LU86406A1 - Imidazoquinoleines antithrombogenes cardiotoniques - Google Patents

Imidazoquinoleines antithrombogenes cardiotoniques Download PDF

Info

Publication number: LU86406A1
Authority: LU; Luxembourg
Prior art keywords: imidazo; dihydro; formula; quinoline; compound according
Prior art date: 1985-04-25

Application number

LU86406A

Other languages

English (en)

French (fr)

Original Assignee

Bristol Myers Co

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.)

1985-04-25

Filing date

1986-04-24

Publication date

1986-11-05

1986-04-24 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1986-11-05 Publication of LU86406A1 publication Critical patent/LU86406A1/fr

Links

230000003177 cardiotonic effect Effects 0.000 title description 6
230000002965 anti-thrombogenic effect Effects 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 151
-1 alkoxy radical Chemical class 0.000 claims description 85
238000000034 method Methods 0.000 claims description 72
150000003839 salts Chemical class 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
125000005843 halogen group Chemical group 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 29
210000001772 blood platelet Anatomy 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
150000001469 hydantoins Chemical class 0.000 claims description 19
230000002776 aggregation Effects 0.000 claims description 18
238000004220 aggregation Methods 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 16
230000008569 process Effects 0.000 claims description 16
230000009467 reduction Effects 0.000 claims description 15
238000011282 treatment Methods 0.000 claims description 14
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 13
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229940091173 hydantoin Drugs 0.000 claims description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 9
238000007363 ring formation reaction Methods 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 8
ODCKPUDNMNCWMR-UHFFFAOYSA-N 7,8-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=C(C)C(C)=CC=C21 ODCKPUDNMNCWMR-UHFFFAOYSA-N 0.000 claims description 7
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
210000002216 heart Anatomy 0.000 claims description 6
230000000297 inotrophic effect Effects 0.000 claims description 6
239000007800 oxidant agent Substances 0.000 claims description 6
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230000015572 biosynthetic process Effects 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
229910019142 PO4 Inorganic materials 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
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150000002367 halogens Chemical class 0.000 claims description 4
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
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BSAKVJKPJIQKNP-UHFFFAOYSA-N 7-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(C)=CC=C21 BSAKVJKPJIQKNP-UHFFFAOYSA-N 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
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SWFQYDVZFIVQHW-UHFFFAOYSA-N 1,8-dimethyl-9,9a-dihydro-4h-imidazo[4,5-b]quinolin-2-one Chemical compound C1C2=C(C)C=CC=C2N=C2C1N(C)C(=O)N2 SWFQYDVZFIVQHW-UHFFFAOYSA-N 0.000 claims description 2
VBQVHGPNYUAGFI-UHFFFAOYSA-N 6,7-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2C=C(C)C(C)=CC2=CC2=C1NC(=O)N2 VBQVHGPNYUAGFI-UHFFFAOYSA-N 0.000 claims description 2
CTZIRIUSNWPEKZ-UHFFFAOYSA-N 7-bromo-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(Br)=CC=C21 CTZIRIUSNWPEKZ-UHFFFAOYSA-N 0.000 claims description 2
VZXBGYRONYENIL-UHFFFAOYSA-N 8-chloro-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(Cl)=CC=CC2=NC2=C1NC(=O)N2 VZXBGYRONYENIL-UHFFFAOYSA-N 0.000 claims description 2
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239000008194 pharmaceutical composition Substances 0.000 claims description 2
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AMQUYLNSYUJEKH-UHFFFAOYSA-N 6,7,8-trimethoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(OC)=C(OC)C(OC)=CC2=NC2=C1NC(=O)N2 AMQUYLNSYUJEKH-UHFFFAOYSA-N 0.000 claims 1
OIKKOZDXQORKSP-UHFFFAOYSA-N 6-(trifluoromethyl)-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2NC(=O)NC2=NC2=CC(C(F)(F)F)=CC=C21 OIKKOZDXQORKSP-UHFFFAOYSA-N 0.000 claims 1
YCKKLLYMMVHPIG-UHFFFAOYSA-N 7,8-dimethyl-1,4,9,9a-tetrahydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2CC2=C(C)C(C)=CC=C21 YCKKLLYMMVHPIG-UHFFFAOYSA-N 0.000 claims 1
YEBXOZQMALFMCP-UHFFFAOYSA-N 7-bromo-6,8-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=C(Br)C(C)=CC2=NC2=C1NC(=O)N2 YEBXOZQMALFMCP-UHFFFAOYSA-N 0.000 claims 1
OSBMKBWTTUTUMA-UHFFFAOYSA-N 7-chloro-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(Cl)=CC=C21 OSBMKBWTTUTUMA-UHFFFAOYSA-N 0.000 claims 1
SBMFEGWRZYIWGG-UHFFFAOYSA-N 7-ethoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(OCC)=CC=C21 SBMFEGWRZYIWGG-UHFFFAOYSA-N 0.000 claims 1
XTXHKKBSLRGOJD-UHFFFAOYSA-N 7-fluoro-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(F)=CC=C21 XTXHKKBSLRGOJD-UHFFFAOYSA-N 0.000 claims 1
RXZNLEUDXVTIQC-UHFFFAOYSA-N 7-methoxy-1-methyl-3h-imidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)N(C)C2=CC2=CC(OC)=CC=C21 RXZNLEUDXVTIQC-UHFFFAOYSA-N 0.000 claims 1
FPYRERVDZQWRBO-UHFFFAOYSA-N 7-propan-2-yloxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(OC(C)C)=CC=C21 FPYRERVDZQWRBO-UHFFFAOYSA-N 0.000 claims 1
GMKORAPPNLPTAX-UHFFFAOYSA-N 8-methoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(OC)=CC=CC2=NC2=C1NC(=O)N2 GMKORAPPNLPTAX-UHFFFAOYSA-N 0.000 claims 1
NFWDGDAZJTYAHA-UHFFFAOYSA-N 8-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=CC=CC2=NC2=C1NC(=O)N2 NFWDGDAZJTYAHA-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
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125000003118 aryl group Chemical group 0.000 description 35
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230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
230000010349 pulsation Effects 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
210000001525 retina Anatomy 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
210000005241 right ventricle Anatomy 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000003998 snake venom Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
239000012453 solvate Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical group C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000009424 thromboembolic effect Effects 0.000 description 1
201000005060 thrombophlebitis Diseases 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000007704 transition Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005406 washing Methods 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LU86406A 1985-04-25 1986-04-24 Imidazoquinoleines antithrombogenes cardiotoniques LU86406A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US72686985A	1985-04-25	1985-04-25
US72686985		1985-04-25
US06/832,212 US4668686A (en)	1985-04-25	1986-02-26	Imidazoquinoline antithrombrogenic cardiotonic agents
US83221286		1986-02-26

Publications (1)

Publication Number	Publication Date
LU86406A1 true LU86406A1 (fr)	1986-11-05

Family

ID=27111398

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86406A LU86406A1 (fr)	1985-04-25	1986-04-24	Imidazoquinoleines antithrombogenes cardiotoniques

Country Status (32)

Country	Link
US (1)	US4668686A (da)
KR (1)	KR940000828B1 (da)
CN (1)	CN1016175B (da)
AT (1)	AT390257B (da)
AU (1)	AU592983B2 (da)
BE (1)	BE904671A (da)
CA (1)	CA1298836C (da)
CH (1)	CH675722A5 (da)
CY (1)	CY1641A (da)
DE (1)	DE3614132A1 (da)
DK (3)	DK164868C (da)
EG (1)	EG18104A (da)
ES (3)	ES8708229A1 (da)
FI (1)	FI83316C (da)
FR (1)	FR2581065B1 (da)
GB (1)	GB2174987B (da)
GR (1)	GR861086B (da)
HK (1)	HK64492A (da)
HU (1)	HU195813B (da)
IL (1)	IL78581A0 (da)
IT (1)	IT1215651B (da)
LU (1)	LU86406A1 (da)
MY (1)	MY102086A (da)
NL (1)	NL8601053A (da)
NO (1)	NO163406C (da)
NZ (1)	NZ215885A (da)
OA (1)	OA08242A (da)
PT (1)	PT82460B (da)
SE (1)	SE461468B (da)
SG (1)	SG29092G (da)
SU (3)	SU1450746A3 (da)
YU (1)	YU46054B (da)

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US4701459A (en) *	1986-07-08	1987-10-20	Bristol-Myers Company	7-amino-1,3-dihydro-2H-imidazo[4,5-b]quinolin 2-ones and method for inhibiting phosphodiesterase and blood platelet aggregation
US4743607A (en) *	1987-05-29	1988-05-10	Merrell Dow Pharmaceuticals Inc.	Cardiotonic tricyclic imidazolones
US4803210A (en) *	1987-05-29	1989-02-07	Merrell Dow Pharmaceuticals Inc.	Cardiotonic tricyclic oxazolones
US4943573A (en) *	1989-11-01	1990-07-24	Bristol-Myers Squibb Company	Imidazo[4,5-b]quinolinyloxyalkanoic acid amides with enhanced water solubility
DE4035854C2 (de) *	1990-11-10	1996-10-02	Daimler Benz Ag	Vorrichtung zum Fangen und Ableiten des von einem Fahrzeugrad hochgeschleuderten Spritzwassers
PH31245A (en) *	1991-10-30	1998-06-18	Janssen Pharmaceutica Nv	1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives.
US5208237A (en) *	1992-04-03	1993-05-04	Bristol-Meyers Squibb Company	7-oxypropylsulfonamido-imidazo[4,5-b]quinolin-2-ones
US5196428A (en) *	1992-04-03	1993-03-23	Bristol-Myers Squibb Company	Imidazo[4,5-b]qinolinyl oxy alkyl ureas
US5158958A (en) *	1992-04-03	1992-10-27	Bristol-Myers Squibb Company	Imidazo[4,5-b]quinolinyl oxy alkyl sulfonyl piperidine derivatives
US5348960A (en) *	1992-04-03	1994-09-20	Bristol-Myers Squibb Company	Imidazo[4,5-b]quinolinyl oxy alkyl tetrazolyl piperidine derivatives
US5552267A (en) *	1992-04-03	1996-09-03	The Trustees Of Columbia University In The City Of New York	Solution for prolonged organ preservation
TW593317B (en) *	1993-06-21	2004-06-21	Janssen Pharmaceutica Nv	Positive cardiac inotropic and lusitropic pyrroloquinolinone derivatives
AU695301B2 (en) *	1993-07-06	1998-08-13	Pfizer Inc.	Bicyclic tetrahydro pyrazolopyridines
TW574214B (en) *	1994-06-08	2004-02-01	Pfizer	Corticotropin releasing factor antagonists
US6664264B2 (en) *	2000-12-08	2003-12-16	3M Innovative Properties Company	Thioether substituted imidazoquinolines
MXPA06001669A (es)	2003-08-12	2006-04-28	3M Innovative Properties Co	Compuestos que contienen imidazo-oxima sustituidos.
NZ545412A (en)	2003-08-27	2008-12-24	Coley Pharm Group Inc	Aryloxy and arylalkyleneoxy substituted imidazoquinolines
JP2007504269A (ja)	2003-09-05	2007-03-01	スリーエムイノベイティブプロパティズカンパニー	Ｃｄ５＋ｂ細胞リンパ腫の治療方法
EP1673087B1 (en) *	2003-10-03	2015-05-13	3M Innovative Properties Company	Alkoxy substituted imidazoquinolines
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
CN1906192A (zh) *	2003-11-14	2007-01-31	3M创新有限公司	羟胺取代的咪唑环化合物
WO2005048933A2 (en)	2003-11-14	2005-06-02	3M Innovative Properties Company	Oxime substituted imidazo ring compounds
AU2004293078B2 (en)	2003-11-25	2012-01-19	3M Innovative Properties Company	Substituted imidazo ring systems and methods
JP2007517035A (ja)	2003-12-29	2007-06-28	スリーエムイノベイティブプロパティズカンパニー	アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン
EP1699788A2 (en)	2003-12-30	2006-09-13	3M Innovative Properties Company	Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides
US8697873B2 (en)	2004-03-24	2014-04-15	3M Innovative Properties Company	Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
US8017779B2 (en)	2004-06-15	2011-09-13	3M Innovative Properties Company	Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
WO2006009826A1 (en)	2004-06-18	2006-01-26	3M Innovative Properties Company	Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
WO2006038923A2 (en)	2004-06-18	2006-04-13	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
US7915281B2 (en)	2004-06-18	2011-03-29	3M Innovative Properties Company	Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method
CN101056877B (zh) *	2004-09-14	2010-06-09	诺华疫苗和诊断公司	咪唑并喹啉化合物
JP5313502B2 (ja)	2004-12-30	2013-10-09	スリーエムイノベイティブプロパティズカンパニー	置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物
CA2592904C (en)	2004-12-30	2015-04-07	3M Innovative Properties Company	Chiral fused [1,2]imidazo[4,5-c] ring compounds
JP2008530022A (ja)	2005-02-04	2008-08-07	コーリーファーマシューティカルグループ，インコーポレイテッド	免疫反応調節物質を含む水性ゲル処方物
EP1846405A2 (en)	2005-02-11	2007-10-24	3M Innovative Properties Company	Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods
CA2602683A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	Pyrazolopyridine-1,4-diamines and analogs thereof
CA2602590A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
WO2008008432A2 (en)	2006-07-12	2008-01-17	Coley Pharmaceutical Group, Inc.	Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods
US8227603B2 (en)	2006-08-01	2012-07-24	Cytokinetics, Inc.	Modulating skeletal muscle
US8299248B2 (en)	2006-08-02	2012-10-30	Cytokinetics, Incorporated	Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use
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EP2139478A4 (en) *	2007-03-30	2010-05-05	Cytokinetics Inc	CHEMICAL ENTITIES, COMPOSITIONS AND METHODS
US10272082B2 (en)	2011-07-13	2019-04-30	Cytokinetics, Inc.	Combination ALS therapy
WO2024149378A1 (zh) *	2023-01-13	2024-07-18	上海超阳药业有限公司	喹啉酮化合物和萘啶酮化合物及其用途

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US3932407A (en) *	1973-11-19	1976-01-13	Bristol-Myers Company	Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones

1986
- 1986-02-26 US US06/832,212 patent/US4668686A/en not_active Expired - Fee Related
- 1986-03-26 CA CA000505136A patent/CA1298836C/en not_active Expired - Fee Related
- 1986-04-18 NZ NZ215885A patent/NZ215885A/xx unknown
- 1986-04-21 AU AU56413/86A patent/AU592983B2/en not_active Ceased
- 1986-04-22 FI FI861684A patent/FI83316C/fi not_active IP Right Cessation
- 1986-04-22 IL IL78581A patent/IL78581A0/xx not_active IP Right Cessation
- 1986-04-23 CN CN86102747A patent/CN1016175B/zh not_active Expired
- 1986-04-23 EG EG237/86A patent/EG18104A/xx active
- 1986-04-24 BE BE0/216585A patent/BE904671A/fr not_active IP Right Cessation
- 1986-04-24 IT IT8620206A patent/IT1215651B/it active
- 1986-04-24 SU SU864027355A patent/SU1450746A3/ru active
- 1986-04-24 GB GB8610037A patent/GB2174987B/en not_active Expired
- 1986-04-24 ES ES554336A patent/ES8708229A1/es not_active Expired
- 1986-04-24 PT PT82460A patent/PT82460B/pt not_active IP Right Cessation
- 1986-04-24 NL NL8601053A patent/NL8601053A/xx not_active Application Discontinuation
- 1986-04-24 NO NO861617A patent/NO163406C/no unknown
- 1986-04-24 CH CH1679/86A patent/CH675722A5/de not_active IP Right Cessation
- 1986-04-24 GR GR861086A patent/GR861086B/el unknown
- 1986-04-24 DK DK190986A patent/DK164868C/da not_active IP Right Cessation
- 1986-04-24 SE SE8601907A patent/SE461468B/sv not_active IP Right Cessation
- 1986-04-24 FR FR868605966A patent/FR2581065B1/fr not_active Expired - Fee Related
- 1986-04-24 LU LU86406A patent/LU86406A1/fr unknown
- 1986-04-25 KR KR1019860003204A patent/KR940000828B1/ko not_active Expired - Lifetime
- 1986-04-25 OA OA58845A patent/OA08242A/xx unknown
- 1986-04-25 HU HU861723A patent/HU195813B/hu not_active IP Right Cessation
- 1986-04-25 AT AT0112186A patent/AT390257B/de not_active IP Right Cessation
- 1986-04-25 DE DE19863614132 patent/DE3614132A1/de not_active Ceased
1987
- 1987-02-27 SU SU874202071A patent/SU1470192A3/ru active
- 1987-05-14 ES ES557552A patent/ES8802521A1/es not_active Expired
- 1987-05-14 ES ES557551A patent/ES8801829A1/es not_active Expired
- 1987-06-23 YU YU116787A patent/YU46054B/sh unknown
- 1987-09-25 SU SU874203391A patent/SU1560056A3/ru active
- 1987-09-29 MY MYPI87002266A patent/MY102086A/en unknown
1991
- 1991-04-30 DK DK080291A patent/DK165248C/da not_active IP Right Cessation
- 1991-05-01 DK DK081091A patent/DK165249C/da not_active IP Right Cessation
1992
- 1992-03-10 SG SG290/92A patent/SG29092G/en unknown
- 1992-08-27 HK HK644/92A patent/HK64492A/xx unknown
- 1992-11-06 CY CY1641A patent/CY1641A/en unknown

Also Published As

Publication number	Publication date
FI861684A0 (fi)	1986-04-22
FI83316B (fi)	1991-03-15
DK80291A (da)	1991-04-30
PT82460B (pt)	1988-11-30
ES554336A0 (es)	1987-10-01
BE904671A (fr)	1986-10-24
DK165248C (da)	1993-03-22
DK81091A (da)	1991-05-01
DK165248B (da)	1992-10-26
YU116787A (en)	1988-04-30
FI83316C (fi)	1991-06-25
AU592983B2 (en)	1990-02-01
EG18104A (en)	1992-09-30
DK190986A (da)	1986-10-26
ES8801829A1 (es)	1988-02-16
NZ215885A (en)	1989-04-26
AU5641386A (en)	1986-10-30
KR860008177A (ko)	1986-11-12
CN1016175B (zh)	1992-04-08
SG29092G (en)	1992-05-15
GR861086B (en)	1986-09-01
MY102086A (en)	1992-03-31
ES8802521A1 (es)	1988-07-16
IT1215651B (it)	1990-02-22
SE461468B (sv)	1990-02-19
SU1450746A3 (ru)	1989-01-07
FR2581065A1 (fr)	1986-10-31
OA08242A (en)	1987-10-30
DK80291D0 (da)	1991-04-30
NL8601053A (nl)	1986-11-17
FR2581065B1 (fr)	1990-02-02
IL78581A0 (en)	1986-08-31
AT390257B (de)	1990-04-10
CN86102747A (zh)	1987-02-04
SE8601907L (sv)	1986-10-26
YU46054B (sh)	1992-12-21
DK190986D0 (da)	1986-04-24
CY1641A (en)	1992-11-06
ES557552A0 (es)	1988-07-16
DK165249C (da)	1993-03-22
GB8610037D0 (en)	1986-05-29
PT82460A (en)	1986-05-01
HK64492A (en)	1992-09-04
HU195813B (en)	1988-07-28
DK164868B (da)	1992-08-31
FI861684L (fi)	1986-10-26
US4668686A (en)	1987-05-26
ATA112186A (de)	1989-09-15
ES8708229A1 (es)	1987-10-01
SE8601907D0 (sv)	1986-04-24
SU1560056A3 (ru)	1990-04-23
IT8620206A0 (it)	1986-04-24
CA1298836C (en)	1992-04-14
CH675722A5 (da)	1990-10-31
NO163406C (no)	1990-05-23
NO861617L (no)	1986-10-27
HUT42089A (en)	1987-06-29
DE3614132A1 (de)	1986-11-27
DK81091D0 (da)	1991-05-01
DK164868C (da)	1993-01-11
ES557551A0 (es)	1988-02-16
KR940000828B1 (ko)	1994-02-02
NO163406B (no)	1990-02-12
SU1470192A3 (ru)	1989-03-30
DK165249B (da)	1992-10-26
GB2174987A (en)	1986-11-19
GB2174987B (en)	1989-08-02

Publication	Publication Date	Title
US4668686A (en)	1987-05-26	Imidazoquinoline antithrombrogenic cardiotonic agents
US11001563B2 (en)	2021-05-11	SSAO inhibitor
JP4634037B2 (ja)	2011-02-16	キサンチンオキシダーゼ阻害剤
EP0202164B1 (fr)	1989-02-08	Dérivés de (benzoyl-4 pipéridino)-2 phenyl-1 alcanols, leur préparation et leur application en thérapeutique
EP0031741A1 (fr)	1981-07-08	Nouveaux iminoacides substitués, leurs procédés de préparation et leur emploi comme inhibiteurs d'enzymes
EP0281459A1 (fr)	1988-09-07	Enantiomère dextrogyre de l'alpha-(tétrahydro-4,5,6,7 thiéno (3,2-c)pyridyl-5) (chloro-2 phényl)-acétate de méthyle, son procédé de préparation et les compositions pharmaceutiques le renfermant
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EP0300676A2 (en)	1989-01-25	Tetrahydrocarbazole 1-alkanoic acids
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