CA1051897A - Process for preparing mono- and di-esters of 2,5-dihydroxybenzene sulfonic acid - Google Patents
Process for preparing mono- and di-esters of 2,5-dihydroxybenzene sulfonic acidInfo
- Publication number
- CA1051897A CA1051897A CA218,959A CA218959A CA1051897A CA 1051897 A CA1051897 A CA 1051897A CA 218959 A CA218959 A CA 218959A CA 1051897 A CA1051897 A CA 1051897A
- Authority
- CA
- Canada
- Prior art keywords
- sulfonic acid
- salt
- isobutyroyl
- benzene sulfonic
- dihydroxy benzene
- 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.)
- Expired
Links
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 150000005690 diesters Chemical class 0.000 title claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 47
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 31
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 26
- 159000000007 calcium salts Chemical class 0.000 claims description 17
- 150000003222 pyridines Chemical class 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 229960005141 piperazine Drugs 0.000 claims description 13
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 11
- 239000011575 calcium Substances 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- 159000000003 magnesium salts Chemical class 0.000 claims description 9
- 150000004885 piperazines Chemical class 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- 230000003472 neutralizing effect Effects 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- CTLTUPWEUCZSIP-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical compound OC1=CCC(O)(S(O)(=O)=O)C=C1 CTLTUPWEUCZSIP-UHFFFAOYSA-N 0.000 claims description 5
- OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000292 calcium oxide Substances 0.000 claims description 5
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229960003506 piperazine hexahydrate Drugs 0.000 claims description 5
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical group O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000001095 magnesium carbonate Substances 0.000 claims description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 4
- VVRFXEYVUZOYTI-UHFFFAOYSA-N [2-(4-chlorophenoxy)-2-methylpropanoyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 VVRFXEYVUZOYTI-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 12
- ULOMJXYDGFYHKH-UHFFFAOYSA-N [4-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxyphenyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound ClC1=CC=C(OC(C(=O)OC2=CC=C(C=C2)OC(C(C)(C)OC2=CC=C(C=C2)Cl)=O)(C)C)C=C1 ULOMJXYDGFYHKH-UHFFFAOYSA-N 0.000 claims 6
- 230000000875 corresponding effect Effects 0.000 claims 4
- HBGOLJKPSFNJSD-UHFFFAOYSA-N Etamsylate Chemical compound CC[NH2+]CC.OC1=CC=C(O)C(S([O-])(=O)=O)=C1 HBGOLJKPSFNJSD-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 150000001767 cationic compounds Chemical class 0.000 abstract description 2
- 201000005577 familial hyperlipidemia Diseases 0.000 abstract description 2
- 150000002892 organic cations Chemical class 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- -1 di-O Chemical class 0.000 description 8
- RXGNRJQGYJGPOS-UHFFFAOYSA-N CC(C=O)(C(O)=O)OC(C=C1)=CC=C1Cl Chemical compound CC(C=O)(C(O)=O)OC(C=C1)=CC=C1Cl RXGNRJQGYJGPOS-UHFFFAOYSA-N 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
- 229960004337 hydroquinone Drugs 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- WRSHXWJSBPKQIS-UHFFFAOYSA-N phenyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC1=CC=CC=C1 WRSHXWJSBPKQIS-UHFFFAOYSA-N 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- UGXZVBVMVSMHNM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-3-oxobutanoic acid Chemical compound CC(=O)C(C(O)=O)OC1=CC=C(Cl)C=C1 UGXZVBVMVSMHNM-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- DLZVZOBLKBDRLS-UHFFFAOYSA-N (2-chlorophenyl) 2-methylpropaneperoxoate Chemical compound C(C(C)C)(=O)OOC1=C(C=CC=C1)Cl DLZVZOBLKBDRLS-UHFFFAOYSA-N 0.000 description 1
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- IKBZCVJPNWJDLH-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid 4-methylbenzenesulfonic acid piperazine Chemical compound S(=O)(=O)(O)C1=CC=C(C)C=C1.OC1=C(C=C(C=C1)O)S(=O)(=O)O.N1CCNCC1 IKBZCVJPNWJDLH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YPEQYRIRQCIFNK-UHFFFAOYSA-N 2-methylpropanoic acid;dihydrate Chemical compound O.O.CC(C)C(O)=O YPEQYRIRQCIFNK-UHFFFAOYSA-N 0.000 description 1
- 101150067539 AMBP gene Proteins 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QGNBTYAQAPLTMX-UHFFFAOYSA-L calcium dobesilate Chemical compound [Ca+2].OC1=CC=C(O)C(S([O-])(=O)=O)=C1.OC1=CC=C(O)C(S([O-])(=O)=O)=C1 QGNBTYAQAPLTMX-UHFFFAOYSA-L 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/18—Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH628874A CH591437A5 (enrdf_load_stackoverflow) | 1974-05-08 | 1974-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051897A true CA1051897A (en) | 1979-04-03 |
Family
ID=4307191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,959A Expired CA1051897A (en) | 1974-05-08 | 1975-01-29 | Process for preparing mono- and di-esters of 2,5-dihydroxybenzene sulfonic acid |
Country Status (12)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2015433A6 (es) * | 1989-08-03 | 1990-08-16 | Esteve Quimica Sa | Procedimientos de preparacion de la sal de piperacina del monotosilato del acido 2,5-dihidroxibencenosulfonico |
| US5214191A (en) * | 1990-05-22 | 1993-05-25 | Cortech, Inc. | Oxidant sensitive and insensitive aromatic esters as inhibitors of human neutrophil elastase |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH563356A5 (enrdf_load_stackoverflow) * | 1972-05-17 | 1975-06-30 | Esteve Dr Lab Del Sa | |
| AR204506A1 (es) * | 1972-05-17 | 1976-02-12 | Esteve Labor Dr | Procedimiento de preparacion de sales de acidos p-dihidroxibencenodisulfonicos |
| CH551956A (fr) * | 1972-05-17 | 1974-07-31 | Esteve Lab Del Dr Sa | Procede pour la preparation de sels de sulfones derivant des acides 2,5-dihydroxybenzenemonosulfonique et 2,5dihydroxybenzenedisulfonique. |
-
1974
- 1974-05-08 CH CH628874A patent/CH591437A5/xx not_active IP Right Cessation
- 1974-12-17 DE DE19742459614 patent/DE2459614A1/de not_active Ceased
- 1974-12-20 DK DK671274A patent/DK671274A/da unknown
- 1974-12-27 NL NL7416909A patent/NL7416909A/xx not_active Application Discontinuation
-
1975
- 1975-01-06 RO RO7581049A patent/RO72515A/ro unknown
- 1975-01-28 GB GB3752/75A patent/GB1490247A/en not_active Expired
- 1975-01-29 CA CA218,959A patent/CA1051897A/en not_active Expired
- 1975-02-10 ZA ZA00750833A patent/ZA75833B/xx unknown
- 1975-02-10 BE BE153219A patent/BE825369R/xx not_active IP Right Cessation
- 1975-02-14 FR FR7504673A patent/FR2269931B2/fr not_active Expired
- 1975-03-26 JP JP50036643A patent/JPS50148518A/ja active Pending
- 1975-05-07 DD DD185898A patent/DD119782A6/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7416909A (nl) | 1975-11-11 |
| BE825369R (fr) | 1975-05-29 |
| FR2269931B2 (enrdf_load_stackoverflow) | 1978-07-21 |
| JPS50148518A (enrdf_load_stackoverflow) | 1975-11-28 |
| RO72515A (ro) | 1982-05-10 |
| DE2459614A1 (de) | 1975-11-20 |
| DK671274A (da) | 1975-11-09 |
| FR2269931A2 (enrdf_load_stackoverflow) | 1975-12-05 |
| ZA75833B (en) | 1976-01-28 |
| AU7824775A (en) | 1976-08-19 |
| CH591437A5 (enrdf_load_stackoverflow) | 1977-09-15 |
| DD119782A6 (enrdf_load_stackoverflow) | 1976-05-12 |
| GB1490247A (en) | 1977-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5719168A (en) | Acetamide derivatives and their use as feeding behaviour modifiers | |
| PT93014B (pt) | Processo para a preparacao de novas carboxamidas e sulfonamidas e de composicoes farmaceuticas que as contem | |
| JP6160621B2 (ja) | ピロロキノリンキノンテトラアルカリ塩及びその結晶、これらの製造方法、並びに、組成物 | |
| HU185576B (en) | Process for producing n-acylized l-proline derivatives | |
| US4115648A (en) | 2,5-Dihydroxy benzene sulfonic acid mono esters | |
| US3954767A (en) | Piperazine salts of 2,5-dihydroxy benzene sulfonic acid mono- and diesters | |
| CA1051897A (en) | Process for preparing mono- and di-esters of 2,5-dihydroxybenzene sulfonic acid | |
| US5051515A (en) | Novel generation of heteroaryl thio, sulfoxy, or sulfonyl alkyl azoles | |
| HK217196A (en) | Diamine salts of clavulanic acid | |
| GB2144038A (en) | Adenosine derivatives of antiinflammatory and analgesic activity and therapeutic compositions containing them | |
| US4910222A (en) | Cysteine derivatives having expectorant activity | |
| US4202832A (en) | Thiocarbamoylthio fatty acids | |
| CH622777A5 (enrdf_load_stackoverflow) | ||
| US4628083A (en) | 2-hydroxy-5-(arylazo)-benzene alkanoic acids | |
| US4031240A (en) | 2,5-Dihydroxy benzene sulfonic acid mono- and diesters | |
| EP0021229B1 (en) | Arylazo compounds, their preparation and their use | |
| US4985595A (en) | Aminobenzamide derivatives | |
| EP0121806A1 (en) | Pyrazolo(1,5-a)pyridine derivatives and compositions containing them | |
| ES2209104T3 (es) | Procedimiento para producir compuestos de imidazol opticamente activos, intermedios en su sintesis y procedimiento de preparacion. | |
| KR20040016837A (ko) | 3 ―（3 ―아미디노페닐）―5 ―〔（｛〔1 ―（1―이미노에틸）―4 ―피페리딜}아미노）메틸〕벤조산디히드로클로라이드 및 그의 제조 방법 | |
| US2657212A (en) | Diethanolaminopyridines | |
| US4296128A (en) | Carboxylic acid hydrazides and processes for their manufacture | |
| US4900841A (en) | 1-[4-[(methyl-sulfonyl)amino]benzoyl]aziridine | |
| US4268685A (en) | Salicylamide esters and related pharmaceutical composition | |
| JPS5470277A (en) | Hydroxyindole derivatives |