HRP20020943A2 - Imidazopyrimidine derivatives and triazolopyrimidine derivatives - Google Patents
Imidazopyrimidine derivatives and triazolopyrimidine derivativesInfo
- Publication number
- HRP20020943A2 HRP20020943A2 HR20020943A HRP20020943A HRP20020943A2 HR P20020943 A2 HRP20020943 A2 HR P20020943A2 HR 20020943 A HR20020943 A HR 20020943A HR P20020943 A HRP20020943 A HR P20020943A HR P20020943 A2 HRP20020943 A2 HR P20020943A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- optionally substituted
- amino
- carbonyl
- phenyl
- Prior art date
Links
- 150000005237 imidazopyrimidines Chemical class 0.000 title description 6
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 266
- -1 morpholino, piperidino Chemical group 0.000 claims description 127
- 150000001875 compounds Chemical class 0.000 claims description 100
- 229910052736 halogen Inorganic materials 0.000 claims description 79
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 70
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 65
- 150000002367 halogens Chemical class 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 39
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 102000000551 Syk Kinase Human genes 0.000 claims description 16
- 108010016672 Syk Kinase Proteins 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 12
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 208000026935 allergic disease Diseases 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 4
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- GNPSSNHHJJHBSZ-UHFFFAOYSA-N 1-piperazin-1-ylpyrrolidin-2-one Chemical class O=C1CCCN1N1CCNCC1 GNPSSNHHJJHBSZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 206010010741 Conjunctivitis Diseases 0.000 claims description 3
- 208000010201 Exanthema Diseases 0.000 claims description 3
- 208000004262 Food Hypersensitivity Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 230000006806 disease prevention Effects 0.000 claims description 3
- 201000005884 exanthem Diseases 0.000 claims description 3
- 235000020932 food allergy Nutrition 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 206010037844 rash Diseases 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 208000018464 vernal keratoconjunctivitis Diseases 0.000 claims description 3
- NDCLUOPTSSFKPV-UHFFFAOYSA-N 2-[[7-(3,4-dimethoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]amino]-5-methoxybenzamide Chemical compound NC(=O)C1=CC(OC)=CC=C1NC1=NC(C=2C=C(OC)C(OC)=CC=2)=CC2=NC=CN12 NDCLUOPTSSFKPV-UHFFFAOYSA-N 0.000 claims description 2
- CZQVOIDVDAVDFW-UHFFFAOYSA-N 2-[[7-(3,4-dimethoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]amino]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC=CN2C(NC=2C(=CC=CC=2)C(N)=O)=N1 CZQVOIDVDAVDFW-UHFFFAOYSA-N 0.000 claims description 2
- BXPVALMRYKVZOK-UHFFFAOYSA-N 2-[[7-(3,4-dimethoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]amino]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC=CN2C(NC=2C(=CC=CC=2)S(N)(=O)=O)=N1 BXPVALMRYKVZOK-UHFFFAOYSA-N 0.000 claims description 2
- WKMHAEYCVGWARL-UHFFFAOYSA-N 2-[[7-(3-methoxy-4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]amino]benzamide Chemical compound COC1=CC(C=2N=C(NC=3C(=CC=CC=3)C(N)=O)N3C=CN=C3C=2)=CC=C1N1CCOCC1 WKMHAEYCVGWARL-UHFFFAOYSA-N 0.000 claims description 2
- RKMIGNBIDLMVIX-UHFFFAOYSA-N 2-[[7-(3-methoxy-4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]amino]pyridine-3-carboxamide Chemical compound COC1=CC(C=2N=C(NC=3C(=CC=CN=3)C(N)=O)N3C=CN=C3C=2)=CC=C1N1CCOCC1 RKMIGNBIDLMVIX-UHFFFAOYSA-N 0.000 claims description 2
- NZGHKWGDVNESBP-UHFFFAOYSA-N 4-[[7-(3-methoxy-4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]amino]phenol Chemical compound COC1=CC(C=2N=C(NC=3C=CC(O)=CC=3)N3C=CN=C3C=2)=CC=C1N1CCOCC1 NZGHKWGDVNESBP-UHFFFAOYSA-N 0.000 claims description 2
- JUDZGQKOVLNJJD-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-n-(1h-indazol-6-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC=NN2C(NC=2C=C3NN=CC3=CC=2)=N1 JUDZGQKOVLNJJD-UHFFFAOYSA-N 0.000 claims description 2
- NKTQPBWZINMNES-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-n-(1h-indazol-6-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC=CN2C(NC=2C=C3NN=CC3=CC=2)=N1 NKTQPBWZINMNES-UHFFFAOYSA-N 0.000 claims description 2
- XFZMGMWMVAGMKK-UHFFFAOYSA-N 7-(3-methoxy-4-morpholin-4-ylphenyl)-n-(4-methylphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound COC1=CC(C=2N=C(NC=3C=CC(C)=CC=3)N3C=CN=C3C=2)=CC=C1N1CCOCC1 XFZMGMWMVAGMKK-UHFFFAOYSA-N 0.000 claims description 2
- VZRPLPVDTITFRR-UHFFFAOYSA-N 7-[3-methoxy-4-[2-methoxyethyl(methyl)amino]phenyl]-n-(2-methylsulfonylphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1=C(OC)C(N(C)CCOC)=CC=C1C1=CC2=NC=CN2C(NC=2C(=CC=CC=2)S(C)(=O)=O)=N1 VZRPLPVDTITFRR-UHFFFAOYSA-N 0.000 claims description 2
- 241000737241 Cocos Species 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims 3
- 206010016946 Food allergy Diseases 0.000 claims 2
- 230000015271 coagulation Effects 0.000 claims 2
- 238000005345 coagulation Methods 0.000 claims 2
- JWQOJVOKBAAAAR-UHFFFAOYSA-N 2-[[7-(3,4-dimethoxyphenyl)-5-imidazo[1,2-c]pyrimidinyl]amino]-3-pyridinecarboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC=CN2C(NC=2C(=CC=CN=2)C(N)=O)=N1 JWQOJVOKBAAAAR-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- LQKRMOCYDBDTRR-UHFFFAOYSA-N 7-[3-methoxy-4-[2-methoxyethyl(methyl)amino]phenyl]-n-(4-methoxyphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1=C(OC)C(N(C)CCOC)=CC=C1C1=CC2=NC=CN2C(NC=2C=CC(OC)=CC=2)=N1 LQKRMOCYDBDTRR-UHFFFAOYSA-N 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 235000002639 sodium chloride Nutrition 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 108010067755 dinitrophenyl-bovine serum albumin Proteins 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 238000012746 preparative thin layer chromatography Methods 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- RTLZBGMPMJLEIK-UHFFFAOYSA-N 5-chloro-7-(3,4-dimethoxyphenyl)imidazo[1,2-c]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC=CN2C(Cl)=N1 RTLZBGMPMJLEIK-UHFFFAOYSA-N 0.000 description 5
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 229960003699 evans blue Drugs 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
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- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Transplantation (AREA)
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- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000128870A JP2001302667A (ja) | 2000-04-28 | 2000-04-28 | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
PCT/EP2001/004357 WO2001083485A1 (en) | 2000-04-28 | 2001-04-17 | Imidazopyrimidine derivatives and triazolopyrimidine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20020943A2 true HRP20020943A2 (en) | 2005-02-28 |
Family
ID=18638240
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20020943A HRP20020943A2 (en) | 2000-04-28 | 2002-11-28 | Imidazopyrimidine derivatives and triazolopyrimidine derivatives |
Country Status (38)
Country | Link |
---|---|
US (1) | US6911443B2 (ru) |
EP (1) | EP1278750B1 (ru) |
JP (2) | JP2001302667A (ru) |
KR (1) | KR20030009456A (ru) |
CN (1) | CN1263756C (ru) |
AR (1) | AR033367A1 (ru) |
AT (1) | ATE272639T1 (ru) |
AU (1) | AU783043B2 (ru) |
BG (1) | BG107166A (ru) |
BR (1) | BR0110404A (ru) |
CA (1) | CA2407531A1 (ru) |
CZ (1) | CZ20023551A3 (ru) |
DE (1) | DE60104671T2 (ru) |
DK (1) | DK1278750T3 (ru) |
DO (1) | DOP2001000151A (ru) |
EE (1) | EE200200606A (ru) |
ES (1) | ES2225546T3 (ru) |
HK (1) | HK1058362A1 (ru) |
HR (1) | HRP20020943A2 (ru) |
HU (1) | HUP0300846A2 (ru) |
IL (1) | IL151919A0 (ru) |
MA (1) | MA25746A1 (ru) |
MX (1) | MXPA02010579A (ru) |
MY (1) | MY141578A (ru) |
NO (1) | NO20025154L (ru) |
NZ (2) | NZ522241A (ru) |
PE (1) | PE20011287A1 (ru) |
PL (1) | PL358106A1 (ru) |
PT (1) | PT1278750E (ru) |
RU (1) | RU2306313C2 (ru) |
SI (1) | SI1278750T1 (ru) |
SK (1) | SK15332002A3 (ru) |
SV (1) | SV2001000416A (ru) |
TR (1) | TR200402300T4 (ru) |
TW (1) | TWI222974B (ru) |
UA (1) | UA72615C2 (ru) |
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