NL8201420A - Nieuwe werkwijze voor het bereiden van 1-(4-chloorbenzoyl)-5-methoxy-2-methyl-3-indolyl-acetohydroxamzuur. - Google Patents
Nieuwe werkwijze voor het bereiden van 1-(4-chloorbenzoyl)-5-methoxy-2-methyl-3-indolyl-acetohydroxamzuur. Download PDFInfo
- Publication number
- NL8201420A NL8201420A NL8201420A NL8201420A NL8201420A NL 8201420 A NL8201420 A NL 8201420A NL 8201420 A NL8201420 A NL 8201420A NL 8201420 A NL8201420 A NL 8201420A NL 8201420 A NL8201420 A NL 8201420A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- methyl
- chlorobenzoyl
- methoxy
- indolyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- AJRNYCDWNITGHF-UHFFFAOYSA-N oxametacin Chemical compound CC1=C(CC(=O)NO)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 AJRNYCDWNITGHF-UHFFFAOYSA-N 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- -1 chlorobenzoyl Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 125000001477 organic nitrogen group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- TXWGINUZLBAKDF-UHFFFAOYSA-N N-Deschlorobenzoyl indomethacin Chemical compound COC1=CC=C2NC(C)=C(CC(O)=O)C2=C1 TXWGINUZLBAKDF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2091881 | 1981-04-03 | ||
| IT20918/81A IT1144692B (it) | 1981-04-03 | 1981-04-03 | Nuovo procedimento per la preparazione dell'acido 1-p-clorobenzoil-2-metil-5-metossi-2-indolacetoidrossammico |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8201420A true NL8201420A (nl) | 1982-11-01 |
Family
ID=11174057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8201420A NL8201420A (nl) | 1981-04-03 | 1982-04-02 | Nieuwe werkwijze voor het bereiden van 1-(4-chloorbenzoyl)-5-methoxy-2-methyl-3-indolyl-acetohydroxamzuur. |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59204172A (ja) * | 1983-04-28 | 1984-11-19 | Kowa Co | アセメタシンの製造法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2397508A (en) * | 1943-05-29 | 1946-04-02 | Standard Oil Co | Hydroxamic acids |
| US2785191A (en) * | 1952-07-03 | 1957-03-12 | Ciba Pharm Prod Inc | Acylmercapto-alkylamines and process for the manufacture thereof |
| FR1579495A (US07585860-20090908-C00112.png) * | 1968-01-22 | 1969-08-29 | ||
| IT1036004B (it) * | 1968-05-21 | 1979-10-30 | Abc Ist Biolog Chem Spa | Acidt 3 indolil adetoidrossamici |
| DE2008332C3 (de) * | 1970-02-23 | 1980-05-22 | Istituto Biologico Chemioterapico Abc S.P.A., Turin (Italien) | 2-Methyl-S-methoxy-3-indolylacetohydroxamsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2413125C2 (de) * | 1974-03-15 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Indolylacetylaminosäurederivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneipräparate |
| US4186133A (en) * | 1978-02-23 | 1980-01-29 | Istituto Biologico Chemioterapico "Abc" S.P.A. | Process for the preparation of an indole-3-acetohydroxamic acid |
-
1981
- 1981-04-03 IT IT20918/81A patent/IT1144692B/it active
-
1982
- 1982-03-17 CA CA000398632A patent/CA1164456A/en not_active Expired
- 1982-03-18 GB GB8207987A patent/GB2097388B/en not_active Expired
- 1982-03-22 US US06/360,819 patent/US4455432A/en not_active Expired - Fee Related
- 1982-03-24 FR FR8205032A patent/FR2503154A1/fr active Granted
- 1982-03-26 BE BE2/59647A patent/BE892645A/nl not_active IP Right Cessation
- 1982-03-30 DE DE19823211663 patent/DE3211663A1/de active Granted
- 1982-04-01 JP JP57055003A patent/JPS57176955A/ja active Granted
- 1982-04-01 ES ES511037A patent/ES511037A0/es active Granted
- 1982-04-02 NL NL8201420A patent/NL8201420A/nl not_active Application Discontinuation
- 1982-04-03 KR KR8201495A patent/KR860000649B1/ko active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57176955A (en) | 1982-10-30 |
| ES8302654A1 (es) | 1983-02-01 |
| IT1144692B (it) | 1986-10-29 |
| CA1164456A (en) | 1984-03-27 |
| IT8120918A0 (it) | 1981-04-03 |
| ES511037A0 (es) | 1983-02-01 |
| GB2097388B (en) | 1985-01-03 |
| GB2097388A (en) | 1982-11-03 |
| BE892645A (nl) | 1982-07-16 |
| DE3211663A1 (de) | 1982-10-21 |
| JPH0149151B2 (US07585860-20090908-C00112.png) | 1989-10-23 |
| FR2503154A1 (fr) | 1982-10-08 |
| KR830010068A (ko) | 1983-12-26 |
| US4455432A (en) | 1984-06-19 |
| FR2503154B1 (US07585860-20090908-C00112.png) | 1985-05-17 |
| KR860000649B1 (ko) | 1986-05-28 |
| DE3211663C2 (US07585860-20090908-C00112.png) | 1990-12-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20110306772A1 (en) | Process for the preparation of 2-chloro-5-chloromethyl-thiazole | |
| KR0176010B1 (ko) | 1-아미노-1,2,3-트리아졸의 제법 | |
| US4358596A (en) | Process for the preparation of 1,2,3-thiadiazol-5-yl ureas | |
| US5274166A (en) | Dithiocarbamic acid salt, process for production thereof, and process for production of isothiocyanate using said dithiocarbamic acid salt | |
| NL8201420A (nl) | Nieuwe werkwijze voor het bereiden van 1-(4-chloorbenzoyl)-5-methoxy-2-methyl-3-indolyl-acetohydroxamzuur. | |
| WO1997023469A9 (en) | Process for the preparation of 2-chloro-5-chloromethyl-thiazole | |
| KR100519420B1 (ko) | 헤테로아릴카복실아미드및에스테르의제조방법 | |
| JP2851524B2 (ja) | スルホニルウレア誘導体の製造方法 | |
| US4340742A (en) | Process for making 5-mercapto-1,2,3-triazoles | |
| US6087506A (en) | Preparation of hetero arylcarboxamides | |
| RU2193034C2 (ru) | Способ получения производных 2-аминотиазолкарбоксамида | |
| KR940008923B1 (ko) | 아미노아세토니트릴 유도체 | |
| JP3963523B2 (ja) | ジアゾ化合物の製造方法 | |
| US4234514A (en) | Method of preparing ketoxime carbamates | |
| US4147876A (en) | Easily hydrolyzable esters of 4-(2-carboxyethyl)phenyl trans-4-aminomethylcyclohexanecarboxylate and process of use | |
| KR830000271B1 (ko) | 1,2,3-티아디아졸-5-일 우레아의 제조방법 | |
| EP0123719A2 (en) | Processes for preparing 5-acyloxymethyloxazolidin-2-one-derivatives | |
| US4265825A (en) | Process for the preparation of N-(haloalkyl)sulfonamide | |
| US4257970A (en) | Novel sulfonyl imide intermediates | |
| JP4273224B2 (ja) | Ｎ−スルフェニル複素環化合物の製造方法 | |
| NL7905355A (nl) | Werkwijze ter bereiding van 1,2,3-thiadiazool-5-yl-urea. | |
| SU275883A1 (US07585860-20090908-C00112.png) | ||
| JPS5888361A (ja) | ３−アミノ−１，４−ビス（アルコキシカルボニル）マレイミド類およびその製法 | |
| JPH1135550A (ja) | イソチオシアネート化合物及びその製造法 | |
| JP2649122B2 (ja) | ４，５−ジハロゲノ−６−（α−置換エチル）ピリミジン及びその製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |