PL50739B1 - - Google Patents

Info

Publication number

PL50739B1

PL50739B1 PL96643A PL9664361A PL50739B1 PL 50739 B1 PL50739 B1 PL 50739B1 PL 96643 A PL96643 A PL 96643A PL 9664361 A PL9664361 A PL 9664361A PL 50739 B1 PL50739 B1 PL 50739B1

Authority

PL

Poland

Prior art keywords

dihydro

sulfamyl

trifluoroethylthiomethyl

alkali metal

dioxide

Prior art date

1961-06-02

Links

• Espacenet
• Global Dossier
• Discuss

• -1 3- (2,2,2-trifluoroethylthiomethyl) - 6 - substituted - 7 -sulfamyl - 3,4-dihydro - 1,2,4-benzothiadiazine 1,1-dioxides Chemical class 0.000 claims description 29
• 238000000034 method Methods 0.000 claims description 24
• 229910052783 alkali metal Inorganic materials 0.000 claims description 7
• 238000006243 chemical reaction Methods 0.000 claims description 6
• 239000002904 solvent Substances 0.000 claims description 5
• CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims description 4
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
• 150000001340 alkali metals Chemical class 0.000 claims description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 238000011065 in-situ storage Methods 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 150000003839 salts Chemical class 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 239000011734 sodium Substances 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
• 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 239000000460 chlorine Substances 0.000 claims description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 239000003153 chemical reaction reagent Substances 0.000 claims 1
• 238000010790 dilution Methods 0.000 claims 1
• 239000012895 dilution Substances 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 230000007935 neutral effect Effects 0.000 claims 1
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
• 239000000047 product Substances 0.000 description 17
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• 239000000203 mixture Substances 0.000 description 7
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 150000001350 alkyl halides Chemical class 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 150000001875 compounds Chemical class 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 238000001953 recrystallisation Methods 0.000 description 4
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
• 150000004820 halides Chemical class 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 238000004816 paper chromatography Methods 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 239000011591 potassium Substances 0.000 description 3
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 150000001448 anilines Chemical class 0.000 description 2
• 239000006227 byproduct Substances 0.000 description 2
• 150000001805 chlorine compounds Chemical class 0.000 description 2
• 238000011109 contamination Methods 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 229910000103 lithium hydride Inorganic materials 0.000 description 2
• SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 2
• 239000000155 melt Substances 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 230000012495 positive regulation of renal sodium excretion Effects 0.000 description 2
• IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 239000000523 sample Substances 0.000 description 2
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical group [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
• RKOUFQLNMRAACI-UHFFFAOYSA-N 1,1,1-trifluoro-2-iodoethane Chemical compound FC(F)(F)CI RKOUFQLNMRAACI-UHFFFAOYSA-N 0.000 description 1
• 150000008349 1,2,4-benzothiadiazines Chemical class 0.000 description 1
• NHSVBZUCAFSNBR-UHFFFAOYSA-N 2,2-dimethoxyethanethiol Chemical compound COC(CS)OC NHSVBZUCAFSNBR-UHFFFAOYSA-N 0.000 description 1
• ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical group C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
• QRKDOAWSBBGNLE-UHFFFAOYSA-N 2h-1,2,4-benzothiadiazine Chemical compound C1=CC=C2N=CNSC2=C1 QRKDOAWSBBGNLE-UHFFFAOYSA-N 0.000 description 1
• MKRNHDDVWSKUBR-UHFFFAOYSA-N 6-chloro-2-methyl-3-(2,2,2-trifluoroethylsulfanylmethyl)-3,4-dihydro-1,2,4-benzothiadiazine-7-sulfonamide Chemical class NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC(F)(F)F)N(C)SC2=C1 MKRNHDDVWSKUBR-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• ZCUFTCUMEDALHC-UHFFFAOYSA-N CC[K] Chemical compound CC[K] ZCUFTCUMEDALHC-UHFFFAOYSA-N 0.000 description 1
• UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 1
• 241000905957 Channa melasoma Species 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• XFTIKWYXFSNCQF-UHFFFAOYSA-N N,N-dipropylformamide Chemical compound CCCN(C=O)CCC XFTIKWYXFSNCQF-UHFFFAOYSA-N 0.000 description 1
• SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
• 208000004880 Polyuria Diseases 0.000 description 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 150000001335 aliphatic alkanes Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 description 1
• 229960001541 benzthiazide Drugs 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
• 229940046413 calcium iodide Drugs 0.000 description 1
• 229910001640 calcium iodide Inorganic materials 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 238000004140 cleaning Methods 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 239000002934 diuretic Substances 0.000 description 1
• 230000001882 diuretic effect Effects 0.000 description 1
• 239000003792 electrolyte Substances 0.000 description 1
• 238000005187 foaming Methods 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 229910052740 iodine Chemical group 0.000 description 1
• 239000011630 iodine Chemical group 0.000 description 1
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
• AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical group [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
• 229910003002 lithium salt Inorganic materials 0.000 description 1
• 239000011259 mixed solution Substances 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
• MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 150000002902 organometallic compounds Chemical class 0.000 description 1
• 239000003495 polar organic solvent Substances 0.000 description 1
• 229910000105 potassium hydride Inorganic materials 0.000 description 1
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical group [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 238000004451 qualitative analysis Methods 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 239000012070 reactive reagent Substances 0.000 description 1
• 239000013074 reference sample Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 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 description 1