BG107166A - Имидазопиримидинови производни и триазолопиримидинови производни - Google Patents

Имидазопиримидинови производни и триазолопиримидинови производни Download PDF

Info

Publication number: BG107166A
Authority: BG; Bulgaria
Prior art keywords: alkyl; optionally substituted; amino; group; carbonyl
Prior art date: 2000-04-28

Application number

BG107166A

Other languages

Bulgarian (bg)

English (en)

Inventor

Takeshi Yura

Arnel Concepcion

Gyoonhee Han

Makiko Hiraoka

Hiroko Katsumata

Norihiro Kawamura

Toshio Kokubo

Hiroshi Komura

Yingfu Li

Timothy Lowinger

Muneto Mogi

Noriyuki Yamamoto

Nagahiro Yoshida

Scott Miller

Margaret Popp

Aniko Redmann

Martha Rodriguez

William Scott

Ming Wang

Original Assignee

Bayer Aktiengesellschaft

Priority date (The priority date 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 date listed.)

2000-04-28

Filing date

2002-10-03

Publication date

2003-06-30

2002-10-03 Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft

2003-06-30 Publication of BG107166A publication Critical patent/BG107166A/bg

Links

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 8
150000005237 imidazopyrimidines Chemical class 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 105
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 30
229910052717 sulfur Inorganic materials 0.000 claims abstract description 26
229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 111
-1 morpholino, piperidino Chemical group 0.000 claims description 110
239000001257 hydrogen Substances 0.000 claims description 86
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 81
229910052736 halogen Inorganic materials 0.000 claims description 80
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
150000002367 halogens Chemical class 0.000 claims description 62
125000000217 alkyl group Chemical group 0.000 claims description 57
239000000203 mixture Substances 0.000 claims description 55
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
150000002431 hydrogen Chemical group 0.000 claims description 43
150000003839 salts Chemical class 0.000 claims description 39
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
125000003277 amino group Chemical group 0.000 claims description 37
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
238000000034 method Methods 0.000 claims description 35
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 32
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 27
RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical group FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 claims description 26
230000000694 effects Effects 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
125000005842 heteroatom Chemical group 0.000 claims description 25
125000004093 cyano group Chemical group *C#N 0.000 claims description 24
125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 22
125000003831 tetrazolyl group Chemical group 0.000 claims description 21
WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical group FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 claims description 20
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 19
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims description 15
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
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 claims description 14
102000000551 Syk Kinase Human genes 0.000 claims description 14
108010016672 Syk Kinase Proteins 0.000 claims description 14
125000001544 thienyl group Chemical group 0.000 claims description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
229940079593 drug Drugs 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 10
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 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
208000026935 allergic disease Diseases 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
208000010668 atopic eczema Diseases 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000001301 oxygen Chemical group 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
206010020751 Hypersensitivity Diseases 0.000 claims description 6
125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 6
125000005879 dioxolanyl group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 6
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
108091000080 Phosphotransferase Proteins 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
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
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
229960003966 nicotinamide Drugs 0.000 claims description 5
239000011570 nicotinamide Substances 0.000 claims description 5
125000006501 nitrophenyl group Chemical group 0.000 claims description 5
102000020233 phosphotransferase Human genes 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
125000003003 spiro 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
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
206010012434 Dermatitis allergic Diseases 0.000 claims description 4
201000008937 atopic dermatitis Diseases 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
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 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
206010010741 Conjunctivitis Diseases 0.000 claims description 3
208000004262 Food Hypersensitivity Diseases 0.000 claims description 3
206010016946 Food allergy Diseases 0.000 claims description 3
206010028980 Neoplasm Diseases 0.000 claims description 3
208000024780 Urticaria Diseases 0.000 claims description 3
230000007815 allergy Effects 0.000 claims description 3
235000020932 food allergy Nutrition 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims description 3
208000018464 vernal keratoconjunctivitis Diseases 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
230000006806 disease prevention Effects 0.000 claims description 2
230000028993 immune response Effects 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
229960005235 piperonyl butoxide Drugs 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
125000005843 halogen group Chemical group 0.000 claims 16
230000002265 prevention Effects 0.000 claims 3
KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims 2
230000015271 coagulation Effects 0.000 claims 2
238000005345 coagulation Methods 0.000 claims 2
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 1
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 1
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 1
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 1
RTUGJUAFUCATPS-UHFFFAOYSA-N 7-(3-methoxy-4-morpholin-4-ylphenyl)-n-(2-methylsulfonylphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound COC1=CC(C=2N=C(NC=3C(=CC=CC=3)S(C)(=O)=O)N3C=CN=C3C=2)=CC=C1N1CCOCC1 RTUGJUAFUCATPS-UHFFFAOYSA-N 0.000 claims 1
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 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
241000189658 Piano group Species 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
235000009508 confectionery Nutrition 0.000 claims 1
229960003444 immunosuppressant agent Drugs 0.000 claims 1
230000001861 immunosuppressant effect Effects 0.000 claims 1
239000003018 immunosuppressive agent Substances 0.000 claims 1
125000001041 indolyl group Chemical group 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 abstract description 4
125000003107 substituted aryl group Chemical group 0.000 abstract description 4
125000003118 aryl group Chemical group 0.000 abstract description 3
230000003266 anti-allergic effect Effects 0.000 abstract 1
125000002837 carbocyclic group Chemical group 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 321
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 62
239000000243 solution Substances 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000005481 NMR spectroscopy Methods 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
239000007787 solid Substances 0.000 description 14
239000002585 base Substances 0.000 description 13
239000012044 organic layer Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000012043 crude product Substances 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
241000700159 Rattus Species 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
238000004949 mass spectrometry Methods 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 9
235000019439 ethyl acetate Nutrition 0.000 description 9
239000000725 suspension Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000012267 brine Substances 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
239000005457 ice water Substances 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
239000000284 extract Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 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
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 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
238000007796 conventional method Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000003818 flash chromatography Methods 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
238000005406 washing Methods 0.000 description 5
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 4
QJRWLNLUIAJTAD-UHFFFAOYSA-N 4-hydroxy-3-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC=C1O QJRWLNLUIAJTAD-UHFFFAOYSA-N 0.000 description 4
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 4
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NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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239000004299 sodium benzoate Substances 0.000 description 1
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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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HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications

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- 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
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Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Immunology (AREA)
Pulmonology (AREA)
Dermatology (AREA)
Hematology (AREA)
Diabetes (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Ophthalmology & Optometry (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Orthopedic Medicine & Surgery (AREA)
Otolaryngology (AREA)
Child & Adolescent Psychology (AREA)
Psychiatry (AREA)
Transplantation (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (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)

BG107166A 2000-04-28 2002-10-03 Имидазопиримидинови производни и триазолопиримидинови производни BG107166A (bg)

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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

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US (1)	US6911443B2 (et)
EP (1)	EP1278750B1 (et)
JP (2)	JP2001302667A (et)
KR (1)	KR20030009456A (et)
CN (1)	CN1263756C (et)
AR (1)	AR033367A1 (et)
AT (1)	ATE272639T1 (et)
AU (1)	AU783043B2 (et)
BG (1)	BG107166A (et)
BR (1)	BR0110404A (et)
CA (1)	CA2407531A1 (et)
CZ (1)	CZ20023551A3 (et)
DE (1)	DE60104671T2 (et)
DK (1)	DK1278750T3 (et)
DO (1)	DOP2001000151A (et)
EE (1)	EE200200606A (et)
ES (1)	ES2225546T3 (et)
HR (1)	HRP20020943A2 (et)
HU (1)	HUP0300846A2 (et)
IL (1)	IL151919A0 (et)
MA (1)	MA25746A1 (et)
MX (1)	MXPA02010579A (et)
MY (1)	MY141578A (et)
NO (1)	NO20025154D0 (et)
NZ (2)	NZ522241A (et)
PE (1)	PE20011287A1 (et)
PL (1)	PL358106A1 (et)
PT (1)	PT1278750E (et)
RU (1)	RU2306313C2 (et)
SI (1)	SI1278750T1 (et)
SK (1)	SK15332002A3 (et)
SV (1)	SV2001000416A (et)
TR (1)	TR200402300T4 (et)
TW (1)	TWI222974B (et)
UA (1)	UA72615C2 (et)
WO (1)	WO2001083485A1 (et)
ZA (1)	ZA200207676B (et)

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PT1471057E (pt)	2003-04-25	2006-05-31	Actimis Pharmaceuticals Inc	Derivados de acido pirimidinilacetico uteis para o tratamento de doencas mediadas por crth2
US20070129383A1 (en) *	2003-10-17	2007-06-07	Hiroshi Kuramochi	Substituted 2-amino-[1,2,4]triazolo[1,5-a]pyrimidine derivative and use thereof
WO2005061519A1 (en)	2003-12-19	2005-07-07	Takeda San Diego, Inc.	Kinase inhibitors
ATE433452T1 (de) *	2004-01-31	2009-06-15	Actimis Pharmaceuticals Inc	Imidazoä1,2-cüpyrimidinylessigsäurederivate
JP2008504294A (ja) *	2004-06-25	2008-02-14	アムジエン・インコーポレーテツド	サイトカイン介在疾患および他の疾患の治療において有用な縮合トリアゾールおよびインダゾール
US7550598B2 (en)	2004-08-18	2009-06-23	Takeda Pharmaceutical Company Limited	Kinase inhibitors
BRPI0514549A (pt)	2004-08-23	2008-06-17	Wyeth Corp	ácidos de pirrol-naftila como inibidores de pai-1
WO2006023866A2 (en)	2004-08-23	2006-03-02	Wyeth	Thiazolo-naphthyl acids as inhibitors of plasminogen activator inhibitor-1
JP2008510815A (ja)	2004-08-23	2008-04-10	ワイス	血栓症および心臓血管疾患の治療にて有用な調節剤であるプラスミノゲン活性化因子阻害剤１型（ｐａｉ−１）としてのオキサゾロ−ナフチル酸
ATE479687T1 (de)	2004-10-15	2010-09-15	Takeda Pharmaceutical	Kinaseinhibitoren
WO2006093247A1 (ja)	2005-02-28	2006-09-08	Japan Tobacco Inc.	Ｓｙｋ阻害活性を有する新規なアミノピリジン化合物
US7442700B2 (en)	2005-07-01	2008-10-28	Bristol-Myers Squibb Company	Pyrrolotriazine compounds useful as kinase inhibitors and methods of treating kinase-associated conditions therewith
US8119655B2 (en) *	2005-10-07	2012-02-21	Takeda Pharmaceutical Company Limited	Kinase inhibitors
EA200800664A1 (ru) *	2005-10-13	2009-02-27	Глаксо Груп Лимитед	Производные пирролопиримидина в качестве ингибиторов syk
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AU6220401A (en)	2001-11-12
ZA200207676B (en)	2003-09-25
MA25746A1 (fr)	2003-04-01
EP1278750B1 (en)	2004-08-04
DE60104671D1 (de)	2004-09-09
CA2407531A1 (en)	2001-10-25
CN1263756C (zh)	2006-07-12
JP2003535067A (ja)	2003-11-25
EE200200606A (et)	2004-04-15
HK1058362A1 (en)	2004-05-14
HRP20020943A2 (en)	2005-02-28
BR0110404A (pt)	2003-02-11
ATE272639T1 (de)	2004-08-15
SK15332002A3 (sk)	2003-06-03
MXPA02010579A (es)	2003-05-14
EP1278750A1 (en)	2003-01-29
US6911443B2 (en)	2005-06-28
DE60104671T2 (de)	2005-12-29
AU783043B2 (en)	2005-09-22
DK1278750T3 (da)	2004-11-22
RU2306313C2 (ru)	2007-09-20
KR20030009456A (ko)	2003-01-29
TR200402300T4 (tr)	2004-12-21
SV2001000416A (es)	2001-07-03
CZ20023551A3 (cs)	2003-01-15
PL358106A1 (en)	2004-08-09
MY141578A (en)	2010-05-14
UA72615C2 (en)	2005-03-15
DOP2001000151A (es)	2002-05-15
IL151919A0 (en)	2003-04-10
NZ526221A (en)	2005-01-28
NO20025154L (no)	2002-10-25
NZ522241A (en)	2004-04-30
TWI222974B (en)	2004-11-01
ES2225546T3 (es)	2005-03-16
NO20025154D0 (no)	2002-10-25
PT1278750E (pt)	2004-11-30
JP2001302667A (ja)	2001-10-31
SI1278750T1 (en)	2005-02-28
AR033367A1 (es)	2003-12-17
US20040054179A1 (en)	2004-03-18
WO2001083485A1 (en)	2001-11-08
CN1439009A (zh)	2003-08-27
PE20011287A1 (es)	2002-02-27
HUP0300846A2 (hu)	2003-08-28

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