CA3034108A1 - Cxcr3 receptor agonists - Google Patents
Cxcr3 receptor agonists Download PDFInfo
- Publication number
- CA3034108A1 CA3034108A1 CA3034108A CA3034108A CA3034108A1 CA 3034108 A1 CA3034108 A1 CA 3034108A1 CA 3034108 A CA3034108 A CA 3034108A CA 3034108 A CA3034108 A CA 3034108A CA 3034108 A1 CA3034108 A1 CA 3034108A1
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- Prior art keywords
- compound
- groups
- substituted
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- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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- 108010061300 CXCR3 Receptors Proteins 0.000 title claims description 17
- 102000011963 CXCR3 Receptors Human genes 0.000 title claims description 17
- 239000000018 receptor agonist Substances 0.000 title description 5
- 229940044601 receptor agonist Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 346
- 238000000034 method Methods 0.000 claims abstract description 290
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- 125000000217 alkyl group Chemical group 0.000 claims description 67
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- 239000001257 hydrogen Substances 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 41
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- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 30
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
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- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 claims description 20
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
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- 125000005842 heteroatom Chemical group 0.000 description 21
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- 125000004432 carbon atom Chemical group C* 0.000 description 20
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- 239000012458 free base Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005252 haloacyl group Chemical group 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003427 indacenyl group Chemical group 0.000 description 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 230000032297 kinesis Effects 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- WLHQHAUOOXYABV-UHFFFAOYSA-N lornoxicam Chemical compound OC=1C=2SC(Cl)=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 WLHQHAUOOXYABV-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- VWHRYODZTDMVSS-QMMMGPOBSA-N m-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(F)=C1 VWHRYODZTDMVSS-QMMMGPOBSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- KPGAZEIMLGRWIJ-MHWRWJLKSA-N methyl (E)-3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-bicyclo[1.1.1]pentanyl]-2-(phenylmethoxycarbonylamino)prop-2-enoate Chemical compound C(C1=CC=CC=C1)OC(=O)N\C(\C(=O)OC)=C\C12CC(C1)(C2)NC(=O)OC(C)(C)C KPGAZEIMLGRWIJ-MHWRWJLKSA-N 0.000 description 1
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical compound COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
- LJHAPRKTPAREGO-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate Chemical compound COC(=O)C(P(=O)(OC)OC)NC(=O)OC(C)(C)C LJHAPRKTPAREGO-UHFFFAOYSA-N 0.000 description 1
- JVAIEVPSFRDEMD-UHFFFAOYSA-N methyl 4-[3-(dimethylamino)oxetan-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound C(C)(C)(C)OC(=O)NC(C(=O)OC)CCC1(COC1)N(C)C JVAIEVPSFRDEMD-UHFFFAOYSA-N 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
- ZSJWOKQVYZTDOA-UHFFFAOYSA-N n-(6-bromo-2,3-dihydro-1,4-benzodioxin-7-yl)acetamide Chemical compound O1CCOC2=C1C=C(NC(=O)C)C(Br)=C2 ZSJWOKQVYZTDOA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
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- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 230000006920 protein precipitation Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- DUXCJSDVIOQNAS-VWLOTQADSA-N tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(4-hydroxypiperidin-1-yl)butanoate Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@H](C(=O)OC(C)(C)C)CCN1CCC(CC1)O DUXCJSDVIOQNAS-VWLOTQADSA-N 0.000 description 1
- KRSUDBIZXKOKGA-UHFFFAOYSA-N tert-butyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate Chemical compound C1=CC=C2CNC(C(=O)OC(C)(C)C)CC2=C1 KRSUDBIZXKOKGA-UHFFFAOYSA-N 0.000 description 1
- QEPAEPGSGDGWPV-UHFFFAOYSA-N tert-butyl 2-amino-4-(4-hydroxypiperidin-1-yl)butanoate Chemical compound NC(C(=O)OC(C)(C)C)CCN1CCC(CC1)O QEPAEPGSGDGWPV-UHFFFAOYSA-N 0.000 description 1
- PGLXPBCSIUOBMU-UHFFFAOYSA-N tert-butyl N-(3,4-dichloro-2-methoxyphenyl)carbamate Chemical compound ClC=1C(=C(C=CC=1Cl)NC(OC(C)(C)C)=O)OC PGLXPBCSIUOBMU-UHFFFAOYSA-N 0.000 description 1
- XASIVVFKDRTJED-ZDUSSCGKSA-N tert-butyl N-[(2S)-1-(4-chloro-3-methylanilino)-4-hydroxy-1-oxobutan-2-yl]carbamate Chemical compound ClC1=C(C=C(C=C1)NC([C@H](CCO)NC(OC(C)(C)C)=O)=O)C XASIVVFKDRTJED-ZDUSSCGKSA-N 0.000 description 1
- GGNZZMOZNFZCOK-ZDUSSCGKSA-N tert-butyl N-[(2S)-5-(carbamoylamino)-1-(3,4-dichloroanilino)-1-oxopentan-2-yl]carbamate Chemical compound ClC=1C=C(C=CC=1Cl)NC([C@H](CCCNC(=O)N)NC(OC(C)(C)C)=O)=O GGNZZMOZNFZCOK-ZDUSSCGKSA-N 0.000 description 1
- HLYQLFXANLAVDG-VIFPVBQESA-N tert-butyl N-[(3S)-3-amino-4-(3,4-dichloro-2-fluoroanilino)-4-oxobutyl]carbamate Chemical compound N[C@@H](CCNC(OC(C)(C)C)=O)C(=O)NC1=C(C(=C(C=C1)Cl)Cl)F HLYQLFXANLAVDG-VIFPVBQESA-N 0.000 description 1
- YIJILICFLWXVAV-ZDUSSCGKSA-N tert-butyl N-[(3S)-3-amino-4-(4-chloro-3-methylanilino)-4-oxobutyl]carbamate Chemical compound N[C@@H](CCNC(OC(C)(C)C)=O)C(=O)NC1=CC(=C(C=C1)Cl)C YIJILICFLWXVAV-ZDUSSCGKSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- GQMVAUFIUVHMBB-UHFFFAOYSA-K trinaphthalen-2-yloxybismuthane Chemical compound C1=CC=CC2=CC(O[Bi](OC=3C=C4C=CC=CC4=CC=3)OC=3C=C4C=CC=CC4=CC=3)=CC=C21 GQMVAUFIUVHMBB-UHFFFAOYSA-K 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662383202P | 2016-09-02 | 2016-09-02 | |
| US62/383,202 | 2016-09-02 | ||
| US201762478496P | 2017-03-29 | 2017-03-29 | |
| US62/478,496 | 2017-03-29 | ||
| PCT/US2017/049768 WO2018045246A1 (en) | 2016-09-02 | 2017-08-31 | Cxcr3 receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3034108A1 true CA3034108A1 (en) | 2018-03-08 |
Family
ID=59846729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3034108A Abandoned CA3034108A1 (en) | 2016-09-02 | 2017-08-31 | Cxcr3 receptor agonists |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20190345133A1 (OSRAM) |
| EP (1) | EP3507275B1 (OSRAM) |
| JP (1) | JP7181857B2 (OSRAM) |
| AU (1) | AU2017318674B2 (OSRAM) |
| CA (1) | CA3034108A1 (OSRAM) |
| ES (1) | ES2950560T3 (OSRAM) |
| MX (1) | MX380217B (OSRAM) |
| WO (1) | WO2018045246A1 (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021163272A2 (en) | 2020-02-12 | 2021-08-19 | The Regents Of The University Of California | Platelet factors and cognitive improvement |
| CN111943823A (zh) * | 2020-09-16 | 2020-11-17 | 安徽工业大学 | 一种苯菌酮的制备方法 |
| CN116178383B (zh) * | 2022-12-26 | 2025-04-22 | 南方科技大学 | 生物碱及三价铁卟啉催化合成生物碱的方法 |
-
2017
- 2017-08-31 AU AU2017318674A patent/AU2017318674B2/en not_active Ceased
- 2017-08-31 MX MX2019002166A patent/MX380217B/es unknown
- 2017-08-31 WO PCT/US2017/049768 patent/WO2018045246A1/en not_active Ceased
- 2017-08-31 ES ES17765033T patent/ES2950560T3/es active Active
- 2017-08-31 CA CA3034108A patent/CA3034108A1/en not_active Abandoned
- 2017-08-31 EP EP17765033.0A patent/EP3507275B1/en active Active
- 2017-08-31 US US16/335,641 patent/US20190345133A1/en not_active Abandoned
- 2017-08-31 JP JP2019512307A patent/JP7181857B2/ja active Active
-
2020
- 2020-05-11 US US16/872,161 patent/US11040954B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2950560T3 (es) | 2023-10-11 |
| US11040954B1 (en) | 2021-06-22 |
| MX380217B (es) | 2025-03-12 |
| AU2017318674B2 (en) | 2020-11-12 |
| EP3507275A1 (en) | 2019-07-10 |
| AU2017318674A1 (en) | 2019-03-28 |
| JP7181857B2 (ja) | 2022-12-01 |
| EP3507275B1 (en) | 2023-04-26 |
| MX2019002166A (es) | 2019-06-12 |
| US20190345133A1 (en) | 2019-11-14 |
| JP2019533639A (ja) | 2019-11-21 |
| WO2018045246A1 (en) | 2018-03-08 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20231212 |