SK137097A3 - Anellated 'beta'-carbolines, method for their producing, their use and medicaments containing these compounds - Google Patents
Anellated 'beta'-carbolines, method for their producing, their use and medicaments containing these compounds Download PDFInfo
- Publication number
- SK137097A3 SK137097A3 SK1370-97A SK137097A SK137097A3 SK 137097 A3 SK137097 A3 SK 137097A3 SK 137097 A SK137097 A SK 137097A SK 137097 A3 SK137097 A3 SK 137097A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- carboline
- carbon atoms
- carboxylic acid
- methoxymethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- -1 1,2-dihydroxyethyl Chemical group 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 6
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- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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- 125000004185 ester group Chemical group 0.000 claims description 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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- SFYLHIMXJQGKGZ-DUXPYHPUSA-N acetaldehyde (E)-hydrazone Chemical class C\C=N\N SFYLHIMXJQGKGZ-DUXPYHPUSA-N 0.000 claims description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- VQPXJKHKHAFSKW-UHFFFAOYSA-N 11-(methoxymethyl)-2,3,4,5-tetrahydro-1h-quinoxalino[3,2-g]$b-carboline-12-carboxylic acid isopropyl ester Chemical compound C1NCCC2=C1NC1=C2C2=NC3=C(C(=O)OC(C)C)C(COC)=CC=C3N=C2C=C1 VQPXJKHKHAFSKW-UHFFFAOYSA-N 0.000 claims 1
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- WBJPIBLXBFLWSR-UHFFFAOYSA-N 3,11-bis(methoxymethyl)-7h-pyrazino[2,3-g]$b-carboline-10-carboxylic acid isopropyl ester Chemical compound N1C2=CN=C(C(=O)OC(C)C)C(COC)=C2C2=C1C=CC1=NC(COC)=CN=C12 WBJPIBLXBFLWSR-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 102000004300 GABA-A Receptors Human genes 0.000 abstract description 8
- 108090000839 GABA-A Receptors Proteins 0.000 abstract description 8
- 102000001708 Protein Isoforms Human genes 0.000 abstract description 2
- 108010029485 Protein Isoforms Proteins 0.000 abstract description 2
- 230000001270 agonistic effect Effects 0.000 abstract 2
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/28—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
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19514524A DE19514524A1 (de) | 1995-04-12 | 1995-04-12 | Anellierte beta-Carboline |
| PCT/DE1996/000632 WO1996032392A1 (fr) | 1995-04-12 | 1996-04-03 | β-CARBOLINES ANNELEES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK137097A3 true SK137097A3 (en) | 1998-08-05 |
Family
ID=7759938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1370-97A SK137097A3 (en) | 1995-04-12 | 1996-04-03 | Anellated 'beta'-carbolines, method for their producing, their use and medicaments containing these compounds |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6127368A (fr) |
| EP (1) | EP0820454B1 (fr) |
| JP (1) | JPH11503432A (fr) |
| KR (1) | KR100379585B1 (fr) |
| CN (1) | CN1072224C (fr) |
| AT (1) | ATE221068T1 (fr) |
| AU (1) | AU703635B2 (fr) |
| CA (1) | CA2217719A1 (fr) |
| CZ (1) | CZ319997A3 (fr) |
| DE (2) | DE19514524A1 (fr) |
| HU (1) | HUP9801771A3 (fr) |
| IL (1) | IL117734A (fr) |
| MX (1) | MX9707784A (fr) |
| MY (1) | MY113450A (fr) |
| NO (1) | NO309568B1 (fr) |
| NZ (1) | NZ304823A (fr) |
| PL (1) | PL185554B1 (fr) |
| RU (1) | RU2169148C2 (fr) |
| SK (1) | SK137097A3 (fr) |
| TR (1) | TR199701156T1 (fr) |
| TW (1) | TW412535B (fr) |
| WO (1) | WO1996032392A1 (fr) |
| ZA (1) | ZA962946B (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4130933A1 (de) * | 1991-09-13 | 1993-03-18 | Schering Ag | Neue (beta)-carbolinderivate, deren herstellung und verwendung in arzneimitteln |
-
1995
- 1995-04-12 DE DE19514524A patent/DE19514524A1/de not_active Withdrawn
-
1996
- 1996-03-31 IL IL11773496A patent/IL117734A/xx not_active IP Right Cessation
- 1996-04-03 DE DE59609482T patent/DE59609482D1/de not_active Expired - Lifetime
- 1996-04-03 AT AT96909034T patent/ATE221068T1/de not_active IP Right Cessation
- 1996-04-03 CZ CZ973199A patent/CZ319997A3/cs unknown
- 1996-04-03 US US08/930,908 patent/US6127368A/en not_active Expired - Fee Related
- 1996-04-03 AU AU52696/96A patent/AU703635B2/en not_active Ceased
- 1996-04-03 WO PCT/DE1996/000632 patent/WO1996032392A1/fr not_active Application Discontinuation
- 1996-04-03 CN CN96193194A patent/CN1072224C/zh not_active Expired - Fee Related
- 1996-04-03 NZ NZ304823A patent/NZ304823A/xx unknown
- 1996-04-03 HU HU9801771A patent/HUP9801771A3/hu unknown
- 1996-04-03 KR KR1019970707225A patent/KR100379585B1/ko not_active IP Right Cessation
- 1996-04-03 EP EP96909034A patent/EP0820454B1/fr not_active Expired - Lifetime
- 1996-04-03 CA CA002217719A patent/CA2217719A1/fr not_active Abandoned
- 1996-04-03 TR TR97/01156T patent/TR199701156T1/xx unknown
- 1996-04-03 RU RU97118463/04A patent/RU2169148C2/ru not_active IP Right Cessation
- 1996-04-03 JP JP8530641A patent/JPH11503432A/ja not_active Ceased
- 1996-04-03 MX MX9707784A patent/MX9707784A/es unknown
- 1996-04-03 PL PL96322847A patent/PL185554B1/pl unknown
- 1996-04-03 SK SK1370-97A patent/SK137097A3/sk unknown
- 1996-04-12 ZA ZA962946A patent/ZA962946B/xx unknown
- 1996-04-12 MY MYPI96001393A patent/MY113450A/en unknown
- 1996-07-03 TW TW085108046A patent/TW412535B/zh not_active IP Right Cessation
-
1997
- 1997-10-10 NO NO974687A patent/NO309568B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11503432A (ja) | 1999-03-26 |
| EP0820454A1 (fr) | 1998-01-28 |
| NO974687D0 (no) | 1997-10-10 |
| CZ319997A3 (cs) | 1998-06-17 |
| DE19514524A1 (de) | 1996-10-17 |
| AU5269696A (en) | 1996-10-30 |
| EP0820454B1 (fr) | 2002-07-24 |
| PL185554B1 (pl) | 2003-05-30 |
| MY113450A (en) | 2002-02-28 |
| MX9707784A (es) | 1997-12-31 |
| TR199701156T1 (xx) | 1998-02-21 |
| RU2169148C2 (ru) | 2001-06-20 |
| IL117734A0 (en) | 1996-07-23 |
| CN1072224C (zh) | 2001-10-03 |
| TW412535B (en) | 2000-11-21 |
| KR100379585B1 (ko) | 2004-09-04 |
| KR19980703825A (ko) | 1998-12-05 |
| AU703635B2 (en) | 1999-03-25 |
| US6127368A (en) | 2000-10-03 |
| CN1181081A (zh) | 1998-05-06 |
| PL322847A1 (en) | 1998-02-16 |
| NZ304823A (en) | 1999-06-29 |
| HUP9801771A2 (hu) | 1998-11-30 |
| ZA962946B (en) | 1996-09-06 |
| NO309568B1 (no) | 2001-02-19 |
| IL117734A (en) | 1999-08-17 |
| NO974687L (no) | 1997-12-11 |
| WO1996032392A1 (fr) | 1996-10-17 |
| DE59609482D1 (de) | 2002-08-29 |
| HUP9801771A3 (en) | 1999-01-28 |
| ATE221068T1 (de) | 2002-08-15 |
| CA2217719A1 (fr) | 1996-10-17 |
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