DE69818709T2 - Derivatives of aminoalkane sulphonic, phosphonic and phosphinic acids, their preparation and their use as medicaments - Google Patents
Derivatives of aminoalkane sulphonic, phosphonic and phosphinic acids, their preparation and their use as medicaments Download PDFInfo
- Publication number
- DE69818709T2 DE69818709T2 DE69818709T DE69818709T DE69818709T2 DE 69818709 T2 DE69818709 T2 DE 69818709T2 DE 69818709 T DE69818709 T DE 69818709T DE 69818709 T DE69818709 T DE 69818709T DE 69818709 T2 DE69818709 T2 DE 69818709T2
- Authority
- DE
- Germany
- Prior art keywords
- propane sulfonate
- methyl
- calcium
- acetylamino
- formula
- 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 - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title 1
- -1 C1-C7 alkyl radical Chemical class 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 5
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 4
- 239000011575 calcium Substances 0.000 claims description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- LOTOBTWNEWUWSF-UHFFFAOYSA-N C(CCC)(=O)NCCC.[Ca] Chemical compound C(CCC)(=O)NCCC.[Ca] LOTOBTWNEWUWSF-UHFFFAOYSA-N 0.000 claims description 2
- CUWQOHWUBMWVIC-UHFFFAOYSA-N C(CCC)(=O)NCCC.[Mg] Chemical compound C(CCC)(=O)NCCC.[Mg] CUWQOHWUBMWVIC-UHFFFAOYSA-N 0.000 claims description 2
- PNCNZTQXAGRKJM-UHFFFAOYSA-N C(CCCC)(=O)NCCC.[Ca] Chemical compound C(CCCC)(=O)NCCC.[Ca] PNCNZTQXAGRKJM-UHFFFAOYSA-N 0.000 claims description 2
- KGWJVBUGODPYHS-UHFFFAOYSA-N CC(C(=O)NCCC)C.[Mg] Chemical compound CC(C(=O)NCCC)C.[Mg] KGWJVBUGODPYHS-UHFFFAOYSA-N 0.000 claims description 2
- DWGOHWRVKOKUBB-UHFFFAOYSA-L magnesium;propane-1-sulfonate Chemical compound [Mg+2].CCCS([O-])(=O)=O.CCCS([O-])(=O)=O DWGOHWRVKOKUBB-UHFFFAOYSA-L 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- MXPVDZNUFQTBSG-UHFFFAOYSA-N [Ca].C(C)(=O)NC(CC)C Chemical compound [Ca].C(C)(=O)NC(CC)C MXPVDZNUFQTBSG-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 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 claims 1
- 208000007848 Alcoholism Diseases 0.000 abstract description 3
- 201000007930 alcohol dependence Diseases 0.000 abstract 1
- 101150021878 Irgc gene Proteins 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- QVXSMDMUQLZRHG-UHFFFAOYSA-L calcium;4-acetamidobutane-2-sulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C(C)CCNC(C)=O.[O-]S(=O)(=O)C(C)CCNC(C)=O QVXSMDMUQLZRHG-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- ZIRURAJAJIQZFG-UHFFFAOYSA-N 1-aminopropane-1-sulfonic acid Chemical compound CCC(N)S(O)(=O)=O ZIRURAJAJIQZFG-UHFFFAOYSA-N 0.000 description 1
- QLEPTNZHIYOYRX-UHFFFAOYSA-N 5,5,5-trifluoro-4-oxopentane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCC(=O)C(F)(F)F QLEPTNZHIYOYRX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VWJFFSONTVUNPG-UHFFFAOYSA-M CC(C)C(NCCCS([O-])(=O)=O)=O Chemical compound CC(C)C(NCCCS([O-])(=O)=O)=O VWJFFSONTVUNPG-UHFFFAOYSA-M 0.000 description 1
- UXRUVQDVKPABMX-UHFFFAOYSA-M CC(CCS([O-])(=O)=O)NC(C)=O Chemical compound CC(CCS([O-])(=O)=O)NC(C)=O UXRUVQDVKPABMX-UHFFFAOYSA-M 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960004047 acamprosate Drugs 0.000 description 1
- BUVGWDNTAWHSKI-UHFFFAOYSA-L acamprosate calcium Chemical compound [Ca+2].CC(=O)NCCCS([O-])(=O)=O.CC(=O)NCCCS([O-])(=O)=O BUVGWDNTAWHSKI-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical class CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- FZYSYWMTWIMFKE-UHFFFAOYSA-L calcium;3-acetamido-2-methylpropane-1-sulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)CC(C)CNC(C)=O.[O-]S(=O)(=O)CC(C)CNC(C)=O FZYSYWMTWIMFKE-UHFFFAOYSA-L 0.000 description 1
- JIWUPBHLZYEVFL-UHFFFAOYSA-L calcium;3-acetamido-2-phenylpropane-1-sulfonate Chemical compound [Ca+2].CC(=O)NCC(CS([O-])(=O)=O)C1=CC=CC=C1.CC(=O)NCC(CS([O-])(=O)=O)C1=CC=CC=C1 JIWUPBHLZYEVFL-UHFFFAOYSA-L 0.000 description 1
- CFKRRDNVLLUTOV-UHFFFAOYSA-L calcium;3-acetamidobutane-1-sulfonate Chemical compound [Ca+2].CC(=O)NC(C)CCS([O-])(=O)=O.CC(=O)NC(C)CCS([O-])(=O)=O CFKRRDNVLLUTOV-UHFFFAOYSA-L 0.000 description 1
- 229930003827 cannabinoid Natural products 0.000 description 1
- 239000003557 cannabinoid Substances 0.000 description 1
- 229940065144 cannabinoids Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011670 long-evans rat Methods 0.000 description 1
- KUPZXZHPXWORDV-UHFFFAOYSA-L magnesium;3-acetamidobutane-1-sulfonate Chemical compound [Mg+2].CC(=O)NC(C)CCS([O-])(=O)=O.CC(=O)NC(C)CCS([O-])(=O)=O KUPZXZHPXWORDV-UHFFFAOYSA-L 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
- C07C309/15—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton the nitrogen atom of at least one of the amino groups being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/24—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Addiction (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/FR1998/000147 WO1999037606A1 (fr) | 1998-01-27 | 1998-01-27 | Nouveaux derives d'acides aminoalkane sulfoniques, phosphoniques et phosphiniques, leur preparation et leur utilisation comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69818709D1 DE69818709D1 (en) | 2003-11-06 |
| DE69818709T2 true DE69818709T2 (de) | 2004-08-19 |
Family
ID=9521619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69818709T Expired - Lifetime DE69818709T2 (de) | 1998-01-27 | 1998-01-27 | Derivatives of aminoalkane sulphonic, phosphonic and phosphinic acids, their preparation and their use as medicaments |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6265437B1 (enExample) |
| EP (1) | EP1051393B1 (enExample) |
| JP (1) | JP4156795B2 (enExample) |
| AT (1) | ATE251129T1 (enExample) |
| AU (1) | AU762988B2 (enExample) |
| CA (1) | CA2319272C (enExample) |
| DE (1) | DE69818709T2 (enExample) |
| DK (1) | DK1051393T3 (enExample) |
| ES (1) | ES2209110T3 (enExample) |
| PT (1) | PT1051393E (enExample) |
| SI (1) | SI1051393T1 (enExample) |
| WO (1) | WO1999037606A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070010573A1 (en) * | 2003-06-23 | 2007-01-11 | Xianqi Kong | Methods and compositions for treating amyloid-related diseases |
| AR049199A1 (es) | 2004-06-04 | 2006-07-05 | Aventis Pharma Inc | Derivados de acido propano-fosfinico sustituido |
| EP1836161B1 (en) * | 2004-12-22 | 2016-07-20 | BHI Limited Partnership | Methods and compositions for treating amyloid-related diseases |
| FR2899895B1 (fr) * | 2006-04-12 | 2010-09-17 | Servier Lab | Nouveaux sels de strontium d'acides sulfoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| SI2089417T1 (sl) * | 2006-10-12 | 2015-04-30 | Bhi Limited Partnership | Metode, spojine, sestavki in vektorji za dostavo 3-amino-1-propansulfonske kisline |
| KR100877134B1 (ko) * | 2007-05-03 | 2009-01-09 | 주식회사 엔지켐 | 아캄프로세이트 칼슘의 제조방법 |
| TW200924746A (en) * | 2007-09-07 | 2009-06-16 | Xenoport Inc | Complex pantoic acid ester neopentyl sulfonyl ester cyclization release prodrugs of acamprosate, compositions thereof, and methods of use |
| WO2009033079A1 (en) * | 2007-09-07 | 2009-03-12 | Xenoport, Inc. | Externally masked neopentyl sulfonyl ester cyclization release prodrugs of acamprosate, compositions thereof, and methods of use |
| US20090099253A1 (en) * | 2007-10-15 | 2009-04-16 | Xenoport, Inc. | Internally Masked Neopentyl Sulfonyl Ester Cyclization Release Prodrugs of Acamprosate, Compositions Thereof, and Methods of Use |
| DE102008048791A1 (de) * | 2008-09-24 | 2010-03-25 | Merck Patent Gmbh | Neue Kristallform von Calcium-3-Acetylaminopropan-1-sulfonat |
| IT1392327B1 (it) * | 2008-09-26 | 2012-02-28 | Laboratorio Chimico Int Spa | Nuova forma polimorfa del calcio acamprosato |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2384751A1 (fr) * | 1977-03-23 | 1978-10-20 | Francaise Coop Pharma | Nouveaux derives de la taurine a activite neuro-musculaire renforcee |
| FR2457281A1 (fr) * | 1979-05-23 | 1980-12-19 | Meram Lab | Nouveaux derives de l'acide 3-aminopropanesulfonique ayant une activite membranaire renforcee |
-
1998
- 1998-01-27 AT AT98904231T patent/ATE251129T1/de active
- 1998-01-27 ES ES98904231T patent/ES2209110T3/es not_active Expired - Lifetime
- 1998-01-27 PT PT98904231T patent/PT1051393E/pt unknown
- 1998-01-27 CA CA002319272A patent/CA2319272C/en not_active Expired - Fee Related
- 1998-01-27 JP JP2000528530A patent/JP4156795B2/ja not_active Expired - Fee Related
- 1998-01-27 DE DE69818709T patent/DE69818709T2/de not_active Expired - Lifetime
- 1998-01-27 AU AU62190/98A patent/AU762988B2/en not_active Ceased
- 1998-01-27 DK DK98904231T patent/DK1051393T3/da active
- 1998-01-27 SI SI9830537T patent/SI1051393T1/xx unknown
- 1998-01-27 WO PCT/FR1998/000147 patent/WO1999037606A1/fr not_active Ceased
- 1998-01-27 EP EP98904231A patent/EP1051393B1/fr not_active Expired - Lifetime
- 1998-01-27 US US09/601,079 patent/US6265437B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE251129T1 (de) | 2003-10-15 |
| SI1051393T1 (en) | 2004-02-29 |
| JP4156795B2 (ja) | 2008-09-24 |
| ES2209110T3 (es) | 2004-06-16 |
| EP1051393B1 (fr) | 2003-10-01 |
| DK1051393T3 (da) | 2004-02-02 |
| CA2319272A1 (en) | 1999-07-29 |
| CA2319272C (en) | 2005-11-08 |
| DE69818709D1 (en) | 2003-11-06 |
| PT1051393E (pt) | 2004-02-27 |
| WO1999037606A1 (fr) | 1999-07-29 |
| AU762988B2 (en) | 2003-07-10 |
| AU6219098A (en) | 1999-08-09 |
| JP2002501040A (ja) | 2002-01-15 |
| EP1051393A1 (fr) | 2000-11-15 |
| US6265437B1 (en) | 2001-07-24 |
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