JP2014208676A5 - - Google Patents
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- Publication number
- JP2014208676A5 JP2014208676A5 JP2014126495A JP2014126495A JP2014208676A5 JP 2014208676 A5 JP2014208676 A5 JP 2014208676A5 JP 2014126495 A JP2014126495 A JP 2014126495A JP 2014126495 A JP2014126495 A JP 2014126495A JP 2014208676 A5 JP2014208676 A5 JP 2014208676A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- formula
- iii
- benzyl
- 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 35
- 238000000034 method Methods 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical group 0.000 claims 10
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 229910052740 iodine Inorganic materials 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 6
- -1 4- (4-fluorophenyl) -4-oxobutyl Chemical group 0.000 claims 5
- 239000003638 chemical reducing agent Substances 0.000 claims 5
- 239000010949 copper Substances 0.000 claims 5
- 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 4
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical group C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000003223 protective agent Substances 0.000 claims 4
- 229910052723 transition metal Inorganic materials 0.000 claims 4
- 150000003624 transition metals Chemical class 0.000 claims 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 3
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical group ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims 2
- 229910000085 borane Inorganic materials 0.000 claims 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 235000010755 mineral Nutrition 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- DFFWYMMOMUTKOI-UHFFFAOYSA-N 1-(3-chloropropoxy)-4-fluorobenzene Chemical compound FC1=CC=C(OCCCCl)C=C1 DFFWYMMOMUTKOI-UHFFFAOYSA-N 0.000 claims 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims 1
- HXAOUYGZEOZTJO-UHFFFAOYSA-N 4-chloro-1-(4-fluorophenyl)butan-1-one Chemical compound FC1=CC=C(C(=O)CCCCl)C=C1 HXAOUYGZEOZTJO-UHFFFAOYSA-N 0.000 claims 1
- 229910000497 Amalgam Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003710 aryl alkyl 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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- MJSHDCCLFGOEIK-UHFFFAOYSA-N benzyl (2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)OCC1=CC=CC=C1 MJSHDCCLFGOEIK-UHFFFAOYSA-N 0.000 claims 1
- CSDRYGFEWYQKSD-UHFFFAOYSA-N benzyl 2h-benzotriazole-4-carboxylate Chemical compound C=1C=CC=2NN=NC=2C=1C(=O)OCC1=CC=CC=C1 CSDRYGFEWYQKSD-UHFFFAOYSA-N 0.000 claims 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims 1
- 229940073608 benzyl chloride Drugs 0.000 claims 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910000160 potassium phosphate Inorganic materials 0.000 claims 1
- 235000011009 potassium phosphates Nutrition 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229960002317 succinimide Drugs 0.000 claims 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 0 BN(*)C*C1N(C**)c2c(*)c(**)c(B=*)c(*)c2[C@@]1(CNC)C=** Chemical compound BN(*)C*C1N(C**)c2c(*)c(**)c(B=*)c(*)c2[C@@]1(CNC)C=** 0.000 description 6
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90647307P | 2007-03-12 | 2007-03-12 | |
| US60/906,473 | 2007-03-12 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009553626A Division 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016077538A Division 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014208676A JP2014208676A (ja) | 2014-11-06 |
| JP2014208676A5 true JP2014208676A5 (OSRAM) | 2014-12-18 |
| JP5918306B2 JP5918306B2 (ja) | 2016-05-18 |
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 Before (1)
| 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 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 (OSRAM) |
| EP (2) | EP3663294A1 (OSRAM) |
| JP (7) | JP5567349B2 (OSRAM) |
| KR (7) | KR101805914B1 (OSRAM) |
| CN (2) | CN103626766B (OSRAM) |
| AU (5) | AU2008226814C1 (OSRAM) |
| CA (1) | CA2679754C (OSRAM) |
| DK (1) | DK2134710T3 (OSRAM) |
| ES (1) | ES2776889T3 (OSRAM) |
| IN (1) | IN2009DN05670A (OSRAM) |
| MX (3) | MX394214B (OSRAM) |
| WO (1) | WO2008112280A1 (OSRAM) |
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| KR101805914B1 (ko) | 2007-03-12 | 2017-12-06 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 치환된 헤테로환 융합 감마-카르볼린 합성 |
| KR101614723B1 (ko) | 2008-01-11 | 2016-04-22 | 알바니 몰레큘라 리써치, 인크. | Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌 |
| MX2010010024A (es) | 2008-03-12 | 2010-11-09 | Intra Cellular Therapies Inc | Solido de gamma-carbolinas fusionadas con heterociclos substituidos. |
| AU2009251816B2 (en) | 2008-05-27 | 2015-12-10 | Intra-Cellular Therapies, Inc. | Methods and compositions 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 |
| EP2344505A2 (en) | 2008-09-29 | 2011-07-20 | Abbott Laboratories | Indole and indoline derivatives and methods of use thereof |
| US8618299B2 (en) | 2009-07-01 | 2013-12-31 | 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 |
| 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 |
| JP2012532144A (ja) | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
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| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
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| WO2015085004A1 (en) * | 2013-12-03 | 2015-06-11 | Intra-Cellular Therapies, Inc. | Novel methods |
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| KR20170012210A (ko) | 2014-04-04 | 2017-02-02 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| WO2015191554A1 (en) | 2014-06-09 | 2015-12-17 | 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 |
| EP3288921B1 (en) * | 2015-04-30 | 2022-06-15 | The Regents of the University of Colorado, a body corporate | Polycyclic indoline and indolenine compounds |
| PL3838274T3 (pl) | 2016-01-26 | 2024-04-02 | Intra-Cellular Therapies, Inc. | Pochodna pirydo[3',4':4,5]pirolo[1,2,3-DE]chinoksaliny do zastosowania w leczeniu zaburzeń OUN |
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| US11014925B2 (en) | 2016-03-28 | 2021-05-25 | Intra-Cellular Therapies, Inc. | Co-crystals of 1-(4-fluoro-phenyl)-4-((6bR,1OaS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3′,4′:4,51_pyrrolo [1,2,3-delqcuinoxalin-8-yl)-butan-1-one with nicotinamide or isonicotinamide |
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| EP3519816A4 (en) | 2016-09-29 | 2020-05-06 | The Regents of the University of California | Compounds for increasing neural plasticity |
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