AU2001259053A1 - Sulfonamide derivatives - Google Patents
Sulfonamide derivativesInfo
- Publication number
- AU2001259053A1 AU2001259053A1 AU2001259053A AU5905301A AU2001259053A1 AU 2001259053 A1 AU2001259053 A1 AU 2001259053A1 AU 2001259053 A AU2001259053 A AU 2001259053A AU 5905301 A AU5905301 A AU 5905301A AU 2001259053 A1 AU2001259053 A1 AU 2001259053A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- formula
- phenyl
- pharmaceutically acceptable
- micrograms
- 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.)
- Abandoned
Links
- 150000003456 sulfonamides Chemical class 0.000 title description 21
- 229940124530 sulfonamide Drugs 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 117
- 239000000203 mixture Substances 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 23
- 229920001223 polyethylene glycol Polymers 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims description 12
- 102000018899 Glutamate Receptors Human genes 0.000 claims description 11
- 108010027915 Glutamate Receptors Proteins 0.000 claims description 11
- ULRDYYKSPCRXAJ-KRWDZBQOSA-N n-[(2r)-2-[4-[4-[2-(methanesulfonamido)ethyl]phenyl]phenyl]propyl]propane-2-sulfonamide Chemical compound C1=CC([C@@H](C)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(CCNS(C)(=O)=O)C=C1 ULRDYYKSPCRXAJ-KRWDZBQOSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 239000002775 capsule Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 230000003389 potentiating effect Effects 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 229920002562 Polyethylene Glycol 3350 Polymers 0.000 claims description 6
- 230000007278 cognition impairment Effects 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 239000005022 packaging material Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000007903 gelatin capsule Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229940050929 polyethylene glycol 3350 Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 229910001868 water Inorganic materials 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 238000003756 stirring Methods 0.000 description 37
- 239000007787 solid Substances 0.000 description 33
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 29
- 239000000706 filtrate Substances 0.000 description 29
- 239000003960 organic solvent Substances 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- -1 amphetamines Chemical compound 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000000725 suspension Substances 0.000 description 19
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 229930195712 glutamate Natural products 0.000 description 17
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- 235000019441 ethanol Nutrition 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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- 239000000047 product Substances 0.000 description 14
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- 229940093499 ethyl acetate Drugs 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
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- AXORVIZLPOGIRG-QMMMGPOBSA-N R-BETA-METHYLPHENYLETHYLAMINE Chemical compound NC[C@H](C)C1=CC=CC=C1 AXORVIZLPOGIRG-QMMMGPOBSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000000872 buffer Substances 0.000 description 11
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- 239000002244 precipitate Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- BOCUKUHCLICSIY-QJWLJZLASA-N cyclothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2C1[C@H](C=C2)C[C@H]2C1 BOCUKUHCLICSIY-QJWLJZLASA-N 0.000 description 8
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- 230000006870 function Effects 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 108090000078 AMPA Receptors Proteins 0.000 description 7
- 102000003678 AMPA Receptors Human genes 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 6
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229940044613 1-propanol Drugs 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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- 230000003197 catalytic effect Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229940049920 malate Drugs 0.000 description 5
- ALSHDGWOBNSWLZ-JTQLQIEISA-N n-[(2r)-2-(4-iodophenyl)propyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC[C@H](C)C1=CC=C(I)C=C1 ALSHDGWOBNSWLZ-JTQLQIEISA-N 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- AXORVIZLPOGIRG-UHFFFAOYSA-N β-methylphenethylamine Chemical compound NCC(C)C1=CC=CC=C1 AXORVIZLPOGIRG-UHFFFAOYSA-N 0.000 description 5
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
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- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 230000018405 transmission of nerve impulse Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20600300P | 2000-05-19 | 2000-05-19 | |
| US60206003 | 2000-05-19 | ||
| PCT/US2001/011747 WO2001090057A1 (en) | 2000-05-19 | 2001-05-04 | Sulfonamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001259053A1 true AU2001259053A1 (en) | 2001-12-03 |
Family
ID=22764580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001259053A Abandoned AU2001259053A1 (en) | 2000-05-19 | 2001-05-04 | Sulfonamide derivatives |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20030225163A1 (hr) |
| EP (1) | EP1311474A1 (hr) |
| JP (1) | JP2003534316A (hr) |
| KR (1) | KR20030007644A (hr) |
| CN (1) | CN1429205A (hr) |
| AR (1) | AR035915A1 (hr) |
| AU (1) | AU2001259053A1 (hr) |
| BR (1) | BR0110874A (hr) |
| CA (1) | CA2409830A1 (hr) |
| CZ (1) | CZ20023797A3 (hr) |
| DZ (1) | DZ3343A1 (hr) |
| EA (1) | EA200201234A1 (hr) |
| EC (1) | ECSP014078A (hr) |
| HR (1) | HRP20020918A2 (hr) |
| HU (1) | HUP0302255A3 (hr) |
| IL (1) | IL152156A0 (hr) |
| MX (1) | MXPA02010020A (hr) |
| NO (1) | NO20025459L (hr) |
| PE (1) | PE20020052A1 (hr) |
| PL (1) | PL358180A1 (hr) |
| SK (1) | SK16312002A3 (hr) |
| SV (1) | SV2002000459A (hr) |
| WO (1) | WO2001090057A1 (hr) |
| ZA (1) | ZA200208749B (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9702194D0 (en) | 1997-02-04 | 1997-03-26 | Lilly Co Eli | Sulphonide derivatives |
| US6984756B2 (en) | 2000-05-19 | 2006-01-10 | Eli Lilly And Company | Process for preparing biphenyl compounds |
| AU2001274806A1 (en) | 2000-06-13 | 2001-12-24 | Eli Lilly And Company | Sulfonamide derivatives |
| US20040235957A1 (en) * | 2001-10-12 | 2004-11-25 | David Bleakman | Use of sulfonamide derivatives as pharmaceuticals compounds |
| WO2005013961A1 (en) * | 2003-07-17 | 2005-02-17 | Eli Lilly And Company | Combination therapy for treatment of cognitive disorders or psychoses |
| AU2007333247B2 (en) * | 2006-12-11 | 2012-06-07 | Eli Lilly And Company | AMPA receptor potentiators |
| AU2014277952A1 (en) | 2013-06-13 | 2016-01-28 | Veroscience Llc | Compositions and methods for treating metabolic disorders |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6525099B1 (en) * | 1998-07-31 | 2003-02-25 | Eli Lilly And Company | N-substituted sulfonamide derivatives |
-
2001
- 2001-05-04 CN CN01809667A patent/CN1429205A/zh active Pending
- 2001-05-04 JP JP2001586247A patent/JP2003534316A/ja not_active Withdrawn
- 2001-05-04 MX MXPA02010020A patent/MXPA02010020A/es unknown
- 2001-05-04 KR KR1020027015545A patent/KR20030007644A/ko not_active Application Discontinuation
- 2001-05-04 US US10/258,159 patent/US20030225163A1/en not_active Abandoned
- 2001-05-04 SK SK1631-2002A patent/SK16312002A3/sk unknown
- 2001-05-04 AU AU2001259053A patent/AU2001259053A1/en not_active Abandoned
- 2001-05-04 HU HU0302255A patent/HUP0302255A3/hu unknown
- 2001-05-04 WO PCT/US2001/011747 patent/WO2001090057A1/en not_active Application Discontinuation
- 2001-05-04 CZ CZ20023797A patent/CZ20023797A3/cs unknown
- 2001-05-04 EP EP01932536A patent/EP1311474A1/en not_active Withdrawn
- 2001-05-04 BR BR0110874-3A patent/BR0110874A/pt not_active Application Discontinuation
- 2001-05-04 IL IL15215601A patent/IL152156A0/xx unknown
- 2001-05-04 DZ DZ013343A patent/DZ3343A1/fr active
- 2001-05-04 CA CA002409830A patent/CA2409830A1/en not_active Abandoned
- 2001-05-04 EA EA200201234A patent/EA200201234A1/ru unknown
- 2001-05-04 PL PL01358180A patent/PL358180A1/xx not_active Application Discontinuation
- 2001-05-18 AR ARP010102374A patent/AR035915A1/es unknown
- 2001-05-18 SV SV2001000459A patent/SV2002000459A/es not_active Application Discontinuation
- 2001-05-18 PE PE2001000451A patent/PE20020052A1/es not_active Application Discontinuation
- 2001-05-18 EC EC2001004078A patent/ECSP014078A/es unknown
-
2002
- 2002-10-29 ZA ZA200208749A patent/ZA200208749B/en unknown
- 2002-11-14 NO NO20025459A patent/NO20025459L/no not_active Application Discontinuation
- 2002-11-19 HR HR20020918A patent/HRP20020918A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SV2002000459A (es) | 2002-07-03 |
| NO20025459D0 (no) | 2002-11-14 |
| PE20020052A1 (es) | 2002-02-02 |
| ZA200208749B (en) | 2004-01-30 |
| PL358180A1 (en) | 2004-08-09 |
| WO2001090057A1 (en) | 2001-11-29 |
| HRP20020918A2 (en) | 2004-02-29 |
| EA200201234A1 (ru) | 2003-04-24 |
| CN1429205A (zh) | 2003-07-09 |
| EP1311474A1 (en) | 2003-05-21 |
| MXPA02010020A (es) | 2003-02-12 |
| ECSP014078A (es) | 2002-02-25 |
| CZ20023797A3 (cs) | 2003-04-16 |
| US20030225163A1 (en) | 2003-12-04 |
| SK16312002A3 (sk) | 2003-05-02 |
| JP2003534316A (ja) | 2003-11-18 |
| DZ3343A1 (fr) | 2001-11-29 |
| CA2409830A1 (en) | 2001-11-29 |
| IL152156A0 (en) | 2003-05-29 |
| HUP0302255A2 (hu) | 2003-11-28 |
| NO20025459L (no) | 2002-11-14 |
| AR035915A1 (es) | 2004-07-28 |
| KR20030007644A (ko) | 2003-01-23 |
| HUP0302255A3 (en) | 2005-11-28 |
| BR0110874A (pt) | 2003-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |