JP2018516916A5 - - Google Patents
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- Publication number
- JP2018516916A5 JP2018516916A5 JP2017561798A JP2017561798A JP2018516916A5 JP 2018516916 A5 JP2018516916 A5 JP 2018516916A5 JP 2017561798 A JP2017561798 A JP 2017561798A JP 2017561798 A JP2017561798 A JP 2017561798A JP 2018516916 A5 JP2018516916 A5 JP 2018516916A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- group
- aryl
- heteroaryl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 99
- 125000002947 alkylene group Chemical group 0.000 claims 52
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000005275 alkylenearyl group Chemical group 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- -1 Q is a bond Chemical group 0.000 claims 6
- 125000000539 amino acid group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 239000004475 Arginine Substances 0.000 claims 4
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 4
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 4
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 4
- 239000004472 Lysine Substances 0.000 claims 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 4
- 239000004473 Threonine Substances 0.000 claims 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 4
- 229960003767 alanine Drugs 0.000 claims 4
- 235000004279 alanine Nutrition 0.000 claims 4
- 229960003121 arginine Drugs 0.000 claims 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 4
- 235000009697 arginine Nutrition 0.000 claims 4
- 229960001230 asparagine Drugs 0.000 claims 4
- 235000009582 asparagine Nutrition 0.000 claims 4
- 229960005261 aspartic acid Drugs 0.000 claims 4
- 235000003704 aspartic acid Nutrition 0.000 claims 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 4
- 229960002989 glutamic acid Drugs 0.000 claims 4
- 235000013922 glutamic acid Nutrition 0.000 claims 4
- 239000004220 glutamic acid Substances 0.000 claims 4
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 4
- 235000004554 glutamine Nutrition 0.000 claims 4
- 229960002743 glutamine Drugs 0.000 claims 4
- 229960002449 glycine Drugs 0.000 claims 4
- 229960002885 histidine Drugs 0.000 claims 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 4
- 229960000310 isoleucine Drugs 0.000 claims 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 4
- 229960003136 leucine Drugs 0.000 claims 4
- 229960003646 lysine Drugs 0.000 claims 4
- 229930182817 methionine Natural products 0.000 claims 4
- 229960004452 methionine Drugs 0.000 claims 4
- 229960005190 phenylalanine Drugs 0.000 claims 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 4
- 229960002429 proline Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 229960002898 threonine Drugs 0.000 claims 4
- 229960004799 tryptophan Drugs 0.000 claims 4
- 229960004441 tyrosine Drugs 0.000 claims 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 3
- 229960002433 cysteine Drugs 0.000 claims 3
- 235000018417 cysteine Nutrition 0.000 claims 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003512 tertiary amines Chemical class 0.000 claims 3
- 229960004295 valine Drugs 0.000 claims 3
- 239000004474 valine Substances 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 238000003419 tautomerization reaction Methods 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- XQFGVGNRDPFKFJ-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydropyrrolo[1,2-b]pyridazine Chemical compound N1CCC=C2CCCN21 XQFGVGNRDPFKFJ-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 150000004982 aromatic amines Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000005499 phosphonyl group Chemical group 0.000 claims 1
- 230000035790 physiological processes and functions Effects 0.000 claims 1
- 150000003138 primary alcohols Chemical class 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 0 C*c1ccnc(CC2(CC3CC[C@]4OC5=O)O[C@]34C5=C[C@]2C)c1 Chemical compound C*c1ccnc(CC2(CC3CC[C@]4OC5=O)O[C@]34C5=C[C@]2C)c1 0.000 description 4
- RGTVNADQSHPTRU-IJYMSRKNSA-N C[C@@H](C(Cc(cn1)ccc1Oc1ccccc1)(CC1CC2)O[C@@]11[C@@H]2O2)C=C1C2=O Chemical compound C[C@@H](C(Cc(cn1)ccc1Oc1ccccc1)(CC1CC2)O[C@@]11[C@@H]2O2)C=C1C2=O RGTVNADQSHPTRU-IJYMSRKNSA-N 0.000 description 2
- AZFWUFUXWJXIKY-KTTVAURDSA-N C[C@@H](CC(CC[C@H]1O2)[C@@]11OCCc3cccnc3)C=C1C2=O Chemical compound C[C@@H](CC(CC[C@H]1O2)[C@@]11OCCc3cccnc3)C=C1C2=O AZFWUFUXWJXIKY-KTTVAURDSA-N 0.000 description 2
- RGESCGWQKDVRFM-DNALADSKSA-N C[C@@H](CC(CC[C@H]1O2)[C@@]11OCc3ccncc3)C=C1C2=O Chemical compound C[C@@H](CC(CC[C@H]1O2)[C@@]11OCc3ccncc3)C=C1C2=O RGESCGWQKDVRFM-DNALADSKSA-N 0.000 description 2
- HQMDYTULFZHAJW-KAYCLVBNSA-N C[C@@H](C(Cc1ccc(C)nc1)(CC1CC2)O[C@@]11[C@@H]2O2)C=C1C2=O Chemical compound C[C@@H](C(Cc1ccc(C)nc1)(CC1CC2)O[C@@]11[C@@H]2O2)C=C1C2=O HQMDYTULFZHAJW-KAYCLVBNSA-N 0.000 description 1
- BOEBDVZXGXIZKS-PTUCSGOHSA-N C[C@@H](C(Cc1nc(C(OC)=O)ccc1)(CC1CC2)O[C@@]11[C@@H]2O2)C=C1C2=O Chemical compound C[C@@H](C(Cc1nc(C(OC)=O)ccc1)(CC1CC2)O[C@@]11[C@@H]2O2)C=C1C2=O BOEBDVZXGXIZKS-PTUCSGOHSA-N 0.000 description 1
- FPKSOGQJVONJOY-PMULOELESA-N C[C@@H](CC(CC1[C@H]2C1)[C@@]21OCc2cnc(C)cc2)C=C1C(O)=O Chemical compound C[C@@H](CC(CC1[C@H]2C1)[C@@]21OCc2cnc(C)cc2)C=C1C(O)=O FPKSOGQJVONJOY-PMULOELESA-N 0.000 description 1
- OFFXCVBBCBWDPM-LSLAGHHWSA-N C[C@@H](CC(CC[C@H]1O2)[C@@]11OCc3cnc(C)cn3)C=C1C2=O Chemical compound C[C@@H](CC(CC[C@H]1O2)[C@@]11OCc3cnc(C)cn3)C=C1C2=O OFFXCVBBCBWDPM-LSLAGHHWSA-N 0.000 description 1
- GUSGTKSAELAREW-UGLAOINNSA-N C[C@@H](CC(CC[C@H]1O2)[C@@]11OCc3nc(C(OC)=O)ccc3)C=C1C2=O Chemical compound C[C@@H](CC(CC[C@H]1O2)[C@@]11OCc3nc(C(OC)=O)ccc3)C=C1C2=O GUSGTKSAELAREW-UGLAOINNSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1550735-3 | 2015-06-05 | ||
| SE1550735A SE539204C2 (en) | 2015-06-05 | 2015-06-05 | Ether analogues of galiellalactone |
| PCT/EP2016/062437 WO2016193332A1 (en) | 2015-06-05 | 2016-06-02 | Ether analogues of galiellalactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018516916A JP2018516916A (ja) | 2018-06-28 |
| JP2018516916A5 true JP2018516916A5 (https=) | 2019-07-04 |
Family
ID=56096638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017561798A Pending JP2018516916A (ja) | 2015-06-05 | 2016-06-02 | ガリエララクトンのエーテル類似体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10351577B2 (https=) |
| EP (1) | EP3303313A1 (https=) |
| JP (1) | JP2018516916A (https=) |
| KR (1) | KR20180021783A (https=) |
| SE (1) | SE539204C2 (https=) |
| WO (1) | WO2016193332A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10077246B2 (en) * | 2014-03-07 | 2018-09-18 | Glactone Pharma Development Ab | Tricyclic prodrugs |
| SE540295C2 (en) | 2016-12-05 | 2018-05-29 | Glactone Pharma Dev Ab | Sulfonamide analogues of galiellalactone |
| CN120574283A (zh) | 2019-04-05 | 2025-09-02 | 凯麦拉医疗公司 | Stat降解剂和其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001272490A1 (en) | 2000-07-03 | 2002-01-14 | ibwf Institut fur Biotechnologie und Wirkstoff-Forschung e.V. | Use of galiella lactone |
| US9150531B2 (en) | 2010-07-19 | 2015-10-06 | Glactone Pharma Development Ab | Tricyclic lactones for treatment of cancer |
| US10077246B2 (en) * | 2014-03-07 | 2018-09-18 | Glactone Pharma Development Ab | Tricyclic prodrugs |
-
2015
- 2015-06-05 SE SE1550735A patent/SE539204C2/en not_active IP Right Cessation
-
2016
- 2016-06-02 US US15/578,589 patent/US10351577B2/en not_active Expired - Fee Related
- 2016-06-02 EP EP16726324.3A patent/EP3303313A1/en not_active Withdrawn
- 2016-06-02 WO PCT/EP2016/062437 patent/WO2016193332A1/en not_active Ceased
- 2016-06-02 JP JP2017561798A patent/JP2018516916A/ja active Pending
- 2016-06-02 KR KR1020187000329A patent/KR20180021783A/ko not_active Withdrawn
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