UA79444C2 - 2-(піридин-2-іламіно)піридо[2,3-d]піримідин-7-они - Google Patents

Info

Publication number

UA79444C2

UA79444C2 UA20040706104A UA20040706104A UA79444C2 UA 79444 C2 UA79444 C2 UA 79444C2 UA 20040706104 A UA20040706104 A UA 20040706104A UA 20040706104 A UA20040706104 A UA 20040706104A UA 79444 C2 UA79444 C2 UA 79444C2

Authority

UA

Ukraine

Prior art keywords

ylamino

cyclopentyl

pyrido

pyrimidin

pyridin

Prior art date

2002-01-22

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 120
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 121
• -1 aminoalkylcarbonyl Chemical group 0.000 claims description 103
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 98
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 150000003839 salts Chemical group 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 23
• 150000002148 esters Chemical group 0.000 claims description 22
• 206010028980 Neoplasm Diseases 0.000 claims description 21
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 21
• 150000002431 hydrogen Chemical class 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 201000011510 cancer Diseases 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000002837 carbocyclic group Chemical group 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 239000001301 oxygen Substances 0.000 claims description 14
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 150000002825 nitriles Chemical class 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 239000011593 sulfur Chemical group 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 230000035755 proliferation Effects 0.000 claims description 10
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 241000282414 Homo sapiens Species 0.000 claims description 8
• 150000001408 amides Chemical group 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• 230000004663 cell proliferation Effects 0.000 claims description 8
• 125000004494 ethyl ester group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
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• 125000000304 alkynyl group Chemical group 0.000 claims description 6
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• 230000002159 abnormal effect Effects 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
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• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
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• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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• 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
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• XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 3
• 206010023347 Keratoacanthoma Diseases 0.000 claims description 3
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• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 201000010208 Seminoma Diseases 0.000 claims description 3
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• 206010057469 Vascular stenosis Diseases 0.000 claims description 3
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• 150000001450 anions Chemical class 0.000 claims description 3
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• 210000000988 bone and bone Anatomy 0.000 claims description 3
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• 210000003169 central nervous system Anatomy 0.000 claims description 3
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• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims description 3
• 210000002105 tongue Anatomy 0.000 claims description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 3
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• QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 claims description 2
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• 201000010881 cervical cancer Diseases 0.000 claims description 2
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001188 haloalkyl group Chemical group 0.000 claims 3
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• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
• TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 1
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