HUP0301857A2 - 3(5)-Ureido-pirazol-származékok, eljárás elżállításukra alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények - Google Patents
3(5)-Ureido-pirazol-származékok, eljárás elżállításukra alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények Download PDFInfo
- Publication number
- HUP0301857A2 HUP0301857A2 HU0301857A HUP0301857A HUP0301857A2 HU P0301857 A2 HUP0301857 A2 HU P0301857A2 HU 0301857 A HU0301857 A HU 0301857A HU P0301857 A HUP0301857 A HU P0301857A HU P0301857 A2 HUP0301857 A2 HU P0301857A2
- Authority
- HU
- Hungary
- Prior art keywords
- pyrazol
- urea
- cyclopropyl
- amino
- alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 45
- 230000008569 process Effects 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 26
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 119
- -1 nitro- Chemical class 0.000 claims description 101
- 239000004202 carbamide Substances 0.000 claims description 97
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
- XAEGRAIWWBXIRR-UHFFFAOYSA-N 1h-pyrazol-5-ylurea Chemical class NC(=O)NC=1C=CNN=1 XAEGRAIWWBXIRR-UHFFFAOYSA-N 0.000 claims description 25
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 25
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
- 210000004027 cell Anatomy 0.000 claims description 14
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 13
- 102000016736 Cyclin Human genes 0.000 claims description 13
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
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- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- XDIRCIUYUWHOIO-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylmethyl)-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 XDIRCIUYUWHOIO-UHFFFAOYSA-N 0.000 claims description 4
- HPEUFTOMXSOAMP-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenyl]-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCN(C(=O)NC=2NN=C(CCC=3C=CC=CC=3)C=2)CC1 HPEUFTOMXSOAMP-UHFFFAOYSA-N 0.000 claims description 4
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- LJWNEBAMSQLONR-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 LJWNEBAMSQLONR-UHFFFAOYSA-N 0.000 claims description 3
- CIKLACCMPIJWLU-UHFFFAOYSA-N 1-(4-hydroxybutyl)-3-[5-(2-phenylethyl)-1h-pyrazol-3-yl]urea Chemical compound N1N=C(NC(=O)NCCCCO)C=C1CCC1=CC=CC=C1 CIKLACCMPIJWLU-UHFFFAOYSA-N 0.000 claims description 3
- LPAQWHHDOXAKNP-UHFFFAOYSA-N 1-(5-cyclopentyl-1h-pyrazol-3-yl)-3-(2-phenylethyl)urea Chemical compound C=1C(C2CCCC2)=NNC=1NC(=O)NCCC1=CC=CC=C1 LPAQWHHDOXAKNP-UHFFFAOYSA-N 0.000 claims description 3
- MYZDJDBHEWGEKD-UHFFFAOYSA-N 1-(5-cyclopentyl-1h-pyrazol-3-yl)-3-(4-hydroxybutyl)urea Chemical compound N1C(NC(=O)NCCCCO)=CC(C2CCCC2)=N1 MYZDJDBHEWGEKD-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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Applications Claiming Priority (2)
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| US09/372,833 US6387900B1 (en) | 1999-08-12 | 1999-08-12 | 3(5)-ureido-pyrazole derivatives process for their preparation and their use as antitumor agents |
| PCT/US2000/017878 WO2001012188A1 (en) | 1999-08-12 | 2000-08-11 | 3(5)-ureido-pyrazole derivatives, process for their preparation and their use as antitumor agents |
Publications (1)
| Publication Number | Publication Date |
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| HUP0301857A2 true HUP0301857A2 (hu) | 2003-09-29 |
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| HU0301857A HUP0301857A2 (hu) | 1999-08-12 | 2000-08-11 | 3(5)-Ureido-pirazol-származékok, eljárás elżállításukra alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények |
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| RU2664541C2 (ru) | 2012-11-13 | 2018-08-20 | Эррэй Биофарма Инк. | Бициклические соединения мочевины, тиомочевины, гуанидина и цианогуанидина, пригодные для лечения боли |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3646059A (en) * | 1969-05-05 | 1972-02-29 | Du Pont | Plant growth regulatory ureidopyrazoles |
| US3754887A (en) * | 1969-05-05 | 1973-08-28 | Du Pont | Ureidopyrazoles defoliants |
| WO1996014843A2 (en) | 1994-11-10 | 1996-05-23 | Cor Therapeutics, Inc. | Pharmaceutical pyrazole compositions useful as inhibitors of protein kinases |
| AU5135998A (en) * | 1996-12-03 | 1998-06-29 | Banyu Pharmaceutical Co., Ltd. | Novel urea derivatives |
| CA2288787A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | Pyrazole derivatives as p38 kinase inhibitors |
| EP1041982B1 (en) | 1997-12-22 | 2011-10-19 | Bayer HealthCare LLC | INHIBITION OF p38 KINASE ACTIVITY USING SUBSTITUTED HETEROCYCLIC UREAS |
-
1999
- 1999-08-12 US US09/372,833 patent/US6387900B1/en not_active Expired - Fee Related
-
2000
- 2000-08-03 PE PE2000000771A patent/PE20010482A1/es not_active Application Discontinuation
- 2000-08-10 AR ARP000104118A patent/AR035557A1/es unknown
- 2000-08-10 CO CO00059913A patent/CO5200848A1/es not_active Application Discontinuation
- 2000-08-11 CA CA002380786A patent/CA2380786A1/en not_active Abandoned
- 2000-08-11 SK SK208-2002A patent/SK2082002A3/sk unknown
- 2000-08-11 AU AU67470/00A patent/AU6747000A/en not_active Abandoned
- 2000-08-11 ES ES00955241T patent/ES2284518T3/es not_active Expired - Lifetime
- 2000-08-11 PL PL00354058A patent/PL354058A1/xx not_active Application Discontinuation
- 2000-08-11 EA EA200200249A patent/EA200200249A1/ru unknown
- 2000-08-11 JP JP2001516534A patent/JP2003507328A/ja not_active Withdrawn
- 2000-08-11 MX MXPA02001497A patent/MXPA02001497A/es active IP Right Grant
- 2000-08-11 HK HK03101874.6A patent/HK1049790A1/zh unknown
- 2000-08-11 CN CN00812736A patent/CN1379668A/zh active Pending
- 2000-08-11 IL IL14792500A patent/IL147925A0/xx unknown
- 2000-08-11 HU HU0301857A patent/HUP0301857A2/hu unknown
- 2000-08-11 DE DE60034683T patent/DE60034683T2/de not_active Expired - Fee Related
- 2000-08-11 AT AT00955241T patent/ATE361070T1/de not_active IP Right Cessation
- 2000-08-11 WO PCT/US2000/017878 patent/WO2001012188A1/en not_active Ceased
- 2000-08-11 EP EP00955241A patent/EP1202734B1/en not_active Expired - Lifetime
- 2000-08-11 BR BR0013277-2A patent/BR0013277A/pt not_active Application Discontinuation
- 2000-08-11 NZ NZ517238A patent/NZ517238A/en unknown
- 2000-08-11 KR KR1020027001815A patent/KR20020060158A/ko not_active Withdrawn
-
2002
- 2002-02-08 ZA ZA200201118A patent/ZA200201118B/en unknown
- 2002-02-11 NO NO20020687A patent/NO20020687L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ517238A (en) | 2004-01-30 |
| NO20020687D0 (no) | 2002-02-11 |
| NO20020687L (no) | 2002-04-03 |
| AU6747000A (en) | 2001-03-13 |
| PL354058A1 (en) | 2003-12-15 |
| US6387900B1 (en) | 2002-05-14 |
| EP1202734B1 (en) | 2007-05-02 |
| CA2380786A1 (en) | 2001-02-22 |
| ATE361070T1 (de) | 2007-05-15 |
| BR0013277A (pt) | 2002-06-18 |
| ZA200201118B (en) | 2003-05-28 |
| EP1202734A1 (en) | 2002-05-08 |
| KR20020060158A (ko) | 2002-07-16 |
| DE60034683D1 (de) | 2007-06-14 |
| EA200200249A1 (ru) | 2002-08-29 |
| AR035557A1 (es) | 2004-06-16 |
| PE20010482A1 (es) | 2001-04-20 |
| JP2003507328A (ja) | 2003-02-25 |
| IL147925A0 (en) | 2002-08-14 |
| EP1202734A4 (en) | 2004-09-01 |
| WO2001012188A1 (en) | 2001-02-22 |
| ES2284518T3 (es) | 2007-11-16 |
| HK1049790A1 (zh) | 2003-05-30 |
| CN1379668A (zh) | 2002-11-13 |
| SK2082002A3 (en) | 2002-09-10 |
| CO5200848A1 (es) | 2002-09-27 |
| MXPA02001497A (es) | 2003-07-21 |
| DE60034683T2 (de) | 2008-01-17 |
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