JP2010521464A5 - - Google Patents
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- Publication number
- JP2010521464A5 JP2010521464A5 JP2009553626A JP2009553626A JP2010521464A5 JP 2010521464 A5 JP2010521464 A5 JP 2010521464A5 JP 2009553626 A JP2009553626 A JP 2009553626A JP 2009553626 A JP2009553626 A JP 2009553626A JP 2010521464 A5 JP2010521464 A5 JP 2010521464A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- cycloalkyl
- independently
- 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.)
- Granted
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- 125000003118 aryl group Chemical group 0.000 claims 63
- 125000001072 heteroaryl group Chemical group 0.000 claims 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims 54
- 125000000217 alkyl group Chemical group 0.000 claims 50
- 229910052739 hydrogen Inorganic materials 0.000 claims 35
- -1 substituted aryl alcohol Chemical compound 0.000 claims 34
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 31
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 30
- 125000004404 heteroalkyl group Chemical group 0.000 claims 28
- 229910052799 carbon Inorganic materials 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 25
- 238000000034 method Methods 0.000 claims 25
- 239000003446 ligand Substances 0.000 claims 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims 22
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 20
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 20
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 15
- 125000003107 substituted aryl group Chemical group 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 150000001412 amines Chemical class 0.000 claims 12
- 125000006239 protecting group Chemical group 0.000 claims 12
- 150000002576 ketones Chemical class 0.000 claims 11
- 150000003839 salts Chemical group 0.000 claims 11
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 10
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 10
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 10
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 10
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 10
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 10
- 150000001299 aldehydes Chemical class 0.000 claims 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 10
- 125000004414 alkyl thio group Chemical group 0.000 claims 10
- 150000001408 amides Chemical class 0.000 claims 10
- 150000001409 amidines Chemical class 0.000 claims 10
- 150000008064 anhydrides Chemical class 0.000 claims 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 10
- 150000001540 azides Chemical class 0.000 claims 10
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims 10
- 239000004202 carbamide Substances 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 150000003857 carboxamides Chemical class 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 10
- 150000002118 epoxides Chemical class 0.000 claims 10
- 150000002148 esters Chemical class 0.000 claims 10
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 10
- 150000003949 imides Chemical class 0.000 claims 10
- 150000002466 imines Chemical class 0.000 claims 10
- 150000002825 nitriles Chemical class 0.000 claims 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 10
- 150000002923 oximes Chemical class 0.000 claims 10
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 10
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 10
- 229940124530 sulfonamide Drugs 0.000 claims 10
- 150000003456 sulfonamides Chemical class 0.000 claims 10
- 125000004001 thioalkyl group Chemical group 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical group C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims 4
- 150000001350 alkyl halides Chemical class 0.000 claims 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- 229910052723 transition metal Inorganic materials 0.000 claims 3
- 150000003624 transition metals Chemical class 0.000 claims 3
- 150000000179 1,2-aminoalcohols Chemical class 0.000 claims 2
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims 2
- JIVLDFFWTQYGSR-UHFFFAOYSA-N 4,7-dimethyl-[1,10]phenanthroline Chemical compound C1=CC2=C(C)C=CN=C2C2=C1C(C)=CC=N2 JIVLDFFWTQYGSR-UHFFFAOYSA-N 0.000 claims 2
- ACMIJDVJWLMBCX-PXAZEXFGSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-6-fluoro-n-methyl-2-(2-methylpyrimidin-5-yl)oxy-9h-pyrimido[4,5-b]indol-8-amine Chemical compound CNC1=CC(F)=CC(C2=C(N3C[C@@H]4NCC[C@@H]4C3)N=3)=C1NC2=NC=3OC1=CN=C(C)N=C1 ACMIJDVJWLMBCX-PXAZEXFGSA-N 0.000 claims 2
- XDUUQOQFSWSZSM-UHFFFAOYSA-N 5-chloro-1,10-phenanthroline Chemical compound C1=CC=C2C(Cl)=CC3=CC=CN=C3C2=N1 XDUUQOQFSWSZSM-UHFFFAOYSA-N 0.000 claims 2
- UJAQYOZROIFQHO-UHFFFAOYSA-N 5-methyl-1,10-phenanthroline Chemical compound C1=CC=C2C(C)=CC3=CC=CN=C3C2=N1 UJAQYOZROIFQHO-UHFFFAOYSA-N 0.000 claims 2
- PDDBTWXLNJNICS-UHFFFAOYSA-N 5-nitro-1,10-phenanthroline Chemical compound C1=CC=C2C([N+](=O)[O-])=CC3=CC=CN=C3C2=N1 PDDBTWXLNJNICS-UHFFFAOYSA-N 0.000 claims 2
- IDXZWQWBZPVICI-UHFFFAOYSA-N CN(C)C(C=CN1)=CC1=C.C1=CN=CN1 Chemical compound CN(C)C(C=CN1)=CC1=C.C1=CN=CN1 IDXZWQWBZPVICI-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 238000003821 enantio-separation Methods 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 230000000269 nucleophilic effect Effects 0.000 claims 2
- 239000003223 protective agent Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- SBTVLCPCSXMWIQ-UHFFFAOYSA-N (3,5-dimethylphenyl) carbamate Chemical compound CC1=CC(C)=CC(OC(N)=O)=C1 SBTVLCPCSXMWIQ-UHFFFAOYSA-N 0.000 claims 1
- VXIVSQZSERGHQP-HQMMCQRPSA-N 2-chloroacetamide Chemical group N[14C](=O)CCl VXIVSQZSERGHQP-HQMMCQRPSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 239000012964 benzotriazole Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 claims 1
- VEWFZHAHZPVQES-UHFFFAOYSA-N boron;n,n-diethylethanamine Chemical compound [B].CCN(CC)CC VEWFZHAHZPVQES-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 claims 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 229910003450 rhodium oxide Inorganic materials 0.000 claims 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 claims 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- 229960002317 succinimide Drugs 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011787 zinc oxide Substances 0.000 claims 1
- 0 *c1c(*)c(*)c(*)c2c1c(/N=*/NCC*1)c1[n]2 Chemical compound *c1c(*)c(*)c(*)c2c1c(/N=*/NCC*1)c1[n]2 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90647307P | 2007-03-12 | 2007-03-12 | |
| US60/906,473 | 2007-03-12 | ||
| PCT/US2008/003340 WO2008112280A1 (en) | 2007-03-12 | 2008-03-12 | Substituted heterocycle fused gamma-carbolines synthesis |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014126495A Division JP5918306B2 (ja) | 2007-03-12 | 2014-06-19 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010521464A JP2010521464A (ja) | 2010-06-24 |
| JP2010521464A5 true JP2010521464A5 (enExample) | 2011-05-06 |
| JP5567349B2 JP5567349B2 (ja) | 2014-08-06 |
Family
ID=39759858
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009553626A Active JP5567349B2 (ja) | 2007-03-12 | 2008-03-12 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2014126495A Active JP5918306B2 (ja) | 2007-03-12 | 2014-06-19 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2016077538A Active JP6231151B2 (ja) | 2007-03-12 | 2016-04-07 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2017201937A Active JP6522710B2 (ja) | 2007-03-12 | 2017-10-18 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2019082541A Active JP6773837B2 (ja) | 2007-03-12 | 2019-04-24 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2020166874A Withdrawn JP2021006559A (ja) | 2007-03-12 | 2020-10-01 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2022144080A Pending JP2022180440A (ja) | 2007-03-12 | 2022-09-09 | 置換ヘテロ環縮合ガンマ－カルボリンの合成 |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014126495A Active JP5918306B2 (ja) | 2007-03-12 | 2014-06-19 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2016077538A Active JP6231151B2 (ja) | 2007-03-12 | 2016-04-07 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2017201937A Active JP6522710B2 (ja) | 2007-03-12 | 2017-10-18 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2019082541A Active JP6773837B2 (ja) | 2007-03-12 | 2019-04-24 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2020166874A Withdrawn JP2021006559A (ja) | 2007-03-12 | 2020-10-01 | 置換ヘテロ環縮合ガンマ−カルボリンの合成 |
| JP2022144080A Pending JP2022180440A (ja) | 2007-03-12 | 2022-09-09 | 置換ヘテロ環縮合ガンマ－カルボリンの合成 |
Country Status (12)
| Country | Link |
|---|---|
| US (11) | US8309722B2 (enExample) |
| EP (2) | EP3663294A1 (enExample) |
| JP (7) | JP5567349B2 (enExample) |
| KR (7) | KR102372149B1 (enExample) |
| CN (2) | CN101796051B (enExample) |
| AU (5) | AU2008226814C1 (enExample) |
| CA (1) | CA2679754C (enExample) |
| DK (1) | DK2134710T3 (enExample) |
| ES (1) | ES2776889T3 (enExample) |
| IN (1) | IN2009DN05670A (enExample) |
| MX (3) | MX394214B (enExample) |
| WO (1) | WO2008112280A1 (enExample) |
Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101796051B (zh) | 2007-03-12 | 2013-11-06 | 细胞内治疗公司 | 与取代的杂环稠合的γ-咔啉的合成 |
| KR101614723B1 (ko) | 2008-01-11 | 2016-04-22 | 알바니 몰레큘라 리써치, 인크. | Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌 |
| CN105237536A (zh) | 2008-03-12 | 2016-01-13 | 细胞内治疗公司 | 取代的杂环稠合的γ-咔啉固体 |
| KR20110022631A (ko) | 2008-05-27 | 2011-03-07 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 수면 장애 및 다른 장애를 치료하기 위한 방법 및 조성물 |
| US9107696B2 (en) * | 2008-08-06 | 2015-08-18 | Emory University | Method of embryo transfer that eliminates transferred air while hormonally inducing implantation and apparatus |
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- 2019-01-10 US US16/244,796 patent/US10597395B2/en active Active
- 2019-04-24 JP JP2019082541A patent/JP6773837B2/ja active Active
- 2019-06-12 US US16/439,361 patent/US10464938B2/en active Active
- 2019-09-10 AU AU2019229334A patent/AU2019229334B2/en active Active
- 2019-10-07 US US16/594,603 patent/US11407751B2/en active Active
- 2019-12-12 US US16/711,790 patent/US11066407B2/en active Active
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2020
- 2020-10-01 JP JP2020166874A patent/JP2021006559A/ja not_active Withdrawn
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2022
- 2022-06-24 US US17/808,836 patent/US12139490B2/en active Active
- 2022-09-09 JP JP2022144080A patent/JP2022180440A/ja active Pending
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2024
- 2024-10-03 US US18/905,607 patent/US20250101022A1/en active Pending
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