SK10272003A3 - Triazolopyrimidýny ako protizápalové činidlá - Google Patents

Triazolopyrimidýny ako protizápalové činidlá Download PDF

Info

Publication number: SK10272003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; phenyl; cycloalkyl; heteroaryl; heterocycle
Prior art date: 2001-03-09

Application number

SK1027-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Mark Anthony Dombroski

Allen Jacob Duplantier

Ellen Ruth Laird

Michael Anthony Letavic

Kim Francis Mcclure

Original Assignee

Pfizer Products Inc.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-03-09

Filing date

2002-02-08

Publication date

2004-07-07

2002-02-08 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2004-07-07 Publication of SK10272003A3 publication Critical patent/SK10272003A3/sk

Links

150000008523 triazolopyridines Chemical class 0.000 title abstract description 4
239000002260 anti-inflammatory agent Substances 0.000 title description 3
229940121363 anti-inflammatory agent Drugs 0.000 title description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 385
150000001875 compounds Chemical class 0.000 claims abstract description 357
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 133
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 113
239000001257 hydrogen Substances 0.000 claims abstract description 112
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 87
125000001424 substituent group Chemical group 0.000 claims abstract description 53
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 48
238000011282 treatment Methods 0.000 claims abstract description 33
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
125000005842 heteroatom Chemical group 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
102000043136 MAP kinase family Human genes 0.000 claims abstract description 8
108091054455 MAP kinase family Proteins 0.000 claims abstract description 8
229910052760 oxygen Chemical group 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 249
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 187
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 111
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 85
125000003545 alkoxy group Chemical group 0.000 claims description 83
229910052736 halogen Inorganic materials 0.000 claims description 78
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 77
150000002367 halogens Chemical class 0.000 claims description 77
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 72
-1 phenyl- Chemical group 0.000 claims description 72
125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 67
150000003839 salts Chemical class 0.000 claims description 57
125000001072 heteroaryl group Chemical group 0.000 claims description 51
125000004093 cyano group Chemical group *C#N 0.000 claims description 48
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 45
125000003282 alkyl amino group Chemical group 0.000 claims description 44
201000010099 disease Diseases 0.000 claims description 44
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 44
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 43
238000000034 method Methods 0.000 claims description 38
125000000753 cycloalkyl group Chemical group 0.000 claims description 35
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 31
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 30
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 23
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 20
230000002401 inhibitory effect Effects 0.000 claims description 19
241000124008 Mammalia Species 0.000 claims description 18
125000003342 alkenyl group Chemical group 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
230000001404 mediated effect Effects 0.000 claims description 7
QSVDXGHEPKIJAK-UHFFFAOYSA-N 2-methyl-4-phenyl-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC(C)=NC=1C1=CC=CC=C1 QSVDXGHEPKIJAK-UHFFFAOYSA-N 0.000 claims description 5
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
GGUWFBJTYKFSCP-UHFFFAOYSA-N 4-phenyl-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=CC=C1 GGUWFBJTYKFSCP-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 3
LXNCCRGRUITJBS-UHFFFAOYSA-N 4-(3-methylphenyl)-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=CC(C)=C1 LXNCCRGRUITJBS-UHFFFAOYSA-N 0.000 claims description 3
QNWAANUBKXAVBR-UHFFFAOYSA-N 4-(4-fluoro-3-methylphenyl)-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C(C)=C1 QNWAANUBKXAVBR-UHFFFAOYSA-N 0.000 claims description 3
QCJWBKMIGDTPMY-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(3-phenyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C1=CC(F)=CC=C1C1=C(C2=CN3C(C=4C=CC=CC=4)=NN=C3C=C2)OC=N1 QCJWBKMIGDTPMY-UHFFFAOYSA-N 0.000 claims description 3
GTASFDBWCNBHIU-UHFFFAOYSA-N 5-(3-cyclobutyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(3-methylphenyl)-1,3-oxazole Chemical compound CC1=CC=CC(C2=C(OC=N2)C2=CN3C(C4CCC4)=NN=C3C=C2)=C1 GTASFDBWCNBHIU-UHFFFAOYSA-N 0.000 claims description 3
FKFMKIWLJONUTR-UHFFFAOYSA-N 5-(3-cyclobutyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-phenyl-1,3-oxazole Chemical compound C1CCC1C1=NN=C2N1C=C(C1=C(N=CO1)C=1C=CC=CC=1)C=C2 FKFMKIWLJONUTR-UHFFFAOYSA-N 0.000 claims description 3
MSICXESVKFNJFX-UHFFFAOYSA-N 5-(3-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(4-fluoro-3-methylphenyl)-1,3-oxazole Chemical compound C1=C(F)C(C)=CC(C2=C(OC=N2)C2=CN3C(C4CC4)=NN=C3C=C2)=C1 MSICXESVKFNJFX-UHFFFAOYSA-N 0.000 claims description 3
YLYUFKWQQAJIFH-UHFFFAOYSA-N 5-(3-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-phenyl-1,3-oxazole Chemical compound C1CC1C1=NN=C2N1C=C(C1=C(N=CO1)C=1C=CC=CC=1)C=C2 YLYUFKWQQAJIFH-UHFFFAOYSA-N 0.000 claims description 3
JEJAABNZDXVBDR-UHFFFAOYSA-N 5-(3-ethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(3-methylphenyl)-1,3-oxazole Chemical compound C=1N2C(CC)=NN=C2C=CC=1C=1OC=NC=1C1=CC=CC(C)=C1 JEJAABNZDXVBDR-UHFFFAOYSA-N 0.000 claims description 3
HVGGHEUBVDQWKM-UHFFFAOYSA-N 5-(3-ethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(4-fluorophenyl)-1,3-oxazole Chemical compound C=1N2C(CC)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 HVGGHEUBVDQWKM-UHFFFAOYSA-N 0.000 claims description 3
GHTYLDSZYTWMCU-UHFFFAOYSA-N 5-(3-ethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-phenyl-1,3-oxazole Chemical compound C=1N2C(CC)=NN=C2C=CC=1C=1OC=NC=1C1=CC=CC=C1 GHTYLDSZYTWMCU-UHFFFAOYSA-N 0.000 claims description 3
OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 claims description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
KCQBEZKOAYRYIZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-methyl-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC(C)=NC=1C1=CC=C(F)C=C1 KCQBEZKOAYRYIZ-UHFFFAOYSA-N 0.000 claims description 2
QFVILCCNFWNYAN-UHFFFAOYSA-N 5-(3-cyclobutyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(4-fluorophenyl)-1,3-oxazole Chemical compound C1=CC(F)=CC=C1C1=C(C2=CN3C(C4CCC4)=NN=C3C=C2)OC=N1 QFVILCCNFWNYAN-UHFFFAOYSA-N 0.000 claims description 2
HTRYISKMFSYGKQ-UHFFFAOYSA-N 5-(3-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(4-fluorophenyl)-1,3-oxazole Chemical compound C1=CC(F)=CC=C1C1=C(C2=CN3C(C4CC4)=NN=C3C=C2)OC=N1 HTRYISKMFSYGKQ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications

- C—CHEMISTRY; METALLURGY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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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
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
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Biomedical Technology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Pulmonology (AREA)
Psychiatry (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Cardiology (AREA)
Communicable Diseases (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Vascular Medicine (AREA)
Oncology (AREA)
Toxicology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK1027-2003A 2001-03-09 2002-02-08 Triazolopyrimidýny ako protizápalové činidlá SK10272003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US27484001P	2001-03-09	2001-03-09
PCT/IB2002/000424 WO2002072579A1 (fr)	2001-03-09	2002-02-08	Triazolopyridines, agents anti-inflammatoires

Publications (1)

Publication Number	Publication Date
SK10272003A3 true SK10272003A3 (sk)	2004-07-07

Family

ID=23049813

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1027-2003A SK10272003A3 (sk)	2001-03-09	2002-02-08	Triazolopyrimidýny ako protizápalové činidlá

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EP (1)	EP1370559B1 (fr)
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CN (1)	CN1496366A (fr)
AP (1)	AP2002002463A0 (fr)
AR (1)	AR036152A1 (fr)
AT (1)	ATE323701T1 (fr)
BG (1)	BG108133A (fr)
BR (1)	BR0207990A (fr)
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CR (1)	CR7013A (fr)
CZ (1)	CZ20032185A3 (fr)
DE (1)	DE60210755T2 (fr)
DO (1)	DOP2002000353A (fr)
EA (1)	EA200300864A1 (fr)
EC (1)	ECSP034762A (fr)
EE (1)	EE200300437A (fr)
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Publication number	Publication date
ES2260415T3 (es)	2006-11-01
NO20033969L (no)	2003-10-13
AR036152A1 (es)	2004-08-18
NZ526528A (en)	2005-02-25
ATE323701T1 (de)	2006-05-15
IS6858A (is)	2003-06-23
OA12552A (en)	2006-06-06
KR20030080087A (ko)	2003-10-10
GT200200042A (es)	2003-02-11
UY27199A1 (es)	2002-10-31
EP1370559A1 (fr)	2003-12-17
BG108133A (bg)	2004-09-30
WO2002072579A1 (fr)	2002-09-19
PE20030010A1 (es)	2003-01-29
EE200300437A (et)	2004-02-16
JP2004522799A (ja)	2004-07-29
PA8541001A1 (es)	2003-05-14
BR0207990A (pt)	2004-04-27
ZA200304983B (en)	2004-06-29
ECSP034762A (es)	2003-10-28
US20030096838A1 (en)	2003-05-22
JP4130774B2 (ja)	2008-08-06
DE60210755D1 (de)	2006-05-24
NO20033969D0 (no)	2003-09-08
DOP2002000353A (es)	2002-10-15
DE60210755T2 (de)	2006-11-16
TNSN02022A1 (fr)	2005-12-23
HUP0303415A2 (hu)	2004-01-28
CR7013A (es)	2003-11-25
US6696464B2 (en)	2004-02-24
CN1496366A (zh)	2004-05-12
AP2002002463A0 (en)	2002-06-30
MXPA03008144A (es)	2003-12-12
MA26991A1 (fr)	2004-12-20
IL156567A0 (en)	2004-01-04
EA200300864A1 (ru)	2003-12-25
CA2440222C (fr)	2008-11-18
PL363959A1 (en)	2004-11-29
CZ20032185A3 (en)	2004-06-16
CA2440222A1 (fr)	2002-09-19
EP1370559B1 (fr)	2006-04-19
HRP20030719A2 (en)	2005-04-30

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JP3832646B2 (ja)	2006-10-11	新規ベンゾトリアゾール抗炎症化合物
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US8022085B2 (en)	2011-09-20	Pyrazolo-pyridinone and pyrazolo-pyrazinone compounds as P38 modulators and methods of use thereof
JP2004529926A (ja)	2004-09-30	抗ウイルス性ピラゾロピリジン化合物
WO2004072072A1 (fr)	2004-08-26	Triazolo-pyridines utilisees comme composes anti-inflammatoires
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