ZA200101632B - Substituted imidazo[1,2A]azines as selective inhibitors of cox-2. - Google Patents

Substituted imidazo[1,2A]azines as selective inhibitors of cox-2. Download PDF

Info

Publication number: ZA200101632B
Authority: ZA; South Africa
Prior art keywords: imidazo; methylsulfonylphenyl; aminosulfonylphenyl; pyrimidine; compound
Prior art date: 1998-08-03

Application number

ZA200101632A

Other languages

English (en)

Inventor

Carles Farrerons Gallemi

Ignacio-Jose Miquel Bono

Ana Maria Fernandez Serrat

Carlos Monserrat Vidal

Carmen Lagunas Arnal

Ferran Gimenez Guasch

Andres Fernandez Garcia

Original Assignee

S A L V A T 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

2001-02-27

Publication date

2001-08-30

2001-02-27 Application filed by S A L V A T Lab Sa filed Critical S A L V A T Lab Sa

2001-08-30 Publication of ZA200101632B publication Critical patent/ZA200101632B/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
-1 4-methylsulfonylphenyl Chemical group 0.000 claims description 67
150000001875 compounds Chemical class 0.000 claims description 35
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 20
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 6
INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 claims description 5
230000005764 inhibitory process Effects 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 4
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 4
239000002253 acid Substances 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
229940111134 coxibs Drugs 0.000 claims description 3
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
206010061218 Inflammation Diseases 0.000 claims description 2
239000012453 solvate Substances 0.000 claims description 2
201000010099 disease Diseases 0.000 claims 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 4
239000003937 drug carrier Substances 0.000 claims 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
230000001404 mediated effect Effects 0.000 claims 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
239000008194 pharmaceutical composition Substances 0.000 claims 3
206010028980 Neoplasm Diseases 0.000 claims 2
201000011510 cancer Diseases 0.000 claims 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 1
206010009944 Colon cancer Diseases 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 claims 1
208000029742 colonic neoplasm Diseases 0.000 claims 1
238000006482 condensation reaction Methods 0.000 claims 1
125000001207 fluorophenyl group Chemical group 0.000 claims 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
230000001562 ulcerogenic effect Effects 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 78
102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 6
108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000543 intermediate Substances 0.000 description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
238000000034 method Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
230000001939 inductive effect Effects 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 2
229940124599 anti-inflammatory drug Drugs 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
RBHURFRUCSUMPN-UHFFFAOYSA-N 2-bromo-2-(4-methylsulfonylphenyl)-1-phenylethanone Chemical class C1=CC(S(=O)(=O)C)=CC=C1C(Br)C(=O)C1=CC=CC=C1 RBHURFRUCSUMPN-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
108010044467 Isoenzymes Proteins 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
208000038016 acute inflammation Diseases 0.000 description 1
230000006022 acute inflammation Effects 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical class BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000033077 cellular process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
208000037976 chronic inflammation Diseases 0.000 description 1
230000006020 chronic inflammation Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000011903 deuterated solvents‎ Substances 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000012458 free base Substances 0.000 description 1
231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
230000013632 homeostatic process Effects 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
210000004347 intestinal mucosa Anatomy 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
230000003907 kidney function Effects 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000000770 proinflammatory effect Effects 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
150000003815 prostacyclins Chemical class 0.000 description 1
229940127293 prostanoid Drugs 0.000 description 1
150000003814 prostanoids Chemical class 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
230000004044 response Effects 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000004206 stomach function Effects 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
230000002792 vascular Effects 0.000 description 1

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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (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)

ZA200101632A 1998-08-03 2001-02-27 Substituted imidazo[1,2A]azines as selective inhibitors of cox-2. ZA200101632B (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
ZA200101632B true ZA200101632B (en)	2001-08-30

Family

ID=8304755

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200101632A ZA200101632B (en)	1998-08-03	2001-02-27	Substituted imidazo[1,2A]azines as selective inhibitors of cox-2.

Country Status (30)

Country	Link
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)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EA008242B1 (ru)	1999-12-08	2007-04-27	Фармация Корпорейшн	Композиции на основе ингибитора циклооксигеназы-2 с быстро наступающим терапевтическим действием и способы лечения заболеваний
US8241622B2 (en) *	2001-07-13	2012-08-14	University Of Iowa Research Foundation	Adeno-associated virus vectors with intravector heterologous terminal palindromic sequences
US20030100594A1 (en) *	2001-08-10	2003-05-29	Pharmacia Corporation	Carbonic anhydrase inhibitor
DE10247271A1 (de) *	2002-10-10	2004-08-26	Grünenthal GmbH	Substituierte C-Imidazo[1,2-a]pyridin-3-yle
DE10256881A1 (de) *	2002-12-05	2004-06-24	Beiersdorf Ag	Neue topische Verwendung von Bis-Arylimidazo[1,2-a]thiolanderivaten
ES2275218T3 (es)	2003-05-07	2007-06-01	Osteologix A/S	Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos.
WO2005014598A1 (fr) *	2003-07-30	2005-02-17	Laboratorios S.A.L.V.A.T., S.A.	Imidazopyrimidines substituees pour la prevention et le traitement du cancer
WO2007034278A2 (fr) *	2005-09-19	2007-03-29	Pfizer Products Inc.	Antagonistes du recepteur du c3a
WO2007079141A2 (fr) *	2005-12-30	2007-07-12	University Of Iowa Research Foundation	Procede d'identification de composes utiles pour le traitement de maladies degeneratives neuronales
WO2007096764A2 (fr) *	2006-02-27	2007-08-30	Glenmark Pharmaceuticals S.A.	Dérivés d'hétéroaryles bicycliques en tant que modulateurs des récepteurs cannabinoïdes
EP2220083B1 (fr) *	2007-11-14	2017-07-19	Janssen Pharmaceuticals, Inc.	Dérivés d'imidazo[1,2-a]pyridines et leur utilisation en tant que modulateurs allostériques positifs de récepteurs mglur2
CA2739303A1 (fr) *	2008-10-01	2010-04-08	Synta Pharmaceuticals Corp.	Composes pour des utilisations liees a une inflammation et au systeme immunitaire
GB201321732D0 (en) *	2013-12-09	2014-01-22	Ucb Pharma Sa	Therapeutic agents
WO2017139381A1 (fr)	2016-02-08	2017-08-17	University Of Iowa Research Foundation	Procédés pour produire des virus adéno-associés/bocavirus parvovirus chimériques
US11684679B2 (en)	2016-03-07	2023-06-27	University Of Iowa Research Foundation	AAV-mediated expression using a synthetic promoter and enhancer
WO2017205739A1 (fr)	2016-05-26	2017-11-30	University Of Iowa Research Foundation	Configurations cis et trans pour la résolution terminale du bocavirus 1 humain
WO2018132747A1 (fr)	2017-01-13	2018-07-19	University Of Iowa Research Foundation	Petit arn non codant pour bocaparvovirus et ses utilisations
CA3209491A1 (fr)	2021-03-15	2022-09-22	Saul Yedgar	Dipalmitoyl-phosphatidyl-ethanol-amine conjuguee a l'acide hyaluronique en combinaison avec des medicaments anti-inflammatoires non steroidiens (ains) pour traiter ou soulager des maladies inflammatoire

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2785133A (en) *	1954-03-26	1957-03-12	Gen Aniline & Film Corp	Compositions for a method of whitening fine fabrics
US3455924A (en) *	1967-02-08	1969-07-15	Upjohn Co	Dianisylimidazoles
WO1992010190A1 (fr)	1990-12-13	1992-06-25	Smithkline Beecham Corporation	Nouveaux medicaments anti-inflammatoires suppresseurs de cytokine
AU3648993A (en) *	1992-03-17	1993-10-21	Nippon Shinyaku Co. Ltd.	Imidazopyridine derivative and medicine
US5620999A (en) *	1994-07-28	1997-04-15	Weier; Richard M.	Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation
KR19980703559A (ko) *	1995-04-04	1998-11-05	그레이엄브레레톤	이미다조［1,2-ａ］피리딘 유도체
UA57002C2 (uk) *	1995-10-13	2003-06-16	Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі.	Похідне (метилсульфоніл)феніл-2-(5н)-фуранону, фармацевтична композиція та спосіб лікування

1998
- 1998-08-03 ES ES009801652A patent/ES2140354B1/es not_active Expired - Lifetime
1999
- 1999-07-23 AU AU47824/99A patent/AU749770B2/en not_active Ceased
- 1999-07-23 IL IL14124299A patent/IL141242A0/xx unknown
- 1999-07-23 SK SK166-2001A patent/SK1662001A3/sk unknown
- 1999-07-23 JP JP2000563657A patent/JP2002522438A/ja active Pending
- 1999-07-23 PT PT99931266T patent/PT1104762E/pt unknown
- 1999-07-23 CA CA002339187A patent/CA2339187A1/fr not_active Abandoned
- 1999-07-23 YU YU7401A patent/YU7401A/sh unknown
- 1999-07-23 TR TR2001/00359T patent/TR200100359T2/xx unknown
- 1999-07-23 WO PCT/ES1999/000235 patent/WO2000008024A1/fr not_active Ceased
- 1999-07-23 OA OA1200100033A patent/OA11592A/en 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 US US09/762,146 patent/US6670365B1/en not_active Expired - Fee Related
- 1999-07-23 AT AT99931266T patent/ATE224391T1/de not_active IP Right Cessation
- 1999-07-23 CN CN998116750A patent/CN1131865C/zh not_active Expired - Fee Related
- 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 KR KR1020017001453A patent/KR20010079602A/ko not_active Ceased
- 1999-07-23 DE DE69903046T patent/DE69903046T2/de not_active Expired - Fee Related
- 1999-07-23 AP APAP/P/2001/002082A patent/AP2001002082A0/en unknown
- 1999-07-23 DK DK99931266T patent/DK1104762T3/da active
- 1999-07-23 HU HU0103004A patent/HUP0103004A3/hu unknown
- 1999-07-23 BR BR9912968-0A patent/BR9912968A/pt not_active IP Right Cessation
- 1999-07-23 EP EP99931266A patent/EP1104762B1/fr not_active Expired - Lifetime
- 1999-07-23 NZ NZ510196A patent/NZ510196A/xx unknown
- 1999-07-23 ID IDW20010517A patent/ID28539A/id unknown
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
EA200100212A1 (ru)	2001-08-27
NO20010568D0 (no)	2001-02-02
DE69903046T2 (de)	2003-05-22
AU4782499A (en)	2000-02-28
WO2000008024A1 (fr)	2000-02-17
PT1104762E (pt)	2002-11-29
PL345804A1 (en)	2002-01-02
NZ510196A (en)	2002-09-27
DK1104762T3 (da)	2002-10-21
YU7401A (sh)	2003-10-31
BR9912968A (pt)	2001-05-08
MXPA01001332A (es)	2002-11-29
DE69903046D1 (de)	2002-10-24
BG105299A (en)	2001-11-30
AP2001002082A0 (en)	2001-03-31
CN1321157A (zh)	2001-11-07
SK1662001A3 (en)	2001-08-06
US6670365B1 (en)	2003-12-30
CN1131865C (zh)	2003-12-24
NO20010568L (no)	2001-04-02
EP1104762B1 (fr)	2002-09-18
HUP0103004A2 (hu)	2002-01-28
AU749770B2 (en)	2002-07-04
CZ291783B6 (cs)	2003-05-14
EA003399B1 (ru)	2003-04-24
HK1037629A1 (en)	2002-02-15
ES2140354A1 (es)	2000-02-16
HUP0103004A3 (en)	2003-03-28
EP1104762A1 (fr)	2001-06-06
ES2182546T3 (es)	2003-03-01
CZ2001433A3 (cs)	2001-08-15
IL141242A0 (en)	2002-03-10
OA11592A (en)	2004-07-30
TR200100359T2 (tr)	2001-06-21
ES2140354B1 (es)	2000-11-01
JP2002522438A (ja)	2002-07-23
ATE224391T1 (de)	2002-10-15
ID28539A (id)	2001-05-31
KR20010079602A (ko)	2001-08-22
CA2339187A1 (fr)	2000-02-17

Publication	Publication Date	Title
US6670365B1 (en)	2003-12-30	Substituted imidazo 1,2a}azines as selective inhibitors of cox-2
EP1191931B1 (fr)	2007-05-09	1-(4-sulfamylphenyl)-3-trifluoromethyl-5-aryle-2-pyrazolines comme inhibiteurs de cyclo-oxygenase-2
TWI282336B (en)	2007-06-11	A61p 29/00 200601 a i vhtw
EP1246809B1 (fr)	2003-07-16	Composes de 5-aryl-1h-1,2,4-triazole en tant qu'inhibiteurs de cyclooxygenase-2 et compositions pharmaceutiques les contenant
US11136310B2 (en)	2021-10-05	Iminotetrahydropyrimidinone derivatives as plasmepsin V inhibitors
JPH11217383A (ja)	1999-08-10	化合物
BG100727A (bg)	1997-02-28	Тетрациклени производни, метод за получаване и приложение
EA007957B1 (ru)	2007-02-27	Производные тиенопиримидина, содержащая их фармацевтическая композиция и их применение
JP2002533439A (ja)	2002-10-08	グルカゴン拮抗剤または逆作用剤
AU729386B2 (en)	2001-02-01	1,2-diarylindole as cox-2 inhibitors
GB2193961A (en)	1988-02-24	3-hydroxybenzo(b)thiophene-2-carboxamides
EP0521768B1 (fr)	1994-02-02	Nouveaux dérivés de triazolopyrimidine antagonistes des récepteurs à l'angiotensine II; leurs procédés de préparation, compositions pharmaceutiques les contenant
CA2534292A1 (fr)	2005-02-17	Imidazopyrimidines substituees pour la prevention et le traitement du cancer
JP4007743B2 (ja)	2007-11-14	血管新生阻害剤
JPH11228538A (ja)	1999-08-24	新規なピロール化合物、その製造方法及びそれを含有する医薬組成物
CN105531270B (zh)	2017-09-05	(+)－5－(3，4－二氟苯基)－5－[(3－甲基－2－氧吡啶－1(2h)－基)甲基]咪唑烷－2，4－二酮及含有该化合物的药物
WO2001032658A1 (fr)	2001-05-10	Compose de polyazanaphtalene et utilisation medicinale dudit compose
KR20020081254A (ko)	2002-10-26	융합된 피롤 화합물, 이를 포함하는 제약 제제, 및 이의용도
JP2002512222A (ja)	2002-04-23	４−ヒドロキシインドール、インダゾール、及び、カルバゾール化合物の製造方法
HK1037629B (en)	2003-05-02	Substituted imidazo [1,2a]azines as selective inhibitors of cox-2
CN117886747A (zh)	2024-04-16	氟代甲基取代喹啉类化合物、应用、药物组合物、合成方法
Rahim et al.	2002	Synthesis of 4‐alkyl‐1, 2‐diphenyl‐3, 5‐dioxopyrazolidines possessing aryl methylsulfonyl and sulfonamide pharmacophores for evaluation as selective cyclooxygenase‐2 (COX‐2) inhibitors
Lin	2023	Copper Catalyzed Oxidative Cascade Double Cyclization of 2–Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindoli-None Derivatives One-Pot Three-Component Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Trisubstituted Pyridines Synthesis of Isoindolo [1, 2-b] quinazolin-12 (10H)-One and 5, 13-Dihydro-11Hquinazolino [2, 3-b] quinazolin-11-One Derivatives via Copper Catalyzed Tandem Cyclization
JP3167700B1 (ja)	2001-05-21	２，３−ジアリール−ピラゾロ［１，５−ｂ］ピリダジン誘導体、その製造方法およびそのシクロオキシゲナーゼ２（ｃｏｘ−２）阻害剤としての使用
CN109748872A (zh)	2019-05-14	一类含二芳基吡唑骨架的吗啉衍生物抗肿瘤化合物的设计与合成