SK286031B6 - Spôsob prípravy 2-metoxy-4-(N-terc- butylaminokarbonyl)benzénsulfonylchloridu - Google Patents
Spôsob prípravy 2-metoxy-4-(N-terc- butylaminokarbonyl)benzénsulfonylchloridu Download PDFInfo
- Publication number
- SK286031B6 SK286031B6 SK47-2002A SK472002A SK286031B6 SK 286031 B6 SK286031 B6 SK 286031B6 SK 472002 A SK472002 A SK 472002A SK 286031 B6 SK286031 B6 SK 286031B6
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- formula
- chloride
- salt
- tert
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- FQBFGERKZZFZNX-UHFFFAOYSA-N 4-(tert-butylcarbamoyl)-2-methoxybenzenesulfonyl chloride Chemical compound COC1=CC(C(=O)NC(C)(C)C)=CC=C1S(Cl)(=O)=O FQBFGERKZZFZNX-UHFFFAOYSA-N 0.000 title abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 7
- 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 claims abstract description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 5
- 230000001035 methylating effect Effects 0.000 claims abstract description 5
- 230000001131 transforming effect Effects 0.000 claims abstract description 5
- RFXNLHJLTSWQDE-UHFFFAOYSA-N 3-hydroxy-4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C(O)=C1 RFXNLHJLTSWQDE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 8
- QWEZBKWXCKXTJG-UHFFFAOYSA-N 4-chlorosulfonyl-3-methoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC=C1S(Cl)(=O)=O QWEZBKWXCKXTJG-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 238000006277 sulfonation reaction Methods 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- HCFOVLXTTSOQRD-UHFFFAOYSA-N S(=O)(=O)(O)C1=CC(=C(C(=O)O)C=C1)OC Chemical compound S(=O)(=O)(O)C1=CC(=C(C(=O)O)C=C1)OC HCFOVLXTTSOQRD-UHFFFAOYSA-N 0.000 claims 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims 1
- VQCHPXGONTUEPJ-UHFFFAOYSA-N 3-methoxy-4-sulfobenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1S(O)(=O)=O VQCHPXGONTUEPJ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- NOLFSFXAWCAJPY-UHFFFAOYSA-N O.[K].COC1=CC(C(O)=O)=CC=C1S(O)(=O)=O Chemical compound O.[K].COC1=CC(C(O)=O)=CC=C1S(O)(=O)=O NOLFSFXAWCAJPY-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- -1 chlorosulfonyl group Chemical group 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- XUHRVZXFBWDCFB-QRTDKPMLSA-N (3R)-4-[[(3S,6S,9S,12R,15S,18R,21R,24R,27R,28R)-12-(3-amino-3-oxopropyl)-6-[(2S)-butan-2-yl]-3-(2-carboxyethyl)-18-(hydroxymethyl)-28-methyl-9,15,21,24-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]amino]-3-[[(2R)-2-[[(3S)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoic acid Chemical compound CCCCCCC[C@H](O)CC(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H]1[C@@H](C)OC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CO)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC1=O)[C@@H](C)CC XUHRVZXFBWDCFB-QRTDKPMLSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- IMUSECAZYPXEFZ-UHFFFAOYSA-N O.[K].OC(=O)C1=CC=C(S(O)(=O)=O)C(O)=C1 Chemical compound O.[K].OC(=O)C1=CC=C(S(O)(=O)=O)C(O)=C1 IMUSECAZYPXEFZ-UHFFFAOYSA-N 0.000 description 1
- 241000795633 Olea <sea slug> Species 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
- 102000008068 Tensins Human genes 0.000 description 1
- 108010088950 Tensins Proteins 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical class CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DEIRKIWOERNNES-UHFFFAOYSA-M potassium 3-hydroxy-4-sulfobenzoate hydrate Chemical compound O.[K+].Oc1cc(ccc1S(O)(=O)=O)C([O-])=O DEIRKIWOERNNES-UHFFFAOYSA-M 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- 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
- C07C303/04—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 by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—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 by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- 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
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/60—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9902375A HU225150B1 (en) | 1999-07-15 | 1999-07-15 | Novel process for producing 2-methoxy-4-(t-butylaminocarbonyl)-benzenesulfonyl chloride |
| PCT/HU2000/000080 WO2001005754A1 (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(n-t-butylamino-carbonyl)-benzenesulfonyl chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK472002A3 SK472002A3 (en) | 2003-02-04 |
| SK286031B6 true SK286031B6 (sk) | 2008-01-07 |
Family
ID=89998737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK47-2002A SK286031B6 (sk) | 1999-07-15 | 2000-07-13 | Spôsob prípravy 2-metoxy-4-(N-terc- butylaminokarbonyl)benzénsulfonylchloridu |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6548702B1 (cs) |
| EP (1) | EP1202960B1 (cs) |
| JP (1) | JP4636761B2 (cs) |
| CN (1) | CN1164571C (cs) |
| AT (1) | ATE261430T1 (cs) |
| AU (1) | AU6308300A (cs) |
| BR (1) | BR0012430B1 (cs) |
| CA (1) | CA2378337C (cs) |
| CZ (1) | CZ2002146A3 (cs) |
| DE (1) | DE60008884T2 (cs) |
| ES (1) | ES2215699T3 (cs) |
| HR (1) | HRP20020141B1 (cs) |
| HU (1) | HU225150B1 (cs) |
| MX (1) | MXPA01013342A (cs) |
| PL (1) | PL199425B1 (cs) |
| SK (1) | SK286031B6 (cs) |
| WO (1) | WO2001005754A1 (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1421064E (pt) * | 2001-07-31 | 2005-08-31 | Sanofi Aventis | Processo para a preparacao de derivados de 3-espiro'ciclohexan-1,3'-'3h}indolin-2'-ona} |
| CN105621518A (zh) * | 2015-12-29 | 2016-06-01 | 浙江奇彩环境科技股份有限公司 | 一种3,4-二氯苯磺酸废水的资源化处理方法 |
| CN110372548A (zh) * | 2018-04-12 | 2019-10-25 | 南京化学试剂股份有限公司 | 一种5-磺基水杨酸的精制方法 |
| CN113402437B (zh) * | 2021-06-29 | 2023-07-14 | 河北维达康生物科技有限公司 | 一种合成膳食补充剂褪黑素的新方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953507A (en) | 1973-08-31 | 1976-04-27 | Stauffer Chemical Company | N-t-butyl-α-(3,5-substituted phenoxy) alkyl amides and their use as herbicides |
| FR2740136B1 (fr) * | 1995-10-24 | 1998-01-09 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
| FR2757157B1 (fr) * | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
-
1999
- 1999-07-15 HU HU9902375A patent/HU225150B1/hu not_active IP Right Cessation
-
2000
- 2000-07-13 ES ES00949824T patent/ES2215699T3/es not_active Expired - Lifetime
- 2000-07-13 WO PCT/HU2000/000080 patent/WO2001005754A1/en active IP Right Grant
- 2000-07-13 PL PL352466A patent/PL199425B1/pl not_active IP Right Cessation
- 2000-07-13 JP JP2001511415A patent/JP4636761B2/ja not_active Expired - Fee Related
- 2000-07-13 AU AU63083/00A patent/AU6308300A/en not_active Abandoned
- 2000-07-13 BR BRPI0012430-3A patent/BR0012430B1/pt not_active IP Right Cessation
- 2000-07-13 CN CNB008102945A patent/CN1164571C/zh not_active Expired - Fee Related
- 2000-07-13 US US10/030,655 patent/US6548702B1/en not_active Expired - Fee Related
- 2000-07-13 DE DE60008884T patent/DE60008884T2/de not_active Expired - Lifetime
- 2000-07-13 MX MXPA01013342A patent/MXPA01013342A/es active IP Right Grant
- 2000-07-13 CZ CZ2002146A patent/CZ2002146A3/cs unknown
- 2000-07-13 AT AT00949824T patent/ATE261430T1/de not_active IP Right Cessation
- 2000-07-13 CA CA002378337A patent/CA2378337C/en not_active Expired - Fee Related
- 2000-07-13 HR HR20020141A patent/HRP20020141B1/xx not_active IP Right Cessation
- 2000-07-13 SK SK47-2002A patent/SK286031B6/sk not_active IP Right Cessation
- 2000-07-13 EP EP00949824A patent/EP1202960B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1360569A (zh) | 2002-07-24 |
| HUP9902375A2 (hu) | 2001-05-28 |
| PL199425B1 (pl) | 2008-09-30 |
| US6548702B1 (en) | 2003-04-15 |
| EP1202960B1 (en) | 2004-03-10 |
| HUP9902375A3 (en) | 2002-11-28 |
| BR0012430B1 (pt) | 2011-05-17 |
| DE60008884D1 (de) | 2004-04-15 |
| HRP20020141A2 (en) | 2003-10-31 |
| HU9902375D0 (en) | 1999-10-28 |
| WO2001005754A1 (en) | 2001-01-25 |
| SK472002A3 (en) | 2003-02-04 |
| HRP20020141B1 (en) | 2010-09-30 |
| PL352466A1 (en) | 2003-08-25 |
| CA2378337C (en) | 2008-05-20 |
| EP1202960A1 (en) | 2002-05-08 |
| CZ2002146A3 (cs) | 2002-11-13 |
| MXPA01013342A (es) | 2002-08-20 |
| ES2215699T3 (es) | 2004-10-16 |
| BR0012430A (pt) | 2002-03-26 |
| JP2003505366A (ja) | 2003-02-12 |
| HU225150B1 (en) | 2006-07-28 |
| CN1164571C (zh) | 2004-09-01 |
| AU6308300A (en) | 2001-02-05 |
| ATE261430T1 (de) | 2004-03-15 |
| CA2378337A1 (en) | 2001-01-25 |
| DE60008884T2 (de) | 2005-02-03 |
| JP4636761B2 (ja) | 2011-02-23 |
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