KR20080027868A - 설폰산염으로부터 설포닐 할라이드 및 설폰아미드의 합성방법 - Google Patents
설폰산염으로부터 설포닐 할라이드 및 설폰아미드의 합성방법 Download PDFInfo
- Publication number
- KR20080027868A KR20080027868A KR1020087001647A KR20087001647A KR20080027868A KR 20080027868 A KR20080027868 A KR 20080027868A KR 1020087001647 A KR1020087001647 A KR 1020087001647A KR 20087001647 A KR20087001647 A KR 20087001647A KR 20080027868 A KR20080027868 A KR 20080027868A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- formula
- compound
- group
- halogen
- 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.)
- Ceased
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 15
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 75
- 150000003461 sulfonyl halides Chemical class 0.000 title abstract description 19
- 150000003871 sulfonates Chemical class 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title description 14
- 238000003786 synthesis reaction Methods 0.000 title description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 76
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 70
- 125000005843 halogen group Chemical group 0.000 claims abstract description 46
- 238000006467 substitution reaction Methods 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 150000001412 amines Chemical class 0.000 claims abstract description 30
- 230000003197 catalytic effect Effects 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- -1 2-trifluoromethylphenyl Chemical group 0.000 claims description 26
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 26
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 9
- 229910001415 sodium ion Inorganic materials 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910001414 potassium ion Inorganic materials 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 239000003426 co-catalyst Substances 0.000 claims description 6
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- HIZOPJQOPKRKFM-UHFFFAOYSA-N 4-[3-[1-benzhydryl-5-chloro-2-[2-[(3,4-dichlorophenyl)methylsulfonylamino]ethyl]indol-3-yl]propyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCCC(C1=CC(Cl)=CC=C1N1C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1CCNS(=O)(=O)CC1=CC=C(Cl)C(Cl)=C1 HIZOPJQOPKRKFM-UHFFFAOYSA-N 0.000 claims description 3
- NHHBNHIPCSPSHQ-UHFFFAOYSA-N 4-[3-[1-benzhydryl-5-chloro-2-[2-[[2-(trifluoromethyl)phenyl]methylsulfonylamino]ethyl]indol-3-yl]propyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCCC(C1=CC(Cl)=CC=C1N1C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1CCNS(=O)(=O)CC1=CC=CC=C1C(F)(F)F NHHBNHIPCSPSHQ-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
- CKFWZXFTPKMTRD-UHFFFAOYSA-N 4-[3-[1-benzhydryl-5-chloro-2-[2-[[2-(trifluoromethoxy)phenyl]methylsulfonylamino]ethyl]indol-3-yl]propyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCCC(C1=CC(Cl)=CC=C1N1C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1CCNS(=O)(=O)CC1=CC=CC=C1OC(F)(F)F CKFWZXFTPKMTRD-UHFFFAOYSA-N 0.000 claims description 2
- FGFOPJQWLFNOGD-UHFFFAOYSA-N 4-[3-[1-benzhydryl-5-chloro-2-[2-[[2-fluoro-6-(trifluoromethyl)phenyl]methylsulfonylamino]ethyl]indol-3-yl]propyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCCC(C1=CC(Cl)=CC=C1N1C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1CCNS(=O)(=O)CC1=C(F)C=CC=C1C(F)(F)F FGFOPJQWLFNOGD-UHFFFAOYSA-N 0.000 claims description 2
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- VZLKQEPNZIWSFF-UHFFFAOYSA-N 1-pyrrolidin-1-ylpiperidine Chemical compound C1CCCN1N1CCCCC1 VZLKQEPNZIWSFF-UHFFFAOYSA-N 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 4
- 150000004820 halides Chemical class 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003636 chemical group Chemical group 0.000 description 6
- RFFCAUGRAMHQSO-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]methanesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1CS(Cl)(=O)=O RFFCAUGRAMHQSO-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- IOWBSTPROVYJMM-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1C(F)(F)F IOWBSTPROVYJMM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- KUCRAQDBLZUBQD-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]methanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1C(F)(F)F KUCRAQDBLZUBQD-UHFFFAOYSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000010949 in-process test method Methods 0.000 description 1
- 238000013339 in-process testing Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ZAHRNXJEDUNRLQ-UHFFFAOYSA-N methyl 4-[3-[1-benzhydryl-5-chloro-2-[2-[[2-(trifluoromethyl)phenyl]methylsulfonylamino]ethyl]indol-3-yl]propyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCCC(C1=CC(Cl)=CC=C1N1C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1CCNS(=O)(=O)CC1=CC=CC=C1C(F)(F)F ZAHRNXJEDUNRLQ-UHFFFAOYSA-N 0.000 description 1
- YQVPSPUPLXXAKG-UHFFFAOYSA-N methyl 4-[3-[2-(2-aminoethyl)-1-benzhydryl-5-chloroindol-3-yl]propyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCCC(C1=CC(Cl)=CC=C11)=C(CCN)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 YQVPSPUPLXXAKG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005893 naphthalimidyl group Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000003358 phospholipase A2 inhibitor Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229940126586 small molecule drug Drugs 0.000 description 1
- 239000011734 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/07—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70115805P | 2005-07-21 | 2005-07-21 | |
| US60/701,158 | 2005-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080027868A true KR20080027868A (ko) | 2008-03-28 |
Family
ID=37571383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087001647A Ceased KR20080027868A (ko) | 2005-07-21 | 2006-07-20 | 설폰산염으로부터 설포닐 할라이드 및 설폰아미드의 합성방법 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7842834B2 (enExample) |
| EP (1) | EP1907355B1 (enExample) |
| JP (1) | JP4926172B2 (enExample) |
| KR (1) | KR20080027868A (enExample) |
| CN (1) | CN101228118B (enExample) |
| AR (1) | AR057676A1 (enExample) |
| AU (1) | AU2006272886B2 (enExample) |
| BR (1) | BRPI0614005A2 (enExample) |
| CA (1) | CA2610228C (enExample) |
| CR (1) | CR9581A (enExample) |
| EC (1) | ECSP088116A (enExample) |
| ES (1) | ES2556620T3 (enExample) |
| GT (1) | GT200600325A (enExample) |
| IL (1) | IL187711A (enExample) |
| MX (1) | MX2008000816A (enExample) |
| NI (1) | NI200800018A (enExample) |
| NO (1) | NO20076358L (enExample) |
| PE (1) | PE20070245A1 (enExample) |
| RU (1) | RU2466983C2 (enExample) |
| SG (1) | SG163550A1 (enExample) |
| TW (1) | TW200728262A (enExample) |
| WO (1) | WO2007013974A2 (enExample) |
| ZA (1) | ZA200800557B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR048239A1 (es) | 2004-02-25 | 2006-04-12 | Wyeth Corp | Procesos para la preparacion de haluros de aril- y heteroaril-alquilsulfonilo e intermediarios de sintesis de los mismos |
| CA2610228C (en) | 2005-07-21 | 2014-02-18 | Wyeth | Process for the synthesis of sulfonyl halides and sulfonamides from sulfonic acid salts |
| TW201036941A (en) * | 2009-03-30 | 2010-10-16 | Sumitomo Chemical Co | Method for producing sulfonamide compound |
| CN102887841A (zh) * | 2012-11-02 | 2013-01-23 | 天津希恩思生化科技有限公司 | 化合物丹磺酰氯的制备方法 |
| CN109722230B (zh) * | 2017-10-27 | 2021-07-23 | 中石化石油工程技术服务有限公司 | 一种油基钻井液用乳化剂及其制备方法和钻井液 |
| CN112110863A (zh) * | 2020-08-27 | 2020-12-22 | 中山大学 | 一种磺酰氟类化合物、其制备方法以及通过其制备磺酰胺类化合物的方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE150313C (enExample) | ||||
| DE48722C (de) | Dr. E. FISCHER in Stuttgart, Schlofsstrafse 29 | Verfahren zur Darstellung von O-Nitrobenzaldehyd aus O-Nitrobenzylchlorid | ||
| US2199568A (en) * | 1938-06-11 | 1940-05-07 | Gen Aniline & Film Corp | Manufacture of 1-methyl-4-chloro-5-hydroxynaphthalene-11-sulphonic acid |
| US2507408A (en) * | 1948-03-05 | 1950-05-09 | Rhone Poulenc Sa | 1-alkylsulfonyl-4-alkyl piperazines |
| US2888486A (en) * | 1953-11-20 | 1959-05-26 | Du Pont | Process for producing aromatic sulfonyl halides |
| US4885027A (en) * | 1985-04-05 | 1989-12-05 | Chevron Research Company | Herbicidal arylmethylenesulfonamido-acetamide and thioacetamide derivatives |
| JPS6310795A (ja) * | 1986-03-25 | 1988-01-18 | Takeda Chem Ind Ltd | 選択性除草化合物 |
| JP3814696B2 (ja) * | 1995-04-17 | 2006-08-30 | 住友精化株式会社 | 芳香族またはヘテロ芳香族スルホニルハライド類の製造方法 |
| JPH11292865A (ja) * | 1998-04-03 | 1999-10-26 | Ono Pharmaceut Co Ltd | 医薬品の中間体の製造方法 |
| JP4594574B2 (ja) * | 1999-08-03 | 2010-12-08 | 株式会社クレハ | Ｎ−（ベンジルスルホニル）ピコリン酸アミド誘導体、その製造方法及び除草剤 |
| FR2802121A1 (fr) * | 1999-12-14 | 2001-06-15 | Expansia Sa | Supports polymeriques organiques possedant des ligands mono- ou bi-dentates et leur utilisation en catalyse supportee |
| ES2401454T3 (es) * | 2001-12-03 | 2013-04-19 | Wyeth Llc | Inhibidores de la fosfolipasa A2 citosólica |
| SI1656370T1 (sl) * | 2003-06-03 | 2012-12-31 | Rib-X Pharmaceuticals, Inc. | Biarilne heterociklične spojine in postopki za njihovo izdelavo in uporabo |
| AR048239A1 (es) * | 2004-02-25 | 2006-04-12 | Wyeth Corp | Procesos para la preparacion de haluros de aril- y heteroaril-alquilsulfonilo e intermediarios de sintesis de los mismos |
| CA2610228C (en) | 2005-07-21 | 2014-02-18 | Wyeth | Process for the synthesis of sulfonyl halides and sulfonamides from sulfonic acid salts |
| WO2010048122A1 (en) * | 2008-10-22 | 2010-04-29 | Cytec Technology Corp. | Improved processing of polymer matrix composites |
-
2006
- 2006-07-20 CA CA2610228A patent/CA2610228C/en active Active
- 2006-07-20 SG SG201004719-9A patent/SG163550A1/en unknown
- 2006-07-20 WO PCT/US2006/028182 patent/WO2007013974A2/en not_active Ceased
- 2006-07-20 EP EP06800157.7A patent/EP1907355B1/en active Active
- 2006-07-20 BR BRPI0614005-0A patent/BRPI0614005A2/pt not_active Application Discontinuation
- 2006-07-20 JP JP2008522959A patent/JP4926172B2/ja not_active Expired - Fee Related
- 2006-07-20 RU RU2007149184/04A patent/RU2466983C2/ru not_active Application Discontinuation
- 2006-07-20 NI NI200800018A patent/NI200800018A/es unknown
- 2006-07-20 US US11/490,389 patent/US7842834B2/en active Active
- 2006-07-20 MX MX2008000816A patent/MX2008000816A/es active IP Right Grant
- 2006-07-20 ES ES06800157.7T patent/ES2556620T3/es active Active
- 2006-07-20 KR KR1020087001647A patent/KR20080027868A/ko not_active Ceased
- 2006-07-20 TW TW095126535A patent/TW200728262A/zh unknown
- 2006-07-20 CN CN200680026736XA patent/CN101228118B/zh not_active Expired - Fee Related
- 2006-07-20 AU AU2006272886A patent/AU2006272886B2/en not_active Ceased
- 2006-07-21 AR ARP060103164A patent/AR057676A1/es unknown
- 2006-07-21 PE PE2006000883A patent/PE20070245A1/es not_active Application Discontinuation
- 2006-07-21 GT GT200600325A patent/GT200600325A/es unknown
-
2007
- 2007-11-28 IL IL187711A patent/IL187711A/en active IP Right Grant
- 2007-12-07 CR CR9581A patent/CR9581A/es not_active Application Discontinuation
- 2007-12-12 NO NO20076358A patent/NO20076358L/no not_active Application Discontinuation
-
2008
- 2008-01-17 EC EC2008008116A patent/ECSP088116A/es unknown
- 2008-01-18 ZA ZA2008/00557A patent/ZA200800557B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL187711A0 (en) | 2008-08-07 |
| BRPI0614005A2 (pt) | 2011-03-01 |
| NI200800018A (es) | 2009-03-03 |
| WO2007013974A3 (en) | 2007-04-12 |
| CR9581A (es) | 2008-03-06 |
| NO20076358L (no) | 2008-04-16 |
| EP1907355A2 (en) | 2008-04-09 |
| IL187711A (en) | 2016-04-21 |
| TW200728262A (en) | 2007-08-01 |
| WO2007013974A2 (en) | 2007-02-01 |
| MX2008000816A (es) | 2008-03-18 |
| AU2006272886A1 (en) | 2007-02-01 |
| ES2556620T3 (es) | 2016-01-19 |
| CN101228118A (zh) | 2008-07-23 |
| CN101228118B (zh) | 2013-09-18 |
| CA2610228C (en) | 2014-02-18 |
| JP2009502802A (ja) | 2009-01-29 |
| AU2006272886B2 (en) | 2012-03-01 |
| ECSP088116A (es) | 2008-02-20 |
| US20070021614A1 (en) | 2007-01-25 |
| ZA200800557B (en) | 2011-06-26 |
| AR057676A1 (es) | 2007-12-12 |
| GT200600325A (es) | 2007-02-26 |
| PE20070245A1 (es) | 2007-03-26 |
| CA2610228A1 (en) | 2007-02-01 |
| SG163550A1 (en) | 2010-08-30 |
| RU2007149184A (ru) | 2009-08-27 |
| US7842834B2 (en) | 2010-11-30 |
| JP4926172B2 (ja) | 2012-05-09 |
| EP1907355B1 (en) | 2015-08-05 |
| RU2466983C2 (ru) | 2012-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU759255B2 (en) | PPAR-gamma modulators | |
| EP2937343A1 (en) | Process of preparing a thrombin specific inhibitor | |
| EP2367807A1 (en) | Process for the preparation of piperazine derivatives | |
| WO2006098308A1 (ja) | 新規なアントラニル酸誘導体またはその塩 | |
| KR20080027868A (ko) | 설폰산염으로부터 설포닐 할라이드 및 설폰아미드의 합성방법 | |
| EP1718605B1 (en) | Processes for the preparation of aryl-and heteroaryl-alkylsulfonyl halides | |
| WO2001023345A1 (en) | Process for the preparation of a piperazine derivative | |
| CN113372329B (zh) | 化合物盐酸法舒地尔的制备方法 | |
| WO2001094304A1 (en) | Process for the production of sulfonic esters | |
| TWI305205B (en) | Catalytic process for the preparation of thiazole derivatives | |
| ES2382697T3 (es) | Inhibidor de la unión de S1P1 | |
| KR20070018857A (ko) | 아릴－ 및 헤테로아릴－알킬술포닐 할라이드의 제조 방법 | |
| EP0976740B1 (en) | A synthesizing method for a 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound | |
| JP2002220371A (ja) | Ｎ−ビニルカルバゾール類の製造方法 | |
| CN119841747A (zh) | 一种含氟磺酰基的胍类化合物及其制备方法和应用 | |
| Gaikwad et al. | Thiourea/NCBSI/HCl System: Telescoping Alkyl Halide to Alkyl Sulfonyl Chloride by Recyclable N-Chloro-N-(phenylsulfonyl) benzene Sulfonamide (NCBSI) | |
| CN117903016A (zh) | 一种氟磺酰磺酰亚胺盐、其制备方法及其应用 | |
| CN115925588A (zh) | 一种脂肪族亚磺酸钠盐的制备方法 | |
| WO2022200444A1 (en) | New process for the synthesis of 5-{5-chloro-2-[(3n)-3- [(morpholin-4-yl)methyl]-3,4-dihydroisoquinoline-2(1h)- carbonyl]phenyl}-1,2-dimethyl-1h-pyrrole-3-carboxylic acid derivatives and its application for the production of pharmaceutical compounds | |
| TW200531964A (en) | One-pot process for the preparation of 1, 2-benz-isoxazole-3-methanesulfonamide | |
| JP2005015428A (ja) | ４−ピリジンチオール類の分離方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20080121 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| AMND | Amendment | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20110715 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20130402 Patent event code: PE09021S01D |
|
| AMND | Amendment | ||
| N231 | Notification of change of applicant | ||
| PN2301 | Change of applicant |
Patent event date: 20131111 Comment text: Notification of Change of Applicant Patent event code: PN23011R01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20131120 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20130402 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
|
| J201 | Request for trial against refusal decision | ||
| PJ0201 | Trial against decision of rejection |
Patent event date: 20140221 Comment text: Request for Trial against Decision on Refusal Patent event code: PJ02012R01D Patent event date: 20131120 Comment text: Decision to Refuse Application Patent event code: PJ02011S01I Appeal kind category: Appeal against decision to decline refusal Appeal identifier: 2014101001019 Request date: 20140221 |
|
| AMND | Amendment | ||
| PB0901 | Examination by re-examination before a trial |
Comment text: Amendment to Specification, etc. Patent event date: 20140324 Patent event code: PB09011R02I Comment text: Request for Trial against Decision on Refusal Patent event date: 20140221 Patent event code: PB09011R01I Comment text: Amendment to Specification, etc. Patent event date: 20130702 Patent event code: PB09011R02I Comment text: Amendment to Specification, etc. Patent event date: 20110715 Patent event code: PB09011R02I |
|
| B601 | Maintenance of original decision after re-examination before a trial | ||
| PB0601 | Maintenance of original decision after re-examination before a trial |
Comment text: Report of Result of Re-examination before a Trial Patent event code: PB06011S01D Patent event date: 20140422 |
|
| J301 | Trial decision |
Free format text: TRIAL DECISION FOR APPEAL AGAINST DECISION TO DECLINE REFUSAL REQUESTED 20140221 Effective date: 20140905 Free format text: TRIAL NUMBER: 2014101001019; TRIAL DECISION FOR APPEAL AGAINST DECISION TO DECLINE REFUSAL REQUESTED 20140221 Effective date: 20140905 |
|
| PJ1301 | Trial decision |
Patent event code: PJ13011S01D Patent event date: 20140905 Comment text: Trial Decision on Objection to Decision on Refusal Appeal kind category: Appeal against decision to decline refusal Request date: 20140221 Decision date: 20140905 Appeal identifier: 2014101001019 |