ZA200508694B - Novel aniline derivatives, their manufacture and use as pharmaceutical agents - Google Patents
Novel aniline derivatives, their manufacture and use as pharmaceutical agents Download PDFInfo
- Publication number
- ZA200508694B ZA200508694B ZA200508694A ZA200508694A ZA200508694B ZA 200508694 B ZA200508694 B ZA 200508694B ZA 200508694 A ZA200508694 A ZA 200508694A ZA 200508694 A ZA200508694 A ZA 200508694A ZA 200508694 B ZA200508694 B ZA 200508694B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- triazol
- vinyl
- butyl
- oxazol
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000008177 pharmaceutical agent Substances 0.000 title description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 229920002554 vinyl polymer Polymers 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 13
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- -1 Triazol-1-yl-butyl Chemical group 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- QOFYIBPWKHJYKM-UHFFFAOYSA-N 2-[2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC(C=CC=2C=CC(=CC=2)C(F)(F)F)=N1 QOFYIBPWKHJYKM-UHFFFAOYSA-N 0.000 claims description 3
- DVCGDSUWERYQQO-UHFFFAOYSA-N 4-[4-(triazol-1-yl)butyl]aniline Chemical compound C1=CC(N)=CC=C1CCCCN1N=NC=C1 DVCGDSUWERYQQO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- FAEWDWHRJPNTNG-MDWZMJQESA-N 2-[(e)-2-[4-(difluoromethoxy)phenyl]ethenyl]-n-[4-[4-(triazol-1-yl)butyl]phenyl]-1,3-oxazole-4-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1\C=C\C1=NC(C(=O)NC=2C=CC(CCCCN3N=NC=C3)=CC=2)=CO1 FAEWDWHRJPNTNG-MDWZMJQESA-N 0.000 claims description 2
- PFVDENNGUGBIMV-UHFFFAOYSA-N 4-[2-(triazol-1-yl)ethoxymethyl]-n-[[2-[2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C1=CC(C(F)(F)F)=CC=C1C=CC1=NC(CNC=2C=CC(COCCN3N=NC=C3)=CC=2)=CO1 PFVDENNGUGBIMV-UHFFFAOYSA-N 0.000 claims description 2
- QPKQROWGZGXUMY-UHFFFAOYSA-N 4-[4-(triazol-1-yl)but-1-enyl]-n-[[2-[2-[4-(trifluoromethylsulfinyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C1=CC(S(=O)C(F)(F)F)=CC=C1C=CC1=NC(CNC=2C=CC(C=CCCN3N=NC=C3)=CC=2)=CO1 QPKQROWGZGXUMY-UHFFFAOYSA-N 0.000 claims description 2
- UEKGQKJMHPILPJ-UHFFFAOYSA-N 4-[4-(triazol-1-yl)butyl]-n-[[2-[2-[4-(trifluoromethoxy)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C1=CC(OC(F)(F)F)=CC=C1C=CC1=NC(CNC=2C=CC(CCCCN3N=NC=C3)=CC=2)=CO1 UEKGQKJMHPILPJ-UHFFFAOYSA-N 0.000 claims description 2
- ZRXJLZVVKJKESI-UHFFFAOYSA-N 4-[4-(triazol-1-yl)butyl]-n-[[2-[2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C1=CC(C(F)(F)F)=CC=C1C=CC1=NC(CNC=2C=CC(CCCCN3N=NC=C3)=CC=2)=CO1 ZRXJLZVVKJKESI-UHFFFAOYSA-N 0.000 claims description 2
- AAQITVPLUXNIIU-UHFFFAOYSA-N C1=CC(NC)=CC=C1CCCCN1N=NC=C1 Chemical compound C1=CC(NC)=CC=C1CCCCN1N=NC=C1 AAQITVPLUXNIIU-UHFFFAOYSA-N 0.000 claims description 2
- OYGJBWMHFQDNCF-UHFFFAOYSA-N n-[4-[4-(triazol-1-yl)butyl]phenyl]-2-[2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole-4-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C=CC1=NC(C(=O)NC=2C=CC(CCCCN3N=NC=C3)=CC=2)=CO1 OYGJBWMHFQDNCF-UHFFFAOYSA-N 0.000 claims description 2
- KUXHYRMXCMFBCX-UHFFFAOYSA-N n-methyl-4-[4-(triazol-1-yl)butyl]-n-[[2-[2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C=1C=C(CCCCN2N=NC=C2)C=CC=1N(C)CC(N=1)=COC=1C=CC1=CC=C(C(F)(F)F)C=C1 KUXHYRMXCMFBCX-UHFFFAOYSA-N 0.000 claims description 2
- YYJWCGMWJFIZCI-UHFFFAOYSA-N n-methyl-n-[4-[4-(triazol-1-yl)butyl]phenyl]-2-[2-[4-(trifluoromethoxy)phenyl]ethenyl]-1,3-oxazole-4-carboxamide Chemical compound C=1C=C(CCCCN2N=NC=C2)C=CC=1N(C)C(=O)C(N=1)=COC=1C=CC1=CC=C(OC(F)(F)F)C=C1 YYJWCGMWJFIZCI-UHFFFAOYSA-N 0.000 claims description 2
- 230000004614 tumor growth Effects 0.000 claims 3
- ISGUXUQYOSRDBK-DUXPYHPUSA-N 2-[(e)-2-(2,2-difluoro-1,3-benzodioxol-5-yl)ethenyl]-1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC(\C=C\C=2C=C3OC(F)(F)OC3=CC=2)=N1 ISGUXUQYOSRDBK-DUXPYHPUSA-N 0.000 claims 1
- VKVBJXXFTHKHLN-UHFFFAOYSA-N 4-[3-(triazol-1-yl)propoxy]-n-[[2-[2-[4-(trifluoromethoxy)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C1=CC(OC(F)(F)F)=CC=C1C=CC1=NC(CNC=2C=CC(OCCCN3N=NC=C3)=CC=2)=CO1 VKVBJXXFTHKHLN-UHFFFAOYSA-N 0.000 claims 1
- UIWPPKGGLFSXOL-UHFFFAOYSA-N 4-[3-(triazol-1-yl)propoxy]-n-[[2-[2-[4-(trifluoromethylsulfanyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C1=CC(SC(F)(F)F)=CC=C1C=CC1=NC(CNC=2C=CC(OCCCN3N=NC=C3)=CC=2)=CO1 UIWPPKGGLFSXOL-UHFFFAOYSA-N 0.000 claims 1
- PARIVUGDFNLQEG-MDWZMJQESA-N 4-[4-(triazol-1-yl)butyl]-n-[[2-[(e)-2-[4-(trifluoromethylsulfinyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C1=CC(S(=O)C(F)(F)F)=CC=C1\C=C\C1=NC(CNC=2C=CC(CCCCN3N=NC=C3)=CC=2)=CO1 PARIVUGDFNLQEG-MDWZMJQESA-N 0.000 claims 1
- UXJRGILGFHFRHH-UHFFFAOYSA-N n-[[2-[2-(4-chlorophenyl)ethenyl]-1,3-oxazol-4-yl]methyl]-4-[3-(triazol-1-yl)propoxy]aniline Chemical compound C1=CC(Cl)=CC=C1C=CC1=NC(CNC=2C=CC(OCCCN3N=NC=C3)=CC=2)=CO1 UXJRGILGFHFRHH-UHFFFAOYSA-N 0.000 claims 1
- LVUTXEGQSNUGJA-UHFFFAOYSA-N n-methyl-4-[4-(triazol-1-yl)butyl]-n-[[2-[2-[4-(trifluoromethylsulfanyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methyl]aniline Chemical compound C=1C=C(CCCCN2N=NC=C2)C=CC=1N(C)CC(N=1)=COC=1C=CC1=CC=C(SC(F)(F)F)C=C1 LVUTXEGQSNUGJA-UHFFFAOYSA-N 0.000 claims 1
- NOBVJMBHDBIRDG-UHFFFAOYSA-N n-methyl-n-[4-[3-(triazol-1-yl)propoxy]phenyl]-2-[2-[4-(trifluoromethoxy)phenyl]ethenyl]-1,3-oxazole-4-carboxamide Chemical compound C=1C=C(OCCCN2N=NC=C2)C=CC=1N(C)C(=O)C(N=1)=COC=1C=CC1=CC=C(OC(F)(F)F)C=C1 NOBVJMBHDBIRDG-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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- 210000004027 cell Anatomy 0.000 description 11
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001448 anilines Chemical class 0.000 description 8
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- 239000000969 carrier Substances 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
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Classifications
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- 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
- C07D413/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03009908 | 2003-04-30 |
Publications (1)
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|---|---|
| ZA200508694B true ZA200508694B (en) | 2007-06-27 |
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|---|---|---|---|
| ZA200508694A ZA200508694B (en) | 2003-04-30 | 2005-10-26 | Novel aniline derivatives, their manufacture and use as pharmaceutical agents |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7205326B2 (zh) |
| EP (1) | EP1622896B1 (zh) |
| JP (1) | JP2006515347A (zh) |
| KR (1) | KR100763293B1 (zh) |
| CN (1) | CN100345845C (zh) |
| AR (1) | AR044098A1 (zh) |
| AT (1) | ATE366252T1 (zh) |
| AU (1) | AU2004234060A1 (zh) |
| BR (1) | BRPI0409951A (zh) |
| CA (1) | CA2522809A1 (zh) |
| CL (1) | CL2004000898A1 (zh) |
| CO (1) | CO5640050A2 (zh) |
| DE (1) | DE602004007374T2 (zh) |
| ES (1) | ES2290701T3 (zh) |
| MX (1) | MXPA05011671A (zh) |
| NO (1) | NO20054495L (zh) |
| RU (1) | RU2005137033A (zh) |
| TW (1) | TW200423931A (zh) |
| WO (1) | WO2004096796A1 (zh) |
| ZA (1) | ZA200508694B (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200612914A (en) * | 2004-03-05 | 2006-05-01 | Hoffmann La Roche | Novel oxidized thioether derivatives, their manufacture and use as pharmaceutical agents |
| FR2876692B1 (fr) | 2004-10-19 | 2007-02-23 | Sanofi Aventis Sa | Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique |
| US20060116407A1 (en) * | 2004-11-22 | 2006-06-01 | Birgit Bossenmaier | Amide derivatives |
| JP2009504586A (ja) * | 2005-08-08 | 2009-02-05 | エフ．ホフマン−ラ ロシュ アーゲー | ピラゾール誘導体、それらの製造及び医薬品としての使用 |
| CN112920133B (zh) * | 2021-01-29 | 2022-09-16 | 中国医科大学 | (e)-4-甲基-2-(4-(三氟甲基)苯乙烯基)噁唑类化合物及其制备方法与用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6211215B1 (en) * | 1996-07-19 | 2001-04-03 | Takeda Chemical Industries, Ltd. | Heterocyclic compounds, their production and use |
| PE20011178A1 (es) * | 2000-04-07 | 2001-11-19 | Takeda Chemical Industries Ltd | Compuestos heterociclicos y su produccion |
-
2004
- 2004-04-26 AR ARP040101415A patent/AR044098A1/es unknown
- 2004-04-26 TW TW093111557A patent/TW200423931A/zh unknown
- 2004-04-28 CL CL200400898A patent/CL2004000898A1/es unknown
- 2004-04-28 US US10/833,721 patent/US7205326B2/en not_active Expired - Fee Related
- 2004-04-29 KR KR1020057020486A patent/KR100763293B1/ko not_active IP Right Cessation
- 2004-04-29 ES ES04730211T patent/ES2290701T3/es not_active Expired - Lifetime
- 2004-04-29 EP EP04730211A patent/EP1622896B1/en not_active Expired - Lifetime
- 2004-04-29 RU RU2005137033/04A patent/RU2005137033A/ru not_active Application Discontinuation
- 2004-04-29 CN CNB2004800116553A patent/CN100345845C/zh not_active Expired - Fee Related
- 2004-04-29 MX MXPA05011671A patent/MXPA05011671A/es active IP Right Grant
- 2004-04-29 CA CA002522809A patent/CA2522809A1/en not_active Abandoned
- 2004-04-29 JP JP2006500101A patent/JP2006515347A/ja active Pending
- 2004-04-29 AU AU2004234060A patent/AU2004234060A1/en not_active Abandoned
- 2004-04-29 DE DE602004007374T patent/DE602004007374T2/de not_active Expired - Fee Related
- 2004-04-29 AT AT04730211T patent/ATE366252T1/de not_active IP Right Cessation
- 2004-04-29 WO PCT/EP2004/004520 patent/WO2004096796A1/en active IP Right Grant
- 2004-04-29 BR BRPI0409951-6A patent/BRPI0409951A/pt not_active IP Right Cessation
-
2005
- 2005-09-28 NO NO20054495A patent/NO20054495L/no not_active Application Discontinuation
- 2005-10-26 ZA ZA200508694A patent/ZA200508694B/en unknown
- 2005-10-26 CO CO05109227A patent/CO5640050A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060006070A (ko) | 2006-01-18 |
| BRPI0409951A (pt) | 2006-04-25 |
| US20040254217A1 (en) | 2004-12-16 |
| DE602004007374D1 (de) | 2007-08-16 |
| WO2004096796A1 (en) | 2004-11-11 |
| CN100345845C (zh) | 2007-10-31 |
| NO20054495L (no) | 2005-11-23 |
| CL2004000898A1 (es) | 2005-03-04 |
| TW200423931A (en) | 2004-11-16 |
| US7205326B2 (en) | 2007-04-17 |
| JP2006515347A (ja) | 2006-05-25 |
| ES2290701T3 (es) | 2008-02-16 |
| AR044098A1 (es) | 2005-08-24 |
| EP1622896B1 (en) | 2007-07-04 |
| AU2004234060A1 (en) | 2004-11-11 |
| CA2522809A1 (en) | 2004-11-11 |
| ATE366252T1 (de) | 2007-07-15 |
| CO5640050A2 (es) | 2006-05-31 |
| NO20054495D0 (no) | 2005-09-28 |
| EP1622896A1 (en) | 2006-02-08 |
| MXPA05011671A (es) | 2005-12-15 |
| DE602004007374T2 (de) | 2008-03-20 |
| CN1780830A (zh) | 2006-05-31 |
| KR100763293B1 (ko) | 2007-10-04 |
| RU2005137033A (ru) | 2006-06-27 |
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