOYSA-N benzyltrimethylammonium dichloroiodate Chemical compound Cl[I-]Cl.C[N+](C)(C)CC1=CC=CC=C1 PPDJNZTUDFPAHX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- RDPLOLUNEKBWBR-UHFFFAOYSA-L magnesium;sodium;sulfate Chemical compound [Na+].[Mg+2].[O-]S([O-])(=O)=O RDPLOLUNEKBWBR-UHFFFAOYSA-L 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- UEXHUIGOSQMRCS-UHFFFAOYSA-N n-[2-(4-amino-3-iodophenyl)ethyl]-4-chlorobenzenesulfonamide Chemical compound C1=C(I)C(N)=CC=C1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 UEXHUIGOSQMRCS-UHFFFAOYSA-N 0.000 description 1
- IOMCRGBUOOKIAJ-UHFFFAOYSA-N n-[2-[3-(2-bromoethyl)-1h-indol-5-yl]ethyl]-4-chlorobenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NCCC1=CC=C(NC=C2CCBr)C2=C1 IOMCRGBUOOKIAJ-UHFFFAOYSA-N 0.000 description 1
- VWVDMZUCKNAAAT-UHFFFAOYSA-N n-[2-[3-(3-bromopropyl)-1h-indol-5-yl]ethyl]-4-chlorobenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NCCC1=CC=C(NC=C2CCCBr)C2=C1 VWVDMZUCKNAAAT-UHFFFAOYSA-N 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000002840 nitric oxide donor Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000010118 platelet activation Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000000328 pro-aggregatory effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- CHCWSBPYUGPTGD-UHFFFAOYSA-N trimethyl(5-trimethylsilyloxypent-1-ynyl)silane Chemical compound C[Si](C)(C)OCCCC#C[Si](C)(C)C CHCWSBPYUGPTGD-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/12—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 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
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0109338A FR2827287B1 (fr) | 2001-07-13 | 2001-07-13 | Nouveaux derives de benzene sulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR01.09338 | 2001-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2394037A1 CA2394037A1 (fr) | 2003-01-13 |
| CA2394037C true CA2394037C (fr) | 2008-04-29 |
Family
ID=8865461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002394037A Expired - Fee Related CA2394037C (fr) | 2001-07-13 | 2002-07-15 | Nouveaux derives de benzene sulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6589956B2 (en:Method) |
| EP (1) | EP1275644A1 (en:Method) |
| JP (1) | JP4138382B2 (en:Method) |
| KR (1) | KR100498864B1 (en:Method) |
| CN (1) | CN1168715C (en:Method) |
| AR (1) | AR036340A1 (en:Method) |
| AU (1) | AU2002300093B2 (en:Method) |
| BR (1) | BR0202674A (en:Method) |
| CA (1) | CA2394037C (en:Method) |
| EA (1) | EA005403B1 (en:Method) |
| FR (1) | FR2827287B1 (en:Method) |
| HU (1) | HUP0202286A2 (en:Method) |
| MX (1) | MXPA02006852A (en:Method) |
| NO (1) | NO323868B1 (en:Method) |
| NZ (1) | NZ520140A (en:Method) |
| PL (1) | PL354948A1 (en:Method) |
| ZA (1) | ZA200205598B (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007023882A1 (ja) * | 2005-08-26 | 2007-03-01 | Shionogi & Co., Ltd. | Ｐｐａｒアゴニスト活性を有する誘導体 |
| WO2014047427A2 (en) | 2012-09-21 | 2014-03-27 | Vanderbilt University | Substituted benzofuran, benzothiophene and indole mcl-1 inhibitors |
| EP3038618B1 (en) | 2013-08-28 | 2020-10-14 | Vanderbilt University | Substituted indole mcl-1 inhibitors |
| CA2943815C (en) | 2014-03-27 | 2023-04-04 | Vanderbilt University | Substituted indole mcl-1 inhibitors |
| US9949965B2 (en) | 2014-10-17 | 2018-04-24 | Vanderbilt University | Tricyclic indole Mcl-1 inhibitors and uses thereof |
| CA3016182C (en) | 2016-03-04 | 2024-02-27 | Vanderbilt Universtiy | Substituted indole mcl-1 inhibitors |
| US20220213079A1 (en) * | 2019-12-24 | 2022-07-07 | Sumitomo Dainippon Pharma Co., Ltd. | Aliphatic acid amide derivative |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468882A (en) * | 1966-10-07 | 1969-09-23 | Sterling Drug Inc | Phenylhydrazone derivatives as intermediates for preparing indoles |
| GB8419575D0 (en) * | 1984-08-01 | 1984-09-05 | Glaxo Group Ltd | Chemical compounds |
| KR940007458B1 (ko) * | 1991-11-21 | 1994-08-18 | 주식회사 금성사 | 박막 트랜지스터 제조 방법 |
| TW219358B (en:Method) * | 1991-12-20 | 1994-01-21 | Hokuriku Pharmaceutical | |
| EP0675109A1 (en) * | 1992-12-21 | 1995-10-04 | Taisho Pharmaceutical Co. Ltd | N-substituted indole derivative |
| GB9317764D0 (en) * | 1993-08-26 | 1993-10-13 | Pfizer Ltd | Therapeutic compound |
| FR2712591B1 (fr) * | 1993-11-19 | 1996-02-09 | Pf Medicament | Nouvelles arylpipérazines dérivées d'indole, leur préparation et leur utilisation thérapeutique. |
| EP0751126A4 (en) * | 1995-01-06 | 1998-05-13 | Toray Industries | BENZOCONDENSE HETEROCYCLIC DERIVATIVE AND ITS USE |
| AU7319096A (en) * | 1995-11-02 | 1997-05-22 | Merck Sharp & Dohme Limited | Bicyclic heteroaryl-alkylene-(homo)piperazinones and thione analogues thereof, their preparation and their use as selective agonists of 5-ht1-like receptors |
| GB9523243D0 (en) * | 1995-11-14 | 1996-01-17 | Merck Sharp & Dohme | Therapeutic agents |
| GB9523250D0 (en) * | 1995-11-14 | 1996-01-17 | Merck Sharp & Dohme | Therapeutic agents |
-
2001
- 2001-07-13 FR FR0109338A patent/FR2827287B1/fr not_active Expired - Fee Related
-
2002
- 2002-07-08 PL PL02354948A patent/PL354948A1/xx not_active Application Discontinuation
- 2002-07-10 BR BR0202674-0A patent/BR0202674A/pt not_active IP Right Cessation
- 2002-07-10 JP JP2002200910A patent/JP4138382B2/ja not_active Expired - Fee Related
- 2002-07-11 MX MXPA02006852A patent/MXPA02006852A/es active IP Right Grant
- 2002-07-11 EP EP02291746A patent/EP1275644A1/fr not_active Withdrawn
- 2002-07-12 ZA ZA200205598A patent/ZA200205598B/xx unknown
- 2002-07-12 AU AU2002300093A patent/AU2002300093B2/en not_active Ceased
- 2002-07-12 EA EA200200665A patent/EA005403B1/ru not_active IP Right Cessation
- 2002-07-12 NZ NZ520140A patent/NZ520140A/en unknown
- 2002-07-12 NO NO20023389A patent/NO323868B1/no not_active IP Right Cessation
- 2002-07-12 AR ARP020102608A patent/AR036340A1/es not_active Application Discontinuation
- 2002-07-12 HU HU0202286A patent/HUP0202286A2/hu unknown
- 2002-07-12 US US10/195,031 patent/US6589956B2/en not_active Expired - Fee Related
- 2002-07-13 KR KR10-2002-0040945A patent/KR100498864B1/ko not_active Expired - Fee Related
- 2002-07-15 CN CNB021241619A patent/CN1168715C/zh not_active Expired - Fee Related
- 2002-07-15 CA CA002394037A patent/CA2394037C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002300093B2 (en) | 2007-07-12 |
| NZ520140A (en) | 2003-09-26 |
| HK1050681A1 (en) | 2003-07-04 |
| AR036340A1 (es) | 2004-09-01 |
| US6589956B2 (en) | 2003-07-08 |
| HU0202286D0 (en:Method) | 2002-09-28 |
| JP2003064055A (ja) | 2003-03-05 |
| HUP0202286A2 (hu) | 2003-08-28 |
| KR100498864B1 (ko) | 2005-07-04 |
| NO20023389D0 (no) | 2002-07-12 |
| BR0202674A (pt) | 2003-05-06 |
| US20030109533A1 (en) | 2003-06-12 |
| JP4138382B2 (ja) | 2008-08-27 |
| EP1275644A1 (fr) | 2003-01-15 |
| NO20023389L (no) | 2003-01-14 |
| PL354948A1 (en) | 2003-01-27 |
| EA200200665A1 (ru) | 2003-02-27 |
| FR2827287A1 (fr) | 2003-01-17 |
| NO323868B1 (no) | 2007-07-16 |
| FR2827287B1 (fr) | 2003-10-31 |
| CA2394037A1 (fr) | 2003-01-13 |
| CN1397550A (zh) | 2003-02-19 |
| CN1168715C (zh) | 2004-09-29 |
| KR20030007173A (ko) | 2003-01-23 |
| MXPA02006852A (es) | 2005-07-25 |
| EA005403B1 (ru) | 2005-02-24 |
| ZA200205598B (en) | 2003-03-27 |
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