NO332188B1 - Aminoheteroarylforbindelser samt anvendelse av slike for fremstilling av preparat for behandling av sykdom. - Google Patents
Aminoheteroarylforbindelser samt anvendelse av slike for fremstilling av preparat for behandling av sykdom. Download PDFInfo
- Publication number
- NO332188B1 NO332188B1 NO20054080A NO20054080A NO332188B1 NO 332188 B1 NO332188 B1 NO 332188B1 NO 20054080 A NO20054080 A NO 20054080A NO 20054080 A NO20054080 A NO 20054080A NO 332188 B1 NO332188 B1 NO 332188B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- pyridin
- ethoxy
- amino
- dichloro
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 59
- 201000010099 disease Diseases 0.000 title description 21
- 125000005214 aminoheteroaryl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 225
- 239000000203 mixture Substances 0.000 claims abstract description 160
- 239000003112 inhibitor Substances 0.000 claims abstract description 16
- -1 (3-{6-amino-6-[1-(2,6-dichloro-phenyl)-ethoxy]-pyridin-3-yl}-phenyl)-((R)-2-pyrrolidin-1-ylmethyl-pyrrolidine -1-yl)-methanone Chemical compound 0.000 claims description 81
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 76
- 206010028980 Neoplasm Diseases 0.000 claims description 67
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- 150000003839 salts Chemical class 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 21
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 17
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 230000002159 abnormal effect Effects 0.000 claims description 12
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- 150000002367 halogens Chemical class 0.000 claims description 12
- 230000010261 cell growth Effects 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
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- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
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- AUCWHTWWTRFLTK-UHFFFAOYSA-N [4-[6-amino-5-[1-[2-fluoro-6-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound FC=1C=CC=C(C(F)(F)F)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 AUCWHTWWTRFLTK-UHFFFAOYSA-N 0.000 claims description 4
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- NVJXHLYVXPKGOY-UHFFFAOYSA-N 4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)NCCN1CCCC1 NVJXHLYVXPKGOY-UHFFFAOYSA-N 0.000 claims description 3
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- LPWNBBNZNCSNBM-UHFFFAOYSA-N [3-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)N(CC1)CCC1N1CCCC1 LPWNBBNZNCSNBM-UHFFFAOYSA-N 0.000 claims description 2
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- QWSDYGXUBMHYCQ-UHFFFAOYSA-N [4-[6-amino-5-[(2,4,6-trifluorophenyl)methoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)C=C1OCC1=C(F)C=C(F)C=C1F QWSDYGXUBMHYCQ-UHFFFAOYSA-N 0.000 claims description 2
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- AEHVEIFJNDIFGT-CALCHBBNSA-N [4-[6-amino-5-[(3-fluoro-2-methoxyphenyl)methoxy]pyridin-3-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound COC1=C(F)C=CC=C1COC1=CC(C=2C=CC(=CC=2)C(=O)N2C[C@@H](C)N[C@@H](C)C2)=CN=C1N AEHVEIFJNDIFGT-CALCHBBNSA-N 0.000 claims description 2
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- KKZCMUIQONHMRX-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-3-fluorophenyl]-(2,2-dimethylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C(=C1)F)=CC=C1C(=O)N1CCNCC1(C)C KKZCMUIQONHMRX-UHFFFAOYSA-N 0.000 claims description 2
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- RYNWHMVYHXUHGE-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(C=2C=C(OC(C)C=3C(=C(F)C=CC=3Cl)Cl)C(N)=NC=2)C=C1 RYNWHMVYHXUHGE-UHFFFAOYSA-N 0.000 claims description 2
- GCHXQZRZNXAOKV-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methyl-1,4-diazepan-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CCCN(C)CC1 GCHXQZRZNXAOKV-UHFFFAOYSA-N 0.000 claims description 2
- GCHURKJETQITJF-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 GCHURKJETQITJF-UHFFFAOYSA-N 0.000 claims description 2
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- APZWJXYBVLSYAK-LRHAYUFXSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r)-3-aminopyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@@H](N)C1 APZWJXYBVLSYAK-LRHAYUFXSA-N 0.000 claims description 2
- AWXKDRXUIGCEML-LRHAYUFXSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@@H](O)C1 AWXKDRXUIGCEML-LRHAYUFXSA-N 0.000 claims description 2
- FGXJPXSISSLIIV-DGXGNLECSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r,4s)-3,4-dihydroxypyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1C[C@H](O)[C@H](O)C1 FGXJPXSISSLIIV-DGXGNLECSA-N 0.000 claims description 2
- APZWJXYBVLSYAK-RUINGEJQSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3s)-3-aminopyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@H](N)C1 APZWJXYBVLSYAK-RUINGEJQSA-N 0.000 claims description 2
- AWXKDRXUIGCEML-RUINGEJQSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3s)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@H](O)C1 AWXKDRXUIGCEML-RUINGEJQSA-N 0.000 claims description 2
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- OWJYVAGQUFLWBE-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 OWJYVAGQUFLWBE-UHFFFAOYSA-N 0.000 claims description 2
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- VZYQNRXUIIMQEQ-XPKAQORNSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r)-3-aminopyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@@H](N)C1 VZYQNRXUIIMQEQ-XPKAQORNSA-N 0.000 claims description 2
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- VZYQNRXUIIMQEQ-IBYPIGCZSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3s)-3-aminopyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@H](N)C1 VZYQNRXUIIMQEQ-IBYPIGCZSA-N 0.000 claims description 2
- WSANBMQPGMLNPV-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)propoxy]pyridin-3-yl]phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(CC)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC(C)NC(C)C1 WSANBMQPGMLNPV-UHFFFAOYSA-N 0.000 claims description 2
- GDNMBLFQCIKWSG-UHFFFAOYSA-N [4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(C=2C=C(OC(C)C=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)C=C1 GDNMBLFQCIKWSG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US44958803P | 2003-02-26 | 2003-02-26 | |
US54022904P | 2004-01-29 | 2004-01-29 | |
PCT/US2004/005495 WO2004076412A2 (en) | 2003-02-26 | 2004-02-26 | Aminoheteroaryl compounds as protein kinase inhibitors |
Publications (3)
Publication Number | Publication Date |
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NO20054080D0 NO20054080D0 (no) | 2005-09-01 |
NO20054080L NO20054080L (no) | 2005-11-21 |
NO332188B1 true NO332188B1 (no) | 2012-07-23 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20054080A NO332188B1 (no) | 2003-02-26 | 2005-09-01 | Aminoheteroarylforbindelser samt anvendelse av slike for fremstilling av preparat for behandling av sykdom. |
Country Status (29)
Country | Link |
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US (2) | US7230098B2 (ja) |
EP (2) | EP1603570B9 (ja) |
JP (1) | JP4695588B2 (ja) |
KR (1) | KR101106905B1 (ja) |
CN (1) | CN103265477B (ja) |
AP (1) | AP2114A (ja) |
AU (1) | AU2004215428B2 (ja) |
BR (1) | BRPI0407827B8 (ja) |
CA (1) | CA2517256C (ja) |
CY (2) | CY1113837T1 (ja) |
DK (2) | DK2476667T3 (ja) |
EA (1) | EA010727B1 (ja) |
EC (1) | ECSP055988A (ja) |
ES (2) | ES2502490T3 (ja) |
GE (1) | GEP20084341B (ja) |
HR (1) | HRP20050714B1 (ja) |
IL (1) | IL170291A (ja) |
IS (1) | IS2910B (ja) |
MA (1) | MA27713A1 (ja) |
ME (1) | MEP52808A (ja) |
MX (1) | MXPA05009063A (ja) |
NO (1) | NO332188B1 (ja) |
NZ (1) | NZ541861A (ja) |
OA (1) | OA13151A (ja) |
PL (1) | PL216368B1 (ja) |
PT (2) | PT1603570E (ja) |
RS (1) | RS53118B (ja) |
TN (1) | TNSN05208A1 (ja) |
WO (1) | WO2004076412A2 (ja) |
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