HRP980106A2 - Atropisomers of 3-aryl-4 (3h)-quinazolinones - Google Patents
Atropisomers of 3-aryl-4 (3h)-quinazolinonesInfo
- Publication number
- HRP980106A2 HRP980106A2 HR60/038,905A HRP980106A HRP980106A2 HR P980106 A2 HRP980106 A2 HR P980106A2 HR P980106 A HRP980106 A HR P980106A HR P980106 A2 HRP980106 A2 HR P980106A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- fluoro
- chloro
- methyl
- hydrogen
- Prior art date
Links
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 118
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 66
- 229920002554 vinyl polymer Polymers 0.000 claims description 52
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
- -1 CF 3 Chemical group 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 229940079593 drug Drugs 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 22
- 208000007101 Muscle Cramp Diseases 0.000 claims description 20
- 208000005392 Spasm Diseases 0.000 claims description 20
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 20
- 229940127240 opiate Drugs 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 238000001356 surgical procedure Methods 0.000 claims description 20
- 208000002193 Pain Diseases 0.000 claims description 19
- 206010013663 drug dependence Diseases 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 206010003497 Asphyxia Diseases 0.000 claims description 12
- 201000006474 Brain Ischemia Diseases 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 12
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- 230000002490 cerebral effect Effects 0.000 claims description 12
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- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 11
- 206010008118 cerebral infarction Diseases 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
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- 208000010496 Heart Arrest Diseases 0.000 claims description 10
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- 208000019695 Migraine disease Diseases 0.000 claims description 10
- 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 10
- 208000028017 Psychotic disease Diseases 0.000 claims description 10
- 208000021063 Respiratory fume inhalation disease Diseases 0.000 claims description 10
- 208000017442 Retinal disease Diseases 0.000 claims description 10
- 206010038923 Retinopathy Diseases 0.000 claims description 10
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 10
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- 230000001684 chronic effect Effects 0.000 claims description 10
- 229960003920 cocaine Drugs 0.000 claims description 10
- 230000007547 defect Effects 0.000 claims description 10
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- 231100000869 headache Toxicity 0.000 claims description 10
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 10
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- 201000001119 neuropathy Diseases 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 208000033300 perinatal asphyxia Diseases 0.000 claims description 10
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 10
- 230000002207 retinal effect Effects 0.000 claims description 10
- 210000000278 spinal cord Anatomy 0.000 claims description 10
- 208000011117 substance-related disease Diseases 0.000 claims description 10
- 231100000886 tinnitus Toxicity 0.000 claims description 10
- 238000002054 transplantation Methods 0.000 claims description 10
- 230000008733 trauma Effects 0.000 claims description 10
- 208000022497 Cocaine-Related disease Diseases 0.000 claims description 9
- 206010057852 Nicotine dependence Diseases 0.000 claims description 9
- 208000026251 Opioid-Related disease Diseases 0.000 claims description 9
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 9
- 208000005298 acute pain Diseases 0.000 claims description 9
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 9
- 201000006145 cocaine dependence Diseases 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 201000005040 opiate dependence Diseases 0.000 claims description 9
- 150000001356 alkyl thiols Chemical class 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 206010027599 migraine Diseases 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 206010042772 syncope Diseases 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 102000005962 receptors Human genes 0.000 claims description 6
- 108020003175 receptors Proteins 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 230000003042 antagnostic effect Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 208000003443 Unconsciousness Diseases 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000002585 base Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 235000011054 acetic acid Nutrition 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 10
- 229940098747 AMPA receptor antagonist Drugs 0.000 description 9
- 239000000775 AMPA receptor antagonist Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
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- 239000012442 inert solvent Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- 239000011592 zinc chloride Substances 0.000 description 8
- 235000005074 zinc chloride Nutrition 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
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- 229910019142 PO4 Inorganic materials 0.000 description 4
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- YIKRYWHYPPRTPL-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1,3-thiazole-4-carbaldehyde Chemical compound CN(C)CC1=NC(C=O)=CS1 YIKRYWHYPPRTPL-UHFFFAOYSA-N 0.000 description 3
- AEHWVNPVEUVPMT-UHFFFAOYSA-N 2-methyl-1,3-thiazole-4-carbaldehyde Chemical compound CC1=NC(C=O)=CS1 AEHWVNPVEUVPMT-UHFFFAOYSA-N 0.000 description 3
- HYHNPUGUPISSQO-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-[2-[6-(diethylaminomethyl)pyridin-2-yl]ethenyl]-6-fluoroquinazolin-4-one Chemical compound CCN(CC)CC1=CC=CC(C=CC=2N(C(=O)C3=CC(F)=CC=C3N=2)C=2C(=CC=CC=2)Cl)=N1 HYHNPUGUPISSQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3890597P | 1997-02-28 | 1997-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980106A2 true HRP980106A2 (en) | 1999-02-28 |
Family
ID=21902563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR60/038,905A HRP980106A2 (en) | 1997-02-28 | 1998-02-27 | Atropisomers of 3-aryl-4 (3h)-quinazolinones |
Country Status (40)
| Country | Link |
|---|---|
| US (1) | US6306864B1 (xx) |
| EP (1) | EP0968194B1 (xx) |
| JP (1) | JP2000509731A (xx) |
| KR (1) | KR100358636B1 (xx) |
| CN (1) | CN1248248A (xx) |
| AP (1) | AP859A (xx) |
| AR (1) | AR011170A1 (xx) |
| AT (1) | ATE267817T1 (xx) |
| AU (1) | AU744028B2 (xx) |
| BG (1) | BG103689A (xx) |
| BR (1) | BR9807872A (xx) |
| CA (1) | CA2282277C (xx) |
| DE (1) | DE69824157T2 (xx) |
| DK (1) | DK0968194T3 (xx) |
| DZ (1) | DZ2440A1 (xx) |
| EA (1) | EA001963B1 (xx) |
| ES (1) | ES2219866T3 (xx) |
| GT (1) | GT199800038A (xx) |
| HR (1) | HRP980106A2 (xx) |
| HU (1) | HUP0000914A3 (xx) |
| ID (1) | ID22711A (xx) |
| IL (1) | IL130900A0 (xx) |
| IS (1) | IS1952B (xx) |
| MA (1) | MA24484A1 (xx) |
| NO (1) | NO313630B1 (xx) |
| NZ (1) | NZ336628A (xx) |
| OA (1) | OA11089A (xx) |
| PA (1) | PA8447001A1 (xx) |
| PE (1) | PE58399A1 (xx) |
| PL (1) | PL335418A1 (xx) |
| PT (1) | PT968194E (xx) |
| SK (1) | SK113299A3 (xx) |
| TN (1) | TNSN98035A1 (xx) |
| TR (1) | TR199902093T2 (xx) |
| TW (1) | TW504508B (xx) |
| UA (1) | UA61097C2 (xx) |
| UY (1) | UY24897A1 (xx) |
| WO (1) | WO1998038173A1 (xx) |
| YU (1) | YU41299A (xx) |
| ZA (1) | ZA981666B (xx) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0901487B9 (en) | 1996-05-15 | 2004-09-29 | Pfizer Inc. | 2,3,6 trisubstituted-4(3h)-quinazolinones |
| US6323208B1 (en) * | 1997-09-05 | 2001-11-27 | Pfizer Inc | Atropisomers of 2,3-disubstituted-(5.6)-heteroaryl fused-pyrimidin-4-ones |
| JPH11279158A (ja) * | 1998-02-09 | 1999-10-12 | Pfizer Prod Inc | キナゾリン―４―オン誘導体の製造方法 |
| US6667300B2 (en) | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| EP1278748B1 (en) * | 2000-04-25 | 2011-03-23 | ICOS Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
| PT1300396E (pt) | 2000-06-12 | 2009-04-20 | Eisai R&D Man Co Ltd | Compostos de 1,2-di-hidropiridina, processos para a sua preparação e sua utilização |
| YU12203A (sh) | 2000-08-18 | 2006-03-03 | Ajinomoto Co.Inc. | Novi derivati fenilalanina |
| GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| US6939968B2 (en) * | 2002-12-23 | 2005-09-06 | Bristol-Myers Squibb Company | Atropisomers of 3-substituted-4-arylquinolin-2-one derivatives |
| US20080146562A1 (en) * | 2003-08-08 | 2008-06-19 | Ulysses Pharmaceutical Products Inc., | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| CA2534405A1 (en) * | 2003-08-08 | 2005-02-17 | Ulysses Pharmaceutical Products Inc. | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| GB0325390D0 (en) * | 2003-10-30 | 2003-12-03 | Novartis Ag | Organic compounds |
| KR20110098980A (ko) | 2003-12-22 | 2011-09-02 | 아지노모토 가부시키가이샤 | 신규한 페닐알라닌 유도체 |
| LT2612862T (lt) | 2004-05-13 | 2017-01-25 | Icos Corporation | Chinazolinonai kaip žmogaus fosfatidilinozitol-3-kinazės delta inhibitoriai |
| MY148809A (en) | 2004-07-06 | 2013-05-31 | Eisai R&D Man Co Ltd | Crystals of 1,2-dihydropyridine compound and their production process |
| GB0416730D0 (en) * | 2004-07-27 | 2004-09-01 | Novartis Ag | Organic compounds |
| TWI409070B (zh) | 2005-11-04 | 2013-09-21 | Hydra Biosciences Inc | 用於調節ｔｒｐｖ３功能之化合物 |
| JP2010505811A (ja) | 2006-10-04 | 2010-02-25 | ファイザー・プロダクツ・インク | カルシウム受容体アンタゴニストとしてのピリド［４，３−ｄ］ピリミジン−４（３Ｈ）−オン誘導体 |
| WO2008140750A1 (en) | 2007-05-10 | 2008-11-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
| CN101429166B (zh) * | 2007-11-07 | 2013-08-21 | 上海特化医药科技有限公司 | 喹唑啉酮衍生物及其制备方法和用途 |
| US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
| KR20170060179A (ko) | 2008-11-13 | 2017-05-31 | 길리아드 칼리스토가 엘엘씨 | 혈액 종양에 대한 요법 |
| KR20120002995A (ko) | 2009-03-24 | 2012-01-09 | 길리아드 칼리스토가 엘엘씨 | ２―퓨리닐―３―톨릴―퀴나졸리논 유도체의 회전장애 이성질체 및 사용 방법 |
| KR20120049281A (ko) | 2009-07-21 | 2012-05-16 | 길리아드 칼리스토가 엘엘씨 | Ｐｉ３ｋ 억제제를 이용한 간 장애의 치료 |
| KR20140133590A (ko) | 2012-03-05 | 2014-11-19 | 길리아드 칼리스토가 엘엘씨 | (s)-2-(1-(9h-퓨린-6-일아미노)프로필)-5-플루오로-3-페닐퀴나졸린-4(3h)-온의 다형체 형태 |
| CN103275086B (zh) * | 2013-05-30 | 2015-04-15 | 温州大学 | 一种6-取代喹唑啉并喹唑啉酮化合物及其合成方法和用途 |
| EP3083623A1 (en) | 2013-12-20 | 2016-10-26 | Gilead Calistoga LLC | Polymorphic forms of a hydrochloride salt of (s) -2-(9h-purin-6-ylamino) propyl) -5-fluoro-3-phenylquinazolin-4 (3h) -one |
| EP3594215A1 (en) | 2013-12-20 | 2020-01-15 | Gilead Calistoga LLC | Intermediate products in process methods for the preparation of phosphatidylinositol 3-kinase inhibitors |
| US9533909B2 (en) | 2014-03-31 | 2017-01-03 | Corning Incorporated | Methods and apparatus for material processing using atmospheric thermal plasma reactor |
| EP3154960A1 (en) | 2014-06-13 | 2017-04-19 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| DE102014217021A1 (de) * | 2014-08-27 | 2016-03-03 | Skf Lubrication Systems Germany Ag | Gehäuse für eine Vorrichtung zum dosierten Verteilen eines Mediums sowie eine Dosiereinrichtung zur Verwendung in dem Gehäuse |
| AU2019395288A1 (en) | 2018-12-14 | 2021-09-23 | Eisai R&D Management Co., Ltd. | Aqueous based pharmaceutical formulations of 1,2-dihydropyridine compounds |
| EP4096661A4 (en) | 2020-01-29 | 2024-03-06 | Kamari Pharma Ltd. | COMPOUNDS AND COMPOSITIONS FOR USE IN TREATING SKIN DISEASES |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1195321B (de) * | 1962-03-16 | 1965-06-24 | Troponwerke Dinklage & Co | Verfahren zur Herstellung von substituierten Chinazolon-(4)-derivaten |
| DE1670416A1 (de) * | 1966-12-30 | 1971-02-11 | Chem Fab Von Heyden Gmbh Muenc | Verfahren zur Herstellung von aminosubstituierten Chinazolinonderivaten |
| GB1298603A (en) * | 1970-04-06 | 1972-12-06 | Karamchand Premchand Private | Quinazolinone derivatives |
| US4183931A (en) * | 1977-09-08 | 1980-01-15 | Research Corporation | 2-Ketoalkyl-4(3H)-quinazolinones |
| GB9022785D0 (en) * | 1990-10-19 | 1990-12-05 | Merck Sharp & Dohme | Therapeutic agents |
| WO1992013535A1 (en) * | 1991-02-06 | 1992-08-20 | Research Corporation Technologies, Inc. | Anticonvulsant substituted quinazolones |
| US5777271A (en) * | 1996-01-18 | 1998-07-07 | Commscope, Inc. | Cable having an at least partially oxidized armor layer |
| EP0901487B9 (en) * | 1996-05-15 | 2004-09-29 | Pfizer Inc. | 2,3,6 trisubstituted-4(3h)-quinazolinones |
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1998
- 1998-02-06 JP JP10537448A patent/JP2000509731A/ja active Pending
- 1998-02-06 SK SK1132-99A patent/SK113299A3/sk unknown
- 1998-02-06 TR TR1999/02093T patent/TR199902093T2/xx unknown
- 1998-02-06 IL IL13090098A patent/IL130900A0/xx unknown
- 1998-02-06 CN CN98802638A patent/CN1248248A/zh active Pending
- 1998-02-06 NZ NZ336628A patent/NZ336628A/xx unknown
- 1998-02-06 AU AU56768/98A patent/AU744028B2/en not_active Ceased
- 1998-02-06 PL PL98335418A patent/PL335418A1/xx unknown
- 1998-02-06 PT PT98900978T patent/PT968194E/pt unknown
- 1998-02-06 ID IDW990937A patent/ID22711A/id unknown
- 1998-02-06 WO PCT/IB1998/000150 patent/WO1998038173A1/en not_active Application Discontinuation
- 1998-02-06 CA CA002282277A patent/CA2282277C/en not_active Expired - Fee Related
- 1998-02-06 EA EA199900693A patent/EA001963B1/ru not_active IP Right Cessation
- 1998-02-06 ES ES98900978T patent/ES2219866T3/es not_active Expired - Lifetime
- 1998-02-06 YU YU41299A patent/YU41299A/sh unknown
- 1998-02-06 DE DE69824157T patent/DE69824157T2/de not_active Expired - Fee Related
- 1998-02-06 US US09/367,960 patent/US6306864B1/en not_active Expired - Fee Related
- 1998-02-06 EP EP98900978A patent/EP0968194B1/en not_active Expired - Lifetime
- 1998-02-06 KR KR1019997007887A patent/KR100358636B1/ko not_active IP Right Cessation
- 1998-02-06 DK DK98900978T patent/DK0968194T3/da active
- 1998-02-06 AT AT98900978T patent/ATE267817T1/de not_active IP Right Cessation
- 1998-02-06 BR BR9807872A patent/BR9807872A/pt not_active Application Discontinuation
- 1998-02-06 HU HU0000914A patent/HUP0000914A3/hu unknown
- 1998-02-17 PA PA19988447001A patent/PA8447001A1/es unknown
- 1998-02-19 GT GT199800038A patent/GT199800038A/es unknown
- 1998-02-20 UY UY24897A patent/UY24897A1/es not_active Application Discontinuation
- 1998-02-23 PE PE1998000126A patent/PE58399A1/es not_active Application Discontinuation
- 1998-02-25 MA MA24978A patent/MA24484A1/fr unknown
- 1998-02-25 TN TNTNSN98035A patent/TNSN98035A1/fr unknown
- 1998-02-25 DZ DZ980050A patent/DZ2440A1/xx active
- 1998-02-25 TW TW087102714A patent/TW504508B/zh not_active IP Right Cessation
- 1998-02-26 AR ARP980100871A patent/AR011170A1/es not_active Application Discontinuation
- 1998-02-26 AP APAP/P/1998/001199A patent/AP859A/en active
- 1998-02-27 ZA ZA9801666A patent/ZA981666B/xx unknown
- 1998-02-27 HR HR60/038,905A patent/HRP980106A2/hr not_active Application Discontinuation
- 1998-06-02 UA UA99084849A patent/UA61097C2/uk unknown
-
1999
- 1999-07-30 IS IS5140A patent/IS1952B/is unknown
- 1999-08-20 OA OA9900187A patent/OA11089A/en unknown
- 1999-08-24 BG BG103689A patent/BG103689A/bg unknown
- 1999-08-27 NO NO19994177A patent/NO313630B1/no not_active IP Right Cessation
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