LT4838B - 1,3,4-oksadiazolono dariniai - Google Patents
1,3,4-oksadiazolono dariniai Download PDFInfo
- Publication number
- LT4838B LT4838B LT2000068A LT2000068A LT4838B LT 4838 B LT4838 B LT 4838B LT 2000068 A LT2000068 A LT 2000068A LT 2000068 A LT2000068 A LT 2000068A LT 4838 B LT4838 B LT 4838B
- Authority
- LT
- Lithuania
- Prior art keywords
- methyl
- phenyl
- chloro
- trifluoromethyl
- oxadiazol
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 208000035475 disorder Diseases 0.000 claims abstract description 19
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 17
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 17
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 100
- -1 4-chloro-2 - [[5- [4- (trifluoromethyl) phenyl] -2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl] methyl] phenyl (dimethylamino) Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 239000011575 calcium Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 208000006011 Stroke Diseases 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 206010010904 Convulsion Diseases 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
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- 206010027599 migraine Diseases 0.000 claims description 7
- GWVLAXGYZUVAGV-UHFFFAOYSA-N n,n-dimethylmethanamine;methanesulfonic acid Chemical compound C[NH+](C)C.CS([O-])(=O)=O GWVLAXGYZUVAGV-UHFFFAOYSA-N 0.000 claims description 7
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
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- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 102000005702 Calcium-Activated Potassium Channels Human genes 0.000 claims description 2
- 108010045489 Calcium-Activated Potassium Channels Proteins 0.000 claims description 2
- SUGURSDJQFUZOY-UHFFFAOYSA-M [2-[4-chloro-2-[[2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]phenoxy]-2-oxoethyl]-trimethylazanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C[N+](C)(C)CC(=O)OC1=CC=C(Cl)C=C1CN1C(=O)OC(C=2C=CC(=CC=2)C(F)(F)F)=N1 SUGURSDJQFUZOY-UHFFFAOYSA-M 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- MGOYBMFCELTAHS-UHFFFAOYSA-N methyl 3-(diethylamino)propanoate Chemical compound CCN(CC)CCC(=O)OC MGOYBMFCELTAHS-UHFFFAOYSA-N 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- VEQZOIFDBXAUBE-UHFFFAOYSA-M ethyl(trimethyl)azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.CC[N+](C)(C)C VEQZOIFDBXAUBE-UHFFFAOYSA-M 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 1
- 108010092555 Large-Conductance Calcium-Activated Potassium Channels Proteins 0.000 abstract description 20
- 102000016469 Large-Conductance Calcium-Activated Potassium Channels Human genes 0.000 abstract description 20
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 32
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
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- 238000000034 method Methods 0.000 description 19
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- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 10
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
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- 239000004480 active ingredient Substances 0.000 description 7
- 210000000170 cell membrane Anatomy 0.000 description 7
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 7
- 230000003834 intracellular effect Effects 0.000 description 7
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- 230000001225 therapeutic effect Effects 0.000 description 7
- WTSXVIMLKCKWIW-UHFFFAOYSA-N 3h-1,3,4-oxadiazol-2-one Chemical compound O=C1NN=CO1 WTSXVIMLKCKWIW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- 238000001704 evaporation Methods 0.000 description 6
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
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- 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 description 5
- QKOWACXSXTXRKA-UHFFFAOYSA-N 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-one Chemical class OC1=CC=C(Cl)C=C1CN1C(=O)OC(C=2C=CC(=CC=2)C(F)(F)F)=N1 QKOWACXSXTXRKA-UHFFFAOYSA-N 0.000 description 4
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- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
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- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
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- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
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- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
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US7296698P | 1998-01-29 | 1998-01-29 | |
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LT2000068A LT2000068A (en) | 2001-03-26 |
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LT2000068A LT4838B (lt) | 1998-01-29 | 2000-07-14 | 1,3,4-oksadiazolono dariniai |
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US (1) | US6034113A (sk) |
EP (1) | EP1051173A4 (sk) |
JP (1) | JP2002527352A (sk) |
KR (1) | KR20010077838A (sk) |
CN (1) | CN1150175C (sk) |
AR (1) | AR010712A1 (sk) |
AU (1) | AU735704B2 (sk) |
BG (1) | BG104706A (sk) |
BR (1) | BR9913010A (sk) |
CA (1) | CA2318830A1 (sk) |
CO (1) | CO5090837A1 (sk) |
EE (1) | EE04089B1 (sk) |
GE (1) | GEP20032914B (sk) |
HU (1) | HUP0102025A3 (sk) |
ID (1) | ID26909A (sk) |
IL (1) | IL137518A0 (sk) |
LT (1) | LT4838B (sk) |
LV (1) | LV12559B (sk) |
NO (1) | NO317102B1 (sk) |
NZ (1) | NZ505409A (sk) |
PL (1) | PL342060A1 (sk) |
RU (1) | RU2202548C2 (sk) |
SK (1) | SK10852000A3 (sk) |
TR (1) | TR200002019T2 (sk) |
TW (1) | TW550075B (sk) |
UA (1) | UA58579C2 (sk) |
WO (1) | WO1999038510A1 (sk) |
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CN104710379B (zh) * | 2015-03-09 | 2017-01-18 | 华南理工大学 | 一种bms‑191011的合成方法 |
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