OA11443A - Method for treating COPD. - Google Patents

Method for treating COPD. Download PDF

Info

Publication number: OA11443A
Authority: OA; OAPI
Prior art keywords: cyano; methoxyphenyl; cyclohexane; methyl; cyclopropylmethoxy
Prior art date: 1998-01-07

Application number

OA1200000199A

Other languages

English (en)

Inventor

Theodore Torphy Christensen Iv

Original Assignee

Smithkline Beecham Corp

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.)

1998-01-07

Filing date

2000-07-07

Publication date

2004-04-28

2000-07-07 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

2004-04-28 Publication of OA11443A publication Critical patent/OA11443A/en

Links

238000000034 method Methods 0.000 title claims abstract description 26
-1 1-substituted cyclohexyl group Chemical group 0.000 claims abstract description 187
150000001875 compounds Chemical class 0.000 claims abstract description 54
125000000217 alkyl group Chemical group 0.000 claims description 87
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
229910052739 hydrogen Inorganic materials 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 48
229910052799 carbon Inorganic materials 0.000 claims description 42
229910052760 oxygen Inorganic materials 0.000 claims description 38
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 36
235000019000 fluorine Nutrition 0.000 claims description 35
125000001153 fluoro group Chemical group F* 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 25
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
125000003226 pyrazolyl group Chemical group 0.000 claims description 19
125000001425 triazolyl group Chemical group 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000000335 thiazolyl group Chemical group 0.000 claims description 17
125000000623 heterocyclic group Chemical group 0.000 claims description 16
150000002431 hydrogen Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
125000002883 imidazolyl group Chemical group 0.000 claims description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
125000003831 tetrazolyl group Chemical group 0.000 claims description 13
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 12
125000002971 oxazolyl group Chemical group 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
125000005592 polycycloalkyl group Polymers 0.000 claims description 10
125000000168 pyrrolyl group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000004193 piperazinyl group Chemical group 0.000 claims description 9
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
125000002541 furyl group Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
125000002632 imidazolidinyl group Chemical group 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
125000000160 oxazolidinyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
125000001984 thiazolidinyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 5
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 5
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
CFBUZOUXXHZCFB-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexanecarboxylic acid Chemical compound COC1=CC=C(C2(CCC(CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-UHFFFAOYSA-N 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
239000007983 Tris buffer Substances 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
150000007942 carboxylates Chemical class 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
ZEJDTJNXLFRPTR-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexene-1-carboxylic acid Chemical compound COC1=CC=C(C2(CC=C(CC2)C(O)=O)C#N)C=C1OC1CCCC1 ZEJDTJNXLFRPTR-UHFFFAOYSA-N 0.000 claims description 2
CEBIJCZHGGZIQF-UHFFFAOYSA-N methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexene-1-carboxylate Chemical compound C1CC(C(=O)OC)=CCC1(C#N)C1=CC=C(OC)C(OC2CCCC2)=C1 CEBIJCZHGGZIQF-UHFFFAOYSA-N 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims 3
VDNIBMZRSLBFTM-UHFFFAOYSA-N 1-amino-3-(hexadecylamino)urea Chemical compound C(CCCCCCCCCCCCCCC)NNC(=O)NN VDNIBMZRSLBFTM-UHFFFAOYSA-N 0.000 claims 1
XINOXHGEJZWZEC-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexene-1-carboxylic acid;methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexene-1-carboxylate Chemical compound COC1=CC=C(C2(CC=C(CC2)C(O)=O)C#N)C=C1OC1CCCC1.C1CC(C(=O)OC)=CCC1(C#N)C1=CC=C(OC)C(OC2CCCC2)=C1 XINOXHGEJZWZEC-UHFFFAOYSA-N 0.000 claims 1
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
239000003826 tablet Substances 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
238000009472 formulation Methods 0.000 description 9
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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201000010099 disease Diseases 0.000 description 6
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KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 4
206010006458 Bronchitis chronic Diseases 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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

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Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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OA1200000199A 1998-01-07 2000-07-07 Method for treating COPD. OA11443A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7071898P	1998-01-07	1998-01-07
US10690898P	1998-10-28	1998-10-28

Publications (1)

Publication Number	Publication Date
OA11443A true OA11443A (en)	2004-04-28

Family

ID=26751429

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000199A OA11443A (en)	1998-01-07	2000-07-07	Method for treating COPD.

Country Status (33)

Country	Link
US (1)	US6369108B1 (de)
EP (1)	EP1051172B1 (de)
JP (1)	JP2003522095A (de)
KR (1)	KR100555824B1 (de)
CN (1)	CN1291891A (de)
AP (1)	AP2000001859A0 (de)
AR (1)	AR014411A1 (de)
AT (1)	ATE285234T1 (de)
AU (1)	AU752497B2 (de)
BG (1)	BG104654A (de)
BR (1)	BR9906803A (de)
CA (1)	CA2317720A1 (de)
DE (1)	DE69922786T2 (de)
DZ (1)	DZ2703A1 (de)
EA (1)	EA006382B1 (de)
EG (1)	EG23945A (de)
ES (1)	ES2234234T3 (de)
HU (1)	HUP0100888A3 (de)
ID (1)	ID26164A (de)
IL (1)	IL137104A0 (de)
MA (1)	MA26592A1 (de)
MY (1)	MY133014A (de)
NO (1)	NO20003481L (de)
NZ (1)	NZ505521A (de)
OA (1)	OA11443A (de)
PE (1)	PE20000231A1 (de)
PL (1)	PL341667A1 (de)
PT (1)	PT1051172E (de)
SI (1)	SI1051172T1 (de)
SK (1)	SK285149B6 (de)
TR (1)	TR200001819T2 (de)
UY (1)	UY25338A1 (de)
WO (1)	WO1999034798A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DZ3019A1 (fr)	1999-03-01	2005-05-20	Smithkline Beecham Corp	Utilisation d'un inhibiteur de pde4 dans la préparation d'un médicament contre la copd.
AR024076A1 (es) *	1999-05-25	2002-09-04	Smithkline Beecham Corp	Sales de cis-[4-ciano-4-(3-ciclopentiloxi-4-metoxifenil) ciclohexan-1-carboxilato]
PL353360A1 (en) *	1999-08-10	2003-11-17	Smithkline Beecham Corporation	1,4-substituted 4,4-diaryl cyclohexanes
WO2001043692A2 (en) *	1999-12-15	2001-06-21	Smithkline Beecham Corporation	SALTS OF Cis-4-CYANO-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANE-1-CARBOXYLIC ACID
US6555572B2 (en)	2000-03-16	2003-04-29	Inflazyme Pharmaceuticals Ltd.	Benzylated PDE4 inhibitors
DE10245153A1 (de) *	2002-09-27	2004-04-15	Infineon Technologies Ag	Integrierter Feldeffekttransistor mit zwei Steuerbereichen, Verwendung dieses Feldeffekttranistors und Herstellungsverfahren
JP2008542355A (ja)	2005-05-31	2008-11-27	ファイザー株式会社	Ｖｒ１アンタゴニストとしての置換アリールオキシ−ｎ−ビシクロメチルアセトアミド化合物
CN101679191B (zh) *	2007-06-05	2014-03-12	塞诺菲-安万特股份有限公司	二杂芳基环己烷衍生物、其制备方法、用途及含有它们的药用组合物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0633771A4 (en) *	1992-04-02	1995-02-22	Smithkline Beecham Corporation	Compounds.
CA2133439C (en) *	1992-04-02	2005-07-26	Siegfried Benjamin Christensen, Iv	Compounds useful for treating allergic and inflammatory diseases
GB9525262D0 (en) *	1995-12-11	1996-02-07	Bayer Ag	Heterocyclylcarbonyl substituted benzofuranyl-ureas

1998
- 1998-12-31 UY UY25338A patent/UY25338A1/es not_active Application Discontinuation
1999
- 1999-01-04 MA MA25416A patent/MA26592A1/fr unknown
- 1999-01-05 MY MYPI99000027A patent/MY133014A/en unknown
- 1999-01-06 AU AU21060/99A patent/AU752497B2/en not_active Ceased
- 1999-01-06 SK SK1023-2000A patent/SK285149B6/sk not_active IP Right Cessation
- 1999-01-06 SI SI9930757T patent/SI1051172T1/xx unknown
- 1999-01-06 CN CN99803407A patent/CN1291891A/zh active Pending
- 1999-01-06 NZ NZ505521A patent/NZ505521A/xx unknown
- 1999-01-06 DZ DZ990004A patent/DZ2703A1/xx active
- 1999-01-06 IL IL13710499A patent/IL137104A0/xx not_active IP Right Cessation
- 1999-01-06 ID IDW20001314A patent/ID26164A/id unknown
- 1999-01-06 PL PL99341667A patent/PL341667A1/xx not_active IP Right Cessation
- 1999-01-06 CA CA002317720A patent/CA2317720A1/en not_active Abandoned
- 1999-01-06 US US09/582,739 patent/US6369108B1/en not_active Expired - Fee Related
- 1999-01-06 AT AT99901337T patent/ATE285234T1/de not_active IP Right Cessation
- 1999-01-06 HU HU0100888A patent/HUP0100888A3/hu unknown
- 1999-01-06 EA EA200000740A patent/EA006382B1/ru not_active IP Right Cessation
- 1999-01-06 DE DE69922786T patent/DE69922786T2/de not_active Expired - Fee Related
- 1999-01-06 TR TR2000/01819T patent/TR200001819T2/xx unknown
- 1999-01-06 WO PCT/US1999/000214 patent/WO1999034798A1/en not_active Ceased
- 1999-01-06 PE PE1999000011A patent/PE20000231A1/es not_active Application Discontinuation
- 1999-01-06 BR BR9906803-6A patent/BR9906803A/pt not_active Application Discontinuation
- 1999-01-06 EG EG1499A patent/EG23945A/xx active
- 1999-01-06 ES ES99901337T patent/ES2234234T3/es not_active Expired - Lifetime
- 1999-01-06 AP APAP/P/2000/001859A patent/AP2000001859A0/en unknown
- 1999-01-06 EP EP99901337A patent/EP1051172B1/de not_active Expired - Lifetime
- 1999-01-06 PT PT99901337T patent/PT1051172E/pt unknown
- 1999-01-06 JP JP2000527247A patent/JP2003522095A/ja active Pending
- 1999-01-06 KR KR1020007007487A patent/KR100555824B1/ko not_active Expired - Fee Related
- 1999-01-08 AR ARP990100057A patent/AR014411A1/es unknown
2000
- 2000-07-06 NO NO20003481A patent/NO20003481L/no not_active Application Discontinuation
- 2000-07-07 OA OA1200000199A patent/OA11443A/en unknown
- 2000-08-01 BG BG104654A patent/BG104654A/xx unknown

Also Published As

Publication number	Publication date
HUP0100888A3 (en)	2003-07-28
JP2003522095A (ja)	2003-07-22
PT1051172E (pt)	2005-03-31
EA006382B1 (ru)	2005-12-29
HUP0100888A2 (hu)	2001-08-28
UY25338A1 (es)	2001-08-27
BR9906803A (pt)	2002-05-28
IL137104A0 (en)	2001-06-14
DE69922786T2 (de)	2005-06-23
SK285149B6 (sk)	2006-07-07
DE69922786D1 (de)	2005-01-27
AR014411A1 (es)	2001-02-28
NO20003481D0 (no)	2000-07-06
NZ505521A (en)	2004-02-27
MA26592A1 (fr)	2004-12-20
WO1999034798A1 (en)	1999-07-15
MY133014A (en)	2007-10-31
EP1051172B1 (de)	2004-12-22
EP1051172A2 (de)	2000-11-15
SK10232000A3 (sk)	2001-01-18
EG23945A (en)	2008-01-22
US6369108B1 (en)	2002-04-09
AU752497B2 (en)	2002-09-19
KR100555824B1 (ko)	2006-03-03
DZ2703A1 (fr)	2003-09-01
ATE285234T1 (de)	2005-01-15
BG104654A (en)	2001-04-30
HK1033551A1 (en)	2001-09-07
SI1051172T1 (en)	2005-06-30
PL341667A1 (en)	2001-04-23
CA2317720A1 (en)	1999-07-15
TR200001819T2 (tr)	2000-11-21
KR20010033909A (ko)	2001-04-25
PE20000231A1 (es)	2000-03-24
CN1291891A (zh)	2001-04-18
ID26164A (id)	2000-11-30
EA200000740A1 (ru)	2001-02-26
ES2234234T3 (es)	2005-06-16
EP1051172A4 (de)	2002-08-14
AU2106099A (en)	1999-07-26
NO20003481L (no)	2000-08-25
AP2000001859A0 (en)	2000-09-30

Publication	Publication Date	Title
AP516A (en)	1996-08-23	Pharmaceutical compositions containing novel compounds and their use in treating allergic and inflammatory diseases.
EP0636026A1 (de)	1995-02-01	Verbindungen zur behandlung von entzündlichen erkrankungen und zur hemmung der produktion von tumornekrosefaktor
JPH09501420A (ja)	1997-02-10	３−シアノ−３−（３，４−二置換）フェニルシクロヘキシル−１−カルボキシレート類
AU752497B2 (en)	2002-09-19	Method for treating COPD
JPH09503503A (ja)	1997-04-08	化合物、組成物ならびにアレルギーおよび炎症の治療
HK1033551B (en)	2005-09-16	Method for treating copd
CA2317548A1 (en)	1999-07-15	Method for treating multiple sclerosis
MXPA00006704A (en)	2001-07-03	Method for treating copd
CZ20002530A3 (cs)	2001-06-13	Farmaceutický prostředek, způsob profylaxe, použití pro výrobu léčiva, způsob jeho výroby a léčivo
WO2007007757A1 (ja)	2007-01-18	PPARγアゴニストを含有する医薬組成物
JPH10511391A (ja)	1998-11-04	３，３−（二置換）シクロヘキサン−１−オール二量体および関連化合物
AU3675999A (en)	1999-08-19	A method for treating allergic and inflammatory diseases and for inhibiting the production of tumor necrosis factor
WO2004105751A1 (en)	2004-12-09	Traitement of cardiovascular pathology
SA99191074A (ar)	2005-12-03	Copd طريقة لعلاج
SI9300167A (sl)	1993-12-31	Nove spojine, ki so uporabne pri posredovanju ali inhibiciji encimske aktivnosti fosfodiesteraze IV (PDE IV)
JPH10511388A (ja)	1998-11-04	３，３−（二置換）シクロヘキサン−１−カルボキシレートダイマーおよび関連化合物
HK1063180A (en)	2004-12-17	Compounds useful for treating allergic and inflammatory diseases
HK1022467B (en)	2004-01-09	Compounds useful for treating allergic and inflammatory diseases
JPH10511661A (ja)	1998-11-10	１，３，３−（三置換）シクロヘキサ−１−エン二量体および関連化合物
JPH10511389A (ja)	1998-11-04	４，４−（二置換）シクロヘキサン−１−オール二量体および関連化合物