CA2205586A1 - Propanones 1-aryl-3-piperazin-1'-yle substituees - Google Patents
Propanones 1-aryl-3-piperazin-1'-yle substitueesInfo
- Publication number
- CA2205586A1 CA2205586A1 CA 2205586 CA2205586A CA2205586A1 CA 2205586 A1 CA2205586 A1 CA 2205586A1 CA 2205586 CA2205586 CA 2205586 CA 2205586 A CA2205586 A CA 2205586A CA 2205586 A1 CA2205586 A1 CA 2205586A1
- Authority
- CA
- Canada
- Prior art keywords
- piperazinyl
- hydrogen
- benzyl
- loweralkyl
- propanone
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 157
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 148
- 239000001257 hydrogen Substances 0.000 claims abstract description 148
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 49
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- -1 amino, acetyl Chemical group 0.000 claims description 116
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 75
- 125000005843 halogen group Chemical group 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000001544 thienyl group Chemical group 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 229910052717 sulfur Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000004656 alkyl sulfonylamino group Chemical group 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 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 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 69
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims 2
- BDKRXMVUCWUNCW-UHFFFAOYSA-N Cl.Cl.C1SC2=CC=CC=C2C(=O)C1CN(CC1)CCN1CC1=CC=CC=C1 Chemical compound Cl.Cl.C1SC2=CC=CC=C2C(=O)C1CN(CC1)CCN1CC1=CC=CC=C1 BDKRXMVUCWUNCW-UHFFFAOYSA-N 0.000 claims 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
- 125000004802 cyanophenyl group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
On décrit des composés de la formule (I) ci-après, ou des sels de ceux-ci acceptables sur le plan pharmacologique, dans laquelle X représente un carbonyle, sulfonyle, méthylène ou méthylène substitué avec du phényle éventuellement substitué; Z représente l'azote ou CH; Ar¿1? et Ar¿2? représentent indépendamment des groupes aryle; et Y représente l'hydrogène; ou Y et R¿1? ou R¿2? représentent ensemble CH¿2?; CH¿2?CH¿2?; CH¿2?0; CH¿2?S formant un noyau à 5 ou 6 chaînons, ce noyau pouvant être éventuellement substitué par de l'alkyle inférieur ou du phényle. Ces composés sont utilisés dans le traitement des maladies néoplastiques et des infections bactériennes ou fongiques, ainsi que pour prévenir ou réduire la production d'épitopes de filaments hélicoïdaux couplés (PHF) anormalement phosphorylés associés à la maladie d'Alzheimer. Ces composés sont donc utilisés également dans le traitement de cette maladie.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/341,507 US5693804A (en) | 1994-11-17 | 1994-11-17 | Substituted 1-aryl-3-piperazin-1'-yl propanones |
| US08/341,507 | 1994-11-17 | ||
| PCT/US1995/014987 WO1996016052A2 (fr) | 1994-11-17 | 1995-11-16 | Propanones 1-aryl-3-piperazin-1'-yle substituees |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2205586A1 true CA2205586A1 (fr) | 1996-05-30 |
Family
ID=29405861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2205586 Abandoned CA2205586A1 (fr) | 1994-11-17 | 1995-11-16 | Propanones 1-aryl-3-piperazin-1'-yle substituees |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2205586A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947928A (zh) * | 2018-07-03 | 2018-12-07 | 江苏大学 | 含氮、氧、氧三取代六元环内脂化合物及制备方法和用途 |
| CN115894195A (zh) * | 2021-09-30 | 2023-04-04 | 迈克斯(如东)化工有限公司 | 一种制备1-芳基-3-取代丙酮类化合物的方法及中间体 |
-
1995
- 1995-11-16 CA CA 2205586 patent/CA2205586A1/fr not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947928A (zh) * | 2018-07-03 | 2018-12-07 | 江苏大学 | 含氮、氧、氧三取代六元环内脂化合物及制备方法和用途 |
| CN108947928B (zh) * | 2018-07-03 | 2022-05-20 | 江苏大学 | 含氮、氧、氧三取代六元环内脂化合物及制备方法和用途 |
| CN115894195A (zh) * | 2021-09-30 | 2023-04-04 | 迈克斯(如东)化工有限公司 | 一种制备1-芳基-3-取代丙酮类化合物的方法及中间体 |
| CN115894195B (zh) * | 2021-09-30 | 2024-12-31 | 迈克斯(如东)化工有限公司 | 一种制备1-芳基-3-取代丙酮类化合物的方法及中间体 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |