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) | CN103626766B (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 (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX394214B (es) | 2007-03-12 | 2025-03-24 | Intra Cellular Therapies Inc | Sintesis de gamma-carbolinas fusionadas con heterociclo substituido. |
| CA2727055C (en) | 2008-01-11 | 2016-12-20 | Albany Molecular Research, Inc. | (1-azinone) -substituted pyridoindoles as mch antagonists |
| ES2530090T3 (es) | 2008-03-12 | 2015-02-26 | Intra-Cellular Therapies, Inc. | Sólido de gamma-carbolinas fusionadas con heterociclo sustituido |
| CA2725342C (en) | 2008-05-27 | 2024-02-20 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for sleep disorders and other disorders |
| US9107696B2 (en) * | 2008-08-06 | 2015-08-18 | Emory University | Method of embryo transfer that eliminates transferred air while hormonally inducing implantation and apparatus |
| US9625475B2 (en) | 2008-09-29 | 2017-04-18 | Abbvie Inc. | Indole and indoline derivatives and methods of use thereof |
| TW201018694A (en) | 2008-09-29 | 2010-05-16 | Abbott Lab | Indole and indoline derivatives and methods of use thereof |
| WO2011003005A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine mch-1 antagonists, methods of making, and use thereof |
| WO2011003021A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| WO2011003012A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle mch-1 antagonists, methods of making, and use thereof |
| US8629158B2 (en) | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| US8993572B2 (en) | 2010-04-22 | 2015-03-31 | Intra-Cellular Therapies, Inc. | Pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines derivatives and [1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole derivatives |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| WO2012088124A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline mch-1 antagonists, methods of making, and uses thereof |
| US9428506B2 (en) * | 2012-04-14 | 2016-08-30 | Intra-Cellular Therapies, Inc. | Substituted pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines for the treatment of nervous system disorders |
| WO2014145192A1 (en) | 2013-03-15 | 2014-09-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR102967223B1 (ko) | 2013-12-03 | 2026-05-19 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 신규한 방법 |
| US9745300B2 (en) | 2014-04-04 | 2017-08-29 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR20220054908A (ko) | 2014-04-04 | 2022-05-03 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| US10179776B2 (en) | 2014-06-09 | 2019-01-15 | Intra-Cellular Therapies, Inc. | Compounds and methods of use to treat schizophrenia |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| US10253024B2 (en) | 2015-04-30 | 2019-04-09 | The Regents Of The University Of Colorado, A Body Corporate | Polycyclic indoline and indolenine compounds |
| RU2743513C2 (ru) | 2016-01-26 | 2021-02-19 | Интра-Селлулар Терапиз, Инк. | Органические соединения |
| IL281050B2 (en) | 2016-03-25 | 2023-04-01 | Intra Cellular Therapies Inc | A controlled or delayed release pharmaceutical preparation containing a deuterated compound |
| WO2017172811A1 (en) * | 2016-03-28 | 2017-10-05 | Intra-Cellular Therapies, Inc. | Novel co-crystals |
| US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| WO2017172784A1 (en) * | 2016-03-28 | 2017-10-05 | Intra-Cellular Therapies, Inc. | Novel salts and crystals |
| HUE057055T2 (hu) | 2016-08-09 | 2022-04-28 | Teva Pharmaceuticals Int Gmbh | Lumateperon-ditozilátsó szilárd halmazállapotú formái |
| EP3519816A4 (en) | 2016-09-29 | 2020-05-06 | The Regents of the University of California | CONNECTIONS FOR INCREASING NEURONAL PLASTICITY |
| JP7013454B2 (ja) | 2016-10-12 | 2022-02-15 | イントラ－セルラー・セラピーズ・インコーポレイテッド | アモルファス固体分散体 |
| EP3562484B1 (en) | 2016-12-29 | 2021-08-25 | Intra-Cellular Therapies, Inc. | Pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline derivatives useful in the treatment of cns disorders |
| WO2018126140A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP3600325A4 (en) | 2017-03-24 | 2021-01-06 | Intra-Cellular Therapies, Inc. | UNIQUE COMPOSITIONS AND PROCESSES |
| WO2018189646A1 (en) | 2017-04-10 | 2018-10-18 | Dr. Reddy's Laboratories Limited | AMORPHOUS FORM AND SOLID DISPERSIONS OF LUMATEPERONE p-TOSYLATE |
| JP7224333B2 (ja) | 2017-07-26 | 2023-02-17 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| WO2019023062A1 (en) | 2017-07-26 | 2019-01-31 | Intra-Cellular Therapies, Inc. | ORGANIC COMPOUNDS |
| WO2019067591A1 (en) | 2017-09-26 | 2019-04-04 | Intra-Cellular Therapies, Inc. | NEW SALTS AND CRYSTALS |
| WO2019102240A1 (en) | 2017-11-27 | 2019-05-31 | Egis Gyógyszergyár Zrt. | Method for the manufacture of lumateperone and its salts |
| WO2019178484A1 (en) | 2018-03-16 | 2019-09-19 | Intra-Cellular Therapies, Inc. | Novel methods |
| SMT202600133T1 (it) | 2018-03-23 | 2026-05-12 | Intra Cellular Therapies Inc | Composti organici |
| AU2019240226B2 (en) | 2018-03-23 | 2024-11-28 | Intra-Cellular Therapies, Inc. | Organic compounds |
| BR112020024885A2 (pt) | 2018-06-06 | 2021-03-09 | Intra-Cellular Therapies, Inc. | Novos sais e cristais |
| EP3801527B1 (en) | 2018-06-08 | 2025-02-19 | Intra-Cellular Therapies, Inc. | Fused gamma-carbolines for acute treatment of anxiety or depression |
| RS67906B1 (sr) | 2018-06-11 | 2026-04-30 | Intra Cellular Therapies Inc | Sinteza supstituisanih heterociklično fuzionisanih gama-karbolina |
| EP3811371A1 (en) | 2018-06-21 | 2021-04-28 | Aquestive Therapeutics, Inc. | System and method for making personalized individual unit doses containing pharmaceutical actives |
| MY210507A (en) | 2018-08-13 | 2025-09-28 | Hoffmann La Roche | New heterocyclic compounds as monoacylglycerol lipase inhibitors |
| US12144808B2 (en) | 2018-08-29 | 2024-11-19 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| WO2020047408A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| AU2019328528B2 (en) | 2018-08-31 | 2025-01-23 | Intra-Cellular Therapies, Inc. | Novel methods |
| WO2020051317A1 (en) | 2018-09-07 | 2020-03-12 | Aquestive Therapeutics, Inc. | Oral film compositions and dosage forms having precise active dissolution profiles |
| WO2020104494A1 (en) | 2018-11-22 | 2020-05-28 | F. Hoffmann-La Roche Ag | New heterocyclic compounds |
| WO2020112941A2 (en) | 2018-11-27 | 2020-06-04 | Teva Czech Industries S.R.O | Solid state forms of lumateperone salts and processes for preparation of lumateperone and salts thereof |
| ES3047409T3 (en) | 2018-12-17 | 2025-12-03 | Intra Cellular Therapies Inc | Substituted heterocycle fused gamma-carbolines synthesis |
| KR20210104785A (ko) | 2018-12-17 | 2021-08-25 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| IL315005B2 (en) * | 2018-12-17 | 2026-04-01 | Intra Cellular Therapies Inc | Substituted heterocycle fused gamma-carbolines synthesis |
| JP7377871B2 (ja) | 2018-12-21 | 2023-11-10 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| US12331052B2 (en) | 2018-12-21 | 2025-06-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR102946120B1 (ko) | 2019-02-27 | 2026-03-30 | 더 리젠츠 오브 더 유니버시티 오브 캘리포니아 | 뇌 장애를 치료하기 위한 아제피노-인돌 및 다른 헤테로사이클 |
| EP4134101A1 (en) | 2019-07-07 | 2023-02-15 | Intra-Cellular Therapies, Inc. | Deuterated lumateperone for the treatment of the bipolar ii disorder |
| JP2022549335A (ja) | 2019-09-25 | 2022-11-24 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規方法 |
| MX2022004983A (es) | 2019-11-01 | 2022-09-23 | Aquestive Therapeutics Inc | Composiciones de profarmaco y metodos de tratamiento. |
| CA3159389A1 (en) | 2019-11-14 | 2021-05-20 | Aquestive Therapeutics, Inc. | Multimodal compositions comprising diazepam and methods of treatment |
| CN110698474B (zh) * | 2019-11-14 | 2021-11-02 | 福州大学 | 一种α位取代四氢-γ-咔啉类化合物及其制备方法和应用 |
| WO2021119334A1 (en) | 2019-12-11 | 2021-06-17 | Intra-Cellular Therapies, Inc. | Organic compound |
| LT4076461T (lt) | 2019-12-19 | 2026-06-25 | Intra-Cellular Therapies, Inc. | Lumateperonas, skirtas panaudoti šizofrenijos gydymui |
| CN112062767B (zh) * | 2020-10-20 | 2022-03-11 | 杭州科巢生物科技有限公司 | 一种卢美哌隆的制备方法及其中间体 |
| JP2024505429A (ja) | 2021-01-15 | 2024-02-06 | アクエスティブ セラピューティクス インコーポレイテッド | プロドラッグ組成物及び治療の方法 |
| US20220347117A1 (en) | 2021-03-09 | 2022-11-03 | Aquestive Therapeutics, Inc. | Dosage forms having equivalent biocomparable profiles |
| CN113024554B (zh) * | 2021-03-24 | 2023-03-14 | 上海法默生物科技有限公司 | 一种卢美哌隆中间体的制备方法 |
| WO2022221415A2 (en) | 2021-04-13 | 2022-10-20 | The Regents Of The University Of California | Tetracyclic compounds for treating brain disorders |
| CN114105985B (zh) * | 2021-12-13 | 2024-04-16 | 南方科技大学坪山生物医药研究院 | 不对称氢化构建卢美哌隆中间体的方法及卢美哌隆中间体 |
| CN114105980B (zh) * | 2021-12-13 | 2024-04-16 | 南方科技大学坪山生物医药研究院 | 卢美哌隆中间体化合物的制备方法及卢美哌隆中间体化合物 |
| JP2025502615A (ja) | 2021-12-15 | 2025-01-28 | デリックス セラピューティクス，インク． | フェノキシおよびベンジルオキシ置換サイコプラストゲンならびにその使用 |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
| KR20250123225A (ko) | 2022-12-30 | 2025-08-14 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| CN121152625A (zh) | 2023-02-17 | 2025-12-16 | 细胞内治疗公司 | 用于调节神经系统的卢美哌隆和其衍生物 |
| WO2025223504A1 (zh) * | 2024-04-26 | 2025-10-30 | 浙江奥翔药业股份有限公司 | 卢美哌隆中间体及其制备方法 |
| US20250352469A1 (en) | 2024-05-16 | 2025-11-20 | Intra-Cellular Therapies, Inc. | Novel compositions, devices, and methods |
| WO2025257090A1 (en) | 2024-06-10 | 2025-12-18 | Interquim, S.A. | Process for the preparation of synthesis intermediates of lumateperone and lumateperone analogues |
| WO2026011136A1 (en) | 2024-07-03 | 2026-01-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2026011166A1 (en) | 2024-07-03 | 2026-01-08 | Intra-Cellular Therapies, Inc. | Substituted heterocycles for use in the treatment of diseases involving the 5-ht2a receptor |
| CN119912455B (zh) * | 2025-01-22 | 2025-09-23 | 成都臻拓医药科技有限公司 | 一种卢美哌隆中间体化合物的制备方法 |
Family Cites Families (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US38679A (en) | 1863-05-26 | Improvement in water-elevators | ||
| US471A (en) | 1837-11-20 | Mode of | ||
| US39680A (en) | 1863-08-25 | Improvement in machines for breaking and cleaning flax | ||
| US6713A (en) | 1849-09-11 | Hobse-poweb | ||
| US2490813A (en) | 1944-11-29 | 1949-12-13 | Standard Oil Co | Continuous process for making aryl amines |
| US3299078A (en) | 1962-10-01 | 1967-01-17 | Smith Kline French Lab | Pyrido [3', 4': 4, 5] pyrrolo [3, 2, 1-hi] indoles and-[3, 2, 1-ij] quinolines |
| US3813392A (en) | 1969-06-09 | 1974-05-28 | J Sellstedt | Pyrrolo(1,2,3-alpha epsilon)quinoxalin-2(3h)-ones and related compounds |
| US4238607A (en) | 1972-06-19 | 1980-12-09 | Endo Laboratories Inc. | Pyridopyrrolo benzheterocycles |
| US4183936A (en) | 1972-06-19 | 1980-01-15 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| US4115577A (en) | 1972-06-19 | 1978-09-19 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| US3914421A (en) | 1972-06-19 | 1975-10-21 | Endo Lab | Pyridopyrrolobenzheterocycles for combatting depression |
| US4219550A (en) | 1978-11-09 | 1980-08-26 | E. I. Du Pont De Nemours And Company | Cis- and trans- octahydropyridopyrrolobenzheterocycles |
| US4522944A (en) | 1982-12-23 | 1985-06-11 | Erba Farmitalia | Carboxamido-derivatives of 5H-1,3,4-thiadiazolo[3,2-a]pyrimidines, compositions and use |
| ES2058068T3 (es) | 1986-03-19 | 1994-11-01 | Kumiai Chemical Industry Co | Derivados de 5h-1,3,4-tiadiazol-(3,2-a)-pirimidin-5-ona y compuestos fungicidas con contenido en dichos derivados. |
| ATE91129T1 (de) | 1986-04-07 | 1993-07-15 | Kumiai Chemical Industry Co | 5h-1,3,4-thiadiazolo(3,2-a>pyrimidin-5-onderivate und diese enthaltende gartenbau- und landwirtschaftliche fungizidmittel. |
| US5576460A (en) | 1994-07-27 | 1996-11-19 | Massachusetts Institute Of Technology | Preparation of arylamines |
| US5648539A (en) | 1996-02-29 | 1997-07-15 | Xerox Corporation | Low temperature arylamine processes |
| US5648542A (en) | 1996-02-29 | 1997-07-15 | Xerox Corporation | Arylamine processes |
| US5654482A (en) | 1996-02-29 | 1997-08-05 | Xerox Corporation | Triarylamine processes |
| US5847166A (en) | 1996-10-10 | 1998-12-08 | Massachusetts Institute Of Technology | Synthesis of aryl ethers |
| US5705697A (en) | 1997-01-30 | 1998-01-06 | Xerox Corporation | Arylamine processes |
| US5723669A (en) | 1997-01-30 | 1998-03-03 | Xerox Corporation | Arylamine processes |
| US5723671A (en) | 1997-01-30 | 1998-03-03 | Xerox Corporation | Arylamine processes |
| US6323366B1 (en) | 1997-07-29 | 2001-11-27 | Massachusetts Institute Of Technology | Arylamine synthesis |
| GB2328686B (en) | 1997-08-25 | 2001-09-26 | Sankio Chemical Co Ltd | Method for producing arylamine |
| WO1999018057A1 (en) | 1997-10-06 | 1999-04-15 | Massachusetts Institute Of Technology | Preparation of diaryl ether by condensation reactions |
| EP1058678B1 (en) | 1998-02-26 | 2002-12-11 | Massachusetts Institute of Technology | Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes |
| US6235936B1 (en) | 1998-02-26 | 2001-05-22 | Massachusetts Institute Of Technology | Metal-catalyzed arylations of hydrazines, hydrazones, and related substrates |
| US5902901A (en) | 1998-05-07 | 1999-05-11 | Xerox Corporation | Arylamine processes |
| US6395916B1 (en) | 1998-07-10 | 2002-05-28 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| JP5035813B2 (ja) | 1998-07-10 | 2012-09-26 | マサチューセッツ インスティテュート オブ テクノロジー | 金属用のリガンドおよびそれらに基づいて改善された金属触媒法 |
| US6307087B1 (en) | 1998-07-10 | 2001-10-23 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US7223879B2 (en) | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US20010008942A1 (en) | 1998-12-08 | 2001-07-19 | Buchwald Stephen L. | Synthesis of aryl ethers |
| PE20010052A1 (es) | 1999-04-23 | 2001-01-27 | Upjohn Co | Compuestos de azepinindol tetraciclico como agonistas o antagonistas del receptor de 5-ht |
| US6407092B1 (en) | 1999-04-23 | 2002-06-18 | Pharmacia & Upjohn Company | Tetracyclic azepinoindole compounds |
| US7071186B2 (en) | 1999-06-15 | 2006-07-04 | Bristol-Myers Squibb Pharma Co. | Substituted heterocycle fused gamma-carbolines |
| WO2000077001A1 (en) | 1999-06-15 | 2000-12-21 | Du Pont Pharmaceuticals Company | Substituted heterocycle fused gamma-carbolines |
| US6713471B1 (en) | 1999-06-15 | 2004-03-30 | Bristol-Myers Squibb Pharma Company | Substituted heterocycle fused gamma-carbolines |
| US6541639B2 (en) | 2000-07-26 | 2003-04-01 | Bristol-Myers Squibb Pharma Company | Efficient ligand-mediated Ullmann coupling of anilines and azoles |
| US6849619B2 (en) | 2000-12-20 | 2005-02-01 | Bristol-Myers Squibb Company | Substituted pyridoindoles as serotonin agonists and antagonists |
| RU2003121304A (ru) | 2000-12-20 | 2005-01-27 | Бристол-Маерс Сквибб Компани (Us) | Замещенные пиридоиндолы в качестве агонистов и антагонистов серотонина |
| KR20030092107A (ko) | 2001-04-24 | 2003-12-03 | 메사추세츠 인스티튜트 오브 테크놀로지 | 탄소-헤테로원자 및 탄소-탄소 결합을 형성하는 구리-촉매방법 |
| US6849640B2 (en) * | 2001-08-08 | 2005-02-01 | Pharmacia & Upjohn Company | Therapeutic 1H-pyrido [4,3-b] indoles |
| US6888032B2 (en) | 2002-08-02 | 2005-05-03 | Massachusetts Institute Of Technology | Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds |
| US7223870B2 (en) | 2002-11-01 | 2007-05-29 | Pfizer Inc. | Methods for preparing N-arylated oxazolidinones via a copper catalyzed cross coupling reaction |
| WO2004056324A2 (en) | 2002-12-19 | 2004-07-08 | Bristol-Myers Squibb Company | Substituted tricyclic gamma-carbolines as serotonin receptor agonists and antagonists |
| JP2005259113A (ja) | 2004-02-12 | 2005-09-22 | Ricoh Co Ltd | プロセス編集装置、プロセス管理装置、プロセス編集プログラム、プロセス管理プログラム、記録媒体、プロセス編集方法及びプロセス管理方法 |
| US7592454B2 (en) * | 2004-04-14 | 2009-09-22 | Bristol-Myers Squibb Company | Substituted hexahydro-pyridoindole derivatives as serotonin receptor agonists and antagonists |
| MX2007006896A (es) * | 2004-12-15 | 2007-06-26 | Hoffmann La Roche | Fenil-metanonas bi- y triciclicas sustituidas como inhibidores del transportador 1 de glicina (glyt-1) para el tratamiento de la enfermedad de alzheimer. |
| MX394214B (es) | 2007-03-12 | 2025-03-24 | Intra Cellular Therapies Inc | Sintesis de gamma-carbolinas fusionadas con heterociclo substituido. |
| ES2530090T3 (es) | 2008-03-12 | 2015-02-26 | Intra-Cellular Therapies, Inc. | Sólido de gamma-carbolinas fusionadas con heterociclo sustituido |
| CA2725342C (en) | 2008-05-27 | 2024-02-20 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for sleep disorders and other disorders |
| US8309772B2 (en) | 2008-07-31 | 2012-11-13 | Celanese International Corporation | Tunable catalyst gas phase hydrogenation of carboxylic acids |
| US8993572B2 (en) * | 2010-04-22 | 2015-03-31 | Intra-Cellular Therapies, Inc. | Pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines derivatives and [1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole derivatives |
| US9428506B2 (en) | 2012-04-14 | 2016-08-30 | Intra-Cellular Therapies, Inc. | Substituted pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines for the treatment of nervous system disorders |
| WO2014145192A1 (en) | 2013-03-15 | 2014-09-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR102967223B1 (ko) | 2013-12-03 | 2026-05-19 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 신규한 방법 |
| KR20220054908A (ko) | 2014-04-04 | 2022-05-03 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| IL281050B2 (en) | 2016-03-25 | 2023-04-01 | Intra Cellular Therapies Inc | A controlled or delayed release pharmaceutical preparation containing a deuterated compound |
| WO2019102240A1 (en) | 2017-11-27 | 2019-05-31 | Egis Gyógyszergyár Zrt. | Method for the manufacture of lumateperone and its salts |
-
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- 2008-03-12 MX MX2020001497A patent/MX394214B/es unknown
- 2008-03-12 KR KR1020217009724A patent/KR102372149B1/ko active Active
- 2008-03-12 MX MX2009009773A patent/MX2009009773A/es active IP Right Grant
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- 2008-03-12 US US12/531,016 patent/US8309722B2/en active Active
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- 2012-08-23 US US13/593,097 patent/US8779139B2/en active Active
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- 2014-06-26 AU AU2014203483A patent/AU2014203483B2/en active Active
- 2014-07-03 US US14/323,545 patent/US9315504B2/en active Active
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2016
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- 2016-04-07 JP JP2016077538A patent/JP6231151B2/ja active Active
- 2016-09-27 AU AU2016234905A patent/AU2016234905B2/en active Active
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2017
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- 2017-10-18 JP JP2017201937A patent/JP6522710B2/ja active Active
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2018
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2019
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- 2019-04-24 JP JP2019082541A patent/JP6773837B2/ja active Active
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2020
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2022
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2024
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