EA016592B1 - Трициклические производные изохинолина для лечения ожирения - Google Patents
Трициклические производные изохинолина для лечения ожирения Download PDFInfo
- Publication number
- EA016592B1 EA016592B1 EA200970849A EA200970849A EA016592B1 EA 016592 B1 EA016592 B1 EA 016592B1 EA 200970849 A EA200970849 A EA 200970849A EA 200970849 A EA200970849 A EA 200970849A EA 016592 B1 EA016592 B1 EA 016592B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- tetrahydro
- azepino
- indole
- sulfonyl
- phenylsulfonyl
- Prior art date
Links
- 208000008589 Obesity Diseases 0.000 title description 4
- 235000020824 obesity Nutrition 0.000 title description 4
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 250
- -1 1,2-dimethyl-1H-imidazol-4-yl Chemical group 0.000 claims description 137
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 133
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 125
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 125
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 77
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 33
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- 201000010099 disease Diseases 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
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- 239000003085 diluting agent Substances 0.000 claims description 2
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- 125000002541 furyl group Chemical group 0.000 claims description 2
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- 238000011160 research Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
- YDBPZCVWPFMBDH-UHFFFAOYSA-N tert-butyl 2-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C=O YDBPZCVWPFMBDH-UHFFFAOYSA-N 0.000 description 1
- DWLADVOODHZCFV-UHFFFAOYSA-N tert-butyl 3-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C=O)C1 DWLADVOODHZCFV-UHFFFAOYSA-N 0.000 description 1
- BLFAHMMBNUWZBH-UHFFFAOYSA-N tert-butyl 7-hydroxy-6-methyl-1-(phenylsulfonyl)-1,3,4,6-tetrahydro-5h-azepino[5,4,3-cd]indole-5-carboxylate Chemical compound C=12C3=CC=C(O)C=1C(C)N(C(=O)OC(C)(C)C)CCC2=CN3S(=O)(=O)C1=CC=CC=C1 BLFAHMMBNUWZBH-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0700611 | 2007-03-13 | ||
| US202907P | 2007-11-05 | 2007-11-05 | |
| PCT/EP2008/053002 WO2008110598A1 (en) | 2007-03-13 | 2008-03-13 | Tricyclic isoquinoline derivatives for treatment of obesity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200970849A1 EA200970849A1 (ru) | 2010-04-30 |
| EA016592B1 true EA016592B1 (ru) | 2012-06-29 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200970849A EA016592B1 (ru) | 2007-03-13 | 2008-03-13 | Трициклические производные изохинолина для лечения ожирения |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8138333B2 (enExample) |
| EP (1) | EP2134714A1 (enExample) |
| JP (1) | JP2010520917A (enExample) |
| CN (1) | CN101631787A (enExample) |
| AU (1) | AU2008225753A1 (enExample) |
| BR (1) | BRPI0808791A2 (enExample) |
| CA (1) | CA2679346A1 (enExample) |
| EA (1) | EA016592B1 (enExample) |
| NZ (1) | NZ579360A (enExample) |
| WO (1) | WO2008110598A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2724449C (en) | 2008-05-29 | 2017-05-30 | Albany Molecular Research, Inc. | 5-ht3 receptor modulators, methods of making, and use thereof |
| EP2575815A4 (en) | 2010-06-04 | 2013-12-25 | Albany Molecular Res Inc | GLYCIN TRANSPORTER 1 INHIBITORS, METHODS OF MAKING THE SAME, AND USES THEREOF |
| WO2012106448A1 (en) * | 2011-02-02 | 2012-08-09 | Biocryst Pharmaceuticals, Inc. | Heterocyclic compounds as janus kinase inhibitors |
| JP6198715B2 (ja) * | 2012-03-06 | 2017-09-20 | 武田薬品工業株式会社 | 三環性化合物 |
| US10675283B2 (en) | 2017-03-24 | 2020-06-09 | University Of South Florida | Compositions and methods for white to beige adipogenesis |
| CN109180687A (zh) * | 2018-08-31 | 2019-01-11 | 山东轩德医药科技有限公司 | 一种瑞卡帕步中间体的制备方法 |
| CN111961047A (zh) * | 2020-08-19 | 2020-11-20 | 南通大学 | 一种6-乙氧基-3,4-二氢-2,7-萘啶-1（2h）-酮及其合成方法 |
| CN115925658B (zh) * | 2022-11-21 | 2024-02-27 | 常州佳德医药科技有限公司 | 一种2-氨基乙基呋喃的制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3833591A (en) * | 1972-02-23 | 1974-09-03 | Pfizer | 1,3,4,5-tetrahydropyrrolo(4,3,2-d,e)isoquinolines and related compounds |
| US3950343A (en) * | 1973-11-06 | 1976-04-13 | Ayerst, Mckenna And Harrison Ltd. | Pyrroloisoquinoline derivatives |
| US6133287A (en) * | 1998-03-24 | 2000-10-17 | Allelix Biopharmaceuticals Inc. | Piperidine-indole compounds having 5-HT6 affinity |
| US20030229069A1 (en) * | 2002-06-05 | 2003-12-11 | Roche Palo Alto Llc | 1-Sulfonyl-4-aminoalkoxy indole derivatives and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9700693A (es) | 1994-07-26 | 1997-04-30 | Pfizer | Derivados del 4-indol. |
| GB9820113D0 (en) | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| MXPA01005905A (es) | 1998-12-11 | 2002-09-18 | Univ Virginia Commonwealth | Ligandos selectivos de receptores de 5-ht6. |
| WO2002032863A1 (en) | 2000-10-20 | 2002-04-25 | Biovitrum Ab | 2-, 3-, 4-, or 5-substituted-n1-(benzensulfonyl)indoles and their use in therapy |
-
2008
- 2008-03-13 BR BRPI0808791A patent/BRPI0808791A2/pt not_active IP Right Cessation
- 2008-03-13 EP EP08717746A patent/EP2134714A1/en not_active Withdrawn
- 2008-03-13 US US12/075,979 patent/US8138333B2/en not_active Expired - Fee Related
- 2008-03-13 JP JP2009553146A patent/JP2010520917A/ja not_active Withdrawn
- 2008-03-13 AU AU2008225753A patent/AU2008225753A1/en not_active Abandoned
- 2008-03-13 WO PCT/EP2008/053002 patent/WO2008110598A1/en not_active Ceased
- 2008-03-13 CN CN200880008061A patent/CN101631787A/zh active Pending
- 2008-03-13 EA EA200970849A patent/EA016592B1/ru not_active IP Right Cessation
- 2008-03-13 CA CA002679346A patent/CA2679346A1/en not_active Abandoned
- 2008-03-13 NZ NZ579360A patent/NZ579360A/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3833591A (en) * | 1972-02-23 | 1974-09-03 | Pfizer | 1,3,4,5-tetrahydropyrrolo(4,3,2-d,e)isoquinolines and related compounds |
| US3950343A (en) * | 1973-11-06 | 1976-04-13 | Ayerst, Mckenna And Harrison Ltd. | Pyrroloisoquinoline derivatives |
| US6133287A (en) * | 1998-03-24 | 2000-10-17 | Allelix Biopharmaceuticals Inc. | Piperidine-indole compounds having 5-HT6 affinity |
| US20030229069A1 (en) * | 2002-06-05 | 2003-12-11 | Roche Palo Alto Llc | 1-Sulfonyl-4-aminoalkoxy indole derivatives and uses thereof |
Non-Patent Citations (3)
| Title |
|---|
| L. STREKOWSKI ET AL.: "Synthesis of Analogs of the Ergot Alkaloids", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 37, 2000, pages 1495-1499, XP009101190, page 1496, compounds 17-19 * |
| R.E. BOWMAN ET AL.: "1,3,4,5-Tetrahydrobenz[cd]indoles and Related Compounds", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 15, 1972, pages 1926-1932, XP009101189, page 1928, compound 35 * |
| Y. YOKOYAMA ET AL.: "Optically Active Total Synthesis of Claviciptic Acid.", JOURNAL OF ORGANIC CHEMISTRY, vol. 60, 1995, pages 1486-1487, XP002483151, page 1487, compound 14 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2679346A1 (en) | 2008-09-18 |
| CN101631787A (zh) | 2010-01-20 |
| US20080293694A1 (en) | 2008-11-27 |
| AU2008225753A1 (en) | 2008-09-18 |
| BRPI0808791A2 (pt) | 2017-05-02 |
| WO2008110598A1 (en) | 2008-09-18 |
| EP2134714A1 (en) | 2009-12-23 |
| EA200970849A1 (ru) | 2010-04-30 |
| JP2010520917A (ja) | 2010-06-17 |
| NZ579360A (en) | 2011-06-30 |
| US8138333B2 (en) | 2012-03-20 |
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