HRP20010800A2 - Monofluoroalkyl derivatives - Google Patents
Monofluoroalkyl derivatives Download PDFInfo
- Publication number
- HRP20010800A2 HRP20010800A2 HR20010800A HRP20010800A HRP20010800A2 HR P20010800 A2 HRP20010800 A2 HR P20010800A2 HR 20010800 A HR20010800 A HR 20010800A HR P20010800 A HRP20010800 A HR P20010800A HR P20010800 A2 HRP20010800 A2 HR P20010800A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- phenyl
- fluoro
- sulfonyl
- methylethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 394
- -1 hydroxyimino Chemical group 0.000 claims description 265
- 125000000217 alkyl group Chemical group 0.000 claims description 237
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 113
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 80
- 125000003342 alkenyl group Chemical group 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 229910052760 oxygen Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- YSFHKDMKZLYLQP-UHFFFAOYSA-N n-[2-fluoro-2-(4-iodophenyl)propyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NCC(C)(F)C1=CC=C(I)C=C1 YSFHKDMKZLYLQP-UHFFFAOYSA-N 0.000 claims description 27
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 22
- 125000002837 carbocyclic group Chemical group 0.000 claims description 21
- 125000002393 azetidinyl group Chemical group 0.000 claims description 20
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000003386 piperidinyl group Chemical group 0.000 claims description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 102000018899 Glutamate Receptors Human genes 0.000 claims description 15
- 108010027915 Glutamate Receptors Proteins 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 230000006870 function Effects 0.000 claims description 11
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 11
- ZCSCWIGOJVPVOQ-UHFFFAOYSA-N 4-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]benzoic acid Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(C(O)=O)C=C1 ZCSCWIGOJVPVOQ-UHFFFAOYSA-N 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- 230000003389 potentiating effect Effects 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 9
- MFJKNXILEXBWNQ-UHFFFAOYSA-N 4-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C(C(C)(F)CNS(=O)(=O)C(C)C)C=C1 MFJKNXILEXBWNQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- JFKBJNURVJGXEJ-UHFFFAOYSA-N n-[2-[4-(3-aminophenyl)phenyl]-2-fluoropropyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=CC(N)=C1 JFKBJNURVJGXEJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 229910052705 radium Inorganic materials 0.000 claims description 7
- 229910052701 rubidium Inorganic materials 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 6
- ZHRDDQVANOLXKJ-UHFFFAOYSA-N n-[2-fluoro-2-[4-[3-(methanesulfonamido)phenyl]phenyl]propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=CC(NS(C)(=O)=O)=C1 ZHRDDQVANOLXKJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 5
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 5
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 5
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 5
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 5
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 5
- 125000005072 dihydrothiopyranyl group Chemical group S1C(CCC=C1)* 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 5
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 235000019256 formaldehyde Nutrition 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical compound C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 claims description 4
- FBNSXPWMAZKJSV-UHFFFAOYSA-N 1-[1-(dimethylsulfamoylamino)-2-fluoropropan-2-yl]-4-iodobenzene Chemical compound CN(C)S(=O)(=O)NCC(C)(F)C1=CC=C(I)C=C1 FBNSXPWMAZKJSV-UHFFFAOYSA-N 0.000 claims description 3
- XJFVXJOUKLHZHR-UHFFFAOYSA-N 1-amino-3-[4-[1-(dimethylsulfamoylamino)-2-fluoropropan-2-yl]phenyl]benzene Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)N(C)C)=CC=C1C1=CC=CC(N)=C1 XJFVXJOUKLHZHR-UHFFFAOYSA-N 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- 208000016285 Movement disease Diseases 0.000 claims description 3
- 208000013403 hyperactivity Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- JNLQMKDCVWFOAJ-UHFFFAOYSA-N 3-cyano-n-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]benzamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1NC(=O)C1=CC=CC(C#N)=C1 JNLQMKDCVWFOAJ-UHFFFAOYSA-N 0.000 claims description 2
- IYRSAGDMWNOHLO-UHFFFAOYSA-N 4-(dimethylamino)-n-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]butanamide Chemical compound CC(C)S(=O)(=O)NCC(C)(F)C1=CC=C(NC(=O)CCCN(C)C)C=C1 IYRSAGDMWNOHLO-UHFFFAOYSA-N 0.000 claims description 2
- SFRGAGGGLFWJJZ-UHFFFAOYSA-N 4-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(C(=O)N(C)C)C=C1 SFRGAGGGLFWJJZ-UHFFFAOYSA-N 0.000 claims description 2
- QOOVAUZCHZGNBX-UHFFFAOYSA-N 4-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]benzenesulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(S(N)(=O)=O)C=C1 QOOVAUZCHZGNBX-UHFFFAOYSA-N 0.000 claims description 2
- NAVGNPLSEIJESL-UHFFFAOYSA-N 4-chloro-n-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]benzamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 NAVGNPLSEIJESL-UHFFFAOYSA-N 0.000 claims description 2
- XDXFTISMSNLVMW-UHFFFAOYSA-N 4-cyano-n-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]benzamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1NC(=O)C1=CC=C(C#N)C=C1 XDXFTISMSNLVMW-UHFFFAOYSA-N 0.000 claims description 2
- TYECSHWUZGRODD-UHFFFAOYSA-N 6-chloro-n-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1NC(=O)C1=CC=C(Cl)N=C1 TYECSHWUZGRODD-UHFFFAOYSA-N 0.000 claims description 2
- VODLWZNVTODYEQ-UHFFFAOYSA-N N-[2-fluoro-2-[4-(3-hydrazinylphenyl)phenyl]propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=CC(NN)=C1 VODLWZNVTODYEQ-UHFFFAOYSA-N 0.000 claims description 2
- QVGHMXOYRNYSHT-UHFFFAOYSA-N ethyl n-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(C(C)(F)CNS(=O)(=O)C(C)C)C=C1 QVGHMXOYRNYSHT-UHFFFAOYSA-N 0.000 claims description 2
- CSKVZCDDZVFQIJ-UHFFFAOYSA-N methyl n-[2-[4-[[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]carbamoyl]phenyl]ethyl]carbamate Chemical compound C1=CC(CCNC(=O)OC)=CC=C1C(=O)NC1=CC=C(C(C)(F)CNS(=O)(=O)C(C)C)C=C1 CSKVZCDDZVFQIJ-UHFFFAOYSA-N 0.000 claims description 2
- XDGHYNJGZHESGP-UHFFFAOYSA-N n-[2-[2-fluoro-4-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]phenyl]ethyl]-2-methylpropanamide Chemical compound C1=C(F)C(CCNC(=O)C(C)C)=CC=C1C1=CC=C(C(C)(F)CNS(=O)(=O)C(C)C)C=C1 XDGHYNJGZHESGP-UHFFFAOYSA-N 0.000 claims description 2
- WBHZUZYWINBPJB-UHFFFAOYSA-N n-[2-[2-fluoro-4-[4-[2-fluoro-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]phenyl]ethyl]acetamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(CCNC(C)=O)C(F)=C1 WBHZUZYWINBPJB-UHFFFAOYSA-N 0.000 claims description 2
- JGDRINOZJHSVME-UHFFFAOYSA-N n-[2-[2-fluoro-4-[4-[2-hydroxy-1-(propan-2-ylsulfonylamino)propan-2-yl]phenyl]phenyl]ethyl]propane-2-sulfonamide Chemical compound C1=C(F)C(CCNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(C(C)(O)CNS(=O)(=O)C(C)C)C=C1 JGDRINOZJHSVME-UHFFFAOYSA-N 0.000 claims description 2
- LEWVLJUOJSRJCK-UHFFFAOYSA-N n-[2-[4-(3,5-difluorophenyl)phenyl]-2-fluoropropyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC(F)=CC(F)=C1 LEWVLJUOJSRJCK-UHFFFAOYSA-N 0.000 claims description 2
- XTEMEYWVURHKCN-UHFFFAOYSA-N n-[2-[4-(4-cyanophenyl)phenyl]-2-fluoropropyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(C#N)C=C1 XTEMEYWVURHKCN-UHFFFAOYSA-N 0.000 claims description 2
- DCKMWYCQBXTYMA-UHFFFAOYSA-N n-[2-[4-[(2-cyanophenyl)methoxy]phenyl]-2-fluoropropyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1OCC1=CC=CC=C1C#N DCKMWYCQBXTYMA-UHFFFAOYSA-N 0.000 claims description 2
- XTHOBDIKJPXIFF-UHFFFAOYSA-N n-[2-[4-[(3,5-difluorophenyl)methoxy]phenyl]-2-fluoropropyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1OCC1=CC(F)=CC(F)=C1 XTHOBDIKJPXIFF-UHFFFAOYSA-N 0.000 claims description 2
- XZHMRMPPKPGPMQ-UHFFFAOYSA-N n-[2-[4-[4-(cyanomethyl)phenyl]phenyl]-2-fluoropropyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(CC#N)C=C1 XZHMRMPPKPGPMQ-UHFFFAOYSA-N 0.000 claims description 2
- IJQXQDMOOMMPJA-UHFFFAOYSA-N n-[2-fluoro-2-(4-methoxyphenyl)propyl]propane-2-sulfonamide Chemical compound COC1=CC=C(C(C)(F)CNS(=O)(=O)C(C)C)C=C1 IJQXQDMOOMMPJA-UHFFFAOYSA-N 0.000 claims description 2
- QEKICSNNEXIPMS-UHFFFAOYSA-N n-[2-fluoro-2-(4-phenylmethoxyphenyl)propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1OCC1=CC=CC=C1 QEKICSNNEXIPMS-UHFFFAOYSA-N 0.000 claims description 2
- FRQGUQXJFFPXTA-UHFFFAOYSA-N n-[2-fluoro-2-(4-phenylphenyl)propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=CC=C1 FRQGUQXJFFPXTA-UHFFFAOYSA-N 0.000 claims description 2
- DZHLEXBAUGWNIE-UHFFFAOYSA-N n-[2-fluoro-2-(4-pyridin-3-ylphenyl)propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=CN=C1 DZHLEXBAUGWNIE-UHFFFAOYSA-N 0.000 claims description 2
- AUTOJNGBWNINLD-UHFFFAOYSA-N n-[2-fluoro-2-(4-thiophen-3-ylphenyl)propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CSC=C1 AUTOJNGBWNINLD-UHFFFAOYSA-N 0.000 claims description 2
- IMWPJWFSAYYDMK-UHFFFAOYSA-N n-[2-fluoro-2-[4-(2-oxo-1,3-dihydroindol-6-yl)phenyl]propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(CC(=O)N2)C2=C1 IMWPJWFSAYYDMK-UHFFFAOYSA-N 0.000 claims description 2
- VQZDUTGVTIBHEI-UHFFFAOYSA-N n-[2-fluoro-2-[4-(4-formylphenyl)phenyl]propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(C=O)C=C1 VQZDUTGVTIBHEI-UHFFFAOYSA-N 0.000 claims description 2
- OAYSAUJNGMWIBT-UHFFFAOYSA-N n-[2-fluoro-2-[4-[4-[2-(methanesulfonamido)ethyl]phenyl]phenyl]propyl]propane-2-sulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)C(C)C)=CC=C1C1=CC=C(CCNS(C)(=O)=O)C=C1 OAYSAUJNGMWIBT-UHFFFAOYSA-N 0.000 claims description 2
- QJYFECLMLDWOOR-UHFFFAOYSA-N n-[3-[4-[1-(dimethylsulfamoylamino)-2-fluoropropan-2-yl]phenyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(F)CNS(=O)(=O)N(C)C)=CC=C1C1=CC=CC(NS(C)(=O)=O)=C1 QJYFECLMLDWOOR-UHFFFAOYSA-N 0.000 claims description 2
- KNLQIHHQWXULJS-UHFFFAOYSA-N n-[3-[4-[1-(dimethylsulfamoylamino)-2-fluoropropan-2-yl]phenyl]phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C=2C=CC(=CC=2)C(C)(F)CNS(=O)(=O)N(C)C)=C1 KNLQIHHQWXULJS-UHFFFAOYSA-N 0.000 claims description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 230000003956 synaptic plasticity Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
Classifications
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- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- 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
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- C07C307/04—Diamides of sulfuric acids
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- 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
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- 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
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- C07C311/06—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 carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- 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
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
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- 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
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- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/82—Amides; Imides in position 3
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
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- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US13177199P | 1999-04-30 | 1999-04-30 | |
US17756600P | 2000-01-21 | 2000-01-21 | |
PCT/US2000/008734 WO2000066546A2 (en) | 1999-04-30 | 2000-04-17 | Monofluoroalkyl derivatives |
Publications (1)
Publication Number | Publication Date |
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HRP20010800A2 true HRP20010800A2 (en) | 2002-12-31 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20010800A HRP20010800A2 (en) | 1999-04-30 | 2001-10-29 | Monofluoroalkyl derivatives |
Country Status (29)
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US (1) | US7034045B1 (pt) |
EP (1) | EP1183232B1 (pt) |
JP (1) | JP2002543177A (pt) |
KR (1) | KR20020030268A (pt) |
CN (1) | CN1240677C (pt) |
AR (1) | AR033942A1 (pt) |
AT (1) | ATE374747T1 (pt) |
AU (1) | AU774379B2 (pt) |
BR (1) | BR0010183A (pt) |
CA (1) | CA2372490A1 (pt) |
CZ (1) | CZ20013852A3 (pt) |
DE (1) | DE60036617T2 (pt) |
DZ (1) | DZ3036A1 (pt) |
EA (1) | EA004299B1 (pt) |
ES (1) | ES2292439T3 (pt) |
HR (1) | HRP20010800A2 (pt) |
HU (1) | HUP0201157A3 (pt) |
ID (1) | ID30454A (pt) |
IL (1) | IL146052A0 (pt) |
MX (1) | MXPA01011003A (pt) |
MY (1) | MY127686A (pt) |
NO (1) | NO20015290L (pt) |
NZ (1) | NZ530385A (pt) |
PE (1) | PE20010117A1 (pt) |
PL (1) | PL351991A1 (pt) |
SK (1) | SK15102001A3 (pt) |
SV (1) | SV2002000062A (pt) |
TR (1) | TR200103123T2 (pt) |
WO (1) | WO2000066546A2 (pt) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9702194D0 (en) | 1997-02-04 | 1997-03-26 | Lilly Co Eli | Sulphonide derivatives |
US6693137B1 (en) | 1998-07-31 | 2004-02-17 | Eli Lilly And Company | Sulphonamide derivatives |
US6358981B1 (en) | 1998-07-31 | 2002-03-19 | Eli Lilly And Company | Sulphonamide derivatives |
ATE266400T1 (de) | 1998-07-31 | 2004-05-15 | Lilly Co Eli | Heterocyclyl sulphonamid derivate |
US6639107B1 (en) | 1999-12-08 | 2003-10-28 | Eli Lilly And Company | Cyclopentyl sulfonamide derivatives |
US20030225127A1 (en) * | 2000-08-11 | 2003-12-04 | Bender David Michael | Heterocyclic sulfonamide derivatives |
AU2001280470A1 (en) * | 2000-08-11 | 2002-02-25 | Eli Lilly And Company | Heterocyclic sulfonamide derivatives |
AU2002307327A1 (en) * | 2001-05-04 | 2002-11-18 | Eli Lilly And Company | Use of an ampa receptor potentiator for the manufacture of a medicament for the treatment of type 2 diabetes |
EP1409452A1 (en) * | 2001-06-05 | 2004-04-21 | Eli Lilly And Company | Sulfonamide derivatives |
WO2005013961A1 (en) * | 2003-07-17 | 2005-02-17 | Eli Lilly And Company | Combination therapy for treatment of cognitive disorders or psychoses |
RU2403242C2 (ru) | 2004-08-09 | 2010-11-10 | Глэксо Груп Лимитед | Соединения, которые усиливают рецептор глутамата, и их применение в медицине |
EP1981865A1 (en) * | 2006-02-08 | 2008-10-22 | Glaxo Group Limited | 4-phenyl-3-(2-propylsulfonylamino) tetrahydrofuran derivatives which potentiate glutamate receptors and are useful in the treatment of schizophrenia |
WO2011109398A2 (en) | 2010-03-02 | 2011-09-09 | President And Fellows Of Harvard College | Methods and compositions for treatment of angelman syndrome and autism spectrum disorders |
JP2016521755A (ja) | 2013-06-13 | 2016-07-25 | ヴェロサイエンス,リミテッド・ライアビリティー・カンパニー | 代謝障害を治療するための組成物および方法 |
EP3119755B1 (en) * | 2014-03-19 | 2019-03-06 | Viamet Pharmaceuticals (NC), Inc. | Antifungal compound process |
EP3119764B1 (en) * | 2014-03-19 | 2019-04-17 | Viamet Pharmaceuticals (NC), Inc. | Antifungal compound process |
CN109678812B (zh) * | 2018-12-30 | 2022-09-02 | 天津大学 | 一种5-乙烯基-2-硫代恶唑烷的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
US5556990A (en) * | 1994-12-16 | 1996-09-17 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Polyarylcarbamoylaza- and -carbamoylalkanedioic acids |
GB9702194D0 (en) * | 1997-02-04 | 1997-03-26 | Lilly Co Eli | Sulphonide derivatives |
US6174922B1 (en) | 1998-05-11 | 2001-01-16 | Eli Lilly And Company | Sulphonamide derivatives |
US6358981B1 (en) * | 1998-07-31 | 2002-03-19 | Eli Lilly And Company | Sulphonamide derivatives |
ATE266400T1 (de) | 1998-07-31 | 2004-05-15 | Lilly Co Eli | Heterocyclyl sulphonamid derivate |
PE20000943A1 (es) | 1998-07-31 | 2000-09-28 | Lilly Co Eli | Derivados de sulfonamida |
PE20000944A1 (es) | 1998-07-31 | 2000-09-20 | Lilly Co Eli | Derivados de sulfonamida |
PE20000942A1 (es) | 1998-07-31 | 2000-09-28 | Lilly Co Eli | Derivados de amida, carbamato y urea |
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2000
- 2000-04-17 IL IL14605200A patent/IL146052A0/xx unknown
- 2000-04-17 CN CNB008069980A patent/CN1240677C/zh not_active Expired - Fee Related
- 2000-04-17 EA EA200101160A patent/EA004299B1/ru not_active IP Right Cessation
- 2000-04-17 JP JP2000615377A patent/JP2002543177A/ja not_active Withdrawn
- 2000-04-17 AU AU43289/00A patent/AU774379B2/en not_active Ceased
- 2000-04-17 ES ES00923110T patent/ES2292439T3/es not_active Expired - Lifetime
- 2000-04-17 SK SK1510-2001A patent/SK15102001A3/sk unknown
- 2000-04-17 WO PCT/US2000/008734 patent/WO2000066546A2/en active IP Right Grant
- 2000-04-17 TR TR2001/03123T patent/TR200103123T2/xx unknown
- 2000-04-17 CZ CZ20013852A patent/CZ20013852A3/cs unknown
- 2000-04-17 HU HU0201157A patent/HUP0201157A3/hu unknown
- 2000-04-17 EP EP00923110A patent/EP1183232B1/en not_active Expired - Lifetime
- 2000-04-17 KR KR1020017013868A patent/KR20020030268A/ko active IP Right Grant
- 2000-04-17 BR BR0010183-4A patent/BR0010183A/pt not_active IP Right Cessation
- 2000-04-17 AT AT00923110T patent/ATE374747T1/de not_active IP Right Cessation
- 2000-04-17 DE DE60036617T patent/DE60036617T2/de not_active Expired - Lifetime
- 2000-04-17 US US09/958,262 patent/US7034045B1/en not_active Expired - Fee Related
- 2000-04-17 CA CA002372490A patent/CA2372490A1/en not_active Abandoned
- 2000-04-17 ID IDW00200102364A patent/ID30454A/id unknown
- 2000-04-17 MX MXPA01011003A patent/MXPA01011003A/es unknown
- 2000-04-17 NZ NZ530385A patent/NZ530385A/en unknown
- 2000-04-17 PL PL00351991A patent/PL351991A1/xx not_active Application Discontinuation
- 2000-04-26 DZ DZ000078A patent/DZ3036A1/xx active
- 2000-04-27 AR ARP000102010A patent/AR033942A1/es unknown
- 2000-04-27 MY MYPI20001799A patent/MY127686A/en unknown
- 2000-04-28 SV SV2000000062A patent/SV2002000062A/es not_active Application Discontinuation
- 2000-04-28 PE PE2000000402A patent/PE20010117A1/es not_active Application Discontinuation
-
2001
- 2001-10-29 HR HR20010800A patent/HRP20010800A2/hr not_active Application Discontinuation
- 2001-10-29 NO NO20015290A patent/NO20015290L/no not_active Application Discontinuation
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