OA11592A - Substituted imidazo!1,2aÜazines as selective inhibitors of cox-2. - Google Patents

Substituted imidazo!1,2aÜazines as selective inhibitors of cox-2. Download PDF

Info

Publication number: OA11592A
Authority: OA; OAPI
Prior art keywords: imidazo; methylsulfonylphenyl; pyridine; pyrimidine; aminosulfonylphenyl
Prior art date: 1998-08-03

Application number

OA1200100033A

Other languages

English (en)

Inventor

Gallemi Carles Farrerons

Ignacio-Jose Miquel Bono

Ana Maria Fernandez Serrat

Carlos Monserrat Vidal

Carmen Lagunas Arnal

Ferran Gimenez Guasch

Andres Fernandez Garcia

Original Assignee

Salvat Lab Sa

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.)

1998-08-03

Filing date

1999-07-23

Publication date

2004-07-30

1999-07-23 Application filed by Salvat Lab Sa filed Critical Salvat Lab Sa

2004-07-30 Publication of OA11592A publication Critical patent/OA11592A/en

Links

101150071146 COX2 gene Proteins 0.000 title 1
101100114534 Caenorhabditis elegans ctc-2 gene Proteins 0.000 title 1
101150000187 PTGS2 gene Proteins 0.000 title 1
229940124639 Selective inhibitor Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 91
229910052794 bromium Inorganic materials 0.000 claims abstract description 15
229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
201000010099 disease Diseases 0.000 claims abstract description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
230000001404 mediated effect Effects 0.000 claims abstract description 6
239000002798 polar solvent Substances 0.000 claims abstract description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 37
-1 4-methylsulfonylphenyl Chemical group 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 33
INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 claims description 31
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 25
239000008194 pharmaceutical composition Substances 0.000 claims description 7
230000004054 inflammatory process Effects 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
206010061218 Inflammation Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
MGGFNZWFWJBUPD-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 MGGFNZWFWJBUPD-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
YSWWOBKIEHJRSO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=CC2=N1 YSWWOBKIEHJRSO-UHFFFAOYSA-N 0.000 claims description 3
SSARXDLPJGIOOC-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 SSARXDLPJGIOOC-UHFFFAOYSA-N 0.000 claims description 3
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206010028980 Neoplasm Diseases 0.000 claims description 3
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230000008569 process Effects 0.000 claims description 3
VHQYBEUFSFJFDF-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 VHQYBEUFSFJFDF-UHFFFAOYSA-N 0.000 claims description 2
HEDBESBDRYVCHB-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1C=CC=N2 HEDBESBDRYVCHB-UHFFFAOYSA-N 0.000 claims description 2
WZFGZCSDTVNFST-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C2N1C=CC=N2 WZFGZCSDTVNFST-UHFFFAOYSA-N 0.000 claims description 2
RBPODQILINHERL-UHFFFAOYSA-N 2-(4-methylphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 RBPODQILINHERL-UHFFFAOYSA-N 0.000 claims description 2
MREPIUCTDXEEHJ-UHFFFAOYSA-N 7-methyl-2-(4-methylphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC(C)=NC2=N1 MREPIUCTDXEEHJ-UHFFFAOYSA-N 0.000 claims description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
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208000016057 CHAND syndrome Diseases 0.000 claims 2
201000011510 cancer Diseases 0.000 claims 2
MMTGPHUVVVBSCZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 MMTGPHUVVVBSCZ-UHFFFAOYSA-N 0.000 claims 1
DQPPTYLEJWHRSJ-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C)C(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 DQPPTYLEJWHRSJ-UHFFFAOYSA-N 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
229940125810 compound 20 Drugs 0.000 claims 1
238000006482 condensation reaction Methods 0.000 claims 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 abstract description 21
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238000006243 chemical reaction Methods 0.000 abstract description 9
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230000001562 ulcerogenic effect Effects 0.000 abstract description 2
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 78
239000000543 intermediate Substances 0.000 description 61
239000007787 solid Substances 0.000 description 42
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
239000000243 solution Substances 0.000 description 32
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

OA1200100033A 1998-08-03 1999-07-23 Substituted imidazo!1,2aÜazines as selective inhibitors of cox-2. OA11592A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES009801652A ES2140354B1 (es)	1998-08-03	1998-08-03	Imidazo (1,2a) azinas sustituidas como inhibidores selectivos de la cox-2.

Publications (1)

Publication Number	Publication Date
OA11592A true OA11592A (en)	2004-07-30

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OA1200100033A OA11592A (en)	1998-08-03	1999-07-23	Substituted imidazo!1,2aÜazines as selective inhibitors of cox-2.

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US (1)	US6670365B1 (fr)
EP (1)	EP1104762B1 (fr)
JP (1)	JP2002522438A (fr)
KR (1)	KR20010079602A (fr)
CN (1)	CN1131865C (fr)
AP (1)	AP2001002082A0 (fr)
AT (1)	ATE224391T1 (fr)
AU (1)	AU749770B2 (fr)
BG (1)	BG105299A (fr)
BR (1)	BR9912968A (fr)
CA (1)	CA2339187A1 (fr)
CZ (1)	CZ291783B6 (fr)
DE (1)	DE69903046T2 (fr)
DK (1)	DK1104762T3 (fr)
EA (1)	EA003399B1 (fr)
ES (2)	ES2140354B1 (fr)
HU (1)	HUP0103004A3 (fr)
ID (1)	ID28539A (fr)
IL (1)	IL141242A0 (fr)
MX (1)	MXPA01001332A (fr)
NO (1)	NO20010568L (fr)
NZ (1)	NZ510196A (fr)
OA (1)	OA11592A (fr)
PL (1)	PL345804A1 (fr)
PT (1)	PT1104762E (fr)
SK (1)	SK1662001A3 (fr)
TR (1)	TR200100359T2 (fr)
WO (1)	WO2000008024A1 (fr)
YU (1)	YU7401A (fr)
ZA (1)	ZA200101632B (fr)

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1998
- 1998-08-03 ES ES009801652A patent/ES2140354B1/es not_active Expired - Lifetime
1999
- 1999-07-23 CA CA002339187A patent/CA2339187A1/fr not_active Abandoned
- 1999-07-23 YU YU7401A patent/YU7401A/sh unknown
- 1999-07-23 ES ES99931266T patent/ES2182546T3/es not_active Expired - Lifetime
- 1999-07-23 MX MXPA01001332A patent/MXPA01001332A/es unknown
- 1999-07-23 PL PL99345804A patent/PL345804A1/xx not_active IP Right Cessation
- 1999-07-23 ID IDW20010517A patent/ID28539A/id unknown
- 1999-07-23 CN CN998116750A patent/CN1131865C/zh not_active Expired - Fee Related
- 1999-07-23 NZ NZ510196A patent/NZ510196A/xx unknown
- 1999-07-23 KR KR1020017001453A patent/KR20010079602A/ko not_active Ceased
- 1999-07-23 AU AU47824/99A patent/AU749770B2/en not_active Ceased
- 1999-07-23 OA OA1200100033A patent/OA11592A/en unknown
- 1999-07-23 IL IL14124299A patent/IL141242A0/xx unknown
- 1999-07-23 SK SK166-2001A patent/SK1662001A3/sk unknown
- 1999-07-23 CZ CZ2001433A patent/CZ291783B6/cs not_active IP Right Cessation
- 1999-07-23 EA EA200100212A patent/EA003399B1/ru not_active IP Right Cessation
- 1999-07-23 BR BR9912968-0A patent/BR9912968A/pt not_active IP Right Cessation
- 1999-07-23 HU HU0103004A patent/HUP0103004A3/hu unknown
- 1999-07-23 JP JP2000563657A patent/JP2002522438A/ja active Pending
- 1999-07-23 PT PT99931266T patent/PT1104762E/pt unknown
- 1999-07-23 AT AT99931266T patent/ATE224391T1/de not_active IP Right Cessation
- 1999-07-23 DE DE69903046T patent/DE69903046T2/de not_active Expired - Fee Related
- 1999-07-23 EP EP99931266A patent/EP1104762B1/fr not_active Expired - Lifetime
- 1999-07-23 AP APAP/P/2001/002082A patent/AP2001002082A0/en unknown
- 1999-07-23 DK DK99931266T patent/DK1104762T3/da active
- 1999-07-23 WO PCT/ES1999/000235 patent/WO2000008024A1/fr not_active Ceased
- 1999-07-23 TR TR2001/00359T patent/TR200100359T2/xx unknown
- 1999-07-23 US US09/762,146 patent/US6670365B1/en not_active Expired - Fee Related
2001
- 2001-02-02 NO NO20010568A patent/NO20010568L/no not_active Application Discontinuation
- 2001-02-27 ZA ZA200101632A patent/ZA200101632B/en unknown
- 2001-02-28 BG BG105299A patent/BG105299A/xx unknown

Also Published As

Publication number	Publication date
JP2002522438A (ja)	2002-07-23
MXPA01001332A (es)	2002-11-29
EP1104762A1 (fr)	2001-06-06
DE69903046D1 (de)	2002-10-24
IL141242A0 (en)	2002-03-10
ZA200101632B (en)	2001-08-30
DE69903046T2 (de)	2003-05-22
EA200100212A1 (ru)	2001-08-27
BR9912968A (pt)	2001-05-08
DK1104762T3 (da)	2002-10-21
CA2339187A1 (fr)	2000-02-17
YU7401A (sh)	2003-10-31
NO20010568L (no)	2001-04-02
EA003399B1 (ru)	2003-04-24
SK1662001A3 (en)	2001-08-06
AU4782499A (en)	2000-02-28
CN1321157A (zh)	2001-11-07
HUP0103004A2 (hu)	2002-01-28
EP1104762B1 (fr)	2002-09-18
ES2140354B1 (es)	2000-11-01
ID28539A (id)	2001-05-31
CZ291783B6 (cs)	2003-05-14
CZ2001433A3 (cs)	2001-08-15
KR20010079602A (ko)	2001-08-22
ATE224391T1 (de)	2002-10-15
AP2001002082A0 (en)	2001-03-31
NZ510196A (en)	2002-09-27
BG105299A (en)	2001-11-30
WO2000008024A1 (fr)	2000-02-17
ES2140354A1 (es)	2000-02-16
HUP0103004A3 (en)	2003-03-28
ES2182546T3 (es)	2003-03-01
PL345804A1 (en)	2002-01-02
HK1037629A1 (en)	2002-02-15
PT1104762E (pt)	2002-11-29
NO20010568D0 (no)	2001-02-02
AU749770B2 (en)	2002-07-04
US6670365B1 (en)	2003-12-30
CN1131865C (zh)	2003-12-24
TR200100359T2 (tr)	2001-06-21

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DK149590B (da)	1986-08-04	Analogifremgangsmaade til fremstilling af 2-aryl-3,4-diaza-bicyclo(4,1,0)hepten-(2)-on-(5)-forbindelser
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HK1037629B (en)	2003-05-02	Substituted imidazo [1,2a]azines as selective inhibitors of cox-2
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JPWO1997035850A1 (ja)	1999-05-18	３−（イソオキサゾール−５−イル）置換安息香酸誘導体およびその製造法
JP2711435B2 (ja)	1998-02-10	新規な２，３−ジヒドロ−４ｈ−１−ベンゾピラン−４−オン誘導体またはその塩
SK4202000A3 (en)	2000-10-09	Process of making 3-aryloxy-4-aryl furan-2-ones useful as inhibitors of cox-2
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