SK16312002A3 - Sulfónamidové deriváty - Google Patents
Sulfónamidové deriváty Download PDFInfo
- Publication number
- SK16312002A3 SK16312002A3 SK1631-2002A SK16312002A SK16312002A3 SK 16312002 A3 SK16312002 A3 SK 16312002A3 SK 16312002 A SK16312002 A SK 16312002A SK 16312002 A3 SK16312002 A3 SK 16312002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- phenyl
- formula
- pharmaceutically acceptable
- pharmaceutical composition
- Prior art date
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 abstract description 106
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims description 50
- -1 4- {2 - [(methylsulfonyl) amino] ethyl} phenyl Chemical group 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 229920001223 polyethylene glycol Polymers 0.000 claims description 17
- 102000018899 Glutamate Receptors Human genes 0.000 claims description 12
- 108010027915 Glutamate Receptors Proteins 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000002775 capsule Substances 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 229920002562 Polyethylene Glycol 3350 Polymers 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000003389 potentiating effect Effects 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 239000005022 packaging material Substances 0.000 claims description 6
- 230000007278 cognition impairment Effects 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000007903 gelatin capsule Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000001149 cognitive effect Effects 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 229940050929 polyethylene glycol 3350 Drugs 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 abstract description 19
- 229930195712 glutamate Natural products 0.000 abstract description 18
- 208000012902 Nervous system disease Diseases 0.000 abstract description 3
- 208000025966 Neurological disease Diseases 0.000 abstract description 3
- 208000020016 psychiatric disease Diseases 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 238000003756 stirring Methods 0.000 description 34
- 239000007787 solid Substances 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 31
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 29
- 239000012074 organic phase Substances 0.000 description 28
- 239000003960 organic solvent Substances 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 21
- 239000000725 suspension Substances 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 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
- 150000003141 primary amines Chemical class 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
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 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
- 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
- 239000002585 base Substances 0.000 description 8
- 239000012458 free base Substances 0.000 description 8
- 230000006870 function Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 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
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 5
- 208000028017 Psychotic disease Diseases 0.000 description 5
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- 210000002569 neuron Anatomy 0.000 description 5
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- 229910000027 potassium carbonate Inorganic materials 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
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- 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
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- HKDGEKJGALNMPF-UHFFFAOYSA-N [4-[2-(methanesulfonamido)ethyl]phenyl]boronic acid Chemical compound CS(=O)(=O)NCCC1=CC=C(B(O)O)C=C1 HKDGEKJGALNMPF-UHFFFAOYSA-N 0.000 description 4
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- 229910052740 iodine Inorganic materials 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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- 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 3
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- PBEZJWDXAZCWKF-UHFFFAOYSA-N tert-butyl n-methylsulfonyl-n-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=CC(CCN(C(=O)OC(C)(C)C)S(C)(=O)=O)=CC=C1B1OC(C)(C)C(C)(C)O1 PBEZJWDXAZCWKF-UHFFFAOYSA-N 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
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 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)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20600300P | 2000-05-19 | 2000-05-19 | |
| PCT/US2001/011747 WO2001090057A1 (en) | 2000-05-19 | 2001-05-04 | Sulfonamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK16312002A3 true SK16312002A3 (sk) | 2003-05-02 |
Family
ID=22764580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1631-2002A SK16312002A3 (sk) | 2000-05-19 | 2001-05-04 | Sulfónamidové deriváty |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20030225163A1 (zh) |
| EP (1) | EP1311474A1 (zh) |
| JP (1) | JP2003534316A (zh) |
| KR (1) | KR20030007644A (zh) |
| CN (1) | CN1429205A (zh) |
| AR (1) | AR035915A1 (zh) |
| AU (1) | AU2001259053A1 (zh) |
| BR (1) | BR0110874A (zh) |
| CA (1) | CA2409830A1 (zh) |
| CZ (1) | CZ20023797A3 (zh) |
| DZ (1) | DZ3343A1 (zh) |
| EA (1) | EA200201234A1 (zh) |
| EC (1) | ECSP014078A (zh) |
| HR (1) | HRP20020918A2 (zh) |
| HU (1) | HUP0302255A3 (zh) |
| IL (1) | IL152156A0 (zh) |
| MX (1) | MXPA02010020A (zh) |
| NO (1) | NO20025459D0 (zh) |
| PE (1) | PE20020052A1 (zh) |
| PL (1) | PL358180A1 (zh) |
| SK (1) | SK16312002A3 (zh) |
| SV (1) | SV2002000459A (zh) |
| WO (1) | WO2001090057A1 (zh) |
| ZA (1) | ZA200208749B (zh) |
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 |
| WO2003032974A2 (en) * | 2001-10-12 | 2003-04-24 | Eli Lilly And Company | 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 |
| EA015600B1 (ru) * | 2006-12-11 | 2011-10-31 | Эли Лилли Энд Компани | Агенты, усиливающие действие амра-рецепторов |
| CA2915405A1 (en) | 2013-06-13 | 2014-12-18 | Veroscience Llc | Compositions and methods for treating metabolic disorders |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5235599A (en) * | 1998-07-31 | 2000-02-21 | Eli Lilly And Company | N-substituted sulfonamide derivatives |
-
2001
- 2001-05-04 EA EA200201234A patent/EA200201234A1/ru unknown
- 2001-05-04 HU HU0302255A patent/HUP0302255A3/hu unknown
- 2001-05-04 JP JP2001586247A patent/JP2003534316A/ja not_active Withdrawn
- 2001-05-04 IL IL15215601A patent/IL152156A0/xx unknown
- 2001-05-04 EP EP01932536A patent/EP1311474A1/en not_active Withdrawn
- 2001-05-04 AU AU2001259053A patent/AU2001259053A1/en not_active Abandoned
- 2001-05-04 US US10/258,159 patent/US20030225163A1/en not_active Abandoned
- 2001-05-04 CN CN01809667A patent/CN1429205A/zh active Pending
- 2001-05-04 CZ CZ20023797A patent/CZ20023797A3/cs unknown
- 2001-05-04 CA CA002409830A patent/CA2409830A1/en not_active Abandoned
- 2001-05-04 WO PCT/US2001/011747 patent/WO2001090057A1/en not_active Application Discontinuation
- 2001-05-04 BR BR0110874-3A patent/BR0110874A/pt not_active Application Discontinuation
- 2001-05-04 DZ DZ013343A patent/DZ3343A1/fr active
- 2001-05-04 KR KR1020027015545A patent/KR20030007644A/ko not_active Application Discontinuation
- 2001-05-04 PL PL01358180A patent/PL358180A1/xx not_active Application Discontinuation
- 2001-05-04 SK SK1631-2002A patent/SK16312002A3/sk unknown
- 2001-05-04 MX MXPA02010020A patent/MXPA02010020A/es unknown
- 2001-05-18 PE PE2001000451A patent/PE20020052A1/es 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 EC EC2001004078A patent/ECSP014078A/es unknown
-
2002
- 2002-10-29 ZA ZA200208749A patent/ZA200208749B/en unknown
- 2002-11-14 NO NO20025459A patent/NO20025459D0/no not_active Application Discontinuation
- 2002-11-19 HR HR20020918A patent/HRP20020918A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20025459L (no) | 2002-11-14 |
| SV2002000459A (es) | 2002-07-03 |
| DZ3343A1 (fr) | 2001-11-29 |
| EA200201234A1 (ru) | 2003-04-24 |
| MXPA02010020A (es) | 2003-02-12 |
| CA2409830A1 (en) | 2001-11-29 |
| HUP0302255A3 (en) | 2005-11-28 |
| NO20025459D0 (no) | 2002-11-14 |
| ECSP014078A (es) | 2002-02-25 |
| CZ20023797A3 (cs) | 2003-04-16 |
| US20030225163A1 (en) | 2003-12-04 |
| WO2001090057A1 (en) | 2001-11-29 |
| CN1429205A (zh) | 2003-07-09 |
| PL358180A1 (en) | 2004-08-09 |
| HRP20020918A2 (en) | 2004-02-29 |
| HUP0302255A2 (hu) | 2003-11-28 |
| IL152156A0 (en) | 2003-05-29 |
| BR0110874A (pt) | 2003-02-11 |
| JP2003534316A (ja) | 2003-11-18 |
| KR20030007644A (ko) | 2003-01-23 |
| EP1311474A1 (en) | 2003-05-21 |
| AR035915A1 (es) | 2004-07-28 |
| ZA200208749B (en) | 2004-01-30 |
| PE20020052A1 (es) | 2002-02-02 |
| AU2001259053A1 (en) | 2001-12-03 |
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