NO300973B1 - Fremgangsmåte til fremstilling av 1,2,3,9-tetrahydro-9-metyl-3-£(2-metyl-1H-imidazol-1-yl)metyl|-4H-karbazol-4-on - Google Patents
Fremgangsmåte til fremstilling av 1,2,3,9-tetrahydro-9-metyl-3-£(2-metyl-1H-imidazol-1-yl)metyl|-4H-karbazol-4-on Download PDFInfo
- Publication number
- NO300973B1 NO300973B1 NO930887A NO930887A NO300973B1 NO 300973 B1 NO300973 B1 NO 300973B1 NO 930887 A NO930887 A NO 930887A NO 930887 A NO930887 A NO 930887A NO 300973 B1 NO300973 B1 NO 300973B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- imidazol
- formula
- tetrahydro
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title description 7
- -1 2-methyl-1H-imidazol-1-yl Chemical group 0.000 title description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000007171 acid catalysis Methods 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 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
- 230000002378 acidificating effect Effects 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OTAOHVAQDLTDBP-UHFFFAOYSA-N 4-(3-ethoxycarbonyl-1-methylindol-2-yl)-2-methylidenebutanoic acid Chemical compound C=C(C(=O)O)CCC=1N(C2=CC=CC=C2C=1C(=O)OCC)C OTAOHVAQDLTDBP-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- AMLYRCOEFHJSFS-UHFFFAOYSA-N carbazol-1-one Chemical compound C1=CC=C2C3=CC=CC(=O)C3=NC2=C1 AMLYRCOEFHJSFS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZFPUZZSDVPSGFJ-UHFFFAOYSA-N 2-(3-carboxybut-3-enyl)-1-methylindole-3-carboxylic acid Chemical compound C=C(C(=O)O)CCC=1N(C2=CC=CC=C2C=1C(=O)O)C ZFPUZZSDVPSGFJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- GUXGFEPITRBHDB-UHFFFAOYSA-N 2-[(2-methylimidazol-1-yl)methyl]-4-(1-methylindol-2-yl)butanoic acid Chemical compound CC=1N(C=CN=1)CC(C(=O)O)CCC=1N(C2=CC=CC=C2C=1)C GUXGFEPITRBHDB-UHFFFAOYSA-N 0.000 description 1
- 102000035037 5-HT3 receptors Human genes 0.000 description 1
- 108091005477 5-HT3 receptors Proteins 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- RQRUAENQOVZHNW-UHFFFAOYSA-N ethyl 1,2-dimethylindole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(C)N(C)C2=C1 RQRUAENQOVZHNW-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES09200552A ES2043535B1 (es) | 1992-03-13 | 1992-03-13 | Procedimiento para la obtencion de la 1,2,3,9-tetrahidro-9-metil-3-(2-metil-1h-imidazol-1-il)metil*-4h-carbazol-4-ona. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO930887D0 NO930887D0 (no) | 1993-03-11 |
| NO930887L NO930887L (no) | 1993-09-14 |
| NO300973B1 true NO300973B1 (no) | 1997-08-25 |
Family
ID=8276385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO930887A NO300973B1 (no) | 1992-03-13 | 1993-03-11 | Fremgangsmåte til fremstilling av 1,2,3,9-tetrahydro-9-metyl-3-£(2-metyl-1H-imidazol-1-yl)metyl|-4H-karbazol-4-on |
Country Status (15)
| Country | Link |
|---|---|
| KR (1) | KR100277414B1 (fi) |
| AR (1) | AR248019A1 (fi) |
| AT (1) | AT402730B (fi) |
| CZ (1) | CZ281753B6 (fi) |
| EG (1) | EG20262A (fi) |
| ES (1) | ES2043535B1 (fi) |
| FI (1) | FI105098B (fi) |
| GR (1) | GR930100094A (fi) |
| HU (1) | HU210775B (fi) |
| IS (1) | IS1783B (fi) |
| NO (1) | NO300973B1 (fi) |
| PL (1) | PL170751B1 (fi) |
| PT (1) | PT101216B (fi) |
| RU (1) | RU2109741C1 (fi) |
| SK (1) | SK278786B6 (fi) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100368895B1 (ko) * | 2000-03-30 | 2003-01-24 | 하나제약 주식회사 | 1,2,3,9-테트라하이드로-9-메틸-3-[(2-메틸-1ｈ-이미다졸-1-일)메틸]-4ｈ-카바졸-4-온의 제조방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE460359B (sv) * | 1984-01-25 | 1989-10-02 | Glaxo Group Ltd | 3-imidazolylmetyltetrahydrokarbazoloner, foerfarande foer framstaellning av dessa och en farmaceutisk komposition |
| GB8518742D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
| GB8518743D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8518741D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
| GB8617994D0 (en) * | 1986-07-23 | 1986-08-28 | Glaxo Group Ltd | Heterocyclic compounds |
-
1992
- 1992-03-13 ES ES09200552A patent/ES2043535B1/es not_active Expired - Fee Related
-
1993
- 1993-03-08 SK SK169-93A patent/SK278786B6/sk not_active IP Right Cessation
- 1993-03-09 GR GR930100094A patent/GR930100094A/el not_active IP Right Cessation
- 1993-03-10 EG EG14493A patent/EG20262A/xx active
- 1993-03-10 CZ CZ93396A patent/CZ281753B6/cs not_active IP Right Cessation
- 1993-03-11 KR KR1019930003609A patent/KR100277414B1/ko not_active IP Right Cessation
- 1993-03-11 PT PT101216A patent/PT101216B/pt not_active IP Right Cessation
- 1993-03-11 AR AR93324474A patent/AR248019A1/es active
- 1993-03-11 IS IS3985A patent/IS1783B/is unknown
- 1993-03-11 NO NO930887A patent/NO300973B1/no not_active IP Right Cessation
- 1993-03-12 RU RU93004833/04A patent/RU2109741C1/ru not_active IP Right Cessation
- 1993-03-12 AT AT0048793A patent/AT402730B/de not_active IP Right Cessation
- 1993-03-12 PL PL93298037A patent/PL170751B1/pl not_active IP Right Cessation
- 1993-03-12 HU HU9300718A patent/HU210775B/hu not_active IP Right Cessation
- 1993-03-12 FI FI931104A patent/FI105098B/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT402730B (de) | 1997-08-25 |
| ES2043535B1 (es) | 1994-08-01 |
| PT101216A (pt) | 1994-03-31 |
| PL170751B1 (pl) | 1997-01-31 |
| CZ39693A3 (en) | 1994-01-19 |
| FI931104A (fi) | 1993-09-14 |
| IS1783B (is) | 2001-10-22 |
| KR100277414B1 (ko) | 2001-01-15 |
| KR930019665A (ko) | 1993-10-18 |
| GR930100094A (el) | 1993-11-30 |
| HU210775B (en) | 1995-07-28 |
| NO930887D0 (no) | 1993-03-11 |
| SK16993A3 (en) | 1993-11-10 |
| RU2109741C1 (ru) | 1998-04-27 |
| CZ281753B6 (cs) | 1997-01-15 |
| HU9300718D0 (en) | 1993-05-28 |
| NO930887L (no) | 1993-09-14 |
| PL298037A1 (en) | 1993-12-27 |
| AR248019A1 (es) | 1995-05-31 |
| PT101216B (pt) | 1999-10-29 |
| SK278786B6 (sk) | 1998-02-04 |
| FI931104A0 (fi) | 1993-03-12 |
| ES2043535A1 (es) | 1993-12-16 |
| HUT64537A (en) | 1994-01-28 |
| ATA48793A (de) | 1996-12-15 |
| FI105098B (fi) | 2000-06-15 |
| IS3985A (is) | 1993-09-14 |
| EG20262A (en) | 1998-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |