RU2007121850A - Производные фосфонооксихиназолина и их фармацевтическое применение - Google Patents
Производные фосфонооксихиназолина и их фармацевтическое применение Download PDFInfo
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- RU2007121850A RU2007121850A RU2007121850/04K RU2007121850K RU2007121850A RU 2007121850 A RU2007121850 A RU 2007121850A RU 2007121850/04 K RU2007121850/04 K RU 2007121850/04K RU 2007121850 K RU2007121850 K RU 2007121850K RU 2007121850 A RU2007121850 A RU 2007121850A
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- amino
- acetamide
- pyrazol
- quinazolin
- propoxy
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- -1 2,3-difluorophenyl Chemical group 0.000 claims abstract 13
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims abstract 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- WWZCTHYYRVAJIG-NRFANRHFSA-N n-(3-fluorophenyl)-2-[3-[[7-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound OC[C@@H]1CCCN1CCCOC1=CC=C(C(NC2=NNC(CC(=O)NC=3C=C(F)C=CC=3)=C2)=NC=N2)C2=C1 WWZCTHYYRVAJIG-NRFANRHFSA-N 0.000 claims abstract 4
- XQWUFPUUHVVAIM-UHFFFAOYSA-N n-(3-fluorophenyl)-2-[3-[[7-[3-[2-hydroxyethyl(propyl)amino]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound N=1C=NC2=CC(OCCCN(CCO)CCC)=CC=C2C=1NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1 XQWUFPUUHVVAIM-UHFFFAOYSA-N 0.000 claims abstract 3
- ZGBRLIPLHRQLPB-IBGZPJMESA-N n-(2,3-difluorophenyl)-2-[3-[[7-[3-[(2s)-2-(2-hydroxyethyl)pyrrolidin-1-yl]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound OCC[C@@H]1CCCN1CCCOC1=CC=C(C(NC2=NNC(CC(=O)NC=3C(=C(F)C=CC=3)F)=C2)=NC=N2)C2=C1 ZGBRLIPLHRQLPB-IBGZPJMESA-N 0.000 claims abstract 2
- ZNGNLXZBVWXEKM-SFHVURJKSA-N n-(2,3-difluorophenyl)-2-[3-[[7-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound OC[C@@H]1CCCN1CCCOC1=CC=C(C(NC2=NNC(CC(=O)NC=3C(=C(F)C=CC=3)F)=C2)=NC=N2)C2=C1 ZNGNLXZBVWXEKM-SFHVURJKSA-N 0.000 claims abstract 2
- WWZCTHYYRVAJIG-OAQYLSRUSA-N n-(3-fluorophenyl)-2-[3-[[7-[3-[(2r)-2-(hydroxymethyl)pyrrolidin-1-yl]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound OC[C@H]1CCCN1CCCOC1=CC=C(C(NC2=NNC(CC(=O)NC=3C=C(F)C=CC=3)=C2)=NC=N2)C2=C1 WWZCTHYYRVAJIG-OAQYLSRUSA-N 0.000 claims abstract 2
- 239000010802 sludge Substances 0.000 claims 3
- IBBRPNCDYSSTKO-UHFFFAOYSA-N 2-[3-[[7-[3-[ethyl(2-hydroxyethyl)amino]propoxy]-6-fluoroquinazolin-4-yl]amino]-1h-pyrazol-5-yl]-n-(3-fluorophenyl)acetamide Chemical compound C=12C=C(F)C(OCCCN(CCO)CC)=CC2=NC=NC=1NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1 IBBRPNCDYSSTKO-UHFFFAOYSA-N 0.000 claims 2
- UHVRUAQUBZYULG-UHFFFAOYSA-N 2-[3-[[7-[3-[ethyl(3-hydroxypropyl)amino]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]-n-(3-fluorophenyl)acetamide Chemical compound N=1C=NC2=CC(OCCCN(CCCO)CC)=CC=C2C=1NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1 UHVRUAQUBZYULG-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- QAXMKRUYFZMQME-UHFFFAOYSA-N 2-[3-[[7-[3-[butyl(2-hydroxyethyl)amino]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]-n-(2,3-difluorophenyl)acetamide Chemical compound N=1C=NC2=CC(OCCCN(CCO)CCCC)=CC=C2C=1NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1F QAXMKRUYFZMQME-UHFFFAOYSA-N 0.000 claims 1
- ZZQPWSQANDNNMJ-UHFFFAOYSA-N 2-[3-[[7-[3-[cyclopentyl(2-hydroxyethyl)amino]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]-n-(2,3-difluorophenyl)acetamide Chemical compound C1CCCC1N(CCO)CCCOC(C=C1N=CN=2)=CC=C1C=2NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1F ZZQPWSQANDNNMJ-UHFFFAOYSA-N 0.000 claims 1
- PIJGHCNBBRXNDH-UHFFFAOYSA-N 2-[3-[[7-[3-[cyclopentyl(2-hydroxyethyl)amino]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]-n-(3-fluorophenyl)acetamide Chemical compound C1CCCC1N(CCO)CCCOC(C=C1N=CN=2)=CC=C1C=2NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1 PIJGHCNBBRXNDH-UHFFFAOYSA-N 0.000 claims 1
- FJSLAMFWWZCIJT-LJQANCHMSA-N n-(2,3-difluorophenyl)-2-[3-[[7-[4-[(2r)-2-(hydroxymethyl)pyrrolidin-1-yl]butoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound OC[C@H]1CCCN1CCCCOC1=CC=C(C(NC2=NNC(CC(=O)NC=3C(=C(F)C=CC=3)F)=C2)=NC=N2)C2=C1 FJSLAMFWWZCIJT-LJQANCHMSA-N 0.000 claims 1
- FJSLAMFWWZCIJT-IBGZPJMESA-N n-(2,3-difluorophenyl)-2-[3-[[7-[4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]butoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound OC[C@@H]1CCCN1CCCCOC1=CC=C(C(NC2=NNC(CC(=O)NC=3C(=C(F)C=CC=3)F)=C2)=NC=N2)C2=C1 FJSLAMFWWZCIJT-IBGZPJMESA-N 0.000 claims 1
- CJXGFQJYVYILDY-UHFFFAOYSA-N n-(2,3-difluorophenyl)-2-[3-[[7-[[1-(2-hydroxyethyl)piperidin-4-yl]methoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound C1CN(CCO)CCC1COC1=CC=C(C(NC2=NNC(CC(=O)NC=3C(=C(F)C=CC=3)F)=C2)=NC=N2)C2=C1 CJXGFQJYVYILDY-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- NPIAVEXGKZDDRP-UHFFFAOYSA-N n-(2,3-difluorophenyl)-2-[3-[[7-[3-[(4-hydroxy-2-methylbutan-2-yl)amino]propoxy]quinazolin-4-yl]amino]-1h-pyrazol-5-yl]acetamide Chemical compound N=1C=NC2=CC(OCCCNC(C)(CCO)C)=CC=C2C=1NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1F NPIAVEXGKZDDRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 abstract 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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Abstract
1.Соединение, выбранное из любого следующего соединения:N-(2,3-дифторфенил)-2-{3-[(7-{[1-(2-гидроксиэтил)пиперидин-4-ил]метокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(2,3-дифторфенил)-2-{3-[(7-{3-[(3-гидрокси-1,1-диметилпропил)амино]пропокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(2,3-дифторфенил)-2-{3-[(7-{3-[(2S)-2-(2-гидроксиэтил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(2,3-дифторфенил)-2-{3-[(7-{3-[(2-гидроксиэтил)(бутил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;2-{3-[(7-{3-[циклопентил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-(2,3-дифторфенил)ацетамида;N-(2,3-дифторфенил)-2-{3-[(7-{3-[(2S)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(3-фторфенил)-2-{3-[(7-{3-[(2S)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;2-{3-[(7-{3-[циклопентил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-фторфенил)ацетамида;N-(3-фторфенил)-2-{3-[(7-{3-[этил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(3-фторфенил)-2-{3-[(7-{3-[(2-гидрокси-1,1-диметилэтил)амино]пропокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(3-фторфенил)-2-{3-[(7-{3-[(2-гидроксиэтил)(пропил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(3-фторфенил)-2-{3-[(7-{3-[(2R)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(2,3-дифторфенил)-2-{3-[(7-{4-[(2-гидроксиэтил)(пропил)амино]бутокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(3-фторфенил)-2-{3-[(7-{4-[этил(2-гидроксиэтил)амино]бутокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;N-(2,3-дифторфенил)-2-{3-[(7-{4-[(2R)-2-(гидроксиметил)пирролидин-1-ил]бутокси}-хиназо�
Claims (3)
1.Соединение, выбранное из любого следующего соединения:
N-(2,3-дифторфенил)-2-{3-[(7-{[1-(2-гидроксиэтил)пиперидин-4-ил]метокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{3-[(3-гидрокси-1,1-диметилпропил)амино]пропокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{3-[(2S)-2-(2-гидроксиэтил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{3-[(2-гидроксиэтил)(бутил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
2-{3-[(7-{3-[циклопентил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-(2,3-дифторфенил)ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{3-[(2S)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2S)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
2-{3-[(7-{3-[циклопентил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-фторфенил)ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[этил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2-гидрокси-1,1-диметилэтил)амино]пропокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2-гидроксиэтил)(пропил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2R)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{4-[(2-гидроксиэтил)(пропил)амино]бутокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{4-[этил(2-гидроксиэтил)амино]бутокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{4-[(2R)-2-(гидроксиметил)пирролидин-1-ил]бутокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{4-[(2-гидроксиэтил)(метил)амино]бутокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(2,3-дифторфенил)-2-{3-[(7-{4-[(2S)-2-(гидроксиметил)пирролидин-1-ил]бутокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
2-{3-[(7-{3-[этил(3-гидроксипропил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-(3-фторфенил)ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2-гидроксиэтил)(2-метоксиэтил)амино]пропокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида; и
2-{3-[(7-{3-[этил(2-гидроксиэтил)амино]пропокси}-6-фторхиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-(3-фторфенил)ацетамида;
или его фармацевтически приемлемая соль.
2. Соединение, выбранное из любого следующего соединения:
N-(3-фторфенил)-2-{3-[(7-{3-[(2S)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
2-{3-[(7-{3-[циклопентил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-(3-фторфенил)ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[этил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1Н-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2-гидрокси-1,1-диметилэтил)амино]пропокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2-гидроксиэтил)(пропил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{3-[(2S)-2-(гидроксиметил)пирролидин-1-ил]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
N-(3-фторфенил)-2-{3-[(7-{4-[этил(2-гидроксиэтил)амино]бутокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида;
2-{3-[(7-{3-[этил(3-гидроксипропил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-(3-фторфенил)ацетамида;
N-{3-фторфенил)-2-{3-[(7-{3-[(2-гидроксиэтил)(2-метоксиэтил)амино]пропокси}хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамида; и
2-{3-[(7-{3-[этил(2-гидроксиэтил)амино]пропокси}-6-фторхиназолин-4-ил)амино]-1H-пиразол-5-ил}-N-(3-фторфенил)ацетамида;
или его фармацевтически приемлемая соль.
3. N-(3-фторфенил)-2-{3-[(7-{3-[этил(2-гидроксиэтил)амино]пропокси}-хиназолин-4-ил)амино]-1H-пиразол-5-ил}ацетамид.
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| EP02293238 | 2002-12-24 | ||
| EP02293238.8 | 2002-12-24 | ||
| EP03291315.4 | 2003-06-02 | ||
| EP03291315 | 2003-06-02 |
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| RU2005123485/04A RU2357971C2 (ru) | 2002-12-24 | 2003-12-22 | Производные фосфонооксихиназолина и их фармацевтическое применение |
| RU2007121850/04K RU2007121850A (ru) | 2002-12-24 | 2007-06-13 | Производные фосфонооксихиназолина и их фармацевтическое применение |
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| RU2005123485/04A RU2357971C2 (ru) | 2002-12-24 | 2003-12-22 | Производные фосфонооксихиназолина и их фармацевтическое применение |
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