RU2344123C9 - 3,4-дизамещенные циклобутен-1,2-дионы как лиганды схс-хемокинового рецептора - Google Patents
3,4-дизамещенные циклобутен-1,2-дионы как лиганды схс-хемокинового рецептора Download PDFInfo
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- RU2344123C9 RU2344123C9 RU2003133448/04A RU2003133448A RU2344123C9 RU 2344123 C9 RU2344123 C9 RU 2344123C9 RU 2003133448/04 A RU2003133448/04 A RU 2003133448/04A RU 2003133448 A RU2003133448 A RU 2003133448A RU 2344123 C9 RU2344123 C9 RU 2344123C9
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- -1 3,4-disubstituted cyclobutene-1,2-diones Chemical class 0.000 title claims 5
- 239000003446 ligand Substances 0.000 title claims 2
- 108091008928 CXC chemokine receptors Proteins 0.000 title 1
- 102000054900 CXCR Receptors Human genes 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 239000012453 solvate Substances 0.000 claims abstract 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract 5
- 201000011510 cancer Diseases 0.000 claims abstract 5
- 201000010099 disease Diseases 0.000 claims abstract 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 5
- 239000003814 drug Substances 0.000 claims abstract 5
- 230000001404 mediated effect Effects 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 55
- 150000001875 compounds Chemical class 0.000 claims 54
- 125000001072 heteroaryl group Chemical group 0.000 claims 39
- 125000001424 substituent group Chemical group 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000003107 substituted aryl group Chemical group 0.000 claims 17
- 125000004432 carbon atom Chemical group C* 0.000 claims 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010040070 Septic Shock Diseases 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 claims 1
- 108050006947 CXC Chemokine Proteins 0.000 claims 1
- 102000019388 CXC chemokine Human genes 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010014824 Endotoxic shock Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 108010018951 Interleukin-8B Receptors Proteins 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 125000005038 alkynylalkyl group Chemical group 0.000 claims 1
- 208000030961 allergic reaction Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000003388 anti-hormonal effect Effects 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 229930014626 natural product Natural products 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000005750 substituted cyclic group Chemical group 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 102000019034 Chemokines Human genes 0.000 abstract 2
- 108010012236 Chemokines Proteins 0.000 abstract 2
- 230000001154 acute effect Effects 0.000 abstract 2
- 208000037976 chronic inflammation Diseases 0.000 abstract 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 CC(*)(*)*=CSC=CN Chemical compound CC(*)(*)*=CSC=CN 0.000 description 21
- MXXPDAXFPXOUBG-UHFFFAOYSA-O CC(C)C(C)C(C)[NH3+] Chemical compound CC(C)C(C)C(C)[NH3+] MXXPDAXFPXOUBG-UHFFFAOYSA-O 0.000 description 1
- LLEOJEJGAJNCLX-UHFFFAOYSA-N CCC(C)NC(C(C1=O)=O)=C1Nc(cccc1C(N(C)C)=O)c1O Chemical compound CCC(C)NC(C(C1=O)=O)=C1Nc(cccc1C(N(C)C)=O)c1O LLEOJEJGAJNCLX-UHFFFAOYSA-N 0.000 description 1
- YZNQZONEXPPIBE-QMMMGPOBSA-N CC[C@H](C(F)(F)F)c1cc(CC)c[o]1 Chemical compound CC[C@H](C(F)(F)F)c1cc(CC)c[o]1 YZNQZONEXPPIBE-QMMMGPOBSA-N 0.000 description 1
- LLEOJEJGAJNCLX-VIFPVBQESA-N CC[C@H](C)NC(C(C1=O)=O)=C1Nc(cccc1C(N(C)C)=O)c1O Chemical compound CC[C@H](C)NC(C(C1=O)=O)=C1Nc(cccc1C(N(C)C)=O)c1O LLEOJEJGAJNCLX-VIFPVBQESA-N 0.000 description 1
- JGGJMYCQINJGFS-NKWVEPMBSA-N CC[C@](C(C)C)(P)[IH][C@@H](N)I Chemical compound CC[C@](C(C)C)(P)[IH][C@@H](N)I JGGJMYCQINJGFS-NKWVEPMBSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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| RU2784831C2 (ru) * | 2018-09-21 | 2022-11-30 | Пфайзер Инк. | N-замещенные диоксоциклобутениламино-3-гидроксипиколинамиды, пригодные в качестве ингибиторов ccr6 |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000035855A1 (en) * | 1998-12-14 | 2000-06-22 | American Home Products Corporation | 3,4-diamino-3-cyclobutene-1,2-dione derivatives which inhibit leukocyte adhesion mediated by vla-4 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2784831C2 (ru) * | 2018-09-21 | 2022-11-30 | Пфайзер Инк. | N-замещенные диоксоциклобутениламино-3-гидроксипиколинамиды, пригодные в качестве ингибиторов ccr6 |
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