CA2186412A1 - Ethylamino carbazole melatonergic agents - Google Patents
Ethylamino carbazole melatonergic agentsInfo
- Publication number
- CA2186412A1 CA2186412A1 CA002186412A CA2186412A CA2186412A1 CA 2186412 A1 CA2186412 A1 CA 2186412A1 CA 002186412 A CA002186412 A CA 002186412A CA 2186412 A CA2186412 A CA 2186412A CA 2186412 A1 CA2186412 A1 CA 2186412A1
- Authority
- CA
- Canada
- Prior art keywords
- carbazol
- dimethoxy
- ethyl
- nmr
- dmso
- 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.)
- Abandoned
Links
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- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
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- 238000000034 method Methods 0.000 claims description 26
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 208000019116 sleep disease Diseases 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFCSJZLDXYSEDU-UHFFFAOYSA-N 1-[2-(2,7-dimethoxycarbazol-9-yl)ethyl]-3-ethylurea Chemical compound C1=C(OC)C=C2N(CCNC(=O)NCC)C3=CC(OC)=CC=C3C2=C1 UFCSJZLDXYSEDU-UHFFFAOYSA-N 0.000 claims description 3
- KESPBAAVBJZTHB-UHFFFAOYSA-N n-[2-(2,7-dimethoxycarbazol-9-yl)ethyl]-2-methylpropanamide Chemical compound COC1=CC=C2C3=CC=C(OC)C=C3N(CCNC(=O)C(C)C)C2=C1 KESPBAAVBJZTHB-UHFFFAOYSA-N 0.000 claims description 2
- DLXZLRQKYQWLAE-UHFFFAOYSA-N n-[3-(2,7-dimethoxycarbazol-9-yl)propyl]cyclopropanecarboxamide Chemical compound C=1C(OC)=CC=C(C2=CC=C(OC)C=C22)C=1N2CCCNC(=O)C1CC1 DLXZLRQKYQWLAE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- MIAVEBMMDNBXOT-UHFFFAOYSA-N n-[2-(2,7-dimethoxycarbazol-9-yl)ethyl]propanethioamide Chemical compound C1=C(OC)C=C2N(CCNC(=S)CC)C3=CC(OC)=CC=C3C2=C1 MIAVEBMMDNBXOT-UHFFFAOYSA-N 0.000 claims 2
- OVTBHILTQSNEQP-UHFFFAOYSA-N n-[3-(2,7-dimethoxycarbazol-9-yl)propyl]butanamide Chemical compound C1=C(OC)C=C2N(CCCNC(=O)CCC)C3=CC(OC)=CC=C3C2=C1 OVTBHILTQSNEQP-UHFFFAOYSA-N 0.000 claims 2
- USPRDEXVEGWBKM-UHFFFAOYSA-N 1-[2-(2,7-dimethoxycarbazol-9-yl)ethyl]-3-methylurea Chemical compound C1=C(OC)C=C2N(CCNC(=O)NC)C3=CC(OC)=CC=C3C2=C1 USPRDEXVEGWBKM-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- MUYXUIRQEHDQQN-UHFFFAOYSA-N n-[2-(2,7-dimethoxycarbazol-9-yl)ethyl]-2-methoxyacetamide Chemical compound C1=C(OC)C=C2N(CCNC(=O)COC)C3=CC(OC)=CC=C3C2=C1 MUYXUIRQEHDQQN-UHFFFAOYSA-N 0.000 claims 1
- ZLCDEBKIKNIOEW-UHFFFAOYSA-N n-[2-(2,7-dimethoxycarbazol-9-yl)ethyl]butanamide Chemical compound C1=C(OC)C=C2N(CCNC(=O)CCC)C3=CC(OC)=CC=C3C2=C1 ZLCDEBKIKNIOEW-UHFFFAOYSA-N 0.000 claims 1
- WUDBRFDATZPALS-UHFFFAOYSA-N n-[2-(2,7-dimethoxycarbazol-9-yl)ethyl]cyclopropanecarboxamide Chemical compound C=1C(OC)=CC=C(C2=CC=C(OC)C=C22)C=1N2CCNC(=O)C1CC1 WUDBRFDATZPALS-UHFFFAOYSA-N 0.000 claims 1
- BOXCUMSNSSQKOW-UHFFFAOYSA-N n-[2-(2-methoxycarbazol-9-yl)ethyl]butanamide Chemical compound C1=C(OC)C=C2N(CCNC(=O)CCC)C3=CC=CC=C3C2=C1 BOXCUMSNSSQKOW-UHFFFAOYSA-N 0.000 claims 1
- MRBKHKXTNYDSBW-UHFFFAOYSA-N n-[2-(2-methoxycarbazol-9-yl)ethyl]cyclopropanecarboxamide Chemical compound C=1C(OC)=CC=C(C2=CC=CC=C22)C=1N2CCNC(=O)C1CC1 MRBKHKXTNYDSBW-UHFFFAOYSA-N 0.000 claims 1
- ZQBHLUNZKFFVNE-UHFFFAOYSA-N n-[3-(2,7-dimethoxycarbazol-9-yl)propyl]-2-methylpropanamide Chemical compound COC1=CC=C2C3=CC=C(OC)C=C3N(CCCNC(=O)C(C)C)C2=C1 ZQBHLUNZKFFVNE-UHFFFAOYSA-N 0.000 claims 1
- DJTYLKCQOIRIFO-UHFFFAOYSA-N n-[3-(2,7-dimethoxycarbazol-9-yl)propyl]acetamide Chemical compound COC1=CC=C2C3=CC=C(OC)C=C3N(CCCNC(C)=O)C2=C1 DJTYLKCQOIRIFO-UHFFFAOYSA-N 0.000 claims 1
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract 1
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
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- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- ITRBOGBMPGNZBO-AJRGADBESA-N undulifoline Chemical compound C1OCC[C@@H]2[C@H]3N(C)CC[C@@H]2[C@]1(C(=O)OC)C1=C3C2=CC=CC=C2N1 ITRBOGBMPGNZBO-AJRGADBESA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US815495P | 1995-10-31 | 1995-10-31 | |
| US60/008,154 | 1995-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2186412A1 true CA2186412A1 (en) | 1997-05-01 |
Family
ID=21730073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002186412A Abandoned CA2186412A1 (en) | 1995-10-31 | 1996-09-25 | Ethylamino carbazole melatonergic agents |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5677328A (https=) |
| EP (1) | EP0771791A1 (https=) |
| JP (1) | JPH09169730A (https=) |
| CA (1) | CA2186412A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100130579A1 (en) * | 2006-10-23 | 2010-05-27 | Georgetown University | Cancer therapy |
| ES2331274B1 (es) * | 2007-10-25 | 2010-10-21 | Ferrer Internacional, S.A. | Compuesto de indolina. |
| CN102186820B (zh) * | 2008-08-15 | 2013-08-28 | 乔治城大学 | Rassf1a表达和人癌细胞增殖的荧光调节剂 |
| WO2015003146A1 (en) | 2013-07-03 | 2015-01-08 | Georgetown University | Boronic acid derivatives of resveratrol for activating deacetylase enzymes |
| US11053255B2 (en) | 2015-06-22 | 2021-07-06 | Georgetown University | Synthesis of mahanine and related compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975398A (en) * | 1973-08-01 | 1976-08-17 | Boehringer Mannheim G.M.B.H. | 9-Substituted 3-aminocarbazole compounds |
| US5206377A (en) | 1991-12-05 | 1993-04-27 | Whitby Research, Inc. | Compounds useful as antiproliferative agents |
| US5449683A (en) | 1992-10-01 | 1995-09-12 | Massachussetts Institute Of Technology | Methods of inducing sleep using melatonin |
-
1996
- 1996-09-25 CA CA002186412A patent/CA2186412A1/en not_active Abandoned
- 1996-10-16 EP EP96116583A patent/EP0771791A1/en not_active Withdrawn
- 1996-10-30 US US08/741,485 patent/US5677328A/en not_active Expired - Lifetime
- 1996-10-31 JP JP8289439A patent/JPH09169730A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US5677328A (en) | 1997-10-14 |
| AU7049796A (en) | 1997-05-08 |
| AU701113B2 (en) | 1999-01-21 |
| EP0771791A1 (en) | 1997-05-07 |
| JPH09169730A (ja) | 1997-06-30 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20060925 |