SK1492004A3 - Spirocyclic-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines - Google Patents

Spirocyclic-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines Download PDF

Info

Publication number: SK1492004A3
Authority: SK; Slovakia
Prior art keywords: fluorophenyl; substituted; unsubstituted; dihydro; pyrazolo
Prior art date: 2001-09-20

Application number

SK149-2004A

Other languages

English (en)

Slovak (sk)

Inventor

Matthew John Laufersweiler

Michael Phillip Clark

Jane Far-Jine Djung

Adam Golebiowski

Biswanath De

Todd Andrew Brugel

Original Assignee

Procter & Gamble

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.)

2001-09-20

Filing date

2002-09-20

Publication date

2004-11-03

2002-09-20 Application filed by Procter & Gamble filed Critical Procter & Gamble

2004-11-03 Publication of SK1492004A3 publication Critical patent/SK1492004A3/sk

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102000004127 Cytokines Human genes 0.000 title claims abstract description 37
108090000695 Cytokines Proteins 0.000 title claims abstract description 37
230000002757 inflammatory effect Effects 0.000 title claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 60
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
239000001257 hydrogen Substances 0.000 claims abstract description 50
239000000203 mixture Chemical group 0.000 claims abstract description 35
125000003118 aryl group Chemical group 0.000 claims abstract description 29
125000004429 atom Chemical group 0.000 claims abstract description 24
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 23
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
229910052799 carbon Inorganic materials 0.000 claims abstract description 14
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
-1 C 1 -C 4 alkyl Substances 0.000 claims description 243
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 74
125000003003 spiro group Chemical group 0.000 claims description 64
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 32
150000002431 hydrogen Chemical class 0.000 claims description 28
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 11
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 11
125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 10
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 10
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
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150000001768 cations Chemical class 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
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125000005275 alkylenearyl group Chemical group 0.000 claims description 6
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125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 4
WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 2
125000006317 cyclopropyl amino group Chemical group 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 9
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
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229920002554 vinyl polymer Polymers 0.000 claims 5
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125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 4
150000002170 ethers Chemical class 0.000 abstract description 13
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102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 8
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ISQQEOJMKNIJEL-UHFFFAOYSA-N 2-phenoxypyrimidine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC(OC=2C=CC=CC=2)=N1 ISQQEOJMKNIJEL-UHFFFAOYSA-N 0.000 description 7
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MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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125000006091 1,3-dioxolane group Chemical group 0.000 description 4
IVERDAYMMYMUSY-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)acetyl]pyrazolidin-4-one Chemical compound C1=CC(F)=CC=C1CC(=O)N1NCC(=O)C1 IVERDAYMMYMUSY-UHFFFAOYSA-N 0.000 description 4
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STKARFFXWORTNB-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazolo[1,2-a]pyrazol-5-one Chemical group C1CCN2C(=O)C=CN21 STKARFFXWORTNB-UHFFFAOYSA-N 0.000 description 3
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RTPFMAMJLAQCFM-UHFFFAOYSA-N 4-methylidene-2-phenylmethoxycarbonylpyrazolidine-1-carboxylic acid Chemical compound OC(=O)N1CC(=C)CN1C(=O)OCC1=CC=CC=C1 RTPFMAMJLAQCFM-UHFFFAOYSA-N 0.000 description 1
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WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
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238000011161 development Methods 0.000 description 1
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102000057041 human TNF Human genes 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
ONLQTQQQTMANMX-UHFFFAOYSA-N methyl 2-phenoxypyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(OC=2C=CC=CC=2)=N1 ONLQTQQQTMANMX-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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125000003373 pyrazinyl group Chemical group 0.000 description 1
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125000000168 pyrrolyl group Chemical group 0.000 description 1
238000012797 qualification Methods 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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235000017557 sodium bicarbonate Nutrition 0.000 description 1
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GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
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150000003457 sulfones Chemical class 0.000 description 1
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239000006228 supernatant Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000006433 tumor necrosis factor production 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
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/20—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Heart & Thoracic Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Hematology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SK149-2004A 2001-09-20 2002-09-20 Spirocyclic-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines SK1492004A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US32362501P	2001-09-20	2001-09-20
PCT/US2002/030133 WO2003024973A1 (en)	2001-09-20	2002-09-20	Spirocyclic-6,7-dihydro-5h-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines

Publications (1)

Publication Number	Publication Date
SK1492004A3 true SK1492004A3 (en)	2004-11-03

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ID=23259997

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
SK149-2004A SK1492004A3 (en)	2001-09-20	2002-09-20	Spirocyclic-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
SK148-2004A SK1482004A3 (en)	2001-09-20	2002-09-20	Compounds which inhibit the release of inflammatory cytokines
SK150-2004A SK1502004A3 (en)	2001-09-20	2002-09-20	6,7-Dihydro-5H-pyrazolo[1,2-a] pyrazol-1-ones regulating inflammatory cytokines

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
SK148-2004A SK1482004A3 (en)	2001-09-20	2002-09-20	Compounds which inhibit the release of inflammatory cytokines
SK150-2004A SK1502004A3 (en)	2001-09-20	2002-09-20	6,7-Dihydro-5H-pyrazolo[1,2-a] pyrazol-1-ones regulating inflammatory cytokines

Country Status (32)

Country	Link
US (2)	US6821971B2 (cs)
EP (3)	EP1427732B1 (cs)
JP (3)	JP2005504081A (cs)
KR (4)	KR20040035837A (cs)
CN (3)	CN1249066C (cs)
AR (3)	AR037502A1 (cs)
AT (3)	ATE287887T1 (cs)
AU (2)	AU2002334641B2 (cs)
BR (3)	BR0212673A (cs)
CA (3)	CA2461073A1 (cs)
CO (3)	CO5560590A2 (cs)
CY (1)	CY1106398T1 (cs)
CZ (3)	CZ2004361A3 (cs)
DE (3)	DE60213108T2 (cs)
DK (2)	DK1427728T3 (cs)
EG (2)	EG24413A (cs)
ES (3)	ES2237691T3 (cs)
HU (3)	HUP0500752A2 (cs)
IL (3)	IL160741A0 (cs)
MA (3)	MA27065A1 (cs)
MX (3)	MXPA04002574A (cs)
MY (2)	MY129329A (cs)
NO (2)	NO20041594L (cs)
NZ (3)	NZ531123A (cs)
PE (3)	PE20030430A1 (cs)
PL (3)	PL370415A1 (cs)
PT (3)	PT1427728E (cs)
RU (3)	RU2299885C2 (cs)
SA (1)	SA03230529B1 (cs)
SK (3)	SK1492004A3 (cs)
WO (3)	WO2003024973A1 (cs)
ZA (3)	ZA200401260B (cs)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7087615B2 (en)	2001-09-20	2006-08-08	The Procter & Gamble Company	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which provide analgesia
US6849627B2 (en)	2001-09-20	2005-02-01	The Procter & Gamble Company	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
US6730668B2 (en) *	2001-09-20	2004-05-04	The Procter & Gamble Company	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
US7473695B2 (en) *	2001-10-22	2009-01-06	Mitsubishi Tanabe Pharma Corporation	4-imidazolin-2-one compounds
US6677337B2 (en) *	2002-03-19	2004-01-13	The Procter & Gamble Company	1,2-dihydropyrazol-3-ones which controls inflammatory cytokines
US6967254B2 (en) *	2002-09-09	2005-11-22	Amgen Inc.	Substituted heterocyclic compounds and methods of use
CA2520894C (en) *	2003-04-03	2013-02-05	Werner Mederski	Pyrazolidine-1,2-dicarboxyldiphenylamide derivatives as coagulation factor xa inhibitors for the treatment of thromboses
GB0308466D0 (en) *	2003-04-11	2003-05-21	Novartis Ag	Organic compounds
US7482356B2 (en) *	2003-11-10	2009-01-27	The Procter & Gamble Company	Bicyclic pyrazolone cytokine inhibitors
KR20080111144A (ko) *	2006-04-18	2008-12-22	아보트 러보러터리즈	바닐로이드 수용체 서브타입 １(ｖｒ１)의 길항제 및 이의 용도
DE102008060549A1 (de)	2008-12-04	2010-06-10	MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V.	Wirkstoff-Peptid-Konstrukt zur extrazellulären Anreicherung
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2002
- 2002-09-18 US US10/245,927 patent/US6821971B2/en not_active Expired - Fee Related
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2007
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Also Published As

Publication number	Publication date
PL370351A1 (en)	2005-05-16
HUP0402500A2 (hu)	2005-03-29
NZ531123A (en)	2006-08-31
NO20041605L (no)	2004-06-21
PL370415A1 (en)	2005-05-30
PE20030430A1 (es)	2003-06-24
ATE356126T1 (de)	2007-03-15
ZA200401403B (en)	2004-08-30
DK1427728T3 (da)	2007-07-09
CO5560590A2 (es)	2005-09-30
MXPA04002574A (es)	2004-06-18
RU2278864C2 (ru)	2006-06-27
DE60218704T2 (de)	2007-11-08
CZ2004358A3 (cs)	2004-07-14
CO5560579A2 (es)	2005-09-30
NZ531063A (en)	2007-08-31
KR20060036125A (ko)	2006-04-27
ZA200401260B (en)	2004-08-30
PE20030474A1 (es)	2003-07-22
KR100656126B1 (ko)	2006-12-12
ES2268154T3 (es)	2007-03-16
CN1555379A (zh)	2004-12-15
NZ531122A (en)	2005-09-30
EP1427727B1 (en)	2005-01-26
DE60213108T2 (de)	2007-02-08
SK1482004A3 (en)	2004-08-03
JP2005504083A (ja)	2005-02-10
BR0212905A (pt)	2004-10-13
AR037502A1 (es)	2004-11-17
AU2002327690B2 (en)	2006-07-20
MXPA04002570A (es)	2004-05-31
PT1427732E (pt)	2006-12-29
ATE332901T1 (de)	2006-08-15
HUP0402500A3 (en)	2008-10-28
NO20041594L (no)	2004-06-21
WO2003024973A1 (en)	2003-03-27
PT1427728E (pt)	2007-05-31
CN1250551C (zh)	2006-04-12
DE60213108D1 (de)	2006-08-24
CZ2004345A3 (cs)	2004-06-16
EP1427732B1 (en)	2006-07-12
HUP0402378A2 (hu)	2005-02-28
ES2237691T3 (es)	2005-08-01
IL160741A0 (en)	2004-08-31
US20030105084A1 (en)	2003-06-05
PT1427727E (pt)	2005-06-30
CN1555375A (zh)	2004-12-15
CN1249066C (zh)	2006-04-05
BR0212673A (pt)	2004-08-24
AR037237A1 (es)	2004-11-03
CA2461072A1 (en)	2003-03-27
DK1427732T3 (da)	2006-10-30
AR037145A1 (es)	2004-10-27
EG24413A (en)	2009-05-25
DE60202782T2 (de)	2006-01-19
JP2005504081A (ja)	2005-02-10
US6821971B2 (en)	2004-11-23
RU2004111806A (ru)	2005-03-27
EP1427728B1 (en)	2007-03-07
KR20040035835A (ko)	2004-04-29
CA2461073A1 (en)	2003-03-27
SA03230529B1 (ar)	2008-06-21
BR0212716A (pt)	2004-08-03
AU2002334641B2 (en)	2007-03-29
CA2461071A1 (en)	2003-03-27
HUP0500752A2 (en)	2006-01-30
CY1106398T1 (el)	2011-10-12
ZA200401402B (en)	2004-08-27
HK1071565A1 (en)	2005-07-22
SK1502004A3 (en)	2004-09-08
EP1427728A1 (en)	2004-06-16
CZ2004361A3 (cs)	2004-07-14
KR20040035837A (ko)	2004-04-29
MA27064A1 (fr)	2004-12-20
PL370362A1 (en)	2005-05-16
CN1556811A (zh)	2004-12-22
RU2004111805A (ru)	2005-04-10
RU2272040C2 (ru)	2006-03-20
MXPA04002569A (es)	2004-05-31
US6566357B1 (en)	2003-05-20
KR100623879B1 (ko)	2006-09-19
IL160682A0 (en)	2004-08-31
KR20040035836A (ko)	2004-04-29
MY129329A (en)	2007-03-30
WO2003024970A1 (en)	2003-03-27
JP2005504082A (ja)	2005-02-10
EG24363A (en)	2009-03-04
ATE287887T1 (de)	2005-02-15
ES2282459T3 (es)	2007-10-16
HK1071366A1 (en)	2005-07-15
DE60202782D1 (de)	2005-03-03
CO5560589A2 (es)	2005-09-30
CN1257905C (zh)	2006-05-31
PE20030446A1 (es)	2003-07-21
WO2003024971A1 (en)	2003-03-27
EP1427732A1 (en)	2004-06-16
EP1427727A1 (en)	2004-06-16
IL160742A0 (en)	2004-08-31
HUP0402378A3 (en)	2008-10-28
RU2299885C2 (ru)	2007-05-27
DE60218704D1 (de)	2007-04-19
MA27065A1 (fr)	2004-12-20
RU2004111803A (ru)	2005-10-10
MY129069A (en)	2007-03-30
MA27066A1 (fr)	2004-12-20

Legal Events

Date	Code	Title	Description
2011-11-04	FB9A	Suspension of patent application procedure

Publication	Publication Date	Title
CZ2004358A3 (cs)	2004-07-14	Spirocyklické-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-on kontrolující zánětlivé cytokiny
PT1465921E (pt)	2006-12-29	Espirocíclico-6, 7-di-idro-5h-pirazolo[1,2-a] pirazol-1-onas que controlam citocinas inflamatórias
AU2002334641A1 (en)	2003-06-05	Spirocyclic-6,7-dihydro-5h-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
AU2002327690A1 (en)	2003-06-05	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
US6730668B2 (en)	2004-05-04	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
US6849627B2 (en)	2005-02-01	6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines
US7326714B2 (en)	2008-02-05	6,7-Dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines