NO300592B1 - Imidazopyridin PAF/H1 antagonister - Google Patents

Imidazopyridin PAF/H1 antagonister Download PDF

Info

Publication number: NO300592B1
Authority: NO; Norway
Prior art keywords: pyrid; methylimidazo; ylidene; piperidine; dihydro
Prior art date: 1991-02-13

Application number

NO932889A

Other languages

English (en)

Norwegian (no)

Other versions

NO932889D0 (no

NO932889L (no

Inventor

David Alker

Robert John Bass

Kelvin Cooper

Original Assignee

Pfizer

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.)

1991-02-13

Filing date

1993-08-13

Publication date

1997-06-23

1993-08-13 Application filed by Pfizer filed Critical Pfizer

1993-08-13 Publication of NO932889D0 publication Critical patent/NO932889D0/no

1993-08-13 Publication of NO932889L publication Critical patent/NO932889L/no

1997-06-23 Publication of NO300592B1 publication Critical patent/NO300592B1/no

Links

239000005557 antagonist Substances 0.000 title description 10
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150000002367 halogens Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
JCXPGABLLNGRLW-UHFFFAOYSA-N [4-(8-chloro-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridin-11-ylidene)piperidin-1-yl]-[4-(2-methylimidazo[4,5-c]pyridin-1-yl)phenyl]methanone Chemical group C12=CC=C(Cl)C=C2CCC2=CC=CN=C2C1=C(CC1)CCN1C(=O)C(C=C1)=CC=C1N1C2=CC=NC=C2N=C1C JCXPGABLLNGRLW-UHFFFAOYSA-N 0.000 claims description 2
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IJSNBIZGINRLAA-UHFFFAOYSA-N 5-(2-methylimidazo[4,5-c]pyridin-1-yl)thiophene-2-carboxylic acid Chemical compound CC1=NC2=CN=CC=C2N1C1=CC=C(C(O)=O)S1 IJSNBIZGINRLAA-UHFFFAOYSA-N 0.000 description 1
WMORVPINIPZYHR-UHFFFAOYSA-N 5-[(3-aminopyridin-4-yl)amino]thiophene-2-carbonitrile Chemical compound NC1=CN=CC=C1NC1=CC=C(C#N)S1 WMORVPINIPZYHR-UHFFFAOYSA-N 0.000 description 1
MVTAUCKEBQDFMV-UHFFFAOYSA-N 5-[(3-nitropyridin-4-yl)amino]thiophene-2-carbonitrile Chemical compound [O-][N+](=O)C1=CN=CC=C1NC1=CC=C(C#N)S1 MVTAUCKEBQDFMV-UHFFFAOYSA-N 0.000 description 1
GISCGLDZXOXKBZ-UHFFFAOYSA-N 5-aminothiophene-2-carbonitrile Chemical compound NC1=CC=C(C#N)S1 GISCGLDZXOXKBZ-UHFFFAOYSA-N 0.000 description 1
FLYONFCGDKAMIH-UHFFFAOYSA-N 5-nitrothiophene-2-carbonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)S1 FLYONFCGDKAMIH-UHFFFAOYSA-N 0.000 description 1
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JHGVQPKEQPYPCI-UHFFFAOYSA-N 8-chloro-11-[1-[4-(2-methylimidazo[4,5-c]pyridin-1-yl)benzoyl]piperidin-4-ylidene]-6h-benzo[1,2]cyclohepta[2,4-b]pyridin-5-one Chemical compound C12=CC=C(Cl)C=C2CC(=O)C2=CC=CN=C2C1=C(CC1)CCN1C(=O)C(C=C1)=CC=C1N1C2=CC=NC=C2N=C1C JHGVQPKEQPYPCI-UHFFFAOYSA-N 0.000 description 1
VHAKXBCKHLPQOR-UHFFFAOYSA-N 8-chloro-11-piperidin-4-ylidene-6h-benzo[1,2]cyclohepta[2,4-b]pyridin-5-one Chemical compound C=1C(Cl)=CC=C2C=1CC(=O)C1=CC=CN=C1C2=C1CCNCC1 VHAKXBCKHLPQOR-UHFFFAOYSA-N 0.000 description 1
DSDQPELJDBELOW-UHFFFAOYSA-N 8-chloro-11-piperidin-4-ylidenebenzo[1,2]cyclohepta[2,4-b]pyridine Chemical compound C=1C(Cl)=CC=C2C=1C=CC1=CC=CN=C1C2=C1CCNCC1 DSDQPELJDBELOW-UHFFFAOYSA-N 0.000 description 1
LIJHTMPYIGYTHQ-UHFFFAOYSA-N 8-methyl-11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine Chemical compound C=1C(C)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 LIJHTMPYIGYTHQ-UHFFFAOYSA-N 0.000 description 1
206010049153 Allergic sinusitis Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
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239000006286 aqueous extract Substances 0.000 description 1
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WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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230000010083 bronchial hyperresponsiveness Effects 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
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230000001684 chronic effect Effects 0.000 description 1
238000004040 coloring Methods 0.000 description 1
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238000009109 curative therapy Methods 0.000 description 1
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229910000071 diazene Inorganic materials 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
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CFNDVXUTYPXOPG-UHFFFAOYSA-N ethyl 2-(4-aminophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(N)C=C1 CFNDVXUTYPXOPG-UHFFFAOYSA-N 0.000 description 1
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JVMFWRZQIXYGOX-UHFFFAOYSA-N ethyl 2-[(3-nitropyridin-4-yl)amino]benzoate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC=CC=C1NC1=CC=NC=C1[N+]([O-])=O JVMFWRZQIXYGOX-UHFFFAOYSA-N 0.000 description 1
BYDGUAYFWGWVRB-UHFFFAOYSA-N ethyl 2-[4-[(3-nitropyridin-4-yl)amino]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1NC1=CC=NC=C1[N+]([O-])=O BYDGUAYFWGWVRB-UHFFFAOYSA-N 0.000 description 1
LIPJHHSOXXLKAF-UHFFFAOYSA-N ethyl 3-(2-methylimidazo[4,5-c]pyridin-1-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(N2C3=CC=NC=C3N=C2C)=C1 LIPJHHSOXXLKAF-UHFFFAOYSA-N 0.000 description 1
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238000002474 experimental method Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000000938 histamine H1 antagonist Substances 0.000 description 1
229960004931 histamine dihydrochloride Drugs 0.000 description 1
PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000004047 hyperresponsiveness Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000005232 imidazopyridines Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
230000004941 influx Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000004796 pathophysiological change Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
238000000053 physical method Methods 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000007112 pro inflammatory response Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
206010041232 sneezing Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003892 tartrate salts Chemical class 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
238000004809 thin layer chromatography Methods 0.000 description 1
239000003848 thrombocyte activating factor antagonist Substances 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
230000009466 transformation Effects 0.000 description 1
ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- 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
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
Immunology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Prostheses (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cosmetics (AREA)
Steroid Compounds (AREA)

NO932889A 1991-02-13 1993-08-13 Imidazopyridin PAF/H1 antagonister NO300592B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB919102997A GB9102997D0 (en)	1991-02-13	1991-02-13	Therapeutic agents
PCT/EP1992/000163 WO1992014734A1 (en)	1991-02-13	1992-01-24	Imidazopyridine paf/h1 antagonists

Publications (3)

Publication Number	Publication Date
NO932889D0 NO932889D0 (no)	1993-08-13
NO932889L NO932889L (no)	1993-08-13
NO300592B1 true NO300592B1 (no)	1997-06-23

Family

ID=10689943

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO932889A NO300592B1 (no)	1991-02-13	1993-08-13	Imidazopyridin PAF/H1 antagonister

Country Status (29)

Country	Link
US (1)	US5358953A (zh)
EP (1)	EP0572425B1 (zh)
JP (1)	JP2506541B2 (zh)
KR (1)	KR970005302B1 (zh)
CN (1)	CN1040326C (zh)
AT (1)	ATE109482T1 (zh)
AU (1)	AU650322B2 (zh)
BR (1)	BR9205615A (zh)
CA (1)	CA2099381C (zh)
CZ (1)	CZ280504B6 (zh)
DE (1)	DE69200304T2 (zh)
DK (1)	DK0572425T3 (zh)
EG (1)	EG20085A (zh)
ES (1)	ES2059212T3 (zh)
FI (1)	FI933531A (zh)
GB (1)	GB9102997D0 (zh)
HU (2)	HUT65947A (zh)
IE (1)	IE65125B1 (zh)
IL (1)	IL100887A (zh)
MX (1)	MX9200589A (zh)
MY (1)	MY108437A (zh)
NO (1)	NO300592B1 (zh)
NZ (1)	NZ241597A (zh)
PL (1)	PL169304B1 (zh)
RU (1)	RU2114845C1 (zh)
TW (1)	TW227000B (zh)
WO (1)	WO1992014734A1 (zh)
YU (1)	YU48238B (zh)
ZA (1)	ZA921005B (zh)

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ES2042421B1 (es) *	1992-05-22	1994-08-01	Uriach & Cia Sa J	Procedimiento para la obtencion de la 8-cloro-11-1-(5-metil-3-piridil)metil-4-piperidiliden-6,11-dihidro-5h-benzo5,6ciclohepta1,2-bpiridina.
AU3186395A (en) *	1994-08-10	1996-03-07	British Biotech Pharmaceuticals Limited	Imidazopyridine derivatives as dual histamine (h1) and platelet activating factor (paf) antagonists
ES2087038B1 (es) *	1994-11-07	1997-03-16	Uriach & Cia Sa J	Nuevas piperidinas con actividad antagonista del paf.
US5567711A (en) *	1995-04-19	1996-10-22	Abbott Laboratories	Indole-3-carbonyl and indole-3-sulfonyl derivatives as platelet activating factor antagonists
GB9508748D0 (en) *	1995-04-28	1995-06-14	British Biotech Pharm	Benzimidazole derivatives
GB2308593B (en) *	1995-08-05	1999-01-27	British Biotech Pharm	Imidazopyridine derivatives
CA2417960C (en)	2000-08-04	2012-07-10	Dmi Biosciences, Inc.	Method of using diketopiperazines and composition containing them
CN102210852B (zh)	2003-05-15	2016-10-19	安皮奥制药股份有限公司	T-细胞介导的疾病的治疗
US7687515B2 (en) *	2006-01-17	2010-03-30	N.V. Organon	6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives
US8377967B2 (en)	2008-01-30	2013-02-19	Nippon Zoki Pharmaceutical Co., Ltd.	Piperidine derivative
EP2300011A4 (en)	2008-05-27	2012-06-20	Dmi Life Sciences Inc	METHODS AND THERAPEUTIC COMPOUNDS
CN103619839B (zh) *	2011-06-28	2016-06-01	福建省闽东力捷迅药业有限公司	抗-***反应的苯并环庚并噻吩衍生物
MY167804A (en)	2011-10-10	2018-09-26	Ampio Pharmaceuticals Inc	Treatment of degenerative joint disease
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1991
- 1991-02-13 GB GB919102997A patent/GB9102997D0/en active Pending
1992
- 1992-01-24 HU HU9302327A patent/HUT65947A/hu unknown
- 1992-01-24 CA CA002099381A patent/CA2099381C/en not_active Expired - Fee Related
- 1992-01-24 JP JP4503504A patent/JP2506541B2/ja not_active Expired - Fee Related
- 1992-01-24 DK DK92902889.2T patent/DK0572425T3/da active
- 1992-01-24 ES ES92902889T patent/ES2059212T3/es not_active Expired - Lifetime
- 1992-01-24 WO PCT/EP1992/000163 patent/WO1992014734A1/en active IP Right Grant
- 1992-01-24 PL PL92300296A patent/PL169304B1/pl unknown
- 1992-01-24 RU RU93054165A patent/RU2114845C1/ru active
- 1992-01-24 AU AU11683/92A patent/AU650322B2/en not_active Ceased
- 1992-01-24 AT AT92902889T patent/ATE109482T1/de not_active IP Right Cessation
- 1992-01-24 EP EP92902889A patent/EP0572425B1/en not_active Expired - Lifetime
- 1992-01-24 BR BR9205615A patent/BR9205615A/pt not_active Application Discontinuation
- 1992-01-24 DE DE69200304T patent/DE69200304T2/de not_active Expired - Fee Related
- 1992-01-24 KR KR1019930702352A patent/KR970005302B1/ko not_active IP Right Cessation
- 1992-01-24 US US08/087,736 patent/US5358953A/en not_active Expired - Fee Related
- 1992-02-06 IL IL10088792A patent/IL100887A/en not_active IP Right Cessation
- 1992-02-10 EG EG8792A patent/EG20085A/xx active
- 1992-02-10 TW TW081100891A patent/TW227000B/zh active
- 1992-02-11 MX MX9200589A patent/MX9200589A/es unknown
- 1992-02-12 IE IE920449A patent/IE65125B1/en not_active IP Right Cessation
- 1992-02-12 YU YU14392A patent/YU48238B/sh unknown
- 1992-02-12 CZ CS92425A patent/CZ280504B6/cs not_active IP Right Cessation
- 1992-02-12 ZA ZA921005A patent/ZA921005B/xx unknown
- 1992-02-12 MY MYPI92000223A patent/MY108437A/en unknown
- 1992-02-12 NZ NZ241597A patent/NZ241597A/en unknown
- 1992-02-13 CN CN92100974A patent/CN1040326C/zh not_active Expired - Fee Related
1993
- 1993-08-10 FI FI933531A patent/FI933531A/fi not_active Application Discontinuation
- 1993-08-13 NO NO932889A patent/NO300592B1/no unknown
1995
- 1995-06-09 HU HU95P/P00175P patent/HU211202A9/hu unknown

Also Published As

Publication number	Publication date
RU2114845C1 (ru)	1998-07-10
NZ241597A (en)	1993-04-28
CN1040326C (zh)	1998-10-21
HU9302327D0 (en)	1993-10-28
AU1168392A (en)	1992-09-15
IL100887A0 (en)	1992-11-15
HUT65947A (en)	1994-08-29
AU650322B2 (en)	1994-06-16
IE65125B1 (en)	1995-10-04
NO932889D0 (no)	1993-08-13
CA2099381A1 (en)	1992-08-14
JPH06504992A (ja)	1994-06-09
YU14392A (sh)	1994-11-15
DK0572425T3 (da)	1994-09-12
NO932889L (no)	1993-08-13
CS42592A3 (en)	1992-09-16
CZ280504B6 (cs)	1996-02-14
ZA921005B (en)	1993-08-12
FI933531A0 (fi)	1993-08-10
DE69200304T2 (de)	1994-12-08
MY108437A (en)	1996-09-30
TW227000B (zh)	1994-07-21
GB9102997D0 (en)	1991-03-27
WO1992014734A1 (en)	1992-09-03
HU211202A9 (en)	1995-11-28
MX9200589A (es)	1992-10-01
IL100887A (en)	1996-01-19
DE69200304D1 (de)	1994-09-08
JP2506541B2 (ja)	1996-06-12
IE920449A1 (en)	1992-08-12
BR9205615A (pt)	1994-05-17
CA2099381C (en)	1996-07-09
FI933531A (fi)	1993-08-10
YU48238B (sh)	1997-08-22
ES2059212T3 (es)	1994-11-01
EP0572425B1 (en)	1994-08-03
EG20085A (en)	1997-05-31
US5358953A (en)	1994-10-25
KR970005302B1 (ko)	1997-04-15
CN1064275A (zh)	1992-09-09
ATE109482T1 (de)	1994-08-15
EP0572425A1 (en)	1993-12-08
PL169304B1 (pl)	1996-06-28

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JPH0678315B2 (ja)	1994-10-05	新規なベンゾピリド‐ピペリジン、ピペリジリデンおよびピペラジン化合物、組成物、製造法および利用法
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US5250531A (en)	1993-10-05	Dihydropyrimidine antiallergy agents
JP2003527426A (ja)	2003-09-16	トロンビン阻害薬
AU2006201994A1 (en)	2006-11-30	New phenylpyridinylpiperazine compounds, a process for their preparation and pharmaceutical compositions containing them
JPH07505394A (ja)	1995-06-15	橋渡しビスアリールカルビノール誘導体，組成物および使用法
US4192944A (en)	1980-03-11	Optionally substituted 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-N-(1H-tetrazol-4-yl)carboxamides and their use as antiallergy agents
US5438062A (en)	1995-08-01	Benzo(5,6)cycloheptapyridines, compositions and methods of use
FI101225B (fi)	1998-05-15	Menetelmä terapeuttisesti käyttökelpoisten 2-metyyli-imidatso£4,5-c\|py rid-1-yylijohdannaisten valmistamiseksi
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US5665726A (en)	1997-09-09	Benzo[5,6]cycloheptapyridines, compositions and methods of use
JPH064637B2 (ja)	1994-01-19	新規なインドール誘導体
JPH05507932A (ja)	1993-11-11	イミダゾピリジンｐａｆ拮抗薬
JPH11503130A (ja)	1999-03-23	新規方法
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