CA2670168A1 - Amino quinazolines derivatives wuth blood platelet reducing properties - Google Patents
Amino quinazolines derivatives wuth blood platelet reducing properties Download PDFInfo
- Publication number
- CA2670168A1 CA2670168A1 CA002670168A CA2670168A CA2670168A1 CA 2670168 A1 CA2670168 A1 CA 2670168A1 CA 002670168 A CA002670168 A CA 002670168A CA 2670168 A CA2670168 A CA 2670168A CA 2670168 A1 CA2670168 A1 CA 2670168A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- group
- alkyl
- halo
- cyano
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 210000001772 blood platelet Anatomy 0.000 title abstract description 16
- 230000001603 reducing effect Effects 0.000 title description 4
- CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical class C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 208000014767 Myeloproliferative disease Diseases 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000002346 iodo group Chemical group I* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 6
- 208000007536 Thrombosis Diseases 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 4
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 4
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 4
- 238000006241 metabolic reaction Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- OTBXOEAOVRKTNQ-UHFFFAOYSA-N anagrelide Chemical compound N1=C2NC(=O)CN2CC2=C(Cl)C(Cl)=CC=C21 OTBXOEAOVRKTNQ-UHFFFAOYSA-N 0.000 abstract description 61
- 229960001694 anagrelide Drugs 0.000 abstract description 51
- 229940002612 prodrug Drugs 0.000 abstract description 29
- 239000000651 prodrug Substances 0.000 abstract description 29
- 230000000694 effects Effects 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- KJMFQJFNQYWQAV-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinazoline Chemical class C1=NC=NC2=C(NC=N3)C3=CC=C21 KJMFQJFNQYWQAV-UHFFFAOYSA-N 0.000 abstract description 3
- -1 AMINO QUINAZOLINES DERIVATIVES Chemical class 0.000 description 17
- 238000010521 absorption reaction Methods 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- KAXTUTDKZVOONF-UHFFFAOYSA-N 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one Chemical compound N1=C2NC(=O)C(O)N2CC2=C1C=CC(Cl)=C2Cl KAXTUTDKZVOONF-UHFFFAOYSA-N 0.000 description 8
- 230000004060 metabolic process Effects 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 241000282412 Homo Species 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000001732 thrombotic effect Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010579 first pass effect Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- GUKOXKSKUXNFMV-UHFFFAOYSA-N 1,2-dihydroquinazolin-2-amine Chemical class C1=CC=C2C=NC(N)NC2=C1 GUKOXKSKUXNFMV-UHFFFAOYSA-N 0.000 description 1
- ULNVBRUIKLYGDF-UHFFFAOYSA-N 1,3-bis(4-methylphenyl)thiourea Chemical compound C1=CC(C)=CC=C1NC(=S)NC1=CC=C(C)C=C1 ULNVBRUIKLYGDF-UHFFFAOYSA-N 0.000 description 1
- AZBJDUGNSMCMIZ-UHFFFAOYSA-N 2-(2-amino-5,6-dichloro-4H-quinazolin-3-yl)propanoic acid Chemical class N1=C(N)N(C(C)C(O)=O)CC2=C1C=CC(Cl)=C2Cl AZBJDUGNSMCMIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- YLFXXKJQBOJJIX-UHFFFAOYSA-N 6,7-dichloro-5,10-dihydro-3h-imidazo[2,1-b]quinazolin-2-one;hydrate;hydrochloride Chemical compound O.Cl.N1=C2NC(=O)CN2CC2=C(Cl)C(Cl)=CC=C21 YLFXXKJQBOJJIX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
- 102000018832 Cytochromes Human genes 0.000 description 1
- 108010052832 Cytochromes Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101100220044 Homo sapiens CD34 gene Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010033557 Palpitations Diseases 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 208000005485 Thrombocytosis Diseases 0.000 description 1
- 206010043647 Thrombotic Stroke Diseases 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229940060238 agrylin Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 229960003555 anagrelide hydrochloride Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000007214 atherothrombosis Effects 0.000 description 1
- IWXRPVHRDWXIEA-UHFFFAOYSA-N azanium formate hydrate Chemical compound [NH4+].O.[O-]C=O IWXRPVHRDWXIEA-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000007883 bronchodilation Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000004041 inotropic agent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011418 maintenance treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000003593 megakaryocyte Anatomy 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002570 phosphodiesterase III inhibitor Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 208000003476 primary myelofibrosis Diseases 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0623749.9 | 2006-11-28 | ||
| GBGB0623749.9A GB0623749D0 (en) | 2006-11-28 | 2006-11-28 | Substituted quinazolines |
| PCT/GB2007/050698 WO2008065445A1 (en) | 2006-11-28 | 2007-11-19 | Amino quinazolines derivatives wuth blood platelet reducing properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2670168A1 true CA2670168A1 (en) | 2008-06-05 |
Family
ID=37671459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002670168A Abandoned CA2670168A1 (en) | 2006-11-28 | 2007-11-19 | Amino quinazolines derivatives wuth blood platelet reducing properties |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP2097390A1 (es) |
| JP (1) | JP2010511031A (es) |
| KR (1) | KR20090089865A (es) |
| CN (1) | CN101558048B (es) |
| AR (1) | AR064003A1 (es) |
| AU (1) | AU2007327048B2 (es) |
| BR (1) | BRPI0719568A2 (es) |
| CA (1) | CA2670168A1 (es) |
| EA (1) | EA017139B1 (es) |
| GB (1) | GB0623749D0 (es) |
| IL (1) | IL198808A0 (es) |
| MX (1) | MX2009005578A (es) |
| MY (1) | MY149620A (es) |
| TW (1) | TW200829252A (es) |
| WO (1) | WO2008065445A1 (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0822970D0 (en) * | 2008-12-17 | 2009-01-21 | Shire Llc | Process for the preparation of anagrelide and analogues |
| GB201004495D0 (en) | 2010-03-18 | 2010-05-05 | Shire Llc | Subtituted quinazolines |
| CN103254197A (zh) * | 2013-05-29 | 2013-08-21 | 黑龙江大学 | 一种盐酸阿那格雷的制备方法 |
| PL3236967T3 (pl) | 2014-12-22 | 2020-04-30 | Suda Pharmaceuticals Ltd | Zapobieganie i leczenie przerzutów u pacjentów z nadpłytkowością typu nowotworowego |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146718A (en) * | 1978-04-10 | 1979-03-27 | Bristol-Myers Company | Alkyl 5,6-dichloro-3,4-dihydro-2(1h)-iminoquinazoline-3-acetate hydrohalides |
| US6194420B1 (en) * | 1999-11-30 | 2001-02-27 | Roberts Laboratories Inc. | 2-amino-5,6-dichloro-3,4-dihydroquinazoline, its method of making and using and pharmaceutical compositions thereof |
| DE10301105B4 (de) * | 2003-01-09 | 2005-11-24 | Chemisch-Pharmazeutisches Labor, Rolf Sachse Gmbh | Verwendung von 2-Amino-2H-chinazolin-Derivaten zur Behandlung von myeloproliferativen Erkrankungen, Bluthochdruck und Bronchodilation |
| EA010871B1 (ru) * | 2003-01-23 | 2008-12-30 | Шир Холдингз Аг | Трансдермальные составы и способы лечения тромбоцитемии |
| US7700608B2 (en) * | 2004-08-04 | 2010-04-20 | Shire Holdings Ag | Quinazoline derivatives and their use in the treatment of thrombocythemia |
-
2006
- 2006-11-28 GB GBGB0623749.9A patent/GB0623749D0/en not_active Ceased
-
2007
- 2007-11-19 WO PCT/GB2007/050698 patent/WO2008065445A1/en active Application Filing
- 2007-11-19 MY MYPI20092152A patent/MY149620A/en unknown
- 2007-11-19 MX MX2009005578A patent/MX2009005578A/es not_active Application Discontinuation
- 2007-11-19 KR KR1020097011681A patent/KR20090089865A/ko not_active Application Discontinuation
- 2007-11-19 JP JP2009538793A patent/JP2010511031A/ja active Pending
- 2007-11-19 BR BRPI0719568-0A patent/BRPI0719568A2/pt not_active IP Right Cessation
- 2007-11-19 EP EP07824910A patent/EP2097390A1/en not_active Withdrawn
- 2007-11-19 EA EA200900742A patent/EA017139B1/ru not_active IP Right Cessation
- 2007-11-19 CA CA002670168A patent/CA2670168A1/en not_active Abandoned
- 2007-11-19 AU AU2007327048A patent/AU2007327048B2/en not_active Ceased
- 2007-11-19 CN CN2007800442221A patent/CN101558048B/zh not_active Expired - Fee Related
- 2007-11-27 TW TW096145029A patent/TW200829252A/zh unknown
- 2007-11-28 AR ARP070105273A patent/AR064003A1/es unknown
-
2009
- 2009-05-19 IL IL198808A patent/IL198808A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0719568A2 (pt) | 2013-12-10 |
| MX2009005578A (es) | 2009-07-29 |
| MY149620A (en) | 2013-09-13 |
| JP2010511031A (ja) | 2010-04-08 |
| EP2097390A1 (en) | 2009-09-09 |
| TW200829252A (en) | 2008-07-16 |
| AU2007327048B2 (en) | 2012-01-12 |
| CN101558048B (zh) | 2012-07-25 |
| WO2008065445A1 (en) | 2008-06-05 |
| AU2007327048A1 (en) | 2008-06-05 |
| EA017139B1 (ru) | 2012-10-30 |
| IL198808A0 (en) | 2010-02-17 |
| GB0623749D0 (en) | 2007-01-10 |
| EA200900742A1 (ru) | 2010-08-30 |
| AR064003A1 (es) | 2009-03-04 |
| KR20090089865A (ko) | 2009-08-24 |
| CN101558048A (zh) | 2009-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20131119 |