NL194126C - Werkwijze voor de bereiding van een carbazoolderivaat. - Google Patents
Werkwijze voor de bereiding van een carbazoolderivaat. Download PDFInfo
- Publication number
- NL194126C NL194126C NL8001251A NL8001251A NL194126C NL 194126 C NL194126 C NL 194126C NL 8001251 A NL8001251 A NL 8001251A NL 8001251 A NL8001251 A NL 8001251A NL 194126 C NL194126 C NL 194126C
- Authority
- NL
- Netherlands
- Prior art keywords
- mixture
- methyl
- dried
- washed
- filtered
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WGRWLYZZSRECAS-UHFFFAOYSA-N 2-methyl-2-(3-oxocyclohexyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)(C)C1CCCC(=O)C1 WGRWLYZZSRECAS-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- OWNBALBCKYJEQU-UHFFFAOYSA-N 2-(6-chloro-9h-carbazol-2-yl)-2-methylpropanedioic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)(C(O)=O)C)C=C3NC2=C1 OWNBALBCKYJEQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- YQVZREHUWCCHHX-UHFFFAOYSA-N (4-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Cl)C=C1 YQVZREHUWCCHHX-UHFFFAOYSA-N 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000012065 filter cake Substances 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000005899 aromatization reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- YEUVYOAJWUVGAO-UHFFFAOYSA-N 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-methylpropanedioic acid Chemical compound N1C2=CC=C(Cl)C=C2C2=C1CC(C(C)(C(O)=O)C(O)=O)CC2 YEUVYOAJWUVGAO-UHFFFAOYSA-N 0.000 description 1
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- PUXBGTOOZJQSKH-UHFFFAOYSA-N carprofen Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3NC2=C1 PUXBGTOOZJQSKH-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 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 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH210479 | 1979-03-02 | ||
| CH210479A CH637117A5 (de) | 1979-03-02 | 1979-03-02 | Verfahren zur herstellung eines carbazolderivates. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8001251A NL8001251A (nl) | 1980-09-04 |
| NL194126B NL194126B (nl) | 2001-03-01 |
| NL194126C true NL194126C (nl) | 2001-07-03 |
Family
ID=4225963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8001251A NL194126C (nl) | 1979-03-02 | 1980-02-29 | Werkwijze voor de bereiding van een carbazoolderivaat. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4264500A (de) |
| JP (1) | JPS603383B2 (de) |
| KR (1) | KR840000115B1 (de) |
| AT (1) | AT374180B (de) |
| CA (1) | CA1128952A (de) |
| CH (1) | CH637117A5 (de) |
| DK (1) | DK145741C (de) |
| ES (1) | ES8103733A1 (de) |
| GR (1) | GR67216B (de) |
| HU (1) | HU178840B (de) |
| LU (1) | LU82205A1 (de) |
| NL (1) | NL194126C (de) |
| NO (1) | NO153134C (de) |
| PT (1) | PT70888B (de) |
| SE (1) | SE431870B (de) |
| YU (1) | YU18580A (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0321147U (de) * | 1989-07-06 | 1991-03-01 | ||
| US6013808A (en) * | 1998-06-16 | 2000-01-11 | Pfizer Inc. | Method of purifying carbazole ester precursors of 6-chloro-α-methyl-carbazole-2-acetic acid |
| US6268526B1 (en) | 1998-12-16 | 2001-07-31 | Albemarle Corporation | Palladium catalyzed carbonylation process utilizing aromatic substituted alcohols and/or aromatic substituted alkyl halides |
| US9611217B2 (en) | 2015-05-06 | 2017-04-04 | Chemwerth, Inc. | Synthetic processes of carprofen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3896145A (en) * | 1972-07-24 | 1975-07-22 | Hoffmann La Roche | Carbazoles |
| US4158007A (en) * | 1978-08-21 | 1979-06-12 | Hoffmann-La Roche Inc. | Carbazole methyl malonates |
-
1979
- 1979-03-02 CH CH210479A patent/CH637117A5/de not_active IP Right Cessation
-
1980
- 1980-01-16 CA CA343,748A patent/CA1128952A/en not_active Expired
- 1980-01-24 YU YU00185/80A patent/YU18580A/xx unknown
- 1980-02-20 NO NO800458A patent/NO153134C/no unknown
- 1980-02-27 HU HU8080439A patent/HU178840B/hu unknown
- 1980-02-28 LU LU82205A patent/LU82205A1/de unknown
- 1980-02-28 US US06/125,529 patent/US4264500A/en not_active Expired - Lifetime
- 1980-02-29 SE SE8001617A patent/SE431870B/sv not_active IP Right Cessation
- 1980-02-29 PT PT70888A patent/PT70888B/pt unknown
- 1980-02-29 DK DK89280A patent/DK145741C/da not_active IP Right Cessation
- 1980-02-29 AT AT0113880A patent/AT374180B/de not_active IP Right Cessation
- 1980-02-29 NL NL8001251A patent/NL194126C/nl not_active IP Right Cessation
- 1980-02-29 JP JP55024199A patent/JPS603383B2/ja not_active Expired
- 1980-02-29 KR KR1019800000857A patent/KR840000115B1/ko not_active Expired
- 1980-02-29 GR GR61318A patent/GR67216B/el unknown
- 1980-03-01 ES ES489119A patent/ES8103733A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL8001251A (nl) | 1980-09-04 |
| HU178840B (en) | 1982-07-28 |
| KR840000115B1 (ko) | 1984-02-16 |
| NO153134B (no) | 1985-10-14 |
| AT374180B (de) | 1984-03-26 |
| CA1128952A (en) | 1982-08-03 |
| DK145741C (da) | 1983-08-01 |
| JPS603383B2 (ja) | 1985-01-28 |
| KR830001890A (ko) | 1983-05-19 |
| JPS55118461A (en) | 1980-09-11 |
| DK145741B (da) | 1983-02-14 |
| NL194126B (nl) | 2001-03-01 |
| US4264500A (en) | 1981-04-28 |
| ATA113880A (de) | 1983-08-15 |
| LU82205A1 (de) | 1981-09-10 |
| ES489119A0 (es) | 1981-03-16 |
| PT70888A (en) | 1980-03-01 |
| NO153134C (no) | 1986-01-22 |
| YU18580A (en) | 1983-04-30 |
| ES8103733A1 (es) | 1981-03-16 |
| NO800458L (no) | 1980-09-03 |
| PT70888B (en) | 1981-06-11 |
| CH637117A5 (de) | 1983-07-15 |
| SE8001617L (sv) | 1980-09-03 |
| DK89280A (da) | 1980-09-03 |
| GR67216B (de) | 1981-06-24 |
| SE431870B (sv) | 1984-03-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| A85 | Still pending on 85-01-01 | ||
| BC | A request for examination has been filed | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: HOFFMANN-LA ROCHE AG. F. - |
|
| V4 | Discontinued because of reaching the maximum lifetime of a patent |
Free format text: 20010703 |