UA72615C2 - Imidazopyrimidine and triazolopyrimidine derivatives, a method for the preparation thereof, medicament based thereon - Google Patents

Info

Publication number

UA72615C2

UA72615C2 UA2002119418A UA2002119418A UA72615C2 UA 72615 C2 UA72615 C2 UA 72615C2 UA 2002119418 A UA2002119418 A UA 2002119418A UA 2002119418 A UA2002119418 A UA 2002119418A UA 72615 C2 UA72615 C2 UA 72615C2

Authority

UA

Ukraine

Prior art keywords

alkyl

substituent

group

optionally containing

optionally

Prior art date

2000-04-28

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• 238000000034 method Methods 0.000 title claims description 32
• 239000003814 drug Substances 0.000 title description 7
• 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
• 238000002360 preparation method Methods 0.000 title description 5
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 98
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 14
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• 125000001424 substituent group Chemical group 0.000 claims description 205
• -1 morpholino, piperidino Chemical group 0.000 claims description 107
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 82
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 57
• 125000003277 amino group Chemical group 0.000 claims description 49
• 125000004429 atom Chemical group 0.000 claims description 41
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 35
• 230000000694 effects Effects 0.000 claims description 31
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 26
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000001544 thienyl group Chemical group 0.000 claims description 17
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 15
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 15
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 12
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 125000002883 imidazolyl 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
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 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
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
• 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 8
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 7
• 206010020751 Hypersensitivity Diseases 0.000 claims description 6
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 6
• 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 6
• 125000004464 hydroxyphenyl group Chemical class 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000006501 nitrophenyl group Chemical class 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 208000026935 allergic disease Diseases 0.000 claims description 5
• 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 239000011570 nicotinamide Substances 0.000 claims description 5
• 229960003966 nicotinamide Drugs 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
• 201000010105 allergic rhinitis Diseases 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 201000008937 atopic dermatitis Diseases 0.000 claims description 4
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 4
• 125000000956 methoxy group Chemical class [H]C([H])([H])O* 0.000 claims description 4
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical class [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
• 235000005152 nicotinamide Nutrition 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 230000003993 interaction Effects 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 206010010741 Conjunctivitis Diseases 0.000 claims description 2
• 208000004262 Food Hypersensitivity Diseases 0.000 claims description 2
• 206010016946 Food allergy Diseases 0.000 claims description 2
• 208000024780 Urticaria Diseases 0.000 claims description 2
• 230000007815 allergy Effects 0.000 claims description 2
• 235000020932 food allergy Nutrition 0.000 claims description 2
• 230000028993 immune response Effects 0.000 claims description 2
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
• CKIIJIDEWWXQEA-UHFFFAOYSA-N 2-(bromomethyl)-1,3-dioxolane Chemical compound BrCC1OCCO1 CKIIJIDEWWXQEA-UHFFFAOYSA-N 0.000 claims 2
• 229940126601 medicinal product Drugs 0.000 claims 2
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 2
• 150000003230 pyrimidines Chemical class 0.000 claims 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
• 206010037660 Pyrexia Diseases 0.000 claims 1
• 230000015271 coagulation Effects 0.000 claims 1
• 238000005345 coagulation Methods 0.000 claims 1
• 239000000555 dodecyl gallate Substances 0.000 claims 1
• 239000012442 inert solvent Substances 0.000 claims 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
• 201000009240 nasopharyngitis Diseases 0.000 claims 1
• NOOLISFMXDJSKH-UHFFFAOYSA-N p-menthan-3-ol Chemical compound CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-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
• 229910052717 sulfur Inorganic materials 0.000 abstract description 2
• 230000003266 anti-allergic effect Effects 0.000 abstract 1
• 125000002837 carbocyclic group Chemical group 0.000 abstract 1
• 229910052757 nitrogen Inorganic materials 0.000 description 76
• 239000000203 mixture Substances 0.000 description 62
• 229910052740 iodine Inorganic materials 0.000 description 56
• 239000000243 solution Substances 0.000 description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 33
• 235000002639 sodium chloride Nutrition 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 26
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• 238000001990 intravenous administration Methods 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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