LT3447B - Positive inotropic and lusitropic pyrroloquinolinone derivatives, method for preparing thereof, pharmaceutical composition and method for preparing the same - Google Patents
Positive inotropic and lusitropic pyrroloquinolinone derivatives, method for preparing thereof, pharmaceutical composition and method for preparing the same Download PDFInfo
- Publication number
- LT3447B LT3447B LTIP1960A LTIP1960A LT3447B LT 3447 B LT3447 B LT 3447B LT IP1960 A LTIP1960 A LT IP1960A LT IP1960 A LTIP1960 A LT IP1960A LT 3447 B LT3447 B LT 3447B
- Authority
- LT
- Lithuania
- Prior art keywords
- formula
- compound
- compounds
- optionally substituted
- quinolin
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 230000000297 inotrophic effect Effects 0.000 title abstract description 8
- 230000003295 lusitropic effect Effects 0.000 title abstract 2
- WUKKREVJKMPFTB-UHFFFAOYSA-N pyrrolo[2,3-h]quinolin-2-one Chemical class C1=C2N=CC=C2C2=NC(=O)C=CC2=C1 WUKKREVJKMPFTB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- -1 (cyclopentyloxy) (methoxy) Chemical class 0.000 claims description 30
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 3
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- 238000005886 esterification reaction Methods 0.000 description 1
- SRBWSIYACQAFHD-UHFFFAOYSA-N ethanol piperazine dihydrochloride Chemical compound Cl.Cl.CCO.C1CNCCN1 SRBWSIYACQAFHD-UHFFFAOYSA-N 0.000 description 1
- LURMKUCOMFPPCZ-UHFFFAOYSA-N ethyl 5-(3-formyl-4-nitrophenoxy)pentanoate Chemical compound CCOC(=O)CCCCOC1=CC=C([N+]([O-])=O)C(C=O)=C1 LURMKUCOMFPPCZ-UHFFFAOYSA-N 0.000 description 1
- QSHAHYDERDRJDQ-UKTHLTGXSA-N ethyl 5-[3-[(e)-(2,5-dioxopyrrolidin-3-ylidene)methyl]-4-nitrophenoxy]pentanoate Chemical compound CCOC(=O)CCCCOC1=CC=C([N+]([O-])=O)C(\C=C/2C(NC(=O)C\2)=O)=C1 QSHAHYDERDRJDQ-UKTHLTGXSA-N 0.000 description 1
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- 230000002140 halogenating effect Effects 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
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- 235000011167 hydrochloric acid Nutrition 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
- HOPZBJPSUKPLDT-UHFFFAOYSA-N imidazo[4,5-h]quinolin-2-one Chemical class C1=CN=C2C3=NC(=O)N=C3C=CC2=C1 HOPZBJPSUKPLDT-UHFFFAOYSA-N 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
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- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IMYHGORQCPYVBZ-UHFFFAOYSA-N lofentanyl Chemical group C1CN(CCC=2C=CC=CC=2)CC(C)C1(C(=O)OC)N(C(=O)CC)C1=CC=CC=C1 IMYHGORQCPYVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 150000004885 piperazines Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000000518 sarcolemma Anatomy 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 208000023577 vascular insufficiency disease Diseases 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93201771 | 1993-06-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1960A LTIP1960A (en) | 1995-01-31 |
| LT3447B true LT3447B (en) | 1995-10-25 |
Family
ID=8213908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1960A LT3447B (en) | 1993-06-21 | 1994-06-17 | Positive inotropic and lusitropic pyrroloquinolinone derivatives, method for preparing thereof, pharmaceutical composition and method for preparing the same |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5602134A (cs) |
| EP (1) | EP0707586B1 (cs) |
| JP (1) | JP2812804B2 (cs) |
| KR (1) | KR0181560B1 (cs) |
| CN (1) | CN1043765C (cs) |
| AT (1) | ATE171179T1 (cs) |
| AU (1) | AU679077B2 (cs) |
| BG (1) | BG62171B1 (cs) |
| BR (1) | BR9406899A (cs) |
| CA (1) | CA2163122C (cs) |
| CZ (1) | CZ284350B6 (cs) |
| DE (1) | DE69413398T2 (cs) |
| FI (1) | FI109124B (cs) |
| HU (1) | HU220670B1 (cs) |
| IL (1) | IL110055A (cs) |
| LT (1) | LT3447B (cs) |
| LV (1) | LV11545B (cs) |
| MY (1) | MY110751A (cs) |
| NO (1) | NO305366B1 (cs) |
| OA (1) | OA10202A (cs) |
| PH (1) | PH31308A (cs) |
| PL (1) | PL176783B1 (cs) |
| RU (1) | RU2129554C1 (cs) |
| SG (1) | SG49717A1 (cs) |
| SI (1) | SI9420041A (cs) |
| SK (1) | SK280400B6 (cs) |
| TW (1) | TW593317B (cs) |
| WO (1) | WO1995000512A1 (cs) |
| ZA (1) | ZA944382B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA72611C2 (uk) * | 2000-05-17 | 2005-03-15 | Орто-Макнейл Фармацевтикал, Інк. | Похідні заміщеного піролопіридинону, корисні як інгібітори фосфодіестерази |
| US7208497B2 (en) | 2001-07-02 | 2007-04-24 | Novo Nordisk A/S | Substituted piperazines and diazepanes |
| US20030186963A1 (en) | 2001-09-14 | 2003-10-02 | Dorwald Florencio Zaragoza | Substituted piperidines |
| DE60234616D1 (de) * | 2001-09-14 | 2010-01-14 | High Point Pharmaceuticals Llc | Substituierte piperidinen mit selektiver bindungsfähigkeit zu histamin h3-rezeptoren |
| GB0522715D0 (en) * | 2005-11-08 | 2005-12-14 | Helperby Therapeutics Ltd | New use |
| TWI498115B (zh) * | 2007-12-27 | 2015-09-01 | Daiichi Sankyo Co Ltd | 咪唑羰基化合物 |
| GB0808953D0 (en) * | 2008-05-16 | 2008-06-25 | Shire Llc | substituted quinazolines |
| GB0808944D0 (en) * | 2008-05-16 | 2008-06-25 | Shire Llc | Substituted quinazolines |
| RU2457208C2 (ru) * | 2009-07-06 | 2012-07-27 | Государственное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия Федерального агентства по здравоохранению и социальному развитию" (ГОУ ВПО "ПГФА Росздрава") | 1H-ПИРРОЛО[3,4-b]ХИНОЛИН-3,9(2H,4H)-ДИОНЫ, ОБЛАДАЮЩИЕ ПРОТИВОТУБЕРКУЛЕЗНОЙ АКТИВНОСТЬЮ, И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| CN120265631A (zh) * | 2023-01-13 | 2025-07-04 | 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2190676B (en) | 1986-05-23 | 1990-05-30 | Bristol Myers Co | Imidazoquinolinylether derivatives |
| EP0406958A2 (en) | 1989-07-07 | 1991-01-09 | Janssen Pharmaceutica N.V. | Positive inotropic and lusitropic 3,5-dihydroimidazo[2,1-b]quinazolin-2(1H)-one derivatives |
| EP0426180A2 (en) | 1989-11-01 | 1991-05-08 | Bristol-Myers Squibb Company | Imidazo[4,5-b] quinolinyloxyalkanoic acid amides with enhanced water solubility |
| US5196428A (en) | 1992-04-03 | 1993-03-23 | Bristol-Myers Squibb Company | Imidazo[4,5-b]qinolinyl oxy alkyl ureas |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4552884A (en) * | 1984-01-13 | 1985-11-12 | The Boots Company Plc | Method of treating heart disease |
| US4668686A (en) * | 1985-04-25 | 1987-05-26 | Bristol-Myers Company | Imidazoquinoline antithrombrogenic cardiotonic agents |
| SU1527588A1 (ru) * | 1987-01-16 | 1989-12-07 | Саратовский государственный медицинский институт | Способ определени аллергических реакций на лекарственный препарат |
| CN1030196C (zh) * | 1989-07-07 | 1995-11-01 | 詹森药业有限公司 | 增强收缩力和舒张力的-二氢咪唑并喹唑啉酮衍生物的制备方法 |
| US5220023A (en) * | 1989-07-18 | 1993-06-15 | Janssen Pharmaceutica N.V. | Glycine derivatives |
-
1994
- 1994-05-30 TW TW083104889A patent/TW593317B/zh not_active IP Right Cessation
- 1994-06-10 PH PH48424A patent/PH31308A/en unknown
- 1994-06-15 WO PCT/EP1994/001960 patent/WO1995000512A1/en active IP Right Grant
- 1994-06-15 KR KR1019950705316A patent/KR0181560B1/ko not_active Expired - Fee Related
- 1994-06-15 AT AT94918875T patent/ATE171179T1/de active
- 1994-06-15 JP JP7502417A patent/JP2812804B2/ja not_active Expired - Fee Related
- 1994-06-15 HU HU9501970A patent/HU220670B1/hu not_active IP Right Cessation
- 1994-06-15 CZ CZ953366A patent/CZ284350B6/cs not_active IP Right Cessation
- 1994-06-15 PL PL94312252A patent/PL176783B1/pl not_active IP Right Cessation
- 1994-06-15 US US08/553,580 patent/US5602134A/en not_active Expired - Fee Related
- 1994-06-15 SG SG1996004320A patent/SG49717A1/en unknown
- 1994-06-15 AU AU70008/94A patent/AU679077B2/en not_active Ceased
- 1994-06-15 EP EP94918875A patent/EP0707586B1/en not_active Expired - Lifetime
- 1994-06-15 BR BR9406899A patent/BR9406899A/pt not_active Application Discontinuation
- 1994-06-15 SI SI9420041A patent/SI9420041A/sl not_active IP Right Cessation
- 1994-06-15 CA CA002163122A patent/CA2163122C/en not_active Expired - Fee Related
- 1994-06-15 CN CN94192539A patent/CN1043765C/zh not_active Expired - Fee Related
- 1994-06-15 RU RU96101187A patent/RU2129554C1/ru not_active IP Right Cessation
- 1994-06-15 DE DE69413398T patent/DE69413398T2/de not_active Expired - Fee Related
- 1994-06-15 SK SK1596-95A patent/SK280400B6/sk unknown
- 1994-06-17 LT LTIP1960A patent/LT3447B/lt not_active IP Right Cessation
- 1994-06-17 MY MYPI94001564A patent/MY110751A/en unknown
- 1994-06-20 IL IL110055A patent/IL110055A/xx not_active IP Right Cessation
- 1994-06-20 ZA ZA944382A patent/ZA944382B/xx unknown
-
1995
- 1995-12-08 BG BG100209A patent/BG62171B1/bg unknown
- 1995-12-12 NO NO955028A patent/NO305366B1/no unknown
- 1995-12-20 FI FI956143A patent/FI109124B/fi active
- 1995-12-21 OA OA60756A patent/OA10202A/en unknown
-
1996
- 1996-01-19 LV LVP-96-13A patent/LV11545B/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2190676B (en) | 1986-05-23 | 1990-05-30 | Bristol Myers Co | Imidazoquinolinylether derivatives |
| EP0406958A2 (en) | 1989-07-07 | 1991-01-09 | Janssen Pharmaceutica N.V. | Positive inotropic and lusitropic 3,5-dihydroimidazo[2,1-b]quinazolin-2(1H)-one derivatives |
| EP0426180A2 (en) | 1989-11-01 | 1991-05-08 | Bristol-Myers Squibb Company | Imidazo[4,5-b] quinolinyloxyalkanoic acid amides with enhanced water solubility |
| US5196428A (en) | 1992-04-03 | 1993-03-23 | Bristol-Myers Squibb Company | Imidazo[4,5-b]qinolinyl oxy alkyl ureas |
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Effective date: 19980617 |