UA79286C2 - Arylcarbonylpipererazines and heteroarylcarbonylpiperazines and their use in the treatment of benign and malignant tumors - Google Patents
Arylcarbonylpipererazines and heteroarylcarbonylpiperazines and their use in the treatment of benign and malignant tumors Download PDFInfo
- Publication number
- UA79286C2 UA79286C2 UA20041210297A UA20041210297A UA79286C2 UA 79286 C2 UA79286 C2 UA 79286C2 UA 20041210297 A UA20041210297 A UA 20041210297A UA 20041210297 A UA20041210297 A UA 20041210297A UA 79286 C2 UA79286 C2 UA 79286C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- aryl
- alkylaryl
- heteroaryl
- alkylheteroaryl
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 11
- 201000011510 cancer Diseases 0.000 title claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 45
- -1 cycloalkyl radical Chemical class 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 22
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 241000282412 Homo Species 0.000 claims description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 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 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 239000011734 sodium Substances 0.000 claims description 3
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- LQDYHFHELYNWSU-UHFFFAOYSA-N 3h-fluorene Chemical compound C1=CC=C2C3=CCC=CC3=CC2=C1 LQDYHFHELYNWSU-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002015 acyclic group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
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- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
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- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
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- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 239000003744 tubulin modulator Substances 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39302702P | 2002-06-29 | 2002-06-29 | |
| PCT/EP2003/006555 WO2004002965A1 (de) | 2002-06-29 | 2003-06-20 | Aryl- und heteroarylcarbonylpiperazine und deren verwendung zur behandlung gutartiger und bösartiger tumorerkrankungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79286C2 true UA79286C2 (en) | 2007-06-11 |
Family
ID=30000964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20041210297A UA79286C2 (en) | 2002-06-29 | 2003-06-20 | Arylcarbonylpipererazines and heteroarylcarbonylpiperazines and their use in the treatment of benign and malignant tumors |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20040097734A1 (de) |
| EP (1) | EP1517898A1 (de) |
| JP (1) | JP2005538968A (de) |
| CN (1) | CN100509790C (de) |
| AR (1) | AR040315A1 (de) |
| AU (1) | AU2003246571B2 (de) |
| BR (1) | BR0312294A (de) |
| CA (1) | CA2433983A1 (de) |
| HK (1) | HK1080840A1 (de) |
| HR (1) | HRP20050092A2 (de) |
| MX (1) | MXPA04012959A (de) |
| NO (1) | NO20050428L (de) |
| NZ (1) | NZ537916A (de) |
| PL (1) | PL375527A1 (de) |
| RU (1) | RU2335496C2 (de) |
| UA (1) | UA79286C2 (de) |
| WO (1) | WO2004002965A1 (de) |
| ZA (1) | ZA200409610B (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004218260A1 (en) * | 2003-01-28 | 2004-09-16 | Aventis Pharma S.A. | N-aryl heteroaromatic products, compositions containing same and use thereof |
| MXPA05011775A (es) * | 2003-05-01 | 2006-02-17 | Abbott Lab | Sulfonamidas y pirazolamidas como moduladores de canal de sodio. |
| PE20050226A1 (es) * | 2003-06-04 | 2005-05-18 | Aventis Pharma Sa | Productos aril-heteroaromaticos y composiciones que los contienen |
| FR2855825B1 (fr) * | 2003-06-04 | 2008-08-22 | Aventis Pharma Sa | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| EP1645556A1 (de) * | 2004-10-07 | 2006-04-12 | Boehringer Ingelheim International GmbH | Arylpiperazin-Benzoylamidderivate geeignet als Arzneimittelwirkstoffe |
| US7781462B2 (en) | 2005-07-25 | 2010-08-24 | Synta Pharmaceuticals Corp. | Compounds for the treatment of proliferative disorders |
| EP2051977A2 (de) * | 2006-07-20 | 2009-04-29 | Amgen Inc. | SUBSTITUIERTE AROMATISCHE AZOL-HETEROCYCLEN ALS LLbeta-HSD-1-HEMMER |
| KR100932093B1 (ko) | 2006-09-27 | 2009-12-16 | 주식회사종근당 | 미세소관 형성 저해제로서 유용한 벤조페논 유도체 |
| AU2008288537B2 (en) * | 2007-08-13 | 2011-03-24 | F. Hoffmann-La Roche Ag | Novel piperazine amide derivatives |
| CN101597278B (zh) | 2008-06-04 | 2013-04-17 | 中国中化股份有限公司 | 酰胺类化合物及其制备与应用 |
| US9212177B2 (en) * | 2009-08-05 | 2015-12-15 | Versitech Limited | Antiviral compounds and methods of making and using thereof |
| US20120149715A1 (en) * | 2010-05-28 | 2012-06-14 | Yi Tsun Richard Kao | Compounds and methods for the treatment of viral infections |
| KR101369584B1 (ko) * | 2011-04-19 | 2014-03-06 | 일양약품주식회사 | 페닐-이속사졸 유도체 및 그의 제조방법 |
| CA3034211A1 (en) * | 2016-08-18 | 2018-02-22 | Vidac Pharma Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
| EP3565555A4 (de) * | 2016-11-07 | 2021-03-17 | VIDAC Pharma Ltd. | Verwendung von hexkinase 2/mitochondrien-trennungsverbindungen zur behandlung von hexkinase-2 (hk2)-exprimierenden krebserkrankungen |
| WO2018083704A1 (en) | 2016-11-07 | 2018-05-11 | Vidac Pharma Ltd. | Use of hexokinase 2/mitochondria-detaching compounds for activating immune responses |
| RU2700576C1 (ru) * | 2019-05-07 | 2019-09-18 | Федеральное государственное бюджетное научное учреждение "Институт экспериментальной медицины" (ФГБНУ "ИЭМ") | Анксиолитическое средство |
| CN111303132B (zh) * | 2020-03-19 | 2023-05-23 | 辽宁孚音生物科技有限公司 | 一种抗癌化合物及其制备方法和应用 |
| CN116322544A (zh) * | 2020-08-12 | 2023-06-23 | 云杉生物科学公司 | 用于治疗多囊卵巢综合征的方法和组合物 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1620016C3 (de) * | 1966-07-02 | 1979-08-30 | Merck Patent Gmbh, 6100 Darmstadt | 3-{Piperazinoalkyl)-pyrazole und Verfahren zu ihrer Herstellung |
| US3468882A (en) * | 1966-10-07 | 1969-09-23 | Sterling Drug Inc | Phenylhydrazone derivatives as intermediates for preparing indoles |
| BE791501A (fr) * | 1971-11-19 | 1973-05-17 | Albert Ag Chem Werke | Diamines cycliques n,n'-disubstituees et leur procede de preparation |
| CA1081228A (en) * | 1976-02-18 | 1980-07-08 | Richard A. Partyka | Oxazole, isoxazole, thiazole and isothiazole amides |
| JPS6477A (en) * | 1987-03-24 | 1989-01-05 | Takeda Chem Ind Ltd | 1,4-disubstituted piperazine compound |
| EP0385043A1 (de) * | 1989-02-28 | 1990-09-05 | Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes) | 4-Substituierte Piperazinderivate |
| JPH03218371A (ja) * | 1989-08-02 | 1991-09-25 | Takeda Chem Ind Ltd | ピラゾール誘導体 |
| US5563142A (en) * | 1989-12-28 | 1996-10-08 | The Upjohn Company | Diaromatic substituted compounds as anti-HIV-1 agents |
| EP0552245A1 (de) * | 1990-10-10 | 1993-07-28 | Schering Corporation | Bis-benzo cyclohepta piperidyliden, piperidin und piperazinverbindungen, zusammensetzungen und ihre verwendung |
| DE4219247A1 (de) * | 1992-06-12 | 1993-12-16 | Bayer Ag | Verwendung von 3-arylsubstituierten 5-Alkyl-isoxazol-4-carbonsäurederivaten zur Bekämpfung von Endoparasiten, neue 3-arylsubstituierte 5-Alkyl-isoxazol-4-carbonsäurederivate und Verfahren zu ihrer Herstellung |
| WO1994024095A1 (en) * | 1993-04-16 | 1994-10-27 | Abbott Laboratories | Immunosuppressive agents |
| US6262059B1 (en) * | 1995-06-07 | 2001-07-17 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with quinazoline derivatives |
| WO1998000402A1 (en) * | 1996-06-29 | 1998-01-08 | Samjin Pharmaceutical Co., Ltd. | Piperazine derivatives and process for the preparation thereof |
| ES2125206B1 (es) * | 1997-07-21 | 1999-11-16 | Esteve Labor Dr | Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos. |
| US6166203A (en) * | 1998-02-26 | 2000-12-26 | Neurogen Corporation | Heterocyclic amino substituted heteroaryl fused pyridines; GABA brain receptor ligands |
| KR100659007B1 (ko) * | 1999-02-10 | 2007-02-28 | 미츠비시 웰파마 가부시키가이샤 | 아미드 화합물 및 그 의약으로서의 용도 |
| CA2362495A1 (en) * | 1999-03-03 | 2000-09-08 | Theresa M. Williams | Inhibitors of prenyl-protein transferases |
| IL148698A0 (en) * | 1999-09-17 | 2002-09-12 | Cor Therapeutics Inc | INHIBITORS OF FACTOR Xa |
| DE10035927A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10035908A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10035928A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| AU2001288617A1 (en) * | 2000-09-05 | 2002-03-22 | Neogenesis Pharmaceuticals Inc. | Methods for forming combinatorial libraries combining amide bond formation with epoxide opening |
| US20020072081A1 (en) * | 2000-09-06 | 2002-06-13 | Wai-Si Eng | Geranylgeranyl transferase inhibitor screening assay |
| FR2815032B1 (fr) * | 2000-10-10 | 2003-08-08 | Pf Medicament | Nouveaux derives d'aminophenyle piperazine ou d'amino phenyle piperide inhibiteurs de proteines prenyl transferase ainsi que leurs preparations |
| DE10102053A1 (de) * | 2001-01-17 | 2002-07-18 | Merck Patent Gmbh | Piperazinylcarbonylchinoline und -isochinoline |
| ES2180456B1 (es) * | 2001-07-20 | 2004-05-01 | Laboratorios S.A.L.V.A.T., S.A. | Isoxazoles sustituidos y su utilizacion como antibioticos. |
| US6916804B2 (en) * | 2001-12-20 | 2005-07-12 | Osi Pharmaceuticals, Inc. | Pyrimidine A2b selective antagonist compounds, their synthesis and use |
-
2003
- 2003-06-20 MX MXPA04012959A patent/MXPA04012959A/es active IP Right Grant
- 2003-06-20 EP EP03761482A patent/EP1517898A1/de not_active Withdrawn
- 2003-06-20 RU RU2005102478/04A patent/RU2335496C2/ru not_active IP Right Cessation
- 2003-06-20 WO PCT/EP2003/006555 patent/WO2004002965A1/de active IP Right Grant
- 2003-06-20 PL PL03375527A patent/PL375527A1/xx not_active Application Discontinuation
- 2003-06-20 JP JP2004516632A patent/JP2005538968A/ja active Pending
- 2003-06-20 AU AU2003246571A patent/AU2003246571B2/en not_active Ceased
- 2003-06-20 BR BR0312294-8A patent/BR0312294A/pt not_active IP Right Cessation
- 2003-06-20 NZ NZ537916A patent/NZ537916A/en unknown
- 2003-06-20 CN CNB038154854A patent/CN100509790C/zh not_active Expired - Fee Related
- 2003-06-20 UA UA20041210297A patent/UA79286C2/uk unknown
- 2003-06-27 CA CA002433983A patent/CA2433983A1/en not_active Abandoned
- 2003-06-27 AR ARP030102359A patent/AR040315A1/es unknown
- 2003-06-27 US US10/608,520 patent/US20040097734A1/en not_active Abandoned
-
2004
- 2004-11-26 ZA ZA2004/09610A patent/ZA200409610B/en unknown
-
2005
- 2005-01-25 NO NO20050428A patent/NO20050428L/no not_active Application Discontinuation
- 2005-01-27 HR HR20050092A patent/HRP20050092A2/hr not_active Application Discontinuation
-
2006
- 2006-01-13 HK HK06100574.8A patent/HK1080840A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ537916A (en) | 2005-11-25 |
| CN100509790C (zh) | 2009-07-08 |
| AU2003246571B2 (en) | 2008-06-26 |
| HRP20050092A2 (en) | 2005-02-28 |
| EP1517898A1 (de) | 2005-03-30 |
| PL375527A1 (en) | 2005-11-28 |
| RU2335496C2 (ru) | 2008-10-10 |
| CN1665792A (zh) | 2005-09-07 |
| HK1080840A1 (en) | 2006-05-04 |
| MXPA04012959A (es) | 2005-05-16 |
| WO2004002965A1 (de) | 2004-01-08 |
| NO20050428L (no) | 2005-01-25 |
| BR0312294A (pt) | 2005-04-12 |
| ZA200409610B (en) | 2005-05-25 |
| US20040097734A1 (en) | 2004-05-20 |
| AU2003246571A1 (en) | 2004-01-19 |
| RU2005102478A (ru) | 2005-07-20 |
| JP2005538968A (ja) | 2005-12-22 |
| CA2433983A1 (en) | 2003-12-29 |
| AR040315A1 (es) | 2005-03-23 |
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