JP2014517836A5 - - Google Patents
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- JP2014517836A5 JP2014517836A5 JP2014510511A JP2014510511A JP2014517836A5 JP 2014517836 A5 JP2014517836 A5 JP 2014517836A5 JP 2014510511 A JP2014510511 A JP 2014510511A JP 2014510511 A JP2014510511 A JP 2014510511A JP 2014517836 A5 JP2014517836 A5 JP 2014517836A5
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- Prior art keywords
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- compound
- alkyl
- moiety
- compound according
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- 150000001875 compounds Chemical class 0.000 claims description 155
- 238000000034 method Methods 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 24
- -1 -OH Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 239000012069 chiral reagent Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 11
- 229940002612 prodrug Drugs 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 230000008484 agonism Effects 0.000 claims description 5
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 230000002159 abnormal effect Effects 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 206010022000 influenza Diseases 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 0 CC(C)*Oc(c(C#N)c1)ccc1-c1cnc(-c2c(CCC3N)c3ccc2)[s]1 Chemical compound CC(C)*Oc(c(C#N)c1)ccc1-c1cnc(-c2c(CCC3N)c3ccc2)[s]1 0.000 description 16
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 description 13
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 description 13
- 231100001274 therapeutic index Toxicity 0.000 description 8
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 7
- 239000000556 agonist Substances 0.000 description 5
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- 239000003223 protective agent Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical group CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- JRCCMJGRDJTQNS-UHFFFAOYSA-N 1-azido-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(N=[N+]=[N-])CCCC2=C1 JRCCMJGRDJTQNS-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
- ARXZAIZCRNOWGB-UHFFFAOYSA-N CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CCC3)c3ccc2)[s]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CCC3)c3ccc2)[s]1 ARXZAIZCRNOWGB-UHFFFAOYSA-N 0.000 description 2
- IJTATBVIZVMQBT-UHFFFAOYSA-N CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CCC3NCCS=O)c3ccc2)[s]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CCC3NCCS=O)c3ccc2)[s]1 IJTATBVIZVMQBT-UHFFFAOYSA-N 0.000 description 2
- FFUBFQCTDBXZMZ-DEOSSOPVSA-N CC(C)Oc(ccc(-c1ncc(-c2cccc3c2CC[C@@H]3NCC(N2CCCC2)=O)[s]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2cccc3c2CC[C@@H]3NCC(N2CCCC2)=O)[s]1)c1)c1C#N FFUBFQCTDBXZMZ-DEOSSOPVSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 229960001230 asparagine Drugs 0.000 description 2
- 235000009582 asparagine Nutrition 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DQBCRVIBTFHJLM-UHFFFAOYSA-N 2-bromo-1,3,4-thiadiazole Chemical class BrC1=NN=CS1 DQBCRVIBTFHJLM-UHFFFAOYSA-N 0.000 description 1
- RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 1
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 1
- XSZVUKXQDQTDQT-QFIPXVFZSA-N CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CC[C@@H]3NCC(N(C)C)=O)c3ccc2)[s]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CC[C@@H]3NCC(N(C)C)=O)c3ccc2)[s]1 XSZVUKXQDQTDQT-QFIPXVFZSA-N 0.000 description 1
- DBFLEUHKDHLJTP-QFIPXVFZSA-N CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CC[C@@H]3NCCOC)c3ccc2)[s]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1ncc(-c2c(CC[C@@H]3NCCOC)c3ccc2)[s]1 DBFLEUHKDHLJTP-QFIPXVFZSA-N 0.000 description 1
- FIRVFYZVZCHDSX-NRFANRHFSA-N CC(C)Oc(c(C#N)c1)ccc1-c1nnc(-c2cccc3c2CCC[C@@H]3NCC(NC)=O)[s]1 Chemical compound CC(C)Oc(c(C#N)c1)ccc1-c1nnc(-c2cccc3c2CCC[C@@H]3NCC(NC)=O)[s]1 FIRVFYZVZCHDSX-NRFANRHFSA-N 0.000 description 1
- MQUHXLNCCTZXSJ-NRFANRHFSA-N CC(C)Oc(c(N)c1)ccc1-c1nnc(-c2c(CCC[C@@H]3NS(CCOC)(=O)=O)c3ccc2)[s]1 Chemical compound CC(C)Oc(c(N)c1)ccc1-c1nnc(-c2c(CCC[C@@H]3NS(CCOC)(=O)=O)c3ccc2)[s]1 MQUHXLNCCTZXSJ-NRFANRHFSA-N 0.000 description 1
- IRCFTXRTDROOIZ-UHFFFAOYSA-N CC(C)Oc(cc1)c(C)cc1-c1ncc(-c2c(CCC3N4CCCCC4)c3ccc2)[s]1 Chemical compound CC(C)Oc(cc1)c(C)cc1-c1ncc(-c2c(CCC3N4CCCCC4)c3ccc2)[s]1 IRCFTXRTDROOIZ-UHFFFAOYSA-N 0.000 description 1
- HAADVQLQVHKMRH-UHFFFAOYSA-N CC(C)Oc(ccc(-c1ccc(-c2cccc3c2CCC3O)[s]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ccc(-c2cccc3c2CCC3O)[s]1)c1)c1C#N HAADVQLQVHKMRH-UHFFFAOYSA-N 0.000 description 1
- LGTCIBWMSCRNLV-HSTJUUNISA-N CC(C)Oc(ccc(-c1ncc(-c2c(CCC3N(CC4)C[C@H]4O)c3ccc2)[s]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2c(CCC3N(CC4)C[C@H]4O)c3ccc2)[s]1)c1)c1C#N LGTCIBWMSCRNLV-HSTJUUNISA-N 0.000 description 1
- DBFLEUHKDHLJTP-UHFFFAOYSA-N CC(C)Oc(ccc(-c1ncc(-c2c(CCC3NCCOC)c3ccc2)[s]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2c(CCC3NCCOC)c3ccc2)[s]1)c1)c1C#N DBFLEUHKDHLJTP-UHFFFAOYSA-N 0.000 description 1
- PDHJOJDTKNNIAL-FQEVSTJZSA-N CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@@H]3NCC(O)=O)c3ccc2)[s]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@@H]3NCC(O)=O)c3ccc2)[s]1)c1)c1C#N PDHJOJDTKNNIAL-FQEVSTJZSA-N 0.000 description 1
- ZNINXPXWDFBZBP-NRFANRHFSA-N CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@@H]3NCCO)c3ccc2)[s]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2c(CC[C@@H]3NCCO)c3ccc2)[s]1)c1)c1C#N ZNINXPXWDFBZBP-NRFANRHFSA-N 0.000 description 1
- ZESMVJNMKLWJNE-XESZBRCGSA-N CC(C)Oc(ccc(-c1ncc(-c2cccc3c2CCC3N[C@H](C)CO)[s]1)c1)c1C#N Chemical compound CC(C)Oc(ccc(-c1ncc(-c2cccc3c2CCC3N[C@H](C)CO)[s]1)c1)c1C#N ZESMVJNMKLWJNE-XESZBRCGSA-N 0.000 description 1
- ZGCWDFFYOAEJAQ-HXUWFJFHSA-N CC(C)Oc(ccc(-c1nnc(-c2cccc3c2CCC[C@H]3NCCN=S)[s]1)c1)c1NC Chemical compound CC(C)Oc(ccc(-c1nnc(-c2cccc3c2CCC[C@H]3NCCN=S)[s]1)c1)c1NC ZGCWDFFYOAEJAQ-HXUWFJFHSA-N 0.000 description 1
- ZPRQXGPGMPRXHF-PKAZHMFMSA-N CC(C)Oc(ccc(C(S/C(/c1c(CCC2N3CCCC3)c2ccc1)=C\N)=C)c1)c1C#N Chemical compound CC(C)Oc(ccc(C(S/C(/c1c(CCC2N3CCCC3)c2ccc1)=C\N)=C)c1)c1C#N ZPRQXGPGMPRXHF-PKAZHMFMSA-N 0.000 description 1
- NXVMHQBGEDYGMA-UHFFFAOYSA-N CCSCCNC(CCC12)C1=CC=CC2c1cnc(-c(cc2C#N)ccc2OC(C)C)[s]1 Chemical compound CCSCCNC(CCC12)C1=CC=CC2c1cnc(-c(cc2C#N)ccc2OC(C)C)[s]1 NXVMHQBGEDYGMA-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 206010025327 Lymphopenia Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FCFUVRKPBYUYOI-UHFFFAOYSA-N NCC(N(CC1)CC1O)=O Chemical compound NCC(N(CC1)CC1O)=O FCFUVRKPBYUYOI-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 239000012351 deprotecting agent Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 231100001023 lymphopenia Toxicity 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical group CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- GOWNSHUNTJWVOM-UHFFFAOYSA-N tributyl(1,3-thiazol-5-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CS1 GOWNSHUNTJWVOM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161486184P | 2011-05-13 | 2011-05-13 | |
| US61/486,184 | 2011-05-13 | ||
| PCT/US2012/037609 WO2012158550A2 (en) | 2011-05-13 | 2012-05-11 | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014517836A JP2014517836A (ja) | 2014-07-24 |
| JP2014517836A5 true JP2014517836A5 (enExample) | 2015-06-25 |
| JP6129159B2 JP6129159B2 (ja) | 2017-05-17 |
Family
ID=47177578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014510511A Active JP6129159B2 (ja) | 2011-05-13 | 2012-05-11 | 選択的複素環式スフィンゴシン１−リン酸受容体モジュレーター |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9481659B2 (enExample) |
| EP (1) | EP2706999B1 (enExample) |
| JP (1) | JP6129159B2 (enExample) |
| ES (1) | ES2758841T3 (enExample) |
| WO (1) | WO2012158550A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS61829B1 (sr) | 2009-11-13 | 2021-06-30 | Receptos Llc | Selektivni modulatori receptora sfingozin 1 fosfata i metode hiralne sinteze |
| UY35338A (es) | 2013-02-21 | 2014-08-29 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos bicíclicos moduladores de la actividad de s1p1 y composiciones farmacéuticas que los contienen |
| CN106187945A (zh) * | 2016-07-22 | 2016-12-07 | 辽宁师范大学 | 一种有机合成中间体的合成方法 |
| EP3492465B1 (en) * | 2016-07-22 | 2021-03-24 | Shijiazhuang Sagacity New Drug Development Co., Ltd. | S1p1 agonist and application thereof |
| US10981900B2 (en) * | 2017-02-28 | 2021-04-20 | Medshine Discovery Inc. | Spiro compound and use thereof |
| CN112771028A (zh) * | 2018-09-12 | 2021-05-07 | 细胞制药有限公司 | 用于制备奥扎莫德及其中间体(s)-1-氨基-2,3-二氢-1h-茚基-4-甲腈的方法 |
| CN112457305B (zh) | 2019-09-09 | 2025-01-10 | 上海长森药业有限公司 | 含三环结构的芳香杂环化合物，及其制备方法和应用 |
| CN115279740B (zh) * | 2020-03-04 | 2025-02-28 | 南昌弘益药业有限公司 | 苯并2-氮杂螺[4.4]壬烷类化合物及其应用 |
| US20230357219A1 (en) | 2020-05-11 | 2023-11-09 | Shanghai Longwood Biopharmaceuticals Co., Ltd. | Preparation of biaryl ring-linked aromatic heterocyclic derivative as immunomodulator and use thereof |
| US20240182457A1 (en) * | 2021-04-09 | 2024-06-06 | Helioeast Pharmaceutical Co., Ltd. | Oxadiazole-substituted spirocyclic compound and application thereof |
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2012
- 2012-05-11 US US14/117,514 patent/US9481659B2/en active Active
- 2012-05-11 WO PCT/US2012/037609 patent/WO2012158550A2/en not_active Ceased
- 2012-05-11 JP JP2014510511A patent/JP6129159B2/ja active Active
- 2012-05-11 ES ES12785231T patent/ES2758841T3/es active Active
- 2012-05-11 EP EP12785231.7A patent/EP2706999B1/en active Active
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