CA2385918A1 - Quinazolinones - Google Patents
Quinazolinones Download PDFInfo
- Publication number
- CA2385918A1 CA2385918A1 CA002385918A CA2385918A CA2385918A1 CA 2385918 A1 CA2385918 A1 CA 2385918A1 CA 002385918 A CA002385918 A CA 002385918A CA 2385918 A CA2385918 A CA 2385918A CA 2385918 A1 CA2385918 A1 CA 2385918A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- aminomethyl
- quinazolin
- cyclohexylmethyl
- formula ila
- 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
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000012453 solvate Substances 0.000 claims abstract description 20
- 239000005557 antagonist Substances 0.000 claims abstract description 9
- 102000003886 Glycoproteins Human genes 0.000 claims abstract description 7
- 108090000288 Glycoproteins Proteins 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 133
- -1 heteroaryl bromide Chemical compound 0.000 claims description 110
- 238000006243 chemical reaction Methods 0.000 claims description 90
- 239000007790 solid phase Substances 0.000 claims description 39
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 208000007536 Thrombosis Diseases 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 206010038563 Reocclusion Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 3
- 238000002399 angioplasty Methods 0.000 claims description 3
- 230000000181 anti-adherent effect Effects 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- 238000002513 implantation Methods 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- GVFWZYXEQYUWEP-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-2-naphthalen-1-ylquinazolin-4-one Chemical compound C1C(CN)CCCC1CN1C(=O)C2=CC=CC=C2N=C1C1=CC=CC2=CC=CC=C12 GVFWZYXEQYUWEP-UHFFFAOYSA-N 0.000 claims description 2
- OSWDUWPBLQGVQV-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-2-naphthalen-2-ylquinazolin-4-one Chemical compound C1C(CN)CCCC1CN1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C=CC=C2)C2=C1 OSWDUWPBLQGVQV-UHFFFAOYSA-N 0.000 claims description 2
- BAENOGJYZAJKKI-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-6-chloro-2-naphthalen-2-ylquinazolin-4-one Chemical compound C1C(CN)CCCC1CN1C(=O)C2=CC(Cl)=CC=C2N=C1C1=CC=C(C=CC=C2)C2=C1 BAENOGJYZAJKKI-UHFFFAOYSA-N 0.000 claims description 2
- AMNDVWLNWHTDCW-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-6-methoxy-2-(5-thiophen-2-ylthiophen-2-yl)quinazolin-4-one Chemical compound C1CCC(CN)CC1CN1C(=O)C2=CC(OC)=CC=C2N=C1C(S1)=CC=C1C1=CC=CS1 AMNDVWLNWHTDCW-UHFFFAOYSA-N 0.000 claims description 2
- HDFKXEBHUWZGSS-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-6-methoxy-2-naphthalen-1-ylquinazolin-4-one Chemical compound O=C1C2=CC(OC)=CC=C2N=C(C=2C3=CC=CC=C3C=CC=2)N1CC1CCCC(CN)C1 HDFKXEBHUWZGSS-UHFFFAOYSA-N 0.000 claims description 2
- MUCBMJNEMNIDJY-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-6-methoxy-2-naphthalen-2-ylquinazolin-4-one Chemical compound O=C1C2=CC(OC)=CC=C2N=C(C=2C=C3C=CC=CC3=CC=2)N1CC1CCCC(CN)C1 MUCBMJNEMNIDJY-UHFFFAOYSA-N 0.000 claims description 2
- BPIRKARGZPNEPK-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-6-methyl-2-naphthalen-1-ylquinazolin-4-one Chemical compound O=C1C2=CC(C)=CC=C2N=C(C=2C3=CC=CC=C3C=CC=2)N1CC1CCCC(CN)C1 BPIRKARGZPNEPK-UHFFFAOYSA-N 0.000 claims description 2
- IWQMMPFQCAIXGC-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-6-methyl-2-naphthalen-2-ylquinazolin-4-one Chemical compound O=C1C2=CC(C)=CC=C2N=C(C=2C=C3C=CC=CC3=CC=2)N1CC1CCCC(CN)C1 IWQMMPFQCAIXGC-UHFFFAOYSA-N 0.000 claims description 2
- FKCXEDXHRKTJFR-UHFFFAOYSA-N 3-[[3-(aminomethyl)cyclohexyl]methyl]-7-chloro-2-naphthalen-2-ylquinazolin-4-one Chemical compound C1C(CN)CCCC1CN1C(=O)C2=CC=C(Cl)C=C2N=C1C1=CC=C(C=CC=C2)C2=C1 FKCXEDXHRKTJFR-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 150000001499 aryl bromides Chemical class 0.000 claims description 2
- 150000001503 aryl iodides Chemical class 0.000 claims description 2
- 125000005620 boronic acid group Chemical class 0.000 claims description 2
- 238000005661 deetherification reaction Methods 0.000 claims description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004962 sulfoxyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 1
- 238000004949 mass spectrometry Methods 0.000 description 99
- 229920005989 resin Polymers 0.000 description 76
- 239000011347 resin Substances 0.000 description 76
- 238000003776 cleavage reaction Methods 0.000 description 54
- 230000007017 scission Effects 0.000 description 54
- 125000006239 protecting group Chemical group 0.000 description 42
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 230000003647 oxidation Effects 0.000 description 28
- 238000007254 oxidation reaction Methods 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 27
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000454 talc Substances 0.000 description 8
- 235000012222 talc Nutrition 0.000 description 8
- 229910052623 talc Inorganic materials 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 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 6
- 239000003814 drug Substances 0.000 description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000003746 solid phase reaction Methods 0.000 description 6
- 125000000565 sulfonamide group Chemical group 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000002792 vascular Effects 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
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- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
La présente invention concerne des quinazolinones de formule (I) dans laquelle R, R?1¿, R?2¿, R?3¿, R?4¿, Y, n et m sont tels que définis dans la revendication 1, leurs sels ou leurs solvates agissant comme antagonistes IbIX glycoprotéines.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40793999A | 1999-09-28 | 1999-09-28 | |
| US09/407,939 | 1999-09-28 | ||
| PCT/EP2000/008939 WO2001023364A1 (fr) | 1999-09-28 | 2000-09-13 | Quinazolinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2385918A1 true CA2385918A1 (fr) | 2001-04-05 |
Family
ID=23614192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002385918A Abandoned CA2385918A1 (fr) | 1999-09-28 | 2000-09-13 | Quinazolinones |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1216233A1 (fr) |
| KR (1) | KR20020047185A (fr) |
| AR (1) | AR025796A1 (fr) |
| AU (1) | AU7419300A (fr) |
| BR (1) | BR0014311A (fr) |
| CA (1) | CA2385918A1 (fr) |
| NO (1) | NO20021503D0 (fr) |
| WO (1) | WO2001023364A1 (fr) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7671200B2 (en) | 1999-10-27 | 2010-03-02 | Cytokinetics, Inc. | Quinazolinone KSP inhibitors |
| US7230000B1 (en) | 1999-10-27 | 2007-06-12 | Cytokinetics, Incorporated | Methods and compositions utilizing quinazolinones |
| US6545004B1 (en) | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| WO2003070701A2 (fr) | 2002-02-15 | 2003-08-28 | Cytokinetics, Inc. | Syntheses de quinazolinones |
| US7214800B2 (en) | 2002-05-09 | 2007-05-08 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| CA2485148A1 (fr) | 2002-05-09 | 2003-11-20 | Cytokinetics, Inc. | Composes, compositions et procedes |
| EP1513820A4 (fr) | 2002-05-23 | 2006-09-13 | Cytokinetics Inc | Composes, compositions et procedes |
| WO2003106426A1 (fr) | 2002-06-14 | 2003-12-24 | Cytokinetics, Inc. | Composes, compositions et procedes |
| AU2003256805A1 (en) | 2002-07-23 | 2004-02-09 | Cytokinetics, Inc. | Compounds compositions and methods |
| WO2004034972A2 (fr) | 2002-09-30 | 2004-04-29 | Cytokinetics, Inc. | Composes, compositions, et procedes |
| US7550590B2 (en) | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| KR20060041309A (ko) | 2003-08-13 | 2006-05-11 | 다케다 야쿠힌 고교 가부시키가이샤 | 4-피리미돈 유도체 및 펩티딜 펩티다제 저해제로서의 그의용도 |
| US7790734B2 (en) | 2003-09-08 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| EP1692112A4 (fr) | 2003-12-08 | 2008-09-24 | Cytokinetics Inc | Composes, compositions, et methodes associees |
| CN102127057A (zh) | 2004-03-15 | 2011-07-20 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
| WO2006068978A2 (fr) | 2004-12-21 | 2006-06-29 | Takeda Pharmaceutial Company Limited | Inhibiteurs de dipeptidyle peptidase |
| GEP20135838B (en) | 2005-09-14 | 2013-06-10 | Takeda Pharmaceutical | Dipeptidyl peptidase inhibitors usage at diabetes treatment |
| CN101360723A (zh) | 2005-09-16 | 2009-02-04 | 武田药品工业株式会社 | 制备嘧啶二酮衍生物的方法 |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5783577A (en) * | 1995-09-15 | 1998-07-21 | Trega Biosciences, Inc. | Synthesis of quinazolinone libraries and derivatives thereof |
-
2000
- 2000-09-13 CA CA002385918A patent/CA2385918A1/fr not_active Abandoned
- 2000-09-13 KR KR1020027003906A patent/KR20020047185A/ko not_active Withdrawn
- 2000-09-13 EP EP00962482A patent/EP1216233A1/fr not_active Withdrawn
- 2000-09-13 WO PCT/EP2000/008939 patent/WO2001023364A1/fr not_active Ceased
- 2000-09-13 AU AU74193/00A patent/AU7419300A/en not_active Abandoned
- 2000-09-13 BR BR0014311-1A patent/BR0014311A/pt not_active Application Discontinuation
- 2000-09-27 AR ARP000105075A patent/AR025796A1/es unknown
-
2002
- 2002-03-26 NO NO20021503A patent/NO20021503D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0014311A (pt) | 2002-05-21 |
| NO20021503L (no) | 2002-03-26 |
| EP1216233A1 (fr) | 2002-06-26 |
| NO20021503D0 (no) | 2002-03-26 |
| KR20020047185A (ko) | 2002-06-21 |
| WO2001023364A1 (fr) | 2001-04-05 |
| AR025796A1 (es) | 2002-12-11 |
| AU7419300A (en) | 2001-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |